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A supportive girlfriend   3 comments

A supportive girlfriend

By Elizabeth James

My name is Kelly well actually it is Kelly James Johnson which wouldn’t normally be bad accept for my size. By the time I in the 6 grade I was as tall as I was going to get, 5’5” tall and puberty never really hit me. By the time I started 10 grade I still looked like I was 12 years old, no body hair, and no facial hair it was hard growing up. So when I started 10 grade I started going by my middle name James as with my size I didn’t want a name that could be male or female. High School was hard but I made it through, imagine being a boy that was smaller than half the girls in the school. I did 2 years of community college before transferring to a 4 year college. I led a lonely life as it seemed all the girls wanted the tall, strong, athletic guys.

It was the start of my last year that I met Jill, she was a beautiful girl, long blonde hair, 5’6” tall and looked like a model. I am not even sure why but she sat down across from me in the library one day and soon we were talking. She didn’t seem to even notice my size and we became friend and soon we were dating which was a little hard as I was an inch shorter than her and more than once people mistook me for her little brother. At Christmas we started talking and to save money we decided I should move into her apartment as it was a little bigger than mine and closer to school. I was thrilled. It was New Year’s night and we had had way too much to drink and after midnight we got talking and I don’t know why I asked her why she wanted to be with a guy as small as me one people mistook for her little brother. As soon as I asked it I regretted it I mean why risk it and point it out to her. As I said we had both been drinking. She looked at me and said I hope you don’t take this wrong or think bad of me but she did not find tall strong men attractive and she hated body hair or facial hair on men. She told me that for a while she thought she was strange that way. I felt better as she actually did like me for me.

We talked for a couple hours that night till we both stumbled to bed, I am not sure if I was helping her or she helped me but somehow we made it to the bed. In the morning when we woke up somehow I was wearing her nightie and she had on my pajamas. We both got a good laugh out of that. A couple nights later we were talking at dinner and Jill brought that night up and asked me if I had ever thought about dressing as a girl which caught me off guard. I said no as I really had never thought about it even though in high school I got called a girl a lot. She smiled at me and told me I would make a passible girl which no male really wants to hear but before I could say anything she just told me to forget it as she was just thinking about getting into clubs to go dancing. You see she has a fake ID which is how we got the liquor for new year’s but there was no way I could pass for 21 even with a fake id. Now the funny thing is even though I had never thought of it before now it was stuck in my mind you know how someone mentions a song and then you can’t get it out of your head.

Well the next night I brought it up and told her that since she had mentioned it I couldn’t get the thought out of my mind. I didn’t think I could pass as a girl and I knew I wouldn’t have the courage to go out as a girl but I was curious as to what I would look like. Now I must ad my hair is a little long as I wear it in a ponytail I guess trying to look a little cool. Jill told me we would try it this Saturday and see what I looked like.

Saturday came and I was a little nervous, Jill had me shower and wash my hair with her shampoo and conditioner, when she combed it out my light brown hair was just to my shoulders. She used some curlers and a curling iron and actually gave me a pretty feminine hair style. Then she did my makeup, eye shadow, mascara, blush and finally a red lipstick. I could not believe how feminine I looked. She then gave me a pair of her panties pink and a pink bra which she padded out and then one of her dresses which was just a little tight seems even though she is an inch taller I weigh just a little more and then a pair of her heels which actually fit me well. The end result was I looked completely like a girl. I don’t think even my own mom would recognize me if she was still alive. I spent the weekend as a girl and I actually had fun. Jill tried to get me to go out with her but I just couldn’t leave the apartment like this. I know I would pass but there was just something that wouldn’t let me do it.

It is funny as all weekend Jill called me by my first name Kelly. So this is how it went for a while. On weekends we were staying home I would dress as a girl and I was Kelly and when I was not dressed as a girl I was James. Summer came and we graduated and I got to meet Jill’s mom Helen. I only met her briefly at Graduation as she lived in another state. Turns out Jill had not told her she was living with her boyfriend. She told her she lived with Kelly and was dating me James. Her mom was only there for the weekend and had a hotel room so it was easy to keep up the lie as Jill told her mom Kelly was away visiting her family.

Well after graduation neither one of us found good jobs. I turned 21 still looking like a little kid and Jill was turning 21 on August 2. Jill had put in an application in Las Vegas for a cocktail waitress at a big casino and they had offered her a job starting on August 10th and as I didn’t have a job here we decided to move there and see if things were better.

Now are plan was to fly to Las Vegas on Sunday morning August 8th, We don’t have much to move, a TV some dishes and clothes so what we can’t take on the plain we will just ship down there by FED Ex to the Hotel we are going to stay at till we find an apartment. The only issue was money but Jill’s mom Helen let us use her credit card to pay for the airline tickets. Now with this she knew we intended to live together there she still didn’t know we had been living together for a half year already. Now as it started getting closer we both got a little nervous and wondered if we had made the right choice which I guess is normal but we were going ahead no matter what.

Now I was thinking about my weekends as Kelly, I know that is a strange thought but I realized I would probably have to stop this at least for a while. Now Jill had some things she had to do on Saturday the 7th and I figured I would take the opportunity to spend one last day as Kelly before we move. I didn’t mention this to Jill as I have actually gotten pretty good doing my own hair and makeup. Jill must have been thinking the same thing as she mentioned maybe I should spend Saturday as Kelly and maybe we could go out for dinner that night as we would be moving away the next day. I told her I would be Kelly but wasn’t sure I would be able to go out.

Saturday I got up and got all dressed as Kelly and Jill tried to talk me into going with her for the day. I told her I would think about dinner but there was no way I could spend the whole day out. Jill gave me a kiss and she was off. Now I was cleaning up the apartment to get it ready so when we left we would get our cleaning deposit back. We lived on the 5th floor and the garbage room was just 2 doors down from our apartment and I just wondered if I could walk down there with the garbage. I had 4 big bags, I grabbed one and cracked the door open and there was no one in the hall. I decided to try it, I opened the door stepped out and pulled the door almost shut putting the lock bar out so it wouldn’t shut all the way. I quickly walked 2 doors down and put the bag in the can and back to the room. Wow I couldn’t believe the rush I got from that even though I was really scared. I took a deep breath and worked up the courage to do it again. Same thing open the door, pull it almost closed and put the lock bar out to hold the door open. Walked a little slower this time but still got back to the room quickly.

I grabbed the 3rd bag opened the door, stepped out and pulled it almost shut when I heard a voice say hi, I spun around dropping the bag. It was Jill’s Mom Helen, She said sorry she startled me and helped me pick up the bag. She said she was here to see Jill. I told her Jill was out for the day taking care of business before she moved. Walked the garbage down the hall and this time walking slower as Helen walked with me and I didn’t want her to recognize me which I didn’t think she would as I really did look different.

Helen finally said oh you must be her roommate Kelly, nice to finally meet you. On the way back to the apartment she asked if she could wait there. I didn’t know what to say. I couldn’t let her in as she would see the apartment pretty much empty of course I could tell her I was also moving as I couldn’t afford this apartment on my own. Amazing how fast your mind works when you are scared. I told her Jill said she would be gone all day and she said that was too bad as she wanted to spend the day with her before she moved. We got back to the apartment and the door was shut. I got that scared look as I tried the door and it was locked. I was locked out. Helen must have realized what had happened as she told me she felt like it was her fault for startling me. I didn’t know what to do. Helen told me she would take me to lunch I knew I could just stand there in the hall so reluctantly I agreed.

I was never so scared going down the elevator and walking out to her car. I was relieved once I was in her car. We drove to a little café at the shopping center down the street. It was after lunch so it wasn’t real busy which I was glad for. Now we sat there at lunch and we talked and I was scared again doing my best to make sure she didn’t figure it out. We spent almost 2 hours at the café and by the time we were ready to leave I was feeling like I had fooled her as she had seemed to accept me as Kelly her daughter’s roommate. Helen gave the waitress her credit card for the bill. She pulled out her cell phone and made a call.

Now I got scared again when I heard her say hi honey, I am in town to see you before you leave. There was a pause for a moment and I heard well why don’t I take you and James out to dinner tonight. We can meet at Henry’s at 6 for dinner her treat. There was another pause and I heard her say that’s too bad James can’t make it but I will see you at 6 and she hung up. She looked at me and said oh I forgot to mention you were locked out well you can have dinner with us and then go home with Jill. I guess we will be spending the day together. I didn’t know what to say but I knew I had no choice so I said that sounded like fun.

I figured we would go back to her but instead we walked over to a small shopping center and went to a salon there, Helen told me she had planned on spending the day here with Jill before she left. I wasn’t sure what to do so I went along with it. We went in and started off with a pedicure which was actually really nice. They painted my toes a beautiful red color.

Next came a manicure the lady filed and trimmed my nails pretty short and then glued tips on them. I looked at Hellen and she just smiled you will love long nails but if not you can remove them. Again not knowing what to do I went along with it? Soon I had beautiful long nails painted the same red and they were a half inch long.

Next came the hair a wash, trim and set. My hair now looked shiny and smooth and I think a little more blonde. The last part was a facial and this made me the most nervous as the lady removed all my makeup. Luckily Helen was 2 chairs away so I figured I was safe. Creams were applied and a mask and more creams it really was a fun experience At least up to the point I felt a pain on my eye brows. Turns out she waxed them. Once she was done she started my makeup again. She did a wonderful job and did the same color red on my lips as they did on my nails.

I finally got a look at what they had done and I was right, my hair was a little more blonde and my eye brows although they were not overly masculine before they were high feminine arches now but the makeup was flawless. I looked so beautiful. There was no way anyone would know I was not a female. Helen asked me if I liked it and without thinking about it I told her I looked beautiful and thanked her. We left the salon and drove downtown to Henry’s and waited for Jill. Now I was worried as Jill did not know I would be there or what had happened today. We were a little early so Helen and I went to the bar to wait for Jill. Helen called Jill and told her we she meet her in the bar and at this point also told her about me Kelly getting locked out and I was joining us. There was a pause and Helen handed me the phone. Jill asked me what had happened and I gave her a quick rundown without going into too much detail.

Jill walked in at 6 and Helen got up and gave her a hug I stood up and Jill looked at me and said wow girl you look fabulous and also gave me a hug which helped as I was a little worried about all that had happened today. I never thought I would be able to go out to dinner with Jill as a girl. We were shown to our table and we all looked over the menu as we talked. It was very pleasant and with Jill here Helens attention was turned more to her than me.

Helen finally brought up the question Jill had worried about and the reason she never told her mom we were living together, she asked if Jill and James were thinking of getting married. Now to be honest we have talked about it we even went as far to talk about getting married when we get to Las Vegas. Helen looked at me and asked me what I thought of Jill and James getting married and didn’t I think they made a cute couple. Now I had to agree but it is strange to be involved in a conversation about yourself and your future with someone who doesn’t know you are that person. First I did agree that they made a perfect couple and it would be good if they got married. Helen looked at Jill and told her Kelly agreed with her about them getting married and made the comment I would make a wonderful maid of honor. Wow this was getting interesting. Are dinner came and as we ate Helen was still talking about marriage and I felt bad for Jill as she was taking all of this by herself but as much as I wanted to help I had to stay in the Kelly roll. Jill finally said that she was pretty sure James and she would be married once they got to Las Vegas as they both really did love each other. Helen gave her a hug and said that was all she wanted, for her daughter to be happy and as long as she and James truly loved each other and were planning on getting married she could support their living together. This made Jill really happy and me too although I had to hide it.

After dinner as we had desert Helen told Jill she had a surprise for her. Jill asked what and her mom told her she was on vacation for two weeks and had decided to go to Las Vegas with James and her and help us move and get settled in. she had bought another plane ticket on the same flight. All 3 of us would fly out at 9 am tomorrow. Jill was surprised for sure but tried to act happy I on the other had was really worried. Even removing these long nails there was nothing I could do about my eye brows or my lighter colored hair. Helen would notice for sure.

Helen then finally sad she had one more question for Jill and asked when she was going to tell her the whole truth and then she looked at me and asked me the same question. I know I had a panicked look on my face. She smiled and told us both to relax and then pointed out that we had used her credit card for the plane ticket, she had got the conformation for the tickets also including the one for Kelly James Johnson. She looked at me and said it is fine I just wish you two had not been lying to me all this time. I know you two love each other and that is all that matters.

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My Grandma part 2   3 comments

Continuation of my Grandma read this first

My Grandma part 2

By Elizabeth James

Well as I sat there waiting for mom my Grandma could tell I was nervous and told me not to worry. Mom loves me no matter what just like she does which did make me feel a little better. Well it was about 5 pm when mom got home and I was so scared I could hardly move as I waited. Grandma met her at the door and they talked for a minute as I stood in the kitchen listening. I was a little shocked to learn my mom had also known for several months I guess my Grandma had told her. Finally my mom called out to me, Jennifer come in here and let me see my daughter. It took every bit of concentration to get my feet to move but I did and I slowly walked into the front room and stopped. My mom walked over to me and looked me over as I waited. Finally she spoke, my what a beautiful daughter I have and she gave me a bug. I hugged her so hard back as I was so relieved but also I was afraid to let go.

Mom walked me over and we sat on the couch and she smiled at me, first let me tell you she said, I love you no matter what, I just want you to be happy that being said I am a little sad you felt you had to hide this from me but that is behind us now. She smiled again I am happy to have a daughter as I always wanted a girl also and if you want to be my daughter instead of my son or if you just want to be my daughter for a little while that is okay, I would even be okay with you being both from time to time as long as you are happy, do you understand. I nodded my head yes. Now for our trip and need an honest answer from you and I will be okay either way, do you want to go as Jennifer or David. I thought for a moment to make it look as though I was having trouble making up my mind which was not the case as the thought of being Jennifer for a full week was just too much for me. I finally spoke up and said Jennifer.

I could see the smile on my mom’s face as she gave me a hug, I am glad dear as I have had a son for 18 years it will be nice to have a daughter for a little while. With that mom told me to go and touch up my makeup and grab my purse as she was taking us out for dinner. While I did this mom changed into a dress and heels and the 3 of us went out the door and walked out to her car on the street, it wasn’t till I had gotten into the car I thought about how I had just walked out like it was nothing, I looked around and saw none of my neighbors though.

We got to the restaurant which was a really nice one and we all walked in. a few of the men did turn and watch us but then my mom is a very pretty woman and even my grandma was looking hot. We all looked at the menu and I found what I wanted to eat but when the waiter came to take our order my mom ordered a chicken Caesar salad for both of us and a glass of water. After the waiter left I was going to say something when mom spoke up, Jennifer dear as my daughter there are things you will need to learn and do and I will help you. First is your diet, it is okay for boys to eat anything but not young ladies, we need to watch our weight and figures so as Jennifer you will be eating less and more vegetables and fruit and cutting out sugar and that includes soft drinks. She smiled at me I am thrilled to have a daughter but as such I am going to treat you as my daughter and I expect you to act like a proper young lady would. I know you have been having fun but there are some things you need to learn. Young ladies walk, sit, stand and move different then young men. I looked at her and said okay but before I finished she stopped me. That is yes mom, young ladies always use proper English. It will be yes or no not okay or yah. I smiled and replied yes mom.

We had a nice dinner and then went home and it was time for me to get ready for bed. Mom handed me a pink teddy to wear and told me to go and wash my face, brush my teeth and put my hair into a pony tail so off I went to the bathroom. I started to wash my face and found my new long nails got in the way, now I had noticed little things today sense I had got them but nothing to bad but now I was really noticing them same when I tried to braid my hair, I had to ask mom for help. She smiled and told me I would get use to the nails and soon I would not have any issues. I was all ready for bed and both Grandma and mom came in and kissed me good night.

Sunday morning mom woke me up at 6 am to start getting ready. After my shower mom showed me how to put curlers in my hair to bring back the style I had and then she helped me with my makeup she did my eyes with browns and some black to give me that smoky eye look not the night time dramatic look but very flattering to my face and finished it off with a matt red lipstick. I looked very pretty and somehow older. I put on the white skirt and pink top and 3″ heels and then we combed out my hair and there was that beautiful girl. She told me to take my suitcases down stairs and be careful not to break a nail while she got ready. Grandma and I waited for mom down stairs for about 20 minutes but finally she came down. Mom came over and gave me a hug and Grandma just looked at us. I was not sure why and mom smiled at her and said I know it is amazing and I figured they were talking about how I looked. Finally mom walked me over buy the mirror and we stood there. I looked in the mirror and I was in shock, I actually looked so much like my mom. Our hair was the same style and color, our makeup was done the same, we both had on a white skirt although she had her flight attendant top on and heels.

Well it was time to leave and we all grabbed our suitcases and walked them out to the car, now I will admit carrying two suitcases with long nails and walking in heels is a lot more difficult but we managed to get everything into the car, Mom drove and Grandma sat up front and I was in the back and off we went to the airport. This was all so exciting. We got to the airport and parked in the long term parking which means we had to catch a shuttle bus to the airport and again here we were 3 females with way to much luggage, we were struggling with our luggage when two young men came up, probably business men as all they had were computer bags and they helped us get our luggage on the bus.

Well we got to the airport and checked our bags and then went to the security check where we had to stand in line. Now standing here in line I got a little scared as I wasn’t sure what all they were going to search but we made it through fine and then we found a little coffee shop to have breakfast as we still had over an hour till we could board the plan. After we ate we went to our gate and sat waiting for the plane. I was talking to mom and didn’t notice another family come over and sit down, it was a husband and wife and their daughter who was probably the same age as me, well before I knew it her and I were talking, and her name was Linda. Well it turns out she was going to Hawaii with her parents for the week also and they were staying in the same hotel as we were. Meanwhile my mom and Grandma were talking with her parents.

It was time to get on the plane and mom pulled some strings as she worked for the airline and got my seat next to Linda so we had the whole flight over to talk and get to know each other. Now we were ready to take off when it finally sunk in what I was doing. There was no turning back as I had no male clothes and when we landed I would be thousands of miles from home. I was quiet for a little bit but soon I was back talking with Linda. She was also 18 and just graduated and like me this was her graduation present. By the time we landed in Hawaii were knew so much about each other and the funny thing is I really didn’t have to lie that munch. We talked about school, what we liked, what we wanted to do now that we had graduated the only hard part was when she asked me if I had a boyfriend and I simply said no I was not dating anyone at the moment which was true. It was funny how similar my life was now and before other than it seemed easier to talk with people and I felt more at ease which really made no sense as I was passing myself off as a girl. Well the flight was a little over 5 hours but finally we made it to Hawaii.

We all walked down to the baggage claim area and we started to pull our luggage off the belt as it came by. A couple times Linda’s dad helped us and then he put all our luggage on a cart and wheeled it out to the curb. He even put it in a cab for us and as we were leaving he asked if we would like to join him and his wife for dinner tonight which my mom accepted and we agreed to meet in the hotel lobby at 6.

We got checked into our room and which was nice, it had a balcony and two bedrooms so Mom and Grandma would share and I would have my own. Now Linda called our room to see what I was wearing for dinner and I wasn’t sure what to say as I had never had that happen before. Mom told me it was just that girls had a little competition when it came to dressing, you never want to be way underdressed or overdressed so mom talked to Linda’s dad about the restaurant we were going to which turned out to be a really nice one so she told Linda that all three of us would be in dresses and heels tonight and she actually sounded excited about it. So there I was at 5:30 in a pretty somewhat short black dress and my 4″ heels and my makeup looking perfect. My Grandma had on a really pretty blue dress and heels and my mom also had on a black dress but hers showed more cleavage then mine. I thought we may have over done it for dinner. Well we all went downstairs to meet up with Linda and her parents. Her dad had on just a dress shirt and a nice pair of slacks nothing special and then I saw Linda and her mom. Her mom had on this beautiful red dress just as tight and low cut as my mom’s and Linda also had a red dress very pretty but like me not as sexy, both had on high heels and makeup perfect. We all looked like we had just come from the beauty salon on our way to a Hollywood party that is except for Linda’s dad. I guess girls just put way more effort into how they look.

We had a great dinner and again mom told me I should order a salad which I did and to my amazement so did mom, Grandma, Linda and her mom only Linda’s father ordered a steak. Mom must have realized what I was thinking and whispered in my ear, sweetie woman are always worried about the figure and weight especially when they are with other woman or someplace really warm as they want to look good. We had a great dinner and really got to know each other and my mom and Linda’s mom decide we would do things together this week as her husband was actually here on a business trip so he would only be with them in the evenings. Well it was almost 9 when we left the restaurant and headed for our rooms as it had been a long day and we were all pretty tired. Linda’s mom said we should spend the day tomorrow on the beach and why don’t we meet at 10 am. My mom said that was fine but Linda whispered something to her mom and she laughed and said let’s make it 11 okay so it was all set.

As we got up to the room it finally hit me we were going to the beach. I didn’t have a swim suit to wear and it would be hard to find a girls suit that I could wear and not be exposed. I told mom this and she just smiled, don’t worry sweetie I have already taken care of that. I cleaned off my makeup and went to bed, I must have been tired as I was asleep as soon as my head hit the pillow.

Mom woke me up in the morning and had me take a shower and for the first time she actually put hair remover all over my body even though I hardly had any. Any way after my shower I could not help but notice how soft and wonderful my skin felt. Well she helped me do my makeup yes that is right we did makeup but we used makeup that was water proof so it would still look good when we got wet. I went into my mom’s room and my mom was in this really pretty and well skimpy bikini and she looked awesome. It was a red color and wow I knew she would turn a lot of heads on the beach. My grandma had on a really pretty black swimsuit. It was a one piece but it was still open in the middle and did show of some skin. I looked on the bed and there was a bikini in hot pink, I looked at mom and told her there was no way I could wear that. She just smiled and told me she had taken care of everything, then she told me to take off my robe which caught me off guard as that would mean I was naked which I had not done in front of my mom for years. Any way with a little encouragement from her I was soon naked. She pulled out this little pair of what looked like panties that was the same color as the bikini and held them up, this is a gaff Jennifer, I got 10 pairs in different colors and they are designed for men to hide what women do not have. She had me step into it and worked it up towards my waist and it was already tight. She then told me it would feel uncomfortable for a bit but I would get used to it. Then it happened something I was not ready for. Mom grabbed my private parts, she pushed my testicles up inside my abdomen and pulled my penis down between my legs and then pulled the gaff up around my waits. I actually got light headed from the feeling. It was so tight that nothing showed. Mom had me walk around for a little bit and sit down and get up to see how it fit and stayed in place and it did still nothing showed, I was amazed and she was right after a bit the pain went away although it was still not so much uncomfortable but it just felt different.

She looked at me and smiled this will work not I want you to take it off and out it back on just the way I did. I was a little confused but mom just smiled, Sweetie I can’t be doing this for you. If you go to the bathroom you will have to be able to do this yourself so I did and to my amazement it wasn’t that hard to do, after the 3 time I had it down. Now my bikini was a string bikini so mom pulled up the bottoms and then showed me how to twist the strings around the sides of the gaff to make them look like they were all the same thing and as the gaff was a thong back nothing showed and as hard as we both looked you could not tell I had anything on other than the bikini bottoms.

Now the bikini top had some padding built in but I knew it would not be enough. Mom pulled out what she called a Nu bra it was two small silicon breast enhancers. I wasn’t sure what good this would do but she said I had enough baby fat on my chest to make it work. She then put some form of adhesive on the sides of my chest and also on the enhancers and then pressed them to the outside part of my chest just past my nipples and held them for a few minutes. I looked down and really didn’t think they would help as they were too far out. Mom then told me to push the sides of my chest together which I did and she hooked a little clear piece of plastic together in the middle and then put the bikini top on me and tied it in place. When I let go my breast stayed there. I was shocked as I had not padded it out and they were as big as any girl in my class. Mom smiled at me you look great sweetie and this worked better than I thought, you are probably close to a C-cup now. I wasn’t sure what that meant but she led me over to the mirror for a look, I was speechless. I looked totally like a girl. No sign of my male part and my chest it was huge and I had incredible amount of cleavage I was also almost naked. Grandma came it at that moment and she let out a scream, my god you look like a female swimsuit model.

It was time to go and meat Linda and her mom so my mom put some things in her tote bag and Grandma and I each grabbed a towel and we were off. All three of us looked good but mom and I were hot and I could feel the people we passed starring at us. When we got downstairs we only had to wait a few minutes for them, Linda also had on a hot pink but a different cut and style but still really sexy and her mom had on a black bikini. All of us were hot and would be turning heads all day. Linda smiled at me and held out her hands, she had long acrylic nails in the same hot pink color of her suit, she told me her and her mom had gone and got pedicures and nail this morning, I looked over and her mom also had long acrylic nails in a red color. With that the 5 of us walked out of the hotel and onto the beach, yes our hotel was right on the beach.

Now the beach was crowded but we found a nice place and they even had some beach chairs which our moms and grandma used, Grandma brought a book to read. Linda and I just put out our towels and laid down. The sun felt so warm that I kept falling asleep. After a bit Linda and I went down and played in the surf for a while before coming back and lying down again, we never really went swimming as Linda didn’t want to mess up her hair or makeup and in a way I felt the same. We had lunch about 2 and then Linda and I went down to play in the water again. We were having fun when I turned around and there were two boys standing behind us and they started talking with us and soon the 4 of us were having fun. After about an hour Linda and I went back and laid out in the sun again. It was almost 5 by now and Linda’s father would be getting off work so we were deciding what to do when the two young men came over to us. They pause for a moment and then the one finally spoke up, hey Linda and Jennifer we were wondering if you would like to go to the movies tonight, I mean we could grab dinner first. There is a theater just a couple blocks away from the beach. I wasn’t sure what to do at this point but Linda did. She smiled back, that’s sounds fun but I would have to ask my mom, then she turned to her mom and said. This is Jake and Dan we met them earlier do you think we could go to the movies tonight with then? Her mom looked the two boys up and down and then said I suppose it would be alright but they will have to pick you up at the room so your father can meet them. But we will also need to check with Jennifer’s mom. I looked at her not knowing what to do or say. She also looked at them and said, I think it would be okay for the girls to double date as long as your husband approves. Now up to this point I was just thinking or it as friends hanging out together and catching a movie but my mom’s word gave it a whole new meaning. Linda smiled back at them why don’t you give us an hour in a half, than pick us up at room 2345 at 6:30 and we can catch dinner and a movie and with that they thank our moms and said they would see us soon.

Back in the room I took a quick shower and mom helped me get ready, she did my makeup giving me a more dramatic look. My eyes were done beautifully with browns for that alluring Smokey eye look and my lips were a deep red. I looked awesome and she picked out a really pretty and maybe too sexy red dress I thought but with the way she had my breast done and a pushup bra I looked incredible and of course 4″ heels. For the first time sense I had been dressing I had the feeling this was wrong, I couldn’t go out with a boy after all I was a boy and I was not attracted to boys so I tried to explain it to my mom. She just smiled and listened. Finally she broke in, there is nothing wrong with it or you and it does not matter if you are attracted or not to him. This is part of being a pretty girl, boys will want to date you and be around you. Just think of it as being out with your friends and only let him go as far as you are comfortable. I have gone out with many men and always have a good time. They wine and dine me and treat me great and pretty much the most they get is a kiss. It doesn’t mean anything now you go and have fun. With that mom and I went up to Linda’s room to wait for the boys.

Linda had on this really hot pink dress and it was probably sexier than mine and her makeup was also perfect. I looked at her dad and I could see he was not as thrilled as her mom about the whole date and the way we looked. It wasn’t long and the boys arrived, they had on nice jeans and shirt but nothing really special but when they saw us I could tell it was not friends they were thinking of. They talked with Linda’s dad for a while and promised to have us back by midnight. With that we left and walked to a little restaurant around the corner. Jake went with Linda and Dan with me and yes they held our hands as we walked. We had a nice dinner and again I ordered a salad as did Linda. From there we went over to the movie theater and watched a movie. I actually had a good time as long as I forgot about it being a date which was hard as I kept noticing Dan looking at me plus about half way through he put his arm around my shoulder.

The movie got out about 9:40 so the boys asked he we could take a walk on the beach, before I could answer Linda said that sounded like fun so again hand in hand we went down to the beach. Now this is where being a girl gets hard as I had my little purse to carry and of course you can’t walk in the sand in 4″heels so I had to take them off so I had a purse in one hand and my heels in the other which gave Dan the chance to put his arm around me and so there we were walking down the beach that way. Now the funny thing was as strange and awkward as it was to be with a boy there was a part of me that felt safe, after all a young girl out after dark by herself is not a safe thing. Any way we walked and talked and got to know them better. They were from Seattle Washington and down here vacationing like us. Well it was almost 11:45 and we were almost back to the hotel when we stopped and almost like they had rehearsed it they turned to face us and gave us each a kiss right on the mouth. I had kind of figured they would try but didn’t expect to get caught off guard. It seemed like the kiss went forever as it was in slow motion but in reality it was probably no more than a few seconds. Then we went into the hotel. Linda smiled at me and told me she needed to use the ladies room and grabbed my hand leaving the boys standing there. When we got inside I asked her if she couldn’t wait till we got up to our rooms and she let out a laugh as I turned to her I saw her face about the same time she told me to check my makeup. Both our lipstick was smeared. I couldn’t go upstairs looking like this so we both cleaned off what was left and touched up our makeup and redid our lipstick before going out to meet the boys again who walked us up to our rooms. We both thanked them for a wonderful evening and went inside. I thought about it and it was a nice night. I had a great time and it didn’t cost me anything and I bet the boys between dinner, movie, popcorn and drinks spent at least $60 each.

Mom was waiting up for me when I got home as she wanted to know how it went. We sat and talked for a while and I told her it felt awkward to have a boy looking at me that way and I wasn’t comfortable when he held my hand or put his arm around me, I stopped short and did not mention the kiss. Mom said she understood but that boys were a part of being a girl and I would have to learn to interact with them and how to deal with them. She then gave me a hug and said, I guess the kiss goodnight also made you feel uncomfortable? I looked at her how could she have known? I looked down, he caught me off guard and I didn’t know what to do and yes it bothered me, then I looked at her and asked how she knew. She just smiled, it is the payment girls give boys for the attention they give us, for the nice evening out and for them paying for everything, it really means nothing, plus your lipstick looked as good as it did when you left which means you must have redid your lipstick recently and that was the only reason I could think of you would do that to come home. Now off to bed she told me so I went upstairs and washed off my makeup, then mom helped me remove the breast enhancers which took a little work, it is amazing how well the adhesive held and then I removed the gaff which felt so good, I looked at myself in the mirror and my breast tissue was still pulled a little in so I looked like I had small breast but my tan lines I looked like I had a white bikini on. I laid down and fell right to sleep,

Tuesday morning we all got up and mom wanted to know what I wanted to do for the day, as we were talking about it Linda and her mom came to our room. They had got some information about things you could do and just a little way down the beach they were giving Hula lessons so we all decided that would be fun so we all started getting ready. Now I was able to get the gaff on and set but I was still having a little trouble with the breast enhancers so mom helped me again and soon I was standing there in my bikini looking hot. We all walked down the beach turns out a little way down the beach is about a mile. Well we all had a blast although it took me a little longer to catch on as it seemed my hips did not want to move right but the s that was giving the lessons were great and so patient and by the end I was almost as good as the rest of the girls. We finished about 2 so we stopped and had lunch on the beach and then we just found a place to lay out for a while and relax in the sun. We got back to the hotel about 5 and went up to our rooms. I was wondering what we were doing for dinner and mom shocked me, well sweetie she said you are going to dinner with Linda and her parents as you grandma and I have dates tonight. I didn’t know what to say but mom did. You had your fun last night and your Grandma and I want to go dancing tonight and two gentleman asked us to dinner and dancing. It is just like you last night nothing serious just a nice night out. I gave my mom a kiss and told her to have a great time and for some reason I threw in to watch out for that good night kiss as it can sneak up on you. We both laughed about it. I called Linda to see what she was wearing and she said a nice dress and heels so that is what I did too.

The week went by so fast and for the most part everyday was the same on the beach in our bikinis and then the evening fancy dresses and heels we even went out with Jake and Dan again and had a good time and I was more at ease. I could tell Dan would have liked more than just a good night kiss but that was all I was willing to give and he was okay with that. Linda and I became really good friends and in a way I felt guilty about not telling her the truth about me but I just couldn’t as I was sure it would ruin our friendship plus how does one bring something like that up anyway so I just did my best to tell her the truth with that one small detail left out.

On Friday all us girls went shopping in the morning, we were at the mall and mom saw a jewelry store so we went in and looked around, mom bought me a tennis bracelet, a necklace and then she picked out a nice pair of earrings and said it was time her daughter got her ears pierced. No I was actually excited about this and picked out a couple pairs of dangly earrings and a pair of hoop earrings but mom said no it would take several weeks for my ears to heal and get use to the earrings. I could get those later. I sat down and in no time I had my ears pierced.

Saturday Linda and I spent the whole day on the beach and had a great time. The week had gone by so fast, now we were not leaving ti Monday but Linda and her parents were flying out on Sunday. I was going to be sad to see them leave but Linda and I exchanged phone numbers so we could keep in touch after all she only lives about 20 miles from me.

On Sunday after Linda had left the three of us to a ride around the Island and had a great day. I wore my bikini with a skirt wrap as did my mom. It is amazing how flexible girl’s clothes are. You can change the look so easily. This being our final night here we went out to a really nice restaurant and for the first time in a week mom let me order anything so I did get a salad and then a chicken breast. The three of us sat and talked for a couple hours, and finally mom brought up the subject I didn’t want to hear, the fact we were going home tomorrow. More specifically what would happen when I got home? Now I had figured once I got home I would go back to being David and hopefully get to dress and be Jennifer a couple times a week which mom said was one option but would be the hardest as I would be switching back and forth. She asked if I would like to stay Jennifer at least for a while maybe the summer. Now this idea did appeal to me as I really did love being Jennifer and I so loved my long nails, I had gotten so use to them it would be strange without them plus I just felt more comfortable as a girl, kind of fit in better so I told Mom I wanted to be Jennifer a little longer if I could and she smiled and told me that was fine with her.

I asked her how we could do it as it was one thing to sneak out of the house a couple times but being Jennifer all the time what would the neighbors think she just smiled at me. Sweetie I have known about your dressing for a while and I have already talked with some of the neighbors. I got this scared look on my face but mom calmed me down, don’t worry she said I didn’t tell them about your dressing. I told them one of the reasons for our Hawaii trip as you were thinking of going to College hear and you had a chance for an internship this summer and that is why we were coming. I had also told them that my niece might come stay with me for the summer as she was looking at possible moving out to California if she could find a job. So it is simple as the neighbors don’t expect you to come back with me. So when they do see you they will think you are my niece Jennifer from Oregon. I looked at mom and said you don’t have a niece at which she just laughed and then I figured it out.

That night we got back to our hotel room and as I was getting ready for bed I looked at myself. I had such a deep tan accept where my bikini was I was almost white, as I stood there mom walked in and looked at me, wow dear you really do have a wonderful tan but your tan lines those will be noticeable for a long time, probably good you will be Jennifer for a while. She gave me a kiss and said you really do like being Jennifer don’t you? I looked down and said yes, I mean I just feel right, everything about being Jennifer is right except for well except for boys. I still can’t see myself with a boy I guess I will need to go back to being a boy at some point as I do want a girlfriend.

Mom sat down with me on the bed and gave me a hug, sweetie you do not have to be a boy to have a girlfriend. There are woman that are attracted to other girls and even feminine men. What is important is for you to be happy, find what you want in life and if you want to be Jennifer, if you want to be a boy who dresses as a girl, a boy who lives as a girl or even if you want to become a girl that is what is important. I gave her a big hug and told her I wanted to try to live as a girl to be Jennifer but I didn’t think I wanted to have any surgeries. Well then I guess I have a daughter now, when we get home as far as anyone knows David is living in Hawaii and going to school and my niece Jennifer is staying with me for a while.

With that I got into bed to go to sleep, I could stop thinking about what I had just decided to do, was I crazy, I was going to live as a girl for who knows how long. I finally fell asleep and I had such wonderful dreams all night. Monday morning we all got up and got ready for our trip home and my new adventure. Even Grandma was supportive of my choice and she said she looked forward to spending time with me. The flight home was a relaxing one, mom was working but Grandma and I sat together and talked. Grandma told me her and mom talked last night and when we get back I was going to stay at her place for a few days that way mom would go home by herself and then on Friday I would go over so the neighbors would think was just her niece showing up which sounded good to me as I was still a little scared about this. By the time we got home it was after 7 so we grabbed dinner and then mom took me and Grandma to her apartment so I could start my new life as Jennifer.
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My Grandma   2 comments

My Grandma

By Elisabeth James

Well I guess I should start with a little about me. My name is David Johnson and I am 18 years old and live with my mom. My mom is beautiful and works as a flight attendant for a major airline. She is 5’4″ tall and looks like a model and yes she is only 35 years old as she had me at a young age and my father I have never met as he didn’t want anything to do with us. We live in Southern California and the only other family we have close is my Grandma who is 55 and lives just a couple miles away. She retired from the city of LA after 31 years, she would have kept working but her eye sight got too bad that she doesn’t even drive any more. She lives in an assisted homes but she really loves it there. Mom and I live in an older house mom bought years ago.

Well as I said I am 18 and for a boy I am shall we say on the small side, I guess I took after my mom as I am also 5’4″ tall but weigh a little more than she does. Oh I guess there is one more thing, I like to cross-dress. I actually started playing with her makeup when I was about 10 or 11 and this confused me, not enough to talk about it as I have never told anyone. When I turned 15 for some reason one day when she was gone I snuck into her closet and tried on one of her dresses as we were the same size and for some reason I liked it, the way it felt and looked. Now being young and having these feelings is confusing as I knew I wasn’t gay as I never looked at the other boys in my class just the girls but it was more than just how pretty they were and that attraction you feel but it was also about how they looked, the clothes and makeup, I loved everything about girls. I tried to stop a few times but couldn’t and so that was my secret life. Now it was popular for boys to grow their hair out which I did and wore in a ponytail and maybe mine was a little longer than most but when I did get the chance to dress up I could make my hair look feminine. It is funny as there is a girl in my class I really like named Jill and so I try to make my hair look like hers.

Now there is good and bad things about this as there are with everything. Having this secret life I kept more to myself but this also allowed me to get really good grades. So by the time I was Senior in High school I had pretty much everything I needed for Graduation so I didn’t have to go to school on Wednesdays and Fridays were a half day for me. Now my mom had a great schedule as a flight attendant. On Monday and Tuesday she would fly from LA to Seattle and back which was about a 7 hour day, Wednesday she would fly from LA to Honolulu which was her long day about 12 hours and Thursday and Friday she would fly to San Francisco whish was only about a 5 hour day plus once or twice a month she would get a Friday flight to Japan which meant she would come back on Saturday and as I was in High school she would let me stay by myself. Wednesday became my day to dress as I was home all alone for the whole day as mom would leave the house about 7 am and not get home till around 8 at night.

Now as I said I am small for a boy and over the years I had gotten really good at makeup and dressing up and I really don’t think anyone would recognize me or for that matter be able to tell I was not actually a girl but I could never work up the courage to leave the house for fear someone would see me. Well it was just before Halloween of my Senior year when one of my mom’s best friends came over it turned out her husband had gotten transferred to Japan for a couple years, he was in the military and she asked mom if she could keep her car at our house while they were gone as she didn’t want to sell it and mom said okay. She told us we could use it if we would take care of it and run it once a week so it just didn’t sit there. I volunteered to drive it once a week for her. Now our house is an older one and both mom and I park our cars on the street in front, yes my mom got me a car for my 16th birthday. Behind our house is a little ally way and there is a drive behind with a little carport. The problem with this is you have to go out the front door and then around to the back so it was just easier and closer to park on the street in front so that is where we put her car. So I would drive her car once a week. Well it was late November on a Wednesday and I was all dressed up and looking great when the idea popped into my head to take her car for a drive.

Now as I said our house was older with a big front porch that really wasn’t visible except from the street right in front and I could go off the side of the porch and only have about 15 feet that people could see me before I went between the houses to the back and with the hedge along the side the chances of someone seeing me was very small. Now I spent a good hour working up the courage. A couple time I went out on the porch and then back inside. I just had to do this and so it was about 2:30 in the afternoon before I finally did it. I looked to see if anyone was out front and saw nothing so down the side steps to the side walk and across the front to the side. Now I was wearing a short skirt and heels so I couldn’t really move fast and once I started I never looked back as I wanted to get to the cars as fast as I could. Now the car had tinted windows so you really couldn’t get a good look inside so I felt safe plus because this was not my car no one should recognize me.

I drove around for about 45 minutes and never did work up the courage to stop any place or get out of the car. Once back home I did just the opposite. Parked the car and walked back to the front of the house and looked to see if I could see anyone and when it was clear across and up the side steps to the safety of the porch. Now I must say I do wear a lot of my mom’s clothes but I have also managed to buy some of my own and also makeup and shoes. One of the cool things with the internet is you can buy online and you can even schedule when you want them delivered so I was getting a nice little wardrobe. I so looked forward to Wednesdays there were times I might go out for a drive two or three times on a Wednesday but still could not get up the courage to get out of the car.

Now for Christmas my mom and Grandma gave me gift cards which I used online to buy several pretty dresses, heels and makeup so I was so excited so I was really looking forward to the first Wednesday in January as my mom had taken the week off work between Christmas and New Year’s which would mean I could not dress up.

Well the Wednesday finally came and mom left and I got all dressed up in this really cute white skirt and pink top and 4″heels. I grabbed my purse and out the door I went. I was getting pretty bold at this by now. Looked and it was clear so around to the car and off I went for about an hour before coming back for my lunch. It was so much fun.

Well after lunch I was ready to go for another drive so I touched up my makeup and out the door I went. I was just to the corner of the house when I realized I had left my cell phone so I turned around and went back and up on the porch. I was fumbling in my purse for my keys when I heard a vice behind me. I was scared to death as I turned around and saw my Grandma standing there. She said hi and asked what I was doing, now I know she has bad eye sight so I mustered my best female voice and squeaked out that I was here to see David, she smiled and said oh you must be one of David’s friends which I replied yes. She smiled again and said she was also here to see her grandson. I didn’t know what to do so I stood there as she knocked on the door and for a moment I was scared the door would open even though I knew no one was home. Well after few minutes she smiled at me and said looks like he is not home. I smiled and said yes looks that way still not knowing what to do. Grandma smiled at me again and said she would ell David I stopped by and asked me what my name was. I was at a loss as I had never thought about a name and before I could stop myself I said Jennifer. She smiled again and said what a pretty name for a pretty girl and with that she said we should go. I smiled and said I had parked out behind so I left my Grandma standing there and walked back around the house to the car as my Grandma walked back to the taxi.

I left and took a short drive maybe 15 minutes as I was still shaking for the encounter so I went back home. I carefully looked around before going to the porch and quickly inside. I put my purse down and there was a call from my Grandma, she still does not have a cell phone so she had to wait till she got home to call me. The message just said she had stopped by to see how I was and had wanted to know if I wanted to go to dinner with her tonight and also that a friend of mine had stopped by to see me Jennifer.

I calmed down and gave her a call as I wanted to see if she had any suspicions and she seemed like everything was okay so I agreed to have dinner with her so I quickly cleaned up and got myself back to my male looking self as I had had enough for the day. I went over and picked her up at 4 and we went to a restaurant just down the street. We had a nice dinner and Grandma never brought up earlier today till the end when she asked me I Jennifer was my girlfriend, I almost choked and said no there was another girl I liked named Jill which was true. Grandma just smiled and said to bad we would make a cute couple beside she said I think Jennifer likes you from the way she was acting. I didn’t know what to say so I just nodded. Well that night I did a lot of thinking and decided that I was all done dressing up as this was to close a call.

The thing was by Saturday I was thinking about dressing again and come the following Wednesday I couldn’t help myself and soon I found myself all dressed up again and out ten door I went for my drive. I actually went out 3 times for a drive this day and had such a good time. I actually stopped at a store and thought about going in but just couldn’t work up the courage part of it was the fact I was wearing 4″ heels and although some girls my age do wear them and go shopping it still would draw attention to myself so after sitting in the car for 30 minutes I drove back home.

It was now the end of January and it had been 4 weeks since that fateful day I had run into my Grandma and I got all dressed up in a nice black dress of my mom’s, did my hair and makeup and put my 4″ heels on and out the door for my drive. I looked really good and had a great time but still too scared to get out of the car. I got back home about 11 am and came around the corner of the house and as I did I saw the cab out front and stopped as I looked up and saw my Grandma on the front porch at the door. I was just about to turn when she saw me and said oh Hi, Jennifer isn’t it. There was nothing I could do so I said yes and walked up to the porch as I didn’t want to be standing in the front yard, I told her I just stopped by to see if David was home as I knew we would knock on the door and no one would be there and then I could leave and not look suspicious. Grandma looked at me and told me how pretty I looked and we chatted for a second while we waited. She asked me if I liked David and I thought quickly and said yes but he likes another girl named Jill. After I said this I realized this might have been a mistake as I should not give too much information.

Well grandma said looks like he is not home and I said yes it looks that way. She smiled at me and said I came over to take him to lunch and now I guess I will have to go by myself. I smiled and told her I was sure he would be sad he missed her and again thought to much keep quiet. Grandma smiled at me I know why don’t we do lunch, I so hate eating alone. I didn’t know what to say, I couldn’t go out to lunch with my Grandma and as I was thinking of an excuse she took my arm and we started towards the street where the cab was waiting for her. I told her I wasn’t sure I should leave my car out back but she just said it would be fine and by now we were out at the street. I was about to say no when I saw one of the neighbors doors open so I got in the cab quickly to hide and now there was nothing I could do. We were off to lunch. The cab driver really paid no attention to me but I was so scared.

We got to the restaurant and Grandma told the cab drive to be back in an hour and a half. Now I had to get up the courage to get out and I knew there was no choice as if I didn’t it would look strange and Grandma might figure it out so there I stood on the street with her and in we walked. Now as scared as I was I also found it exciting and such an incredible feeling. We were shown to our table and sat down. Now I had to think about what to eat as I wanted to do my best to act like a proper young lady so I chose a house salad. Now Grandma started off with small talk mostly she talked about her grandson David which was me if she only knew. This made it easier but after about 30 minutes she got around to asking me questions, how well did I know David did we have many of the same classes. Now as strange as this was it was actually easy to answer the questions as I knew everything about David and the school and his friends. Now I was so focused on Grandma that I had forgot about being out in public and actually had a great time. We finished lunch and Grandma paid and we went out and waited for the cab which showed up right on time. She had the cab drive down the ally way and stopped in front of the car in the car port so I didn’t have to walk around the house which was nice in some ways but it also meant I had to get in the car and drive away. With the hour I was gone before I ran into Grandma, the two hours we were gone over lunch and now this it would be the longest I had been out.

Grandma smiled at me and said, I had a great time Jennifer, it was nice to get to know you. I smiled back as it really had been an incredible day so far and I am sure it showed, I told her I had a great time also and it was great getting to know her also. That is when Grandma caught me off guard, she smiled and said Well Jennifer why don’t we do lunch next week, is Wednesday good for you? I was so caught up in the moment I said yes before I realized what I had said. Grandma gave me her phone number and address and said I should pick her up at 11 am next Wednesday and we would do lunch again. With that I got in the car and drove off and drove around for about 20 minutes before heading back home. This led to another problem, I couldn’t give Grandma my phone number as Jennifer as she already had it for David and I wasn’t sure if she had caller ID on her phone I had to do something. Now mom had a work cell phone so I had my own plan and mom gave me the money to pay for it she thought that if I had to pay the bill even with her money it would teach me responsibility so I cleaned up and ran to the mall to see what I could do. Well it turned out for only $20 a month I could add a second phone to my account so that is what I did.

Well later that night before Mom got home Grandma called me and told me about her day and having lunch with Jennifer and hoped I could join them, I had to think quick and told her I couldn’t as I had to be at school at that time for study hall and that seemed to satisfy her. Now as soon as I hung up I called from my new number, Jennifer’s number and thanked her for lunch and gave her the phone number so she could call me in hopes this would make it harder for her to figure out her grandson and Jennifer were one in the same. We talked for about 10 minutes and I told her I would pick her up next Wednesday for lunch.

Now next Wednesday came and I was really excited and looking forward to it as it was fun last week to be out in public especially as I was not by myself. But as I was getting ready I really got scared. I picked a grey skirt of my mom’s with a cream top and only 3″ heels this week as last week I had felt I was a little over the top going out. My makeup was also not as heavy as last week a little more shall we say day time look. I grabbed my purse and stood at the door wondering if I should really do this, go out to lunch again with my Grandma. I finally decided to go for it as I knew her eye sight was not that great and I could pull it off so I gave her a quick call and told her I was on my way and would be there in about 10 minutes. As I pulled in it hit me I have come here many times as David I could not walk in like this as I was sure someone would recognize me but as I pull to the front there was Grandma standing by the door waiting for me so I was safe.

This time Grandma said she knew a really nice café and told me where to go. We actually drove about 20 miles into LA and ended up at the mall and went to the a café at Nordstrom’s which had really nice food but it also meant walking into Nordstrom’s and to the front of the store by the mall and there were so many people around. Now I knew that no one could tell I was not a girl from my size and look it would be more the way I acted or if I ran into someone I actually new but I was still scared. We had a nice lunch and talked and Grandma told me more about her which of course I already knew but I didn’t let on as I needed her to think of me a Jennifer a girl she didn’t know.

After lunch Grandma said as long as we are here we should do some shopping. Now I got that scared excited feeling again. I couldn’t walk around the mall like this could I? I smiled at Grandma and told her I was sorry but I didn’t have money to shop at which she just smile and told me you can shop without money and off we went into the mall. Now as I said most of my stuff is my mom’s and what I have managed to buy online but shopping in person is a whole other experience. We hit several shoe stores and a few clothing stores and we both tried on some dresses, as I said this is my Grandma but she is only 55 and doesn’t look that old. The last store had some really cute dresses and grandma found a couple she really liked, as she said she needed something pretty to wear when we went to lunch as I always looked so pretty. As she was handing them to the sales girl to ring up she also handed her 3 of the dresses I had tried on and like. I told her she shouldn’t buy them for me and she just smiled at me and said, please let me do this for you. My daughter is all grown up now and I only have a grandson, I really enjoyed spending time with you today it was almost like having a granddaughter for the day. This made me feel so nice I just gave her a hug and said yes.

On the way out we stopped at the MAC counter at Nordstrom’s and we both got a makeover. Now this really scared me as the lady there removed all my makeup and started fresh. I thought she would for sure figure it out but she didn’t. She just redid my makeup and told me what all she was doing and why and how I should do things to enhance my face more as she said I had great eyes and lips and in the end she really did make me look better so again Grandma bought some makeup here for us both. I was a little shocked as Grandma had probably spent $250 on me today which made me feel uneasy but she seemed really happy so I let it go. I drove her back to her place and dropped her off and then went home it was almost 6:15 when I got home so I quickly ran upstairs and showered and hid my new dresses and makeup. And put mom’s skirt and top back. It really was an incredible day for me.

Over the next few weeks I found I talked with Grandma a lot more as she was calling me as David and Jennifer, I really had to work hard to keep the two straight and not mix up conversations. I also started having lunch with her on Friday’s as David and Wednesday Jennifer would have lunch with her and we always did a little shopping and she would always by me some cute outfit but I really worked on not letting her spend too much money on me as I didn’t want to take advantage of her as I was just so happy going out with her as Jennifer. Because of this we became really close. Now there were those awkward moments when she would ask David why he didn’t date Jennifer or ask Jennifer why she didn’t peruse David more or even worse when she would ask me if there were any boys I liked or if I was seeing anyone. These are always hard questions to answer and that ad my little situation into the mix.

Things were going great and I had a great life. I loved my time as Jennifer and I wish I could spend more time this way. Now I don’t want to have surgery and become a girl but I do feel so right as Jennifer. It was amazing how fast the weeks went by and how comfortable I had become as Jennifer. On the weeks that my mom flew to Japan and come back late on Saturday I started going out on Saturday mornings as Jennifer and even went shopping on my own. I even met a couple girls at the mall one day and we hung out shopping for a few hours. I seemed to fit in so well and at the end of the day we exchanged phone numbers and yes I did give them the one for Jennifer.

By the end of March I was still doing my Wednesday lunch and shopping with Grandma and twice a month when mom went to Japan after David had lunch with Grandma I would rush home and get all dressed up and then go out to dinner and the movies with Sue, Melissa and Amy the three girls I met from the mall. We actually became good friends and it became hard to balance all the things. Only being able to get together with them a few times a month made it hard but I told them I had to help take care of my Grandma and they seemed okay with that but we still talked on the phone all the time and it wasn’t long before Jennifer’s phone was used way more than David’s phone. It also was nice to have friends as David had really kept to himself. It is strange that I had to be a girl to make friends

It was the end of May and I was really looking forward to summer vacation as I would be out of school and able to be Jennifer almost every day. I just had one hurdle to get past. With mom’s busy schedule her and Grandma didn’t talk much but after school got out the three of us were going on vacation. Mom had arranged a week in Hawaii, I would graduate on Sunday June 6th then on Monday and Tuesday that week I would have to go into school to finish up some things, turn in books, clean out my locker and of course a few parties in some of the classes and then I would be done for the summer. Now that Friday June 11th mom would fly to Japan and come back Saturday early evening. On Sunday morning she would do the flight to Hawaii and Grandma and I would fly along, working for the airlines we got to fly for free. Mom had booked a hotel room right on the beach for Sunday night through the following Sunday night and we would come back on Monday, mom working the flight home so we would be there for eight night. This would mean not being Jennifer for all those days could I do it. The other two things that bothered me is this. Spending this much time with Grandma would she notice something? And with her and mom spending that much time together would Grandma bring up Jennifer and then mom ask me a bunch of questions I really don’t want to talk about. I was getting nervous but once I got through this week I would be able to be Jennifer every day during the week. Plus I was actually looking forward to Hawaii as I have never been there before. Now my plan for the week was of course was Jennifer would have lunch with grandma on Wednesday, David would skip lunch with her on Friday and end the day with Sue, Melissa and Amy and on Saturday I would spend it getting ready for the trip.

Wednesday came and I wore one of the Dresses Grandma had bought me and of course a pair of 4″ heels for our lunch date, Grandma was also in a dress as she had really started to dress well I won’t say better but she did wear dresses every time her and Jennifer went out, I guess Jennifer really did have an impact on her life she actually looked younger. I picked up Grandma and we went off to lunch and then some shopping, it was a great day but I could tell something was on Grandma’s mind, when I asked Grandma just smiled, you know I am going on vacation with my daughter and grandson next week. I took a deep breath wondering where she was going with this. She just smiled, I thought maybe we could get together Saturday morning and have some fun I have a wonderful day planed but I would need to be home by 4 so I could pack for the trip. Now I know I said I wasn’t going to do anything on Saturday but get ready but the fact I would go 9 days with no Jennifer I thought why not. She wanted to be home by 4 so I would be home and cleaned up by 5 in plenty of time to get packed and ready before mom got home so I agreed.

Friday came and Sue, Melissa, Amy and I spent all day at the mall looking around and having fun and even went to a movie that night. It was a great girl’s night out. Most of the day they were looking for things for my trip including a bikini, I just kept telling them that I had already bought everything I needed. They made me promise to send them some pictures from Hawaii which I wasn’t sure how I would do, I guess I could send them pictures I just wouldn’t be in any of them. Well after the movie I went home and to bed as I was picking Grandma up at 8:30 which would mean being up by 6:30 to get ready. I love being Jennifer but she does take more time getting ready. I reasoned it would be okay if I was a little tired as I would be in bed early Saturday night and on Sunday I could sleep on the plane if I was still tired.

Saturday morning I got up and ready again a cute skirt and top and heels, all of which were my clothes. I hadn’t realized it but over the last several months between what Grandma had bought me and I had bought myself I had quite the girls wardrobe, probably 20 skirts, 25 dresses, 15 Capri’s, 6 pairs of shorts and a whole suitcase full of bras and panties not to mention 2 dozen shoes. I had so much stuff hid under my bed I was so scared mom would find it but when you are buying it you never think of that all you see is how cute it is. Well I went and picked up Grandma and we went out for breakfast.

We were having a wonderful breakfast and Gram was telling me how excited she was to be going to Hawaii as it has been over 10 years since she was there last. I almost slipped a couple times as I was actually excited about it too. Well as we finished breakfast Grandma told me she had scheduled an appointment at the beauty parlor for her and me as she wanted to get ready for the trip and she wanted to share the experience with me as she missed doing things like this with her daughter, Mom was just so busy. Now I know I should have said no but the thought of being in a beauty parlor fascinated me. I remember when we got the makeover at Nordstrom’s and how fun it was so I agreed and off we went. I asked her what we were going to do and she smiled, you will love it, we will get our hair washed and set, a manicure and pedicure and then a facial and makeup. We will look like a million dollars afterwards. Now I figures what is the harm as I have nail polish remover at home.

We got to the beauty parlor at 10 and went in and the ladies were ready for us. They put us in a big chair and leaned us back and then washed and messaged our hair and scalp. It was so relaxing and Grandma and I just sat there and enjoyed it. I can see why girls love this so much. They conditioned our hair and washed again and then wrapped them up in curlers. Now I have done this many times at home when I get ready and as my hair is now down past my shoulders when it is not in a ponytail it looks very feminine anyway. Now with our hair wrapped up we were moved over to a chair and sat down and they gave us our facials again so relaxing and my skin never felt better.

From here we went over to these chair that had little tubs for our feet and we soaked our feet in the water. Grandma had picked out this really pretty bright red nail polish for us to wear, it really was pretty and it was almost a shame I would have to take it off when I got home but I was going to enjoy it for now. Soon our feet were done and I had beautiful red toe nails. We were then led back over to the manicure tables and sat down. The lady came over and told us to lean back for our mud mask, now this was a funny feeling as they put this stuff on our face that felt kind of slimy but soon started to harden and of course we had to keep our eyes closed and they even put cucumbers on our eyes. I have seen this in movies but I thought that was all it was but Grandma said it would keep our eyes moisturized during the mud mask and keep the puffiness down around our eyes so her we sat in darkness talking between ourselves and of course the nail technicians. This was turning into the best day of my life. It took about an hour on our nails and by then my face was so tight from the mud mask. They leaned me back in the chair and gently washed off the mud mask and dried my face. This was followed my more creams and something warm around my eyes. I felt her press down and rub above my eyes and then she pulled and I felt this horrible pain on my eyebrows. I suddenly realized they had just waxed my eyebrows. I was in trouble now. I wanted to scream but I couldn’t as Grandma would know but then she would notice the eyebrows tomorrow what was I going to do. I grabbed hold of the arms on the chair but something felt different. I looked down and I had long red nails, they were a ½ inch long with square tips and very feminine. I had been given acrylic nails. This had gone for bad to worse. I didn’t know much about acrylic nails other than they were hard to get off. I guess I could cut them short and try to pry them off but what about my eyebrows, how bad were they.

They leaned the chair up and I could see the eyebrows they were a very feminine arch and mom and Grandma would notice. As I was staring at them they took the curlers out of my hair which use to be a light brown but was more of a blonde now. I didn’t know what to do I wanted to cry but couldn’t I was too scared. My secret would be found out soon and mom would be so mad and Grandma I have been deceiving her for the last several months. My world was crashing down and there was nothing I could do. I had to find a way out and so I looked at Grandma and told her and the beauty technician that I needed my hair color back the way it was and the nails off as my mom did not think a girl should change herself like this, I knew there was nothing I could do about the eyebrows. The beauty technician told me I looked great and she thought for sure my mom would be okay with it but that if I really wanted to they could remove the nails and recolor my hair back to the way it was this made me feel better as all I had to do is figure out the eyebrows and right now I was thinking of just shaving them off and telling mom I tried to trim them and messed up that would work.

Grandma leaned over and smiled I am sure your mom won’t mind as you look great Jennifer. Besides you, your mom and I are going to have so much fun in Hawaii next week we just really wanted you to look good for the trip. I was in shock and didn’t know what to say, she knew, somehow she knew I was David her grandson. I wanted to ask but I knew that would sound funny in front of everyone here. The beauty technician looked at me and asked what I wanted and I just told her I was fine how I was. Grandma paid the bill and we walked out to the car in silence as I waited for her to let me have it but she never did. I drove in silence till I could take it no more and pulled over to the side of the street. I looked at Grandma and told her I was sorry for misleading her and for dressing this way and she just gentle took my hand and told me it was okay she wasn’t mad. I looked at her again, I have to ask I said, when did you figure it how what was it that gave me away. Grandma almost broke into laughter and then said. Sweetie you are my grandson, my flesh and blood. You don’t think I could tell who you are, I knew the first day I met you on the porch why do you think I waited for you that Wednesday and invited you to lunch. I just looked down, I thought with our eyesight you wouldn’t figure it out. Grandma lifted my chin up and said, my sweet child I had my eyesight fixed over a year ago. I just looked at her but you live in an assisted living apartment and you don’t drive. She smiled, I don’t like to drive and with where I live I can get everything by walking or a taxi and it is cheaper than owning a car and paying upkeep, insurance and gas and I live where I do because it is close to you and your mom, I have good friends there and I don’t have to do anything I can come and go as I like with no responsibilities. Now why don’t we go to my place and get my stuff and then go back to your home and get you packed for the trip.

I looked at her and started to tear up, but what about mom what will she say. Grandma smiled at me, I won’t lie to you your mom is upset with you but not for what you think. She is upset because you didn’t tell her how you felt and kept this a secret, she is also upset that she hasn’t had time to spend with her daughter and do the mother daughter things but that will all be fixed while we are on vacation in Hawaii. She is really looking forward to spending time with you like I have and getting to know this side of you. I looked at Grandma, you mean I am going on the vacation this way as Jennifer. Grandma gave me a hug, yes sweetie if that is what you want, both your mom and I would love to have Jennifer there for the week but it is your decision and you need to make it quick. We can remove the nails tonight and straighten out your hair and we can figure out something for your eyebrows but we both hoped Jennifer would go. I gave Grandma a big hug and a kiss and told her Jenifer would love to go to Hawaii. That is when I noticed the lipstick I left on her cheek and realized what I was about to do.

We got home and Grandma helped me unpack all my boy clothes and pick out the clothes Jennifer would need, the funny thing is I went from one suitcase to two and still had trouble fitting it all in. now it was just a matter of waiting for my mom to get home and as I waited I got more and more scared wondering what she would think of her son and how she would treat me.

My Grandma Part 2

Grandma’s special gift   2 comments

Grandma’s special gift.

By Elisabeth James

Well my name is Kelly Frost and I have had an interesting life. My parents are both very successful and work at Microsoft and as such we live in a big beautiful house in Seattle, actually it is bigger than we need as it has 5 bedrooms upstairs a master bedroom and then two pairs of bedroom each which share a bathroom with the room next to it like in the TV show the Brady Bunch. Well enough about that so let me tell you a little about me.

I am 16 years old and very small for a boy my age, actually I stopped growing at age 11, and I am only 5’4″ tall and weigh about 115. My story really starts when I was 7, I loved to watch my mom put on her makeup there was just something special about it, she looked so pretty. I guess I was jealous, I knew boys were not supposed to be pretty but I couldn’t help myself. Anyway when I could I would sneak a tube of lipstick or some eye shadow to play with. I thought there was something wrong with me but I couldn’t help myself. I think it was when I was 9 I started putting on some of my mom’s clothes that I could somewhat fit in. this is about the time I started growing my hair out as lots of boys my age had long hair. Now I am not saying I wanted to be a girl I just loved everything about them and the way they looked.

Any way when I was 9 I also got my first computer for the start of the school year and it was the best gift I had ever got as I was able to go online and I found Facebook and all kinds of boys just like me from my age up that like to dress as girls, well it didn’t take long for me to set up a Facebook account so I could chat with them and suddenly I wasn’t alone. Now with a name like Kelly I didn’t think to change my name so this would mean I could set up a Facebook page for my boy self but that was okay. It was great to talk with others and know I was not alone. I even put a couple pictures online when I had on mom’s dress and some makeup but nothing you could clearly see my face. Then other good thing about the computer was I was able to send e-mails and now I could e-mail my Grandma who lived in Portland. My Grandma was really well off, I mean she lived in a bigger house then we did and traveled all the time which meant I really didn’t get to see her very much at best once a year so this was a way I could keep in touch. Now she was really nice but she was also a little eccentric at least that is what my mom and dad called it but I guess when you get older you can do what you want.

Well I was shocked when my Grandma said she was coming to our house for Thanksgiving but I was really looking forward to it as it had been over a year since I had seen her. I was really excited and my parents just told me to be on my best behavior and not do anything to make her made. Any way we picked Grandma up at the airport on Wednesday night and she gave me a big hug and said how happy she was to see her granddaughter which caught me off guard, mom just said it was because of my long hair. Any way when we got home Grandma had little gifts for all of us and when she got to me she handed me a couple small boxes and to my surprise inside were two dresses, she gave me a big hug and told me it was time I stopped being such a tom boy and how cute I would look in them. Mom and dad both told her I was a boy but she just smiled and told them she knew how they had wanted a boy but it was time I started dressing like a girl. Mom gave me a hug and apologized and told me Grandma had a little trouble with reality and they would make it up to me so I thanked Grandma and gave her a big hug. Now deep down inside I was thrilled with the dresses as now I had my own in my size.

When Grandma left both mom and dad told me how sorry they were about the dresses and they would fix it. I told them thanks and I understood about grandma. Mom was going to get rid of the dresses so I had to think quickly. Mom why don’t we put them in the next room just in case Grandma comes back we wouldn’t want her to think I just got rid of them, mom thought that was a great idea and so did I as I could get into that room anytime I wanted through the bathroom.

Now it was getting close to Christmas and we received several boxes from grandma, one for mom, one for dad and 3 for me I was shocked as grandma had always sent gifts but this year she really went overboard. I couldn’t wait for Christmas day. Well it finally got there and I got so many great gifts from my mom and dad and even Santa and then it came to the boxes from grandma. I opened the card and I saw right away it said to her special granddaughter on Christmas so my hopes were high she would send me something pretty I just had to not act to excited. I opened the first box and sure enough it had not one but 5 pretty dresses in it I got to the second box and when I opened it I didn’t have to act shocked as I was. Grandma had sent me an assortment of bras and panties and a few nighties in such pretty colors I looked at mom and dad and they were just as shocked as I was but probably for a different reason. The third box had several pairs of shoes all with heels ranging from 1″ to 4″ which I loved but for someone my age probably a little more grown up then I was and also a makeup set. I looked at mom, she gave me a hug and told me they would make it up to me. I picked up the boxes and mom asked me what I was doing. I just smiles and told her I was going to go put them in the spare bedroom so when Grandma came she could see them. She gave me a hug and told me what a wonderful child I was to care so much about grandma.

That night I could control myself so I went to bed early, mom and dad thought it was because I was disappointed and they promised to make it up to me. I snuck into the other room and got a bra, panty, dress and makeup and soon I was all dressed up and looked better than I had ever. I took a couple pictures and posted them on my Facebook page and this time you could see my face not that anyone would recognize me. I soon got comments from some of my friends which I now had over 200 and all of them told me how cute I looked. I told them all about the presents I got from grandma and they said how lucky I was which I new. Now as I said by this age I had stopped growing so I was now happy about that as I would outgrow these wonderful gifts.

Well as I said I loved this and Grandma started coming around more, Easter, My Birthday in June, Thanksgiving and Christmas and she always bought me cute dresses, shoes and girl things and mom and dad just gave up trying to convince her I was her grandson and thanked me for being so understanding of a grandma. Well it was Easter when I was 14 when Grandma showed up with this really pretty pink Easter dress for me and I thanked her for it and gave her a big hug. Any way it was about an hour before dinner when Grandma said we should all get dressed up for dinner today, she looked at me and told me to go put on my new dress. Now she had bought me many things over the last few years but she had never asked me to wear them. When she came I would stay in the spare room with all her stuff and that had always been enough. I looked at mom and I could see the look on her and dad’s face and I could tell they were about to say something when I realized I had to say something or risk an end to it all. I walked over to mom and said well we normally don’t dress up but if mom dad thought it was a good idea I would agree. Mom gave me a big hug and said she would help me. On the way upstairs she thanked me for being so understanding, I just smiled and said for one day I could do it. We got into the room and I was getting the dress when mom sat me down, sweetie it is so nice of you to do this but I am afraid you will also have to wear the underwear as she held up a pink bra and panty. My heart almost stopped as this was too wonderful. I did my best to hide my excitement and told her for grandma I would. Soon I was standing there wearing a bra, panty, and a beautiful pink dress and of course some low heels. I was in heaven. We went outside, dad gave me a hug and told me he knew how hard this was on me but thanked me for putting grandma first. Grandma’s eyes lit up when she saw me and she gave me a hug and told me what a beautiful girl I was and it was a shame I didn’t dress this way more. Grandma also had on a beautiful dress that almost match mine in color. Mom and dad went upstairs to change and grandma too me back into the room. She sat me down and told me I was old enough to wear a little makeup. With that she put on some eye shadow, mascara and a pretty pink lipstick. I was in shock, what would mom and dad say. When they came out they saw us in the bedroom and saw me, I just smiled and told them Grandma thought I was old enough. We all went down stairs and on the way down mom gave me a hug and promised to make this up to me and how proud she was I was thinking of grandma first.

We had a wonderful Thanksgiving and it was the most wonderful day of my life but I couldn’t tell mom that. I did not want the day to end and I did everything I could to keep from changing but soon it was 10 pm and time for me to go to bed. Mom and grandma came upstairs to help me and grandma picked out one of the nighties she had given me to sleep in. from then on whenever Grandma would come I would wear a dress and pretend I was her granddaughter and my parents would always reward me afterwards for being so thoughtful. It was the perfect life and I so looked forward to Grandma’s visits which seemed to increase. Seems as she got older she cut down on her traveling an d as such would come visit us about every 6 weeks which gave me a lot of time to be a girl. Grandma even took pictures which she would send me copies through e-mail and I would post to my Facebook page. She even taught me how to put on makeup. Even a few times mom would come in while she was showing me and give me tips. It was really so much fun. I even got pretty good at it.

By the time I was 15 I was pretty good at dressing up so much so that when we knew Grandma was coming over I would get dressed up before she arrived, mom would even help me maybe with my hair or makeup and we would pick out the outfit I was to wear which was getting harder as my wardrobe had really grown as Grandma always had something new for me when she came. I think we all got used to it as mom and dad no longer shall we say made it up to me which was okay as I totally enjoyed my girl time, it became the new normal when grandma was here although we never went out which is something I really wanted to do now but that was okay as I got time to dress and I had my friends online I could video chat with while I was dressed up and I had posted so many pictures to my Facebook account. I would chat with some of my friends online that were older about what it was like to go out and I had several friends that were real girls and we would chat about what it was like to go to the beauty salon and get your hair done or a nail salon and get your nails done and it always sounded so much fun. I new someday I would get the chance to go out. Or what it would be like to live for a week or more as a girl to do this every day.

Well it was my 16 birthday on June 21st which fell on a Saturday and Grandma was coming to town for it. My Parents told me we would go out and celebrate after grandma left so I was happy as I would get to spend my birthday as a girl this year. Grandma arrived on Thursday night so while dad was at the airport picking her up mom and I were at home getting her granddaughter ready. By the time they arrived home I looked so beautiful and so much like a girl no one would ever be able to tell and I could see in my mom’s eyes she was proud of the way I looked.

Grandma’s eyes lit up when she saw me and she gave me a big hug and told me how pretty I was and how lucky she was to have such a beautiful granddaughter. Even dad told me I looked pretty and gave me a kiss on the cheek. Grandma had a few presents for me but she told me I had to wait till Saturday, my birthday to open them but maybe if I was good I could have one present tomorrow which was Friday. Mom and dad both had to work so it would be Grandma and me at home all day alone and I hoped she had something special to give me.

Grandma smiled Kelly my dear lets go out and have some fun today maybe some shopping or something. Now I knew I should have said no as I have never gone outside like this but I so wanted to. How much fun would that be? I gave her a hug and told her that sounded like so much fun. She smiled and told me to go put my ID, some money and makeup in my purse as the cab would be here shortly. I was shocked she had already arranged for a cab.

By the time I got back downstairs the cab was there and so I took my first steps outside. Now we did have a big house which also meant a big yard and long drive so I really didn’t have to worry about the neighbors seeing me which made it a lot easier. Soon we were on our way. We got to the mall and the cab left us off at one end and grandma and I walked to the door and inside and I past several people and none of them pointed at me or laughed, a couple boys did take a good look the way I do when a pretty girl goes by. Just inside the door was a beauty parlor and grandma headed inside. I paused for a moment and grandma smiled at me and said, honey you are 16 now you need to take better care of your hair and nails now so I went in. we were greeted at the door and I found out Grandma had made an appointment for us both.

We started off with our hair, first a wash and then cut just a little off the ends then some conditioning and then another rinse and then my hair was set up in curlers. Now I had played with my mom’s curling iron at home but this was a first. Once our hair was set we were led over to these chairs where they soak your feet and give you a pedicure. Oh this was so relaxing and I was enjoying every minute. It was everything I had hoped it would be. When they were done she asked me what color I wanted. Now I have played with makeup but never nail polish I looked at grandma and she smiled and told me any color I liked so I picked out this bright red color which grandma liked too so we both got our toes painted that color. They looked so beautiful and no one would see them unless I was barefoot so I thought I might even be able to keep them painted once grandma left.

From here we were led over to these little table for our manicure. Again they soaked our hands and fingers and pushed the cuticle back at least that is what the lady said which made my nails look longer. She then glued some extensions on the end and cut them down till they were about a half inch long. She then started to spread a paste over them and shape them. It was so relaxing and such a great feeling. It took her almost an hour to do this and then she took the same bright red color and painted our finger nails, now this I knew I couldn’t keep which I was sad about but I had them now.

We then went over to another chair where we put our hands under these lights for the polish to dry and while we did this they gave us a facial. They put a cream on our face that kind of hardened and then washed it off. They then spread another paste above my eyes and pushed down and rubbed then I felt them pull away and I jumped. Up to now everything had been so relaxing and fun but this hurt. I suddenly realized I had just had my eyebrows waxed. I got a little scared now as things might be getting out of control. The lady put a moisturizer on my face and massaged it in which relaxed me and then she started to apply makeup. I couldn’t wait to see what I looked like.

When this was all done we went back over to the chairs we started at and they took the curlers out of my hair and brushed it out. I was could not wait to see what I looked like. Finally she was satisfied and turned my chair so I could look in the mirror. I was in shock, I was both scared and thrilled at the same time. I did look totally beautiful and completely like a 16 year old girl but I also had a very feminine haircut and style with bangs and my light brown hair was now a blonde color and really curly. It would be impossible to make this look at all like a boy’s hair style. My eyebrows were also well shaped with a high arch and there was nothing at all boyish about them, actually most girls in my class would love to have eyebrows like this. I looked at grandma and told her I was worried what mom and dad would think. She smiled and gave me a hug and said, my beautiful granddaughter you are a young lady now and they will see you for that, they will be so proud of you. I knew what she meant and had I been a girl that would have been true but I was their son and they had been going along with this while grandma was here this was a little more permanent. There really wasn’t anything I could do so I made the best of it after all it is something I dreamed about doing. I couldn’t wait to post pictures on my Facebook page and chat with some of my friends especially a few of the girls I had been chatting with.

It is funny the friends you can make online they are from all over the world, and although you never really meat them they are in some ways really good friends. Most of them other crossdressers, some real girls I had met and even a few older woman that in some ways were like online moms that I could talk to and it was amazing the support I got from all of them. The girls all told me I needed to do what made me happy the older woman told me the same thing and that they would love their child no matter who he was or how he wanted to live his life, one even encouraged me to tell my mom and dad how I felt. Tonight when I got online I would have so much fun but right now I had to focus on the here and now and enjoy this time out.

We walked into the mall and I had a whole new kind of self-confidence as I knew I looked as good as any other 16 year old girl at the mall, actually probably better. We stopped at a little jewelry store and grandma bought me a ring, bracelet a necklace and some earrings. The earrings were little gold hoop earrings and they were for pierced ears. I looked at grandma and she smiled you are 16 you should have your ears pierced, I looked at the lady and figured why not as at this point pierced ears would be the least of my problems so I sat down and in a few minutes I had gold hoop earrings in my ears.

From here we went to the food court and had a late lunch and then we hit the mall shopping. We went to every store that sold anything that a girl might want. Shoe stores, dress shops, Victoria’s secret which is one shop I had always wanted to go into but was too afraid. We even went to a bridal store and I tried on a wedding dress. I tried on so many beautiful dresses today it was like being in heaven and the funny thing is somewhere during the day I stopped thinking about being a boy dressed as a girl and started thinking of myself as a girl and enjoying it. It was the most wonderful day of my life.

Well by now it was after 5 and grandma called a cab to take us home. We were on the way home when mom called me on my cell phone. She said her and dad were worried when they got home and we were gone. I told her grandma had wanted to take me shopping today and I heard the pause in her voice, did she take you as a girl? I said yes and I heard my mom tell me how sorry she was and she hopes I was okay. I really didn’t want to go into it on the phone with grandma right next to me so I just told her it was fine and we had a great day and there was nothing to worry about and then I did tell her grandma did go a little over board today to give her a heads up. She asked what I meant and I just quietly said two words, beauty parlor. Mom let out a small gasp, sweetie I am so sorry for you, I will make this up to you somehow. I just said its okay I am fine and I knew I would soon be home and they would see me and what had happened.

The cab pulled up in front of the house and for the first time I was scared. I got out of the cab and grandma and I walked to the front door, I did my best to stay behind her. We got inside and my mom came to great me, she stopped and her mouth dropped open and she couldn’t speak. Grandma looked at her and said, see what a beautiful young lady your daughter has turned into. Mom gained he senses back and said yes she is beautiful. She gave me a hug and whispered in my ear that everything would be alright. She then called dad by saying, honey come see how beautiful your daughter is grandma took her to the beauty salon today for a complete makeover and you will not believe how beautiful she is now.

Dad came around the corner and looked at me and I could see in his eyes he was confused, not upset but more of a wow he is a beautiful daughter. He paused for a moment and looked at me, then grandma and then me again. Then he walked over and said I guess my little girl has turned into a beautiful young lady and he gave me a kiss on my cheek.

We all went in and had a nice dinner and talked and I could see mom and dad looking at me from time to time trying not to stair, and as time went by we got back to a more natural sense in the house and it was almost like they overlooked what had happened to me so I felt more relaxed. That night when I went to bed dad actually called me over to kiss him good night and mom and grandma took me up and helped me clean off my makeup and get ready for bed.

The next day my birthday I got up and mom, dad and grandma were all waiting for me downstairs. I opened my presents from mom and dad and they were the normal type presents. I opened grandma’s presents and I found several pairs of skirts, several pairs of Capri’s and about 20 tops all very colorful and so pretty. Mom and dad said we would have a nice dinner tonight at home as mom would prepare anything I wanted. As I thought Grandma spoke up, nonsense it is her 16 birthday we have to do something special, I have planned a special day we are going downtown to the city center and go up in the Space Needle and walk around and see the city center. Mom and dad looked at me and without thinking I said that sounded like fun. I no more than said it and realized how it must have sounded. Mom smiled and looked at dad and said well if that is what my daughter wants lets go. Dad looked at me and said okay it sounded like a fun day.

I went and got my purse and mom followed me, are you sure you are okay with this sweetie, we will be outside all day. I looked at mom and said it would be fine it was only one day as long as it was okay with her and dad. Mom gave me a little kiss on my cheek and said it was fine she would love to have a daughter for the day and with that we were off.

It was funny as the day went by we all became more relaxed, I acted like a 16 year old girl and mom and dad treated me that way. Mom even pointed out a couple things I did that a girl shouldn’t and then we both broke up laughing when we realized what she said. The day was awesome to say the least. No one questioned if I were a girl, people held doors open and even several boys looked at me and when one came over to talk to me dad was right there like an over protective father should be. We had a wonderful day and then went out for dinner and it was after 9 when we got home and I was so tired I was ready for bed. Without thinking I went over and gave my dad a kiss and he gave me a kiss back and then I kissed mom and grandma and up I went to bed.

Sunday Morning g I got up and mom and dad were downstairs for breakfast but Grandma hadn’t come down yet. Mom said morning sweetie and dad asked how I was doing. I told them I was fine. We sat and talked for a bit and then mom gave me a hug. Sweetie we have a problem, I just looked at her. You know we love you and we are so proud of the way you have acted and all you have done for your grandma and she didn’t mean any harm to you, she loves you very much as we do. I looked at them both and said I know. Well dear the things she has done, the hair color it will be weeks before we can color it back unless you want to cut it all off. The nails again will be a week or better before they can be removed, we can cut them short but still you will have acrylic on them and the eye brows there is nothing we can do about them till they grow back. I looked at them again and said what are you saying? Mom looked at dad and then said well dear, we know Grandma is leaving today but it will be very hard for you to look like a boy for a while, it may be easier and only if it is okay with you to be a, well a girl, our daughter. I thought for a moment this was my fantasy coming true to live as a girl for a few weeks.

I paused for a moment to make sure I didn’t sound too excited and to get just the right words. I guess if you think it is okay I mean if you don’t mind it might be easier. Mom was getting ready to say something when dad spoke up, we love you Kelly and nothing will change that, not how you dress or what you do, you are still our son, well I guess daughter. All that matters are that you are happy and healthy. Plus I will admit I had always hoped we would have another child maybe a daughter and well I actually enjoyed yesterday. Mom and I both looked at dad for a moment as we took in what he said. He was the one I figured would be the least understanding. Mom looked at me and said your father is right, boy, girl, son, or daughter I will love you no matter what. You are such a good person for doing what you did for Grandma and like your father I would love to have a daughter to do all those mother daughter things with. I was actually a little jealous about grandma going to the beauty salon and getting her nails done with you as I thought it should have been me. Does that sound weird?

I looked at them and could no longer hold back, I love you both so much and I feel so bad as you think I am such a wonderful son for what I did for Grandma. The truth is I really liked this, when she started giving me girl clothes I loved it as I really like dressing this way. I was too scared to tell you the truth, I am your son but I feel more comfortable this way. I would like to stay your daughter for a while if that is okay with you. Dad got up from the table and came down by me and looked me right in the eye, I was afraid that what I said may have changed everything. Dad leaned down and gave me a kiss on the cheek looked at mom and said I guess we have a daughter for a while. Then he looked at me, now young lady I expect you to be a proper young lady and that is how mom and I will treat you, do you understand? I said yes. That is good and remember we both love you no matter what. He looked at mom and said I guess we will have to fix up that room proper for a 16 year old girl. Mom looked at me and smiled we will have so much fun dear but you must promise me one thing, you will always be honest with us. If you want to go back to being our son you must tell us or if you want to stay our daughter that is okay, even if you want to permanently change. Now that is something had never thought about as I had always planned on meeting a girl and getting married someday, I had never even thought about boys. I looked at mom and told her I would be honest with them and that I didn’t ever see me wanting to change permanently as I had no interest in boys.

On the bright side I would no longer have to pretend just when grandma came over. Just about this time Grandma walked in had gave us all a hug. She smiled at me and then my mom and dad. She said she would be sad to go but would be back in 5 weeks again for a visit as she loved all of us so much. I gave her a hug and said I would be looking forward to it and maybe we could go shopping and to get our nails done at which mom spoke up and said only if she could go also. Grandma hugged me and said that sounded wonderful and she could think of nothing better than going to the nail salon and getting a pedicure and our nails done with her daughter and grandson. I gave her a kiss and then stepped back and looked at her. Mom was the first to speak, what did you say mom? She smiled again I said there is nothing I would enjoy more than getting my nails done with my daughter and grandson. I looked at her but you thought I was your granddaughter?

Grandma let out a little laugh, sweetie I may be old but I could never forget you were my grandson. I just knew you liked to dress as a girl and wanted to but were too afraid to tell anyone. So I figured if I treated you as my granddaughter and bought you the things you needed you would say something, the beauty salon was my last hope, I hope you don’t mind but I love you too much to not help you be who you feel you are.

I looked at her, how could you possible know, sweetie you are so young. When you put my e-mail address into your e-mail account it linked it with your Facebook page and I got a friends request. I was a little surprised to see you dressed up and posting pictures and even though I couldn’t see your face clearly I recognized your bedroom. We have been Facebook friends for several years now, I am Miss James. She was one of the older ladies I had been talking too online for a couple years, the one who told me that my parents would understand and I should tell them as all parents want their children to be happy no matter what. She looked at me and gave me a big kiss, those chats we had changed my life and made me realize how important family is and what I was missing when I realized I didn’t even know my own grandson. I didn’t know what to say so I just gave Grandma a big kiss and told her I loved her. She looked at me and asked if I would be seeing her off at the airport today and I told her I would as she had helped me accept who I was and I loved her for it. And so that is how my life changed. It is now the end of summer and I have lived the last two and half months as a girl. I talked with mom and dad last night and told them I want to stay this way for a while longer so I have transferred to another school and will be going to school this year as a girl.

Mom and dad both love me and they love having a daughter although sometimes I think they miss their son especially dad when we are late going someplace and dad hast to wait for not only mom but me to finish our hair or makeup. Mom loves going to the beauty salon with me every other week to get our nails and hair done. I think mom has more of a glow about her now and I think she looks better now than she ever has as we do all the girly things together and she now also has long acrylic nails and wears makeup all the time and has even tried a few new hair styles. Being a girl is so much fun I can’t wait to see what the future holds.

PS Grandma is planning on moving here soon as she just bought the big house across the street, yes it is a 6 bedroom 4,000 sq. ft. house, she is downsizing.

How your life can change   Leave a comment

How your life can change

By Toni Girl

My name is Kelly and I just turned 21 and my life is way different then I thought it would be, I have always been small I am only 5’4″ tall and weigh 125 so I really look more like a little kid. It also made it hard growing up as all the girls seemed to like the big football type boys. The only good thing about this is it allowed me to concentrate on my studies so I always got good grades.

I was 19 when I moved to Southern California and I found a small house in an older rundown neighborhood. Several of the houses were vacant but the house next door which had a young lady named Jill who lived there and she was beautiful and about the same age as me so I tried everything I could do to get to know her and it did work as we did become friends but I wanted more. We both worked at a local burger king as when you are young and just starting out it is hard to find a good paying job. We started carpooling to work to save money and this allowed me to get to know her better. We also started having dinner together always as friends though.

Jill was a pretty private person the only thing I knew for sure was she was not dating anyone. One night I was at her home for dinner and we were talking when I noticed something under her chair and reached down to pick it up and I am not sure who was more shocked as I pulled out a pair of handcuffs. I could see in Jill’s eyes she was embarrassed and scared so I made a joke about wondering what it would be like to be handcuffed which put her more at ease. We ended up talking for hours and Jill finally opened up to me. She had a thing for bondage and she would handcuff herself sometimes but she said it wasn’t the same as she could always unlock the cuffs. I felt we made a little connection that night.

Now I had never really thought about bondage but thought this was a chance to get closer to Jill and although it wasn’t something I really wanted to do I wasn’t against it either, I guess I was pretty neutral about it so the next night I was over their I talked with her and told her I was curious about bondage and would also like to try it. So after talking to her she pulled out a box that had all kinds of bondage things in it from paddles, leather straps, gags, ropes and several more pairs of handcuffs. I was in shock about all the things she had and that is when she asked me if I would handcuff her and I agreed. Now I was thinking this would be simple but she quickly put the ball gag in her mouth, put some cuffs on her ankles and then handed me a pair of handcuffs and the keys and turned around and put her hands behind her and I locked her up. I could see she was a little excited so I went ahead and left her on the bed and went out and cooked dinner which took about 45 minutes.

When dinner was ready I went back to the bedroom and she looked like she was really enjoying herself so I picked her up and carried her to the table. I then took the gag out of her mouth and she asked me what I was doing and I just smiled and told her I wasn’t ready to release her and that I would be feeding her tonight. Now I could see she was a little shocked, excited and maybe a little scared as she realized she was locked up till I released her. It was an incredible night.

The next night Jill came to my house for dinner we had a nice dinner and then Jill told me it was my turn and she pulled out some of her bondage stuff. The first thing was something made of leather with a collar which she put around my neck and it had a piece that went down my back. She then pulled my arms up behind my back and strapped them in behind my back. I was totally under her control now as there was no way I could get out by myself. I wondered what was next as she pulled me close and gave me a big kiss. This is the first kiss we have shared although I had dreamed about it. She then put the ball gag in my mouth and I was hers for the night. Now as I said I had never really thought about bondage before but it was quite the feeling, fear, excitement and helplessness. For the next couple hours I stayed this way and had to rely on her for help including going to the bathroom which was scary as I said we were just friends so she had never seen me naked but she pulled my pants down and helped me go and as there was nothing I could do I couldn’t even speak to her so I was a little shocked when she didn’t pull my pants back up so now I was naked from the waist down and I must admit I was a little excited which Jill noticed and she would play with me from time to time which made me all the more excited. After a couple hours she had me stand up and she pulled out a paddle and started to spank me, not real hard but enough to cause me a little discomfort and strangely enough I got real excited again at which point she pushed me down on the bed, pulled up her skirt and went down on me. It was the most incredible experience I have ever had and it didn’t take long and I was done. I couldn’t move and she just laid on top of me for a while.

Well this went on for the next couple weeks one night I would be her slave and the next she would be mine. As time went on we settled into a pattern and O was spending more of the time as her slave and I really enjoyed it. It seemed to happen so slowly that I didn’t even notice things were changing, it is funny how you miss the little things. Now we both had weekends off so the way it would work is Jill would be my slave on Wednesday and Thursday nights and from Friday to Wednesday I was her slave and since we had weekends off from Friday night till Monday morning I was her slave nonstop and we both loved it. After about a month we both knew we were in love.

Friday night we got home and Jill quickly striped me naked and bound my arms behind me and put the gag in my mouth, smiling at me she told me that as her slave now she wanted to mark me kind of put her brand on me which scared me a little as I was helpless at this point. She pulled out a bottle of bright red nail polish and told me she was going to paint my toes and when I hesitated she quickly grabbed the paddle and gave me a spanking that was just a little harder than the times before and told me it was not my place to refuse her and that no one would see my toes so I sat down and soon I had bright red toe nails. Later that night she again went down on me and it was another incredible love making session. I never knew it could be this way. At night she released me and we went to bed.

The next day when we got up I we took a shower together, she lathered me up and I did the same to her and then we washed off and my skin never felt softer that was because all my body hair not that I had much was gone. As I was getting dressed she handed me a pair of her pink panties and told me she wanted me to wear them as no one would see them and I didn’t even hesitate I just put them on. They felt different but in a good way as their soft feel against my smooth skin was incredible. So from this point I wore her panties every day and always had my toe nails polished and she was right no one could tell. It also gave me that feeling that I was still under her control even while at work and also when it was my turn to tie her up.

We had an incredible relationship and I learned I loved bondage. Well we did this for a few weeks and it was so much fun. It was Friday night and Jill had me strip down to just my pink panties and she started to bind my arms behind my back when she stopped and looked at my chest. She smiled and told me I had little man boobs extra fat on my chest and we needed to fix that so she pulled out a pink bra that matched my panties and put it on me. It was a little tight and actually pushed the fat up giving me small boobs. She then secured my arms behind my back for the evening. The bra felt a little strange but also exciting and I couldn’t help but look down to see my small boobs and the cleavage that was there. After a couple hours Jill started playing with me and as usual it didn’t take long to get me hard, she knew how to push all the right buttons on me. That night she had me wear the bra to bed along with one of her teddies.

Saturday morning we got up and we were going to Disney Land for the day and as we got dressed Jill handed me a pink bra to go with my panties and said it would be fun and so sexy if I wore it today. Now it was a little on the cool side and I was wearing a sweat shirt so I figured why not so now I was wearing pink panties and bra along with having bright red nail polish on my toes. Now I also must say that over the last couple I have not had time to get a haircut so my hair is down almost to my shoulder. I also didn’t look that close to see that even with the sweat shirt you could still see little boobs sticking out.

Well we got to Disney land and went in and we had so much fun and went on so many rides. At lunch we found a little café to eat a and the waiter came over and ask how we were doing by saying How are you ladies dong today which caught me off guard but then being so small and the long hair I could see where he made the mistake but before I could correct him Jill spoke up and told him yes we were having a wonderful girls day out. The rest of the day went by so fast and a couple times men would hold doors open for not only Jill but also me and I just went with it.

That night when we got home Jill was all over me, she didn’t even take time to bind my arms or anything. It was one of the most magical nights I have ever had. On Sunday morning we got up and we were going back to Disney land as we had bought a 2 day pass. Jill had set out a pair of white pantie’s and a pink bra which I put on but I did question why they were different colors at which point she smiled and told me I was not to question her choice and she then had me bend over and gave me a spanking, not in a mean way but it did get my attention. Jill just smiled at me and handed me a pair of her white Capri’s and a pink top as today it was sunny and would be in the 80’s and told me as everyone had thought I was a girl yesterday we were going to do it right today. I knew not to challenge her as I had become submissive to her by now so I put them on. I will admit you could really see my little boobs and the cleavage and of course the bra.

Jill then had me sit down at her vanity and used a curling iron on my hair to give it some curls and actually made it into quit a feminine style. I looked into the mirror and I could see how people had mistaken me for a girl yesterday. As I was doing this Jill started to put the same red nail polish on my fingers which really made my hands look different. She then did a quick makeup job mascara, eye shadow and a rose lipstick and she did the same to her face. She then handed me a pair of her open toed sandals which I put on and they showed my toes off well. I looked in the mirror and there was no way you could tell I was not a girl. With that we were on our way. It wasn’t till I was in the car and we had been gone from the house for a few minutes when it hit me what I was doing today and I got scared. Jill just smiled and told me to relax as I would be fine besides there was nothing I could do about it now which was true. We had a great day and everyone we met saw nothing more than two young ladies out for a fun day at Disney Land. We even had a couple men hit on us which really made me feel uneasy. Jill even hot pictures of me that day.

Monday morning came and I was so worried that someone would notice some trace of makeup I missed but Jill helped me get it all off although my hair still had a bit of a curl to it. I put on my panties and bra and off we went to work. I am sure my little boobs were noticeable but no one said anything so this became our lives bondage every night and on the weekends I would become a girl for the weekend. It all happened so slowly that I never even really realized what had happened.

Well a year later we both turned 21 and Jill had got an offer from a casino in Las Vegas to be a cocktail waitress which would mean way more money than working at Burger King so we talked it over and decided to move there and I would try and find a job also. We both gave our two week notice. And started to plan our move. Jill talked to me and told me she thought I should be a girl for a week or two while we moved and got settled and before I started to look for work. Now I know I should have hated this idea but there was a little thrill of excitement about doing this so I agreed. Our last day of work was a Friday and we were going to make the drive to Las Vegas Saturday afternoon. The hotel she was going to be working at had given her a room for 5 days to help till she could find an apartment.

So Saturday morning we got up and got ready. Jill gave me a cute little short skirt and top to wear and she only did a light makeup and we were off. We didn’t leave town though we went to a local beauty parlor and we both got pedicures and acrylic nails in bright red and then we also had them do our makeup and hair. We both looked like we had just stepped out of a fashion magazine. Then we were off. We got to Las Vegas about 6 pm and checked into the hotel room. .

On Sunday we drove around looking at apartment buildings and getting an idea where we could live and what we could afford. Then we went back to the hotel and did a little gambling. It was so much fun and I even forgot that I wasn’t really a girl as I didn’t have that fear of running into someone I knew. On Monday Jill went to her orientation and I hung out in the casino. Jill was going to start work on Wednesday so we decided on Tuesday we really needed to find a place to live so we scheduled a couple appointments at a few apartment buildings the casino had recommended. They were all nice but the third one we went to was great. Nice big apartment. Clean well kept up with a swimming pool and weight room and the rent was only $700 a month which was in our budget. While we were there Jill ran into a couple of the girls she had met at orientation. So we all talked for a while as the apartment manager did a check on us and then we got our keys. The other two girls also decided to rent an apartment here. Once all the paper work was done we went back to the hotel for dinner. It would take a couple days for our stuff to be delivered so we would stay there for the full five days.

While Jill worked I was cleaning the apartment and getting it ready for our stuff to move in. I also met a few more of the neighbors who also worked at the same casino. Seems a lot of the employees live here. Well we only had to sleep on the floor a few nights before our stuff arrived and what I was really looking forward to was our bondage stuff as it had been over a week since either of us had been bound.

Jill finally got a night off and I was ready, she secured my arms behind my back and put the gag in my mouth and then gave me a spanking. I can’t tell you how much I had missed this. She then got a real serious look on her face and smiled. She asked me if I really enjoyed being submissive to her and doing what she wanted. With the gag all I could do is nod yes as I really did enjoy it. She told me she was glad as I was going to be under her control and she would take care of me which made me happy. She then smiled again and told me she had the best and most secure bondage figured out for me and hoped I would love it. I again nodded yes as I was sure I would.

That is when she told me something I had not thought of or counted on. Since we had moved to Las Vegas I had been living as a girl full time. All our neighbors new me as female, so did the apartment manager who had rented the apartment to two girls, there was no way I could go back to being a man. I was now going to live as a girl as long as we lived in the apartment which we had signed a two year lease. I was trapped. I could feel the fear inside me and I wanted to scream but the ball gag prevented me from doing that. Jill just smiled and told me to sit and think about it for a while and then she went into the other room. I was helpless as I sat there waiting. I had never been so scared in all my life.

Jill came back two hours later and took the gag out of my mouth and told me that I knew she was right I had to stay female for the foreseeable future. I knew she was right as there really was no way out. I was now in a permanent bondage as a girl. Jill made it easier on me by telling me she loved me and would never leave me and so we started our life together.

I get my nails done every other week and I love the long nails, Jill even got me a job at the casino with her and yes I am also a cocktail waitress and with tips we are both making good money. It took me a while to figure out that the more I flirt with the men the better the tips. I am still uneasy about this but the money is good.

Being unemployed leads to a surprise   Leave a comment

Being unemployed leads to a surprise

By Toni Girl

Well it all started about a year ago. I was living in a small neighborhood of older homes as they were the only ones I could afford on the amount of money I made as I only had a high school education. I had the smallest house on the block only 900 sq feet but it had a big unfinished basement. You see I live in the mid west and most homes here have basements for when the bad weather hits. I had great hopes of fixing it up though and turning it into my special room you see I am a crossdresser and although I would never go outside I love to dress up at home. I am actually pretty good at it as I am short for a man 5’6″ and very thin and wear my hair long just for this reason. Well because of my little hobby I kept to myself even my neighbors I shied always from. I mean I knew them nut didn’t really socialize with them. By the way my name is Kelly.

My one neighbor was beautiful long blonde hair and looked like a model and best of all she was single, her name was Sarah. She had just got hired as a flight attendant for an airline just about the time I got laid off from my job, seems my boss had a gambling problem and went bankrupt. Occasionally we would talk and she told me about her new job and of course I told her about my unemployment, luckily for the unemployment as that would allow me to survive for about a year so I was going to enjoy a little time with my crossdressing.

Well she finished her training and got on a regular schedule and as soon as she did that she called me over one day to ask me a favor, seems she would be gone for 2 to 3 days at a time and wanted to know if I would keep an eye on her house and water her plants which I agreed to and she gave me a key and showed me her plants and how much water they needed. She also told me the basement was just storage and really cluttered so no need to go down there. I would say we had become friends which was so nice as I really didn’t have many because of my crossdressing.

Well as she started to travel I would go over and check on her place and water her plants. It had been a couple weeks and I don’t know why but suddenly the thought popped in my mind and maybe it was seeing her beautiful dress on her bed but I realized we were pretty close to the same size. I held it up to me, now I am about an inch taller than her but as I am really skinny and she has a really nice figure I was sure it would fit but I couldn’t so I put it down. Later that day I couldn’t get the thought out of my mind and so that night I went back over to her house and tried it on. It fit perfectly well if I had brought my silicon breast with me and had a little more hip.

I knew it was wrong but I couldn’t stop myself and so now every time she left I would go play dress up at her house which was wonderful as she had so many more cloths then I do and the shoes looked like a department store. I often wondered why such a beautiful woman would be single but then my mind went back to her cloths.

I had been doing this for a few months a couple times a week when she was gone, I even tried a little of her makeup but this was too risky so I would bring my own over and by now is was completely transforming myself while I was at her house it was the perfect life. One day I was walking around her house all dressed up in a red dress and heels and as I went in the kitchen I noticed the door to the basement wasn’t shut tight and I don’t know why but I opened it and looked downstairs. From what I could see it looked pretty clean and so I went down to check it out. it was divided in half and there was a sofa and big screen TV on the one end and very nice and about half way down was a solid wood door so I went down to take a look.

When I opened the door I was in shock, it looked like a medieval dungeon. There were 2 jail cells on one side of the room, on the far wall were chains hooked to the wall and all kinds of leather straps, paddles and other things I had no idea what they did. I was fascinated so I started looking around. The jail cells the locks didn’t seem to work which was kind of fun as I went in one and closed the door and pretended I was being held captive. I looked in the next cell and it had an old wooden stockade, it was hug, there was a place to lock your feet and then you bent over and put your head and hands in to lock them so I went to that cell to check it out and just like the other one the lock on the cell didn’t work. I looked at the stockade and where you put your feet were held in place by flipping a latch down and then you could paddle lock it but you could also just put the lock through so it wouldn’t release and you didn’t have to actually lock the lock.

The part you put your head and hands in hinged down and it looked like there was a place to put a wooden peg in to hold it shut so it would take someone else to lock you into this. I don’t know why but this excited me even though I had never thought about bondage. I pulled the cell door shut and put my feet in and slid the lock through careful not to lock it. I put my head and hand in and let the top come down and them pretended that I was a prisoner and forced to dress this way. I had found a whole new excitement to my cross-dressing.

Over the next month this became my normal routine. I even started to use one of her ball gags so I could scream it was amazing how well the ball gags worked as I could only get a muffled scream out no matter how loud I tried. I doubt if anyone in the upstairs would have heard me.

Needless to say I really wasn’t looking hard for a job as when Sarah was gone I was at her house almost nonstop. I had even got in the habit of just putting on her bras, panties and heels and doing my makeup and then going down to the dungeon. I thought a couple times about asking her about the dungeon but could never figure out a way to bring it up. As it would be so much more fun to actually be locked up by someone else but then again I love the crossdressing part. I even looked at the locks on the cells to see what it would take to fix them but it looked like they were made this way. There was no locking mechanism in the door just a hole where it would be and no place to put a key. I loved Sarah’s trips. She would leave in the morning and do a flight to Hawaii which was a 10 hour flight as she would fly from where we lived in Oklahoma to LA have an hour or so layover and then on to Hawaii. She would spend the night and then do the reverse so she would get home the next evening about 6. This gave me the one hole day, that night and the next morning to play and by mid afternoon I was always done and cleaned up to make sure by the time she got home things were back perfect.

Well about 3 months ago Sarah left on a Monday morning and I started normal fun. I had such a normal routine down. I would go over to her place and do my hair and makeup, put on one of her bra, panties and 4″ heels and then go down and spend a few hours playing prisoner, I loved the stockade. This would take me into mid afternoon at which time I would go up and touch up my makeup and put on one of her beautiful dresses. I would then fix myself dinner; I would bring my own food and then sit around and watch TV, play on my laptop and have a fun evening. about 11 I would put all her cloths back just as I found them and put my cloths back on and go home most of the time I didn’t take the makeup off as I just had to walk next door to my house and I could cut through the yard and it was dark out. the next day I would go back over and do the same thing play in the dungeon till maybe 3 or so you see with a computer you can tack flights by flight numbers so I could see where Sarah’s flight was and I knew once she left LA she had about a 3 hour flight home and then it would take her about an hour to get home from the airport. Today her flight left LA at 2:30 and so she should be home about 6:30 so I was going to play in the dungeon till 4 and that would give me time to change back and make sure everything was right when she got home

So Tuesday morning I got dressed and went to the dungeon and played till noon then went up and made myself a sandwich and checked on Sarah’s flight it was right on time. it was about 2 when I went back down to the dungeon and I was wearing her hot pink bra and panties and her 4″ pink shoes I looked hot all made up. I went into the cell, shut the door and grabbed a ball gag and put it in my mouth. Next I put my feet in the stockade and put the lock through again being careful not to lock it. next I put my head and hands in and let the top come down and again I was trapped well not really but I could imagine. I would pretend to struggle and on these days it was always more exciting as I knew Sarah would be home in a few hours and I could pretend I was stuck and she would find me. It was about 4 and I heard a little humming sound which I figured was the heater coming on, funny I had never heard that before well it didn’t matter as I was having fun. I was watching my laptop on the floor as I always kept an eye on Sarah’s flight. It was half way home now from LA so I knew I had about 2 hours or less to change back and make sure everything was in there proper place and I had washed off all traces of my makeup and was back at home. I pushed the top of the stockade up to get out and it didn’t move, I pushed again and nothing. Something was wrong, the stockade couldn’t be locked by me alone so I knew I just had to push again and still nothing.

I was scared now as something was really wrong, I was trapped. Wait this can’t happen I just need to calm down as I had checked this and it didn’t lock, someone would have to put the wooden peg in and I could see that had not happened but no matter how hard I tried the top would not go up and release me. I was stuck. I calmed down to think what to do as I glanced at my laptop on the floor. Sarah’s plane was getting closer what was I going to do. she would get home and find me in her dungeon after she had told me not to come down here, she would also find me wearing her stuff and dressed as a girl in full makeup. This was bad wait what if she doesn’t come down here, with the gag in I could scream all I wanted and upstairs she would never hear me. I could be trapped here. I don’t even know if she comes downstairs or uses this stuff. I was really scared and the more I struggled but nothing worked I was trapped and as bad as it was my only hope was that Sarah would find me and set me free of course that would mean an end to our friendship. All I could do is wait. Sarah’s plane landed and I knew it wouldn’t be long.

Time passed so slowly as I waited it was after 7 now and I would have thought Sarah would be home by now but then again I really couldn’t hear if she was upstairs and I tried screaming but it was such a low muffled sound. Suddenly the door to the room opened and in walked Sarah and she was wearing a really nice black dress and heels and her makeup was looking perfect. She looked beautiful as I have never really seen her all made up. She walked over to the cell door and pulled on it and it didn’t open and she just smiled at me. What was going on. She looked at me and smiled again and then started to speak. “well what do we have here a new prisoner?” with the gag I could not speak. She went and got her laptop computer and walked back over to the cell door. She pushed a couple keys on the keyboard and then pulled the door open and walked in.

She looked at me, “well you are in a little trouble aren’t you?” I tried to lift the top and it still would move or release me. Sarah took something off the wall behind me, “well you have been a naught little girl wearing my cloths without asking me first”, and I felt her spank me with a leather paddle. Not really hard but it got my attention as I knew there was nothing I could do I was stuck. Sarah walked back in front of me and looked at me, “well what am I going to do with you” she asked and again I could say nothing because of the gag.

Sarah smiled again, “well you need to be punished so I guess I will have to spank you”. Smiling she looked at me and said, “when you think you have been punished enough and have learned your lesson please say I am sorry Mistress Sarah”. And as she walked back around behind me I tried to scream as I knew with the gag I could not say anything.

I felt the first swat and the sound was way worse than the pain but then the next one was a little harder. I tried to scream I am sorry mistress Sarah but all that came out was muffled sounds. Sarah spanked me again and again and the pain was getting to me. It was not unbearable but with each swat it hurt more and I could feel the tears rolling down my face. They were not a brutal attack but more designed to get my attention. I lost count but guess she spanked me 20 times or so before stopping and walking back in front of me, “well have you learned your lesson” she asked? I couldn’t speak but did the best to nod my head yes.

She set the paddle down and released my feet and then pushed a couple keys on her laptop and the humming sound stopped and I could push the top up which I did. As soon as I stood up I took the gag out and started to apologize about everything, wearing her cloths, playing in her dungeon I was still crying. Sarah put her finger to my lip to shut me up, “Listen to me Kelly, tonight you are my slave and you will do what I say and refer to me as Mistress Sarah, do you understand”? I said yes. “now I want you to go upstairs to my room and get that red dress you wore last week and the red heels and put it on and touch up your makeup while I get dinner on the table I stopped and picked us up some Chinese food on the way home”.

I went upstairs and did as she said still scared and worried what would happen. I came downstairs to find her sitting at the table with the food spread out and a bottle of wine open so I sat down. I started to apologize but she again stopped me, “be quiet, tonight you will address me as Mistress Sarah remember, now you were a naughty girl for taking my things without asking first and for that you have been punished. You will not do that again without asking me do you understand”? I said yes mistress Sarah. “Good now we are going to have some fun”.

She then started talking about her family, seems her parents had been killed a couple years back in a car wreck and left her their house. she told me how they love bondage and had built the dungeon downstairs to play in and would take turns. She also enjoyed it but had changed the locks to a magnetic lock she could control with her computer so she could lock herself up and set a timer. If the computer stopped or the power went off the locks would release so it was safe. Turns out she had used her computer from LA to turn the locks one when I was in it.

I asked her how she knew and she said it was little things, first she had noticed some lipstick on one of her ball gags but it was when she found an eye shadow in her bathroom that wasn’t hers she got curious and as the dungeon is controlled by her computer including cameras both downstairs and upstairs she had started checking in on her house while she was away and had been watching me dress and pretend to lock myself up. She was mad at first but then thought this might turn out good as we both liked the dungeon. I know had someone who knew about my dressing and seemed okay with it. we had a nice dinner and talked and I always remembered to addresser her as Mistress Sarah.

After dinner we got up and she smiled at me, “now may slave we are going down to the dungeon and we are going to play with some of the other toys which you have to have someone to lock you in”. I was a little nervous when she came over and gave me a kiss on the cheek. “Tonight you are my slave and I am your mistress but tomorrow it is my turn to have you lock me up and spank me”. This caught me off guard but made me feel so much better as I knew we were going to be really good friends and who knows where it will lead.

That is how it all started who knows where it will lead.

A new way of life   Leave a comment

A new way of life

By Elizabeth James

Well I grew up in Las Vegas and although it is a fabulous place to visit and yes live if you don’t work for a Casino life can be hard. My name is Kelly and I have lived here all my life but being only 18 and not a lot of options for employment at least not that paid well. Add to the fact I was very small for my age only 5’4″ tall and weighed less than most 14 year olds so finding a job was hard. Mostly I did odd jobs for whatever money I could get for what I needed. It really wasn’t till my mom died in a car wreck she was hit by a drunk driver that things got hard. You see my mom had me when she was only 16 so she was only 34 when she died which no one really plans on so she had nothing set aside, no life insurance other than the $10,000 from the casino she worked at. Now I had to support myself which means I would need rent money, food and all the other bills that come along with living on your own. When you are young you really never understand how much things cost.

I was downtown one night at the Freemont Experience and yes I was thinking of begging which is against the law in Las Vegas when I noticed some people dressed up in costumes and tourists were giving them money to get pictures with them and I thought what a idea so I went home and dug out some of my old costumes. Yes as I really haven’t grown since 4th grade they all still fit me. I had all the super heroes, Superman, Batman, Thor, Green Lantern and several others. So I was ready.

The next night I put on my Superman costume and went back downtown and started walking around. It wasn’t long before I ran into some other people in costumes and I tried to talk to them to find out more about doing this. That’s when my first problem started. There was another guy dressed as Superman and he was not at all happy to see me in the same costume and he was a lot bigger than me. He started to yell at me, for a minute I was scared. that’s how I met Jill she was dressed as Cat Woman and she came over to my aid and told them to leave me alone which they did but not without warning me about wearing the same costume as them. Jill was so nice and we got to talking and she told me all about how this works downtown. Seems you can dress up and get pictures with people but you can’t charge them or ask them for money. If they give you a tip for getting their picture taken with you that is fine, this is something I didn’t know as I was planning to ask for money.

The evening went all right and I did get some tips but not much as it seems that a 5’4″ scrawny Superman is not on the top of the list for pictures. It was about 3 am when Jill and I decided we had been there long enough and she asked if I wanted to grab a bite to eat so we went to one of the all night coffee shops in a casino. I had been down there for 6 hours and had made about $50 which wasn’t bad as it was tax free I guess. Then Jill counted her money and she had over $100, I was shocked. I asked her and she told me it was all how you approached people and of course how awesome you looked. I knew I had to work on being more outgoing if this was going to work and of course get a better costume. Over the next couple weeks I tried different costumes and some were better but not by much. I think my best night I made about $80 while Jill was still getting over a $100 every night. Jill and I became friends during that time and we would get together during the day as I was still living at the apartment my mom had rented which had a pool although I wasn’t sure how long I could afford the $1,000 a month rent.

Jill suggested that maybe come the first of the month I move in with her as she had an extra bedroom and we could split her rent which was just a little less. I liked the idea as it would save me some money and also I really didn’t like living on my own. It was September 10th so I gave my notice and told them I would be out by the first. Jill and I became really good friends and we spent time together every day. A few night later we were downtown working on a Friday night and it was so busy, people everywhere and of course so many people in costume. The night was almost half over and I don’t think I had even made $20 yet and Jill was even having a slow night. I think every Superhero there has ever been was downtown and many more than one. I told Jill I needed to find a new costume or I wasn’t going to survive when she told me she was also thinking of changing her costume as we had seen 2 other Cat Woman that night.

The next day we were talking and she said she had an awesome idea for a costume one she had not seen downtown and new she could make a lot of money it was just that it really took two people to make this costume idea work. I was intrigued and asked more; she told me she bet we could both make $200 a night or more which really got my attention. I told her I was interested but remember my size as that has really affected my tips she just smiled and said my size would not be an issue and would actually help the costume. She told me she would tell me all about it tomorrow after she went and got the costumes and figured out if it would work. We went back downtown that night in our costumes and did a little better than the night before. Jill kept saying I can’t believe no one else has thought of my idea yet, I haven’t seen one other person wear this costume. I tried to get her to let me in on it but she just kept saying it would be a surprise. We stopped about 2 am tonight as she said she had to be up early to go get the costume and I should be at her place by 6 to try on my costume, actually after the first it would also be my place.

I got to Jill’s apartment at 6 and she told me to come in as she was almost ready. Jill finally came out and she had on this awesome showgirl costume, 4″ spiked heels, skimpy red sequence bikini bottoms, and a skimpy red sequence bikini top and was carrying a big feathered head dress which she say down. Her makeup was perfect including bright red lipstick. She really looked like a showgirl from one of the big hotel casinos shows. I just stood there and stared at her as she was so beautiful. I had always liked Jill from the day we met but seeing her this way I was in love and I guess I wasn’t just thinking it because in heard Jill say thank you, which is when I realized I had said it out loud. She was going to get a lot of tips tonight. I was so taken by her costume that I hadn’t even asked about my costume.

Jill took me into what would be my room and there on the bed was a matching costume. That’s when it hit me she wanted me to dress the same way as her which was impossible. In would look stupid and no one would want a picture with me. She smiled and said let’s just try it and with that she gave me a kiss on my lips leaving red lipstick on my lips. In a moment of weakness I agreed so into the bathroom and Jill gave me a cream to put all over my body which removed what little body hair I had. Now we were ready to start.

Now it was time to get dressed and she explained what I needed to do, well what she was going to help me with as we didn’t think I could do it on my own. This included hiding my male part between my legs. Now this was the first time Jill had seen me without clothes so I was a little embarrassed. It started with an ice pack to shrink things down and then she used a special tape and folded and pushed and tucked and in the end I had a smooth front even without clothes. I asked her how she knew how to do this and she told me she had gone and talked to a local drag queen to find out how to make me look female. Well it worked and I could even go to the bathroom if needed but I would be sitting down. I pulled on the bikini bottoms and they fit perfectly. Next we started on the top. She attached these little silicone jell like breasts to the outside of my chest, yes I had some flab on my chest which people call baby fat. Once the glue had dried she pulled it to the center and attached the little clip between them and I had small breast. I was amazed. Next came the bikini top which was tight and pulled them even more to the center increasing my breast size to almost a C cup. I was amazed but we were not done yet. She took out another item she called a silicone breast enhancer and stuffed them into the outside of the bikini top further pushing things in and up. I was now as big as her and looked just as good and realistic.

Standing next to her I had the body of a young girl and felt almost naked. Now she started on my hair which was a little long, down to my shoulders. Some curlers, hair spray and soon I had a very femeini6 hair style just maybe a little short but with the headdress it would look fine. Now it was time for my makeup. Now I have never worn makeup or even thought about dressing this way but I was kind of enjoying this. She put all kinds of makeup on my face, blush, mascara, eye shadow and finally the same red lipstick. The last thing was to paint my finger nails red and I was ready. I looked totally like a girl, not just a girl but a beautiful showgirl. I could not believe how I looked. It was finished with the same 4″ spiked heels and a little perfume. We stood in front of the mirror and we looked almost like sisters accept for the fact I had brown hair and Jill had longer Blonde hair. It was almost 9 so it was time to leave. I was so in a trance and couldn’t believe how I looked that I really didn’t think about it till we were outside getting into her car when a couple guys walked by and started hitting on us. I got scared and got in the car.

I told Jill I had changed my mind and wanted to go back inside the apartment and change. Jill calmed me down and talked me into going downtown and against my better judgment I did. We got downtown and started walking down the Freemont Experience. I was so scared as I felt like I was naked. I don’t know how woman can walk around with so little clothes on even though I love seeing them that way. We had only been there 15 minutes when several men came up and wanted pictures with us. We must have taken 20 pictures with them as a group one at a time, both of us together and alone. When it was done the 6 of them each gave us $10 each so we had made $60 in such a little time. Now that was incredible but I was still scared and uncomfortable having men put their arms around me.

We were a hit that night we took so many pictures and no one recognized us or thought we were anything other than 2 girls. As the night went by I relaxed and actually had a lot of fun. I even started to flirt with the people as I found that really helped with the tips. By 3 am I was ready to call it a night as I was really tired and my feet were hurting, I don’t know how woman wear such high heels all the time. Jill just said they get use to them. We dropped off our headdress in the car and then went to get something to eat. I was amazed as we got stopped 3 times just walking to the casino coffee shop for pictures. We drew a little attention in the coffee shop but no one said anything. We each counted our money and we each had almost $400. It was a really good night and I was so happy as I finally made a lot of money. I told Jill we were going to make a fortune doing this; she just smiled at me and said so that means you are willing to dress this way again? This caught me off guard as I had not fully thought through what I had said. I thought for a moment, it is no different than an actor playing a part in a movie. I told her yes I would as the money was too good to pass up. She said that was great but we could do better than so I should come by her place in the morning.

The next morning I got to her apartment and she took me in and helped me get ready again, the tucking and putting on the breast went a little faster this time and soon I looked just like a girl again. Jill handed me a hot pink bikini and told me to put it on. I asked her why and she said I was to pale and needed a tan. The next thing I knew we were both down by her pool laying out in the sun and yes we even went into the pool. It was all going well till a couple of her neighbors came over to talk to us. Jill introduced me and we all talked for a while, one of the ladies asked if we were sisters which caught me off guard although we did kind of look alike as Jill had done my makeup and hair like hers although my hair was shorter and brown. I looked at Jill not knowing what to say when Jill just smiled and said yes. I smiled at the thought that they thought I was her sister. We all spent the day at the pool and I got a nice tan.

Later Jill and I got back into our showgirl outfits and left for downtown again and I was a lot more relaxed going tonight as it went so well last night plus the day at the pool. We got downtown and immediately we had people who wanted pictures with us and not just men. We had another awesome night and I was really enjoying it as we were once again the stars downtown. We again made about $400. We had really figured out how to work it. Jill asked me to come over again the next day in the early afternoon.

The next day I got to Jill’s about 1 and Jill helped me get ready again but this time she gave me a short skirt and top to wear and we were off. Now this was different as we were just out as 2 girls and I didn’t see the reason. Dressing as a showgirl was to make money and the time at the pool was needed for a tan but what was this about. We stopped at a beauty salon. I asked her why and she just smiled, I was thinking about yesterday when they thought we were sister and I just wanted to see if we could make us look a little more alike. I thought for a moment and it sounded like a fun idea but I really didn’t think it through. I was shown to a seat and the lady trimmed my hair in the same style as Jill’s although it was shorter, then she put a cream in my hair. That’s when I realized she was dying my hair blonde to match Jill’s I was going to say something but at this point it was really too late. A half hour later I had beautiful blonde hair. Next we got a manicure and pedicure but it was more than just that. They gave me a beautiful set of acrylic nails that were now as long as Jill’s, about ½ long and bright red. We really did look like sisters. It was a fun day and now it was time to get ready and go back downtown. We had another great night and made lots of money.

The next few days went by fast and soon it was the end of the month and time for me to move in with Jill which brought another problem I had not thought of. All of Jill’s neighbors already knew me but as Jill’s sister. How could I move in with her as my male self? I brought this up to Jill and she thought for a moment. She got a smile on her face and told me I would just have to move in as her Sister. I looked at her and told her I couldn’t live full time like this and she just smiled and said you really have been for a while. You get up and come over here and become a girl till you go to bed each night you will just be getting ready a little earlier. Think about it we will get up and lay out by the pool during the day and then go downtown in the evening to make money it will be fine. I thought for a moment and she really was right and so I moved in with her as her sister and so starts my new way of life.