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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.

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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.