Being unemployed leads to a surprise   Leave a comment

Being unemployed leads to a surprise

By Toni Girl

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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.

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