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.
Posted February 16, 2016 by missjames64 in A how to post, Author Elizabeth James, Caught with consequence
Tagged with crossdress, crossdresser, crossdressing, Free, story, t-girl
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.