Trapped             by: Roger Thomas

 

It happened to me back in high school one Halloween evening, the day I will never forget when I was caught and couldn’t do anything about it. But that is jumping ahead so let me start at the beginning. I went to a private school when I was young that we really couldn't afford so I worked at the school as the janitor to pay my tuition.

It didn't take me long to notice that several of the girls didn’t take their bags home at night they just left them either by their desk or in the changing room. Well at first I was afraid to look in their bags because I just knew they would notice things weren't as they left them or someone might come in and find me going through these "girl" things. But pretty soon I realized that nobody ever came back to school after they left and that most of the stuff in the bags was just in there in no particular order and soon enough I started playing .

I started one day by looking in the changing room in the bags and I found a pair of colocks that fit me in one of the bags of course the rest of the stuff in there was of no use because it was just a "T" shirt and a pair of tennis shoes and I had those but what a moment, I finally was going to wear something that one of those girls had been wearing just a little earlier! WOW what a feeling I would look down and see my lower half and I couldn't believe it. It fit good and snug but not to tight and the only thing that didn’t look like a girl was that bulge and there was nothing I could do about it.

At first I wouldn't even go out of the room then I thought , nobody ever comes back to school. So I walked out of the room like this was what I was supposed to be wearing. I went back to work and started vacuuming the carpet in the classroom and all of a sudden I swore I heard a car door slam outside and I bolted right back to the girls changing room and took those colocks off and put my pants on so fast I’m surprised I didn’t rip one or the other, my heart was beating so fast and my face was hot and my ears were even burning then when I looked nobody was there. What a scare!

It was a few days before I went back to trying on other girls clothes and I found that there were many of the girls clothes that I could wear, some were tight some lose. Then one day it happened we were at an away ball game ( the whole school went to them) and when we got back it was after the normal time to dismiss school and most of the parents were there waiting to pick up their kids and most just got off the bus and went to their rides without even going in to the building. When I noticed this I immediately got exited because I knew there would be regular uniforms in the building! I thought everybody would never leave. They just kept hanging around and talking about the game but I was already starting to clean and notice that there were bags sitting around many of the girls desk. When I was sure everybody was gone I began to look in the different bags and find the clothes that fit. A skirt from one of the girls that I knew would be snug on me and then there were the other things that hadn't been left before, I found a slip in one bag it was to small for me but after pulling gently and working one side and then the other I was able to get it on, Oh what a feeling to have that on and it was slick and keeping me from making big steps then to feel the skirt slide over top of it. Then I had to do more snooping to find which tops would fit me since no one had left these before. And I searched every bag for a bra but no luck. I guess they didn’t bring a spare, I just had never thought of it before. But I did find shoes. I was trying to get their shoes on and everyone of them was to small until I came upon my best friends twin sister’s bag. I wont say she was a fat girl but she was big boned tall and had big feet. Her shoes fit me perfect! They even felt good and they were comfortable. I put her socks on and then her lace up dress loafers. It felt funny wearing socks that came to the bottom of my knee and to know that I was wearing Marion’s shoes. I found one of the blouses that fit me pretty good since I had no breast and had a heck of a time getting it zipped up in the back, now I know why girls are always asking (zip me up), But I finally got it. then I put on a vest. I was worried about getting the right clothes back in the right bag so I decided to put my pants in the bag that I got the skirt from and my shirt in the bag I got a blouse from and so on. I also thought this would keep me from making a quick run to the changing room and getting out of these clothes at the imagined sound of someone coming, I would have to go around and replace stuff as I got my own clothes. That way I would have to wear these clothes even longer! Then the thought hit me as I stood in front of a mirror to look at myself ,I cant get out of these clothes very quick anyway. This vest has several buttons then the blouse zips up the back and I don't know if I can reach the zipper to get it down and I had a heck of a time getting this slip on and the shoes are tied.

As I looked at myself in the mirror I couldn’t believe it. Everything fit, but then it should when you go through like your shopping and try on this and that it looked wonderful all except that one bulge that just wouldn't go away. I made up my mind that I was going to do the rest of the cleaning tonight dressed like this. NO MATTER WHAT! So I started and immediately wished I hadn't put that tight slip on and started to take it off then I thought ,no a real girl would just have to wear it. The I thought ,"It sure would be nice to have a bra and a wig". I believe if I had had them that night I would have went out. As I cleaned I kept thinking how it must be to be a real girl you put this on in the morning and leave the house, once you are out there is no not being seen or running to change clothes real quick before someone sees you. This would be what you wore until the day was over! I was sure wishing I had a bra and a wig so I would Know what the girls actually felt like. Even thought I didn't I still tried to act like a girl for the rest of the evening while I cleaned, I would try to sway my hips as I walked and feel the slip and skirt swinging and brushing my legs I would sit at some of the girls desk and smooth my skirt as I sat. Wow I wanted to just wear this forever! But every time I walked by a mirror there was this girl with my head and a nasty bulge in her skirt.

When I finally had to take it off and put my cloths back on I had some trouble remembering which bags my things were in and had to look around a bit to find them. When I got to my pants which were the last thing I took the skirt and slip off and pulled my pants on and it sure felt funny when the pants slid up my legs after not having anything on them. I sure didn’t want to step out of those clothes.

The next day at school I would almost blush when I spoke to the girls that I had wore their clothes just the night before and all day every time I would see Marion go by I would think to myself ( I wore your shoes and those tall socks last night) Then I would see Gail go by with here skirt swinging and just smile.

Mindy would sit and eat with me at lunch and I couldn't help but look at her and think (I can fit into your blouse but just barely).

Every day I wished for girls to leave their skirts and regular uniforms at school and go home in their p.e. clothes but almost always they would change out of their p.e. stuff and into uniforms before dismissal but from time to time they would leave their uniforms behind and I was like a kid in a candy shop!

One evening I was wearing their stuff around and the phone rang, it was my dad and I had to leave quickly because of a family deal I had forgotten about and I was late! I headed for the door as quick as I could and was getting in my car when I realized what I was wearing, OOPPSS I ran back into the building my face red and I was terrified that someone had seen me but they hadn’t and I was still late I changed as quickly as I could and put the clothes back into the bags they came out of but didn’t have time to fold them neatly. Well the next day at school the girls were all talking about how someone had been into their bags and ruffled things up they were not happy and all I could do was try not to look guilty. After that I really had to be careful and try to put stuff back neatly but from time to time they would still talk at the lunch table about they thought someone had been wearing their stuff and they would say stuff like "If I catch that bitch in my skirt she will wished she had just wore her own stuff" I had to laugh because they never would catch the bitch cause it wasn’t a bitch and I only done it when no one was there!

Then came Halloween day ! The principal said that we could dress up for Halloween instead of wearing our uniforms since it was a short day anyway because we had a girls volleyball game that day to all go to just after lunch. Well I sure wanted to dress up like a girl and I decided to do it so one night at home I told mom what I was planning and would she help me I told her I wanted to go all out if I were going to do it. She told me to go ahead and shave my legs now instead of waiting until the last minute so the rash from shaving would go away. It was still a week from Halloween but I did it ( I got a pretty good kick out of that anyway). Then just a few days before Halloween my Mom said she couldn't find the stuff like a wig to borrow and some big shoes and we couldn't afford to just buy it for one use and toss it so I just went as a cowboy thinking how much fun it would have been to go as a cowgirl.

WOW what a shock I got when Mindy Marion and Gail showed up for school!! They were all three dressed like hookers Gail which had always had short almost boyish hair had on a wig that hit her almost at her ass, Along with a slinky dress that was kind of long and low-cut. Marion was wearing a pantsuit which girls weren't allowed to wear on a normal school day and these magnificent high heel granny boots that zipped up the side instead of lacing up. And Mindy was wearing this DRESS!! It was solid black and looked like leather, struck her just barely above the knee and was more than straight I believe it was smaller at the bottom than it was at the hips, long sleeves, tall collar, zipped up the back and she had huge tits, She was normally flat as a board.

We all hung around eyeing the three and talking and someone ask Mindy about her new breast and she told us that she had an aunt that had breast cancer and had bought these breast-forms so she would look natural and that she had borrowed them bra and all because the dress needed them to fill it out, and fill it out they did. I couldn’t help but think "I could wear that"

Then the most amazing thing happened. We all got back from the game ,which our girls won , all the parents were waiting on the kids and all three of these girls went straight to their parents cars and left! I immediately got exited because I knew what they had left behind! The last car was barley out of sight when I quit cleaning and went to the changing room and got the three bags and started in. I was so glad I had already shaved my legs and the rash was gone. There in Marion's bag were "The Shoes" along with a pair of pantyhose. I had never found pantyhose before. So I took off all my clothes including my underwear which I had never done because I’d never had anything else to put on, Put the pantyhose on, and if you don't remember the feeling the first time you ever put pantyhose on shaved legs then I feel sorry for you.

Then I went ahead and put the high heeled boots on and tried to zip them up but they were tighter than her normal shoes and I really had to put some pressure on the zipper but they finally came up. The first time having high heels on! Wow I would walk from one side of the room to the other then giggle and look at my legs in pantyhose and high heels and wish that bulge would go away but I was so exited that it wasn’t going anywhere Then I reached for "the dress" and sure enough there under the dress in the bag was a bra and two breast-forms. I was almost shaking I was so exited. I fumbled with getting the bra fastened and had to try each breast-form and see which one went in which side. Then as I leaned to pick up the dress I felt the weight of the breast and the bra holding them and got extremely exited. I stepped into the dress and had a little trouble pulling it up past my hips because the waist was small and I knew if it was tight on Mindy I might not even get it on but my gosh it was so sexy I was going to try like hell. I got my arms in the sleeves and started trying to zip it up. I would suck my stomach in and pull, the zipper would move a little. God I wish I had someone to zip me up I said. Then I would let my breath out all the way and zip a little bit further, I finally got it past the waist part and then it went pretty good from there all the way up to the high collar which almost came to my chin and that gave me a feeling of ... I don’t know how to describe it maybe like it was part of me because it started so high that it felt like it was just there and you really couldn't see where it started it was just there. Then I tried to walk over to Gail’s bag to get the wig. Wow I found out that you don’t just take off in high heels and an almost tapered dress you have to gently move. I got the wig and kind of straightened it up where it had been in the bag and put it on. I couldn’t believe it, there I was in nothing but girls clothes and 100% complete! I took my time and walked downstairs to the girls restroom which had the only full length mirror in the building.

Then it happened! I heard footsteps in the basement! Not a car outside, Not someone upstairs that had just come in the building, This was not my mind playing a trick on me, There was someone in the basement, No wait there was more than one someone at least two! My heart stopped and jumped up into my throat. My mouth went dry instantly. How did they get into the building without me hearing them ? What were they doing there? I had to get out of these clothes and now! I had no other clothes there with me though but I couldn’t let someone see me wearing these clothes! I took the wig off and tossed it into one of the stalls, then reached for the zipper on one of the boots and found out you cant lift your foot up when you are wearing a tight skirt! I bent over and got hold of the zipper, it wouldn’t move PERIOD I got the other one and it wouldn’t move either! I grabbed the zipper at the back of my neck and it wouldn't move! I had to be dreaming they had to move but try as I might they would not budge! I couldn't get the dress off, I couldn’t get the shoes off, I couldn’t get the pantyhose off and there for sure was no way to get those huge breast out of this dress. I listened. Those were girls voices out there! Why didn’t I go to the boys restroom and I could just wait for them to leave? Gosh how I wished I were any where but right here right now.

Then I thought I hear a girl call my name. Brian hello. I wasn’t about to answer. Then another girl called for me, Brian we are waiting for you. I still wasn’t going to say anything and let them know where I was! Then I recognized Mindy. Hey Brian come out of the bathroom and let us see you we need to ask you something. I heard them all giggle. I finally had to do something because they knew where I was so I said " What do you need I’m a little busy right now". And Gail replied "We were wondering how our clothes fit you". Oh shit they knew but how! "What" I said. "Come on out and let us look at you or were coming in" Marion replied. Just then I happened to look in the mirror and that bulge was gone with no hint of it ever being there, I guess that I was so terrified at least one of us got to go hide! As I was trying the zippers again Mindy said "The zippers in that dress and those shoes have to have a key to get them down, We are going to see you in those clothes". I was terrified, trapped, no way out. I picked up the wig and started walking out like a whipped puppy. When I walked through the door the three of them started giggling, I know I had to be blood red because my face was hot. Then one of them said "Don’t slouch strut them tit’s girl!" "Put the wig back on " Another one said. Then Marion said "We have got to get your makeup done and nails painted." I said Just help me get these zippers undone" Gail replied "no you are going to the Halloween party with us." "No way " I said "No you don't understand you don’t have a choice we are not letting you out of those clothes until after the party." Mindy said "You have been getting in our clothes for a long time and tonight its payback" "What " I squeaked " Oh don’t even pretend" Mindy yelled "It doesn't take a genius to figure out who had been getting into our clothes since every time we left them here at school they were moved and smelling like cologne the next morning, Your cologne!" Oh shit (Busted) Then Marion spoke up "So tonight you are going to get to wear them for all to see, My dad got me those zippers at the place where he works they are industrial zippers that you have to insert a key into them before they will come down, and don't even think about breaking them . It’s no use you are in those clothes until we let you out and you are going to the Halloween party tonight"

 

 

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