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Crossdressing for the first time
🕑 Added 2022-08-18 12:37:37 +0000 UTCMy life at school was fairly uneventful. I wasn't brilliant academically. I wasn't a talented sportsman, actor or musician. I wasn't one of the popular children. I wasn't in physical fear from bullying, although there was a lot of teasing, name calling and 'jokes' that were funny for everyone else. It was one particular practical joke that went much further than usual, which happened towards the end of my time there that changed my view on life.
It was a Wednesday. That year I didn't particularly like Wednesdays, because my timetable started with Physical Education. I was, and still am, skinny. Back in my school days I was teased on a regular basis because of my slimness, my lack of body hair and my high pitched voice. Regular taunts were the accusation that I must shave my legs for them to be so smooth and I was therefore a girl; that my voice was too high-pitched for a boy and I was therefore a girl and, rather embarrassingly, that my cock was too small to be a cock and I was therefore a girl. You get the picture. Changing for PE was always an ordeal. I tried to hide in a corner and hope I remained unnoticed.
This summer Wednesday, the last before we left, was an occasion when I didn't go unnoticed. I was half changed when several of the boys grabbed me. Held down in the middle of the floor I was stripped completely. Once before this had happened and I had been thrown into the corridor, right in front of a group of girls and their teacher. This time I felt them redressing me. Finished they allowed me to stand up. Every one laughed. They had dressed me in a pink bra, with lace trim and a matching pair of panties. I looked down. The panties were pulled up tight, my cock invisible between my legs; even to my eyes I looked like a girl in the panties.
The PE teacher, Mr. Graham appeared. "What's going on?" he demanded.
"There's a girl in here Sir!" called out Mark, the ringleader of my attackers, and the others joined in. They were all part of Mr. Graham's favourite group so I knew I would get a telling off. He always took their side. He looked me up and down. "You're in the wrong changing room, young lady, come with me."
He took me roughly by the arm and marched me out of the changing room. Luckily, this time the corridor was empty. He knocked on the girls changing room door. Miss Stone appeared and she too looked me up and down.
"One of your new girls has used the wrong changing room. I don't think she has the correct kit. Can you sort her out Miss Stone?" he said with a chuckle.
"Of course, Mr. Graham, come with me you silly girl!" she said and then she took me by the arm and marched me into the girls changing room.
Under different circumstances I might have enjoyed the view that awaited me. The girls from my year group in the process of getting changed and some were just in their bra and panties, like me. They exhibited no surprise or alarm at my presence, when Miss Stone attracted their attention.
"Does anyone know this girls name?" she asked.
Some of the girls clearly had no idea who I was and some were about to say that I was actually a boy, but the quicker-witted ones caught on to the joke. They called out suggestions like 'Pansy' or 'Sissy'. Others joined in calling out girlish names that were like my own name, which is Joseph by the way, such as 'Josie', 'Joanna' or 'Josephine'. Miss Stone settled on Josephine.
"Josephine, do you have your kit?"
"No, Miss" I mumbled. She directed a girl to get me kit from the lost property box and another to fetch two small bean-bags from the equipment store.
Miss stuffed the bean bags into the cups of the bra, they filled them nicely and molded to the shape of the cups. Then I had to squeeze into a pair of maroon PE-knickers. They gripped me tightly, making my cock even less visible and hugging the cheeks of my bum.
"Look at her cute bum" I heard someone say. "I'd love long thin legs like hers" said another. Next I put on the maroon PE skirt. It was the type that flapped over at the front, where it was flat, and then had pleats all round the back. . Then I donned a white short-sleeved blouse. This too was quite tight serving to emphasize the thinness of my waist and the padding in my bra. Glancing in a mirror I saw that I looked like a quite shapely girl! White ankle socks and a pair of pink trimmed trainers went on my feet and someone found two pink ribbons to tie my longish hair into two bunches.
Before I knew it Miss had ordered me, as Josephine, to join the other girls on the tennis courts. To get there we had to walk past the boys warming up for their athletics. They had an idea of what to expect. The nastier girls made sure I had to walk right by them and then tripped me up, making me flash my knickers at them, to a chorus of jeers.
"Just ignore them Josephine!" called Miss Stone, thus ensuring that they all knew what I was being called. I began to feel very miserable.
The lesson began, split up into fours I was with Donna, Jenny and Marion. They were three of the nicer girls and they weren't horrid to me. I actually began to enjoy the lesson. The tennis was gentle, so we were able to have a bit of a chat and enjoy the weather. The girls even warned me that, when I picked the tennis balls up I should bend at the knee and not at the waist to avoid flashing my knickers! I found my new look rather fetching. My legs didn't look skinny as they usually did and my thin waist looked appropriate. To my surprise I even found the skirt fun to wear! I was almost disappointed when Miss said the lesson was over and I had to walk past the waiting boys back to the changing room.
Instinctively I headed for the boys changing rooms, but Miss redirected me.
"You really must learn your way around!" she said. "I've spoken to Mr. Graham and he says he can't find any of your clothes in the boy's room so he has asked me to kit you out for the rest of the day. Won't that be nice?" She smiled but not in a nasty way.
Confused I waited by her office. She emerged with a bundle of clothes and a pair of shoes. "Change into these then bring your PE kit back here."
Obediently I made my way back into the girls changing room. My tennis partners were just leaving. They asked what I was doing and I explained. They offered to help me get ready.
Soon I was wearing the summer uniform, consisting of a maroon cardigan over a summer dress in a maroon gingham pattern. The dress was a bit tight, hugging my body rather more than it did the others and it was also a bit short. The cardigan fitted fine. On my feet, over the white ankle socks I had on a pair of black, sensible, but undeniably feminine shoes complete with a small heel!
Donna assured me that I looked fine. Together we returned to Miss Stone's office.
"Well Josephine you look very nice. Here is a note for your teachers that will explain the way you have chosen to dress. Off you go and enjoy your break."
I nearly began to argue. Chosen to dress indeed, but I didn't meekly accepting my fate.
Round the corner we ran into some of the boys who had started all of this.
As I expected they started to jeer.
"Look at Josephine!" Mark cried out, emphasizing my new girls name. "I'll bet the little sissy is still wearing the panties."
Mark immediately reached for the hem of my dress and tried to raise it up above my waist. I was pretty much frozen with embarrassment, yet strangely excited, as I held my hem down. To my surprise Mark's girlfriend Tracey can over and thumped him.
"Don't you go looking up another girl's skirt!" She yelled, "Come on Josie, we'll look after you" she added and I was whisked away by Tracey and her friends.
This wasn't much of a comfort to me as Tracey and her friends were just as likely to be horrid to me as Mark and his friends. My fears grew as they escorted me in the girls' toilets. "If you wanna dress like us you've gotta have the full experience Josie." I stood there as they gave me a make-over. They applied some red lipstick, pale blue eye-shadow and even mascara. I was like a doll they were playing with, showing no resistance at all. Next I was squirted with some perfume that smelt vaguely of flowers.
Marion had waited for me outside, too worried to leave but too frightened to come inside.
'Hurry, Josie, we've English next.' She said, "The others are already there."
As we walked to the classroom I realized something rather odd. I knew that the day was going to be like no other, but, surprisingly, I didn't care. I loved it. I loved it all. The feel the soft dress clinging to my body, the taste of the cherry lipstick, the scent of the cheap perfume and the snug caress of the panties.
I gave the note from Miss Stone to my English teacher. She read it, muttered "This is most unusual" and then proceeded to treat me as she did the other girls in the room. She even let me sit next to Marion and we worked happily together. Once again the time flew by and I was sad when the bell sounded for the end of the lesson.
At lunch I went around with Marion, Jenny and Donna. They were so nice to me, chatting to me more then they ever did normally. They were much friendlier towards me after just one morning than any of my usual friends.
However, just before the end of lunch Tracey sent one of her gang to fetch me. I didn't want to mess things up for my new friends so I went without fuss, promising them I would be ok and that I would see them later.
As Sharon led me round to behind the changing rooms, I doubted my promise. I suspected that I would not be ok. Behind the changing rooms was not somewhere I would ever venture alone. As I feared Tracey and Mark were both there with an assortment of hangers-on.
Mark was whispering to one of his gang, Tony. He seemed unhappy at what he was being told to do, but not wishing to upset Mark he shrugged his shoulders and walked over towards me, standing right in front of me. I hadn't worked out what was happening until he unzipped his fly and took out his cock.
"Tony ain't got a girlfriend at the moment so you'll do 'til he gets one. Give him a blow job you slut!" Mark's statement was followed by gasps and sniggers. Helpfully two of Sharon's mates pushed me to my knees. I looked at the limp cock dangling before me. They were going to make the most of my new status as a girl.
I considered trying to resist, but I realized that it would only create more trouble for me. My hands trembled as I wrapped my fingers around his. Shyly, at first, I allowed my fingers to explore, feeling its girth, his wiry pubes and tightening sack. As I felt his cock hardening I realized that I was in control. Somehow, even in my position, I felt comfortable, confident and in control. Inside my head I was accepting myself as a girl and allowing myself to do this, ignoring the tingling, worried feeling in my stomach. I made a ring with my fingers and circled his shaft easing my hand along the warm skin. I felt him twitch and he let out a gasp at my touch, increasing my feel of control.
However my sense of control was short lived, as was the experience. Having his cock stroked in front of his so-called mates was too much for Tony and he came suddenly, all over my face. How everyone laughed at us, at him for coming so quickly and at me for having a cum-covered face. I think he was more humiliated than me. I knew that my face would wipe clean, which it did with a minimum of fuss. I even managed not to taste any of the sticky goo, although strangely, I was curious as too how it would taste. However Tony was now forever marked as the boy who came oh so quickly, with out even being sucked!
The warning bell for the end of lunch sounded and the crowd dispersed. I went to meet Marion and Jenny who, after helping me wash my face in the girl's loo, went with me to the library for our study period.
We sat amongst the books, passing notes to each other about the events of lunchtime. I found myself altering my handwriting to a more feminine style, in imitation of their writing. Again the feeling of friendship was evident and the hour passed all too quickly. On the way to our final lessons Miss Stone stopped me in the corridor.
"There you are Josephine; I have been looking for you. Come with me." She strode off down the corridor and I followed obediently, wondering what lay in store for me.
'In store' turned out to be an appropriate choice of words as she led me into the PE equipment store, where Mr. Graham was waiting. He greeted me in a relaxed and friendly way.
"Hello Josephine."
"Hello Sir." I replied.
Miss Stone stood next to him and I was a little surprised when she slipped an arm around his waist and they shared a small hug.
"I understand you've had an eventful day Josephine" she said, "Tell us about it."
"How do you mean, you know what happened this morning." I stalled.
"Yes but afterwards, tell us what did it feel like, spending the day as a girl?" she prompted.
That was the big question. Dare I tell them how much I had enjoyed the feel of the clothes, from the snug fitting knickers to the feminine heeled shoes and the dress that hugged my thighs so alluringly? Would it be wise to admit that I had enjoyed being treated as a girl, both the friendship of other girls and the helpless feeling as I was behind the gym faced by a cock? Would the truth spoil their enjoyment of their practical joke, I wondered?
"I can tell by the smile on your face that you have enjoyed it Josephine, but I need to hear you say it." Miss Stone prompted.
"Yes Miss Stone, I enjoyed it. Every minute of the day." I was surprised to hear myself say. Emboldened I added "I liked being a girl."
To my surprise she moved over and hugged me. "That's fantastic Josephine" she cried. "I am so pleased that you had a good time!"
"Tell us about being with Tony behind the gym" said Mr. Graham.
I hadn't realized that they knew about this, but I told them, honestly, about my feelings of nervousness and then power, all mixed with curiosity, as well as the details of who did what to whom. They seemed to enjoy hearing all the details. Miss Stone asked if I would have sucked Tony's cock if he hadn't cum. I confessed that I would have and felt a flutter in my tummy as I did. The next question surprised me.
"Would you lick a girl's pussy while you were Josephine?"
I thought for a bit and decided that I would and told her so. Her next question surprised me even more.
"Would you lick mine, right here, right now?"
I nodded wordlessly. She led me over to a big crash mat, like the ones high-jumpers land on. She reached up under her short tennis skirt and pulled her knickers slowly down across her long tanned legs. She lay down and beckoned me over, indicating that I should kneel between her legs, facing her and then bend forward. I did as I was told and tentatively flicked my tongue across her pussy lips. The musky smell was intoxicating as was the slightly metallic taste which greeted my tongue. Sometimes she guided me either by word, moan or by moving my head physically. Every now and again I felt the soft smooth skin of her thighs, long and muscular, sliding against my ears.
Then I felt my dress being lifted up, over my bum, until it was around my waist. I realized at once that Mr. Graham was getting into the act! I felt him stroke my bum and then begin to pull my knickers down, exposing me. I paused for a moment taken by surprise, but Miss Stone pushed my head down and told me to continue licking and sucking.
At first he continued stroking my bum, but soon I could feel him pulling my cheeks apart and running a finger along my bum crack and round my tight hole. As he did this I continued licking enjoying the taste and the feeling of giving pleasure to Miss Stone. Also, to my surprise I could feel my cock hardening. I was lost in the sea of sensations.
Miss Stone came first, moaning contentedly, pushing my face hard into her pussy and gripping me with her thighs as she did. Mr. Graham took this as his cue to push a little harder with the finger that had been circling my bum-hole. It expanded to allow his finger to slide in a little. The feeling wasn't unpleasant, but it was overwhelming and my cock jerked and squirted as I came.
I collapsed and lay for a moment in the sticky pool. Then I got up and tried to redress and clean my self with a tissue
"If you'd like, Josephine, you could dress up again and do all sorts of fun stuff. We have a friend, Kim, who will help you and we know loads of cool places we could go. Please say you'd like to!" said Miss Stone as she replaced her knickers.
I looked at them in astonishment. This was clearly something more than just a practical joke. They had set the whole thing up hoping I would react as I had done. I noticed that Mr. Graham was having difficulty hiding the fact that he had an erection of his own and to my surprise I found myself wondering what it would have been like if he had used his cock and not his finger! There was only one way to find out.
"Miss Stone. Mr. Graham." I looked at each of them in turn, smiling as I did. "I would love to have the chance to be Josephine again and I would love to spend more time with you both."
I showered and changed back into my normal clothes, ending Josephine's first, and only, day at school. However I knew that I would soon get the chance to find out more about the side of myself she represented.
Please tell me if you liked my story and would like to hear more of Josephine's adventures!
