Crossdressing For The Team

I grew in to the world of crossdressing occasionally reading short stories about forced feminization. Their plots typically had the high school jocks made to pay for their male chauvinistic attitude by getting dressed up to compete to be homecoming queen. Alternatively a young man is caught rummaging through his aunt’s clothes. As punishment she makes him wear her old clothes –– all summer. I always took those stories with a grain of salt. So when a new friend told me about his early years I was both amazed and skeptical but he proved to be very convincing.  I think the saying goes, “unbelievable but true.”

Let’s call her Geri. I first was contacted by a man named Gerry responding to an ad I’d placed on craigslist. I’m not the story here so suffice it to say that Gerry’s writing and his persistence in responding convinced me to go to dinner with him one Saturday evening.

As we chatted at the restaurant Gerry opened up to me about some fascinating and strange aspects of his life. During our conversation he asked how I had started crossdressing. I launched in to a long story that in retrospect probably wasn’t interesting to him at all because at one point when I stopped to reflect he said, “for me I started when I was about 10. Or more accurately my mother started me.”

“Come again?” I asked as even I lost interest in my story. “Are you in to dressing?”

“A bit,” he said, “but not like you.”

“What do you mean your mother started you?”

“My dad was in the Canadian military so we moved around from base to base. He was not an officer so he didn’t earn a lot of money. My mom worked on the side as a seamstress making and re-sizing dresses for the ladies on the bases. When she needed a mannequin she got me to put on the dresses. I couldn’t complain. She needed me. She demanded it of me.  And after a while I liked it.”

“That would have been my dream job,” I joked, “I would have much preferred it to my paper route. So that turned you in to a crossdresser?” I continued.

“Not exactly but I think it helped.”

“Ten is a very impressionable age,” I offered.

“That’s nothing to what my mother made me do a few years later,” Gerry continued, “We were stationed in Germany at the time. The base had some great recreational facilities. I had become a big fan of Jacques Cousteau so I wanted to become a scuba diver. The problem was the scuba club met only once a week. I was a little young for scuba certification and I knew I needed to become a stronger swimmer, anyway. My domineering mother had the perfect solution. She told me I would join her synchronized swimming group which met several times a week. I would learn better swimming and breathing techniques and no, I wouldn’t have to wear the costume; this was only for training and fitness.

“I became a regular with their group and because I was still young and small I became their favorite for the lifts.”

I began to see where this was heading and I had my doubts.  “If you were just in it for the training why would they build a routine around you? Who would they use in the competitions?”

“I’m sure my mother knew all along who they were going to use and she had probably told her team mates not to worry, come the time I would be willing to wear the costume and make up just as I had been willing to be her mannequin.”

I was going to ask a question about peer reaction but Gerry beat me to it. “I was relatively new to that base and I didn’t have a lot of friends but the ones I did were all military brats so they were used to having at least one domineering parent. It was not unusual for a kid to be doing something he didn’t want to do but had to when a parent insisted. My friends were understanding and sympathetic.

“As the training progressed the team and I were getting quite good and I could see that the synchro training was helping my regular swimming and my snorkeling.

“Then it came the time for the meet. Eight other teams were coming from all over Europe. My mom started on to me about how important I was to the team and how we all had to look the same. She would not hear of me dropping out and she insisted I had to wear the same bathing costume and makeup as the rest of the team.”

“Did you have long hair that you could tie up?”  I asked thinking of the girls I’d seen in the recent Olympics.

“Not an issue. In those days all the teams wore swim caps. I had no problem with that.”

“My guess was that you were in the competition.”

“I was mortified when I saw the swim suit was actually a two-piece suit.  So I put the suit on and knew right away I couldn’t go out on the swim deck.”

“Were you shy? Did you look too pretty?” I asked.

“Neither,” he replied, “my mom and her friend came in to the male change room to do my makeup. That’s when she discovered my problem. As soon as I put on the bathing suit I got a flaming great erection that wouldn’t go away. She took one look at it and ‘WHACK’, she slapped it with her open hand. Her friend gave her heck for doing it but it had the desired effect and I was able to tuck my tool discretely out of sight.”

I winced in sympathetic pain. “The show went on?” I asked.

“The show went on and as I recall we won second or third prize. We had to stay around to the end in costume to get our prize. I think the judges and most of the audience were none the wiser that the little tween in our group was actually a boy. A number of the teams had small young girls on the team just for the lifts. I fit right in that way.”

“So all was well that ended well. Did you get to keep the bikini?”

“The adventure wasn’t over yet. I had to go back to the male change room to put on my street clothes.  I also enjoyed a few last looks at myself in the mirror. As the synchro event was over, a group of soldiers came in for their training session. When they saw this little lady boy in a girl’s bathing suit and makeup prancing around in front of a full length mirror they had a conniption. I thought they would kill me with derision. Did I mention that my erection had come back? Well it went away pretty quickly.

“Luckily a sergeant came in and called them off. His wife was member of our team and he had been sent in to see what was taking me so long. He saved me from total humiliation and put the soldiers on report.

“After the competition I swam a bit more with the team but soon dad was re-posted to Canada and my synchro career came to an end. Yes, I kept the suit and from time to time my mom would slip me some other fem clothing, mostly cast offs from her clients.”

“So you didn’t mention in our exchanges that you are into crossdressing?”

“The funny thing is that I’m not. At least not to the extent you are. I enjoy wearing some feminine apparel for love making but that’s about it.”

“Are you wearing anything now?” I asked as I reached under the table to feel his thigh.

“Let’s head back to the hotel and I’ll show you,” came the reply.

The rest, as they say, is history.

Tags: fantasy, featured

Category: Transgender Fun & Entertainment