TG - College
Becoming Lexi 1
I was a "typical" crossdresser growing up. First started taking girl's underwear from the laundry hanper and wearing it at home at age 9 or 10. I didn't understand why, but it felt nice. Tall and blonde and not too "thick" I was able to wear my sister's or mother's clothes until age 12 or so. My parents discovered my stash once but didn't say anything, and I purged every once in a while. Later I'd steal a bra from a friend's laundry pile, panties from another, and even a one-piece bathing suit from a neighbor.
At 14 or so I started dressing more often for the sexual thrill. Purchased a sun dress and some other girl's clothes at a thrift shop, a pair of flats, and got the courage to buy a pair of panty hose at a department store in an adjacent town. Stole a MaidenForm C cup bra from a friend's laundry basket and experimented with making falsies. Tried balloons filled with water, or bird seed. Eventually I got some very large balloons, doubled them up, and filled them with water so they fit the bra cups but had some weight and even "jiggle." Then I scored a blonde wig at a Halloween shop.
By 16 I was a slender 5'10, with blonde hair and blue eyes. Started dressing up completely during the summer in the two hours when no one else was home, practiced applying makeup after watching YouTube videos. Then I had to carefully remove any traces before the family got home after five. Got a little bolder and would walk out to the mail box to check for mail, scurrying back inside if any cars came by.
The summer before college I got a job as a life guard, and that's when I got to know Brian. He was older than me, mid-20's, the Lifeguard Supervisor during the summer , teacher during the school year, and had a serious girlfriend. And, as it turned out - he was bi.
The community lake where we worked had to keep staff there overnight to keep out any after hours swimmers. This meant we had the place to ourselves unless someone snuck in, which was rare. The junior lifeguards had to have a Senior guard or Supervisor present, so sometimes I had this duty with Brian. We stayed up until 11pm, then slept on cots in the guard shack.
He was friendly without being creepy, and we sat around most of the time and told stories. He was a lot more experienced with girls than I, and told tales of his many conquests. He occasionally made reference to how a guy had approached him at some random place, but that didn't really interest me. He also watched porn movies regularly and detailed the plots and action. Then he mentioned a movie starring a "Transvestite" and from my questions it was probably obvious to him that was something I was interested in.
By mid summer he'd invite me to go to movies together when they closed the lake due to storms, or if his girlfriend was working at night. Mostly new movies at first, until we ran out of them. He made a lot more money than me so at some point he also started paying for me.
The turning point of my summer was when he took me to an alternative theater for a screening of "Desert Hearts" a classic film about the Lesbian love affair of a divorced teacher and a young woman. At one point Cay leans into the car during a rainstorm to kiss the reluctant Vivian for the first time. Later when we talked about the movie I told him I identified with Vivian in a way. "Oh, what way is that?" I blushed bright red.
Not long after he surprised me one rainy afternoon by taking me to another alternative theater for "The Crying Game." I didn't know anything about it, and was as surprised as anyone to learn Dil was transgender. There had been clues in the club scenes all along.
We were quiet for a while on the way home, then Brian started asking me what I thought about the movie. He explained that there was quite a crossdresser scene in Boston, that there were night clubs with performers just like it, and "It's usually the straight guys that hit on the crossdressers. Have you ever crossdressed?"
"Well, a few times growing up."
"Oh, when was the last time?"
"Um, actually, last month."
After a week or two we also began drinking during our overnight sessions. This was a strict no-no, but there was never anyone around to check on us. Some of the other guards were having parties, skinny dipping at night with friends, etc.
One night when I was quite buzzed he raised the question of sexual fantasies. I told him how I had always wanted to be a girl, strutting around in tight jeans and heels, tossing my long blonde hair, feeling my breasts bounce with every step, and being admired. And being desired and made love to. When I asked him he said, "I'm too embarrassed."
But then he got up and walked over to the Lost and Found. There were lots of little girl items there, but nothing much for teens or older. So then he opened the Lifequard supplies and pulled out a brand new woman's one piece Guard suit.
"Here," he said, "It's a present. Try it on!"
My head was spinning from liquor and excitement. I went into the bathroom and ditched my tshirt, shorts and underwear for the silky smooth suit. It fit pretty well, not too tight, though a little short in the torso. The result was that it pulled up on the bottom of the suit, flattening out my bulge and lifting my butt. It was intoxicating while I admired myself in the mirror. But I had some major tan lines on my legs, and the bra cups were empty. Self conscious, I put my shorts back on and returned.
"Wow" he said, "If fits great. Why the shorts?"
I blushed bright red and said, "tan lines."
But oh my god did I love the feeling! Any excuse to get up and walk around I took, to feel the tightness of the suit around my butt, how it seemed to hug my waist, even the feel of straps over my shoulders and the suggestion of breasts from the bra cups. I was in heaven and my penis was hard like it had never been before. ! He teased me that "I could make you wear that on duty." Just the idea made me hot and bothered.
I took the suit off before the morning crew came in and hid it in my bag. Took it home and washed it about 10 times in so it would have the faded look of a veteran, instead of the bright orange of a rookie. It took a few weeks of sun in the back yard to tan my upper legs.