Transsexual teenage trauma

We resume the story with our intrepid heroine about to enter her teen years and experience the joy of her first period, breast growth and discovering boys. In your mind you should now hear the scratching sound as the DJ hastily lifts the needle off an old LP record just before the crowd turns around to stare. Our unfortunate heroine had none of those delights to look forward to, but rather the twin tyrannies of massive height expansion and needless hair growth in places entirely unbecoming.

Not that I knew what to expect at the time, or even that what was happening was wrong. It was just what everyone had told me was supposed to happen. I never had the sense of identifying strongly as a girl when young – though honestly never really felt that I fit in as a boy. I was too big to beat up, too shy to find and too smart to get into trouble at school.

The computer in my room was the perfect distraction from all my social and romantic ineptness – it was something I could understand even as I failed to understand myself and my relationship with others. As it turns out this distraction would pay a key part in my future welfare – but we’ve jumped to far ahead already…

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My First Pair of Pantyhose

When I was 12 or 13 I found myself obsessed with the idea of purchasing and wearing my own pair of pantyhose. I have no idea why that would be a good idea, and tried for many weeks to push the thought from my mind. Yet after fighting the anticipation for so long I finally broke down, and found both the courage and opportunity to purchase my first pair of pantyhose.

My mom, brother and I were out shopping and I found occasion to “browse the shops by myself”. I told my mom I’d meet her back at the car in a while, and off I went. I made a beeline to a store I knew sold pantyhose, but that was on the other end of the shopping center from where my mom and brother were shopping. I could feel my heart drumming a tune of nervous ecstasy in my chest as I circled the aisle where the object of my obsession was kept.

After what seemed like hours of mustering my courage I approached the forbidden temple – and panicked! What size was I? Where was the color I was looking for? My pending sweat gave me little opportunity to think straight and I grabbed for the first pair I thought might have a chance of fitting, hastily made my way to the cashier and then out the store.

I had a few more minutes left, and I could wait no longer – off I rushed to the public bathroom to put on my new stockings, only to discover that they were gray! Damnit. I imagined my legs encased by sexy black stockings, not gray. Not gray! It was too late though, the deed was done and I was half naked in a bathroom stall trying to figure out how to put on pantyhose when someone banged on the door.

My heart dropped to the floor, “How could this be happening?!”. I was about to hastily scramble and get dressed – sans stockings – when the person identified themselves as the cleaner. I mumbled something and pulled those stockings on as fast as I was able to. Anxious beads of sweat were dripping down my face as I realized I was late meeting my mom, and rushed out to the car.

I could feel the pantyhose brushing against my pant legs, and in the car ride home I kept pushing down my socks to feel the texture of these divine encasings, riding the thrill of a desire achieved for the rest of the afternoon.

I’ve never felt such a heightened level of excitement at purchasing woman’s clothes before. Perhaps the energy was sexual, but this was before I had any experience or knowledge of what a sexual experience would entail. I was a naively innocent pre-pubescent boy who had re-discovered the wonderful world of femininity.

I won’t bore you with all the details as to how this pair of pantyhose caused me so much joy and tension. Wearing them, sleeping in them, stressing because I had to wash them without being discovered, finding a place to hide them so noone would discover them – as it turns out my calculator case was a fabulous hiding place 🙂

This was also the period where I began to derive sexual pleasure from woman’s clothes in one way or another. I won’t dwell on this, since just mentioning it has me blushing behind the luminescent screen of my laptop and anyway, this aspect is no longer an important part of my journey. I must admit eagerly looking forward to the time when the correct hormones are flowing through my body and such desires are under the controlling care of my mental and emotional faculties.

What do you recall about your first shopping experience for feminine finery?

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21 Comments
  1. Lila 8 years ago

    Although I’d been aware of my fascination for dressing in feminine clothing for nearly as long as I can remember (being tempted by my sister’s dresses is an early memory from age 5 or so), my first cross-dressing experiences were in my early teens. Fortunately, I was frequently alone at home, and able to borrow my mother’s and younger sister’s clothing without them knowing (or maybe they did know, and just didn’t say anything). I remember the first time was my sister’s ballet leotard with her denim skirt. Later, I tried more elaborate outfits, with panties and a training bra, sheer pantyhose, a slip, my mother’s gold sandals with two-inch heels (my feet were already too big for any of her closed-heel/toes shoes), one of my sister’s formal dresses (or a skirt/blouse combo), clip-on earrings and other jewelry, and lipstick (I hadn’t figured out any other makeup yet, but I still get a wonderful rush when I apply lipstick as the finishing touch after putting on primer / foundation / powder / blush / mascara / eye-liner & -shadow). I was never caught (borrowing clothes without permission is the only thing about my cross-dressing experiences I’m *ashamed* of), but there were a couple times I could hear someone walking into the house as I was frantically replacing items in the lingerie drawer.

    A few years later, after my first girlfriend confessed having a bisexual inclination, I admitted to my urges, and we wound up shopping for lingerie together (sometimes for her, sometimes for me) to wear underneath when I put on her clothes. I think my first solo shopping experience was a pair of modest black patent leather pumps (which I still have, along with most of the late-80s lingerie I bought with my long-since-ex) at Target, late on a weeknight, so I could try them on for size without too many people around (before I figured out that 95% of size 9.5 shoes will fit me OK).

    I’ve gone through on/off periods of cross-dressing since then (which seems to be very “on” right now, at the moment I’m wearing a black and white floral Ann Taylor sundress – it’s hot in the Bay Area today), but I love browsing through racks of dresses, skirts, and other pretty garments (and shoes, and jewelry, and makeup, and fragrance, and purses, and …). Even during “off” times, girlfriends have been impressed that I never complained about them taking too long while shopping.

  2. tryitoncesyd 5 years ago

    I started crossdressing when I Was 13 I remember trying on a pair off my mums knickers out of curiosity that was, but after I pulled up those knickers I experienced the most wonderful feelings I’d never felt
    so good in my whole life this was great, the thing was were was I going to get some women’s underwear from so I started to pinch them off friends and family im not proud of this but I could not stop wearing women’s knickers I wore them for school nearly getting court a few times but nothing stopped me after a while I was trying on every thing I could, I got so obsessed with dressing up as a girl I would tell lies to my friends(girlfriend) that my brother had taken all my normal briefs and left me with none and shamefully it worked they would give me a clean pair of knickers to wear every day I was in heaven I felt fantastic now next stage was to wear more female items.

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