The Terrible Teens

My first pair of pantyhose

If all has proceeded as planned I will be on my way to Arizona for gender reassignment surgery in a few days. Your thoughts and prayers would be a most welcome blessing to me at this time. No doubt it will be a while before I’ll be able to check any electronic communication, so without further ado – the continuation of my exploration a few months back into whether I’m a transsexual.

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.

En Femme Style

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…

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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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.
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Michille Lynn
Michille Lynn(@buttercup)
5 years ago

I still get a little paranoid when shopping for my girly things. I’m getting better but in my head I think everyone is watching me wondering what the he– is he doing.

Vanessa-Marie Villarreal
Vanessa-Marie Villarreal(@vanessa-marie)
5 years ago

In my teens I bought my feminine finery with my allowance money, only to have my Grandmother and my Aunt snoop around in my room while I was school and ridicule me later.

12 years ago

Yeah, tell me about it – it's so unfortunate that in "serving" the transgender community they're also ripping folks off. Glad you realized this early on and found some places that work for you. Woman come in all shapres and sizes, and there are stores that cater quite well to them 🙂

12 years ago

What I remember is smoking not one but two cigarettes, trying to work up the nerve to go into a boutique that specialized in drag and CD wear. I was 49; I'd not crossdressed for 32 years, and I was "borrowing" from mom and the three sisters back then.

One trip was enough. The prices were outrageous enough that my next trips were to Sears and Ross.

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