It was quite a few years before I moved forward on the panty-wearing sissy front. I had graduated high school and started college before anything really happened. At this point, I lived in a dorm and had even more access to all sorts of weird porn with zero parental supervision (I did have a roommate I had to sneak around, though). Videos gave way to stories which gave way to message boards (who else misses the early millennium?). Panties shared the stage with humiliation, which shifted pretty heavily into forced feminization.
While I didn’t get a lot of traction into a pantied lifestyle, only having a few minor experiences since my friend’s sister’s panties (wearing a pair of a friend’s hot mom’s panties, and wearing a high school friend’s hot pink panties during her birthday party, come to mind (...I might be fucked in the head)), I did begin getting a lot of traction with girls. It was strange; one day I was a socially awkward nerd (albeit with some banging abs), and the next I was the thoughtful, well spoken—if offbeat—college student (with some banging abs). All of a sudden, I found myself both attracting girls, and being able to talk to them. It wasn’t long before I had a similarly offbeat girlfriend.
This girlfriend, it turns out, always wondered what I would look like in drag. The first few times she brought it up, I put up token resistance, dissuading her efforts, as I didn’t want to seem too eager. Eventually, however, I “caved-in.”
She jumped at the chance pretty-well immediately, picking out a dress (a red-cocktail affair), and a pair of knee-high leather boots. Then, came the question I never thought I’d hear:
“Do you want some panties?”
I felt my heart give a single, hard beat that I felt through my ears. Here it was, the opportunity I always dreamed of. Did I want some panties? Yes, of course I did! My whole life had been leading to this moment, submitting myself to the feminization of a hot, college co-ed. I wanted her panties more than I wanted goddamn oxygen, but I opted to play it cool.
“It’s whatever you want. It’s your day.”
She cocked her head, and looked at me sideways, speaking in a voice between playful and irritated, “Yeah, but do you want them?”
My brain screamed “YES!” so loud I was afraid she’d hear through my skull. However, I was either too smart or too stupid for my own good.
“It’s however you want to do it.”
“Fine, then, keep what you have on.”
My heart sank, but I knew it was a gamble when I answered. It wasn’t a complete wash, because, as I mentioned, I got to get feminized by a hot coed. If I was smart (fat chance), I might be able to spin this into a slightly more regular thing. I had to make it fun; I had to make it interesting.
The dress fit tightly (shock), and the bust-line framed my chest. Unfortunately, there was no time for grooming, so I had a patch of chest hair peeking over. Also, my feet were too big for the boots (another disappointment), but she compensated by giving me a feather boa.
After she had finished zipping up the back of my dress, I turned towards her, leaning in for a “Haha, just kidding, but seriously, can I get away with this?" kiss.
She just pushed me back and said, “Nope. This isn’t a fetish thing.” I didn't push the issue (yet), and submitted to her will.
What happened next was a series of cabaret-style pictures with her digital camera (hard to pull off in a one-room dorm room). Nothing too exciting, nothing too erotic. Mostly, she just wanted a taste of how I’d look in drag.
I imagine I looked like a moderately hairy dude wearing a dress and waving a feather boa (with banging abs). When she had had enough of the photo shoot, she invited me onto her bed to look at the pictures.
I moved in for another “Haha, but maybe?” kiss.
I got rebuffed again.
“What are doing? This isn’t a thing for me.”
I left it at that, sad as I was to do so.
We flipped through the pictures, I took off her dress, put my own clothes back on, and that was that. I never got another chance to get feminized with her, and the relationship only lasted a few months. It was fun while it lasted, and we both look on the early days fondly, but we wanted two different things. I wanted long-term, she didn’t. It happens.
But, I always remember how I felt when she asked it.
“Do you want some panties?”
Yes. Always.
