It started when I was sixteen. I guess that's how it works for everyone, right? The girl next door; a hot, college student who was the object of my dreams, was into community theater. We'd spend afternoons helping her with her plays. Sometimes she had the boys play female roles. She even dressed us up. I guess something about it just felt right. Something stuck.
Of course, a grown man in a dress isn't socially acceptable. And it's not like I ever wanted to BE a woman. I just got a charge out of dressing up. And so I gravitated toward something more discreet, like panties. At first, I'd just wear them at home. But I slowly got the courage to wear them out in public beneath my clothes. Just on weekends at first.
But by the time I hit my mid-twenties, it was a daily thing. I owned boxers, but it wasn't unusual for me to go days or even weeks without wearing them. I'd go to work in panties.
I'd shared my secret with a few serious girlfriends and most of them were tolerant, although confused. But mostly it was my own private thing. I traveled a lot for work and dreaded one day being asked to open my luggage in an airport and having some security guard see a suitcase filled with silky, lacy panties. But it didn't stop me.
On the road, I mostly kept to myself. But on a long project, I always fell into patterns; the same hotel, the same restaurants, the same gym. And that's how I met Maya. She was an assistant manager at the upscale hotel where I'd been staying for months. Our interaction was pretty limited, but over time we seemed to get to know each other. And there was something there. But I wouldn't have acted on it. It just seemed tacky to hit on someone while they were working.
And so I didn't think about it much. Not until a Friday night toward the end of the project. It was a chance meeting. A few colleagues and I had gone out for drinks at a bar near the hotel. I didn't even see her. Maya approached me.
She knew my name, of course. She was still dressed for work in a tailored gray skirt suit that tightly gripped her body, black heels, black stockings, and a silky black blouse. Her long, dark hair was even still up pinned up conservatively. We talked briefly, then she excused herself to leave me with my group. One by one the guys decided to leave and get some rest. Some had flights to catch. But I lingered in the bar.
Maya was with a group of co-workers and friends. And they were slowly leaving, too. It was getting late when I started toward the bathroom and passed her at the bar. She grabbed my arm and pulled me over. She'd obviously had a few drinks and was openly flirty. I couldn't pull myself away.
We talked about nothing in particular at first. The weather. Some sports on TV. But the conversation grew flirty. Somehow we ended up alone and sitting in a back booth.
I was the one who kissed her. The conversation had lulled and I did it without thinking about it. Her soft lips parted and took my tongue. She kissed back hungrily. My hand went instantly to her thighs. And she started rubbing my cock through my slacks.
"I can't go back to the hotel," she said.
I nodded, thinking the evening was over.
"You want to come to my place?" she asked.
There was just a moment where I hesitated. I was dressed in a button-down shirt and dark slacks. But underneath it all, I had on panties. They weren't ornate or lacy. Just plain black silk. But I knew there was little chance I could play them off as briefs.
"I'm not sure..." I started to say.
Maya rubbed her hand over my crotch again. My dick was rock hard.
And I caved.
Ten minutes later we were in an apartment making out like high school kids. Only two things were running through my brain; how much I wanted to fuck her, and whether I could turn out all the lights first.
We moved around the room recklessly. I had my hand under her skirt rubbing her bare thigh. I pulled away just a second to flick off a lamp.
I pushed her onto her back on the couch. I got two buttons open on her blouse and buried my face in her luscious cleavage. With my free hand, I rubbed her hot, wet pussy through her soaked satin panties.
"Take me to bed and fuck me," she whispered.
I lifted her and she guided me down the hall. We started to undress one another in the dark room. I pulled off her blazer as she unbuttoned my shirt. I unzipped her skirt and it slid down her long, fit legs and hit the floor. She was working on my belt. The moment of truth. She pressed her lips to mine as my pants slid down. I started to discreetly slide out of the panties, hoping she wouldn't notice.