The Gigolo Chronicles V Cherrie
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I Was Wearing Panties When I Met Her free porn video
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.
And then she went for my cock. I could tell right away that she'd noticed the satin material. Her eyes darted down. She squinted a bit.
"Are those...?" she started.
And then Maya went for a lamp by her bed. She flicked it on.
The two of us stood staring at one another in the room. She was still in her black blouse and stockings. I could see just a hint of her panties.
And I was exposed. My hard cock struggled against the thin, satin fabric of my black panties.
"You're wearing panties?" she said.
I couldn't even make words. I was wondering if there was any way to pull this off and still get laid. Or at least not get outed to the entire hotel staff.
Maya just gave a snicker. She walked into an open door, a large walk-in closet.
When she was the same out she had something in her hand.
"If you're going to do it, do it sexy," she said. "Don't be a prude in your granny panties."
She tossed what was in her hands my way. I caught a pair of silky black panties.
"Go to the bathroom," Maya said. "Put them on."
Slightly puzzled, but not looking to argue, I went to the bathroom and quickly stripped out of my own panties.
Hers were also black satin, but sexier. On each side of my hard cock were two sheer panels. The legs and waist were each trimmed with a half-inch band of black lace.
I walked back into the bedroom nervously.
Maya was on the bed. The light was still on. Her blouse was now completely open. Her tits were straining to pop free of a lacy black bra. The damp panties she'd had on were nowhere to be seen. I could see her neatly trimmed bush between her thighs.
"I like it," she said. "Sexy. I like how your cock looks. Turn around."
I turned around to show off my ass and she praised me some more.
"Just something missing," she said.
When she re-emerged she told me to sit on the bed.
Maya dropped to her knees in front of me. She kissed my cock through the panties. Then pulled the gusset of the panties aside so it sprang free from a leg hole.
She put both her arms around me. And then Maya started sucking my cock as she dressed me in a pretty, lacy black and white patterned garter belt.
She pulled away long enough to guide a stocking onto my left foot. And then swirled her tongue around the head of my dick while she rolled it up. She followed with the right.
She started tugging my cock while she sucked it.
"Cum in my mouth," she said.
I couldn't help but obey. I felt my cock spasm and unload between her soft, plump lips. She didn't miss a drop.
Afterward, Maya sat on the floor catching her breath. She took my cock and slid it back into the panties. Then she took the garter belt and attached it to the stockings she'd put on me earlier.
"Stand up," she told me. "I want to see you."
I did as she asked, standing and walking around the room. Already I was getting hard again.
"You're so fucking sexy, aren't you?" she said.
Her words were making me even harder.
"Fuck me while you're dressed like that," she commanded.
Maya stripped out of every stitch of clothing. Her body was fantastic. She went to the bed and got on her hands and knees.
I contemplated taking the panties off, but then I just slid the gusset aside as she'd done earlier.
I got between her thighs and plunged into her hot, wet pussy.
"Harder," she said almost instantly. "Don't be a fucking sissy."
I grabbed her hips and started plowing into her cunt. I loved the way I felt in stockings. I loved seeing my cock peek out from the panties and get buried in her hot little hole.
"Fuck me harder," Maya kept commanding. "Dominate me."
Each time she said it made me hotter. I wrapped an arm around her waist and pulled her tight to me. I put the other in her hair and held on for balance. I started pounding with everything I had. She moaned and groaned and could tell she was going to climax.
"HARDER," she said one more time.
I pulled back the hand from her waist, slapped her ass, thrust, and she just exploded. He turned into a quivering mess and her knees started to wobble. I just kept fucking until once again I needed to blow, and then I pulled out and shot my sticky load on her ass.
We collapsed in a pile, caught our breath without speaking, and then fucked again; the panties and stockings still on me.
At the end of the night, I dozed off. Still, all dressed up. With Maya rubbing my tired cock through the soft satin fabric.
Makenna
- 21.09.2022
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- Crossdressing
