"Caught" Crossdressing at a Gentlemen's Club

I don’t know if this qualifies as being “caught” since it was sort of on purpose. I was “caught” by a dancer at a gentlemen’s club.

I decided to be a little dangerous one night. I often wear lingerie under my clothes at work, but decided to step it up a notch. Before heading out to the club on Saturday night, I put on my sexy best. Under my black jeans and short-sleeve button-up, I put on a satiny, black camisole, a favorite pair of Victoria’s Secret lacy black panties, a garter and black stockings.

I knew it was risky going to one of these clubs crossdressed, but I’ve gone to work dressed like this a hundred times, so I figured a dark gentlemen’s club would be inconspicuous. Plus, I doubted any of the patrons would be paying much attention to another lone guy. Anyway it was a fantasy and a thrill in that setting to be wearing full lingerie watching the dancers in theirs.

I sat down towards the back so no one would be sitting behind me and ordered a beer. It wasn’t long before a sexy blonde dancer named Skyler came my way. She was thin and pretty with black stockings and a shiny hot pink bikini top and bottom. She has smallish, champagne-glass b****** and a tasteful tattoo of a scheming mermaid on her right arm. We talked a bit. She went on stage and did her thing and I tipped her. She asked if I wanted a private dance, and I said, yes. Pretty routine up to that point.

We went back into the semi-private area. There was no one else in the room. A curtain covered most of the door to the room. It gave the feeling of privacy but didn't block the view from the hallway that led to all the rooms.

I couldn’t keep my hands off of her stockings and she encouraged me, putting my hands on her legs and her bottom. While she was dancing up on me, running her hands up and down my chest and legs, she paused, very briefly as her hands passed over the latches of the garter on my thighs. She moved on.

"You smell nice," said Skyler. I was wearing Kate Spade perfume, and all of my daily hygiene, from my body wash to my deodorant, are women's brands. A few seconds later she started to unbutton my shirt. The shirt has snappy buttons, and people just can’t resist unsnapping them.

To be honest, I hadn’t really considered this entirely, yet, so I took a heavy breath. I didn’t say anything and didn’t have any intention of stopping her since no one else was in the room, but obviously I stiffened up (no pun intended). Skyler put her hand inside my shirt and then paused as she felt the satiny soft material, then looked me in the eye and said, “Hmm, what’s this?”

I stammered.

She looked down at the lace top edge of the cami, and with a sly grin said, “You like to dress up a little bit, huh?” Then, she started rubbing my chest through my cami. Oh gawd, that feeling!

All I could say was, “Is this okay?”

Skyler said, “I think it’s sexy. What else are you wearing under there?” She rested her hand on my belt. I just nodded, my heart racing.

She unbuckled my belt, unbuttoned and unzipped. My lacy panties peeked out from the top. “Oh my, those are cute. Is there more?”

I said, “Yes, but is it okay?”

“We’ll be careful,” she said. “Ronny never comes back here when we’re slow like this unless we ask. The other girls will use other rooms until we get busy, and we’ve been dead all night.”

At that she pulled my jeans down to my knees exposing my thigh highs and I thought I might pass out from ecstasy at this point. “Stockings AND a garter belt! Wow, you really went all out, huh? Do you like to dress up a lot? What else do you have for me?”

I told her my toenails were painted, too. (They almost always are.) Skyler immediately slid off my loafers. “Cute!” she squeaked.

A new song started and she stood up, left me sitting on the couch with my shirt wide open and my pants down to my knees, one shoe off. “Keep going,” she asked.

I said, yes, obviously… Haha. Shut up and take my money!

She danced all over me and that’s as close to c****** in my panties as I’ve ever come without actually stroking. She went on like that for another song or so (who knows, I was in heaven and my heart was going crazy). Towards the end, someone passed by the curtain, another dancer leading another guy to the back. Both looked into the booth and both probably had a great view even though Skyler was on top of me.

She said, “We better be careful,” and nodded at my pants. I pulled them up and she started buttoning my top. “Shame,” she said, “I was having fun. Do you want to go to the VIP room? No interruptions in there.”

We talked about it, but it was going to end up being more than I could afford. I would have paid every cent, but wasn’t prepared. She was cool about it, though. I asked her if I could come back, and she said she hoped I would. I said I’d be ready for the VIP room.

It wasn’t long after that the pandemic shut everything down, but I’ll be heading back there to see Skyler as soon as all this is over. Yet another fantasy spoiled by the Rona.

Dec 7, 2020

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  • Wow, that’s pretty sweet. Hope you can make it back there again!

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