Picking up a Crossdresser in a Bar
This happened about 20 years ago. The basic events are completely true, but in those days I drank a lot, so I don't remember many of the details. For the purposes of a good story, I made up a few things to fill in the blanks in my memory.
It was a weekend, and my wife had taken the k**s to visit her father 400 miles away. I was alone at the house, and I knew an opportunity when I saw it. At the time we lived in a small city, and there was a gay bar in town that advertised a weekly drag show on Saturday night. I have a thing for crossdressers, and had wanted to check it out for some time.
I wanted to make a good impression, so I cleaned up and dressed decently – button-down shirt, nice jeans, shoes. I had a few drinks at the house to loosen myself up a little. I waited until about the time my wife usually retired for the night, just in case she called. Then I drove to the gay bar, arriving about the time the drag show was scheduled to start. I knew the club crowd tended towards late hours, and I didn't want to be hanging around an empty place. I paid admission and got a drink from the bar. After a while the show started. If you've been to one of these you know what they're like – wildly overdressed and heavily-made-up drag queens lip-synching to pop songs. The music leans heavily to the diva genre, everything from Barbra Streisand to Donna Summer. I've been to a few over the years. One time at a show in Philadelphia I bought a drink for one of the competitors and wound up sucking her off in the dressing room (true story.)
I watched a number of performers as the crowd in the club began to grow. After a while I noticed two younger crossdressers at the bar. They were in their 20s or early 30s, slender, dressed in sexy outfits, chatting and laughing while their eyes checked the room. They were not quite passable, but very sexy. Both were dark-haired, with natural hair long enough to pass for feminine if styled that way. One was wearing a red minidress, with full-length arms and a skirt a few inches below her ass. The other was all in black, with a scarf d****d loosely over her shoulders. The one in red turned as I stared at them and caught my eye, giving a little smile.
I waited and ordered another drink. After a few minutes red dress turned my way again, her eyes holding mine a little longer this time, her smile larger. I returned the smile, then she turned back to her friend.
There was an empty spot next to her at the bar, so I wandered over. She noticed I had moved there and turned to me and said, “Hi.” I introduced myself, giving a false name I used on such occasions. She said her name was Dana and introduced me to her friend, who called herself Cathy. We watched the show together, making small talk between performers. She told me the two of them had driven over from a town about 60 miles away. At one point she leaned in and put her hand on my shoulder while she spoke, and the possibilities began to make my head swim even more than the drinks. Not long after I had my arm around her waist, and she had snuggled close. Even in heels, she was no taller than me.
I was mostly talking to Dana, and after I'd been with them for a little while another guy started chatting with Cathy, taking a stool on the other side of her. He and I were buying the two of them drinks, we were all watching the show together. I wasn't introduced to him, and we didn't say much to each other.
The show ended about 1 a.m., and the two CDs put their heads together for a few minutes. Then Dana turned to me and told me the other guy had invited them to his townhouse to continue the party, and I was welcome to come along. She laid her hand on my arm as she told me this, and I knew things were good.
Dana rode with me in my car, while Cathy rode with the other guy. We followed them to the townhome and into the house. He poured us all a drink, then he and Cathy disappeared upstairs. There was a futon in the living room, and Dana and I were left sitting on that. We chatted for a minute about the drag show, then I leaned in and kissed her. She put her arms around me and returned the kiss. I ran my hands over her body, and she reached between my legs, stroking my thigh, then driving straight for my hard cock. She moaned as she felt my rod.
I stood up and loosened my belt. She opened my zipper and pushed my jeans and underwear down to get to my cock. It's not gigantic, but at 7” (not making that up) it's acceptable. I stood between her legs as she sucked and kissed it. I put my hands on her shoulders, then her head as I pushed deep into her mouth. She wasn't deep-throating, but still handled a lot of the meat very well. I was hot to see more of her, so I pulled her up to stand in front of me. I kissed her as I ran my hands under her skirt and up to her ass. I had noticed the dress zipped up, so I undid the zipper and stepped back a little as she peeled it off her arms and it pooled at her feet. She stepped out of it and kicked off her heels. She wore only a thong and matching bra under it. I pulled her too me and kissed her some more, and she began unbuttoning my shirt. I moved her back to sit on the futon, and continued undressing. Upstairs I could hear Cathy and her man groaning in pleasure.
I'd never owned a futon, and, while I knew they turned into a bed, didn't know how. Dana did, and had it spread flat in the time it took me to get naked. She was lying back, caressing her thighs and smiling, when I came to her. We kissed while I caressed her body. She was erect, with a small penis – maybe 3”, and I stroked it through the front of her thong panties, then got between her legs to rub my larger organ against hers. She moaned into my mouth as we kissed, then I rolled over on my back to give her access to my cock.
She got on her knees and quickly took me in her mouth, her hand caressing my balls. She was kneeling sideways to me, and I could easily reach her ass. I caressed her cheeks and ran my fingertips down between them, pulling the thong away to get access to her hole. I reached farther to get to her balls, but she wasn't interested in that, and wiggled her butt to warn me away. It was then that I understood she wanted to be totally the woman, and didn't want me paying attention to her organs. She sucked for a few minutes, and I was as hard as I'd ever been in my life. She made her way up my body, kissing my belly and nipples, then my lips. Lying on top of me, she whispered that she wanted me inside her. Upstairs, as if to complement her desire, we could hear Cathy rhythmically groaning as her hole was pounded.
Dana said she had lube in her purse, but didn't have any condoms. Neither did I (which wasn't very smart of me.) She said Cathy had some in her purse, which she'd left on the stairs, and she retrieved one from there. She opened the foil and rolled it onto my cock, then lubed me from her small bottle. Turning her back to me, she stripped her thong down to the top of her thighs and got on hands and knees, wiping some more lube into her hole. She spread her legs and I knelt behind her, wiping my lubed prick against her tiny rosebud.
Putting her head down, she reached back with both hands and spread her cheeks. I pressed forward and slid inside. God, it was tight! She jerked from pain, and I stopped for a moment. Then she started to push back onto me. She moaned as she took more and more of me. Holding her hips, I began going in and out, finally reaching full depth, tickling her ass with my pubic hair. I stopped to look down at her hole, stretched obscenely around my rod, then began slowly sliding out until just the head was inside her.
I fucked her slowly at first, but I knew I wouldn't last very long, and then my body took over. After a few minutes I was pounding full-length into her tight asshole. I pushed her down onto her belly, and savaged her with hard thrusts, holding up my weight on my hands and slamming my hips against her ass. She moaned with each thrust, and I'm sure our friends upstairs heard her. Then I reached it, and slamming into her body I lay flat on her back as my cum pulsed out into the condom.
We lay like that for a few minutes. I kissed her cheek and ear as we regained our breath. My cock began to soften, and I rolled off and lay on my back as I withdrew. She kissed me, then lay on her back next to me. When I'd recovered, I padded off to the bathroom, flushed the condom, and cleaned up with a towel. By now it was about 3 a.m., and I didn't want to fall asleep there. My wife was an early riser, and would probably be calling around 7 or 8. I explained to Dana that I had to get up early, and began dressing. She covered herself with a throw that had been on the futon, and smiled up at me as I got ready to go. I leaned down and kissed her, and told her I might see her again at the drag show, then went on my way.
I never had another chance to hit that drag show, and I never saw her again.
It was a weekend, and my wife had taken the k**s to visit her father 400 miles away. I was alone at the house, and I knew an opportunity when I saw it. At the time we lived in a small city, and there was a gay bar in town that advertised a weekly drag show on Saturday night. I have a thing for crossdressers, and had wanted to check it out for some time.
I wanted to make a good impression, so I cleaned up and dressed decently – button-down shirt, nice jeans, shoes. I had a few drinks at the house to loosen myself up a little. I waited until about the time my wife usually retired for the night, just in case she called. Then I drove to the gay bar, arriving about the time the drag show was scheduled to start. I knew the club crowd tended towards late hours, and I didn't want to be hanging around an empty place. I paid admission and got a drink from the bar. After a while the show started. If you've been to one of these you know what they're like – wildly overdressed and heavily-made-up drag queens lip-synching to pop songs. The music leans heavily to the diva genre, everything from Barbra Streisand to Donna Summer. I've been to a few over the years. One time at a show in Philadelphia I bought a drink for one of the competitors and wound up sucking her off in the dressing room (true story.)
I watched a number of performers as the crowd in the club began to grow. After a while I noticed two younger crossdressers at the bar. They were in their 20s or early 30s, slender, dressed in sexy outfits, chatting and laughing while their eyes checked the room. They were not quite passable, but very sexy. Both were dark-haired, with natural hair long enough to pass for feminine if styled that way. One was wearing a red minidress, with full-length arms and a skirt a few inches below her ass. The other was all in black, with a scarf d****d loosely over her shoulders. The one in red turned as I stared at them and caught my eye, giving a little smile.
I waited and ordered another drink. After a few minutes red dress turned my way again, her eyes holding mine a little longer this time, her smile larger. I returned the smile, then she turned back to her friend.
There was an empty spot next to her at the bar, so I wandered over. She noticed I had moved there and turned to me and said, “Hi.” I introduced myself, giving a false name I used on such occasions. She said her name was Dana and introduced me to her friend, who called herself Cathy. We watched the show together, making small talk between performers. She told me the two of them had driven over from a town about 60 miles away. At one point she leaned in and put her hand on my shoulder while she spoke, and the possibilities began to make my head swim even more than the drinks. Not long after I had my arm around her waist, and she had snuggled close. Even in heels, she was no taller than me.
I was mostly talking to Dana, and after I'd been with them for a little while another guy started chatting with Cathy, taking a stool on the other side of her. He and I were buying the two of them drinks, we were all watching the show together. I wasn't introduced to him, and we didn't say much to each other.
The show ended about 1 a.m., and the two CDs put their heads together for a few minutes. Then Dana turned to me and told me the other guy had invited them to his townhouse to continue the party, and I was welcome to come along. She laid her hand on my arm as she told me this, and I knew things were good.
Dana rode with me in my car, while Cathy rode with the other guy. We followed them to the townhome and into the house. He poured us all a drink, then he and Cathy disappeared upstairs. There was a futon in the living room, and Dana and I were left sitting on that. We chatted for a minute about the drag show, then I leaned in and kissed her. She put her arms around me and returned the kiss. I ran my hands over her body, and she reached between my legs, stroking my thigh, then driving straight for my hard cock. She moaned as she felt my rod.
I stood up and loosened my belt. She opened my zipper and pushed my jeans and underwear down to get to my cock. It's not gigantic, but at 7” (not making that up) it's acceptable. I stood between her legs as she sucked and kissed it. I put my hands on her shoulders, then her head as I pushed deep into her mouth. She wasn't deep-throating, but still handled a lot of the meat very well. I was hot to see more of her, so I pulled her up to stand in front of me. I kissed her as I ran my hands under her skirt and up to her ass. I had noticed the dress zipped up, so I undid the zipper and stepped back a little as she peeled it off her arms and it pooled at her feet. She stepped out of it and kicked off her heels. She wore only a thong and matching bra under it. I pulled her too me and kissed her some more, and she began unbuttoning my shirt. I moved her back to sit on the futon, and continued undressing. Upstairs I could hear Cathy and her man groaning in pleasure.
I'd never owned a futon, and, while I knew they turned into a bed, didn't know how. Dana did, and had it spread flat in the time it took me to get naked. She was lying back, caressing her thighs and smiling, when I came to her. We kissed while I caressed her body. She was erect, with a small penis – maybe 3”, and I stroked it through the front of her thong panties, then got between her legs to rub my larger organ against hers. She moaned into my mouth as we kissed, then I rolled over on my back to give her access to my cock.
She got on her knees and quickly took me in her mouth, her hand caressing my balls. She was kneeling sideways to me, and I could easily reach her ass. I caressed her cheeks and ran my fingertips down between them, pulling the thong away to get access to her hole. I reached farther to get to her balls, but she wasn't interested in that, and wiggled her butt to warn me away. It was then that I understood she wanted to be totally the woman, and didn't want me paying attention to her organs. She sucked for a few minutes, and I was as hard as I'd ever been in my life. She made her way up my body, kissing my belly and nipples, then my lips. Lying on top of me, she whispered that she wanted me inside her. Upstairs, as if to complement her desire, we could hear Cathy rhythmically groaning as her hole was pounded.
Dana said she had lube in her purse, but didn't have any condoms. Neither did I (which wasn't very smart of me.) She said Cathy had some in her purse, which she'd left on the stairs, and she retrieved one from there. She opened the foil and rolled it onto my cock, then lubed me from her small bottle. Turning her back to me, she stripped her thong down to the top of her thighs and got on hands and knees, wiping some more lube into her hole. She spread her legs and I knelt behind her, wiping my lubed prick against her tiny rosebud.
Putting her head down, she reached back with both hands and spread her cheeks. I pressed forward and slid inside. God, it was tight! She jerked from pain, and I stopped for a moment. Then she started to push back onto me. She moaned as she took more and more of me. Holding her hips, I began going in and out, finally reaching full depth, tickling her ass with my pubic hair. I stopped to look down at her hole, stretched obscenely around my rod, then began slowly sliding out until just the head was inside her.
I fucked her slowly at first, but I knew I wouldn't last very long, and then my body took over. After a few minutes I was pounding full-length into her tight asshole. I pushed her down onto her belly, and savaged her with hard thrusts, holding up my weight on my hands and slamming my hips against her ass. She moaned with each thrust, and I'm sure our friends upstairs heard her. Then I reached it, and slamming into her body I lay flat on her back as my cum pulsed out into the condom.
We lay like that for a few minutes. I kissed her cheek and ear as we regained our breath. My cock began to soften, and I rolled off and lay on my back as I withdrew. She kissed me, then lay on her back next to me. When I'd recovered, I padded off to the bathroom, flushed the condom, and cleaned up with a towel. By now it was about 3 a.m., and I didn't want to fall asleep there. My wife was an early riser, and would probably be calling around 7 or 8. I explained to Dana that I had to get up early, and began dressing. She covered herself with a throw that had been on the futon, and smiled up at me as I got ready to go. I leaned down and kissed her, and told her I might see her again at the drag show, then went on my way.
I never had another chance to hit that drag show, and I never saw her again.
5年前
