Confession and testament of a crossdresser
- 4 years ago
- 21
- 0
My Date With A Crossdresser free porn video
A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.
We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.
Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or would prefer to wait in the room while she finished dressing. I told her I would like to wait in the room with her.
She had just finished showering and shaving, and was nude. She must have been feeling sexy, because she asked if I would like to fuck her as she was. I like my dates to be as femme as possible, so I told her I'd like to wait until she was dressed. She had several sexy outfits ready to put on, and she asked me which I would prefer. I chose one that showed her great legs and hot ass to good effect, and she began putting on makeup. I enjoyed watching her make herself up and get dressed, and I would occasionally run my hand over her shoulder or leg, or rub one of her nipples, which turned her on very much.
She put on a sexy black spandex dress with a black bra and panties, and a metallic red wig. When she was fully dressed, she smiled and asked if I thought she looked sexy. I smiled back and told her she did, and said that I couldn't wait to fuck her. I was already getting hard just looking at her, and when she knelt down and unzipped my pants, my cock jumped out. She ran her tongue over the head, and said that my precum tasted wonderful. I took her head in my hands and slid my cock into her mouth, and she went to work on it with her tongue while her hands rubbed the shaft and cupped my balls.
She gave me five minutes of a terrific blowjob, then said that she couldn't wait any more and wanted to feel my cock inside her. I put on a condom and told her to lie on the edge of the bed with her ass in the air. I pulled down her panties, put some lube on my middle finger, and worked it into her ass while she moaned and said how good it felt. With her panties down around her knees and the skirt of her dress pushed up to her waist, I began working my cock inside of her. In between gasps and moans, she told me how thick my cock was and how great it felt.
She told me it had been over a year since her last fuck, so I went slow at first, easing my cock in, then pulling out again when she asked. But over the next few minutes, I was able to bury it deeper and deeper into her ass, until I finally had it in balls-deep. I had my hands on her hips, and I fucked her faster and faster until I couldn't hold back any more and I came.
I continued to slowly fuck her until my cock went limp, and I pulled out, took off the condom, and threw it in the trash. She slumped down onto the bed, and she looked so good there with her skirt up and her panties down that I was sorry I couldn't fuck her again right away.
Instead, I laid down on the bed beside her and began running my hands over her ass, back, and shoulders. She turned her head to face me and said that my hands felt very nice, and asked if I would kiss her. I did, and for a while we held each other while I kissed her and massaged her shoulders.
She asked me if I had to go, and I told her that I didn't. I told her that she looked so hot and sexy that I wanted to show her off, and I asked her if she would like to go out to eat. She was shy at first, but eventually she agreed, and we both straightened ourselves out and left the room. She said there was a Denny's within walking distance, and asked if that would be all right, and I told her it would.
We had our arms around each other as we walked across the motel parking lot and down to the street. It was late at night, but from time to time a car would pass by, and when it did I would stop walking and take her in my arms and kiss her while my hands ran across her back and ass. She told me she had never been out while dressed, but being with me and having me kiss her in public made her feel like a sexy woman.
Inside the Denny's, there was a couple in their 20s eating at one table who looked up when we entered. The woman turned back after a moment, but the man stared at my date for a couple of seconds before looking away. I gave her another lingering kiss before leading her to a booth in the corner. My back was to the other couple, but my date could see them, and she told me that the man kept looking up at her.
A server came and got our order, and he also kept staring at my date. She smiled at him and licked her lips, and he had to tear himself away to look at me and ask for my order. By the time he left, I was getting hard again, and I asked my date if she was in the mood for something hot. She said she was, so I asked her to get down under the table and blow me again. She sat still for a moment, then smiled a wicked smile and slid down off her seat.
I spread my legs for her, and she quickly unzipped my pants and had my cock out. She started blowing me, and she was still at it when the server came back with our drinks. When he saw my date blowing me, he set our drinks down on the table, then unzipped his pants and pulled his own cock out. My date let my own cock go and went down on the server. I looked back to see what the other couple was doing, but they had finished and left. It was just the three of us.
I told my date that I wanted to fuck her again, and she crawled out from under the table, still blowing the server, and stuck her ass in the air. I put on another condom, pulled down her panties, and began working my cock into her ass. She was still lubed from our last fuck, so I was able to enter her quickly and begin fucking.
Watching her blow the server was such a turn-on that I blew my load again in a couple of minutes, just before the server came. The server zipped up over his still-hard cock and said he'd be back with our order, then went back to the kitchen. I pulled out of my date, pulled off the condom, and threw it under the table. My date turned her head to face me, and let me watch her lick the last of the server's cum from her chin. Then she stood up, pulled her panties back up, and admitted that her knees were sore from kneeling on the restaurant's tile floor.
When the server came back with our order, my date pulled his head down and kissed him, letting him taste his own cum. He asked her for her number, but she told him no. We ate our meal, left the bill and some cash on the table, and left.
On the walk back to the motel, my date said she had never had such a wild time in her life, and asked if I had ever been part of a threesome before. I told her I had once the night before my wedding with my wife and one of her bridesmaids. My date asked me if I was still married, and I said I was.
She wasn't happy to hear this. She hadn't realized that I was married, even though my profile says that I'm involved. She told me that she didn't see married men, and that our date was over. Then she walked back to her room, and I walked back to my car.
I've never seen her again.
We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.
Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or would prefer to wait in the room while she finished dressing. I told her I would like to wait in the room with her.
She had just finished showering and shaving, and was nude. She must have been feeling sexy, because she asked if I would like to fuck her as she was. I like my dates to be as femme as possible, so I told her I'd like to wait until she was dressed. She had several sexy outfits ready to put on, and she asked me which I would prefer. I chose one that showed her great legs and hot ass to good effect, and she began putting on makeup. I enjoyed watching her make herself up and get dressed, and I would occasionally run my hand over her shoulder or leg, or rub one of her nipples, which turned her on very much.
She put on a sexy black spandex dress with a black bra and panties, and a metallic red wig. When she was fully dressed, she smiled and asked if I thought she looked sexy. I smiled back and told her she did, and said that I couldn't wait to fuck her. I was already getting hard just looking at her, and when she knelt down and unzipped my pants, my cock jumped out. She ran her tongue over the head, and said that my precum tasted wonderful. I took her head in my hands and slid my cock into her mouth, and she went to work on it with her tongue while her hands rubbed the shaft and cupped my balls.
She gave me five minutes of a terrific blowjob, then said that she couldn't wait any more and wanted to feel my cock inside her. I put on a condom and told her to lie on the edge of the bed with her ass in the air. I pulled down her panties, put some lube on my middle finger, and worked it into her ass while she moaned and said how good it felt. With her panties down around her knees and the skirt of her dress pushed up to her waist, I began working my cock inside of her. In between gasps and moans, she told me how thick my cock was and how great it felt.
She told me it had been over a year since her last fuck, so I went slow at first, easing my cock in, then pulling out again when she asked. But over the next few minutes, I was able to bury it deeper and deeper into her ass, until I finally had it in balls-deep. I had my hands on her hips, and I fucked her faster and faster until I couldn't hold back any more and I came.
I continued to slowly fuck her until my cock went limp, and I pulled out, took off the condom, and threw it in the trash. She slumped down onto the bed, and she looked so good there with her skirt up and her panties down that I was sorry I couldn't fuck her again right away.
Instead, I laid down on the bed beside her and began running my hands over her ass, back, and shoulders. She turned her head to face me and said that my hands felt very nice, and asked if I would kiss her. I did, and for a while we held each other while I kissed her and massaged her shoulders.
She asked me if I had to go, and I told her that I didn't. I told her that she looked so hot and sexy that I wanted to show her off, and I asked her if she would like to go out to eat. She was shy at first, but eventually she agreed, and we both straightened ourselves out and left the room. She said there was a Denny's within walking distance, and asked if that would be all right, and I told her it would.
We had our arms around each other as we walked across the motel parking lot and down to the street. It was late at night, but from time to time a car would pass by, and when it did I would stop walking and take her in my arms and kiss her while my hands ran across her back and ass. She told me she had never been out while dressed, but being with me and having me kiss her in public made her feel like a sexy woman.
Inside the Denny's, there was a couple in their 20s eating at one table who looked up when we entered. The woman turned back after a moment, but the man stared at my date for a couple of seconds before looking away. I gave her another lingering kiss before leading her to a booth in the corner. My back was to the other couple, but my date could see them, and she told me that the man kept looking up at her.
A server came and got our order, and he also kept staring at my date. She smiled at him and licked her lips, and he had to tear himself away to look at me and ask for my order. By the time he left, I was getting hard again, and I asked my date if she was in the mood for something hot. She said she was, so I asked her to get down under the table and blow me again. She sat still for a moment, then smiled a wicked smile and slid down off her seat.
I spread my legs for her, and she quickly unzipped my pants and had my cock out. She started blowing me, and she was still at it when the server came back with our drinks. When he saw my date blowing me, he set our drinks down on the table, then unzipped his pants and pulled his own cock out. My date let my own cock go and went down on the server. I looked back to see what the other couple was doing, but they had finished and left. It was just the three of us.
I told my date that I wanted to fuck her again, and she crawled out from under the table, still blowing the server, and stuck her ass in the air. I put on another condom, pulled down her panties, and began working my cock into her ass. She was still lubed from our last fuck, so I was able to enter her quickly and begin fucking.
Watching her blow the server was such a turn-on that I blew my load again in a couple of minutes, just before the server came. The server zipped up over his still-hard cock and said he'd be back with our order, then went back to the kitchen. I pulled out of my date, pulled off the condom, and threw it under the table. My date turned her head to face me, and let me watch her lick the last of the server's cum from her chin. Then she stood up, pulled her panties back up, and admitted that her knees were sore from kneeling on the restaurant's tile floor.
When the server came back with our order, my date pulled his head down and kissed him, letting him taste his own cum. He asked her for her number, but she told him no. We ate our meal, left the bill and some cash on the table, and left.
On the walk back to the motel, my date said she had never had such a wild time in her life, and asked if I had ever been part of a threesome before. I told her I had once the night before my wedding with my wife and one of her bridesmaids. My date asked me if I was still married, and I said I was.
She wasn't happy to hear this. She hadn't realized that I was married, even though my profile says that I'm involved. She told me that she didn't see married men, and that our date was over. Then she walked back to her room, and I walked back to my car.
I've never seen her again.
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