Thursday, December 8, 2016

First Crossdresser Experience

I remember the first time I fucked a crossdresser. I never even had any inclination or thought of fucking a cd. I was at the supermarket and saw a woman dressed in a very sexy outfit, wearing pantyhose and high heels, big hair, etc. She looked hot. She bent over and that's when I just had to go up and talk to her. I typically have no trouble talking to women, so I walked up to her to get her number. She looked at me and said that she wouldn't be a good match. I asked her why, and she told me that she was a crossdresser. I couldn't believe it. Anyway, we talked for a while and then the next thing I know I went to her place.

We chatted, but I couldn't help but to keep staring at her legs and ass. I was getting turned on, and I couldn't believe it. She was so fuckable. That's when it really hit me that she has a cock just like me. After a few drinks, I asked her if she has sex with men while dressed. She said that she did, but not that often. It dawned on me right then that if she's got a cock, then she doesn't have a pussy, and if she doesn't have a pussy, there's only two places by which I could fuck her: her mouth or her ass. I instantly got rock hard - I mean throbbing to the point of serious pain.

She got up and spilled some of the juice she was having, and it spilled right on my crotch. She knelt down on her knees with a towel and started to rub my crotch. It was clear that I was already rock hard. She stopped, surprised, and looked up at me. The next thing you know, I'm standing with my throbbing cock sticking out of the zipper hole of my slacks, and she's on her knees sucking and swallowing it. Her lips were stretched around the shaft of my cock it felt incredible just pumping her throat. I couldn't take it anymore, so I stood her up. I saw that there was a bulge under her dress. I hiked it up, and her cock was hard under her pantyhose, stretching it like it was just aching to rip through. Right then an overwhelming desire to penetrate the only other hole she has overcame me. I pushed her against the couch, and lifted her legs up over my shoulders. I pulled her panties and pantyhose down a little over her ass, just enough to reveal her tight fuckhole. I pressed the head of my cock against it, and it was wet and slick. She was breathing heavy, saying "I'm really tight". That just did me in. I couldn't take it. I slide it in, and as I did, her mouth opened and she moaned. I couldn't believe how fucking tight it was. Her asshole was just strangling and hugging my shaft in the best fucking way. I could smell her pussy, and I was just pumping steadily in and out of her tight asshole. She came first, all over her pantyhose, and her cum dripped down her cock and ballsack, down her crotch and right to her asshole as I was just impaling her with my throbbing shaft. Her cum lubricated her tight hole even more, and I just couldn't take it anymore. I came in her, filling her incredibly tight rectum with so much cum that it started to squirt out with the last few inward pumps of my cock.


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