My First Encounter with a Crossdresser

Last Thursday I had my first encounter with a crossdresser at our Men’s Club get together. It was such a positive, profound experience I wanted to share it with my friend, Jim, who hosts the meetings. I sent this account to him in an email this evening:

What did you think of that cross-dresser, Cindy (Dan)? I just thought she was a late arrival Thursday so I thought I would play with her so she wouldn’t go home empty handed. When she took off her pants, she had on stockings, panties and a garter belt. Under her shirt, she had on lingerie. Then she opened her bag and took out some fake boobs, a wig and lipstick. At this point, my eyes were bugging out and I really wanted to see how this plays out. The other late guy didn’t know what to think. I offered Cindy my dick to suck and got the other guy involved so Cindy was sucking us both. Cindy seemed to turn her attention to me and before long, the other guy left. I hope it didn’t scare him off.

Then it got interesting. Cindy said she was a bottom and didn’t want me to suck her but she didn’t mind me fondling her cock. She had a nice hard-on and I really wanted to suck her but I respected her wishes. Well, with Cindy being a bottom, I offered to rim her and fuck her ass. She immediately knelt, bent over on the couch. I pulled her panties down in the back and stuck my tongue in her crack. I thought she would be clean shaven but she had a little hair in her crack and around her asshole. I kind of liked that. I started tonguing her rather enthusiastically to lube her up. Then I inserted a finger and found her to be very tight. She was really enjoying it so I managed to work two fingers deep in her ass to try and loosen her up. When it came time to penetrate her with my dick, she gave me a condom. I put it on and my dick was pretty hard but not hard enough to penetrate her tight ass. I squeezed and pushed but no luck so I went back to rimming and fingering her as deep as I could. Then, I asked if she wanted me to cum in her mouth and she was thrilled with that idea. I laid back on the edge of the couch and pulled my legs up. I asked her to finger my ass while she sucked me. In went her fingers and she started a slow, long suck. She gradually increased the pace and it was feeling real good! That is when you walked in. I wish you would have stayed and joined us. Perhaps we could do a threesome with her some time. Back to the sucking. She got me really close to cumming but the motion wasn’t quite right so I started stroking myself while she waited for me to cum. It didn’t take me long while she continued to finger my ass. I said, “Here it comes!” and she sucked my dick back in her mouth. My orgasm started slowly, then really started to build. The cum started flowing heavily but still no contractions. Then I really exploded, filling her mouth. You should have heard her moan with a mouthful of my cum! I thought she would swallow and be done but she kept sucking gently getting everything she could from my prostate. What made the afterglow so good was she still had two fingers in my ass. When I caught my breath, Cindy went over to the bed, lay on her back and masturbated. I offered to suck her off but he just wanted to make herself cum. I never really lost my hard-on watching her. She didn’t cum a lot but she looked like it felt real good. After we got dressed, I gave her my email address and she emailed me later saying how she enjoyed it. I replied the same and we may get together again.