First time dressed as a woman - Sex Stories

First time dressed as a woman

Ok, this is an absolutely true story. I'm a married white guy, stocky, 6'1" with a 5-1/2" cut dick. I've been dressing up on and off since I was a p*****n, starting with my mother's lingerie and dresses. I love makeup, but especially lipstick. I used to masturbate by stroking my cock with a bl**d red lipstick while reading those old trashy porn novels you could pick up in the seedier luncheonettes. I always denied my cock loving side, imagining myself as a lesbian for the most part, but I fantasized a lot about sucking cock and getting fucked. Once I'd cum I'd feel ashamed and try to put it out of my mind. I never had a same sex experience until about 2004 when I had been frequenting a local gay forum where the person who had started the forum was only about 20 miles from me and offered first-timer's a crack at his dick. I traveled to his house and after some hesitation dropped down to take his dick into my mouth. It was not as I had imagined it would be. It was surprisingly spongy, where I had imagined it would be much harder. I didn't end up doing much. I went up and down for a little while and eventually just left. But I had finally done it. I had sucked a cock! And it was OK. Now let's move ahead a few years. I was getting more and more turned on by CD's, TS's and TV's and frequenting the cross-dressing forums and chat rooms. I began building up a collection of lingerie and lipstick, plus a few dildos and some DVD's. Gotta love the internet and anonymous shipping! Got ...

... some really sexy red fuck me pumps too which I loved to wear with my seamed black stockings. It was about this time that I got up the nerve to respond to a Craig's list ad. It was an older gentleman who said he liked to cross dress too and so I made a date to meet him at his apartment. This time only about 10 miles from me. I put on my thigh high stockings, some sexy panties, my red Frederick's of Hollywood corset, a red satin chemise over the top of that, stuffed by high heels into a backpack and put on my street clothes over the top of everything. I was shaking I was so nervous! I got to his apartment and he excused himself to put on something comfortable. I took the opportunity to strip down to my girl stuff and put on the shoes. He came out wearing just a negligee and sat down next to me on the couch. He leaned over and took my cock into his mouth. God it felt good! After a few sucks he suggested we get on the floor and we got into a 69 position. I gobbled up his cock feeling like such a slut in my outfit and he came quickly in my mouth. He moaned with my cock in his mouth and I was just so turned on that I came too. He swallowed my cum but I didn't swallow his, instead letting his cum dribble onto the carpet. I really wasn't ready for that yet, not with someone I'd just met at least. After we talked for a few minutes (it was obvious our date was over) and he said next time maybe we would fuck. Well, I never did see him again, but eventually I did get fucked by another guy ...