I guess the idea of having sex with a man began to intrigue me in my teens. I spend my teens in San Pedro, California. San Pedro is a seaport town and as such has a lot man oriented occupations.It was a small enough town that when I went out at night I'd walk everywhere. A lot of times one of these extremely masculine men would stop to ask directions. Almost always they would eventually ask me other questions. Usually ask if i needed a ride. I always said no. They would then ask if I worked out, because I looked like I did. I told them no I didn't work out. Almost every time they would hand me some sort of business card and tell me to call them sometime. It was like they all had the same routine. When I told one of my older buddies about these encounters, he laughed and told me they were probably trying to pick me up for sex. I couldn't believe it. I was naive and wasn't the least bit familiar with this kind of thing.
I began reliving some of these encounters in my head and I found myself getting curious about a possible hook up with one of these guys. I would fantasize every kind of scenario. Sometimes I would imagine getting in the car with one of them. He would then drive us to a very dark side street. Once parked he would simply pull his cock out and gently push my head down to suck him off. Another would be to have him take me back to his apartment and we would both undress and feel each others body and he would tell me how nice I felt and then push me to my knees to suck his cock.
But the fantasy that made me the hardest and horniest was the one where one of the men became a regular sex partner and would have me stay with him for a weekend or longer and make me perform sexual acts with him. Eventually making me wear women's clothes for him whenever I spent the weekend. I fantasized about him making me wear everything from high heels and nylons. Nightgowns and teddies. But one of my favorites was him making me wear heels and a sundress with nothing on underneath. He would make stand on his balcony and watch me. The sun would shine through the dress and he could easily see my little cock and young ass through the dress. This with the thought that anybody outside could see me was a tremendous turn on. I think it all boiled down to me enjoying be submissive to such a masculine man.
I found myself walking through town a lot hoping somebody would ask me for directions. I t happened quite a few more times, but I never had the courage to hook up. I did however start to lean in the car windows and check out their crotches. They knew of course and would really try to convince me to go with them. I didn't mind talking to them about the possibility of getting together for sex sometime, but I never had the courage to actually do it.
I eventually got married very young and stayed married for about three years. Even though I very much enjoyed sex with my wife, I never got those fantasies of other men out of my head. After I left my wife, I moved to a gay section of Long Beach, California. I didn't think I actually wanted to gay, but I knew for sure I wanted to try gay sex.
Not being familiar with the gay life style and unsure of myself I did not approach men for fair of being wrong about him. So I just put myself in positions where other man could hit on me. It worked and it worked well. I was young enough that I was still attractive to other men. I also liked it because If he was picking me up,in my mind he was by default the aggressive one and I was the submissive one.
For a period of 4 or 5 years I had a lot of sex with a lot of men. I really learned to enjoy it. It felt natural to me. I was even able to live out my fantasy of dressing as a woman for a tall gorgeous black man. His name was James and we had a 1 1/2 year relationship. He liked me being submissive to him and an occasional buddy of his. Yes he shared me once in a while. He always had me wear women's things not just for him, but for his buddies to. I really loved "belonging" to James.
One night he called me and told me to come over to his place for a little romp. He instructed me to wear my "lady things" under my clothes. I happily complied. When I entered his apartment there were four other black guys sitting at the table playing poker. I looked at James with that what the fuck look. He quickly came to me and led me into the bedroom. He told me he had promised his buddies a poker game they wouldn't forget. Because of my fetish for women's clothes James always kept a few dresses in his closet for me. He asked if I had worn my panties and nylons like instructed. Yes, I said. James then instructed me to put on one of the dresses and to wear heels. I was to come out to the table dressed as a woman and provide whatever his friends wanted. Everything from drinks to blowjobs.
I walked out from the bedroom and every guy at the table turned to look. One of them blurt out "damn, she's got pretty legs". I had actually put lipstick on so another guy commented about my nice mouth. Another guy was rubbing his crotch and I could see how big he was even through his jeans.
I walked over to James leaned down and kissed him on the cheek and said "Baby, can I get you anything"? He looked up and said "no, just find out what the boys want".
"Gentleman, can I get you anything?" I asked. With that, the guy that had rubbing his crotch pulled his huge cock out and said "I think you know what I need". He slid his chair back from the table, I got on my knees and slid his magnificent cock in my mouth. He was huge , but because of my time with James, who was also huge, I had no problem taking him all the way down my throat to his balls. He let out a gasp and then told James no wonder you keep this bitch around. I would to.
That's how the evening started and finished. I sucked the cum out of each and every one of them. After they all left James took me to bed and had his way with me. He thanked me for taking care of his buddies, but I told him I should be thanking him.
James and I eventually went our separate ways. I kept having gay sex for a couple of more years, but I never found anyone that let me enjoy it as much as James did.
Eventually I went back to dating women, but I still like the idea of sex with men. I love sex with women, but with the right guy I can really feel submissive.