My first time with a boy

This is a true story though not a picture of myself. Warning this story contains sexual content.  As i posted yesterday by 1996 and age 17 i had my first real crush on a boy. I had thought guys were cute before but never had a serious crush. I still didn't really know what all of it meant. I felt like a girl but knew i was geneticly male. So my mind wondered did this mean i was gay? I had no concept of bisexual at that time. About this time I also got the internet and discovered AOL chat rooms and message boards and their LGBT community Planet Out. I started visiting the Planet Out chat rooms for young gay men and trans women. Some people sent me my first gay porn and i liked what i saw and wanted to try being with a man. I had a girlfriend at the time and had had sex with her before but the idea of being with a man excited me. So after many days and some nights spent in various chat rooms i found a local guy who was close to my age and interested in meeting up with only the expectation we would see what happens and only do what i felt comfortable with.

The day came and Richard arrived at my door on a day when i was home alone with lots of time till my dad came home. I welcomed him at the door. I'll admit he was not the best looking guy in the world but i figured he is already here and i really want to see what happens. We talked for a few minutes he could tell i was nervous but he was really sweet and didn't rush anything. After talking for a while he moved closer to me and kissed me and i found myself kissing him back. Before you knew it we were making out. And it felt natural and right and so good. The only complaint was the stubble on his face was rough and a little painful.

After kissing for a while we made our way back to my room where we kissed some more then he asked if i wanted to go further. We had talked about trying oral sex and seeing if we wanted to go further from there. I was very willing to try at this point. So he lowered his pants and i did the same and we both removed our underwear. I could see he was already getting hard he had a fairly small uncut cock but even so i was excited and willing. We kissed some more and fondled eachothers cocks before he lay on the bed and i got on my knees and started teasing his cock with my mouth sliding his foreskin down with my hand i tentatively took his cock in my mouth running my tongue up and down his shaft. I didn't know how i would feel doing this for the first time but it felt right and good and we were both enjoying it. He eventually returned the favor and we finished eachother off with an hand job. I also tasted a little of his cum out of curiosity and i liked it. We just layed there and held each other for a while then one of us suggested me might want to try more.

I discovered Richard was a bottom and wanted me to top him. I quickly determined that was not for me but knew i'd be willing to try being a bottom but that would have to wait for another day.

When it was all over i was more confused than ever i loved the experience i wanted to try more but i also knew i was still attracted to women too and i knew i still felt like a woman myself. Richard and i continued talking and it was clear he wanted me to be his boyfriend. When i told him how i felt about wanting to be a woman he told me he wasn't interested in women that he was gay and wanted a man. That ended any talk of a relationship and just added to the confusion in my mind. If i'm a man who feels like a woman and wants to date men then who am i suppose to date afterall being born male wouldn't only gay men want to date me? I had no idea that sexuality and gender identity were really separate issues.  It would take some time and a few more experiences with men to come to a complete understanding of all of this.