Fucked My Childhood Best Friend

Teddy and I grew up the only kids in our area, so we were together all the time. He is same age as me, and we've known each other since we were 6 years old. Teddy was always small and neither of us were into sports or anything, but we hung around, played together, video games and hiking through the woods etc. At 12, I realized if I moved my hand on my cock I'd get sperm out. I even demoed for him and weirdly he scooped a lot of it up with his fingers and put it in his mouth and liked it evidently. We were at an indoor pool complex and were the only two there mid morning in the middle of the week. Teddy pulled his suit down and started doing it too, he couldn't get it and I even used my hand on him, he had a pretty small cock, even for that young age. He finished and again used his fingers and put it in his mouth. I wouldn't do it, though he offered some to me. That was as sexual as it got for us. In high school he never dated, never even looked at the hottest girls. His body didn't really develop much, he had a rather feminine body, in some cases better looking that some of the girls in class.

I dated, fucked, sucked and loved it, he'd listen to me talk about particular girls, and one girl in particular who was totally shaved or waxed, and another who had a wide landing strip about and inch and a half wide up to the top of her pubes. A couple weeks later I spent the night at his house and in changing I saw that he had shaped his pubes into the landing strip too, I didn't say anything and a month or more later, I saw he had shaved it all off.

I stayed here for college, he went away for school. A couple weeks ago, I saw a girl going in and out of his house. She said something to me, and I realized it was Teddy. She preferred Tiffany now, and she was transitioning to being a woman. It really didn't surprise me, he certainly had the body for it. His mom was gone for a few days, and SHE invited me over. I was respectful to use she, her etc. She finally over a drink asked if I had any questions about the process or about her. i did, and honestly knew each other so long I felt comfortable.

Did you still have a cock? YES, it's a bit smaller now though.

Did you have real tits or did you wear falsies? YES to both. She had about an A cup, smallish tits with pouting nipples and areolae, and depending on which dress she wore she did sometimes wear breast enhancements.

Have you had sex as a guy? NO

Have you had sex as a girl? YES, with two guys, one was a one night stand, she thinks he just wanted to cross one off his bucket list, and the other lasted over a year until his parents made him get a girlfriend, she got pregnant and got married.

She wanted to go swimming so I was going to go to my house and get a pair of swimming trunks, and she said she had some there. I went into her bedroom (redecorated for a woman) to change. When I was nude, she came in nude also and got out a bikini from her drawer. I could barely see her cock, she had it tucked between her legs, and had the landing strip again. She commented that we'd spent enough time together that we needn't be shy around one another. She turned her ass to me to get a bikini out of a drawer and I was hard as a rock. Her ass was perfect.

We went out, we swam, and back in her room all dried off, she was nude again. She asked me what I thought. I'd always liked women with smallish tits, and loved nice womanly hips and butt and great legs. She had it all, except a pussy. I told her all that and she pointed to my erection and told me she thought I must like what I see. Walking over, she kissed me and I kissed her back. She took me to her bed and sucked on me, and took me in her ass. It was my first time having anal sex, and I must say I really liked it.

So, it's happened four times since. I do have two girls I fuck, I've now gotten one of them to give up anal to me. But honestly Tiffany is the best fuck and suck I've ever experienced.
I fucked my childhood best friend