Where it happened: woods
My first time was with another guy, my younger cousin. We started talking about sex one day, with him asking a lot of questions. That day endeded with me showing him how to masturbate.
The next weekend he told me he couldn’t orgasm by himself, and wanted me to “do” him. I resisted at first, but then took his skinny penis in my hand and stroked him to his firt orgasm.
Later that summer, he talked me into letting him suck me. It was heaven, better than I expected, and soon I sucked him. But we had one more step to go…
One weekend he was staying with us, and we decided to have anal sex that night in my bed. We both made trips to the bathroom to lather up, but only slid around without penetration. (It felt great, though.)
But the next day, we trudged deep into the woods to try again. We forgot to bring a lubricant, and had to use my salive. But…there standing in the pines with our jeans down around our ankles, I finally managed to squeeze into his ass. As I stroked, the going slowly became easier as he losened up. With my hands on his waist, pulling him tight against me, I shot my first gay load of sperm into his almost virgin ass.
We made this a weekend ritual for the next several years, except that after a few months I realized that I preferred to be the “girl.” And we got kinky too.
My favorit recollection is of the afternoon we were all alone in his home, and I dressed up in his sister’s clothing. I looked silly, I guess, with a wig, a (sock stuffed) bra, a silk teddy, pantyhose, and nylon panties on. It go even kinkier when we decided to act out as closely as possible what m/f sex would be like. This meant, of course, that we had to simulate using birth control. And the only thing available was him mom’s Ortho foam.
I stood there in my pantyhosed feet, and filled his mom’s plastic applicator with the creamy foam. Then I trembled with excitement as I lay face down on her bed, as her son took off his pants.
Soon I felt him pulling down my panties and hose. Then he parted my ass cheeks and twisted the (vaseline coated) applicator deep into my ass. I felt the cool foam slide inside me, then the applicator was removed.
Moments later I felt his weight on my back as his skinny cock slid around in search of its target. It only took a minute for it to find home, and he began to pump it slowly in and out.
I soon turned onto my back, and slid to the foot of the bed, to allow deeper penetration, to watch his face, and to be able to stroke my own dick.
We both came that way, with me bringing myself to climax the moment I felt his skinny cock spurting its sweet little load in my ass.
We continues to enjoy ourselves until I was 20.