Straight Male / 34
Married 34, male, middle America. This happened when I was 16.
A guy I knew, and had gym class with was fat, kinda girlish in his face, and actually had boobs. At 16 he'd not developed any hair on his cock yet, his cock was only about 2 inches long and not very thick. He had light pink areolae and nipples. He said it was a gland condition but he had tits. That also didn't explain why I caught him putting on lipstick and eye shadow and pulling his longish hair back into a ponytail. No one was home at his house and his parents weren't returning until the next day.
I made him strip while in his make up, he protested the whole time but I wouldn't be denied. I had him sit on the couch in the living room totally naked and I laid down with my head at his tits. I started sucking his tits and he was begging me to stop that he didn't like it and didn't want it. I sucked his tits for almost 30 minutes, my hand reaching around to his big, fat ass. I moved his hand to my cock and made him tease my cock with it. I'd never had sex before and I knew this was my chance. I'd prefer it with a girl, but as I had seen some anal sex porn I knew I had a hole with him.
I got up, went to the bathroom and found some Vaseline, that I rubbed all over my 7 inches. I'm pretty thick just about 2" and once lubed totally I took a glob of Vaseline and put it on my finger and walked back out. I told him to roll over and he started to cry but, he was rolling over. I spread the Vaseline into his asshole to more vocal whimpers and got on top of him, lined up to his, now my, fuckhole and thrust in with one move. I pushed it all the way in and held it there, he was squirming and crying, and begging me to pull out. Then as he calmed down I felt a squeezing on my cock as he was getting used to the thick meat spearing him. He was still begging me to pull out and I told him that with tits that pretty he should be fucked like a girl, and I proceeded to pump his poopchute. I came in about 5 to 10 minutes and he whispered that he could feel it as I was spurting inside him. I pulled out with a plop, and got a little fart in return. I told him to get up and get a washcloth and towel to clean me up, then himself.
After he wanted to get dressed and I wouldn't let him. Instead I started playing with his tits again and made him play with my cock. I got hard again, and I fucked him again, still crying that time also. I played with his little excuse for a cock and did see some beginnings of hair above it. I spent the night fucked him again, any free time I spent sucking on his tits. We slept in the same bed and the next morning I got morning wood and fucked him again, this time missionary with me sucking and pinching on his cute tits and nipples the whole time. We got dressed and went to McDonalds for breakfast and when we came back he immediately got undressed again.
I fucked him 6 times before I made him, crying again, suck my cock to completion. For the next two years he was my gay girlfriend. He is still gay, still has tits though has slimmed down a lot. I fucked him for that time then finally got a girlfriend who would suck me, fuck me and let me fuck her asshole too. In college I met my wife, she's a total slut and whore and we've had a great sex life. Only one time, after he had slimmed down, I went back and fucked my first piece of ass again. I don't know why, he/she was totally living as a woman, had a boyfriend, and let me fuck her anyway.
A guy I knew, and had gym class with was fat, kinda girlish in his face, and actually had boobs. At 16 he'd not developed any hair on his cock yet, his cock was only about 2 inches long and not very thick. He had light pink areolae and nipples. He said it was a gland condition but he had tits. That also didn't explain why I caught him putting on lipstick and eye shadow and pulling his longish hair back into a ponytail. No one was home at his house and his parents weren't returning until the next day.
I made him strip while in his make up, he protested the whole time but I wouldn't be denied. I had him sit on the couch in the living room totally naked and I laid down with my head at his tits. I started sucking his tits and he was begging me to stop that he didn't like it and didn't want it. I sucked his tits for almost 30 minutes, my hand reaching around to his big, fat ass. I moved his hand to my cock and made him tease my cock with it. I'd never had sex before and I knew this was my chance. I'd prefer it with a girl, but as I had seen some anal sex porn I knew I had a hole with him.
I got up, went to the bathroom and found some Vaseline, that I rubbed all over my 7 inches. I'm pretty thick just about 2" and once lubed totally I took a glob of Vaseline and put it on my finger and walked back out. I told him to roll over and he started to cry but, he was rolling over. I spread the Vaseline into his asshole to more vocal whimpers and got on top of him, lined up to his, now my, fuckhole and thrust in with one move. I pushed it all the way in and held it there, he was squirming and crying, and begging me to pull out. Then as he calmed down I felt a squeezing on my cock as he was getting used to the thick meat spearing him. He was still begging me to pull out and I told him that with tits that pretty he should be fucked like a girl, and I proceeded to pump his poopchute. I came in about 5 to 10 minutes and he whispered that he could feel it as I was spurting inside him. I pulled out with a plop, and got a little fart in return. I told him to get up and get a washcloth and towel to clean me up, then himself.
After he wanted to get dressed and I wouldn't let him. Instead I started playing with his tits again and made him play with my cock. I got hard again, and I fucked him again, still crying that time also. I played with his little excuse for a cock and did see some beginnings of hair above it. I spent the night fucked him again, any free time I spent sucking on his tits. We slept in the same bed and the next morning I got morning wood and fucked him again, this time missionary with me sucking and pinching on his cute tits and nipples the whole time. We got dressed and went to McDonalds for breakfast and when we came back he immediately got undressed again.
I fucked him 6 times before I made him, crying again, suck my cock to completion. For the next two years he was my gay girlfriend. He is still gay, still has tits though has slimmed down a lot. I fucked him for that time then finally got a girlfriend who would suck me, fuck me and let me fuck her asshole too. In college I met my wife, she's a total slut and whore and we've had a great sex life. Only one time, after he had slimmed down, I went back and fucked my first piece of ass again. I don't know why, he/she was totally living as a woman, had a boyfriend, and let me fuck her anyway.
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