[MM] My gf set me up with another guy

I’m 21 now but this happened back in hs. I had been dating thus girl for a while. She was a tear older than me and a lot more sexually open. She was totally open about things and would encourage me to hook up with other girls, she even set me up with a few friends of hers. It’s not like a porn fantasy or anything, just to be clear, they were usually not my type physically but I think that was part of the excitement for her.

One time we were hanging out with a gay friend and he said how hard it was to date in hs bc so many guys were in the closet. He was convinced he would go to college a virgin. And outta nowhere my gf blurts out “(my bf) will fuck you!” I was like, what?! I’d never done a guy and wasn’t interested really. I looked at her and she had a huge smile and was like “it’s not that different than a girl”. I looked at him and he had a confused look on his face but finally said “I mean, he is cute” and then rubbed my bicep.

I was pretty weirded out but she was really into it and it was clear ge was too. He said it would be a huge favor and all this stuff. She kept saying how hot it would be. Finally I was like, I can try I guess. I wasn’t sure I’d even get erect so it wasn’t a huge risk.

He and I went to the guest bedroom in the basement and there was this awkward moment of just standing there. Then he came over and kissed me and at first I pulled back. He had this hurt look on his face and asked if he did something wrong. I felt shitty. I said no, just give me a min. And then I went over to him and kissed him. It was weird to kiss a guy, but also felt a lot like a girl. I kind of lost myself in the moment.

He put his hands down my pants and gripped my cock. I was rock hard, to my surprise. He whispered “oh my god” and started to squeeze gently. I let out a little moan and after a while took my pants off. He got on his knees and stared at my dick a minute before putting his lips around it. In my head I was thinking that I was getting head from a guy and how strange that was. But it felt so good physically.

He sucked for a while but then got up and took his clothes off. I pulled off my shirt and he took my head and led me to the bed. We made out for a while and it was honestly super hot. His body was more muscular than a woman’s but he was still small framed like a woman. Eventually he asked if I would fuck him. I nodded. We struggled at first. I couldn’t get it it. He actually had to run up to the kitchen to get canola oil for lube. When he ran out, my gf looked in at me and saw me laying buck naked and erect on the bed. She smiled and said go get him tiger. I felt so self conscious but excited and ashamed. When he came back in he lubed his asshole and my dick and slowly sat down on it. He was clearly in some pain but he got it in. I tried to move and he said no stop he needed a minute. He leaned down slowly and kissed me. I put my hands on his ass cheeks and slowly rocked him back and forth. We picked up the tempo and soon were very slowly making love. After a minute he seized and his cock started spurting out cum. He said oh my god oh my god and my chest was covered in his semen.

I hadn’t cum yet and we kept going. Eventually I felt myself getting close and he said I could cum inside him. I let it go and he had the most surprised look on his face. He climbed off and we just lay there panting and sweaty. After a while he noticed I was still hard and asked if I wanted to again. I figured sure why not. He got on all fours and we did it doggy style and then missionary. We fucked for hours. My gf texted after a while to say it sounded like I was having fun but she was going home.

That was my first time with a guy. In college, I experimented more. Mostly with guys if I couldn’t find a girl. I don’t consider myself bi, but heteroflexible is more accurate. Hope you enjoyed!

Source: reddit.com/r/gonewildstories/comments/j9sgv6/mm_my_gf_set_me_up_with_another_guy