My First Time with Another Guy

Literotic asexstories – My First Time with Another Guy by bmcmann,bmcmann
I was 18 and hanging out at a friend’s house over night. He had a girlfriend. I had been seeing a few girls too. We spent the day on our bikes and playing basketball. Later in the evening we were playing Nintendo on the living room floor until his parents went to bed. Then things got a little more interesting.

He said he wanted to show me something. He turned the TV to Cinemax. His parents were religious so they didn’t subscribe to anything like that but their screen actually showed a lot more than I had seen on TV before. There was a movie finishing up with a younger girl who slept with her father’s friend. Then the next video was two women kissing and touching each other. I was hard as a rock after a few minutes, and from the way he was shifting around the floor I could tell he was turned on too.

I asked him what he thought it was like for them being with a member of the same sex. He said he didn’t know, but I could see the wheels turning in his head. He suggested we give each other turns with the TV so we could get some relief. It was pitch black in the house except in the front of the living room where the TV was. My stomach felt funny as I realized how hot the idea of him touching himself seemed to me.

He sent me away first into the next room separated by an archway. I didn’t really like the feeling. It was dark in there, and I was in a house I wasn’t familiar with. I decided to look over toward where he was in front of the TV. It was about 20 feet away so I couldn’t see much but I did see movement and could tell his shorts were down around his ankles. I started grabbing at my own cock and had that funny feeling in my stomach again. It was just too weird. I was getting turned on watching another guy half naked and masturbating.

I whispered in to him to get his attention and asked him if we could switch or something. He pulled up his shorts, and I went back into the living room. Our shorts weren’t really hiding much at this point.

I offered to let him stay and said we could just promise not to watch the other or maybe just keep our shorts on. So he sat down a few feet away and reached into his shorts. I followed his lead and worked on myself inside my shorts.

After a few minutes he repeated the question I had asked earlier about how they could be so into a member of the same sex. When I just said ‘hmm’ and shrugged, he said something about it might not be so weird if someone was wearing women’s underwear and maybe touching through that.

I moved closer to him and ended up sitting behind him, both of us fully clothed on the floor with my legs on the outside of his. He pressed up closer to me so that his back and butt were right up against my cock while we continued to watch the screen. He kept pressing into me so I started to get more turned on and braver. I put my arms around him and pulled him closer. With the pressure and friction from his body against mine, I wanted more. I slid my hand down outside of his shorts but started massaging his cock a little bit. His was thick like mine, and it added enough familiarity to the situation where I wasn’t as nervous about it.

I stopped and attempted to reach down into his shorts when he abruptly got up and said he would be right back. It looked like he was going down to the basement. I moved over to the couch and caught my breath for a few minutes. I had taken off my shirt, pulled my shorts down a little and pulled a blanket up to cover myself.

When he came back in, he still had his clothes on but then started to strip down on the floor in front of the couch where I was laying. When his shirt came off I saw he had his mother’s bra on. Next his shorts came off and he was wearing her panties too. He laid down flat on the floor alongside the couch so we were head to toe.

I reached down and started rubbing his cock through his mother’s panties. It was very different this time! I could feel the head and the full shape of it. I didn’t give him any warning before sliding the panties down his cock so I could touch it directly. It didn’t take long with me handling him before he sat up and climbed onto the couch on top of me.

The panties slid back up, he got underneath the blanket, and I was caught. My shorts were just above my knees so I couldn’t move, and we were both twisted in the blanket. I felt him dry humping my cock so that only the panties separated his from mine. His head was caught under the blanket, and I had one free arm. We were cock to cock with a thin silky material between us. He was furiously dry humping me and kissing my chest while my free hand caressed his head on top of the blanket.

There was no turning back for either of us now. I told him to move back to the floor and lay down. I joined him on the floor and took off the panties. I was between his legs with my head a few inches from his cock. I had one hand gently massaging his balls and the other going up and down on his cock. The head of his cock was so smooth, and I had never experienced a scent like this. I breathed it in deeply and my stomach had that funny feeling again. I stopped what I was doing and licked from just above his balls to the tip of his cock. I asked him what that felt like, and he asked what I had done. I told him but I think it freaked him out a little bit. My hands went back to work and within a few minutes he was cumming a lot. There was some on my hands, and I breathed in the scent again but I didn’t try tasting it.

He recovered and pushed me back so I was laying down. With one hand he was aggressively pumping my cock. I wasn’t used to doing anything that fast or hard so after a few minutes of that I took over and got myself off, and it was so much more cum than usual.

A few months passed before we saw each other again. My parents had left in the middle of the day, and I invited him over. We talked a little bit about what had happened during the sleepover and just bringing it up was a turn on. He had jeans on so I let him borrow a pair of my athletic shorts. It was sunny out so I tried to find a closet for us but nothing really worked. We finally went back to my room and he suggested that we help each other through the blankets.

Him being in an identical pair of shorts to mine made it surreal when I felt his cock on the outside of the shorts he borrowed. He had me lay down. He got under the blanket and I pulled my shorts down a little. His head created a tent but I held the blanket down by my chest so I couldn’t see anything he was doing under there. Again he was aggressive and pumping really hard. It felt good at first but I had trouble relaxing enough to cum for him. I reached in, and he stayed where he was, his head keeping the blanket out of the line of fire. Within a few minutes I was cumming.

We traded places, and he was still hard. I got under the blanket with the heat and that smell again. Even though I had just cum I needed more. I pulled down his (my) shorts and started kissing around his cock and then eventually kissed his cock and rubbed it against my lips. After that I started trying to mimic what he did to me. I pumped fast and hard with my hand, and he was cumming less than a minute later. I lingered there while he caught his breath and started masturbating again with my hand inside my shorts.

After I had cum again we cleaned ourselves up. Reality hit that my parents could have come home at any moment. They eventually did, and after a few hours he took off.

I think I saw him once more before I went to college but we lost touch. I did see him a few years ago. There were a lot of people around, and we both had our home lives so even if I had been brave enough to bring it up I don’t think it would have happened again.

Those memories left me curious of all the things I was too scared to try then, and as much as I fight it as a married straight man, I sometimes think about other guys.