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First Time With Anther Guy

Posted by: Age: 14 then Posted on: 9 comments
16 likes 11782 views Category: Masturbation Male-Male Tags: friends, naked, pool, masturbating, gaurdina
The first time I masturbated with someone else was with a friend

When I was about 14 or so I was going over to a friends house to swim in his new pool. His dad was in sales and had to travel around a lot, and he had said before that if his bonus is nice enough he was going to have a pool put in for them. Well, it was and the summer before we started high school they had a brand new pool in their backyard. He only lived about 2 miles away from me, so I rode my bike to his house wearing nothing but my swimming trunks and sandals with a towel over my shoulder. By the time I had gotten there he had already been in for a while, and we stayed in for a couple hours before we started getting worn out and wanted to go back inside. We dried off a little and when we walked in he stopped on the large rug and said "just so you know, you're going to have to take your trunks off." I asked him why and he said his mom doesn't want us walking around the house getting water everywhere. I figured he was joking but he wasn't, then slipped his trunks down leaving him completely naked in front of me. "Why wouldn't you just put on dry clothes?" Well, the first time he walked in dripping wet his mom made him take them off right then and there. She said she would let him walk around naked before letting him lay on the furniture with wet clothes, and being the pervert that he was, he stayed naked for the rest of the afternoon. She didn't expect him to do it, but if he didn't mind her seeing him naked she really didn't have a problem with it either. So anyway, I pushed mine down to my feet and stepped out of them and followed him to the couch, both of us completely bare. Almost immediately my penis was hard, and after a couple minutes his was too, and then soft, hard and soft again. We weren't sitting there for too long when his mom came downstairs to get a glass of water and she saw us both sitting there naked. I was expecting her to get mad, but all she did was ask what I thought of the pool. I said it was great, trying to keep my growing erection hidden between my legs. She said she was glad and walked off. He just said "see? I told you!" We sat there for a little while longer watching TV before he got up to get a soda, and when he was up his mom came back down to start dinner. When she walked in the kitchen she saw his penis sticking straight up and she said "no no, you know how I feel about that. If you want to walk around naked, fine, but you aren't going to walk around my house with that. Take it up to your room, right now." He just shrugged and said OK, but by the time I got up to follow him I was hard too, and had to walk past her with my own cock stiff and sticking straight out. She just chucked and said "you boys are something else..." When I got upstairs he was laying on his bed, penis still sticking up and twitching. I sat down at the foot of the bed and he asked what I wanted to do, and I said I wasn't sure. We sat there for a few seconds and then he asked "want to watch some porn?" "You have some?" "Oh yeah!" He got on the floor on his knees and reached under his bed and grabbed an unmarked tape and put it in. It was already halfway through a scene and a woman with huge tits was bouncing on the biggest cock I had ever seen in my life. He then sat next to me and leaned back on his elbows, dick still hard as a nail. About a minute later he grabbed onto it and started stroking slowly and asked "you gonna masturbate too?" "Yeah, should I close the door?" "Nah, my mom doesn't care." "Do you think she knows we're doing it now?" "Probably, we were both naked and hard, she's not stupid." Just thinking that she knew we were both jacking off up here got me horny as hell and I started stroking hard and fast. I asked him where I should cum and he said just shoot on my chest, but don't get it on the carpet or she would get mad. I leaned back a little and shot a thick load all over my chest, and he wasn't far behind me. He laid back and when he came his legs stuck out and his toes spread apart and wiggled. He caught his breath and said "holy shit that felt good..." We then both went to the bathroom and wiped all the cum off of ourselves and went back, the tape still playing. By that point we could both go again and he said "wanna race to see who cums first?" I said sure and when we were both completely hard again we started stroking as fast as we could. He won that time, with me shooting my second load about a minute later. Out of breath, we both just laid there for a little while talking, mostly about jacking off. This went on for about 20 minutes and I could feel myself getting hard again. I didn't even wait for him, I just grabbed my cock and started stroking. He glanced over and said "shit dude, you jerking again?" I just grunted out a soft "yeah.." This one was taking longer than the first, and before I could cum his mom yelled up that dinner was ready. He said we would be down in a minute and that set me off. This load wasn't as big, but it dribbled a little on my hand. We both went and wiped off and when we got downstairs my penis was still feeling a little full and was beet red. She saw us and said "you boys feel better now?" He then said "yeah, he did it three times!" I could feel my face getting hot and she looked surprised and said "well, you must be hungry then!" She could tell I was pretty embarrassed, and she said "oh don't worry, I know boys your age masturbate a lot." We then ate dinner and they acted like nothing had happened. The evening went on and I figured I needed to go home, but before I did we went ahead and jerked off one more time, this time with his mom right down the hallway. After my fourth cum I couldn't go on anymore and had to call it a night. After that day though, I masturbated a whole lot more at his house.

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