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Night Time Adventures

Posted by: Age: 18-19 Posted on: 3 comments
4 likes 2 views Category: Masturbation Male-Male Tags: teen humping, swimwear humping, new friends, pool humping, speedo fetish, zesty

Fictional adventures after dark…


When I was 19, I lived in a peaceful, quiet, suburban neighborhood. The year before, at 18, I had seen a young man at the local pool wearing a pair of swim briefs. This was the first time I ever saw this type of swimsuit in public and I was amazed at how well they fit him - nice and snug on his body and I loved it when they got wet because the material was very shiny. I decided that I would have to get my own pair!

 

After university classes one day I walked to the closest mall and browsed a bunch of sport stores for swim briefs. I tried on a lot of pairs, but eventually settled for a plain red pair that fitted me perfectly. Over the next year I used my red briefs in my masturbation experiences. If I was home, I would hump my pillow with the briefs on or lie on my bed and just rub them until I came. If I was at the pool and there wasn't many people there, I would hang on to the edge of the pool and hump the wall of the pool underwater. I also loved going to the library and reading books on sex ed. I particularly loved 'It's Perfectly Normal', which had drawings of naked bodies. This book turned me on a lot and I would go to the library toilets, strip off all my clothes except my socks, shoes and swim briefs (which I loved wearing everywhere!), and rub into the briefs while looking at the mirror on the back of the toilet stall door.

 

Almost every day from the time I got the swim briefs, I would cum in them, wash them in the bathroom sink at home, dry them and repeat the next day. On an extremely hot summer's day, a few months after I turned 19, I was struggling to get to sleep. Even with the fan in my room and wearing just my red swim briefs, I couldn't force my body to get even a little bit tired. Just past midnight, I decided to get up off my bed and go downstairs for some water. I poured myself a glass of water in the kitchen and drank it quickly. On my way back upstairs I passed the garage, with my black bike being dimly illuminated by the moonlight. Suddenly I had an idea: what if I rode around my neighborhood on my bike in just my briefs! The very idea caused my 7 inch penis to pulsate. Minutes later, I was off! I circled the block multiple times and it felt both scary and exhilarating being almost naked and riding around on my bike. The continuous friction between my bike seat and my butt felt amazing - and my penis was now at full erection.

 

 

After circling my block for what felt like the thirtieth time, I decided to ride into another block. A few houses into my journey, I noticed a young man resting in his small blow-up pool. Upon closer inspection, I noticed he wasn't wearing anything but a pair of blue swimbriefs with white stripes all over. Another fellow swimwear lover! How exciting! I was quite shy back then, but on that night, something told me to go for it. I left my bike on the grass area at the front of the guy’s house and walked across the grass to the guy in his backyard. He didn't notice me until I was a few feet away from the pool he was in. When he noticed me, he kinda looked away, embarrassed. I guess he was shy as well. 'Hi,' I said to him, 'it's too hot to sleep so I'm just riding around the neighborhood to make myself tired'. The boy said hey back and eventually we got a quiet conversation going.

 

His name was Devin and he was 18 years old, had a mop of dark brown hair and was quite skinny. He told me he got interested in swim briefs after seeing one of his university classmates wear one for swimming, and had been wearing his blue swim briefs very often since he first bought them.

 

 

I noticed that his penis was beginning to grow under his briefs. Eventually it reached a full erection and I guessed he was 6 or 6 1/2 inches at the time. His briefs were very small and tight, with his erection barely being contained inside the material. Devin had left the drawstring on the outside of his briefs (he later told me it felt uncomfortable if the strings were inside with his boner). As we talked about our life, university and swimwear, both of us were beginning to get very horny. I asked Devin if he ever masturbated in his swim briefs. At first he didn't say anything, but then he told me that he loved to do it! One of his favorite methods was to do it in his blow-up pool. He would fill the pool so that the water was just covered his body when he lay down. He would rub his boner underwater, imagining his hand was actually his uni classmate and they were both wearing swim briefs and humping each other in the pool on their campus.

 

 

All this talking was making me even hornier than ever before. I immediately proposed that we would both masturbate each other by humping each other in the blow-up pool. I expected some hesitation from Devin, but he immediately said, 'OK,' and I was excited to start. Because I was heavier, I lay down on my back first and Devin dropped on top of me. Devin's hand held onto the edge of the blow-up pool while my hands roamed around his back and butt. It took a minute or two to get comfortable, but eventually we developed a good humping rhythm and humped away! I was amazed that half an hour earlier I was riding my bike around my neighborhood and now I was underneath a guy I just met who was humping my briefs furiously. With each hump, there was the soft squeak of the blow-up pool. After a few minutes I could vaguely see (it was quite dark) Devin closing his eyes and arching his back in ecstasy. He let out a few soft groans as I felt his penis meet with mine through our briefs and let out a few ropes of cum. Just as Devin was getting off me, I felt a similar sensation in my own crotch and shot after shot of cum flew out of my penis and contained itself in my red swim briefs.

 

 

After climaxing just seconds within each other, Devin and I slunk back into the pool and relaxed. We just stayed like this for what felt like ten minutes before Devin asked me, 'Do you want to go inside and do it again?'  I quickly nodded and followed Devin into his house and up the stairs to his bedroom. We were still a bit wet from the pool - drips of water had left our bodies and our swim briefs, falling to the floor as we headed upstairs. When we reached Devin's room and saw his bed, neither of us hesitated. We both got on the bed with our damp briefs and humped away, this time with me on top. This time, it only took two minutes to climax and we shot tiny amounts of cum into our swim briefs. At this point we were dead tired - Devin and I fell onto his soft, comfortable bed and drifted off to sleep.

 

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