[Bare Sqwhirl] Unintentional First pt1

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After a few months of being able to fulfilling my needs by finding guys on 900 lines, my folks finally caught on with a phone bill that was a $100 more than it normal. Luckily the company doesn't have a logo like your son is fag, it was just some corporate number. I guess they figured it was one of those ones with girls that you used to see advertised late at night. Being pretty embarrassed by the whole situation I was beginning to doubt the whole gay thing. I mean is this what I'm doomed for nights of finding random hook ups in 900 chat-rooms.*

I took a break for the rest of my senior year with the exception of a few hot JO sessions with Mark. But even those tailed off when he got a girlfriend and lost interest since he had a twat to bang.

But now I had graduated had the summer ahead of me before starting college in the fall. Being 18yo and horny as fuck I could only JO by myself so many times. I needed another warm body to so my seeds with. Then a weird thing happened one day when I was riding my bike. I used to ride my bike about 70 miles a week when I was a teen. Even though I was on the track team and played soccer I hated running to stay fit, I would much rather jump on the bike and hit the road. I think it may have been the Lycra shorts, I could wear those and which are hot and no one would think it was strange. On one of these days I decide to go to a local forest preserve and refill my water bottle. They have a nice spring and there are some old roads with long stretches and you never see many people beside other riders.

I drive to the park, get my bike out and ride the short distance from where I was parked to the spring.When I get there is another guy filling his bottles also he's a nice looking guy and was probably in his early 30's. I wait my turn and say hi as he turns and walks away. There were some other folks around so I never noticed him looking me over. With full bottles I jump back on the bike and hit the road. After turning a corner and getting to the top of the hill I see him probably about a 1/4 of a mile ahead of me. I start to peddle a bit faster to close the gap, he gave me a target to beat. I wasn't even thinking about sex at that time.

After about 20 minutes or so I finally catch up to him, I'm not sure if I was peddling that fast or he had slowed. I get up beside him and say hi again, then passed on by. This causes him to peddle faster and pass me again. We did this for about a mile or so and finally he breaks the ice. It was mostly just small talk at first about cycling, work and crap like that. We go on for about another couple of miles and he asks if I wanted to take break along on of the ponds in the reserve. We pull off, dismounted and moved to the shade. We were off the road so no campers or other riders would see us, maybe that was his plan.

He was a pretty cool guy and his named Chris. I rode a bit more than I did a week and it showed in thighs and calves. I guess at some point during our break my mind started to wander with my eyes and I got a hard on. When wearing Lycra cycling shorts it becomes very noticeable. I tried crossing my legs to hide it but he had already noticed and made his move. He placed his hand on my leg and I also freaked out as he started to caress it. I looked at him and he was smiling, and said don't worry I'm not an ax murder or anything.

He pulled my arm toward him placing my hand on his hardening cock. The only thing I could muster is I'm pretty new to this. From there I slow moved over closer to him, this gave him the signal to pull me in. We began to make out which this alone was enough to throw me over the edge. This was only the second man that I had kissed let alone swapped spit with.

This quickly escalated to our disrobing, first the tops and then our tight shorts. The Lycra was pretty useless at this point at holding back my hard on and were just absorbing the precum. I took the hint and dropped to my knees and start sucking Chris off he had a nice cock average thickness and length. After 15 mins of me going to town on his cock he pulls me and tells me to straddle him. I place my legs over him and the log and cradled my back. As we continues to adjust our positions we made out extensively with my and his tongue probing each other mouths. At this point our two cocks where nestled up next to each other and pressed between our bodies. I leaned back a little and started jacking them together using the precum as lube. It felt awesome and I really want to try and get him inside of me. Neither of us had any lotion, which was my preferred lube at this time and I didn't want to go through the previous experience of excruciating pain.

But I knew this is what he wanted, I spit in my hand and kept applying it to his shaft. At this point he figured what I wanted and did the same to my hole and tried to loosen it up with his fingers. I told him this was only my second time, and he ensured me I didn't have to if I wasn't okay with it. I made it clear that I did and it was okay. He coached me as he lined up his cock with my hole to just lower myself down easy and take my time. He ensured me that he wouldn't move until I said it was cool.

I felt the head of his cock at my hole and as he guided it in. The first inch is the hardest I've learned, I had to ease up and apply more spit to my hole and his cock. We were both pretty sweaty so it wasn't to bad and slide in with a pop and a wince. I held my position and asked if I was okay, He could see the pain on my face. I pressed on as the pain subside and let him stretch my hole. I slowly worked my was all the way to the hilt. Once at this point the pain was totally gone and had been replaced by pleasure. I began to rise and fall on his cock working it as best as I could with out falling. He picked up and met my rise driving his cock deeper.

At his point we both moaning I began to JO I knew this wasn't going to take me long and I hoped he would cum just as quickly. I couldn't believe how good this felt it was much more enjoyable than that first time. After about 10 mins I told him I was going to cum soon, and he picked up his pace. This wasn't quick enough for me and I shot my load all over his chest and mine. He kept going holding my hips and driving it in best he could I tried to help and gripped his cock with my muscle. He then screamed and moaned as he blew his load in me. We both kind of laughed as I pulled off.

I saw his cock with covers in sweat/cum/shit I apologized and he understood. We walked to the pond to clean up and cool off a bit since we both were sweaty and sticky. After cleaning up we sat and allowed the sun to dry us. About a half hour later we both suited up and headed back to the lot. It took us probably an hour to get back. By this time it was getting late and most of the walkers and hikers had gone home. I put my bike in the car and pulled on a pair of shorts. Chris came over and gave me his number, I told him I still lived with my folks so I didn't want to give him mine. He was cool with that but said we need get together again. Which we would....

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