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The one I’m ashamed of

1200 words | 1 |3.67
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I’ve had a lot of unexpected sexual encounters but this one I’m not particularly proud of.

When I was 7 I met my best friend, Jason. We played baseball together and slept at each other’s houses almost every weekend. He and I were pretty inseparable. He lived in the same apartment complex that I lived in so we were never really that far away from each other. We became even closer when his dad started dating my mom. The relationship didn’t last more than 2 months but for a short time we pretended to be brothers. A few years after, I asked my mom why they broke up and she told me that he was gay.

By the time I was 15, Jason’s dad was out and had a boyfriend living with him. Jason’s mom had left when she found out and consequently moved away. Jason decided to stay with his dad so he wouldn’t have to switch schools and we could still be friends and what not.

Another reason that Jason stayed with his dad was that he was also gay. Jason came out to me one night while I was sleeping at his house. It didn’t bother me that he was gay, as I had had my own experience with homosexuality. I hadn’t told him about my prior experience and I didn’t plan on it either. I had grown into my body quite nicely and was getting regular attention from girls at our school.

One night when I was 15, I was spending another night at Jason’s house. We had done our usual thing, order pizza, played video games, listened to music. Typical 15 year old behavior. When we went to bed, we both striped down to our boxers and climbed into his king size bed. We had been sleeping like this together for 8 years and never had any problems with it. This particular night changed things, big time.

We started off by playing some game where we’d use our finger to write something on each other’s back and we’d have to guess what the other wrote. He invented this game and I’m sure it was just a way for him to have that physical contact with another male. After a few rounds we stopped and laid quietly until I felt his leg rub against mine. Assuming it was just mistake, I shrugged it off. A second one came shortly after that lasted a little longer. I was laying on my side with my back to him so I tried to ignore it and pretend I was already asleep. He scooted close to me and I could feel his erection press against my ass. I quickly rolled over.

“What are you doing?!”

“Shit! I’m sorry. I couldn’t help myself” he said rolling over in embarrassingly

Ever since my encounter with my cousin Derek a couple years earlier, I knew I was bi-sexual. Playing his writing game always made me feel those tingly feelings and always made me want to try stuff with him and when I felt his hard dick pressing against me it turned me on unbelievably. I rolled over and acted surprised because I knew if we started down this road, I’d more than likely lose my best friend. Ever since he came out to me I’ve been waiting for this moment and I had thought long and hard about how I was going to handle it.

I needed a few moments to collect my thoughts. Even though I thought I knew how to handle it, I wasn’t completely convinced. We were close friends and of course part of me wanted more. I explained to him that I needed a moment, so I went downstairs to the living room. I sat in the dark on the couch really trying to get my head around this. After 20 minutes or so, Jason’s dad’s boyfriend, Mark, came walking thru the living room completely naked. Being in the dark he didn’t see me as he went into the bathroom. When he came back thru he did notice me.

“Hey, what are doing up here?” he asked me. He had no shame. He stood there buck naked. His dick was right at eye level to me sitting on the couch and even in the dark and it was soft I could see it was impressive.

“Uh, nothing. Nothing is wrong” I mumbled out trying not to look at his cock.

“Oh God, don’t tell me you’ve never seen a dick before.”

“Of course I have” I responded. I couldn’t stop looking at it at this point. I watched it as it grew.

“Then what’s wrong?” he asked. By now he was fully erect.

My confusion still lingered. I honestly didn’t know what to do about Jason. In an attempt to make that stressful situation go away for a moment, I sat forward, grabbed Mark’s cock and put it in my mouth. Despite my confusion, the encounter with Jason did turn me on. I thought that if I took out my horniness on Mark, it’d make my feelings for Jason to go away.

Mark jumped back in shock. “What the fuck?!” he shouted.

“What? I wanna suck your dick.”

“I’m 43 and you’re 15. You don’t see anything wrong with that?” he argued.

“Look, I’m not going to get into the details but I need this. Besides, you’re hard as a rock. Let me take care of that.” I told him.

He agreed and I put his cock back in my mouth and started slurping him. After about 2 minutes I realized what I was doing and became disgusted with myself but I knew I had to finish this. It wouldn’t be fair to Mark to start him up and leave him like this. So I knew I needed to finish this quickly.

With one hand I squeezed the base of his cock and with the other I put his balls in my hand and reached my middle finger for his asshole. I started toying his hole and it wasn’t long before I hear him getting ready to cum. He put his hand on top of my head and shot his load down my throat. It was warm, thick and tasted much better than my cousins or my own. He held my head in place until I swallowed every drop of it.

As soon as I was done, I stood up and started back to Jason’s bedroom. “Goodnight” I said heading back upstairs.

“Thanks” he replied with a giggle.

I walked back in Jason’s room with no new answers and now my dick was rock hard. I got back into bed and noticed Jason was asleep already. I rolled over and went to sleep ashamed of what I had just done.

The following morning Jason and I woke up and I had told him how I felt. How I was incredibly curious about being with him but I didn’t want to ruin our friendship. He was very understanding. He agreed not to press the issue and I told him if I ever changed my mind I would let him know.

I went home ashamed. I didn’t see myself as gay but by 15 I had sucked 2 dicks and no pussies. I had awkwardly fingered a couple, but that’s as far as I had gotten. Until next story!

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1 Comment

  • Reply AC ID:fzq6jmk0k

    Hot story