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My First Time

Category: Gay Male
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This story is 100% true. 

I’ve known I was bi for a long time but had never had the chance to act on it. I look at gay porn all the time when alone, I masturbate to it, and recently started…toying…for the first time based on the suggestion of an article I had read. I’m glad I did because there’s no feeling quite like having something up your ass while jerking yourself off. It’s euphoric. 

Recently I had started perusing Craigs List for people who might be cool to hang out with and possibly eventually be friends with benefits, but nobody seemed interested in anything but fucking at first sight. That’s not what I wanted. I wanted to be somewhat in control of when I gave my ass up for the first time, but I also had no interest in dating a guy. Weird, I know.

Other than Craigs List, I had my eye on a guy I sort of knew in passing. His name was Eddy and he was the delivery guy for a local sandwich shop. He was younger than me, probably no older than 20 or 21, thinly built but about 6′ tall, curly black hair, bi-racial (probably african american and caucasian if I had to guess) and the most gorgeous light hazel eyes I had ever seen. 

Any time I would order food I would be able to make small talk and so over time we became friends. He would sometimes stay a little while if he didn’t have another delivery and we’d play an Xbox game. 

One time he came over I was watching a gay porn DVD. When the doorbell rang I shut the TV off and went to the door. We talked at the door for a few minutes before he came into my house to come play some games. I had forgotten I left the DVD player on and so when I turned on the TV it was in the middle of my DVD. 

“OH SHIT. Dude I am so sorry. I was just watching something and forgot to turn it off,” I yelled with embarrassment.

“Jesus Christ, man. Was that what I thought it was? Are you gay, dude?” He shouted back.

“No I’m not. I just like to look at that kind of stuff sometimes. I was just curious,” I said, using all the excuses in the book.

“Dude it’s fine, I just had no idea,” Eddy remarked in a more calm voice. “I mean every dude has been curious at one point or another. It’s fine, man. Trust me.”

“Just don’t tell anyone, please,” I pleaded.

“Who am I gonna tell? You live alone and we have no mutual friends.” He had a point. We were not in the same age group. We would have missed each other in high school by a couple years. “But I do have to go. Relax, it’s no big deal, I promise,” he said reaching for the door handle.

“Ok, thanks man. I’m really sorry, again,” I told him as he walked down my front steps.

I went back inside and shut the door. I was mortified. I couldn’t believe how embarrassing that was. I wanted to just crawl into a hole and stay there. Had I just been shoved out of the closet? Was he going to go back and tell all the workers at the sandwich shop? I went back to the couch and watched the movie and tried to forget what had just happened.

*DING DING* My iPhone text tone went off. It was Eddy. 

“Dude I’m so sorry about today. Please don’t sweat it, bro. You wanna play some xbox tonight?” We had talked about exchanging gamertags but never got around to it.

“Thanks, man. That’d be nice. What’s your gamertag?” I replied.

“I was just gonna bring my controller to your house instead if that’s cool,” He said.

“Yeah no problem. I’m available whenever.”

“Alright I’ll be there in 20”

I couldn’t believe he wanted to hang out so soon after what I figured was a traumatizing event for the poor guy. 

But my mind began to race. “Every dude has been curious at one point or another.” That was something he had said. That was odd, right? It didn’t seem like anything at the time but now that he had specifically asked to come over to my house it seemed like maybe there was more to his understanding than I had originally thought. At any rate I put that out of my mind and went on with my remaining 18 minutes until he was supposed to arrive.

The doorbell rang. 

“What’s up, man?”

“Not much. You ready to get your ass whooped in CoD?”

He seemed so normal. Maybe it really wasn’t a big deal to him.

Meanwhile, we played video games for a while until he asked a question.

“Can you show me that video that I saw today? I just want to watch it. I’ve never watched something like that before and I want to see it,” Eddy said.

“Uh…yeah sure, man.” I popped the DVD in and it started. The first scene was two guys hanging out, not dissimilar to what Eddy and I were doing. Then one pulled his dick out and began stroking it. The other leaned over and started sucking it.

The scene went on for a while until both guys came, one in the others ass and the other on the floor. By this time I had peered over at Eddy’s pants. He was sporting a huge erection and he wasn’t hiding it. The next scene began and Eddy started touching himself. He began stroking his own dick through his shorts. 

“Do you mind if I take my pants off?” Eddy asked. I shook my head. PLEASE TAKE OFF YOUR PANTS, I yelled in my own head.

Eddy’s cock was beautiful. It was cut, about 7.5″ and was proportionate. This was my moment of truth. I reached over and took his huge cock in my hand and began slowly jerking him. He looked me in the eye. He wanted this. But I wasn’t sure how much he wanted…so I asked.

“Can we go further?”


I stood up and pulled all of my clothes off (I don’t mess around) and sat back on the couch. Then I leaned over and began sucking his cock. Then it dawned on me. I had never sucked a cock before. I had sucked my dildo a thousand times but had never had a real throbbing cock in my mouth. I was amazing. The taste of his precum and the heat of his cock and balls against my face and mouth were intoxicating. Eddy was moaning. 

“Can we go further?” He asked.

“As far as you want,” I said about as fast as I could. I didn’t want this to stop.

By now I had arched my back and had my ass in the air like the bitch I am, with his cock in my mouth. He put his fingers in his mouth and then reached up to my ass and started slowly fingering me. 

I had never had someone else’s fingers inside of me, so this was a surprise.

“Oh God yes.”

Eddy kept putting his fingers deeper, deeper and deeper until they were as far in as possible. 

“Get on all fours. Arch your back and put your head on the ground,” He told me in a stern tone. I loved the control he was showing. I did as he asked.

He began tonguing my asshole firmly. He had clearly eaten pussy before because he was eating my ass like it was his own personal pussy. And it was.

“Go look in the end table’s first drawer and pull out the bottle of lube. I want your cock and load inside me. I want to feel your balls bounce against my ass,” I shouted.

He did so and pulled out the bottle of lube. 

“How much do I need?”

“Just a little.” I had played with two small objects earlier that day so my ass was already relaxed. He just needed some moisture.

Then I felt it. He had his head right on my hole and started pressing forward. I felt his head. Then his shaft. And finally his balls on mine. What a fucking feeling.

He began slowly pulling out until just his head was in. Then I pushed as hard as I could back onto his cock and surprised him. That’s when he started FUCKING me. It was my time and he was gonna give me all he had. He thrust into my ass over and over and over. His balls slapped against mine which kind of hurt but also felt amazing. This continued for what seemed like about 5 minutes but what was actually about 15 or 20. 

Then he readjusted and started hitting my prostate. 

“OH MY GOD! YES BABY! RIGHT THERE! I’M GONNA CUM!” Then I came all over the floor. 

He wasn’t done. With one more burst of energy pushed all the way in and I could feel his cum deep in my ass. He pulls out.

“Holy fuck that was amazing!” He shouted.

“Oh my God, I know. I could use that more often.”

“Me too,” He agreed.

I had imagined my first time a million times before and this matched or exceeded all of those expectations. 

About 6 months later Eddy moved in with me where we could play any time we wanted. We were never romantically involved and both of us have even had girlfriends since he moved in, but we’ve never stopped being fuck buddies and hopefully never will.

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