First Time Around the "Block"

Why is it that when so many people are in a relationship, that the feeling to fool around with others seems to be at its strongest? This question seems to run through my mind constantly. But temptation won this time, as it so often does for insatiably horny 24 year old men like me.

I had a girlfriend at the time, we had been dating for close to a year. She was bi-sexual herself and I had no problem with that. In fact, it was a turn on for me. I caught myself fantasizing about her doing things with other women. What ran through my mind, very typically, were those lesbian cliches you watch online. You know the ones I mean. Two greased up women, naked and breathing heavily as they pleasure each other. Kissing one another with a lot of tongue action. Anyways, the thought of my girlfriend being a part of that got me hard in an instant. Here's the kicker, she didn't know I liked men as well. I hadn't admitted to myself until recently before that I was definitely bi-sexual. But once I did, I fully accepted it and began to feel some of that weight off my shoulder. Obviously I didn't want to put my relationship in jeopardy, so I kept it all a secret. Besides, it was more fun that way. Being away from her and being bad and then being together and having to behave. It was all so exciting that way. That's when it all began.

David and I met on Grindr. He had just moved from out of state and only lived a couple towns over from me on the other side of the city. He was definitely my type. Tall, stocky, bearded, with a nice hairy body. Just your everyday bear. We had only been chatting for a few days before we exchanged numbers. We checked off the usual conversation topics. What we did for work, hobbies, interests, etc. As well as the 20 questions: sexual interests portion. We had a lot in common there. I can't say on a purely friendship based level that we'd have gotten along. But in the bedroom there was endless fun to be had between us. So I asked him if he ever wanted to hang out. He said yes and we agreed to just get dinner and some drinks and see where it led. We were both comfortable with the possibility of there being no connection between us and were completely prepared to end things that night without having done anything "naughty."

So the day came. Friday afternoon I went and got my haircut after work. In all honesty the majority of that was me actually needing a haircut, but the rest was me wanting to look good that night. I took the train up through the city around dinner time. We texted back and forth the whole way and we had already agreed on a sushi spot about halfway between the station and his place which meant none of the awkward tension of trying to decide where to eat.

I got off the train and took my time walking over. It was only three or four blocks but I didn't want to be the one waiting. I made sure he got there first and as I came around the corner I spotted him standing near the door. I felt some nerves come over me but I was also looking forward to having a nice meal and at the very least, making a new friend. It ended up being just that, a nice meal, quiet but not so much that it was awkward. There were nerves and I'm sure he felt them as well, although he didn't show it very much.

I had probably pounded two drinks before the food even came out. I'm more talkative that way though so it was fine. We went through some very "mature" dinner talk (not the dirty kind of mature) and after eating, sat for one last drink. When it came time to head out David suggested ice cream. I said yes because I hadn't prepared myself to go right back to his place yet. We sat and licked our cones, talked a little more, enjoyed the setting sun and the shadows it cast over the tall buildings and then out of nowhere.

"Do you wanna go back to my place?" He asked abruptly.

"Yeah sure," I replied.

So we walked to his apartment, not far from where we ate, got in the elevator and that's when my heart started racing. I could feel my cock getting hard and I knew it was at least somewhat noticeable through my joggers. I felt ready though. I had no clue what was going to happen but I knew I wanted it. I knew I wanted him. I had spent the whole dinner looking at him. Looking at his shirt and trying to imagine what it looked like under it. I wished I had a view down to his crotch at the time. I had a feeling he was sporting a bulge for a good portion of our meal. God knows I was. We got off the elevator and I half wished it was a long walk down the hall. It wasn't, his door was the first one on the right. So we walked in and he offered me a seat. His place was messy, like not just your average single guy apartment messy, this was borderline slobbish. But that wasn't my concern. In fact, all my concerns seemed to be so far away at that moment. We sat and talked for a few minutes. Exchanged glances at each other, checked each other out a few times and then he asked if I wanted to lay in bed. I followed him in the bedroom and he immediately started taking his shirt off.

"Shit," I said to myself. "Is that how we do this?"

I followed suit and started undressing myself. He was silent, as was I during this. I got all the way down to my underwear and stopped myself.

"Don't be so easy," I thought. "Maybe he's not THAT interested."

I laid on his king size mattress, which was on the floor. I thought that was strange, that he didn't have a bed frame. Didn't matter. Then it all started.

His lips met mine before we could even continue our conversation. It was all so sudden that I had no choice but to go along. We made out pretty fiercely for a few minutes before I felt his hand begin to caress the inside of my thigh. That was always a weakness of mine. I knew what it meant though. I was so horny that I grabbed his hand and placed it firmly on my throbbing cock. He stroked me through my underwear, I could feel the precum oozing out of my thick, ever wanting cock. He started to pull my underwear down around my legs and I felt his big, warm hands caressing my shaft and then my balls. I began moaning.

"Oh fuck. Mmmm that's so good," I uttered.

"You like that?" He asked.

I was embarrassingly close to blowing my load all over the place that I could barely speak.

"Yes. Mmmm yes," I breathed.

I began to cum and I knew it was going to be messy. I had a nice load built up from having not jerked off for a few days prior. I spewed my load out which ended up on my stomach and even a shot to the chest. My head laid in the pillow, restless for a minute as I felt my body start to relax itself. Then I looked up at David. He was smiling at me. I wanted him so badly at this point. I thought to myself that I'd do just about anything with him now. I looked and his hand was covered in my cum which he began to lick off, one finger at a time. Then he leaned in and we locked lips once again. I could taste the faintest bit of what I assume cum tasted like and I thought nothing of it. Just as everything to this point had, it felt so right that I couldn't help but smile a bit as my tongue explored his.

I figured by now it was time to return some of the favor so I started following what he had done. I began feeling all over his body. His chest, legs and then what was between them. I couldn't believe how natural this all felt. It was like I had done it before. I hadn't ever felt another man's cock. I wasn't sure what to expect. But it was around this time that my hand found his thick, throbbing member. I could feel he had already let out some precum through his boxer briefs, the same as I had. His cock wasn't much different than what mine felt like. It felt about the same size too. Was that a good thing or not? I didn't care. I began stroking him and gently cradling his balls in my hand. Like me, he began moaning.

Fairly loud however which made it hard for me to really focus on what I was doing. He was loving it so much that he pulled me in to kiss me some more. Our bearded faces were pressed against each other, I continued stroking him and without much warning, he began to cum. It was so sudden that all I did was keep stroking him. I could feel his body shaking somewhat as I milked his beautiful meat. His cum began to ooze out very slowly. I could tell he was having a nice, prolonged orgasm as I continued to gently stroke his pulsating cock. Each pump followed by another stream of warm, sticky cum. I licked my lips as he finished and looked at him with as much lustful intent as I had ever looked at anyone and I found myself licking his cum off of my fingers.

"Oh wow" I thought to myself, "did I really just do that?"

He watched as I enjoyed his seed. I could see he enjoyed the sight of me tasting his load. He even helped me finish in cleaning him up.

"How'd it taste?" He asked.

"Not what I expected it to be like, but not bad," I replied.

We laid down with the lights off and held on to each other for a bit. Gave each other a few more tongue laden kisses and made sure to give some of the more sensitive areas that last little bit of attention. It was obvious we were both a little tired so I rolled over to check the time on my phone.

"Wow it's late" I said, "I have to make sure I make it back to the train before they stop for the night."

David looked at me and thought for a second.

"Or you could stay here. Tomorrow is Saturday and I've got nowhere to be," he said.

I felt almost a little guilty at this point. But I knew that what we had done gave me the best physical high I'd gotten in a long time and without much hesitation, I agreed. I wasn't even dressed so I got back in bed with him and felt his warmth. His big, bear-like body kept me cozy. He ran one hand through my hair and held my hand with the other and we dozed off after a while.

More to come...