First Experience with a man

It was summertime in the Virginia Beach area. The weather was typical, hot, and muggy. I was there for some work-related business, spending about three months of my summer in the area. It wasn't bad, paid hotel room and money for food. Just work from 8 to 5 during the weekdays, weekends were free to me.

I was in my early twenties, not bad looking. I had a runners build since I would run everyday for working out. Six feet, about 185lbs, still some lean muscle on me, dirty blond hair, green eyes, and an average sized cock about 6" cut. I had a few girlfriends before, but nothing to exaggerate about. I've never been with a guy, nor had the thought about being with another guy before coming up on my mind until this summer.

I was currently single during my work trip, which meant a lot of weekends were spent at the bars. I was looking for some fun, just like any other typical horny young man, but was constantly striking out. I was sitting on my bed in the hotel room when I had a notification on messenger for a chat. It was my ex. She had cheated on me the year prior with another girl and left me for her. Needless to say, I was hurt, but I still had feelings. So, I opened the message. It was typical: "hey, how are you doing?", "what are you up to now a day?". Basically, small talk. The messages then turned in to why she cheated and why she was with another girl.

After a frustrating conversation, I decided to go to the gym and run for a bit. As I was running on the treadmill, listening to my angry music, my mind started to wonder. What was the big deal about being with someone of the same sex? Is it really that bad off? I started to think about all the pornos I had watched and started to think about the guys in them, their dicks, and wondering what it would feel like to have them inside of me like those pornos. Before long and without realizing, I had gotten a hardon while running thinking about being fucked in the pornos. I faked my shoes being untied so I could jump off the treadmill and bend down to keep my dick from signaling me out in the middle of the gym. Thankfully the gym wasn't during rush hour, so it wasn't packed. After calming myself down, I stood up and decided that was enough running for the day.

That entire week I couldn't stop my mind from wondering to guys. I figured maybe if I watched a gay porno and jerked off to it, I would get the fantasy out of my head. So, I found myself searching the web for gay videos to watch. Most were turn offs, being big hairy guys. Buy stumbling on to sissy and twink area, I started to find myself searching those areas. I was searching the twinks tab in my hotel room wearing boxer briefs, gym shorts and t-shirt. The more I searched the harder I felt my dick grow in my shorts. I started rubbing myself in my shorts with one hand while the other hand worked the mouse still searching the videos. Finally, after searching and rubbing my dick, I was too horny to think anymore. I decided on a video of two blonde twinks outside fucking each other. As the video played, I fast forwarded past all the kissing and rubbing they were doing. I wanted to see the good stuff. My cock was so hard it started to hurt, I had precum soaked through my briefs and gyms shorts. As the video kept playing, I took my shorts and briefs off to give my cock some air and room. I started to work my cock in my hand at the pace of the two guys fucking on the video. I was so horned up it didn't take long before my own orgasm cascaded over my body. Usually I can cum hard, but never like this. I shot three full loads of cum up over my head into my hair, before the next few shots down on my chest, and then finished drooling over my hand. Surprised at my own cum shots, I closed the video and decided to clean up.

If I thought watching a gay video and jerking off would get that thought out of my head, I couldn't have been more wrong. Watching twink videos was now the new norm. Come in from work to the hotel, relax for a bit, grab the laptop, find another video, jerk off and cum. Everyday. Wash -- rinse -- repeat. Finally, after about two weeks of watching gay porn, the horniness and curiosity got the better of me. I decided to look online at personal ads and see what all was out there in the real world. I found a website that allowed for personal ads, in more of the sexual nature, and started rummaging around on there. It was full of the typical older, more hairy, heavier set guys. The ones that were turn offs immediately for me. The ones I did find around my age and type, the skinny twink young guys, were all mostly bottoms. I was looking for a top as I wanted to know what it felt like to be penetrated by my first cock. After a few nights of frustrated searching, I decided to take matters in my own hands and posted an ad searching for my own top. The responses were insane. By the next morning I had over 100 messages in my inbox from tops wanting to play.

After searching through the messages there was one that caught my eye. He was in his early thirties, a little short, stocky but solid build. His cock caught my attention the most. Being clean shaven, it was only about five to six inches long, but the girth was there. He had to be at least 3 inches across, not around, but across. We started chatting up and decided that it would be best if I came to his place since it was a bit more discreet. We also set up to come at 10 at night that coming Friday.

Through the rest of the week, I couldn't stop my nervousness. Would I like it? What if I didn't? Did this mean I was gay? But I was also excited. Deciding to keep my excitedness and horniness, I quit jerking off for the week to save myself up for the upcoming event on Friday.

Friday finally arrived, and I was so nervous and excited I couldn't keep my mind on the task at work. Thankfully work was dull and simple, so it wasn't noticed of my distraction. With work complete, I went back to the hotel and showered, finding some simple khaki shorts and polo shirt. I ate a light dinner as my stomach was in knots with nervousness. Finally, the time came to leave and drive to his house. It was about a thirty-minute drive, but it felt like only minutes. Even though I was completely soft, my dick leaked precum the whole drive over. I could feel the wet spot on my boxer briefs.

His house was in a gated community. It was really lavish and nice looking. I was so nervous I could feel my stomach in my chest, my throat dry and tight. When I knocked on the door, he answered immediately. He looked exactly as he did in his pictures. That was a bit of relief. Welcoming me in, he led me to the back of the house to the master bedroom. The house was dark except for the little bit of light coming from the bedroom. I entered first, noticing the large bed, walk-in bathroom, and closet. In the corner was a porno playing on the tv. It had a girl getting rammed by a built muscular hung guy. He asked if I was comfortable and liked what I saw. I told him I was nervous but enjoyed what was on tv. When I looked back at him, he had dropped his gym short and took off his shirt. Standing fully naked in front of me, I could tell how worked outside in the sun all day being tanned. His arms were defined but not large. He had a small stomach on him but nothing unattractive. His cock was already hard, sticking straight out in front of him.

"Come suck it" he said.

I went over and knelt in front of him. Staring at my first cock in front of my face, other than my own, my curiosity overtook my nervousness. I took his cock in my hand, feeling his hardon like steel. The warmth in my hand let me know that it was real and not just a dream or fantasy.

"Taste it" he said.

With that comment, I opened my mouth and took his cock in. It was warm to my tongue. I could feel the stiffness in my mouth. Taking him fully in to my mouth he just touched the back of my throat. It was his thickness that surprised me. Having to fully open my jaws to take his cock in, started to give me a little bit of soreness. I kept bobbing my head up and down, keeping the saliva going. I'd twirl my tongue around his cockhead when I backed fully up, then take him down as far as I could go. I was surprised that he didn't have any precum as I sucked his cock. I could tell that I had basically soaked my own underwear with my precum.

"Take your clothes off and let me see you now" he commanded.

I stood and took my clothes off. My cock was semi rigid from the excitement but not fully hard still with nervousness. But my precum was running like a faucet. A string drippled from my tip down my leg as I took my underwear off. He stood in front of me gazing at my body up and down, stroking his cock.

"Lay on the bed on your back".

I moved to the bed and lay on my back with my butt on the edge. I faced the tv so I could watch the porno at the same time. He grabbed some lube from the nightstand, pouring some on his cock and continuing to stroke it. When he was ready, he positioned himself between my legs, with my legs bent over his shoulders.

"Relax. You're going to like this" he said.

Knowing how big around he was, I knew in my head that I needed to relax so he could enter me. I tried to push like using the bathroom as he entered me. I knew what a finger felt like as I used my own over the previous weeks while watching the pornos. But this was a new feeling. I could feel the heat of his cock as he pushed his head into my virgin hole. I felt my own asshole stretching out, allowing him in with full entry. I was surprised that it didn't hurt. He pushed all the way until he bottomed out on the first try inside of me.

"Wow, I'm surprised. Most guys have trouble taking my girth. You sure you haven't done this?"

"No sir" I replied. "This is my first time with another guy".

"Well, you feel amazing."

With that he pulled back out, leaving my ass with an empty cold feeling. He immediately pushed all the way into the hilt again in one thrust. After that he started to move back and forth, fucking my now no longer virgin hole. My cock was rock hard and leaking precum like a water hose. I grabbed my own cock and started to jerk it to the motion of his fucking my ass. He started to pick up the pace, moving faster in and out of my ass. He never thrust hard, just a steady pressure at a faster rate. I kept jerking off my own cock watching the precum sway around.

"I'm gonna cum soon. You ok with it in your ass?" he asked.

"Yes" was all I was able to say.

I was lost in the feeling of my ass being stretched, feeling the motion in and out, the warmth of his cock inside of me. It was not like I had imagined watching all the gay videos in my hotel room. It felt amazing have a cock inside of me. A few seconds later, he started tensing up. I could feel his cock and body getting harder, knowing that he was soon to cum. I jerked my cock faster, trying to time my own orgasm with his. With one last hard, deep thrust, he buried his cock deep in my ass and came. I could feel his cock twitching inside of me. I didn't feel the cum, just the action. Feeling his cock cumming, knowing I was being bred by another guy, my own cock spurted my cum. Again, with the same force, my cum shot all the way up into my own face and chest. As I lay there calming down from my orgasm, he stood there calming down from his, with his cock buried in my ass. When he regained himself, he pulled out of me. That feeling of empty coldness returned. I didn't realize that the coldness was my asshole being gapped open and the air rushing inside of me. I finally figured it out when I stood up and felt his cum leak out of my ass and down my legs. He led me to the shower and let me get cleaned up. We small talked while I showered, him asking if I would be back again. I told him I was for sure, but my trip was ending soon.

Leaving his house that night I wouldn't be back to see him as my trip came to an end. But that night opened my eyes, and future fantasies, to so much more. But that's for another story.