First Encounters

By Twonight

Published on Nov 23, 2023

Gay

First Encounters - Part 6

Before I get into this story, I would like to cover an administrative detail. Many of my readers have been unable to locate my other stories. The following is a list of the story titles and they can all be found under Prolific Authors / Twonight:

Black Dorm World's Hottest T-Girl The Awakening Star Cruiser The Inmate Shocking Encounter Olympiad Turning 18 The Gamblers The Realtors The Kidnapping The Fluffer First Encounters

Please send feedback to twonight@excite.com. I really enjoy hearing about your first sexual encounter so tell me about it.

As I mentioned above, I really like to hear about my readers' first sexual encounters. I have gotten a lot of great stories. Although I can't vouch for the validity of them, I decided to share a few of them with others, with the names changed and no references which would reveal anyone's identity.

Ok, on with the story:

Jeff's story:

I knew I was gay. I had known it since I was about 14. Now I was a freshman in college and I was really anxious to sample some man-to-man sex. I just didn't know how to find other gay men. I was a nice looking guy with a good build, a hot ass, and a nice, thick dick. I figured someone would just approach me at some point, but it hadn't happened yet.

I was in the community shower at the gym one day, when a hot looking guy joined me. He was really giving me the once over and his hot body caused my limp dick to stir. I tried to cover it up, but he couldn't help but notice.

"Aw, that's sweet," he said with a smile. "I didn't think you noticed how great I look."

I was stunned by his directness.

"It's OK, dude," he added. "I was checking out your equipment too. That's how I noticed you getting a boner over my ass."

"So you're gay?," I asked sheepishly.

"Oh my God you're adorable. Are you a virgin?"

"You mean, have I ever done it with a guy?"

"Yes sweetie, that's what I mean."

"No, I haven't. But I want to."

"Well you've come to the right place baby. Wanna join me back at my place for a crash course in Mansex 101?"

I quickly agreed and he told me his name was Mark. I eagerly followed him back to his place. He was a junior, living in an off-campus apartment with two other guys. When we got there, he introduced me to one of his roommates, Chad. He was a nice looking black guy with an interesting bulge in his pants. I had no idea whether he was gay, but I sure hoped that he was. Mark made me a drink and we sat and talked with Chad for a few minutes.

"Jeff's a virgin and he wants to fuck me bad."

I couldn't believe that he just blurted that out in front of another guy.

"That's hot," Chad said with a smile. "Is this a private party or can I join?"

"Sure you can," I said a bit too eagerly.

Mark laughed and started to strip right there in the living room. Chad joined him and in less than a minute, there were two hot cocks dangling in front of me. Mark began to remove my clothes and Chad helped him. I reached out and greabbed both of their cocks. I couldn't believe the rush I got just from stroking them and feeling them harden in my hand. I wanted them so badly. When they got my clothes off, Mark immediately went down on me. When my hard cock entered his mouth, I thought I would pass out. His lips and tongue were like a velvet vise, squeezing and sucking my cock. I recovered enough to pull Chad's cock up to my mouth where I began to lick it carefully, still unsure of myself.

"Just do what Mark's doing to your's baby and everything will be fine."

I took his advice and began to mimic Mark's technique. Chad's cock grew to new heights and I suddenly had a mouthful of hard, black dick. I explored his thick, veiny shaft with my lips and tongue. I licked his balls and on up his shaft. I took it deep, although not as deep as Mark took mine. He was incredible. After a few minutes of this, we switched and Chad sucked me as I sucked Mark's hot cock. I was getting very hot by now and warned Chad that I was about to cum. He backed off and said that I wasn't allowed to cum until I got a piece of ass.

Mark agreed and shifted into a position on his knees with his head resting on the sofa. Chad got some lube and coated my cock and the inside of Mark's butt with a liberal amount. He then stroked my cock and moved me into position behind Mark. I was scared but oh so ready for my first fuck. Chad helped me insert it and Mark moaned with pleasure as my big log entered his butt. I started moving slowly back and forth, but Mark was more than ready and he began to push back to meet my thrusts. It was so hot in his ass and I was on fire by that point. I began to really fuck him hard and he just moaned his approval.

Chad moved under us and took Mark's cock in his mouth. He really worked him over as I continued to pound Mark's butt with my thick cock. I thought I was going to get off that way, but Chad had other plans. He pulled me out of Mark's ass and inserted his own lubed dick in the hole I had just vacated. I was kind of pissed until he told me to stick my dick in his ass. I wasted no time getting my hard cock up Chad's ass. He obviously didn't take it in the ass as much as Mark because he was tighter. The heat and pressure from his tight ass made my cock tingle with excitement. I began to thrust in time with his thrusts into Mark's ass. Chad was moaning like a bitch in heat as his cock got squeezed and his ass got stretched.

I was getting close again, but Chad beat me to it. He groaned and buried his cock in Mark's ass, shooting a steaming load of hot sperm deep in that sexy hole. When he came to his senses, he realized that I was getting close and he used his anal muscles to squeeze and milk my cock until I blasted his ass with hot, sticky cum. He kept milking my cock with his ass until I had no cum left in my balls. When I pulled out, Chad slid under Mark and sucked him until Mark unloaded in his mouth. I was curious about the taste of cum, but decided to hold off on that.

We rested for a while and I held a hot cock in each hand as we lay on the floor. I couldn't get enough of the feel of a man's cock in my hand. I love to squeeze and stroke them and I really loved it when they grew hard. Mark had just managed to get me hard again and was going down on me again when Ken walked in. I was stunned at how beautiful he was. He laughed as he surveyed the scene and asked if it was too late to join the party. Mark told him to get his ass in gear and he quickly stripped. His cock was the most beautiful thing I had ever seen. It was long and thick with veins popping out along the shaft as it hung well down his thighs. He was totally shaved and his balls looked like ripe melons hanging from the base of his huge prick.

I quickly moved to get that monster in my mouth. He sighed and moaned as I ran my lips along his shaft. I had not thought about getting my own ass fucked, but I just had to get this gorgeous dick up my ass and see what was so great about getting fucked. When I told Ken what I wanted, he smiled. When Mark told him I had a virgin ass, he smiled even more. Chad and Mark positioned me on the floor and held my legs open wide. They got more lube and Mark began to finger me with his index finder. It hurt a little, but I quickly adjusted. The second finger was a bit more challenging but, eventually, I adjusted to that. The third finger was not much worse than the second and they finally decided I was ready for Ken's monster.

Ken positioned himself over me, then leaned down for a deep kiss with lots of tongue. I was so hot after that, I just had to get laid. He moved down to my cock and licked the shaft all the way down to my balls then back to the head. He took the head in his mouth and, in one motion, took my big cock all the way to the base. He proceeded to move up and down, taking me all the way into is throat, then almost all of the way out of his mouth. With each deep thrust he licked my shaft and squeezed it tightly with his hot lips. His technique was amazing. Just when I thought I was going to explode, he stopped. I would have been happy, at that point, to just cum in his mouth and collapse, but he had other plans for me.

First he lifted my ass and the guys slid a pillow underneath me. This positioned me perfectly for his cock. Next, Ken lubed his cock and positioned the head at my anal opening. Mark stroked my cock to distract me and keep me really horny. My legs were spread wide as Ken pressed forward, his hand gripping his shaft to keep it from bending as he encountered resistance. After a couple of attempts, the big, mushroom-shaped head broke through the tight, elastic ring and two inches of hard cock followed. I gasped at the way he was stretching me, my mind quickly reconsidering my foolhardy plan to have such a huge cock deflower my poor ass. After a few seconds delay, Ken thrust forward and added four more inches of thick meat to the three that were already in there. I glanced down to see another four inches poised to penetrate me and cringed at the thought of it. Finally, he pressed forward again and buried his cock in my butt to the hilt.

At that point, if you had told me that someone had rammed a log up my ass, I would have believed it. I just wanted him to take it out. I think he knew how I felt, so he leaned forward and began to kiss me again. His tongue explored my mouth as his taut stomach brushed over my cock. It was so hot that I barely noticed that he had begun to slowly fuck me. His cock moved slowly in and out, only a couple of inches at first. He continued to kiss me deeply as he increased the pace and depth of his thrusts. It hurt, but something felt so good at the same. I didn't know about the prostate at that time, but he was sure rubbing it and causing a buzz in my loins. Ken raised up and Chad and Mark were quick to move in. Mark took my cock into his mouth and Chad fed me his hot rod. I was now getting fucked, sucking cock, and getting sucked at the same time.

Ken picked up the pace even more and was now in a smoth, steady rhythm, pulling about seven inches out before plunging back to the depths of my hole. There was still pain, but the pleasure of his cock and Mark's mouth now overcame any reservations that remained. Mark decided to up the ante even more by planting his ass on my cock and riding it as Ken continued to fuck me. Ken was now pulling almost all the way out before sliding his meat back to the bottom of my bowels. My own cock was filling Mark's ass as he bobbed up and down on it and jerked his cock. It wasn't long before Mark shot his load, most of which hit my face and Chad's cock as he continued to fuck my face. Mark's blast got Chad excited and he was ready to shoot. He warned me that he was about to shoot, but I decided that I was ready to have my first taste of hot jizz. When he shot his load, I was surprised at the volume. I assumed that it wouldn't be much since he had come in Mark's ass just a short time before. Boy was I mistaken. It really filled my mouth and I was surprised by how hot and sticky it was. The taste was salty and strange, not good, but very sexy. I finally swallowed it all and Chad sat back to recover.

Now it was just Ken and me. He flipped me over and slid in behind me as I leaned on the sofa with my knees on the floor. His cock soon found its way back up my ass and I gasped as he began to fuck me again. I think it's really important for any man who wants to fuck another man to be on the receiving end at least once so he can understand the way it feels. It really is the ultimate in submission to allow another man to penetrate you and fuck you like a woman, especially doggie style. This places the fucker in a very dominant position and you are allowing him to use your body to pleasure his cock. You become a fuckhole for his pleasure. If the fucker is skilled, he can bring you great pleasure as well and Ken was very, very good. In this position his cockhead rubbed me in all the right places. The pain had almost completely subsided and the pleasure was very strong. His huge dick filled me over and over again, stretching my poor, abused hole to incredible proportions.

I finally reached the point of no return and my cock just started to blast sperm everywhere. Chad dove under and took my cock in his mouth to get the last few shots. He sounded like a man who was starving and was given a steak to munch on. That man loved to eat cum. When I was done, Ken laid me face-down, flat on the floor and slipped a pillow under my cock to raise my ass slightly. He mounted me with his legs outside of mine and his cock coming at a steeper angle. This allowed for maximum penetration and he rode me good and hard. I couldn't believe how much cock was filling my ass with each thrust. On and on it went and I was beginning to wonder if he was ever going to cum. My cock was already beginning to harden again when he screamed, "Ahhhhhhhhhh, I'm cumming!!!"

With that, I felt a flood of semen blast from his cock into the depths of my ass. The force with which each shot hit my rectal walls was incredible. I had seen porn films with guys that really blasted, but I never imagined I would feel it in my ass. Ken continued his deep thrusting until every drop was in my ass or coating his cock. He collapsed on top of me and nibbled my neck and ear. I was really getting horny now and he reached underneath just in time to feel my cock reach its full glory.

"Holy shit," he said. "You need some ass of your own dude. Would you like to fuck me now?"

I wasted no time taking him up on it and placed him on his back. I mounted him in the missionary position and leaned forward to kiss him the way he had kissed me. It was sexy to feel his limp cock, covered in cum, resting between us as my own cock explored his ass and my tongue probed his mouth. I decided to try something new and began to suck and rub his nippples as I continued a steady fucking motion in his butt. His moans were neverending as I pleasured his ass and nipples and rubbed his spent cock with each forward thrust. Before I was done with him, I turned him over and did him from behind, then sat him on my cock and made him ride me until I blasted a load up his ass. He pulled off and licked my cock nice and clean.

I stayed over that night and fucked around with all the guys some more. I let Chad and Mark have a turn in my ass and gave Ken one more turn as well. The highlight was a four way fuck with Mark in front, followed by Chad, followed by me, with Ken bringing up the rear. Boy did he bring it up my rear. When I left there the next day, cum was still dripping from my ass and I could still taste everyone's cum.

The guys graduated before I did and went their separate ways. When I graduated, I moved in with Ken in San Francisco and we have been together for three years. We both fuck around together and separately with lots of guys, but my favorite thing is still getting a rock-hard dose of Ken's cock up my ass every day. Chad and Mark are coming for a visit in the Spring and I'm really looking forward to getting a hot fourway together while they are here. Some people like to stay at a Bed and Breakfast. Mark and Chad asked for a Bed and Buttfuck and they're going to get it.

As always, send comments to twonight@excite.com. Check out my other fiction stories, Olympiad, The Gamblers, Black Dorm, The Awakening, The Inmate, Turning 18, The Gambler, The Realtors, The Kidnapping, The Fluffer, and Star Cruiser - and my nonfiction Shocking Encounter and Tess' story - World's Hottest T-Girl.

Next: Chapter 7


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