Chris’s first time with a guy [MM]

Note: this is a true story. It’s kinda long and almost all m/m.

This is about a guy I grew up with named Chris. We had been friends since grade school. Chris was athletic and a good looking guy – always had girls fawning on him – and had plenty of girlfriends. Thing was, whenever we were hanging out alone, he’d get what I’d call flirty with me. Never thought much of it. The guy was constantly horny but I didn’t figure he was interested in guys.

I, on the other hand, was pretty plain. Yeah I had a few girlfriends but nothing compared to Chris. I’d had a few guy encounters as well, but was mainly into girls. Still, I rarely turned down a little male on male fun.

One day Chris calls me up and asks if I want to come by his place and hang out. Play some video games and have a few beers. Sounded good to me, so I headed over to his place. When I got there his current girlfriend Diane was there. The three of us hung out and drank a bit. Chris and Diane got a bit buzzed and went off to the bedroom. I could hear them banging their brains out a few minutes later. I tried to concentrate on my game, but the sounds had my cock throbbing.

After they finished up, Diane headed home, and Chris and I started playing video games again. Chris kept cracking sexual jokes about how I was probably jacking off listening to them and had me laughing my ass off. After awhile we got bored and turned the console off, and Chris asked if I wanted to watch some porn.

This was “back in the day” so after I agreed he broke out a couple DVDs and we picked one to watch. We settled in with two new beers and watched the movie. In short order, we were both engrossed. I knew my cock was hard, and glanced over at Chris. He was rubbing his hardness through his jeans, and I have to admit it looked nice.

Always joking, Chris started cracking more masturbation jokes. Finally I said “dude, you nailed Diane not an hour ago and you’re still horned up?” “Hell yeah” Chris said “my dick is still sticky and I want more!” We both laughed, then he asked if I thought Diane was hot. I said she was. Chris reached a hand into his pants, then pulled it out and held it out to me, asking if I wanted to smell. I took a sniff, and caught the scent of Diane’s pussy on his fingers. I told him it smelled amazing!

At this point we were both insanely worked up. The sexual tension was incredible. We both turned back to the movie, but in no time Chris had his pants undone and was slowly stroking his cock. I looked over in disbelief and he just nodded and said “go ahead, pull yours out.”

I undid my jeans and began teasing my cock with my hand. Chris’s eyes were absolutely glued to my crotch, and I was really enjoying my affect on him. He reached over and gently took my other hand and pulled it to his cock. I wrapped my fingers around it and began to slowly stroke him.

After a bit, he reached over and took my cock in his hand. Now we were stroking each other, slowly, and staring at each other’s cocks. I told him I’d love to taste Diane’s pussy. He looked at me sort of quizzically. I removed both our hands and slid onto the floor, kneeling between his legs. I dropped my mouth over his cock, first taking about half, then going lower with each stroke.

I don’t know who liked it more – Chris, who had one of his best friends sucking his cock, or me, sucking a nice seven incher with good girth that smells and tastes like a girl I’d always found hot.

Now this wasn’t the first dick I’d sucked, so I knew my way around, so to speak. I’d suck him deeply into my mouth a few times, then back off and lick the shaft a bit, occasionally dropping down to lick his balls. Diane’s scent was all over it and I enjoyed licking every bit I could.

Soon, I felt Chris’s balls begin to tighten. I backed off, and looked up at him. “Your turn” I said, and stood up. I don’t think Chris thought this all through as he hesitated a bit at my hard cock a foot from his face. After a moment, he reached up with his hand and stroked me a bit. I gently put my hand on the back of his head and eased him towards my cock. His lips parted and he took about a third into his mouth.

I asked if this was his first time with a guy. He took his mouth off me and said yes. I said to go slow, I’d guide him. He never got past about halfway, but after a few awkward (and slightly painful) minutes he was doing a decent job.

I felt myself getting close and told him so. He stopped sucking me and said he didn’t want cum in his mouth. Ok, so what do you want to do? Chris stood up and said he’d be right back.

He came out of the bedroom with a bottle of KY, and I immediately knew what was next. I was game, and asked what he wanted. He told me to get on all fours.

I got on the floor on all fours and spread my legs a bit. I felt the chilly lube on Chris’s finger as he started to try and slide it inside me. He was way too quick and rough, so I had him slow down a bit and instructed him in lubing me up. Once I felt I had enough, I said I was ready. Chris literally jumped up and tried to cram his cock directly into me! I yelped and told him to wait! (Damn rookies!)

I grabbed the KY and lubed his cock for him. “Now GO SLOW and listen it me” I said. “Put the head against my hole and gently press.” Chris did as I asked, and after a moment I felt his head pop past my ring. I moaned a bit and told him to hold still. Chris was thicker than me, and definitely thicker than I’d had before. After I had adjusted to his thickness somewhat I pressed back on him, rocking a bit back and forth until he was fully in me.

“Ok” I said “go ahead.”

That was a mistake. Chris grabbed my hips and began absolutely railing my tight asshole. I tried to slow him down, but now he was like a man possessed, thrusting his seven incher into me with abandon. I dropped down to my forearms and arched my back a bit, and eventually it felt pretty good! I decided to just let him have his way, and after about ten minutes of wild thrusting I felt his cock pulsing jism deep into my bowels.

We were both sweating, and his now limp cock slipped out of me. I hustled to the bathroom and expelled his cum, then cleaned up a bit. When I returned to the living room, Chris was sitting naked on the couch. He looked a bit dazed. I asked if he was OK and he said yes, he was just kind of overwhelmed. Then I asked if he was ready.

“Ready for what?” he asked. I said I wanted to fuck him now. I guess he was having some post nut clarity, and began trying to dissuade me. I said I’d make it feel really good for him, but he was skeptical. I got the KY and told him to slide forward to the edge of the couch and that if at anytime he wanted me to stop I’d stop. Warily, he agreed.

I knelt between his spread legs, and gave his cock and balls some gentle rubbing. Dude started getting hard AGAIN! He was like a damn machine! I lubed up my finger and began massaging his tight hole, still gently playing with his cock. Eventually, he relaxed and I was able to slide a finger inside. He was fully hard now, and I kept him distracted by slowly stroking his greasy dick.

When it felt right, I took my hand off his cock and lubed my own member up. Chris was now almost like in a trance. His eyes were half closed and he was moaning. I asked if he was ready. He just nodded. I removed my finger, lifted his legs and pressed the head of my cock against his hole. Gently, I gradually worked my way inside. He felt amazing. Once I felt his cheeks against my crotch I started slowly and gently pumping my cock in and out about halfway. Just kept up an easy rhythm. Chris’s face never changed, he stayed in his half trance and took me deep.

After about five minutes of slow strokes into his tight hole, Chris’s eyes got wide. His face looked surprised and his jaw dropped. Suddenly, his cock began to shoot cum across his stomach. He moaned deeply as he came, amazed that he had shot without being touched.

Once he finished, I simply said “my turn” and began moving faster. Now I was really fucking him, and he was like a rag doll, spent after having cum three times that evening. I hammed away until I knew I was about to explode, then quickly pulled out. I looked at his cum spattered stomach and added my spunk to his, cumming across his stomach and chest.

Exhausted, I leaned forward, my nose inches from our combined juices. I got a devilish idea – I scooped up some cum with my finger and quickly slid it into Chris’s mouth. This shocked him out of his lull, and I laughed. “Didn’t taste bad, did it?” I said, and dropped my mouth down to his stomach, licking a bit up myself. We both laughed again, and went to clean up.

Source: reddit.com/r/gonewildstories/comments/1316v82/chriss_first_time_with_a_guy_mm