u/h0wardtheduc

Everyone in this REAL real story was 18+ at the time.

At 26, I was the first of my college friends to get married. The summer before the wedding, 7 of my buddies threw me a bachelor party. We rented a house in the Hamptons, played golf, went to the beach, and at night relived our college glory days at the bars.

James was my roommate for all four years of school. We were both on the hockey team, and roomed together on the road. After college, I introduced him to Jess, one of my girlfriend’s friends, and they had been dating for about one year leading up to the bachelor party.

James was slated to be my best man at the wedding, and we were sharing the master bedroom in the rental house.

James and I had very similar builds - both 6’1, both fit, though I probably had 10 lbs on him.

The last night of the bachelor party weekend, we stumbled home from the Sloppy Tuna (iykyk) around 2am, played drinking games for a little bit, and everyone went off to pass out.

After four years of rooming together, and hockey locker room culture, James and I had no issues being naked around each other. We got back to our room and he immediately geared down and jumped in the shower.

During college, we both did pretty well with girls. After college, my curiosity got the best of me and I started hooking up with guys here and there (see previous story.) James is objectively very good looking, but I had never really considered what it would be like if we crossed the line.

As he got out of the shower, I could see he was hard. His cut dick was about the same thickness as mine, and a little longer than my 6 inches. I tried to keep my eyes up as I jumped in to clean off, but I couldn’t get the thought of his dick out of my head and felt my uncut dick getting hard as I soaped up.

When I got out of the shower, he was laying on the bed on his phone. I put on boxer briefs and crashed next to him. I could see he was texting Jess, so I asked how she was. He said “she misses me” and turned his phone to show me a video of her rubbing her pussy.

“Unbelievable” I said. James passed me his phone and there were hundreds of pics and videos of Jess - solo and with him. I swiped through as he told me what a slut she was behind closed doors. Maybe it was the tequila, or maybe it was watching Jess take his dick deep in her mouth, or maybe it was the POV view of James fucking Jess from behind, but my dick was hard as a rock through my boxers.

“You like what you see?” James asked. It was pretty obvious that I did. I peered over and could see his bulge growing too. I had 100 things running through my mind - we’ve never crossed a line, why is he showing me all these videos of him and Jess like this? “So fucking sexy, I wish my fiancé was into taking more videos” I said.

“We like watching them after, but Jess thinks I delete them. I have a hidden folder where I save them all.”

James laid down and his leg brushed mine. By this point, he was very obviously hard too. We looked at each other, and both had the same idea. “Would it be weird…” I started before he interrupted “I don’t think so” and slid his hand into his boxers. I did the same, and we both started stroking our dicks while watching Jess suck him.

He was the first to take his dick out, and it looked better than when he was getting out of the shower. James had a slight bush, and was stoking his 7 inch dick slowly. I took my boxers all the way off, put my left leg over his right leg, and started stroking my 6 inch shaved and uncut dick in my right hand while holding the phone in my left hand.

Again, James took the lead and moved his dick to his left hand and reached across with his right hand, wrapping it around my uncut dick.

We looked away from Jess at each other, and he said “have you ever..” and I cut him off this time “Played with guys? Oh yeah.”

“I was going to ask if you’ve ever sucked dick” James said. It felt like an invitation, so I dropped the phone and said “let’s see how I compare.”

I climbed between his knees and started kissing his bush and the base of his dick. He moaned, and I walked my tongue up his smooth shaft before licking his head and taking it in my mouth on the way back down. I added a hand as my head bobbed up and down, looking up at him. He grabbed his phone, and said “I need to add this to the hidden folder” as I got in a rhythm and worked his hard dick.

I rotated my body so I was laying next to him, with his dick still in my mouth and mine near his face. “First time for everything” he said as he took my dick in his mouth for the first time.

We laid side by side, stroking each other, sucking each other, and moaning. The feeling of his dick in my mouth and the sight of mine in his was overwhelming. “I’m getting close” I said and he was too. We got on our knees facing each other and I grabbed his phone in my left hand and hit record as we rubbed our wet dicks against each other and stroked them. I was the first to cum, shooting rope after rope on James’ dick.

He kept stroking his cum-covered dick, harder and harder, really trying to make it happen. I laid down perpendicular to him, so my head was under his dick. I opened my mouth and stuck my tongue out inviting him to slide his cock in my mouth. As soon as I tasted his dick, he started pulsing and i wrapped my lips around him taking his full load in my mouth.

We both laid on the bed, totally spent. Neither of us really knew what to say or do. My phone beeped, and I reached over to grab it. I opened my texts and there it was, from James, a 30 second clip of me sucking his dick. He might have been my best man, but I was just another slut in his hidden folder.

I always knew I was bi. I played hockey in college and never had any trouble getting girls but I always fantasized about sucking dick. Unfortunately a small conservative school wasn’t exactly the ideal setting to explore my sexuality.

A year after graduating, I traded in my skates for a tech sales job, and was effectively living out of a suitcase and collecting more Marriott points than I could ever need. This was in the mid 2000s, before dating aps and reddit exited, when Craigslist was to place to go for naughty fun. In each city I’d visit, I’d peruse the M4M ads, even responding to a few here and there.

One night, I was incredibly horny and decided the time had come for me to suck my first dick. I put an ad on Craigslist “M4M uncut athlete seeking similar… 6’1, 185lbs, 6in shaved uncut hosting at airport Marriott. Looking to swap head and see where it goes.” I had managed to stay in pretty good shape in the year after graduating, despite spending no time on the ice, and attached a shirtless pic to the post.

I ordered two bottles of wine to the room and popped the first one as my inbox started receiving responses.

After a lot of back and forth, I seemed to have a connection going with a gay guy in his early 20s so I told him my room number and waited for him to show.

Around the time I finished the first bottle of wine, there was a knock on my door. I could barely walk over to answer it because of the nerves. I opened the door to see a gorgeous guy about my age, much shorter than me at about 5’7, with shaggy blonde hair and a tight fitting pink polo

I invited him in, offered him some wine, and we chatted a little. He wanted to know if it was really my first time, why I wanted to hook up with another guy, and what I was comfortable with. I sat on the bed while he stood across the room and carefully considered my answers before he agreed to show me the ropes. After a couple minutes of awkward chit chat and a glass of wine each, I stood up and walked over to him, and slowly leaned in to kiss him.

The first thing I noticed when kissing another guy was how prickly his upper lip was. Our tongues twirled briefly before he pulled away and looked at me as if to say “do you still want to do this?” I pulled him closer and we shared a long passionate kiss. As our lips locked I pulled off my own shirt and he rubbed his hands all over my abs and chest. I moved my hands from his hips to his belt and removed it before unbuttoning his pants and pulling them down. His pants and my knees practically hit the floor at the same time, bringing me face to face with the first dick I’ve ever touched besides my own.

I’m not hung by any means at 6 inches, and his dick was a little smaller than mine. I could see it twitch as it got hard right in front of me. It was cut and smooth and he had just a little bit of stubble growing back in. I wrapped my right hand around his dick and started to lick the tip, then up and down the side of the shaft, before putting his whole head in my mouth.

I started bobbing my head back and forth taking him deeper and deeper into my mouth, feeling his dick hit the back of my throat and gagging a little. I looked at the full length hotel mirror on the wall and felt like such a little slut watching myself take my first dick.

He grabbed me by the hair and pulled me up, kissing me deeply and tasting his dick on my mouth before pushing me back onto the bed and pulling off my shorts. He climbed between my legs and took my hard dick in his hand before going all the way down on it, effortlessly taking me into his throat. He worked my balls with his right hand and my cock with his left, pausing to slip his tongue under my foreskin and swirl the head of my dick.

As he worked my dick with his mouth, he licked his right index and middle fingers and his right hand started inching lower from my balls to my back door. I had often fingered my own ass while jerking off but felt a rush of electricity and let out a moan when his finger first brushed my asshole, getting it wet. He asked if I liked that and I nodded. He lifted both of my legs, pushing my knees to my chest revealing my shaved and tight asshole. All at once, he placed his warm wet tongue on my balls and slurped his way down to my hole. I was in heaven as his tongue circled my asshole, gently poking and prodding it, leaving it soaking wet. He let my legs back down and slipped one then two fingers in my ass and then took my now dripping dick back in his mouth.

It hurt a little but my ass soon adjusted to having two fingers sliding in and out as he continued to work my dick. I told him I was getting close but didn’t want to cum yet and that he should lay down. We switched spots and I knelt between his legs and began to again gag on his dick. I kept my hands on his thighs as got more comfortable bobbing my head on his dick and taking him deeper.

Again, I wrapped my hand around his dick and synced up the rhythm of my hand and mouth and really started to work his dick. He told me he was going to cum so I kept working my hand and stuck out my tongue right at the tip of his dick inviting him to shoot his warm cum on my tongue. As he finished, rope after rope hit my tongue and dropped back down covering his dick and my hand as I continued to stroke his orgasm.

Proud as I was after making another man cum for the first time, I climbed up and straddled his chest, presenting my hard dick practically in his face. He reached around and slipped a finger in my ass and told me he wanted to taste my cum. It only took a couple thrusts before I exploded in his mouth.

There was a little bit of awkward post-nut conversation, before he got dressed and headed out, leaving me alone in my hotel room as a newly minted cock sucker.