Miles - First Time Bareback

It was 1993. I’m Miles, 23 years old, pretty skinny at 5’10” and 130lbs, a nerdy guy with glasses who blossomed while going to NYU for four years. Most of my social circle had become strictly gay men, some more flamboyant than others, some more promiscuous than others, but all good guys. I was what my friends called “passable.” Meaning I passed as a straight guy. A bookish guy, but straight nonetheless. It was a blessing and a curse.

I had been sort of dating a guy named Morgan for the better part of five months, and he was quickly becoming my guy. He was everything I wanted in a boyfriend. He’s handsome, 26, with masculine features, light brown hair with natural red highlights, about 6’1”, and carries more muscle than most of my friends. If I didn’t know he was secretly as nerdy as I am, I’d think he was a jock. He comes from a well-to-do family on the Upper East Side, but he lives in Greenwich Village. I’m in Alphabet City, so when we met at Stonewall after a night of drinking, I went back to his place and let him fuck me six ways from Sunday. It was a hot experience; he had excellent control and was able to keep edging himself inside me until I was ready to cum, then we blew our loads together. 

Unfortunately, the next morning, he made it clear that he’s not a “relationship” kind of guy, but he gave me his number, and we’ve gone out on a bunch of dates, always ending up at his place with amazing sex.

Since he’s the only one of my friends who loves science fiction, I called him up to see if he was interested in going out to see the new Jurassic Park movie with me. He apparently had already seen it with his roommate, Andy, but he loved it so much that he said he’d see it again with me.

In the theater, he seemed like he was in heat. Not so subtly kissing me, letting his hand slide up my knee to my crotch, groping my dick through my shorts, all during the previews. I had to fight him off once the movie started so I could pay attention. Which was hard, since I was hard. I hadn’t jerked off the last two nights since I knew we had plans tonight; I expected to have sex with him, which was proving to be a mistake because two thirds of the way through the movie Jeff Goldblum had a scene where he was posed so provocative that I wanted to take Morgan to the bathroom and let him fuck me against the stall wall. I’m a good boy, though, so I kept it in my pants.

“Oh man, that was amazing!” I couldn’t hold back how impressed I was by the film as we walked from the theater towards his apartment.

“Totally! I told you it was going to blow your mind!” He matched my excitement.

“Everyone was saying it was great, but…damn, I’m honestly having trouble believing there isn’t an Island with real-life dinosaurs on it and Spielberg just filmed some sort of documentary,” I laughed.

“Want to grab a drink?” He pointed to a pub with obviously gay guys standing outside having a smoke. 

“Yeah, okay,” I grabbed the door handle and let him in.

We spent the next two hours discussing the nuances of the film while having a few drinks. Around midnight, I noticed he was doing less talking and more staring as I talked, with his hand rubbing so far up my thigh he could play with the elastic leg hole of my briefs.

I cocked my head to the side, “Want to get out of here?”

He smiled and nodded, reaching into his pocket for cash and handing it to the bartender without even asking how much we owed.

We walked a few blocks closer to his place, passing by an adult video store, and then at the end of the block, he spun on his heels, “Oh, wait, I need more lube.” He grabbed my hand and pulled me towards the door of the store.

I rarely go into these places, only when dragged by my friends. Morgan seemed to be very familiar with the store’s inventory and the clerk. Just pointing at the things he wanted, “The lube, oh, and those poppers,” he said, then glanced at me. We’ve never done poppers together, but I tried them twice with two different guys. I liked it with one guy, the other guy had a bottle that gave me a headache, and the sex was also bad, so I just grinned at Morgan, letting him know I’ll do whatever he wants to do. “Condoms?” The clerk asked, reaching for a pack he seemed to know Morgan used. “I’m still working on the large box you sold me last time,” Morgan laughed, pulling out cash and handing it to the man.

We took the little brown bag back to Morgan’s apartment, a two-bedroom on the fourth floor of a walkup that he’s been sharing with a college friend, Andy, since they were in their second year.

Even though it was after midnight, Andy was still up, on the couch, watching a horror movie he rented from Blockbuster. He paused it and grinned at me, “Oh, hey Miles, how was the movie?”

“Oh my God, it was so good!”

Morgan wrapped his arms around my waist, almost picking me up off the ground as he grind his crotch into my ass, making me stumble towards his bedroom. “Yeah, and now we’re tired and,” he faked a yawn, “ready for bed.” He hugged me tighter, making me chuckle. I waved bye to Andy, and we stumbled into Morgan’s room.

He wasted no time in getting us undressed and onto the bed. He was rock hard and humping into me dry, his 6.5” of cut meat was leaking precum between my cheeks as I wrapped my arms and legs around him as we kissed. He sucked on my neck, leaving a hickey even though I told him not to every time, and yet he does it anyway. I don’t stop him because it feels so good as he rocks his hips back and forth, his cock sliding up and down my crack over my hole and his lips on my neck, gently sucking harder and harder until the seal breaks.

After marking me, he sat up, leaning over to the nightstand and grabbing the brown paper bag, which he dumped onto the bed. He handed me the poppers to open as he opened the lube. I took a quick hit of the fresh poppers and let that rush wash over me as I felt Morgan pouring a generous amount of the lube on that spot just below my balls and then using his finger to catch the drips and rub it into my hole, then onto his cock.

He leaned back over me and started kissing me again, his lubed cock running up and down my lubed crack this time, it’s even more tantalizing with the lube, a teasing game we’ve played since our first hookup. 

He’s been having sex since the early 80s, so he learned before the AIDs crisis, and just like most men his age or older, you have to remind them to use a condom even though we all know better. I’m only a few years younger than he is, but I didn’t start having sex until I went to college here in the city, and by that point, everyone knew better than to go raw. “Mmm,” but fuck, when he teases my hole like that, it does put ideas in my head. “Get a condom,” I told him as I felt my hole try to open up for his head to pop in.

He kissed me again, then leaned over to the top drawer of the nightstand where he keeps his rubbers, his cock still planted between my ass cheeks as he stretched his torso to make that reach. “Fuck,” he shuffled things around before slamming the drawer shut. “I thought I had more,” he held up the empty condom box, then reached over to the other side of the bed to that night stand, shuffling things around, and then closing the drawer. “Do you have one?” He looked at me desperately. I shook my head no. “Fuck,” he grumbled, his sexual frustration matched by my own, running his hands up my naked thighs, his cock still lodged against my hole, the head pulsing as he leaned over me, holding himself up on his fists. 

“What about Andy? Can you borrow one from him?” I asked. 

I saw it click in his head, and he hopped up, his dick swinging in the air, “Yes, he never gets laid, he’ll have some.” He grinned at me, going for the doorknob. 

“Clothes?” I asked. 

He shrugged, “Andy’s seen it,” and was out the door, completely naked and hard as a rock.

A few minutes later, Morgan came back in, his cock surprisingly still semi-hard, unlike mine. He closed the door and hopped back on the bed, between my legs. “Any luck?” I asked. He opened his palm to show a condom package that was shaped more rectangular than square. “It looks beat up,” I joked. 

Morgan huffed, “Yeah, it was in the back of Andy’s desk drawer for…God knows how long. I can’t remember the last time that guy got laid. He said it’s his only one, so I had to make it worth it.” Morgan waggled his eyebrows at me, then tore the wrapper open, and the rubber snaked out. He stroked his dick a few times, bringing it to full strength, and then rolled it down his shaft. “Tight,” he chuckled, trying to stretch the latex at the tip to give room for his cum, then grabbed the lube to slick it up.

He added lube and started hunting for my hole with the covered cock. He put both my legs on his shoulders, then adjusted his positioning and found my hole, popping the head in. I hissed and breathed, gripping his thigh to hold him off as I adjusted to his girth. He pushed in a little deeper, then leaned over me and kissed me as I groaned, trying to relax my hole enough to take his cock. He slipped his tongue into my mouth as he slipped another inch into me, and I wrapped my arms around his neck, feeling his back muscles as he held himself up by his arms. He broke the kiss and rocked his hips again, sinking another inch into my ass, then held it there. He leaned down and kissed my nose, groaning out a breathy, “You’re so tight, baby.” I nodded, still trying to relax. “Use the poppers, it helps,” He smiled.

I had forgotten about the poppers and felt around the bed for the little brown bottle, then cracked it open and huffed. I let him take a hit as I felt the rush wash over me. As the rush hit him, he let his torso drop onto mine and started kissing me sensually, running his fingers through my hair, his tongue dancing with mine. I never felt so connected to a guy. I wrapped my legs around his back and let my hands drift down his shoulder blades as I felt his every breath and every muscle flexing as he started to rock his hips and inch his cock in and out of my tight hole.

I could feel myself relaxing, the pain subsiding and quickly being replaced with that feeling I love, the pressure on my prostate, the fullness of a cock inside me. “Mmmm, that feels good,” I moaned into his mouth, causing him to hunch up into me, his cock hitting a new depth, and I moaned again.

He dug his knees into the mattress for leverage and started deep thrusting up into my ass for a few minutes before my hole really opened for him, and then he ramped up to full-on fucking. “I love this ass,” he mumbled in my ear, holding my shoulders tight as he thrust deeper into me, while I struggled to breathe as I was folded in half. I held on tighter to him, flexing my ass around him as he bottomed out and then relaxing as he pulled back out. All I could do was moan with each reentry.

I took another hit of the poppers and passed the bottle to him. He propped himself up on his elbows as he inhaled. The rush made me so hungry for his cock to start pumping inside me again as I waited impatiently for him to cap the bottle and start digging his dick deeper.

He put the bottle down and groaned as he exhaled and felt my hole flexing around his dick. He leaned his head down on mine, our foreheads touching. Then kissed me on the lips as he gave me a few more thrusts before adjusting his position to let my legs fall to his sides, as he gently bit my left trap and began thrusting with more force. He only managed three pumps like that before we both felt the condom snap. It wasn’t the first time for either of us to have a broken condom. “Mmm…fuck,” he groaned, getting an extra stroke before stopping his thrusting balls deep. 

I unwrapped my arms and legs to allow him to pull out. I watched as he sat up and slowly pulled out the condom, wrapped around the base of his shaft. He struggled to pull the lubed-up, tight condom off his cock, it unrolled in reverse before he pulled it clean from his dick and set it on the bed. His chest rising and falling as he took a few deep breaths and smiled a half-hearted smile. “That was the last condom in the place,” he shrugged.

I groaned and started slowly stroking my dick. I was insanely horny, but we both know the rules. He adjusted himself between my legs so his balls were brushing against mine and started stroking his dick. I followed and started stroking, watching his muscles flex as he stroked. We were both determined to get off.

With my legs draped over his thighs, he rubbed my thigh with his left hand as he stroked himself with his right. His eyes darted from my hand stroking my dick to my eyes, then down to his dick and back up. Our quiet grunts as we pleasured ourselves were accented by the screams from the TV in the living room, but we didn’t care.

Morgan grabbed the lube and added more to his dick, then offered me a squirt before closing the cap. I nodded yes, and he held the tip to my tip and squeezed, a gush of lube came out, coating my dick and dripping down my balls. He tried to catch it with his finger and rubbed it over my hole, and I moaned quietly. He grinned, stroking his dick and rubbing my hole with his finger. I started stroking my lube-drenched cock as he played with my hole for a minute before he pushed his dick below my balls and let the head circle my pucker, and I inhaled sharply. The teasing was overwhelming. I looked into his eyes, and the glint of pure mischief as he continued to tease my hole was so hot.

I relaxed my hole and let my pucker kiss the tip of his cock as I stroked my dick. We both moaned as the teasing continued. He stopped for a second to hit the poppers and passed them to me. He was right back, teasing my hole with his dick as I hit the poppers. The rush hit me harder, and I relaxed into the mattress. Morgan continued pleasuring himself between my legs, using the soft, lubed skin of my pucker to stimulate his glans until my hole opened to the small amount of pressure he was giving, and the head popped into my pucker.

“Mmmm, fuck,” I moaned, my head clouded by sex and poppers.

“Oh fuck,” he inhaled sharply, holding at just the tip. His eyes latched onto mine, desperately seeking permission to push in.

I was so horny, the only thing I could do was nod ever so slightly and whisper, “just…don’t cum inside me,” and he leaned over me to kiss me. Moaning into my mouth, gripping my shoulders as he slowly pushed his raw cock into my guts. 

“Oh fuck, that feels so good,” he grunted in my mouth and immediately started thrusting into me like a virgin on prom night. His cock was so silky inside me. The lack of friction was so intense with each thrust that I couldn’t help but clamp my ass down, trying to hold his cock inside me. It only turned him on more, and his cock was suddenly more rigid, and thicker than it had ever been, and he was panting in my ear with each thrust. Mumbling, “that feels so good,” over and over again. I was so turned on by how turned on he was, and how great he felt inside me, I had to hold back my moans so Andy couldn’t hear me in the living room. I stroked myself faster, my entire body was getting so much pleasure as my hips rocked up to meet his thrusts and get as much of his raw dick in me as possible. I wasn’t going to last long.

Morgan kept pulling out, and I expected him to cum, but he’d just hold my legs pinned at the knees and spread around his arms as his dick sat at the edge of my hole, pulsing and threatening to explode but then he’d take a few deep breaths and relax a little so he could continue fucking me raw. I was in heaven, and he was in another world of bliss.

It didn’t take long before the edging session became too much for me, and on about the third attempt to hold off from cumming, when he pushed into my hole to resume fucking it pushed me over the edge. I couldn’t even warn him that I was going to cum, I just clamped down on his raw dick with my hole, and it pushed on my prostate, igniting the most amazing orgasm of my life. I pumped a half dozen massive shots of cum onto my chest, the first hitting my chin and the rest pooling between my chest and groin. My ass clamping on him sent him over the edge. He gave me a few last, desperate thrusts, taking in every ounce of raw pleasure before he pulled out at the last second, exploding all over my balls handsfree with a grunt for the first few spurts. Then he dropped my leg and grabbed his dick, pumping it as the next few shots pumped out onto my hole, eventually squeezing out the last few drops on my spent cock.

The shock of what we had just done settled in pretty quickly. “Umm…I’ve never done that before,” I confessed.

He huffed, “It’s been a long time since a guy let me fuck him without a condom on and holy shit…that was amazing.” His grin lit up his entire face as he leaned in to kiss me. Then we cleaned up the cum and went to sleep naked in each other's arms.