Chris - Drunk Hotel Sex

I ended up transferring to NYC for my Junior year of college. NYC was perfect for me; I was so busy, I had almost no time for relationships, and frankly, I was still very confused about my sexuality, so the more I could put off sex of any kind, the better. When classes started back up, I jumped into the first heterosexual relationship that presented itself.

The thing about me, at this point, I had gone back and forth several times thinking I was straight, then I’d have mind-blowing sex with a guy and think I was gay, and then back with women thinking guys were...not for me. This pendulum swing of sexuality was a nightmare; it would’ve been so great just to be able to admit at this point, “I’m gay” or “I’m straight.” That was not the case, though. I didn’t understand that you could be bisexual with romantic feelings towards a single-sex.

So here I am, single in the gay mecca of the world. My new friends are all from my filmmaking courses, and surprisingly (to the best of my knowledge), they are all straight. So that made it easier for me not to be tempted and make risky decisions...again, that is until we finished our first projects for the semester and decided to go out for drinks to celebrate. Karaoke and margaritas, I’m pretty sure, bring out the queer in everyone.

Somewhere around 2:00 a.m. or maybe even closer to 3:00 a.m., I found myself drunk and on the subway back to the apartment I shared with one of my classmates in Brooklyn. The train is mostly empty at this time of day, and because of that, it runs “local.” This means there are no express trains to get you to Brooklyn faster. You’ll hit every single stop on the line, and it takes at least an hour to get to my place.

I put my headphones in and closed my eyes. I listened to a song or two and then jolted awake, realizing I had fallen asleep. Luckily, I only fell asleep for the stops that the train usually skipped over, and I was about four quick stops from where I get off.

In a drunken haze, I looked around. There was a couple on the train practically sleeping on each other while sharing earbuds to listen to music. Across from me is an older gentleman who is eating some late-night McDonald's. On the other end of the bench is a guy who looks Egyptian or maybe Mexican—I'm not really sure—but he’s smiling at me.

At first, I thought he was smiling at someone near me, but I’m the only person on this side of the train car. So I smiled back and, in my drunken stupor, gave him the “what’s up” nod. This prompted him to come sit right next to me and, in a quiet voice, with a bit of an accent, he said, " What’s up?”

Grinning like a fool, I said, “On my way home.”

“Me too,” he almost giggled through stoned, slitted eyes.

He was clearly checking me out; I was horny and feeling bold, “I’d invite you to join me...but my roommate is home,” I whispered, with all the implications that come with that phrase. I’m not usually this bold, but I’m drunk, horny, and there are only a few stops for me to try and see where this is going.

It was clear at this point we both wanted the same thing.

“Yeah, my roommates are home,” he said, his accent thicker and definitely Spanish.

I looked around the train, “damn, too bad,” I said, looking at the digital readout, knowing I was off the train in two stops.

“You…,” his eyes looked down at my crotch, then back up at mine quickly, “you know,” he asked, not so subtly.

“Yeah,” I grinned, then quickly pursed my lips together and shrugged, “Too bad neither of us have a place.”

The train stopped again, the doors opened, and no one got on or off.

“What stop?” he asked; his English is not great, I’m realizing, and he's pretty drunk or high.

“Next stop,” I told him. “But my roommate is home,” I tried to make it clear, trying hard not to slur my words.

“I’ll get off with you,” he smiled a sexy smile.

I let out a chuckle, “ok, but I don’t have anywhere for us to...you know.”

“I have,” was all he said.

My heart started to beat fast. Was I going to hook up with this guy? He didn’t seem dangerous. He couldn’t be taller than 5’8” and maybe weighed 130 lbs. I’m only 5’7” and weigh about the same, so I could take him if things got weird. The train pulled up to my stop. We got out and said nothing as we walked out of the station into the dark night.

The air was crisp; it was the beginning of Fall. I stopped walking about a block from the station.

“You have a place?” I asked.

He looked around, “follow,” he said.

I followed him in the direction away from my apartment building. I never go this way, so I just follow along, recognizing nothing around me. After about five blocks, he stopped outside a house.

“Wait here,” he said, leaving me on the street; he went into the house.

About five minutes later, he came back out, grinning at me, and started walking. We walked for at least another eight blocks before we came upon a trashy-looking motel just outside the Brooklyn Queens Expressway.

“Wait here,” he said, then walked into the office.

Was I really going to hook up with a stranger at a trashy motel like a prostitute? A few minutes later, he came out with a key on a keychain; it was that skeezy of a motel. I followed him to a room about two doors down. He unlocked it, and we went in quietly. He locked all the locks and put the key down on the dresser.

I was incredibly nervous at this point, my heart pounding in my chest. He grabbed my hand, pulled me over to the bed, and then kissed me. He was suddenly so confident and suave that it calmed my nerves as we started making out. He pulled my jacket off and then my shirt, pushing me backward onto the bed. His kissing was so sensual, and he tasted and smelled so good that I was really getting into it quickly.

In the next room, you could hear a woman getting pounded by a guy. Either the walls were thin, or she was getting railed.

We broke our kiss. I kicked off my shoes, and he took off his shirt, revealing a skinny but trim body with decent pecs that were ornamented with dime-sized nipples. He immediately went for his belt; his pants slid right off his slender hips as soon as the belt was loose. He stood in his red boxer-briefs as he nearly tripped, taking his shoes off after his jeans. I couldn’t help but laugh as I watched. Then I pulled at my jeans button and the zipper, sliding my jeans off and setting them on the end table, not the dirty carpet.

He got on the bed between my legs and kissed me again. Then he smiled, looking into my eyes, his hard dick pressing against mine.

“I’m Chris,” I said bashfully.

“Lincoln,” he said, then kissed me again, his tongue licking mine.

We made out like that for a few minutes, exploring each other's bodies. I pulled down his boxer-briefs, and his hard dick smacked his lower abs with a thwack. He yanked my black briefs down, getting one leg free and leaving them to dangle on the ankle of the other, then returned to kissing me. Now his hard dick was rubbing mine, our precum leaking onto the other cock. His was about 7” uncut, with a torpedo shape, a smaller head with a thicker shaft that gets more narrower at the base.

He broke our kiss and rolled onto his back, I leaned in to kiss him, but he grabbed my head and diverted me to his dick.

“Suck,” he said with his sexy accent.

Oral is not really my thing, but the margaritas I had coursing through my veins had taken over, and without hesitation, I was licking his dick like a popsicle. He moaned and rubbed his fingers through my hair, guiding my mouth onto his dick and slowly pushing my head down until the velvety cock head hit the back of my throat. I gagged a little but tried to relax my throat and let my new friend's dick enter as I started to bob up and down.

Lincoln moaned and started to thrust up into my mouth, enjoying my newfound oral skills. I opened my eyes to look at his golden brown body, flexing under the pleasure I was giving him.

“Mmm,” I slurped on his dick, still gagging as I got more inches into my throat, but I felt determined. I pulled off his dick, “you like that?”

“I like,” he smiled. Then he sat up quickly, hopping off the bed to find his pants, and pulled out some lube and a condom. Not saying anything, he pushed me onto my back, quickly finding his place between my legs. His tiny bottle of to-go-lube squirted onto my hole, then his dick. He rubbed his dick with his left hand and my hole with his right.

“It’s been a while, be gentle,” I warned him as I stroked my dick to full hardness.

“Yes, yes,” he said, rolling the condom onto his hard dick.

He put my legs on his shoulders and smiled at me. Holding his dick with his right hand, he felt for my hole with his left, then pressed the head against it.

“Gentle,” I warned very seriously.

He pushed on my hole gently, with no give from my tight ring.

“Tight,” he said with a mischievous grin.

“Yeah,” I said, trying to relax.

He pushed harder, then a little harder, until the head popped in with a sting that hurt like hell.

“Oh shiiiit,” I yelped and tried to push him away.

“Shhh...shhh,” he said.

“Ow, shit, dude, no...wait,” I said, my dick going limp as the sting crawled up inside my body, leaving no signs of pleasure. “Dude...fuck…” I said, unable to breathe, “Wait a second,” I felt him push a little deeper still.

“Shh...shh, It’s ok,” he told me, then pushed a little deeper.

The pain turned into a searing hot pain, “Oh fuck dude, wait, I’m not ready,” I told him, almost shouting.

The woman next door was still taking a pounding, “thud, thud, thud,” against the same wall our bed was on. “Ungh, yes, baby,” she was moaning loudly as Lincoln ripped my ass open with his thick cock and searing pain.

Lincoln and I lay there, waiting for me to relax a little. He pulled all the way out and started to stroke himself.

“Rollover,” he said.

I flopped onto my stomach, and he quickly climbed on top of me and started to rub the head up and down my trench, finding my hole and pushing the tip back in.

“Oh fuck,” I said, gripping the comforter under me in my fists.

He didn’t stop; he just slowly pushed in every inch until he was all the way in. Then he lay flat on my back, “you like?” he asked.

I could barely breathe, “Fuck dude, give it a second,” I pleaded.

We lay there for a minute, then he hooked his arms under mine and grabbed my shoulders like he was going to use them to do pull-ups. He slowly pulled his hips back and then pushed all the way back in with a slight moan.

“Mmm, tight,” he said, then kissed my neck.

“Fuck, your dick is huge, man,” I groaned, pinned to the bed.

He kept his slow push-in and pull-out rhythm for a few minutes until he could tell I was no longer in pain. The stinging sensation had dulled, and I was feeling that full and pleasurable feeling I had missed for the last year.

“Fuuuuck,” I moaned as I raised my ass to meet his thrusting, finally enjoying it like I had in previous fucks.

He laughed in my ear, “you like my dick,” he told me.

He started to pick up the pace, sitting up on his knees so he could get a more forceful angle, riding my ass like it was a sex toy, his calves saddled up next to my hips as his ass rocked up and down, pushing his cock deeper with each thrust.

“Oh fuck,” I said, feeling him hit my prostate, my eyes rolling into the back of my head.

Lincoln started to sync his thrusting with the guy pounding the woman in the other room. I tried not to mimic her moans, trying to keep my masculine energy and my moans deeper as he pounded my ass in the best way possible.

“Fuck that feels good,” I said.

“Yes, you so tight,” he said, pushing deeper and harder.

There was a loud grunt from the room next door, the sound of a man having a prolonged orgasm along with her dramatic moaning.

“Mmm,” I moaned, “you getting close?” I asked.

“No,” Lincoln said, pulling out and rolling onto his back. “Ride,” he said.

I climbed onto his dick, impaling myself, getting his dick deeper than it had yet to go. I started to rock back and forth and jerk my dick back to full hardness again.

“Mmmm,” Lincoln moaned, holding my hips as I rode him.

“Fuck that feels good,” I said, his dick hitting my prostate like it was a nitrous button.

I felt my balls start to tighten, that familiar feeling that I was about to nut, “Oh fuck….I’m close,” I warned.

Lincoln held onto my hips and thrust up, I felt my ass tighten around his cock, and he thrust harder against my constricting muscles. He moaned and pulled me harder down onto his swelling cock, pushing me over the edge.

“Fuck…” I gasped, “I’m cumming…” I said, beating my dick faster and clamping my ass tighter on his thrusting cock and then slamming one final time down hard onto his lap. My cum shot out of my balls, out of my dick, and onto his chest.

“Mmmm….fuuuuck,” I moaned, coating him with rope after rope of my hot cum. My body twitching out the last few drops as Lincoln tried to thrust into me some more, but my ass wasn’t having it. He pulled the condom off and started to jerk himself off. I rolled onto my back as he furiously jerked off but then gave up with a laugh as his dick went limp.

“I’m too tired,” he confessed, defeated.

We got up, and he rinsed off in the shower. I used a washcloth to do a hooker bath before we got into the bed. He set an alarm to wake us up in 2 hours because checkout was in 3 hours already. I fell asleep quickly, with him cuddling me.

I feel like I only blinked my eyes when his alarm went off; he jumped for it to turn it off. The room was chilly; he jumped back into the bed and cuddled behind me again. I slowly started to wake up and realize I was naked in bed with the stranger I hooked up with last night, and his huge, very hard dick was pulsing between my ass cheeks. I was so tired, still a little drunk from last night, aka a few hours ago, and certainly wasn’t horny. I tried to ignore the dick; we didn’t have much time before we needed to check out anyway.

Lincoln kissed my neck and slowly humped up my ass crack. His dick felt so warm. He kissed my neck some more, running his hands up my chest and down to my limp dick. A moan escaped my mouth.

“Round two,” he said in a sultry voice as he nibbled my ear, rolling me onto my stomach as he slid on top of me. His knees spread my legs, and I instinctively gave him the room he needed to slip his dick between my ass cheeks and rub the head on my hole. He didn’t hesitate, using spit for lube, he was hard, and the tip of his dick was seeking my hole and found it in no time.

His dick hooked the head on my hole, which is still sore from the attempted sex a few hours ago, but as he continued to touch me and turn me on, my hole quickly became more willing to let him in. He felt it and pushed the head in.

“Ah…” I gasped, wincing.

“It’s ok,” he paused, sitting up and adding more spit and then putting more pressure on my hole.

The first inch popped in.

“Oh shit,” I groaned, not the painful sting like before, but discomfort for sure.

The snoozed alarm went off again. Without pulling out, he leaned and snoozed it again, giving us 9 minutes before it would go off again. Before his arm made it back from the alarm clock, his hips were pushing in, adding more pressure now, a few inches go into my tight hole.

“Mmm…si,” Lincoln moaned, slipping into Spanish as he bottomed out.

I spread my legs wider to give him more access as he started to pump up into my ass gently.

“Fuck, that feels good,” I whispered into the pillow. My eyes still closed, I tried to focus on the pleasure. It felt so much better than last night. “That feels so good, man,” I groaned, muffled by the deflated pillow.

“Yes, you like my dick,” he said matter of factly, out of breath as he was picking up the pace.

That’s when it hit me: did this feel different because he was in me bare?

“Do you have a condom on,” I asked.

“No, no condom,” he said, his muscles flexing as he continued thrusting and picking up the pace.

The alarm went off again; again, he leaned over and snoozed it. He started to thrust harder and deeper now, holding me tightly so he could get as deep into me as possible.

“Just don’t cum in me, man,” I managed to say between moans, enjoying his body on mine; his cock felt so good inside me.

“Yes, yes, cum in you,” he said, thrusting harder and moaning.

“Ungh…no, no cum inside,” I tried to communicate through the pleasure as his head pegged my prostate, my ass opening more for his invading raw dick. It felt so damn good.

“Si, ah si, Ungh mmmm, Si,” he grunted, thrusting fast and deep.

I felt his dick swell, his grip on my shoulders pulled me tight into him, and his thrusting changed to short hard thrusts as he unloaded in my hole.

“Si, ungh...si,” he moaned again, collapsing on my back.

“Oh fuck,” I said, catching my breath, feeling my hole twitching around his softening cock. The wetness inside me soothed the sore stretched anal walls in the best way possible.

My brain was confused with all the panic of this guy nutting inside me, the pleasure of a guy breeding me, the slight headache from last night's shenanigans settling in, and just general tiredness. He slowly pulled out with a grunt and rolled off of me.

“Your ass is good,” he told me, catching his breath, running his fingers up and down my spine to my ass.

I rolled onto my back, looking at his softening, glistening dick, which still looked big. I took a moment of pride, knowing I was able to handle his cock like a man. Then, looking into his eyes, his smile set my mind at ease. We lay there in bliss for no more than a minute before the alarm went off again.

“Time to go?” I asked.

“Yes,” he said, sitting up to grab his boxer-briefs.

We dressed in silence, as quickly as possible, before the room phone rang to let us know it was time to check out.

Before we went our separate ways, we exchanged numbers. I went home and slept for the next couple of hours before I had to get up to meet my friends for a strategy session for our next project. There was no way I would be at my best…worth it.