Craigslist Chronicles Ch. 04: Alex

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Kas 20, 2022 // By:analsex // No Comment

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Hey All, continuing my series based around my early 20’s… Thought I’d get it all written out before I hit my 30’s. 😉 Most of the chronicles I’ll be releasing are based on real-life experience as I explored my sexual urges with other men. Again, feedback on writing is enjoyed! I love some constructive criticism.

I think about this night quite a bit. It was literally one of the most fabulous nights of my life.


Craigslist Chronicles Ch. 04: Alex

It’s been a few weeks since Alex, and I last hooked up. We’ve been keeping in touch regularly via text, but his schedule has been busy the last few weeks. Thankfully, we both had the next few days off, and both had some free time.

We’ve been planning this overnight trip that both of us were extremely excited about. A few weeks ago, while at a conference for work, I got a free night’s stay at any of their establishments because they messed up on our rooms. I decided to share this free night I’ve been saving with Alex. It’s a fancy hotel so that it will be pretty damn sweet.

In the mid-afternoon, I shot him a text asking where he’d want to meet, or if he wanted me to pick him up. He thought just picking him up would be easier. His place was on the way to the hotel, so it worked well. After picking him up, we stopped and had a quick bite to eat at a local deli. Once we finished eating, we stopped by a convenience store and picked up a few mixers. Alex had snagged a bottle of Jack Daniels from his dad’s collection for us.

With our bags in hand, we started to walk into the lobby. As I checked us in, I couldn’t help but notice the hotel clerk giving us a quick stare of judgment. After passing us our keys, we started heading towards the elevator.

“Pretty nice place” Alex stated.

“Yeah, it is,” I replied as I gave him the rest of the story on how I got the room.

We got a room on the 14th floor, just two levels below the penthouse. It’s definitely going to be a pretty sweet suite I thought. As we entered the room, my assumptions were right. The room was damn awesome. A decently sized entry that leads down to the large central room that rocked a pretty killer looking king sized bed. There was a second room that looked like a living room, and the bathroom was twice the size of mine at home. It had two sinks, a substantial two-person bathtub, and a giant glass-walled walk-in shower.

After unpacking our things, I came a little more prepared this time, bring a box of condoms and a large tube of lube. As we continued to explore the room, I grabbed the glasses near the kitchenette and poured us both a shot of whiskey.

“To a night of fun with no one around” Alex toasted.

“Fuck yeah,” I said as I tapped his glass with mine.

After the shot, we poured a bit more into our glasses and made our way to the couch and continued to talk. We chatted about the excuses we told people on what we were doing tonight and how much we were looking forward to having some uninterrupted fun.

The more we drank, the hornier we got. Sitting close on the couch, moved closer to each other, lips slowly moving closer. As our lips touched, we began furiously making out on the sofa removing each other’s clothing. With our shirts off, our hands started exploring each other’s body.

Moving off the couch, my hands drifted towards his belt and his mine. As our pants fell to the floor, our cocks touched, shafts meeting, thrusting into each other, exciting each more and more.

As our cocks grew closer, so did our tongues. Lips were smashing together; light scruff rubbed as our faces pressed together. Reaching towards our cocks, I held them closer together as they grew in unison.

Removing my tongue from his mouth, I slowly started kneeling, gazing upon his hard cock. Taking him into my mouth, I swirled my tongue around his head.

“Damn do you do amazing things with your tongue” Alex stated as I added more suction to the mix.

As his cock reached full stiffness, he pulled me up, darting towards my lips. His cock flat against my stomach, gyrating it as we kissed. We started moving towards the bed. As the back of his legs hit the bed, I slowly leaned him back further. Straddling on top of him, we slid into the center of the bed, ravaging each other.

Our cocks head to head, rubbing up against each other’s lengths, my hands explored his body. Reaching for the side of the bed, Alex grabbed a condom and lube from the nightstand.

As he removed the condom from its wrapper, I could help but stroke hole against the head of his hard cock. With the bear condom now in hand, I moved my mouth towards it.

“Let me try something…” as I said as I took the condom into my mouth. One of my old girlfriends and to do this all the time. She used to slowly slide the condom on my cock using her lips along with some subtle teeth. I thought I’d give it a go…

“Let’s see it,” Alex said, imagining what I was going to do next.

Moving down the bed, my head hovered over Alex’s cock. Using my tongue, Ankara escort I rolled the condom around in my mouth, adjusting it, so the tip was around my tongue and the base of the latex along the backside of my front teeth.

As I slowly wrapped my lips around his cock, I guided his head with my teeth, slowly unraveling the condom over the head of his cock. Opening my mouth wider, I continued to engulf his hard shaft, my teeth slowly rubbing down his length.

“Oh, My, God” Alex moaned as I nearly reached the base of his cock. “Where the fuck did you learn that?”

“Old Girlfriend,” I said as I removed his hard cock from my mouth. “She did it a few times to me, and I fucking loved it. Thought I’d share the wealth.” I said laughing as I lubed his cock up.

Crawling up on top of him once more, I slowly aligned my ass with his hard cock. Reaching down to kiss him, he steadily thrust into me, my ass stretching to accommodate him. As he entered, I bit his lip releasing a moan of delight.

“Fuck, you feel so God, damn, good,” I moaned, biting Alex’s lip harder while lowering myself onto his cock further.

The more furiously we made out, the harder he thrust into me. Our beards were scratching together like sandpaper, my dick slapping against his abs.

Changing positions, he pushed me back, pulling himself out.

I moved towards the head of the bed on my knees, gripping the headboard. Getting up behind me, Alex grabbed my hips and thrust deep into me. With my back arching, I held the headboard tight. His balls were slapping hard against my ass. Looking back at him, he had just a focused gaze.

As he thrust harder and deeper into me, the headboard slammed against the wall, knocking with every blow.

As his grip strengthen, my cries grew louder, “Oh fuck Alex! God you feel good! Harder!”

“Fuuuck! I’m Cumming!” Alex shouted as he shot his load deep into me.

Removing the condom, he dropped it to the floor. Releasing my grip on the headboard, I made my way back down onto the bed. Alex, cuddling into me with his warm wet cock in between my legs.

After a few minutes of watching TV, I could feel his cock hardening between my thighs. Quenching my legs around his cock, I lightly began rolling my thighs around his cock. As he grew, I turned my head towards him. As our lips met once again, I turned in to him; our cocks dancing. Reaching down, I held our cocks tight together, running my hand up and down our shafts.

As our tongues twirled around, he reached for the nightstand again, pulling out another condom. Letting go of my lips, he guided me towards my stomach, laying me flat on the bed. Straddling me at my thighs, his hands spread my ass, his cock, teasing my entrance.

He began entering just the tip of his cock, only to withdraw it quickly, stretching and playing with my asshole.

Each time he poked his head into he, I couldn’t head but let out a loud moan of pleasure. “Oh, oh, oh fuck. Stop teasing me god-damn-it!”

Without another word, he dug his cock deep into me. My back was arching up, arms pushing me off the bed. As he thrust into me, my ass clenched his cock as it drove into me.

Pushing my head into the pillow in front of me, moaning loudly could hear the bed knocking against the wall once again.

“Keep clenching my cock!” roared Alex as he continued plowing into me, shaking the bed violently against the wall. “God you feel amazing!”

“Oh fuck, oh fuck, oh Fuck,” was all I could get out between thrusts.

Wrapping his hands around me, he pulled me into him with one last thrust. As we slowly fell towards the bed, I could feel his cock spasming within me. Hugging me tighter, he laid on top of me, holding me close; kissing the lobes of my ear.

Slowly withdrawing himself from me, he rolled to my side, turning towards me. Grabbing my ass, he pulled my cock closer towards his abdomen, thrusting into my cock. As his tongue explored my mouth, my cock enjoying the sliding. My cock, sliding against the hair of his stomach, spasmed and let out squirts of cum, all over both his and my abdomen.

Quickly cleaning myself up, Alex jumped up off the bed reaching for the bottle of Jack Daniels. He poured another shot in each of our glasses. Handing me mine, “To a long night, of much more fun,” Alex stated.

“Much more!” I said as I clanked his glass.

“How about a breather?” Alex asked as reached for and broke the plastic cups out of their plastic wrapping sitting on the table.

“Sure, I could use some fresh air,” I said.

“How about we take a drink to go,” Alex said as he poured a few shots into each of the plastic cups.

“Sounds even better” I replied.

Grabbing our sweatpants up from off the floor, I tossed Alex’s his. After we put our shirts and shoes on, we topped off our glasses with some coke.

I could still feel the cum on my abdomen sticking to my sweatshirt as we made our way to the elevator.

With both of us leaning up against the elevator wall, I quickly Ankara escort bayan looked into his eyes as the elevator door closed. Bring our lips in; we made out as we descended to the lobby. As we came to a stop, I quickly grabbed Alex’s cock through his sweatpants and gave him a decent squeeze as I bit his lip.

“Damn tonight was a good idea,” I whispered in his ear.

“Oh, I totally think so too,” Alex replied.

Making our way into the lobby, our surroundings were silent. The hotel clerk was sitting behind the desk playing what seemed to be a video game. As we walked through the sliding doors, the cool, crisp night’s air blew over us.

“Damn that feels good,” Alex said, sweat still dripping from his forehead.

“So, what all are you doing tomorrow?” I asked.

“Nothing too much,” Alex replied, “Probably just doing some housework, might go hang out with some friend’s tomorrow night.”

“Oh, that’s cool,” I replied, “Yeah, I have some housework to do too, but yeah, I’ll probably hit up some old friend’s tomorrow night too.”

“That’s cool,” Alex said as we made our way through the dimly lit parking lot. “So, earlier you said something about some previous girlfriends. You more in the closet right now?”

“Ha, yeah, I’m not really sure.” I awkwardly replied. “I don’t really know what I am looking for yet. I guess you can say I’m exploring, maybe closeted bi?”

“Yeah, I know what you mean,” Alex said, “I love girls and guys, not many people know about my bi side though.”

As we continued our conversation, we started to make our way back to the hotel, finishing our drinks.

Feeling quite a bit tipsier, we stumbled our way back into the hotel.

As the elevator door closed behind us, looking down at Alex, his sweatpants where bulging.

Quickly kneeling in front of him, I pulled down his waistband and watched his cock spring out.

“What the fuck…?” Alex asked as his dick grew harder.

“Just some quick fun…” I said as my mouth licked the top of his hardening cock.

“Oh, fuck” Alex moaned as he leaned against the wall, gripping the metal railing with one hand.

Grabbing the base of his cock with the other, Alex slapped his cock against my face a few times before guiding it back towards my welcoming mouth.

As the elevator rose, I continued swirling my tongue around Alex’s cock. Coming to a stop, I quickly pulled his dick out of my mouth and pulled his waistband up and over his now solid cock.

With his sweatpants bulging, the elevator door opened with both of us chuckling like school girls.

“Ha, that was kind of exhilarating,” Alex said as we opened the door back to our room.

“Yeah, it was,” I replied with a smirk on my face. “Might have to have a bit more fun outside our room later.”

“The night is still young…” Alex said as he grabbed my hand, pulling me close to him.

Pulling me tight against him, lips entangled, I pulled our pants down, Alex’s cock poking towards mine. Reaching for each other’s shirts, we promptly pulled them off, our lips attacking each other with each pass of clothing.

With Alex’s cock sticking into my abdomen, I knew it was time for another round. Breaking our kiss, I quickly ran to the nightstand, grabbing another condom and the tub of lube. Regaining our kiss, I unwrapped the condom and rolled it over his rigid cock. Grabbing the lube from my hand, Alex squirted some out and lathered up his cock as I turned against the entry wall. Dropping the lube to the floor, Alex’s hands grabbed mine, holding them over my head against the wall as he kissed my earlobes.

Lining his cock up against my hole, he slowly pressed in. Standing was a whole new sensation. Slowly pushing his whole body into mine, sliding his cock deep into me. With each thrust, biting and pulling my ear a little harder.

Loosening his grip, Alex slowly pulled out of me. Taking my hand, he pulled me towards the couch. Kneeling on the sofa, I gripped the back with my hands, sticking my ass out towards him. Grabbing my sides, his hand swirled around my skin as he straightened his cock to my hole once again.

Thrusting into me, the small couch rocked back and forth, hitting the floor with each thrust with a thud. With his hands gripping my side harder, he began thrusting in and out of me like a jackhammer. Letting out loud moans of ecstasy, my hand slipped off the back of the couch, hitting the light to the side of the sofa, knocking it over. With a crash, it hit the floor.

Quickly stopping, we checked to make sure nothing broke. Moving to the bed, I laid on my back. Alex was crawling towards me, pulled me down the bed, making my legs hang over. Lifting my legs up over his shoulders, his cock pushed back into me. Holding my legs tight to him, he started leaning towards me, cock reaching new depths.

The bed raddled, headboard slapping the side of the wall. Leaning even closer towards me, my legs began to buckle as he crawled onto the bed. Slowing his thrusts, he moved Escort Ankara his head towards me, lips meeting. As tongues danced, he rhythm steadied, more sensual like. Slowly thrusting his whole length into me, sucking my lower lip.

His cock still hard inside, came to a stop. “How about we try out that awesome shower,” Alex whispered into my ear.

“That sounds amazing,” I moaned, feeling his cock slide out of me.

Making our way towards the bathroom, Alex removed the condom that hugged tight against his cock, throwing on the floor by the others.

“Damn,” Alex said as he turned the handle; water falling from the ceiling and the wall. “This is pretty damn nice.”

“Wow,” I replied, “That’s for sure.”

As we entered the stall, warm water fell upon us. With our lips meeting, our hands reached for each other’s cocks, stroking as the water descended on us like tropic rain.

Turning me around, stomach now pushed against the chilled cold tile, Alex pressed his hard, raw, cock against my ass. My hole, still full of lube, began to open as Alex’s cock slid into me. God did his bare cock feel good.

Waves of pleasure shooting through me, I pushed myself deeper onto his cock; feeling his hard shaft flow through my hole.

“Oh fuck,” I moaned, “God you feel amazing…”

“Fuuuuck,” Alex moaned back, “damn you do too…”

Continuing to thrust deep into me, his cock hard as ever, my body experienced new waves of pleasure.

Nibbling on my ear once again, Alex plowed harder into me. “Oh, Gooood!” I wailed, feeling every square inch of him within me. Who would have thought such a thin piece of latex could dim the experience so much?

As his nibbles moved to my neck, his thrust became slow and controlled, pushing himself deep into me, focusing on his cock being gripped by my tight entrance.

“Fuuuuuck,” Alex moaned, thrusting deep into me with one last push. I could feel his cock spasm within me; shooting his warm load deep into me.

Tightening my ass around his cock, I milked him further. Slowly pulling himself out of me, I let out another quiver. Finishing up, we started rinsing each other off with a sensual touch.

Getting out of the shower, we dried off, and grabbed the bottle of now almost empty whiskey, and poured another two shots into each of our plastic glasses, emptying the bottle.

“How about another breather?” Alex asked as he reached for our sweatpants on the floor.

“Yeah, that sounds good,” I replied looking down at the clock which just flipped to 4:00 AM.

As we walked out of the room, my ass dripping a mixture of lube and cum, I threw on my hoodie and shot the remaining whiskey in my glass.

“Outside?” I asked as we walked towards the elevator.

“For a sec,” Alex replied with a smirk shooting his whiskey, “But I thought maybe we could have some fun outside of our room.”

“Oh, damn…” I replied, “I like your thinking.”

Making our way towards the stairwell, I could faintly hear the moans of a woman as we passed the line of hotel doors. Looking down towards Alex’s crotch, I could see his cock bulging from inside his sweatpants again.

Both somewhat drunk, we made our way into the stairwell. Looking around for cameras and listening to see if either of us could hear anyone, Alex pulled his cock out right there in the middle of the stairwell as the door closed behind us.

“Here?” I asked as I leaned in towards his cock.

“For a sec,” Alex said, “Until we hear something.”

Taking his cock into my mouth, my heart paced. God was it exhilarating.

As cock made his way down my throat, I swapped it deep, taking him to the base.

“Oh God,” he moaned as I softly cupped his dangling balls in my hand.

“Suddenly hearing a door open a floor or two down, I quickly withdrew his cock from my throat, while pronouncing a loudish gag in the process. Quickly pulling his pants back up, we went down a level and entered the floor below us looking for another stop to have a bit of fun in.

Making our way down the hall, we made a sharp left into the cubby where the ice and vending machines were. It was another longish L shaped hallway, with the ice machine down the first portion and the vending machines around the other. Walking towards the vending machines, Alex threw himself on me. Our lips meeting, tongues dancing.

Making out furiously, he pushed me against the vending machine.

“Fuck me here,” I moaned as our lips parted. “I’m still lubed up…”

Before I could finish, Alex started turning me around, pressing me against the glass wall of the vending machine pulling pants down, exposing my ass.

Rubbing his bulge against my ass, he lowered his sweatpants. His bare cock pressed against my cum filled hole. Lining his cock up, he plunged into me with one deep controlled thrust.

“Fuck!” I loudly moaned as he penetrated me from behind.

“Shhhhh,” He said as he grabbed my shoulders, thrusting faster.

My face up against the glass, back arching, the vending machine shook. God did his cock feel fantastic sliding in and out of me. I’m not sure if it was the mixture of lube and cum lining my ass, but the feeling of his head sliding deep into me rubbed my insides perfectly.

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