Craigslist Chronicles Ch. 03: Chuck

Craigslist Chronicles: Chuck

It's been a few days since my last hookup, as you can probably realize, I've been pretty damn horny. Alex is busy all week but will be free next week for a few days. (It'll be my weekend, so I'm pretty damn excited about that). But, back to the here and now... What can I say, the craving is hitting hard today.

During my lunch hour, I filtered through the hundreds of ads, looking for another chill dude to hang out with. I sent out a few messages and awaited my responses.

Nothing, as my shift was nearly at its end. I felt like a junkie needing his next fix... I thought maybe I'd just hit up the adult toy store and finally get something fun I could use whenever. As my shift ended, I finally got a reply from the following post:



Chill dude lookin for same!" - 22

Hey all, looking for a chill dude like myself to hang out with. I work a swing shift so anything after 12:30am works great. Have my own studio apartment. I'm 6' 160lbs, 8c, and completely ddf. Looking for another chill dude to relax with and smoke some 420. Fwb preferred!

Half white half black here.

I was psyched. Damn did this work out perfectly. From the pic he sent, he was a pretty cute black guy. Short curly black hair, with a somewhat innocent smile on his face. I guessed that he was pretty shy and/or closeted himself. As I sat in my car, we texted back-and-forth a bit, sure enough, he was. He also lived about 20 miles away. It was a bit far, but at this time of night, I'm not going to run into much traffic.

Once he sent me his address, I made my way towards him. Letting him know my eta was about 30 minutes, he promptly replied No worries, I should be getting home just a few minutes before you.

Took a little while to find some street parking, but once I did, I made my way towards his place. It was a pretty run down brick apartment complex right in the middle of the city. Walking into the entry, I began looking for his name on the buzzer.

After going through the long list, I finally came across his name. Chuck L.

Buzzing the number, I awaited an answer. The night was cold, somewhat foggy with the noise of the city loud behind me. Suddenly the door buzzed. I continued my way in, taking the stairwell to the 4th floor.

Exiting the stairwell, I saw him walking towards me wearing a tank top, gym shorts, and leather sandals. Reaching out to introduce myself in person, I firmly gripped his hand.

"Hey Man," I started, "Name's Evan. Good to meet ya in person."

"Good to meet you too," he replied as he guided me towards his door. "Name's Chuck."

He was pretty timid; we awkwardly talked for a bit as he showed me around his place. It was pretty small; I guess your average sized studio apartment. A small kitchen and dining room, and in lieu of a couch in the living room area sat a queen sized mattress on the floor.

As we sat down on the bed, he reached for the remote, starting an episode of family guy. He was pretty quiet, only talking a bit during the commercials. An awkward small talk I guess you can say.

With the episode wrapping up, I sat a bit closer to him. Moving my hand towards the prominent bolds in his gym shorts and his gym shorts, I glanced at him and smiled. Slowly rubbing the outline of his cock, it started to grow and twitch.

This was his first encounter with another guy. He was pretty unsure of what to do, so I kind of lead the way and he just went along with it. We just sat there, side by side, watching the next episode with my hand massaging his cock.

A few minutes later, he slowly leaned back into the bed, causing his shorts to tower high. I slowly pulled down his shorts, pulling his cock down, revealing it inch by inch. As the shorts passed the head of his cock, it sprang up.

He continued to kick off his shorts as I slowly leaned over him, guided my lips towards his cock. He must have just showered before I showed up. The smell of old spice filled my nostrils. His dark brown skin was nearly flawless. Pubes were trimmed and neat. With two hands I grasped his cock, pulling downwards as his head touched my lips. As my tongue swirled around him, a shiver ran through him.

As my lips and tongue moved around his cock, the stiffer it grew. Slowly moving guiding his cock out of my mouth, my eyes gazed over his body. His skin was as soft as silk.

His cock was a bit longer than any other's I've been with. It wasn't as girthy, but it had a gentle downward curve to it. His perfect mushroom head flowed nicely down his flawless shaft meeting his nicely trimmed curly black pubes.

His cock was incredibly perfect. Smooth with a pronounced head. I've wanted to try deep throating, and I think I may have just found the right guy to practice on. As I took his cock back into my mouth, my lips and tongue greeted his firm cock with a warm welcoming. Looking up at him, he smiled back at me.

As I slowly took more and more of him in my mouth, I subtly moved to the floor on my knees. His legs were my head. I continued to force my way down his length, going deeper than I have had in the past.

My untrained gag reflex wouldn't allow too much more as I started gagging. Looking back up at him, he slowly began guiding myself off his cock.

"How about this," he said, "Wanna smoke a bowl with me real quick?"

"Sure," I replied. "God, I haven't smoked in a few months. And fuck, have never had sex while high... This will be fun."

He grabbed my hand, pulling me off the floor, and guided me towards the bathroom. As we entered, he pulled out his bog from the linen closet. Pointing towards the switch for the exhaust fan, he told me to flip the switch as he loaded the bowl.

After two bowls... damn, I was pretty baked. I had a terrible time concentrating on anything unless I focused on it. The one thing I did not have to focus on, however, was my utter horniness that was ravaging my body. "Damn," I mumbled, "This shit is good."

Making our way back to the bed, an idea crossed my mind. A few days ago, I was watching this porno of these two guys throat fucking. One of the guys was laying on his back on a high bed, with his head hanging over the edge. The other guy had a perfectly aligned shot of digging his cock deep into the guy's mouth.

I told Chuck about my idea, and he quickly agreed it was something he wanted to try. His mattress was directly on the floor, so many instead of him standing, he would kneel, and it would work just as well.

Laying down on his bed, I positioned myself, so my head was hanging over the edge, just inches above the floor. Chuck got on his knees, his cock towering over my face giving me a great view of his well-hung balls.

Opening my mouth, he slowly entered me, pushing further and further until I felt the head of his cock snake its way back into my throat. Oh fuck, I was really doing it. The sensation was fantastic, the head of his cock warmly messaged the cotton ball like feeling I had in the back of my throat from being baked. I could feel every inch of him like I've never felt before. Every ridge, every vein. As he pushed deeper, my throat swelled to accommodate him. Bottoming out, his balls pushed against my face, pubes brushing against my bottom lip. I suddenly found with the ability to control my gag reflex completely.

He wasn't thrusting his cock, he just left it, deep in my throat. After a few seconds, he withdrew most of himself so that I could take a quick breath. Ready for more, reached my hands around the back of his waist, pushing him towards me. This time, he quickly drew his cock into me, balls slapping against my nose. He continued thrusting with strength and precision.

Placing his hands on my shoulders, his thrusts quickened. Gagging for air, my throat began to tighten around his shaft with each thrust, throat bulging, feeling a new and exciting sensation. His pubes were grinding against my lower lip, balls spanking against my nose & eyes. Not knowing where to cum, he quickly removed himself from my mouth then punctually began expelling streams of cum, covering both my face and shirt.

Moving my hand around my face collecting his warm cum, I took what I could into my mouth. His cum was sweet, with the slightest taste of grapefruit. Taking off my now cum stained shirt, his cock stood proudly in front my face, ready for more.

Quickly making my way towards my bag, I grabbed a condom and a tube of lube. As he rolled the condom on, I quickly made my way back to the bed on all fours, my ass in the air. Grasping the sheets in front of me, the length of his cock slowly moved over my ass. Feeling his cock slide in between my cheeks, up towards my back.

Sliding his cock back towards my hole, I felt him press against my tight entrance. Slowly he began pushing onwards. Being as high as I was, put my nerve endings on double duty. I could feel every square inch of his cock as he slowly slid into me, my anus stretching. His head moving deeper into me. The bulging veins of his shaft pushing through my entrance. I moved my focus closer to the feeling of his cock invading my ass.

Waves of electricity ran through me as he started thrusting. As his cock ran through me, it was similar to the cotton ball like feeling I had in the back of my throat. Stretching but soothing the walls of my interior. The feeling, still hard to describe, is something I look back to and remember to this day.

As his pace quickened, his balls began slapping against my ass as he bottomed out. His hands grasped the sides of my ass, which each thrust, pulling himself closer to me.

"Oh, my fucking gooood" I moaned. "Harder!"

His pelvis was slamming into my ass with force. I couldn't help but grasp the sheets harder, closing my eyes, submitting my complete focus on his cock tunneling through me. Taking each blow as if it was in slow motion.

Suddenly, I felt a whole new sensation plow within me. I could feel the bare head of his cock sliding deep into me. My wails of pleasure grew louder as I released a long drawn out "Fuuuuck."

"I'm comming!!" he moaned as I felt his cock spasm within me. A new gulf of warmth filled me as he let out a soft, "Oh shit..."

As slid his hard cock out of me, in slight laughter he stated, "I'm pretty sure the condom broke."

"That would explain the warmth," I replied with a grin on my face as I reached towards my ass, touching his hot cum dribble out of me.

My cock, so hard it hurt, pointed towards him as I got off the bed. While removing what was left of the condom, he knelt down in front of me, slowly taking the head of my cock into his mouth. His teeth were brushing my shaft as he engulfed me further.

I could fee his hand wandering towards my ass, swirling his finger around my cum flooded asshole. As he slid two fingers in, I pushed my cock deeper into his mouth. As the tips of his fingers explored my hole, he started pressing on my prostate, shooting a wave of pleasure through me.

"Oh fuuuck" I moaned as I plowed into his mouth releasing my load into his warm, welcoming mouth.

Both covered in sweat, we laid on the bed and continued watching some TV, Chuck's flaccid cock resting between my cheeks. His hand tucked to my side, slowly moving his fingers in a circular motion, making my skin tingle.

After the show ended, we got up off the bed and started re-dressing. Making our way to his dining room table, he grabbed a couple of cokes out of the fridge, and we spent the next hour talking, getting to know each other.

As our night ended, I made my way back to my car. I could still feel his cum dripping out of me.