Craigslist Chronicles Ch. 01: Beginnings

Craigslist Chronicles – Beginnings

I wouldn’t necessarily call myself gay. I do enjoy sleeping around with chicks. But, lately, I can’t really call myself straight either. I’ve been dealing with the urge to sleep with another guy. For the past few months, I’ve been exploring and getting off in the m4m section of craigslist. I love reading the posts, seeing dom tops with their big cocks knowing what they want. I kept putting myself in the shoes of the people that would reply to them, knowing that all these people are in my backyard. So close.

I couldn’t help but think about what it would be like sucking another guy off… or taking a cock up my ass for that matter. I begin browsing through these ads more and more often. Using my work breaks to see what new posts popped up and who’s close to me.

At 20 years old, I’m a pretty average guy. Some would say I have the most stable job out of all my friends. I make pretty decent money, bought a house a few months ago. I’ve got two roommates, but they pretty much keep to themselves. I haven’t had a long-term girlfriend in a few years, but I’ve hooked up with quite a few chicks. Lately, it’s been a little rough. I recently moved from a regular day shift to a swing shift, working from four in the evening to midnight Wednesday to Sunday. It’s a pretty sweet shift. It’s way more laid back and a lot of fun. But, as you can imagine, its put a hamper on my hang out time with friends.

It’s been a few months since my last hook up, and not sure why, but today primarily I’ve found myself incredibly horny. Work was rather slow, so my mind was occupied with everything but work. As I sat in the break room drinking some coffee, I continued to fuel my craigslist addiction. However, this time I focused on looking for someone I could meet up with.

I came across one ad that was posted earlier this morning….

— Netflix with me? — 20 M

Hey, looking for a chill guy to relax with and watch a movie or something. Must be discrete. Mainly top here if it gets that far. Athletic mixed with scruffy here. 170, 7.5″c, and all clean/ddf. Looking for a regular thing. Please be around my age!

As my break was nearing its end, I quickly started typing up a reply. I made my way to the bathroom to snap a quick pic I could send along with the message. I unbuttoned my shirt a bit and snapped a selfie in the mirror looking pretty dapper.

As I said, I’m a pretty average looking guy. At about 5 foot eight, I weigh in at about 160 pounds. With my short, messy styled brown hair, blue eyes, and 5 o’clock shadow, I looked pretty good. I hit up the gym pretty regularly, but still, have slight padding on my abdomen. In the downstairs apartment, I’m pretty average.

I quickly sent the message and a wave of I can’t believe I just did that traveled through me. As I continue my work, I couldn’t help bet check my phone every few minutes, anxiously waiting for a reply. Finally, a few hours later, I got a response.

Hey man, name’s Alex. I don’t get off work until about midnight tonight, but I’m feeling pretty horny. Would you want to meet up at my place? We’d have to be pretty discreet, I still live with my parents. We can pretend you’re a friend from work. What all are you into?

I quickly opened up the attachment he sent along with the message. Damn was he hot. He looked pretty athletic in the swim shorts and tank top he was wearing. I couldn’t help but notice the prominent bulge beneath his shorts.

Quickly hitting the reply button, excitement built up through me. It has to be fate I thought, crazy that he gets off work the same time I do. Not only that, but he was located in the same neighborhood as me. In my message I told him thanks for the reply and that I’d love to meet up tonight. As to what I’m into, I’m not sure. I’m incredibly interested doing something with another guy while taking it slow.

God did this excite me. I couldn’t believe I was going to go through with it. The last few hours of work was rough, but thankfully we continued to chat, making the time pass by a bit quicker. I learned that he’d been with a few guys in the past and was looking for someone to be discreet friends with.

As my shift was nearing its end, I asked him where he wanted to meet up. He sent me the address of a McDonalds near his home. He wanted to meet me there and then follow him to his place. Leaving work, my heart raced. I still couldn’t believe I was going through with what I’ve been fantasizing about for the last few months.

Pulling into the parking lot of the well lit McDonalds, there he was, leaning against the hood of his car eating a snickers bar. Damn was he sexy, wearing a pair of dark slim jeans and a white button-up shirt.

“Hey man!” I said as I exited my car nervous as hell. “Names Evan.”

“Hey Evan” he replied, “My name’s Alex. It’s good to meet ya in person.”

After a few minutes of small talk, he told me to follow him down to his place. While following him, I couldn’t help but imagine how he looked under his tight European clothing. The questions of, I wonder how big his cock was, or I wonder how good he was in bed, shot through my mind.

Walking into his house, we saw his parents watching TV in the living room. Alex quickly introduced myself, telling them I was a friend from work and that we were going to go game downstairs. Alex quickly ran upstairs to change out of his work uniform, leaving me with his parents. After a bit of small talk, he finally came running down the stairs in sweatpants and a t-shirt.

After a few rounds of call of duty, Alex’s mother came down and said it was great to meet me and that they were going to head off to bed. We decided to start browsing through Netflix and picked a movie to watch.

As the movie went on, I was unsure of how these encounters started. So I thought I’d start to make the first move… Sitting on the couch, I began moving a bit closer to him while slowing moving my hand towards the bulge in his pants. He didn’t seem to mind, so I continued to massage his swelling bulge.

I could tell he was listening to the footsteps above, waiting for his parents to make their way to their bedroom. After what felt like ages, but in reality only a few minutes as I was paying very little attention to the movie, Alex got up off the couch and stood up.

“So what do you think,” he said. “Think ya wanna try a bit more?”

Moving my tongue across my lips, I excitedly said, “I do think I am…”

He slowly began sliding down his sweatpants in front of me. Steadily revealing more and more of his cock as it suddenly sprang up as his waistband lowered. With a very pronounced slap, it hit his well-toned abdomen.

“How’s it look,” he said.

Gazing upon his cock, and neatly trimmed pubes, I just stared for a few moments. “This is the first cock I have ever seen this up close other than my own,” I replied with a smile on my face.

As my hands reached for his cock, I moved off the couch and on to my knees on the floor. It felt so much warmer than my own. After a few minutes of exploring his cock with my hands, I began messaging his well-hung balls, dangling in front of me. His cock was just an inch or two larger than my own and a tad bit thicker, but his balls were significantly larger than my own. The head of his cock was much like mine, I’ve always been told I have the perfect mushroom head. As did he.

Looking up at him, I slowly began moving my opening mouth towards the head of his cock. As my lips met his head, I could feel my heart pound in my chest. Slowly engulfing his head, I swirled my tongue around his member, my tongue tasting an ever so slightly sweet and saltiness.

God, it felt so strange; to have another man’s dick in your mouth. The smell was intriguing, it didn’t smell like BO, but of a scent of that can only be described as pheromones. As I slowly took more of his cock into my mouth, I could feel the head of his cock slid down towards the back of my tongue. I slowly begin bobbing my head back-and-forth.

While gaining rhythm, his hands moved towards the back of my head, providing a subtle push. Slowly guiding his cock further down my throat with every thrust, he softly moaned, “God… Keep doing what you’re doing with your tongue…. That feels amazing… ”

To accentuate the heat of the moment, I began lightly caressing his balls with my hand. After a few more minutes, he moaned, “I’m so close…” Where do you want me to cum…”

I started sucking a little more laborious while pushing myself deeper down the length of his shaft hoping he would get the notion I wanted him to shoot his load down the back my throat. With that, his grasp on my head tightened, using a little more force, thrusting his cock into me rapidly as he shot his load. I furiously began to swallow what I could while taking in the taste of his warm sperm. It was far sweeter and less salty than I expected.

By the time he emptied his load, I could feel his cock start to slightly deflated within my mouth. Continuing to caress his cock with my tongue. “Damn,” he said as he withdrew his cock from my mouth. “You sure you have never done this before?”

While still trying to swallow his cum, I quickly shook my head while looking up at him. “Nope” I finally got out.

“Well,” he stated while showing off a very pleased smile, “you are quite the natural.”

He slid his sweatpants back up, and we sat back down on the couch, somewhat cuddled into each other and continued to watch the movie. As the film was ending, I couldn’t help but move my hands towards his cock once again.

“Ready for more?” he said smiling back at me.

“Oh, very much so,” I replied.

Taking my hand, he guided me towards his bedroom down the hall. As we entered his room, I jumped on his bed reaching for his nightstand and pulling out a condom and lube.

I stood at the entrance of his room. Once again nervous as hell but excited as fuck.

While laying on the bed, he pulled down his sweatpants and removed his shirt. There he was, lying nude on his bed with cock out on display.

Motioning his finger as to ‘come here,’ I slowly removed my pants and shirt as I walked towards him. Before crawling on the bed, I dropped my boxers to the floor.

This is the first time I’ve ever displayed myself like this in front of another guy. Knowing what was coming next excited my hardening cock as I made my way onto his bed crawling in next to him. My head moved towards his cock while my ass moved towards his shoulders.

As my mouth once again moved towards his semi-flaccid cock, I could hear him squeeze out some lube onto his hand. I slowly took my cock into my mouth yet again, slowly massaging his cock with my tongue. As he grew more substantial, I could feel his hands wandering around my hairless ass. Feeling a swirl around my asshole made my cock hard. Slowing sliding a finger into me, I began to moan. The vibrations from my vocal cords massaging his now rigid cock.

With his finger sliding deeper into me, my mind raced. Never have I had anything inside me before. The feeling of his finger stretching my virgin anus sent waves of pleasure over me. As my ass slowly loosened up to his finger, I felt it expand further as he slowly added a second. With his rigid and ready cock in my mouth, he asked if was ready.

I couldn’t believe I was going to do this as I slowly withdrew his cock from my mouth. Looking into his eyes, I smiled. “Here, get on top of me.” he stated, “It will be a bit easier for your first time. You can control it a bit more.”

Straddling his abdomen, I started to feel his cock rub up against mine. That sensation alone made me shiver with excitement. As he placed a condom on his cock, he begins to lube it up.

I slowly aligned my ass with the tip of his cock and began lowering myself onto him. It took a minute for his head to make its way through my tight hole. But once it did, it continued to slide on in, the pleasure far outgrowing the pain. Feeling my anus quickly tighten back up around his shaft made me belt out a moan of pleasure.

With our eyes met, I continued lowering myself on him, taking more and more of his cock. A feeling of fullness swept over me. “Oh my God” I moaned.

“Feels pretty good doesn’t it?” Alex responded.

While slowly starting to move up and down on his cock, I leaned in towards him, my lips meeting his. The scruff of our light facial hair met making a sound that two pieces of sound paper rubbed together would make. While our mouths furiously made out, I began riding him faster and harder.

After a few minutes, he withdrew himself from me. Almost instantly I craved the feeling of fullness I had just seconds ago. He got up and walked around the bed while repositioned me on my knees and arms down in front of me. With that, he crawled back up on the bed and grabbed ahold of my pelvic bones while re-aligning his cock towards my aching hole.

Once again, this time not under my control, he began to enter me slowly. The feeling of unrestricted access as he pushed into me made the feeling of fullness slowly return. Penetrating more profound, he started thrusting faster and faster. I couldn’t help but belt out a loud moan. He quickly moved his hand towards my mouth while softly saying, “Not to loud..”

Removing his hand from my mouth, I shook my head and said I’ll try.

His thrusts grew stronger, gaining deeper access into my bowls. I could tell he was almost all the way in me as I could hear and feel his balls start to slap against my ass. Never in my wildest dreams could I imagine how amazing this felt.

“I’m close, really close,” he said with a soft moan.

With his thrusts quickening, he reached around my leg and grabbed my incredibly stiff cock. As he shot his load into me, he began jerking my cock. It didn’t take more than a few seconds for me to shoot my seed onto the bed sheet below me. As I came, my ass tightened its grip on his cock, causing him to release what sperm he had remaining. As he slowly removed his cock, I could start to feel the feeling of fullness subside.

“Wow,” I said, “that was fucking amazing.”

“Not to bad yourself,” he said while pulling off the condom. “I’ve never had a guy cum while my dick was in his ass. That felt fucking awesome.”

We started putting our close back on and decided to head outside to go for a quick walk and cool off a bit. Both our bodies were both drenched in sweat. As we walked out the back door and made our way towards the driveway, I couldn’t help but notice Alex’s dad sitting out on the porch, smoking a cigarette.

“You think he heard us?” I asked Alex.

“Naw” he replied. “My bedroom is pretty secluded from the rest of the house.”

We continued walking toward the park a few blocks away. After finding a bench, we sat down and started to talk for awhile. The night was cold, but the sky was clear. Stars shining brightly.

We drifted closer to each other until my lips met his once again. After a while, we decided it was late and time to say our goodbyes. While he walked me back to my car, we checked to see if his dad was still out on the patio. Thankfully, he as not. Alex leaned into me give me one big final kiss. Reaching down, I felt his cock once more and said we definitely need to meet up again.

I got back into my car and started driving home with the night’s events replaying in my mind over and over. That was it I thought, I needed more. I was hooked.

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