I should preface this story by saying that I am straight, generally, and had never been with a guy before this story. This was a few years ago, when I was 24, living in New York City and dating a girl long-distance.
My girlfriend and I had been together for a few years, since college, but an amazing opportunity took her to another city for two years. I found myself on the Greyhound a lot and, when I wasn’t with her, often sexually frustrated–especially as I saw all my friends living it up as single guys in their twenties in NYC.
One day, on one of those nights when I was away from my girlfriend all my friends were out hooking up, I strayed from my normal porn appetite onto Craigslist’s casual encounters page. I wasn’t really planning to do anything there–I had never cheated on her–but I decided to browse and click a few ads. I started on the w4m section, but it soon became exceedingly clear that every one of the ads there was posted by a prostitute or a spammer. So I drifted over to the m4m section, mostly out of curiosity–and while most of the ads were not my style, one caught my eye. It was a guy a little older, 28 years old, who had posted a simple message offering a free, no-strings-attached blowjob to a straight/curious guy. His apartment would be dimmed with straight porn on the TV, and whoever answered the ad could walk in, get sucked off, and leave anonymously.
I found myself getting hard at the thought, so I jerked off–and had a surprisingly intense orgasm–and went to sleep.
Over the next few months I found myself back on casual encounters more and more often. When regular porn failed me, I would browse the ads and read the scenarios different ads were proposing. Some of them would resemble that first ad, and I would get turned on and cum. It was a simple pattern and, though I recognized I was getting a little turned on by the thought of a gay encounter, I didn’t make much of it. Honestly I think what got me excited was the idea of a free, easily available, anonymous guilt-free blowjob I could get at any time I wanted to.
Then came a day in early spring when two things happened that changed my usual pattern. First, it was a beautiful spring day, so my friends and I all left work early on a Friday and got a little drunk at a bar called the Frying Pan, which is outdoors and on a boat docked in the Hudson River. By dinner time, I was headed home as all of my friends had left to meet up with their hookups or just hit a wall early and went home. Second, when I got home and logged on to craigslist, I saw an ad identical to the ad I had seen that first day, offering an anonymous blowjob with the lights dimmed. Tipsy, I replied that I was interested, sent a picture of my cock, and asked for details. The guy replied almost immediately telling me his cross streets–close by to my apartment–and saying he was hanging out and could meet up anytime. We exchanged a few emails and then, nervously, I wrote, “Okay. I’m in. I can be there in 10 minutes. Let me know the address and apartment number.” He replied and, shaking, I laced up my shoes and headed over.
I stood outside his door for about a minute before I worked up the courage to buzz, but then I was walking up the stairs and at the door to his apartment before I knew it. He told me his name was Zach, and… well… the thing is, he was indisputably hot. Fit, muscular but not bulky, big blue eyes, dark hair and a short beard.
His lights were dimmed as promised. I walked in.
Zach led me over to the couch and kneeled down in front of me without a word. He unbuttoned my jeans, and I felt my cock stir as his hands fumbled with the zipper. He lowered my pants and slid my boxers carefully, the elastic catching for a minute on my increasingly erect cock before it swung free. What he did next was incredibly hot: He looked up at me, locked eyes, and slowly took my cock in his mount, sliding his lips all the way down to the base without so much as a gag. I moaned.
I had been nervous, but now that my cock was in his mouth, it felt amazing. He slid his full lips up and down my shaft, swirling his tongue as he reached the top. His hand cradled my balls, and he raked them gently with his fingernails. Slowly, almost excruciatingly so, he slid up and down my cock, and I was in ecstasy. It was some of the best head I’ve ever gotten.
He stopped for a minute to pull off his shirt and unbutton mine, and then moved his lips up my chest, kissing gently, as he took my nipple in his mouth and swirled it with his tongue while stroking my cock with his hands. He did the same to the other nipple, then kissed his way down my happy trail back to my cock and resumed sucking, but faster this time. He stopped to lick my balls, gently but passionately, a few times, keeping me on the edge of pleasure. Then he stopped and said, “do you want to go to my room?” I did.
We moved to his bed, and I wasn’t sure what to expect, but he positioned me so that I was sitting on the edge of the bed with him kneeling in front of me. I thought he was going to start sucking me again, but instead he leaned me back onto the bed, lifted my legs, and moved his mouth down to my sphincter. I felt his tongue explore the edge of my asshole, gently at first, and then it was inside me, swirling and probing in every way. I have never felt anything like it in my life, and I almost came on the spot, but he was an expert and brought me right to the cusp of orgasm but never over it.
I can’t remember how long this went on for, but after an ecstatic period of time when he was rimming my asshole and stroking my cock ever so slowly, he stopped and motioned for me to turn over. I had only ever intended to get a blowjob, but at this point the pleasure–and the desire–was unimaginable, and I would have done anything he said. I kneeled on the bed, my ass spread facing him, as he went back to my asshole, this time with a better angle that let his tongue go deeper than ever. He reached his hand around to stroke my cock from behind as he did it, and it felt amazing. I felt myself spasm–so close to orgasm–but he did too and pulled back just ever so slightly.
Somehow in the midst of all of this, his pants had come off, and with my head pressed down against the bed like a dog, through my own legs, I could see him stroking his cock. It was 6, maybe 6.5 inches long and a nice girth, cut like mine. It was hard as a rock. I moaned at the sight of it.
“Is this really your first time with a guy?” he panted in between licking my taint and sphincter. I told him it was, and as I did he left my ass and slid his way up my back, so that he was embracing me from behind, his hard stomach against my back, one hand on my cock and one hand on his own. With that hand he reached to his nightstand, where a bottle of lotion sat, and put some on his hand. Then slowly, gently, he pushed his index finger into my asshole, still stroking my cock with his other hand. I exploded with a wave of pleasure, desperate to cum but still kept just ever so slightly on the edge of orgasm. He began fingering my asshole, slowly but firmly, for some time, torturing me by keeping me as close to orgasm as possible but never letting me reach climax. I was sweating, and so was he, and our sweat mingled on my back and his chest.
He pulled his finger out for a moment and shifted his weight, and as he did so I felt the head of his rock hard cock brush against my open, lubed-up sphincter. He started to move his fingers back down, but I stopped him. Instead, I arched my back to push my asshole against the head of his cock, taking just the smallest bit of the tip into me.
“Are you sure?” he started to say–but in that moment, I had never wanted anything more in my life. Nothing mattered more than having his cock inside of me. I arched my back further and, after a brief resistance, felt the head of his cock slide past my sphincter and into my ass, sliding against my prostate as it did so. I leaned my weight backward slowly, and his cock pushed into me, filling me up. I moaned, and he moaned. Then he began thrusting in and out of me, slowly at first and more aggressively as I began to adjust.
It felt amazing, and he kept his free hand on my cock the whole time, stroking me–except now, as he convulsed with his own pleasure, he could no longer keep control. I felt myself tense, and then a wave of pleasure like nothing I’ve ever felt *exploded* through me–and ropes of thick hot cum shot from my cock onto his bed at first, and then oozing onto his hand as I continued to pulse.
As soon he felt my hot cum begin to cover his hand and drip down his wrist, I felt him tense up. He moaned, thrust once more deep into my ass, and I felt his hot seed fill me up, shot after shot inside me.
We collapsed on the bed.
After that I was in a daze. He went to get a glass of water, and I put on my clothes quickly. What had just happened? And–why had I enjoyed it so much?
I decided to get out of there–and his ad had said to cum and then leave–so I did. I muttered a thank you on the way out, we shook hands (and the laughed because of how ridiculous that was) and I sped down his stairs and out his door into the cool spring night.
I never saw Zach again, but the encounter opened up a whole new chapter in my erotic life. Maybe I’ll tell those stories here some other time ;)
Source: reddit.com/r/gonewildstories/comments/4ggqtd/answered_a_craigslist_ad_from_a_guy_willing_to
wow!
That was amazingly hot. I browse the casual encounters sometimes too, just because I get turned on by the possibility. Are you still with the same girlfriend?