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My First Time...
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My first time with another man I honestly had no real idea that that's what I was going to do that night. I was maybe 19 or 20, still sore after a bad breakup and was sipping my way through a bottle of whiskey, when desperately horny, I hopped on Craigslist. Skimming the W4M section, I saw immediately that almost no "real" women were there - obvious hookers and links to malicious sites and the whole mess. Now, as I've said in my bio, I've always had a fantasy where I wore women's clothes, and had experimented with some catfishing roleplay on chat sites, so I decided I would post in the M4M section. The attention would be enough to get me off. So, I made a post in the M4M Personals section, something along the lines of this:
5'2" 100lbs 19 white male with long hair here, looking to give head for the first time, prefer older (40+)
I assumed it wouldn't get that many hits, it was late (maybe 1am?), but my email was flooded with about 15 new messages, almost all of which were actual people and not bots. I was stunned....and my curiosity and the alcohol started to work together. I couldn't contain my erection. I was almost to the point of cumming just reading through them all. Before I came in my pants (and thus came to my senses), I ran to the bathroom, to shave my face and ass - to make myself as feminine as possible. I had no girl's clothes so a tiny tshirt and sweatpants would have to do. I went back to my computer after showering and cleaning myself up (and moisturizing my little bubble booty) and decided on the sanest-sounding email, and responded to him. I wanted to make it quick, and he obliged; we agreed to meet behind the Golden Corral nearby.
I was parked for several minutes, heart pounding, when he pulled up beside me. It was dark out, no street-lights, though in retrospect it was an insanely open area and I am surprised we did not get caught. Maybe it was later than 1am? Regardless, he motioned for me to hop into the passenger seat, and I made the transition from my car to his, taking one last sip of my water to calm my nerves. He looked like everyone's dad - portly, wide eyes, baseball cap and wifebeater. Despite my pounding heartbeat, I reached over fairly confidently, rubbing him through his pants. I'll never forget, he looks at me and goes "I don't do this sort of thing often...", as if I would go and tell on him. (although, I guess technically, here I am....)
He stiffened almost immediately, and pulled his pants down, and I saw another man's cock for the first time. It was much smaller than I was expecting, to be honest - it was thicker than mine, but shorter by an inch or more, and Im a smidge over six inches. But this was something of a relief, to be honest, and so licking my lips, I slowly lowered my head down into his lap, sliding his quivering, stiff cock into my open mouth. The moment my tongue and lips touched his tip and shaft, he let out a legitimately satisfied moan, and it spurred me to close my mouth over him and bob my head up and down, working him slowly at first, and then faster, more sighs and moans emanating from him. He had strong, rough hands, and he soon found himself reaching under my sweatpants to squeeze and knead my ass - which I had stuck up in the air as I went down on him, almost instinctively - and then tangled his fingers in my long, dark hair, not aggressively or forcefully, but commandingly guiding my head up and down as he approached his climax. He came in my mouth fairly quickly, probably within five or six minutes - his moans had suddenly paused and he tensed, alerting me just before a warm, salty sensation filled my mouth. I swallowed quickly, sucking the shaft clean and wiping my lips. Sweat beaded my forehead, my lips and tongue were strangely numb, like from repeated abrasion, and my cock was quivering and ready to be brought to its own climax - but I would not let him touch me. Bidding him goodbye, I immediately hopped back in my own car and drove home to masturbate to my newfound experience.
That night, however, was a wild one. Encouraged by how quicly that all went, I had two more encounters that same night, all in a span of about four hours. Next time I'll talk about those I guess :)
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Posted on : Nov 24, 2019
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Commented on Feb 25, 2020
ty :3 I felt I had to tell them or I would go mad lol
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Commented on Dec 1, 2019
Great story! Thanks for sharing your experience!
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