At 18 my life was pretty chaotic. I was going through some significant family issues, I had a down in flames type breakup with a girlfriend and then promptly started college. Prior to leaving for school I had my first gay experiences with a classmate (also 18). All these factors added up and so when I moved to a larger metro from a small Midwest town I was eager to explore.

The following chapters are true stories of my Craigslist Personals encounters before the feature got shut down. The only details I’ll adjust are names and locations. I’ll do my best not to exaggerate. Each chapter will be dedicated to a different encounter.

I knew pretty decidedly I was bi when I arrived at university. I’d given head a few times and been fucked by a classmate. All fine, very normal first time stuff, not even really worth a story. I also knew I didn’t want anyone to know that part of my life. It was a small part of who I am and still is, so keeping it DL was very important for me. I definitely chased girls but there were many nights jerking off that I looked to bi or gay content.

For those who aren’t familiar, Craigslist used to have a personals section for things like Missed Connections & M4M, if you posted or replied to an ad it would send with an anonymous Craigslist email. I don’t entirely remember how I first discovered the Personals section of Craigslist but as soon as I did it became a regular thing for me to read the M4M ads and fantasize about meeting up with the faceless cocks. I would sometimes reply to a few but never really had any intention of going through with it due to nerves and safety.

Around the same time I discovered smoking weed and one night I was feeling particularly horny after a few bowls. My roommate was out for the weekend and six months removed from my first experience, I recognized this as my next chance to explore.

I’ve never had a six pack but have always stayed in pretty good shape. Same thing when it comes to my cock. I’m not going to be bragging to anyone but I’ve never been shy to pull it out. I took a few pics and in my state I found the courage to post an ad, “18 college guy looking to host in dorm”. I put a good description of what I wanted and posted a body photo that showed my ass and a cock pic.

I put my phone down and played a few rounds of my video game before checking my email. After 15-20 minutes I had 14 emails with guys looking to come over. Some that were obvious spam or sketchy but probably 5 that seemed like good candidates.

I read through the messages and the one that caught my eye was a black guy, Andrew. He was the closest to my age that responded at 22 and said he wouldn’t be out of place in the dorm. The photo of his cock and body was nice. He had a six pack, his arms were toned but not thick, and a very similar length cock to me. He was somewhere around 6” but his cock stuck straight out with the same girth all the way down. The guy who took my virginity was slightly smaller than that so I knew it would be fine if we got to fucking. The last thing I wanted was a huge dick to split me open.

We exchanged emails back and forth for 20 minutes before I felt comfortable enough to invite him over. The plan was I would wait for him to park and he would walk behind me at a distance into the building I unlocked. I’d then walk ahead of him into my room and he would duck in shortly behind me.

This all went very smooth but my heart was racing as he closed the door. He was handsome enough but I could tell from his expression he was anxious to get started and leave. I tried to ask a few warm up questions but didn’t get much from him. After the second “yeah” to one of my questions I asked him to get his cock out. I sat on our giant bean bag chair in front of him as he pulled down his underwear to expose his semi hard cock. I slowly jerked it as I took a minute to realize he was the first black person I had been with. He snapped me out of my daydream by grunting “suck it” at me.

I started at the tip and slowly licked up and down his cock. Working my tongue around his shaft I made my way down to his balls. I felt his cock start to harden against my face as I swirled my tongue along his smooth sack. I moved back up to his cockhead and took him into my mouth. He must have been jacking off before coming over because the taste of precum hit my tongue immediately. His cock started to fully harden in my mouth and I was getting insatiably horny myself. Pulling myself off his cock I reached into my drawer and pulled out a condom and lube.

I truthfully was not well-versed in how to prepare for anal at 18. My first time he slipped in and we just waited for the pain to subside. I knew Andrew would want to fuck right away so I took some lube and did my best to finger myself quickly as he slid the condom on. Andrew’s cock was slightly thicker than I had been expecting, definitely thicker than the first guy I’d been with so I started to get a little nervous. I bent over the bean bag and felt his tip line up with my hole. He gave a push and I hissed as he popped in.

“Hold on, hold on, hold on” I whimpered. To my surprise he was gentle and eased his way in. After a few breathes I started to push back on his cock. He took that as his cue and started to thrust into me. There was still a twinge of pain but his cock felt great as it hit deep.

After a few minutes he leaned forward and put all his weight on my back. He started to grind his hips with his cock buried all the way into me. This felt incredible and I didn’t want it to stop but he soon after whispered in my ear “I’m getting close.” and proceeded to thrust harder into me.

I really like taking cum but was obviously careful with a stranger. I didn’t want any risk and truthfully also wanted to feel like a slut, so I managed to huff out between thrusts “Cum on my back”.

He slipped out, pulled the condom off and threw it on my back. I looked behind me as he started to grunt. Warm shots started to land on my ass. I’d been jerking off the whole time and as the rest of his load fell on my back I started to shoot as well.

He cleaned his hands off on the towel I had beneath me and said thanks as he was putting his shorts back on. I said no problem as I laid there covered in his cum. Not even really saying goodbye he snuck out, leaving me to clean up and that was the last I ever saw of him.