It feels like the days of Craigslist personals was a lifetime ago.
My first time stumbling into this space, I was a junior at Brigham Young University in the heart of Utah, and it remained a point of fascination for me for some time. At the time, I was something of a “true-blue Mormon” and too straight-laced to actually try meeting someone. But I loved to browse ads. I created burner email accounts and tested the waters from time to time.
If you ever had the (mis)fortune to participate in this wasteland, particularly the w4m section, you quickly became aware of two things: 1) The scammer-to-real-person ratio was around 1000:1, and 2) The number of guys competing for those few women was also around 1000:1. There’s no better way to explain Craiglist than *sketchy as fuck*, and I truly do not understand how *any* woman *ever* felt comfortable enough with it to meet someone in real fucking life.
This is the story of how I met Helen.
I had transferred universities and was in a significantly more liberal part of the country. Switching schools was a breath of fresh air. I was still conflicted about my faith, but the confliction at that point was mainly sexual rather than theological. Unfortunately. However, getting away from BYU left me accountable only to myself rather than a fucking office of Mormon Dolores Umbridges.
I began keeping a Craiglist ad up more or less full time just to see what rolled in. Not unlike a fisherman leaving a line on a pole holder while attending other matters around his boat. I won’t claim I had the best game in town, but I had something of a stroke of genius one night that yielded a surprisingly successful ad that led to a few encounters I hope to write about. I wish I could remember it word-for-word now, but it was fairly tongue-in-cheek and poked a little fun at all the ads claiming to be massively hung as well as poking a little fun at myself. I’m reasonably above average, but far from the largest cock in the world, so there was an air of truth to my ad.
I also did not post a dick pic. My pics were typically in jeans and shirtless, never showing my face.
In any case, one night I found a response to my ad. It’s been over a decade since this encounter, so I won’t pretend to remember anything about our exchange. All I remember is a cute girl sent me her face, a clothed body pic, and enough details for me to believe she was real, and we exchanged numbers from there. She was 21 or 22, a few years younger than me at that point.
She wanted to get fucked that night. Just come straight over to my apartment and get down to business. Now… this was incredibly naive of me… but I agreed. I gave her my address (sans apt #) and I met her at the main entrance of the building to let her in. To any of my readers, I plead with you TO NEVER DO THIS, man or woman. It’s just straight up bad business. Good god, I had no way to verify this girl’s identity, and I just let her come straight to my building. Any dude could have catfished me, then beaten me to a pulp or robbed me or worse.
I lucked out. Helen was who she said she was. I let her in, grabbed her by the hand, and led her to my apartment. She was as cute as her pictures. A bit hippyish–but clean. She had dreads. Brown hair, brown eyes, pretty mouth with medium-full lips. She was slender and had really small boobs and a pretty nice ass. Before we got to my apartment, I pushed her up against the wall of the hallway and kissed her. She was a damn good kisser. She tasted a little of wine, and I wondered momentarily about whether she was safe to have driven here.
I let us into my apartment. Now… I was a typical college guy. I split an apartment to save costs. The apartment was far from classy. But what wasn’t so typical is I sort of still had a foot in the Mormon church. My roommate was Mormon, and I was outwardly still playing the part of a “good Mormon boy.” There was a legitimate chance my roommate would rat me out to Mormon leadership if he knew I was bringing girls home.
Have you ever heard that joke about why you invite 2 Mormons with you fishing? If you only invite 1, he’ll drink all the beer.
That applied here. Just replace beer with pussy and drinking with… well you get the idea. Part of the reason I had chosen a Mormon to room with was to entice me NOT to bring girls home. Oh well.
This is a long-winded way of saying we did NOT go straight to my squeaky twin bed in my room that shared a wall with my VERY Mormon roommate. No way. I took her to the living room, laid out some super awesome foam pads on the floor with a few blankets, and put on the Fellowship of the Ring with the volume up a bit to cover up our noise. I don’t *think* I pulled out any sleeping bags, but I can’t say that for certain.
She was kind enough to not ask any questions. Helen was just here to fuck.
Once the room was arranged, she jumped my bones and we locked into a steamy makeout session that escalated quickly enough that within 5 minutes she was buck naked and I was buried tongue-deep in her pussy.
I definitely had concerns about her hippy-looking hygiene at first glance, but this girl smelled good and was smooth as butter from the waist down. Soft legs, bald pussy. Her lips felt soft to my tongue, and she tasted clean and delicious.
The funny thing about this hookup is Helen really, really wanted to just get pounded. I may not have caught on right away, but in hindsight it’s pretty clear. Just after we both were naked but just before I sucked her clit into my mouth, she looked me dead in the eyes and whispered “I want you to fuck me.” Ok, as cliche as it might sound, not only is consent hot, but it’s crazy hot to hear a girl tell you what she wants. Helen told me what she wanted. Instead I went down on her.
Hey, in my defense, I love eating pussy. I’ve said this in previous stories, and I’ll probably say it again. I just love it. And hers was delicious. I devoured her. I wanted to make her cum, but I may have sensed her impatience and came up for air before too long. I kissed her with her juices all over my mouth.“Do you want me to go down on you?” she asked. She was being a very conscientious partner. I probably should have just fucked her. But instead…“I mean… I wouldn’t object…”
The blowjob that followed has stuck with me over the years. It wasn’t really the best I’ve had, but it was raw, animalistic, and really really fucking hot. She took me in her mouth and just started slamming me into the back of her throat. It was 0-60 instantaneously. She couldn’t deepthroat me, but instead she would just ram the back of her throat with my cock over and over and over and over. It. Was. Sexy.
I held up her dreads so I could watch her pretty mouth devouring me. It’s burned in my memory.
Finally. Finally after all the foreplay I put her on her back and lined my cock up with her entrance. I remember pushing slowly into her, but she grabbed my ass impatiently with both hands and pulled me into her until I was balls deep. The moan that escaped her lips was equal parts relief, pleasure, and release of pent-up frustration.
I entered her pussy raw. Also something I’ve wizened up on in my old age. Wrap your dicks, kids. And yet even being smarter now, the sensation of entering Helen raw is also burned in my memory.
I love the moment of initial penetration. The way her pussy felt while she pulled me into her is one moment in this hook-up that has and probably will always stick with me. Her pussy was oddly cold, and surprisingly dry for the amount of foreplay we had just engaged in. Despite that, she literally pulled me forcibly into her, and the chill was a pretty great sensation. I could feel every fold of her pussy while my cock was pulled deep into her.
Let me assure you she did not remain dry. Once I was in she became quite wet. We fucked slowly in missionary for some time before she began encouraging me to fuck her harder and harder. Soon I was pounding Helen for all I was worth.
Remember my roommate? It was about at this point I heard something hit the door to his room. I assume he heard us and threw something in frustration. So much for staying incognito.
In any case, I put my hand over Helen’s mouth and gave her a “shhhhhhhhh” while I pounded her. She moaned into my hand, her eyes looking into mine almost pleading. I kissed her and her moans filled my mouth. By this point our bodies were slick with sweat, and we were slipping and sliding all over each other. Unadulterated fucking. The girl could take it and take it well.
I flipped her onto her knees and entered her doggy. I noted that she hadn’t cum yet and I wanted to correct that. I gave her the reach-around and began fingering her clit while fucking her from behind. My sweaty chest rested on her sweaty back and our slick bodies continued pounding each other into the night. As I continued fingering her clit, I felt her orgasm rising. I slowed my fucking and focused more and more on the clit till I felt her build and release, whispering in her ear to stay quiet while the wave crested and broke. She was a good girl and kept her voice to a whisper.
I kissed her neck and began fucking her again. Hard. She begged me to go harder. I went harder.
This was all super hot, but I’ll confess that I hit a plateau. We fucked like this for another 10 or 15 minutes minutes, and I felt a building pressure to cum so that I didn’t wreck this poor girl. We were sweaty, tired, she kept looking back at me expectantly, but I just couldn’t get there. So I did something I never imagined I’d do, and I faked an orgasm.
We spooned for a little bit, then we got dressed and I walked Helen out. I kissed her at the door of my building and never saw her again.
Source: reddit.com/r/gonewildstories/comments/u0bgzu/my_first_craigslist_hookup_m26_f21