(TLDR at the end)
So this takes place in 2001, when yahoo chat was still reasonably popular. I was 21 at the time and active duty military stationed in the Southeast U.S. I had discovered that chat rooms were an incredibly easy way to find girls- experience taught me that most of the girls willing to meet up with an internet rando were pretty much up for anything.
I first met “Lauren” in a chat room for the state I was stationed in, South Carolina. We got to talking and I found out she was 18 and a HS senior living in upstate NY, but she was going to be visiting family near where I was over her spring break in a couple of weeks. Obviously, digital pics weren’t near the quality they are now, but we exchanged the few uploaded pics we had of ourselves and liked what we saw (nothing NSFW). She had a cute face and straight, light red hair. She told me she was pretty tiny- only 4’11” and 95 lbs. I love petite girls, so that pretty much sold me.
We IMed each other over the next couple weeks and solidified plans to meet up on the Saturday she was down here. Our conversations were flirty, but not super explicit. However, I could definitely read between the lines that this girl was
A. DTF
and
B. Possibly crazy.
But at 21, I really didn’t care if she was Stage 5 or not, especially with her living 800 miles away.
So the Saturday comes around and I leave about 9 in the morning on the hour drive to where her family lived. We came up with a story to tell her family about how we went to school together and I had graduated a few years prior and was now in the military stationed nearby… mainly so her family wouldn’t think (know) she was meeting up with a random online guy. I get to the area about 10 am and check into a hotel that had a room with early availability. Gave her a call and let her know I was on my way over.
During our conversations, we got on the topic of what type of clothes are most attractive on the opposite sex. She told me she liked the unbuttoned short-sleeve button-down with wife beater and Gap-style cargo pants (it was 2001…), which is what I mainly wore, so that was easy. I told her that my biggest weakness was the Britney-style school girl look (10 years of catholic school will do that to you). I pulled into the driveway at her Aunt and Uncle’s house, completely ready to be interrogated by one of them, but thankfully I saw the front door open up and Lauren come out all alone before I could even get out of the car.
Ho. Lee. Shit. was all I could think as I got my first real look at her. She wasn’t wearing some “loose variation” of the school girl look, but the actual thing, to a T. Tight white shirt tied in front, showing off her fit midriff, unreasonably short plad skirt with white thigh highs, the shiny black shoes… and to cap it off, she had her red hair in two pigtails. If her intention was to look like a complete jailbait slut, she nailed it. I was fucking blown away. No idea how she was able to pull that off without getting questioned by her family.
She opened the door and climbed in and we exchanged a sort of awkward hug, then I backed out of the driveway as quickly as I could to avoid any possible interaction with her family. We talked on the way to the hotel, complimenting each other on our looks and admitting we were both pleasantly surprised that we actually looked like our online pictures. Of course, I praised her highly on her outfit, letting her know how ridiculously hot she looked in it. I’m sure she noticed my tented khakis, which gave credence to this.
We arrived at the hotel and went up to the room. Didn’t really have a plan for the day, I just figured we’d play it by ear. I told her that I have a quirk about having to take a shower after long drives (partially true), so if she didn’t mind, I was going to do so really quick. She said she didn’t mind, so I casually stripped down to my boxers while she sat on the bed. (To anyone curious, I was 5’10” about 155, fairly toned runners body.) I could not stop checking her out the whole time and I’m sure I was sporting an obvious semi. She was shy, but flirtatious as we talked and it was a huge turn on. I walked into the bathroom, leaving the door slightly ajar- I figured that she would interpret that as a sign that I was comfortable with her… or that she was welcome to join me.
My shower turned out to be uneventful. We actually continued our conversation through the open door while I was in there. I stepped out and dried off, then wrapped the towel around my waist. I opened the door the rest of the way and walked back into the room. Simultaneously, my jaw dropped and my dick went from 6 to midnight. Lauren was sitting on the edge of the bed facing the bathroom door, her arms behind her supporting her tiny frame. Her legs were parallel and her skirt was pulled up an extra few inches, giving me a peek of her small white panties. Her shirt was not only untied, but unbuttoned, giving me a look at her white lace bra and more than ample cleavage.
I think I managed a “Wow…” as she giggled nervously. I immediately went straight to her and pushed her down onto the bed, laying down next to her. We started making out and hands started exploring. Reaching under her skirt, I felt her soft but firm ass, bare aside from a thong. Within seconds, she seemed to switch personalities- her mouth and hands became incredibly aggressive, along with her words. Apparently that was the icebreaker she needed. The dirty talk just flowed out of her, telling me how fucking horny she was, how bad she wanted me, and what a dirty slut she felt like being in a hotel with a total stranger.
It was shocking at first, caught me a bit by surprise, but I adjusted quickly. Admittedly, I didn’t have a ton of dirty talk experience at that point in my life, but I just kind of followed her lead and it seemed to work for her. She wasted no time reaching down and squeezing my rock hard dick through my towel. I was kissing her neck, earlobes, and upper chest… everything I did made her moan loudly and grind her crotch against me. I literally could not believe how horny this girl was.
After grabbing her tits through her bra, I realized how stacked this girl really was. Because of her small frame, I didn’t expect much in the tit department. I helped pull her shirt off the rest of the way and unclasped her bra. An amazing set of C cups were waiting for me underneath. I have no idea how a girl that small ended up with tits that size, but I wasn’t about to question it. They were perfectly shaped and looked enormous on her body. I continued to match her aggression, mauling her tits with my hands and mouth. Her moans went up another octave and she flung my towel open, then proceeded to stroke my cock furiously.
Things moved quickly after that… I damn near ripped her thong, I wanted that pussy so bad. She was freshly shaved, smooth as fuck with no signs of stubble. I couldn’t wait to see how tight she was, so I sunk my middle finger into her. “Soaked” and “tight” barely begin to describe the state of her pussy. I don’t think I’ve ever felt one that tight. I went in and out of her, knuckle deep and she was loving every second. No matter what I did, she was into it. I felt like a fucking god.
The next 30 minutes or so was like a blur… she came from me fingering her, laid me back and sucked my dick while rubbing her own pussy, then rotated herself so we 69ed, and came again from my mouth and tongue. I could’ve come easily throughout this, but managed to hold off… I definitely wanted to get my dick inside her before that happened. I should mention at this point, the skirt and the thigh-highs remained on, only adding to the naughtiness of everything.
With a barrage of filthy obscenities, she laid down and told me she wanted to get fucked. I quickly obliged and soon found my way inside the wettest, tightest, smoothest pussy I had ever felt. I could tell she had no interest in me starting out slow, so I just started pounding her right off the bat. Within a couple minutes, she was having her 3rd screaming orgasm and I was right on the verge myself. I was getting ready to unload inside her (she said she was on the pill), when she stopped me.
“I want you to tittyfuck me!!”
She wasn’t asking, she was demanding. I was absolutely beside myself with the level of sexual jackpot I had hit with this girl. With her laying flat, I mounted her miniature frame and placed my throbbing dick between her amazing tits. She pulled me closer to her mouth and gave me a quick, sloppy one before letting me go back into position. She pushed her tits together completely enveloping my cock and I immediately started thrusting. Between her saliva and the precum gushing out of me, the only friction I was feeling was the good kind. As I’m doing this, she’s pinching her nipples, moaning, and gyrating her body as if she were getting fucked. I was dumbfounded… is there anything that doesn’t turn this girl on??
Between the physical pleasure I was getting and witnessing hers, I knew I couldn’t hold out much longer. I started groaning louder and she picked up on it right away.
“Come for me, baby! Right now, I want it so fucking bad!”
That was it. With a primal grunt, I unleashed an enormous load all over her face and into her pigtailed hair. I can’t say for sure if this elicited another orgasm out of her, but it sure as fuck sounded like it. She was crying out loudly as her face got covered. I kept thrusting until every little bit of my come was somewhere on her. The aftershocks coated the inside of her tits nicely.
We both began returning to earth as I watched her scoop my globs of come off her face and into her mouth. I was simply blown away by this girl. I’d be lying if I said I remembered our post-coitus conversation… I was far too euphoric and exhausted.
So after a little recovery time, which consisted of my hand on her ass as she snuggled/grinded herself against me (I’m 100% sure she would’ve immediately been ready to fuck again if I tried), I craved what every post-orgasmic guy craves- a sandwich. I told her it was time for lunch and we started getting dressed. She put her sexy little outfit back on and we headed out. It occurred to me that this little slut never even washed the traces of my cum off her face, hair, or chest…
There was an outdoor mall one exit down from the hotel, so we headed in that direction. She started up the teasing as soon as we pulled out of the lot… skirt pulled up, rubbing herself through her thong, under it… playing with her tits… I could’ve wrecked the car half a dozen times in the 10 minute drive watching this.
We walked around the mall, got a bite to eat and were super handsy the entire time. She got stares everywhere we went because of her outfit, but neither of us cared since we would never see these people again. (Being in the Bible Belt, we definitely left a lot of surprised looking faces in our wake.) She also told me she was bi and had a girl she fooled around with fairly regularly.
I was hiding boners the entire time and after walking around some more and letting my food digest for a bit, I was anxious to get back to the hotel and back to business with this little firecracker. We got back in my car and with zero hesitation, she sits up in the seat and removes her thong right there in the parking lot. This initiates a pretty hardcore makeout and fingering session, until she started to get so loud I was afraid we were going to get caught. I start driving and she plays with her pussy the whole way back.
The rest of the day and night were nuts. We fucked the entire afternoon, in almost every possible position, in the bed, in the shower, against the wall. Wild, screaming, hair pulling, back scratching, skin biting, dirty talking, raw fucking. I licked that bald pussy like my life depended on it. She sucked my cock like a fucking Dyson. This girl was like the energizer bunny of sex and I was feeding off her energy. When we weren’t fucking, she was playing with her tits or pussy, shortening my rebound times to almost nothing. I came on her and in her until I had absolutely nothing left. She was and is easily the biggest nymphomaniac I have ever met. I am personally not into anal, but there’s no question she would’ve had zero reservations about that either.
That night, she had agreed to go out with her cousin and her boyfriend to dinner, then to a movie. She invited me along and although I initially wasn’t thrilled about the idea, I knew that if I wanted more of that pussy, I’d have to go along with it. I dropped her off back at her cousins so she could change, then went back about an hour later to pick her up. She came out still looking hot as hell in a tube top and slightly longer, but still short skirt and her hair down. We followed behind her cousin and her boyfriend to one of those southern cafeteria-style bbq places.
We eventually made it to the movies and cozied up to each other when the lights went down. After a little while, we noticed that her cousin was getting a bit frisky with her boyfriend, so we figured we had a green light to do the same. We made out a bit and teased each other as much as we could. At one point, she takes my hand and pushes it into her hair just above her right ear.
“Do you feel that?” she whispers into my ear. A section of her hair was hardened and crunchy.
“That’s you…”
This dirty fucking slut hadn’t even bothered to wash the dried cum out of her hair. The amount of primal lust I had for this girl was immeasurable.
As the movie was getting over with, I was trying to figure out how we could ditch the cousin and bf and get back to the hotel. Thankfully this happened on its own- her cousin asked us if we would mind if they took off and spent some time alone. We were obviously cool with this, so the girls agreed on a time that we would all meet back at home together. This left us about two hours to make the most of. We beelined for the hotel and of course she had her panties off and fingers in her pussy within minutes of getting in the car.
We spent the next couple hours ravaging each other. I managed three more loads and who knows how many more orgasms for her. By the time I dropped her off back at her family’s place, I was absolutely spent. I had and have never fucked so much in a single day. This girl was straight up insane for sex. I slept like a baby that night and immediately had to jerk off the next morning, as I recounted the prior day’s events.
Thankfully, that wasn’t the end of us. We kept in touch after she went back to NY and she convinced me to buy a webcam. We IMed each other and watched each other play on cam. She would get naked and stay that way throughout our entire conversation. However, as time went by, my theory about her being a Stage 5 Clinger became more apparent. I took some steps to distance myself from her, but her sluttiness just turned me on so much, I couldn’t bring myself to fully sever ties. Eventually, 9/11 happened and I deployed overseas soon after. Like a true patriot, even when we couldn’t cam, she always kept my inbox full of fresh nudes and dirty messages.
Early on, we discovered that she lived very close to my own aunt and uncle in upstate NY, so we ended up meeting again in 2003. I’ll tell that story as well, if there’s enough interest. Unfortunately, we lost contact when MySpace died out, so that’s where our story ends.
So, “Lauren” ?, if you happen to stumble across this, just know that even after 19 years, you’re still making my dick hard!
TLDR: met a girl in a chatroom, met up in real life, she ends up being a complete nympho and gave me an incredible day of dirty, hotel room sex.
Source: reddit.com/r/gonewildstories/comments/ftcpnc/old_school_chatroom_hookup_goes_pretty_well_mf
Awesome!!!