One Weekend, 3 Ex Girlfriends Pt. 01

***Author's note: This is closely based on a true story, with names and minor details changed to protect the not-so-innocent. Everyone was well over 18 when this occurred and certainly should have known better! If you have an issue with some moderately kinky rough sex, drinking, or cheating please don't read. Also, this took place around 2010, so bear that in mind when it comes to the instant messaging and livestreaming. Part one is fun but fairly tame; in part two things get a bit more kinky and dirty. And part three will shift over into the fetish category - but there'll be a disclaimer at the top of all of them just in case.***

Towards the end of college I was in a long-distance relationship with my girlfriend Kate. I'm not really sure how that happened - there's no way I should be trusted in any relationship let alone one where there's over 200 miles between us - but it was pretty clear it wasn't working out. Sure, the sex was still great but that only happened once a month when we got together and the rest of the time we mostly fought via text. Not a great situation and pretty much all my friends knew that.

At that time I was sharing a house with three friends, including an ex-girlfriend, Chris. We'd dated our Freshman year and had a pretty amicable split. Both of us had been looking for more of an initial college fling than anything too serious, so it was pretty natural that we'd stayed friends. We'd even double dated with later partners and would frequently complain to each other if relationships were going sideways. More recently things had gotten a little flirty, though we both made it clear we weren't interested in any future dating. I attributed her new forwardness to an increased confidence - she was looking better than ever and judging by the number of guys I'd see sneaking out of the house I wasn't the only one who noticed!

Also around that time another ex I'd kept in touch with had gone through a rough breakup and I was happy to be a sounding board for her. Liz was a high school flame. Our breakup had been a little more contentious (I feel like the first breakup out of high school always is!) but there really was no alternative given we were both going to different schools and a little too horny for our own good. We'd both gotten into new relationships pretty quickly, but while mine had been the fairly casual affair with Chris, hers had been long term and fairly serious. In fact, she told me that aside from a few early hookups, the relationship that just ended and her relationship with me were the only two significant ones she'd been in. She also told me her ex had been about the most vanilla guy imaginable. Sure they had sex, but always missionary with the lights off and only ever to the point where he came. She even told me she hadn't had anyone go down on her since me, which I found shocking. Certainly neither of us had really known what we were doing sexually when we dated, but she'd always struck me as a pretty sex-positive girl and very open to exploring, so the fact that she'd been stuck in such a boring relationship for most of college was really surprising.

So all that background aside, it's Friday morning and Kate is about to head for home after visiting for the week. It'd been the usual sort of visit - half fun, half fighting - so her leaving came with mixed emotions. This morning in particular was emblematic of the relationship. As usual we'd gone to bed nude, and I'd woken up first and decided to wake her up with an orgasm. I slowly move under the covers, feeling her legs and kissing the insides of her thighs. Kate moans slightly and spreads her legs, a half-awake state I'm familiar with. My access to her pussy now unimpeded, I take my time kissing the outside of her pussy before sliding my tongue inside her labia and up and down her warm and increasingly wet slit.

After a few strokes with my tongue as deep as I can into her pussy I focus my oral attention on her clit and slide first one, then two fingers into her. Her breathing changes and I know she's more awake now as I redouble my efforts, my fingers curled to massage her g-spot while my tongue flicks her clit. My fingers and face are getting soaked and, as confirmation that I'm bringing her close, she grabs a pillow and covers her face. Despite this her moans are pretty damn loud, to the point where I know my housemates have a good chance of hearing. I feel her clench and she gives an especially long, loud moan as her pussy pulses around my fingers and wetness gushes from her. I'm rock hard and incredibly turned on, but as I slowly remove my fingers and start climbing up higher on the bed to fuck her, her alarm goes off.

"Oh fuck, I'm gonna be late!"

"Kate, what the hell? Another ten minutes won't kill you right?"

"Sorry babe, I need a quick shower and then I can't be late. You know my folks are expecting me and if I miss this bus the next one isn't til two hours later. And besides, you got off twice last night!"

She's not wrong, but I'm sure not happy, especially cause I know she's built in at least 45min of spare time. In any case, she jumps in the shower, taking way longer than I think necessary, then I drive her to the station. Even with the long ass shower she makes it with ten minutes to spare, which doesn't really improve my mood. I see her off then drive back to the house. Chris and Mike, one of our other roommates, is in the living room when I get back.

"Sounds like you had fun this morning!" Chris greets me with.

"Ugh, well, one of us did", is my reply.

"Damn dude, sorry to hear that", says Mike. He's probably the least adventurous of the four of us roommates and has a long-term girlfriend, but understands blue balls as well as anyone and has never seemed to have an issue with tolerating the noises coming from any of our rooms. Chris gives me a look which I didn't quite understand but seems mildly suggestive, though her face returns to neutral before I can figure it out.

The three of us chat for a little longer, Mike telling us about his plans for the weekend taking his girlfriend to the beach, then I shower and go to my only class of the day. It's a boring lecture in a big auditorium-style hall and I quit taking notes pretty early and instead end up chatting with Liz. She's killing time before her shift starts - doing campus security for her college that's about an hour away from mine - and naturally we get to chatting about our love lives. I give her the overview of that morning, then make the mistake of telling her I'm stuck in a lecture.

[Wait... ur telling me she left u high and dry and now ur in class... did you at least jerk off before u went?], was Liz's oh-so-helpful message.

>>>>>[Nope, but I sure wish I had]

[What're u wearing?] Not the most common question from a girl to a guy, but Liz has always been an interesting one.

>>>>>[Boring stuff. Chino shorts, a tshirt, and flip flops.]

[Underwear?]

>>>>>[Nah, u know me, unless it's sports or something fancy I don't really bother]

[Ur the height of class as ever Josh. And u know that's dangerous too]

>>>>>[Lol as long as I'm careful when zipping up nothing bad happens]

[Not like that! Isn't it obvious when u get a hard on when u aren't wearing undies?]

I didn't have an immediate answer to that and paused. Sure it was true that there'd been a handful of occasions where I'd been commando on campus and gotten hard, but usually it subsided quickly or else it was somewhat intentional and semi-private. I hadn't really encountered the lecture hall boner yet. Liz is typing, and then when her chat arrives I nearly let out an audible gasp. See, Liz knows I have a particular thing for a catholic school girl look, especially since I'd made a point of telling her how good she looked in her most recent Halloween costume (which apparently her ex told her made him uncomfortable).

[Dangerous now?] The picture that arrives is of Liz, in her apartment kitchen, sitting backwards and straddling a chair wearing what I recognize as her halloween costume but with modifications. While what she wore out was long enough that no one would have thought twice about it being inappropriate, her plaid skirt is now so rolled at the waistband that it looks more like a belt that a skirt. I see zero evidence of panties, which, if correct, would have to mean her ass and pussy are directly on the chair seat. And she's definitely not wearing a bra and her button down shirt, tied just below her tits to show off her midriff, does nothing to hide her nipples. Fortunately I'm seated near the back of the lecture hall with no one behind me, both because that way no one else can see my computer screen but also because I immediately get a raging hard on.

>>>>>[Damn girl! U gotta warn me before u send shit like that!]

>>>>>[Also, holy fuck r u hot... is that from halloween?]

[Hehe told u it was dangerous. And yes but I decided to try to jazz em up a bit today. Some end of school parties coming up so I'm trying a few things on. I like this way of wearing em better, don't u?]

>>>>>[I sure as fuck do. I don't think I'd be able to control myself around u if ur wearing that!]

The professor starts to wrap up the lecture, which my brain just barely comprehends. I tell Liz I need to get off (yes, jokes ensue) and between my laptop and some serious concentration manage to get out of the lecture hall without my situation being too obvious. Fortunately there's no one home when I get there, since the image of Liz stays firmly rooted in my mind the whole drive back and my cock stays similarly firm. Safely behind the closed door of my room I drop my shorts and boot my laptop up. Liz is still online.

>>>>>[Fuck girl... I've literally been hard the entire time since u sent that pic. What were u thinking!?!?]

[You mean innocent little me? I was just thinking how much uv been telling me I've been missing out with my lame-ass ex.. and since Kate left u unsatisfied this morning how u could do with a little help ;-)] Liz and I have been pretty flirty before, but this represents a whole new level of forwardness from her. That said, I've definitely opened that particular door pretty wide in some prior conversations.

>>>>>[That's very true and I sure could... but what'r u thinking?]

[Honestly I'm horny as fuck and if I didn't have work I'd tell u to come over now. Would u mind coming over late? Uv been telling me how fucking good ur tongue is and I think it's about time u put ur mouth where my pussy is]

>>>>>[I sure like that spin on the expression! And sure, happy to come over late. Just tell me the time... and that ull be wearing that skirt!]

Her shift ends a midnight and we settle on me coming over at 1am. She tells me she'll definitely wear the outfit as long as I promise to wear what I was in during my lecture. I try to get some sleep and manage to nap a bit, but I'm a horny mess and really too turned on to sleep properly. I manage not to jerk off and cum, but it's definitely a struggle! I'm vaguely aware of Mike packing up and heading out with his girlfriend and similarly hear Chris getting ready and going out to the bars with some friends. Around midnight my alarm rings and I start getting ready in the empty house. Quick shower and prep, and I pull on the same shorts, shirt, and sandals with no underwear as requested. I send Liz a quick text that I'm on my way and make the 30 minute drive to her place.

I'm practically jittery with anticipation and hormones as I approach Liz's apartment. It's a good thing she's told me her roommate was definitely out for the night or I'd have been desperately trying, and trying in vain, to hide the tent in my shorts. As it is I'm just grateful there isn't an obvious pre-cum wet spot as I ring the doorbell. The door opens and frames Liz. She's wearing the outfit as promised: hair in long pigtails, heavy eye makeup and lip gloss, her barely-there button down top tight and see-through across her small but perky tits, plaid skirt just as short as before and still no sign of panties. To cap it all she's now added chunky schoolgirl heels and white over the knee socks.

"Well I'm glad to see you too!" she says, looking very pointedly at the strained crotch of my shorts. "I told you that was dangerous. Why don't you come in and put it to good use?"

She spins around and heads up the stairs of the split-foyer apartment. I shut and lock the door behind me while keeping my eyes fully focused on Liz's ascending ass. She's giving me quite a show, arching her back and proving conclusively that I was correct in my assumption about her total lack of panties. I mostly just stare while she gets to the top floor, then leaving my flip flops at the door I hurry up to find her in the kitchen. As I enter she's just finishing what looks like was a long swig of Jameson right out of the bottle.

"I know schoolgirls aren't supposed to drink... I guess you'll have to punish me later" she says in a pouty voice giving her most innocent look. I step towards her and pull the bottle from her hand while wrapping my arm around her back and pulling her towards me.

"They definitely aren't, but they also aren't supposed to wear whorish makeup or skirts that show of their cunts. So clearly some lessons are in order." I grip the back of her head and push it towards mine as I forcibly make out with her. She gives a little gasp but her tongue swirls around mine and when I release her head she keeps her lips locked with me. I move my hand from her head to grope her ass, easily accessible below the skimpy fabric of her skirt. Her hands are on the waistband of my shorts, and her thin fingers make quick work of the button and zipper. My shorts crash to the ground and my cock finally springs free. Liz puts both hands on it and immediately sinks to her knees ending our violent makeout session. I take a few chugs from the Jameson bottle as she slides her sticky thick lips over the head of my cock and down my shaft. Knowing her preference I'd been careful to give my cock and balls a thorough shave and the rest of my crotch a good trim. She slides back up and off my cock, spits a massive wad in her hand and gives my cock a stroke. I feel the spit running down my scrotum already as she keeps her one hand at the base of my cock, shifts her other to massage my swollen balls, and starts to truly suck and lick my cock.

I take my shirt off, but otherwise I'm pretty mesmerized by the attention Liz is giving my dick, moaning and grunting as she attends to it. I know there's no way I'll last very long like this, but I also know that with as horny as I am it won't be long before I'm ready to go again. I'd like to say it's a conscious decision to let her keep blowing me til I cum, but honestly at that point my brain was past the point of rational thought. While a true deepthroat wasn't in Liz's repertoire she was making up for it in enthusiasm, her tongue sliding under my foreskin and flicking the underside of the head of my cock, then periodically wiping my spit-soaked member all over her overly made up face. This not only feels amazing but has the added benefit of making her cheap cosmetics run. Now instead of an innocent schoolgirl she looks more like a cheap street hooker. She strokes my cock a few more times replacing her mouth around my head and sucking like she's drinking a thick milkshake. Between the sensation, brazenly slutty attitude, and now the look of her destroyed makeup I just can't hold out any longer.

"God damn girl I'm cumming!" Credit to her, she gives my balls a small tug, keeps pumping her hand on my shaft, and plants her mouth around my cock as I erupt into her, repeatedly pulsing as my balls empty. It's been over 24hrs since I came last, and I'm a pretty heavy cummer. I feel her swallow once but I'm still pushing out semen. Finally my orgasm subsides and I look down at her. She gives me a grin and opens her mouth wide to show me she still has a full mouth. I pull her to her feet and we make out again, this time swapping spit and fresh cum. Some gets swallowed but a lot ends up dripping down our chins and we're both a bit of a mess when we finally stop kissing.

Liz looks slightly disappointed which confuses me.

"Sorry, I didn't meant to make you cum so quickly. I was hoping you'd stay longer."

"What, you thought I was gonna cum and leave? We're just getting started!" She immediately perks up and I realize that for the past few years she's gotten used to a very poor standard of sex. "I'm already half hard again, and plus I'm dying to taste that pussy you've been flaunting all day. You want to get eaten out in the kitchen or your bedroom?"

"Oh fuck. Yes please! Um, how about bedroom?"

"Well lead on. But first, since you now look like a whore more than a schoolgirl, you want another drink?" I hand her the bottle, she takes a swig then hands it back to me and I do the same before leaving it on the kitchen counter. She leads me to the only bedroom on this floor and gets on the bed, heels and all, kneeling on it and facing me.

"You never told you what you thought of the outfit!" she half exclaims, half asks.

I find the light switch, which happens to be a dimmer, and turn it something like 2/3rds on. "Well first, there's no way in hell I was gonna be able to give it a proper appraisal in the pitch black like that. You know I like to see who I'm doing! And secondly I wanted to talk to you about that. It looks fucking hot as hell, but I'd say there's a 100% chance some part of it gets ripped to shreds if you keep it on once we start fucking. It'll be sexy as fuck if you keep it on, but I totally understand if you wanna take it off."

"Josh, if I was wearing panties I just woulda flooded them. I'm keeping it on." She gives a slutty smirk, accentuated by her now whorish makeup.

"Well good! And now I think it's time I see just how flooded you woulda gotten!" I quickly advance to the bed and shove her backwards, one hand in the center of her chest forcing her hard into the mattress. From the kneeling position she was in her legs are spread wide, calves folded underneath her thighs. I grab just above her knees and pull upwards, freeing her lower legs and also flipping the front of her skirt up exposing her entire crotch. She gives a short shriek at this rough treatment, then immediately moans as I dive face first onto her pussy. She was definitely not exaggerating at all and is already thoroughly soaked, so I waste no time in spreading her pussy lips with the fingers on one hand, my tongue probing the folds of her pussy for her clit, while sliding two fingers from my other hand straight into her. In the empty apartment Liz doesn't bother with trying to stay quiet, and an unintelligible stream of guttural noises punctuated with gutter language come from her mouth.

Most of the time when we'd hooked up in the past we'd needed to stay quiet for one reason or another, so it's a bonus to find she's a screamer. I lose complete track of time as my head stays buried in her snatch, my tongue relentlessly massaging her clit while my fingers probe her sopping pussy. She's alternately grabbing fistfuls of the sheets and pressing my head into her pelvis, my chin now absolutely drenched and dripping with her juices. She seems receptive so I slide a third finger into her and her moaning kicks up a notch. I suspect I'm in for an impressive explosion as I give my ex an experience she hasn't had for quite some time, and sure enough the force of my three fingers on the inner cavity of her cunt has her at the precipice. A brief silence and then:

"OH FUCK FUCK FUCK FUCK FUCK YESSSS YOU FUCKER YES!" For a small girl, Liz lets out one hell of a bellow while simultaneously spaying a jet of squirt into my face like a fucking fire hose. I slurp down some of it while holding a mouthful, but ultimately that's a tiny portion of the overall volume which utterly drenches me, all of Liz's body from the waist down, the bed, and a good portion of her room as well. She's panting and gasping for breath, looking slightly surprised at the carnage she's just caused. I couldn't be happier and am even more turned on than earlier in the night, if that's possible. I take advantage of her momentary surprise to spit the mouthful of squirt strategically onto her chest, wet spots turning her shirt truly see through over her tits.