You're Dumped (Tri)

The latest incarnation in the crazy shenanigans that is the You're Dumped saga, in which ex-boyfriends are dressed up as girls and exposed to the other side of the equation.

Troy had been trying to get with his old girlfriend Sanka for months, but she had made it very clear that she never wanted to have anything to do with him after the affair.  He thought with time and distance she’d eventually warm up again, but she barely acknowledged his existence.  Rumor had it that she had a no boyfriend, but he never met him.  He’d finally gotten used to the idea that she was never going to take him back (or give him a booty call), when one day, while he was on his way home from work, he got a voicemail from her.  He listened to it once, then twice, and when he got home away from the hustle and noise of traffic, he listened to it a third time, just to make sure he was hearing it correctly.

“Hey, Troy, this is Sanka.  I know I said I didn’t want to ever see you again… and I’m standing by that, but, I have a favor to ask of you.  I showed one of my girlfriends your picture and she told me she wanted to meet up with you, no matter what I said.  So, I don’t know if you’re interested… she is pretty cute, and she seems like your type.  I figured I’d make a show of peace, but I just want to be clear: we’re over, still.  Anyway, if you’re interested in a hookup, just text me and I’ll send you all the details.”

In the silence of his apartment, Troy was stunned to confirm that he’d heard what he’d heard.  Sanka had always been pretty jealous, and he couldn’t believe that she’d be willing to set him up with one of her friends.   He guessed it was her way of showing, definitively, that she was over him.  That rustled him a bit, but the idea that a cute friend of hers was hot for him was more than enough of tantalizing detail to push that from his mind.  He responded almost immediately.

“who/where/when/how?  i’m down for that.  how r u babe?”

He put his phone down, still in shock, but with a creeping sense of smugness that was overriding his reason.  He grabbed a beer out of the fridge, took off his shirt, and sat down on the sofa.  As soon as he’d settled comfortably, he heard the buzzing of the vibrating phone on the kitchen table, and sighed, exasperated.  With a regretful grunt, he kicked his legs out and got to his feet again, walking over to the buzzing, glowing nuisance.  When he picked it up, he saw that she’d already fired off a lengthy response.   His curiosity piqued.

“I’m fine.  Her name’s Natalie.  She wanted to meet you ASAP, somewhere neutral.  I’m going to be out all day tomorrow, so I told her you two could meet at my place, if you don’t-”

The text ended, and he went on to the next one.

“-make a mess.  I’m going to be honest; Natalie’s sort of a freak.  I wouldn’t be surprised if she ‘ambushed’ you.  Not anything dangerous, I mean.  Just, you know, she’s into-“

He clicked to the next text, his pulse rising.

“-self-bondage… and blind hook-ups…  and she has… ‘coercion’ fantasies.  Hopefully you’re down with all that?  If you are, I’m sure you’ll both have a good time.  Especially since Nat likes it the wrong way.”

His eyes had widened more and more with each word.  When he reached the end, he checked to see if there was another text, but nothing came.  Tentatively, he texted her back.

“what u mean?”

He waited, phone in hand, for the reply.  The phone vibrated, and he clicked into the text.

“How do I put it politely… well, I guess you could say she likes it up the ass.  She’s sort of an anal queen.  A buttwhore, you could say.  If that’s fine with you…  8:30 tomorrow at my place.  She’ll be waiting.”

He swallowed, hard.  It wasn’t the only thing that was hard.  He dreamt that night of Natalie, the cute, bouncy co-ed that liked it in her shitpipe, and all was good with the world.

When he got to Sanka’s place the next day, he knocked on her front door, but there was no answer.  He was about to ring the bell when he noticed the door was slightly ajar, so he slipped inside, closing it behind him.  Her house was dark, and there didn’t seem to be anyone around… until he heard heels clacking on the floor in the living room.  Slowly, quietly, he took each step, trying to find the source of the noise without alerting them to his presence.  When he came into the room, what he saw nearly made him tear his pants in half.  There was, presumably Natalie, her hands tied up and her legs forced open, facing away from him, almost naked.  On the coffee table next to her was a box whose purpose was clear.  It said, in bold font, “ANAL LUBE.”

---

Nathaniel arrived promptly at 6; he didn’t like to keep Sanka waiting.  When she told him she was finally acquiescing to his request (more like his begging) to bring in one of her friends, he was… eager, to say the least.  When she brought him to her bedroom and he saw the lingerie laid out on the bed, including thigh-high stockings and high heels, he got even more excited.  When she told him that he was going to be the one wearing it… he felt a flush of embarrassment, but nodded, knowing it was the price of admission.  If two girls wanted to play dress up with him for the night, he wasn’t going to turn that offer down, even if it did make him self-conscious. 

She dressed him, dolled him up with make-up, tied up his hair, and even gave it a little temporary Halloween dyejob, treating the ends with fire-engine red.   It was really hard for him to walk in the heels, so he wobbled after her into the living room, where she revealed her manacles.  She had him hold his hands out in front of him, and she clasped the manacles shut.  Climbing up onto a footstool, she shackled him to the ceiling via a hook that he’d never seen before.  His anxiety only grew when she produced another bondage implement – a spreader bar, which she locked to his heels, forcing his legs apart.  He was about to voice his concern when she affixed the tape to his lips.

Sanka reached up to his hips, and carefully rolled down the panties that Nat was wearing over his rear, down to his thighs.  She slapped something onto his cheek, and then slowly pulled it off, and though he couldn’t see it, he recognized it as a temporary tattoo.  Then, nonchalantly, she walked away from him.  She rustled through her handbag, and then placed something on coffee table, and then, without warning, she slung her bag over her shoulder and walked away, her heels clicking on the hardwood floor, until the sound faded entirely.  Nat waited… but she didn’t return.  Then, the first inkling of panic set in.

He looked over his shoulder frantically to try and analyze the situation.  Sanka was gone, and he seemed alone… if her friend was coming over, she was definitely going to be playing on his domination fetish, but somehow, being dressed like a ho with a star tattoo on her butt left him uneasy.  He kept surveying the situation, something he had failed to do while Sanka was leading him around on a leash, and eventually he spotted it.

On the corner table, sitting hidden in plain sight, was a generic looking pharmacy box.  On it, in bright yellow lettering, though difficult to make out in the dark, were the words in bolded font, “ANAL LUBE”.  He stared at in shock, his heart beating fast in his chest, his breaths coming uneven, his anus tightening. 

He couldn’t wriggle free of the restraints at all, and he already heard footsteps.  His mind raced.  One after another, he imagined his girlfriend’s sex toys, their shape, texture, and size.  He didn’t know which one of them Sanka’s friend was going to be introducing to his hindquarters, but he wanted to mentally prepare himself for any of them.   The long, slender dildo, the studded one, the curvy one with the extra bit on it, or, of course, the plugs.  Of course, it was entirely possible that Sanka’s friend was bringing her own silicon fun, and Sanka had just thoughtfully left her the boyfriend-emasculating jelly she would need to, well, emasculate her boyfriend.  He imagined a blonde knockout wearing a big purple strap-on, gripping his thighs and going to town, and he had to admit, while the prospect was terrifying, and his ass wouldn’t be able to take it, there were worse things you can do to pass the time.  It just so happened that, once the footsteps got closer, he got to see his first glimpses of one of them.

Sanka’s friend was blond, alright, and stacked, but there was only one problem.  Sanka’s friend was a guy.  A [i]big[/i] guy.  Nat hoped beyond hope that he was just a meter-reader or a pizza delivery guy who walked in on an embarrassing scene, but when Nat saw the look on his face, and the bulge in his crotch, those hopes were dashed against the rocks of reality.

---

Troy used two fingers to apply the lube between Natalie’s cheeks, who in turn did her very best to try and communicate… something to him, urgently.  Those communications became more urgent when Troy politely introduced a finger into previously uncharted territory to lube the interior, a necessary and vital step in preparation for the much-larger non-finger he was planning to introduce into Natalie’s unfortunate rear.  Natalie groaned into her gag as he swiveled his finger inside as deep as it could go, to get lube all over Natalie’s alternative (substitute) lovehole.  Recognizing that, at present, she was way too tight, he helpfully inserted another finger, although Natalie didn’t appreciate the thoughtfulness, nor the [i]fullness[/i].   His attempts at foreplay (and preparing Nat’s tight ass for the uncomfortable stretching it was about to receive) made Nat writhe, which he took as a good sign.    He thought about giving her a bit of a hand up front, but then decided against it.  If she wanted to get off with her ass, he was going to give her what she wanted, even if she probably should have asked Sanka if Troy was the man for the job.  Not that he couldn’t give it good, but, he knew that she might regret it after.

Satisfied that her pooper had been sufficiently prepped, he pulled his fingers out with a wet schlopping noise.  Natalie’s hole closed again, slightly leaking the lube that he’d carefully greased up her pipe with.  He debated pulling off her tape gag and having her clean off his fingers, but wasn’t sure if she’d be into that and, more importantly, he wanted to get to the main event as quickly as possible.  Just to be sure that she had all the prepping she needed, he grabbed the tube, pressed the tip slightly into her recently frisked asshole, and squeezed it as hard as he could, filling her butt up with the slimy goo.  When he stood up and backed away to see her reaction, she shivered, and some more lube leaked out, down her cheek, and thigh, and some onto the floor.  So much for not making a mess.  Troy put the lubetube down for a second, and unfastened his belt.   When his pants dropped to the floor, Natalie’s eyes once again went wide.

---

Still recovering from having his bowels irrigated by anal lube (and still feeling the slippery mess in there), he heard a belt buckle, and frantically turned to look.  Sanka’s friend’s pants hit the floor, along with his tightey whities.  And then, in the very same mental picture that was sure to haunt his nightmares for days to come, he saw both the dripping bottle of lube and the dripping, fully erect, cock.  His futile wriggling got more intense, and his sphincter automatically snapped shut, his pucker tightening up as much as it could given that he’d just been fingerbanged.   It looked like a monster.  When Sanka’s friend walked closer, he couldn’t see it anymore, but he could still sense its presence.   When he put his arms around Nat’s waist, he felt it between his cheeks, hot and rigid.  Troy’s hands went down his abdomen, towards his pubic region, but didn’t go far enough to reveal Sanka’s trickery.  Nat trembled, in teeth-clenching anticipation.

He could feel and see the one hand on his hip, but he didn’t have to see where his other hand had gone to know where it was.  He could hear the slick noise as it prepped his girlfriend’s impromptu marital aide, and there was no doubt  he was going to use that hand to guide his beef missile where it was going, which, given the tape gag, the wrist-bindings and the spreader bar, was somewhere no man had gone before.  Somewhere snug, specifically.

With his hips wiggling as best they could, the big lunk had a hard time finding his mark, although the occasional near-miss meant that Nat knew what it felt like to have a cock tip requesting permission to enter into paradise, where “paradise” here was played by Nat’s endangered rear entrance.  Eventually, Troy got tired of the game, and slapped “her” ass hard enough to make Nat see stars, which got the unfortunate butt stunned still for a second, long enough for Troy to get the positioning right, and long enough for him to try and apply pressure up towards Nat’s greased chute.

He could feel his sphincter’s resistance giving way, and panicked.  Rationally, he knew unless men burst through the door with guns at that very moment, it was going to happen.  A mistake of really embarrassing proportion was about to be made.  He wanted to warn Troy that he was barking up the wrong tree, that he was shoving his sausage in a fellow sausage-owner, but with the gag in place, all he could say was…

“Mmf… mmf... mmmf!  MMMFGGHHH…”

At a certain point, enough resistance gave way to lubrication, insistence and exhaustion, and something lurched about half an inch forward.  That “thing,” of course, was the glans of a man’s penis, and “forward” here meant “into,” specifically “into Nat’s well-lubed, well-prepped, unwilling ass.”  Nat’s eyes crossed a bit, and his eyebrows twitched nervously, and he let out an exasperated half-sigh, half-groan that seemed to say a combination of “oof, that’s a big one,” and “you moron, that’s my asshole!  You just put your [i]cock[/i] up my [i]asshole[/i]!”

He started to tremble and wiggle his hips to either dislodge or relocate the intruder more comfortably.  He hung his head, and steeled himself.  It wasn’t as bad as he thought it would be, but it still itched, burned, and already felt a little sore, stretching open as wide as it was.   The psychological aspect he was wisely avoiding by focusing his mental energy on calling Troy various variations of “big-dicked ignoramus.”  Shame and anger competed in his mind, with at least part of that anger going towards his back-stabbing girlfriend (although the literal back-stabber got his fair share).    If this was her idea of a joke, she was insane; if she thought he wanted this…  she was still crazy, and a bitch.  He’d toyed with the idea, but the reality wasn’t exactly going how he wanted, though knowing Troy was as duped as he was made it easier to cope.   That, and his girlfriend’s panties had gotten cramped. 

Troy took his hand off of his big guy, now that it had been properly introduced to Natalie’s ass, and placed it on Natalie’s other hip.  He licked his lip, and let Nat adjust to his girth, because she had to adjust to that before he wrecked her with his length.  If this girl was into deep anal dicking, he was going to give it to her, and he was going to make sure she was going to remember how big, long and hard he was.  Still, he knew to take baby steps.  She had definitely never had one as big as his before, by her reaction, and the fact that she was plugged perfectly tight.   She had a nice ass, but it was that tight hole that was going to work him over. 

Nat looked over his shoulder to assess the danger.  With both hands on his hips, there was nothing holding his widowmaker in place but ‘Natalie’s’ utterly perplexed hole.   He couldn’t see the part that had settled in between his cheeks, but the tube of meat leading back to his body, the unburied portion connecting the two of them, made Nat’s eyes go wide in terror.   He looked at Troy’s face, but turned away when he saw his grin, and stared straight ahead, and got ready to defend against Troy’s attack.

Troy took that as readiness, gripped tight for a second to warn her he was about to continue, and then urged his own hips forward, making Nat moan anal frustration, not lust, as Troy interpreted it, into the gag, his face flushing red with embarrassment as he was inadvertently losing his anal virginity inch by inch. 

The next few minutes consisted of shoving and groaning, as a virgin ass gave more and more ground inevitably to a turgid, eager cock.  Drool started to seep through the gag, as Nat had difficulty keeping his mouth closed while Troy kept his rear hole open.   Troy either gripped “her” hips or groped “her” buttcheeks, placing his hands flat against them and shifting them around his embedded, rock-hard schlong, or pulling them apart so that he could see his progress in real time, her too-tight hole accepting him bit by bit.  When he did that, Nat could feel every bump on it as it sunk inside, and much preferred he kept his hands on his hips or even shoulders if it meant less ass-grabbing.  Nat knew the trick to anal was to push out like you’re using the bathroom, and made good use of that, but even with that, the lube, and the forced leg-spreading, Troy was too big comfort, although not too big for penetration.    Unfortunately, he had more in common at present with the princess from the Princess and the Pea story than Goldilocks.  As more and more of it invaded her hole, she went cross-eyed and started to sweat, unable to cope.  When Troy started to thrust in and out a bit, her eyes went wide, and then he suddenly lurched forward.

That proved too much for Nat, who managed to kick back at Troy a bit, which made him retract a few inches, which was a relief.  He put more lube on the part of his cock that had recently vacated Natalie’s hole, and then started to push forward again.  Realizing it was still too much, Nat pushed back at him with his butt, a counterattack that proved ill-advised when Troy drove it all the way home in response, all the way up Natalie’s guts.

It made a squishing noise as it utterly filled Nat’s bowels, which Nat did not hear over their own eye-rolling groan.  It was such a sudden butt-filling that Natalie didn’t have time to notch it off their bucket list before they felt the heat of Troy’s body pressed up against their girly derriere.   They continued to groan hoarsely as Troy tapped their hips lightly against their cheeks, barely moving the actual hard, dick-shaped mass that had displaced a large portion of Nat’s rectum.  Nat’s sphincter sucked on the base, aching, but like its owner, submissive.   All of Natalie’s other anal rings gripped tightly onto the invading, tremendous mass, clearly defining and adhering to its shape, measuring its rigidity and sheer hardness in terms of constipated aching.   There was a big, hard cock in Natalie’s butt, and it was pulsing in the cramped space that it so enjoyed, even though it had absolutely no spare room to do so.  Eventually, Nat managed to turn their constant groan into the occasional frustrated high-pitched grunt, and the first part of their anal ordeal hit a denouement, as their big, dumb anal penetrator started to withdraw his unit bit by bit so he could get to the fun part.

---

Sanka sat wrapped in blankets, a warm cup of cocoa in her hands, as she stared, transfixed, at her computer.  It was cold in the basement, and felt even colder with the lights off, but what she saw warmed her cold, black little heart.  It had been all over the news: the crazy girlfriend that let a minor league baseball team run a train on her boyfriend, and then ended up turning herself in to the police.  Then the copycat, who disappeared after she staged a gangbang for her boyfriend, who she dressed up in ‘alt-girl’ attire for some reason that made sense only to her.  Her last known whereabouts were a few miles from the Mexican border.  Sanka’s plan wasn’t nearly as evil, she told herself.  There was one (1) guy, well, two, if you counted the emasculated sissy that was her current boyfriend.  Her boyfriend had expressed interest in bringing in a relief pitcher, and hadn’t objected too loudly when she suggested it could be a man.  He’d been so insistent and passive aggressive about it, and her old boyfriend had been so insistent and aggressive-aggressive about hooking up with her again, she thought it was only appropriate that the two of them worked out their aggression in their respective roles: Troy in the aggressive, ignorant position, his favorite one, and “Natalie” in the passive, bitchy position, which was his.  And would it be so wrong to broadcast the whole thing via webcam?  Of course not.  Would it be so wrong to use multiple cameras, hidden around the living room?  She didn’t think so.

The other people subscribed to the webcast were a mixed bunch.  Some were aware of the duplicitous nature of the act, and they had a betting game going.  The odds for ‘finds out the secret, leaves in disgust’ were high, the odds for ‘finds out the secret, goes ahead anyway’ were slightly lower, and the odds for ‘dumbass doesn’t notice, plugs his ex’s boyfriend’s ass for fifteen minutes, leaves a steaming load in what he thinks is a girl’s butt’ were low.  It definitely looked like that camp was going to win their 2:1.  Troy didn’t seem to have the slightest inclination that anything was wrong, even though, from the underneath camera, the truth was obvious.

From that vantage point, they could see Nat’s perineum ending on one side with no va-jay-jay in sight and with the other side ending in an anus clinging tightly to a slick, invading tail, which might have been difficult to discern if it weren’t for the vein running through it or the occasional moment where it came out enough for the viewers at home to get a brief view of the underside of its glans, pretty perfect proof of it being a penis insistently invading innards, namely Troy’s. That camera’s audio manages to pick up the squishing (on the way in) and sucking (on the way out) sounds of sex, the slipping, sliding, the sucking and slurping of a sphincter really, really reluctant to release a really, really big rod.  At its shallowest, it was a fearsome sight, a long, thick shaft, ending in a rounded point, slightly penetrating a tight pucker, with nothing stopping it from penetrating deeper, and deeper, until it plumbed the depths entire, pushing aside soft innards in the way.   At its deepest, it looked like a horse breeding its mare, a forceful intrusion that almost looked like magic:   where did the big penis go?  Of course, on the other camera synced up, the grunting of the recipient made it obvious: up the butt, of course.  At that deepest intercourse, the testicles of the massively endowed intruder came perilously close to a similar, if slightly smaller structure, on the receiver, but very rarely touched.  If the intruder noticed, it’s doubtful he could hazard a guess as to what that was, or that he even cared at this point.

He stuffed his hand under her bra, and felt at her smooth, hairless, feminine chest.   He didn’t let the fact that she was incredibly flat-chested bother him; she had more than enough where it counted.   She moaned when he felt up her body, which encouraged him do it more.

Nat, of course, was moaning in shock more than anything.    Having Troy explore his body and, apparently, approving of how soft and feminine it was would have embarrassing in any circumstance, even if he wasn’t, at the time, rummaging through his backdoor, hands-free. That he [i]was[/i] giving Nat a hands-free anal excavation while feeling him up should have been the absolute nadir, but he managed to up the ante (or lower the nadir) a moment later when he grabbed both of Natalie’s wrists, which were already tied overhead, and started to press into Natalie with each thrust, further cementing the notion that, for what the two of them were doing together, they didn’t need to use their hands.  What Troy didn’t realize was that, below the waist, he was fucking Natalie’s ass, and “Natalie” was stretching the fabric of their panties, also without hands, because of Troy’s sans-manos prostate stimulation.  All he knew was that he had this slut’s hands above her head, and down south he was giving it to her good.

Upping the humiliation was that, being unaccustomed to sex standing up (much less wearing heels), Nat’s calves were getting too sore to use, which wasn’t helped at all by being forced to stand on tippy-toes.  This meant holding themselves up with their arm restraints… which their arms quickly became too tired to do, as well.   Thus, the only recourse they had was to let themselves go slack… which had the unfortunate added effect of making it look like they were bending over for more.    Not that they had a choice whether they got more or not, but they didn’t have to bend over for it.  Of course, even when they managed to stand up straight again for a while, that just put them in a different “ready to be ass-fucked” pose, so maybe the bigger issue was just the fact that their poor butt was in use, carnally, for some stupid dude with a [i]big[/i] cock’s jollies. 

Maybe that was the [i]most[/i] humiliating thing, now that he thought about it: while the big oaf was taking his temperature rectally, even though both of his hands were pre-occupied with fondling his hips and “breasts,” (which was enough of a gutpunch to his masculinity; taking someone’s man-meat as a suppository), he was busy measuring the thermometer in the most embarrassing way possible.  He had gotten an eyeful of it at the start, and his heart had sunk into his stomach (even moreso when the big palooka seemed to like the way the “girl’s” eyes went wide at the sight of it), but he was sure it had been a trick of perspective. Maybe cocks look bigger when they’re rigid, dripping precum, and sitting next to a box of anal lube, while you’re facing the other direction with your legs forcibly spread and your hands tied helplessly above you?  Particularly when they take a step forward, and it wobbles, and you realize that it’s that big [i]for you[/i]?  Still, he couldn’t deny that even if only “looked” like Godzilla then, it definitely [i]felt[/i] like a monster when it was up his cutey-patootey.   Halfway in it was cross-eyed constipation, and all the way in it was both a nightmare and a very real rectum full of hot sweaty dick.  It was the latter that was weighing on his soul, because there was no way anyone’s rectum would be totally filled by [i]his[/i] mystery meat, fistful of Viagra or no.  He was absolutely certain it felt bigger sliding up his virgin chute, but “bigger” there meant “fatter,” and it was the [i]length[/i] he was so fixated on.  Inch by inch it crammed its way into his greased-up billy-butt, and no matter how much he over or under-estimated them, the result was hovering around double digits.  “Double” being the appropriate word that got stuck in his head, where if you reversed the relationship, that word would be “half.”  The guy was bigger than him, height-wise and bulk-wise, but there was no reason the sausage had to match the meathouse, and yet, unless his stretchy funhole wasn’t the right instrument to measure her ex’s meat-popsicle , (or maybe ‘dipstick’ is more appropriate), the hard truth of it was laid bare: his girlfriend was used to a bratwurst, and he was packing a pickle.  And then, to add injury to insult, that very same bratwurst was packing into him, and maybe it wasn’t such a good idea to repeatedly  squeeze it to check it for size, because Meathead Rumproaster had taken it as an invitation (or a dare) to pick up the pace, the intensity, and the dirty talk.  The latter of which Natalie didn’t even really hear (aside from the occasional “bitch” or “ass-slut”) because all he could hear was the sound of hip slapping up against ass and that his fellow tricked boyfriend was fucking his ass [i]way too hard[/i].

That absentminded period of insecurity and curiosity cost him sorely, literally.   He hadn’t noticed that each time he squeezed onto the slowly-spelunking sausage that was porking him between the buns, a spray of precum had been fired off as a warning shot to his bowels that if he didn’t quit it, it was going to assume he really wanted to be a mommy, and it was going to do its very best to make that dream a reality.   In other words, he convinced his unwitting paramour that it was time to party, and build up to a big finish, and so he’d gripped onto the buttslut’s hips and started to drive it deep and fast, which made Nat scream a few muffled protests into his gag and try to wriggle out of it before collapsing, inadvertently sticking a shapely butt back at Troy, proving to his stupid, dull mind that she was “really into it.”  The display was too hot for Troy, who was already at his limit trying to hold back the inevitable cum enema that he was going to give Natalie, due to the combined factors of Natalie’s seeming willingness to give up her (insanely tight) butthole to a stranger, her unrestrained groans of pleasure, and her shapely, plump butt, a winning combination for a girl.  His hips slapped into her fat cheeks and her trampy star sticker over and over again, a wet clapping that understated just how deep she was getting butt-blasted.  He gave her a slap on the star, right on her rear, and she tightened up, so he gave it to her harder.

Of course, he had no way of knowing that he was sodomizing an anal virgin, so his fast-paced anus-obliterating thrusts weren’t caused by malice or sadism, but by the simple, genuinely male desire to give a tight, wet hole the best fucking possible, which meant making sure it knew it was being fucked, and maybe leaving it in a state afterward that anyone could tell it had been fucked.   With the amount of lube involved, the only thing really resisting his efforts were Natalie’s overtaxed anal rings, which had just about given up, which was fortunate for Nat in that it meant he wasn’t painfully resisting being butt-pumped, but was unfortunate for Nat because it meant he was being butt-pumped at a rate and depth that were normally reserved for anal queens, not first-timers.  Of course, it was also unfortunate for Nat in that he was a straight guy, and Troy’s well-meaning anally amorous affections were as unwanted as they were uninvited as they were utterly uncomfortable, which, to put it mildly, was “very” on all counts.  Still, when life gives you a big cock up the ass, you make big-cock-up-the-ass-ade, whether you want to or not, and Nat was miserably aware of how close he was to making that hetero butt-sex faux pas known as “jizzing semen while taking it in the ass,” something that was probably far from being on Troy’s radar as a possible outcome of his vigorous “non-vaginal” virgin-busting.  He was pumping that ass hard because he thought she wanted it hard, and because her tight, wet, warm hole seemed to be a good place to deposit some DNA, which meant a whole lot of thrusting and not a whole lot of holding-back.   If she wanted a cumload in the hole she shat from, who was he to tell her no?

Natalie cursed Troy for not noticing the banana-shaped protrusion in her panties, and herself for filling out Sanka’s panties with a stiff banana.  Even worse, the pressure was building, and Natalie knew it was only a matter of time before “she” got off on the intense anal stuffing she was receiving, and it didn’t help that Troy’s hands were clapped onto her sensitive ass-cheeks.  He kneaded her butt around his ass-pounding cock, and she got ready to fling the most embarrassing goo of her life, if Troy didn’t shoot off first.  As the rocking and slapping continued, the inevitable happened; Natalie doubled over and moaned hoarsely, and spit a thick load through the stretched-thin membrane of the panties pressed against the tip of his cock.  Natalie feels a tickle as she’s forced to cum against something, and an obstruction in her bowels as her sphincter tightens.  Troy feels her ass clench like a vice, and she shudders through her orgasm, but he can’t possibly see the forward-pointing stain that she produced as semen forced its way through the fabric.

Having inseminated his panties thoroughly, the cream bubbling through and dripping to the floor, Natalie was both exhausted and extremely annoyed when Troy resumed his butt-blasting, not realizing his toy has a refractory period to deal with.

Sanka’s hands worked furiously under her desk.   There was little doubt as to whether Nat’s “coercion” fantasies extended all the way up his colon.   She had worried his fantasy wouldn’t live up to reality, but when the panties frothed over and she could see them dripping, she smirked.  Watching him get off to a random anal stuffing was both hilarious and hot, and she knew she was going to hell.  Unlike the other girls, she didn’t necessarily want to leave him, but doubts he’ll want to stick around with the crazy girl that tricked him into playing Buttfucked Bottom to another guy’s Confused Cock.  She wondered when she was going to break the news to Troy; before or after he bragged about it?  Certainly after he’d finished ravaging his ex’s current boyfriend, and definitely after he’d pumped ‘her’ bowels full of proof-in-the-pudding semen.  Maybe she’d be cryptic about it; tell him he’d missed his evolutionary mark.  That not only had he left his sperm in the wrong hole, said hole (and makeshift sperm tank) belonged to someone with a Y-chromosome.  Even he’d be able to figure that brain teaser out: that he’d butt-stuffed a boy’s booty, that he’d blasted it in boy’s butterhole, basted a boy’s bowels… and that was it, Sanka’s finger-shuffling reached a crescendo and she could barely keep her eyes on the screen as she threw her head back, bit her lip, and trembled even more than her boyfriend currently was.

Even though he’d already cum once, Nat could feel it building again.  And even though his cock was still drooping down, half-erect, it seemed as if it wouldn’t even get all the way back up before he let it fly again.  Now that he wasn’t that hard, the panties pushed it down, and so when his mind went blank, and his head was full of fluff,  the second load drips out of his forced open eye into the panties, forming a pool.     Getting buttfucked and jizzing through his girlfriend’s panties was bad enough, but blowing a load into her panties like a diaper was just embarrassing.

He could feel his backdoor spasming around Troy as he dripped milk into his panties, and so could Troy.  With an embarrassingly loud moan, he started to cum up Nat’s ass, into her belly, without even realizing what was happening for the second time that evening.  Feeling the sudden gush, Natalie was flooded inside with semen and shame, and then, after a moment of humiliated, frantic contemplation, resolve.  No matter what, she was going to make sure Troy didn’t find out that she was, well, a he, and that no one else would find out about this one, isolated incident.  And, she was going to hit Sanka right in the face.   She tried to calm her heart as Troy whitewashed her innards, and her asshole as well, so that it’d be loose enough for him to pull free and maybe finish the rest on her back, instead of blowing the whole thing in her creamery. 

Nat’s skin was on fire with embarrassment and trapped heat where his butt-assailant pressed up against him.  Troy was so insistent that he abandoned all hope of even a partial pull-out finish, and instead waited sullenly for him to finish filling Nat’s fuckhole.  Nat was done, no question, which made it even less appealing to have him twitching on the inside, and so when he finally stopped jerking, it was a relief, even though he was still forcing open Nat’s anal walls.  When he did slip free with a final slippery noise, Nat discovered that the hole wouldn’t close all the way, much to his chagrin. 

Even more chagrining was what he did next.  Troy turned Nat’s head, pulled off the tape, and gave his butt-bitch a surprise kiss, making “her” eyes go wide.  “She” then just nodded passively without saying anything because “she” didn’t want to be found out.  Troy smacked his little anal slut Natalie on the ass, asked “you good?” and “she” nodded again, not wanting him to help untie “her” and find it out.  Figuring that meant she wanted him to go, he put on his pants, wiped the lube off on Natalie’s behind, and then left “her” there gaped and cum-filled.  Nat was glad he was gone, but was less pleased to be tied up, dressed as a slutty girl, clearly just having finished an anal encounter of the wrong kind.  He dreaded someone walking in and thinking he was some kind of pervert who took it in the ass, instead of some kind of pervert who took it in the ass incidentally.   He could feel the heat and wetness that Troy had left somewhere deep in his bowels, and dwelled on the uncomfortable fact that before Troy had arrived, that and the slightly-open state of his anus hadn’t been like that.

Nat was in a half-conscious haze of post-sex uncertainty.  Unable to get out of the bindings, it was only a matter of time before the boyhole that Troy had unwittingly plugged expelled his creamy consolation prize, which ran down Nat’s thigh.  That was the last thing Sanka’s little webshow saw before she went offline, her heart racing.  She was almost as confused as Nat was.

What was she going to do next?