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?
