Chapter Text
At a certain point in time, located in a certain somewhere, with certain people of a certain (but most assuredly legal) age, existed a school.
Certainly.
And now that the word “certain” has been ruined for you for the next hour, we may begin our tale.
The school in question was The University of Greatness. TUG to most.
You see where this is going.
Within TUG existed three people of note. We meet our first within the confines of locker two-six-two.
“Hello? Hell-oooo?” A light, sweet, and most assuredly feminine voice calls from the locker. “Can anybody get me out of here?”
A passing group of four girls catch the call for help and, in a rare case of mercy that is generally unknown to the students of TUG, open the locker for the trapped voice. Out comes tumbling a girlish figure that is short and cute.
“Oof!”
The group of girls stare at the figure as they stumble to their feet, fixing the red framed glasses on their face. Sighing in relief, they beam.
Their slender form stood at only five feet, even with their heeled booties that added an extra inch of height. Cerulean eyes stared with openness that was far too vulnerable, with peach skin and a rosy complexion. Their bright pink hair was tied back with two puffy scrunchies into two bouncy twin tails and multiple clips were used to keep said hair out of their face.
An oversized, pastel yellow sweater that exposed the white frilled dress shirt hidden beneath. It still revealed the fact that they were very much flat chested. A teal, plaid skirt that stopped just above their knees and their legs were clad in sheer black tights.
“Thank you!” They chirp, bouncing on their feet.
They receive no verbal response, instead the group of girls lean in and whisper to one another. They wait in confusion until the girl at the front who released them from the locker, taller than them by a few inches, turns back to them and asks:
“You're Taylor, right?”
The now named Taylor nods. Interactions that started like this generally didn't end well.
While before the four girls remained indifferent, now they were grinning and giggling amongst themselves. Interactions that started like this ended particularly poorly for Taylor. Another girl leaned in.
“Taylor Han, right?”
Trembling a little, Taylor nods again. Now they're all laughing outright.
Girl A at the front, who we'll just call the leader due to her height and general leader-ness, recovers first. “Oh my God, it's actually you! We thought you were an urban legend or something!”
Girl B, who looks to be the sharp, cold, and smart type, nods. “Indeed. The student leaders at orientation were telling us about you. It just sounded like something to scare freshmen though.”
Oh great, Taylor thought dimly, now I'm a story for freshies.
Girl C, a tomboy if ever there was one was still laughing, and Girl D, who looked as cute as Taylor and even stood slightly shorter, pointed and finally squealed out:
“It's the girly-boy!”
Okay, not the most flattering way he had ever heard it, but then again, Taylor had definitely received worse.
“U-uhm, yeah. That's me... I guess...”
You see, Taylor was the unfortunate case of having grown up in a family of only women. Three older sisters, two younger ones, and several dozen female cousins. He had two moms, and both of them only had sisters too, so he had a litany of aunts as well.
He didn't have some tragic abusive backstory, either; at least, not in regards to how he dressed and acted. He had just grown up surrounded by girls being girls and women's fashion, and by this point he knew it better than even some of his family did. He wouldn't have been able to dress “like a boy” even if he had a whole store to himself.
So he went with what he knew and dressed like this instead. He thought he was pretty cute, too!
“Wow, you're way prettier than they let on,” Leader girl circled him, taking in his appearance. “Whoa, is your hair just, like, naturally this color?”
“Y-yes?”
There was a general hum of interest. Apparently he had a rare condition that did this, his sisters were the same.
Tomboy girl piped up. “Does that mean the other thing is true, too, though?”
“Wh-what other th-thing?” Taylor asked as the four girls surrounded him.
The sharp one leaned down and lifted his skirt. Yelping, he flushed brightly as they all laughed.
Ah, yes. That other thing.
Visible beneath the tights he wore was a pair of red, polka dot panties with a flowy frill around the leg holes and a matching red bow on the front. A small (emphasis on small) bulge was visible if one bent over to look for it.
This one took a little more explaining.
See, Taylor had a habit of finding himself in situations of the— how should I say it?— nerdier variety.
His sisters and cousins, both younger and older, made it a habit to prepare Taylor for his school life by using every bullying technique possible on him. Of course, it became increasingly obvious over time that he would never get used to it, and that was part of what made him such an enticing target to so many.
He pressed his skirt down and tried backing up, only to bump into Leader girl.
“Oh wow! Girls, this is our chance to cement our place here!”
They all trilled in agreement and Taylor squeaked.
“And b-by that you m-mean...?”
With a girl in front, behind, and to both his left and right, he had his tights pulled to his ankles and a pair of hands each grip a side of his panties.
“W-wait! Y-you don't have to d-do this!”
Leader girl gave him a barely apologetic smile. “Sorry dude. Dog eat dog and all that. No way am I ending up on the bottom of the totem around here. That's a death sentence!”
Not like they had to tell him. TUG was known for it's absolutely ruthless student hierarchy. He was intimately familiar with the bottom of the totem considering he basically was it.
And with no other words than a countdown, each girl lifted as Taylor felt his ass get yet another vicious all around wedgie, squishing his junk as he screamed in a manner that befitted his wardrobe. Sixth wedgie of the week.
It was Monday.
/\~\/~/\
Recall that this was a story about three people, yes? We'll see more of Taylor soon, worry not.
Hm? You didn't really think four girls that were referred to as Girls A through D were going to be main characters, did you? They didn't even have designs! They're recurring plot devices, at best!
Anyways, the next colorful character we shall be following is... Well, anything but colorful.
“Emo” as the kids say. Or “goth”? Maybe a kind of... Grunge? Dark. Their aesthetic was dark.
Queue those returning plot devices, walking down the hall after having brutally wedgied Taylor's panties into fine threads and shreds and leaving him back in the same locker they found him, Leader girl sighed contently.
“Man, that was fun! I can't believe we actually got them over his head! I thought atomics were, like, a cartoon thing!”
The rest agreed. It was an impressive bout of wedgies that had occurred.
A rough but girly voice cut through their chatter. “Hey, freshies. Shut the fuck up. You're too damn loud.”
They all startled, having not even noticed another person in the hallway. Standing in the shadows was a lithe figure, back to the wall as they glowered at the group.
“Hey! I'll have you know we just wedgied that cute boy a few paragraphs back!”
Watch it plot device, that wall was just rebuilt.
Rolling their eyes, the figure stepped from the shadows, allowing them to get a better look at the rude, potty-mouthed individual.
Oil black hair in a sharp bob cut framed their face but their undercut left their features fully visible. Pierced ears, pierced brow, and, sure enough, a pierced nose. If you looked down, they even had a naval piercing. Their skin was pale, almost ghostly white. Their eyes were gray, surrounded by black eyeshadow, their face looked stuck in a permanent scowl. They were short, just scraping five foot three, but still somehow managing to look down on everyone.
Their clothes matched their hair: black. As if to make up for the fact that their skin was nearly sheet-white, all their clothes were the opposite. What could barely be considered a crop top covered their chest, ripped along the bottom, leaving both shoulders, collarbone, and clavicle fully exposed. It'd be almost scandalous if not for their completely flat chest.
They wore a pair of shorts that were dangerously tight and ripped to expose threads at the leg holes, coming up to just below their belly button and riding up their ass to expose undercheek. Their belt was studded with spikes, and they wore bracelets to match it around each wrist. Fishnets covered their legs and ended at a pair of black converse shoes.
They also had an absolute dumptruck ass. Just saying.
They growled. “I don't give a fuck what bottom-of-the-barrel loser you brats diddled. It has nothing to do with the original point of shutting the fuck up.”
Sharp girl glared. “And who exactly do you think you are?”
They were unfazed by the tension. “Cassie. Terrible to meet you. Now shut your damn mouths, harpies.”
Offended, the girls found themselves surrounding someone for the second time in so many minutes.
Tomboy girl sneered. “Easy there sis, I think that fat ass of yours needs an attitude adjustment!”
Cutesy girl pumped a fist. “Yeah! Through your butt!”
Sharp girl dragged a hand down her face with a sigh. Leader girl just continued on to save face.
“C'mon ladies! Let's show this girl who she's messing with!”
Huffing a sigh, Cassie couldn't look any more over this moment if they tried.
A handful of minutes later Cassie walked away, dusting their hands. Behind them, the scene could only be described as a mess.
Leader girl's eyes were crossed, having been punted between the legs only to have her thong torn off on her way down.
Tomboy and Cutesy girl currently had the others' panties pulled over the opposite’s head, their hands bound with each of their belts, which had the side effect of their pants now being on the floor.
And Sharp girl was naked, her clothes having been tossed out a window. To preserve her modesty, she had been granted the mercy of being stuffed in a trash bin head first, so only her lower half was on display. How generous.
Who was this mystery girl?
Maybe you'd be surprised, but you've seen this before.
Cassie Harthwright, or more specifically, Cassidy Harthwright. First and only son of the Harthwrights. Yes. Son.
One femboy? Happens, I guess. Two? In no less than an hour? That's more than a coincidence. How did this one come to be?
While Taylor was a matter of being raised into femininity, Cassie's story was more of a selfish one.
Once upon a time, Cassie would dress the same way he did now, only all his clothes fit. Then, around puberty, he stopped getting new clothes or cutting his hair short due to laziness and “they just don't do the style right anymore”. Add in the fact that all his sitting around doing nothing and a hilariously unfortunate gene pool left him with twin moons for an ass and an inability to grow any body hair, and he just ended up looking like a girl.
But while he could have course-corrected all of this; say, gotten a more masculine haircut and clothes that said more about his true gender, Cassie was lazy to a fault, and had no desire to do all of that work.
But that wasn't the why that we're looking for here. The reason Cassie maintained the facade of a woman was because of one simple fact: basically everybody will bend over backwards for a hot goth chick.
He may not have had a chest to entice people with, but that's why he cut all of his old jeans into shorts. To show off what he did have.
Did we mention the absolutely perfect ass? Swore we did. In case we didn't, Cassie had a damn fine ass and he knew it.
So Cassie masqueraded as a girl because it made his life easier. It also allowed him to be the biggest bully he wanted and half the time people would beg him for it. Power was power, and if he had to pretend to be a girl for it then so be it!
And as Cassie rounded the corner, he sighed now that he could finally go back to his dorm. He kicked lockers as he passed, taking pleasure each time one of them broke and opened, people's belongings spilling out.
“Eep!”
Until one locker spilled out a girl instead. Actually, upon closer inspection...
“Well, well, well,” Cassie grinned, all thoughts of taking a nap gone at the sight of the nerd in front of him, “If it isn't sweet, little Taylor!”
Indeed, the same locker from before had deposited Taylor right at Cassie's feet. Taylor looked up, dazed and still feeling the pain from the panty flossing he'd gotten from those girls.
“Huh? Who's... O-oh no...”
Cassie leaned down, staring right into Taylor's eyes, grinning like a shark. “Oh yes.”
You see, Taylor and Cassie had a history. That history, of course, being that Cassie takes an intense amount of joy in being Taylor's biggest bully. Any trick in the book, Cassie's pulled it on Taylor and that's not counting all the original tricks either.
Taylor didn't know that Cassie was a guy too, and Cassie loved that Taylor looked like even more of a girl than he was. Femboy on femboy bullying, folks. That's true magic right there.
“You know, I heard you got your cute widdle panties ripped by some loser freshies. What does that even make you?”
Taylor flushed, glaring at Cassie's shoes.
“Sh-shut up! I-it’s not like I w-wanted it to happen!”
Cassie just chuckled and grabbed Taylor by the chin, forcing him to look into his eyes.
“Are you sure? I bet you actually love it.”
Before Taylor could deny it, a third person made their presence known.
“So are you two gonna kiss or what?”
/\~\/~/\
Let it once again be stated that it was said there were three main characters here, and we've only met two. Our third can be found naked in the locker room, changing after their workout in front of their, well, locker.
They tied back their strawberry blonde hair into a big, voluminous ponytail, situating a sterling tiara on their head. Their sun kissed skin shone from a fresh application of moisturizer. Pale green eyes scoured their face, making sure everything was in check. Eyebrows? Perfectly manicured. Lips? Full and glossy, as they should be. Humming in satisfaction, they leaned back, having to bend from their five foot eleven height to look in the mirror, and put their hooped earrings back in followed by their moon necklace.
Finally they dressed themselves. A cherry red crop tank top hugged their form well, especially their rather impressive chest. Slipping on a magenta v-string thong followed by a dangerously short, white, ruffled miniskirt with spats sewn in that hugged her ass magnificently. The waistbands of their thong peaked above their round, curvy hips, showing off their panties. White thigh high socks clung to their long, powerful legs, squishing thigh meat between spats and socks down in a tantalizing way. Lastly, they slipped on a pair of platform sneakers that matched their top in cherry color.
Satisfied, they cocked a hip to the side and struck a pose for the mirror. The outlines of abs were on display and their arms and legs flexed to show the athleticism honed into them. In their beloved seductive and husky tone, they complimented themself.
“Macy, you are one fine bitch.”
Macy-Lyn Dunning, star athlete of TUG and known to be one of its golden girls. Name a sport and Macy was at the very least pretty damn good at it. As if to top off all the stereotypes, she was also the captain of the TUG cheerleading team, and there wasn't a group of girls she'd be happier to have her back. Each member went through a rigorous tryout, not to mention brutal and humiliating initiation and hazing, and while the vote was done by the whole team, Macy always had the final say.
To many at TUG, she was everything. Strong, fast, kind, funny, pretty, sociable. The epitome of a Mary Sue.
But let's be real, you're probably waiting for the twist. Patience friend.
Macy left the changing room and made her way down the hall. There was some commotion that sounded like a group of girls in extreme pain and discomfort, but that was par for the course at TUG, so she ignored it. Probably some freshies that got too big for their britches, so an older student made sure their britches were big enough to fit.
She rounded the corner to see an interesting sight.
On the ground was Taylor Han, the campus’ local femboy and bully magnet. She actually had a soft spot for him, going out of her way not to bully him (much, at least) and even harboring a little crush on him. She couldn't help it! He was just her type! Smart, sweet, and caring, absolutely adorable, and innocent enough to be endearing but not so much to be annoyingly naive. She would pull his panties a few times in the hallway when she was with the cheer team because it let her get closer to him.
Okay so maybe she was past ‘a little crush'. Sue her.
Above him was his most notable bully, the much wanted Cassie Harthwright. She and Cassie never got along. They were like oil and water. One was happy and nice, sporty and tall and filled out in all the right places. The other was short and mean, and all of her growth went to her ass, the only department that Macy would have to admit she was beat in.
She watched as Cassie leaned down to grab the feminine boy by the chin and she couldn't help herself from speaking up.
“So are you two gonna kiss or what?”
They both yelped and turned to her quickly, blushing cutely as they made a fuss over her comment.
“Wh— hell no! With this loser!?”
“I'd never kiss her!”
Macy sighed. And here she thought that maybe the bullying thing was actually a front for their secret, sordid relationship. Seemed like it was just regular bullying. Lame.
“That's too bad,” Macy tutted. “You two would be cute together.”
Cassie hissed. “Shut up, bimbo! Stay out of it unless you wanna piece too!”
Taylor blushed harder. “D-don’t say things like that!”
Okay, she was just going to leave them to it, but the punky one called her a bimbo and while she was generally pretty nice, she was also the captain of the cheerleading team for a reason beyond her skills. Despite being known for her kindness, Macy was also known as a top dog among bullies. She just didn't go out of her way to get people unless they annoyed her or, in Taylor's case, were cute enough to eat.
“Oh, Cassie, why would you say such hurtful things?” Macy put on the princess tears. “And in front of adorable, innocent Taylor?”
Cassie growled and marched right up to her, standing on tiptoes to press her nose into Macy's. Almost there...
“Quit the damsel act! I don't buy that your stupid ass gives a single shit!”
“Oh?” Macy smirked, tears gone, “You wanna talk about ass? You know practically the whole school calls you Assie behind your back, right? Not that it's hard, considering there's so much back to be behind.”
“That's it!” Cassie lunged forward.
Checkmate.
Macy swept her leg out and brought it back up in one swift motion, tripping Cassie into a straight fall down towards her foot. Nothing like a good old cunt punt to fix that nasty attitude. Also, nobody called her a bimbo! She was still pure! ... Not exactly by choice, but that was because of her... Condition.
What she expected was for Cassie's eyes to maybe cross and her to sputter and wheeze before waddling away. That be that, she'd do what she set out to do.
But the reaction was very different once her foot swung up into Cassie's crotch.
“AIYYEEEEE!”
Cassie hit a pitch higher than her normal gruff voice. Taylor winced but watched on, also clearly confused.
“Eh?” Macy was a little lost. She nudged up a few times, earning more yips from Cassie. Her eyes were rolled back and her face had gone very pale but was now turning a little green.
Finally, with one particularly harsh nudge in which Macy definitely felt something shift under the front of Cassie's shorts, Cassie had enough sense to speak again, albeit in a very pained and high pitched tone.
“Stop touching it you perv!”
It?
Cassie evidently didn't mean to say that out loud, as she(?) went pale again.
That's when it finally clicked for all three.
“You're a boy!?” Taylor looked outraged, but at the same time even more embarrassed.
“I can't believe that Assie is a boy!” Macy gasped, then remembered the feeling on her foot. “A little boy too! Like, wow, there wasn't much down there, huh?”
Cassie blushed a furious red from both anger and humiliation. “Sh-shut it! Both of you!”
Taylor finally got to his feet and stomped up to Cassie pounding on his shoulder. It felt like a kitten for all the effort Taylor was putting in. The boy was soft and sweet, not fit for anger.
“You always say things like ‘you’re such a girl!’ or ‘why don't you act like a real man?’ and you're doing the same thing!”
Macy had doubled over laughing now, wheezing and pointing at Cassie. For his part, Cassie pushed Taylor away and snarled.
“Not a word of this to anyone bitch-boy! And you too whore!”
And just like that Macy stopped laughing and glared at him. Straightening up and turning up her nose, she sniffed.
“No. I'm gonna tell everyone.”
Cassie bared his teeth. “You. Wouldn't. Dare.”
Macy smirked, pulling her phone out from between her boobs and unlocking it, dragging up a chat that was titled ‘Gurls’.
“One message is all it'll take.”
Cassie's anger evaporated almost instantly as he paled so quickly, Taylor was afraid he would pass out.
“You can't!”
Macy hummed, tapping her chin in mock thought.
“Nah, I don't really like you and it'll be crazy funny to see everyone beat those boy-buns raw once your secret is out!”
She started typing and Cassie squeaked. Taylor was having whiplash at seeing the normally rough and tough Cassie so easily cowed.
“No! Please!” Cassie tried reaching for her phone but had forgotten the savage kick to the jewels he'd just taken and yelped, dropping to his knees.
Macy ignored him, continuing to type and, to add insult to injury, started reading aloud as she did.
“Ladies, you won't believe the news I've got for you! Guess what I just learned about everybody's favorite ass to touch themselves to!”
Cassie blushed at that. He knew he could use his ass to get people to do stuff for him but he never knew people actually bated to it!
“Pleeeease!” Cassie begged from the ground. “You can't do this to me!”
Macy snorted. “Oh I totally can. It's easy, too!”
Cassie really didn't want to say this, but he wasn't left with much choice.
“I'll do anything!”
Macy stopped typing. She looked intensely over her phone, looking down at him.
“You sure about that booty-boy?”
More embarrassed than he'd ever been, Cassie hung his head so he wouldn't have to see her eyes.
“... Yes.”
Macy hummed and put her phone away.
“Then I've got just the thing!”
She reached down and grabbed Cassie by the waistband that had peeked out when he bent over. She hauled up as he shrieked, laughing at what he wore.
“Oh my God! Look at these things! Are these panties or tighty whities!?”
Indeed a sheet of white fabric had already climbed its way to the back of Cassie's head. It made sense in the grand scheme of things. Due to his significantly above average ass, he had to wear larger underwear. Women's or men's, it didn't matter since, at the size he needed, it was basically all the same for Cassie.
“C'mon loser! You're gonna keep your word!”
Just before she pulled away, Macy turned back and looked Taylor up and down. The pinkette blushed as he was appraised so brazenly. Macy's mind was racing. This could be a very good opportunity.
“Tay-tay~” Macy sung. “You're coming with us! After all, you know his secret too, so he needs to buy your silence as well!”
Not to mention having two adorable femboys all to herself? No way she was passing that up.
Taylor looked around for an escape route, but Macy grabbed him with her other hand, pulling him right to her side and locking him there, with his face pressed to the side of one of her massive boobs and underneath her toned bicep and armpit. She had a pleasant musk of her previous workout and fresh lavender, likely a deodorant or perfume. His hands rushed down to his crotch to cover his reaction, but Macy had seen and laughed.
“Tay-tay, you are just the most precious little thing!”
And with that, Macy dragged both boys back to her dorm. One to her chest, the other dragged by massive undies.
/\~\/~/\
Fortunately for Cassie, nobody had seen them, but there had been some close calls. When the door was opened, Macy threw him by his underwear over the side of the bed. He laid there, head stuffed in the sheets, trying to convince himself this was a nightmare he'd wake up from.
Macy's room was one of the three person dorms, but seeing as she didn't have any roommates, the space seemed large, empty even. There were no other beds, and Macy clearly hadn't gotten around to filling the space yet.
There were posters of different boy and girl bands on the walls, and she had a plush white comforter on her bed. The single window in the room had the curtains drawn, but there was a small succulent sitting on it. Her desk backing was covered with photos of her with friends, and a desk lamp shaped like a round, pink angler fish gave the room a pleasant lighting. Too bad they couldn't enjoy it.
“You too Tay-tay,” Macy gestured to the bed. Taylor looked like he didn't wanna leave her space now that he'd gotten so familiar with it. But after seeing what Macy could do when she was mad, he reluctantly peeled himself away and sat next to Cassie, albeit with a good space between them.
“Now then Assie,” Macy laid a hefty snack on his ass which made him jump up straight “are you ready?”
With Macy right behind him, he only ended up having his back pressed to her front, boobs on either side of his head and something poking him from behind.
Wait what?
And so, friend, I hit you with our third character twist. Taylor is a soft, girlish, pastel femboy. Cassie is a goth, punky, big bootied, femboy. But Macy is no femboy. She is very much a woman.
A woman with a massive wang.
She had a vagina too, under her balls where most vaginas would normally be, you know? In this world, we may refer to her physicality however we are most comfortable, through terms that we won't name here, but you know the ones. What it is, is. Macy-Lyn Dunning was a girl who, for all her life, had a penis.
And puberty had given her inches. Fourteen, to be exact.
That was the real reason she had the last say in who joined the cheerleading team. The girls had all lovingly embraced her upon one unfortunate slip up during practice, and from then on she knew she wouldn't allow any girls on the team if they were just going to bitch and moan about her having a dong.
Although she still found it just a little hard to look Stacy in the eyes after she had gotten a perfect face full of junk. Making sure her fellow members knew about her member meant she didn't have to waste energy keeping it a secret, especially when you had to worry about smacking your teammates in the face with your dong flopping out of your thong and skirt. That's why she had the spats sewn into her uniform skirts, she wouldn't take the chance for her junk to fly out again, even if the team already knew and accepted it.
Back to the moment though, Cassie currently had Macy's half-chub pressed to his butt, unable to get away from it since he was stuck between the bed and her schlong, and he was going through some conflicting emotions. Mostly fear, but the hardening of his (much, much smaller) member was deceptive.
“O-oh my...” Taylor gasped, staring at the absolute shmeat that Macy packed, a massive bulge in the front of her skirt-shorts.
“So Cass,” Macy hummed, “Actually, what's your real name?”
“C-C-Cas-ssidy...” He stammered, still in shock.
Macy leaned into his ear. “Cassie is so much cuter. No wonder you go by it, pretending to be a girl.”
Macy squeezed his ass and he bit his lip, eyes wide as he held in a moan.
She licked the back of his ear and he let out a shivering breath. She leaned in to whisper.
“But if you're gonna act like one, are you ready to feel like a real girl?”
He gulped. “Y-you—”
“You want me to stay quiet about this?” She asked. He took his sweet, sweet time, but finally, reluctantly, nodded. “Then you're gonna be my new hole.”
“I th-thought you w-were supposed to be nice!” Cassie managed to spit out.
“Oh, I am. I'll treat you like a precious little flower. But, and it's a big butt,” she squeezed again, and he couldn't hide the moan this time as her cock slapped against him again, “a fat slab like this starts to hold in a lot of juice. She's pent up, and beating it to the thoughts of your ass and scrumptious little Taylor over there aren't doing it.”
Taylor was reminded that he was somehow included here and gasped. He blushed at her admittance that she masterbated to the thought of him.
“W-wait, what am I d-doing here then?”
Macy finally gave Cassie some personal space again. She waltzed over to Taylor and held both his cheeks.
“You're gonna be mine.”
Taylor blushed deeper, but he couldn't turn to look away with Macy holding him.
“L-like a t-toy?”
Macy squished his cheeks. “No, darling. You're gonna be my boyfriend.”
Cassie crossed his legs, desperately trying to to hide his arousal because he did not need Macy knowing what this was doing to him, even if, by the look in her eye and the smirk on her face, she already knew.
“H-he’s gonna be your boyfriend!?”
“He sure is bitch-boy!”
Cassie winced at having the same thing he called Taylor thrown back at him.
“Th-then what am I?”
“I already said it. You're my new hole. If this adorable piece of candy is my new boyfriend,” she continued pinching Taylor's cheeks as she said this before grabbing Cassie by the front waistband and hoisting him off his feet in a crushing frontal wedgie, “I guess that makes you the girlfriend. ‘Cause I'm greedy, and I want you both all to myself!”
Cassie hated this. He had to. He needed to convince himself of that because there was no way he was this aroused right now.
He winced and yelped as she bounced him and he felt his balls and dick squish painfully. He needed a last ditch effort here. He glanced at a starstruck Taylor who was lost in the affection he was receiving. He went with the first thing he could think of.
“Wh-what about whoever’s bigger!”
Macy stopped bouncing him, which was a small mercy at least.
“What?”
Cassie tried futilely to relieve the wedgie he was getting before giving up and clarifying. “I-it you're gonna force me into some twisted throuple with you, I'm not the bottom bitch! So we decide positions based on who's got the bigger cock!”
Finally he was dropped and grasped his genitals and tried once more to make the throbbing arousal stop. After his little challenge though, maybe that'd be more help.
Macy smirked and grabbed him by both sides of his shorts. For a moment he thought she'd give him another wedgie, but instead of pulling up, she went down.
Then came the laughter.
“OH MY GOD!” She flicked his member and he yelled and jumped back. “You're practically dickless!”
Two and a half inches. That was all Cassie had to offer. A small, round, hairless pair of nuts and two and a half inches of a tiny dick, also smooth. Macy kept pointing and laughing, and Cassie had no clue why this was the challenge he issued. He heard a snort trying to be covered up and whipped his head to see fucking Taylor trying not to laugh.
This was beyond humiliating.
“Man, that's funny!” She wiped a tear from her eyes. Casually, she fell into a split like it was nothing and pinched one of his balls. He squealed and she laughed more, forcing him to spin so she could look at his ass. At this, she huffed.
“Damn, I was so sure you had cellulite or wore pushups or padded panties to make your ass look that way. The fact that your ass is just this big is basically God's way of telling you that you're meant to be a bottom.”
She shrugged and smacked his ass hard again, already leaving a pink handprint on his pale ass.
“My turn!” She chirped, standing to her full height and putting her hands on her hips. For a moment, both femboys were confused why she didn't take anything off until they heard threads ripping and popping.
And then all fourteen inches just exploded out.
They both stared, shocked with wide eyes and open mouths at the behemoth dick. It had to be nearly three and half inches thick too! Cassie felt his heart plunge. Giggling, she daintily lifted her skirt up, putting the whole thing on display. Her pubic hair was shaved short, but surrounded her base. Circumcised too, apparently. Macy let go of her skirt and let her shit hang, sighing in relief.
“Man, you boys don't know how tight things get down there,” she stretched languidly, her dick swinging with each movement before she turned to Taylor with doe eyes.
“Okay. Sorry Tay-tay, but you've gotta show me the goods~”
Taylor was still in lala land but was abruptly taken out of it when Macy, still in the ground, yanked his tights down and pulled his skirt up to his chest, which had the unintended side effect of pushing his sweater and shirt up too, leaving his lower half from ribs down on display.
“AHH!” He squealed, going to cover up before Macy stopped him. His whole body was turning red and Macy loved it.
“Aww! It's so cute!” Taylor didn't have a lot going on down there either. He shaved neatly, leaving an adorable patch of pubes in the shape of a heart (and the carpet matched the drapes, she noted), but otherwise had only just just under four inches of dick. And he was clearly rock hard, too. She gave it a gentle squeeze and he whined and shuddered.
“P-pl-please be gentle! I've n-never h-had anyone—!”
Macy silenced him by taking all of it into her mouth in one go, not that it was that hard. His eyes rolled back and he lost the ability to speak coherently. Cassie hardly noticed. Mostly because he'd just been struck with the haunting realization that Taylor was bigger than him. Which meant...
Popping it out of her mouth she laughed. “Aw, I broke him!” She laid Taylor gently down on the bed before turning to Cassie, the warmth on her face disappearing.
“You know what that means~”
Cassie gulped but knew there wasn't much else he could do.
“Don't be afraid, fuckmeat,” Macy smiled and caressed his face slowly. “I won't do anything if you don't want me to.”
She was giving him an out? Now? After all of this?
“All you have to do is say you don't want this.”
As she said this he felt it. Her massive dick pressing against his undercarriage, the tip poking out from between his cheeks behind him, his own pathetic dick and balls dwarfed by it as they rested on top of her shaft.
“I won't even spread the word that you're a wolf in sheep's clothing. As far as I see it, I got a whole afternoon of entertainment, proved I'm better than you in almost every way, and got an amazing, girly boyfriend out of it. I win either way.”
Damn if she was right.
All he had to do was say he didn't want it.
That was it.
She wouldn't just up and fuck him, that was full on assault. He just had to say no.
Say no.
Why couldn't he say no!?
“F-fu...”
Macy leaned down and cupped an ear. “Speak up bitch.”
He squeezed his eyes shut tightly.
“Fuck me.”
He felt weightless for a moment before he came crashing down stomach first on the edge of the bed, ass stuck up in the air. A meaty thunk could be felt just as much as heard as Macy slapped her dick down between his cheeks.
Taylor was just coming to, only to see the sight before him.
“Oh goodie!” Macy dragged Taylor over and settled him right in front of Cassie's face, both legs over Cassie's shoulders. Cassie was lost as to why.
“What?” Taylor asked, just as confused. They both thought she was going to fuck Cassie.
“I want you to see your biggest bully-turned boyfriend's face while your new girlfriend breaks his ass.”
That was a devastatingly thorough response that had both boys scared and aroused at the same time.
“Also,” Macy grinned and grabbed Cassie by the back of his head, forcing it down, “You're gonna treat Taylor to a good time too for all the times you've called him out for having a small dick, Tiny.”
Cassie gulped and looked up. Taylor was blushing brightly, but there was a slight glint in his eyes. Cassie gasped when the other femboy grabbed his head from Macy.
“Very good,” Macy groaned in a deep breath. “This is gonna be cold, bottom bitch!”
Cassie didn't know what she meant until he felt something cold, wet, and slick drip down his crack and pool around his asshole. Then two fingers plunged in and for the first time, he was penetrated.
“Ooough~” he moaned heartily, falling to the new sensation quickly. Taylor took advantage of his mouth hanging open and his lack of attention to drag his head down the rest of the way, settling his mouth on his own asshole, the pink femboys own dick pressed against his face.
Cassie got the idea, and at this point knew that resistance wouldn't end well.
He started licking. Here he was, fingers plunging in and out of his ass at increasing speeds while he slurped away at the asshole of a boy he bullied for looking and acting like a girl. What did that make him, he barely had the power to wonder. He didn't dwell on it further since Macy had started using her other hand to spank him with each thrust.
Taylor was moaning, head back and biting his other hand, balled up into a fist. Macy smirked down at the two. This was better than any of her fantasies! She was so excited, she skipped three fingers and upped the finger count to four on the next thrust.
Cassie's shout was muffled by Taylor's bussy, and the pinkette moaned and crossed his legs behind Cassie's head, locking him there. With his nose stuffed against Taylor's balls, he had no choice but breath between laps of his tongue.
Macy pumped her arm like a piston, practically punching him in the hole with each thrust. On her next thrust she reached a new depth and he twitched and spasmed in place as she started wiggling her fingers inside of him. The feeling was so foreign, he started kicking his legs, only for Macy to sit on them and lean even further onto her arm. It was the realization that she had her fist in his ass when he felt her twitch each finger that sent him over the edge.
He couldn't help it. His tongue hardened in the hole he'd had his face stuffed in, making Taylor moan as well as both boys blew their load at once. Taylor's all over Cassie's face, and Cassie's all over Macy's bed.
“First loads of the night! Good job boys!” She laid another slap on his ass and Cassie groaned, feeling spent already. His ass was also starting to get sore from the spanks. She got off his legs to kneel behind him, using her longer, stronger legs to spread him wide.
Post nut clarity also settled and he realized he just bottomed for Taylor of all people while getting finger fucked by Macy.
“Ready for the real deal, glory hole?”
He opened his mouth to say no but before he could, something was stuffed in and prevented the words from coming out. The slightly salty taste and his wide eyes shooting back in front of him told him that Taylor had, in fact, just shoved his dick in Cassie's mouth.
And once again the legs wrapped around his head as he was left no choice but to suck the other femboy off.
“I love seeing this side of you Tay-tay!” Macy swooned, lining her tip up with Cassie's hole. “Alright slut, don't you dare bite down on Taylor's little buddy, or you'll regret it.”
He would've asked for a countdown, but was given no such privilege as Macy crammed the first few inches in. He screamed a moan that was muffled, the vibrations making Taylor buzz with arousal. Instinctually, Taylor started thrusting. Shocking himself, Cassie started bobbing up and down to match him.
Another smack on the ass followed the initial penetration and Macy leaned over him, her breasts squishing against his back.
“Ready for more, short stuff?”
He wasn't but Macy took his head bobbing as nodding and thrust another few inches in. His eyes crossed and his head fell down on Taylor's prick. Both boys felt the cock just barely tickle the back of Cassie's throat. Cassie hated that he throbbed with the knowledge.
“We're almost there! Once I'm all the way in, the real fun starts!”
A few more inches went by painfully slow, stretching his hole to its limit as it flexed to compensate for the new stress. Macy giggled and ran a finger around his gripping ring. Cassie's back arched and his tongue wanted to loll out of his mouth but instead dragged down the underside of Taylor's shaft.
The pinkette hunched over, practically hugging Cassie's head to his groin as he humped his face. Macy dragged her nails down his back and he groaned at the feeling, both painful and pleasurable at once.
“Last few inches champ!”
In she plunged, grabbing both his asscheeks and spreading him out. When he started to squirm as he felt her go far deeper than anything should up the rear entrance, she hooked her legs more firmly around his and spread them wider, practically forcing him into a split.
“You took it so easily! You sure you haven't done this before?”
He was just cognizant enough to flip her off with one hand. She slapped his ass again and laughed.
“Let's see you keep that attitude!”
Her grip shifted to hold him by the waist and she dragged out slowly, inch by inch, and he cringed at the feeling, not ready for the feeling of something coming out like this. She made it all the way back until just her enlarged tip was spreading him wide and with a whoop, slammed all of it back inside.
Forget just stimulating his g-spot. Macy absolutely blew past it, her shaft squashing his prostate as his guts stretched to accommodate the absolute anal probing he was receiving.
Cassie's vision swam for a moment, unprepared for the punch to his insides. She kept going, picking up speed as she thrust into him over and over, and he felt her large balls slap against his own balls and thighs, even just her sack was bigger than his own genitals.
His eyes were wide and panicked. The feeling was like nothing else, but he was doing his best to psyche himself into hating it. He would not be the bottom of this fucked up relationship! He refused to admit to liking this feeling of being... Being used like this!
He turned his eyes up to the only person that may have possibly been able to help him. Taylor wasn't looking at him though. He was watching, just like Macy had said, as his biggest bully got absolutely wrecked right in front of him.
Taylor finally looked down, and Cassie did his best to plead with just his eyes, as his mouth was still occupied with the other boy's twig. Taylor was flushed so thoroughly, you'd think he was the one being utterly humiliated right now.
Cassie knew he didn't really deserve much mercy from the boy. He'd never done so for Taylor whenever it came to making his life hell. He fully expected Taylor to grab him by the ears and spit roast him with Macy.
Instead, for whatever reason Cassie couldn't fathom, Taylor smiled a gentle, beautiful smile down at him, and Cassie's heart thumped for just a moment.
The pinkette pulled back, his small dick popping out of Cassie's mouth, leaving a searing hot feeling on his lips. He lifted Cassie's head and upper body, supporting him as Macy continued to rail the life out of him. His slender arms wrapped around him and he hummed slowly.
Cassie felt very warm, in his chest and in his ass and balls. He started breathing raggedly, his moans now free for the whole room to hear as he finally succumbed and let go, fully enjoying his own piping.
Taylor lifted his head to look him in the eyes and he leaned down and peppered his face with kisses. It was entirely too sweet considering the absolute massacre going on behind him, not to mention Cassie's face was covered in his load. Taylor slid down and under him, forcing Cassie to hands and knees to let the pinkette slide below.
He reached under and Cassie felt his hand trace down his stomach where, for the first time during all of this, he realized that Macy was quite literally in his guts, and he could feel her distending his tummy with each thrust. Taylor must've been able to see it too, if his mesmerized look under him was anything to go by.
That same hand trailed lower and lower before it gripped Cassie's small shaft and started pumping.
“Nnnnggghh!” Cassie was overstimulated right now, too many sensations wracking him as he was utterly dominated by Macy and brought to the absolute edge by Taylor.
He winced every now and then when Taylor would squeeze his balls, his sack still tender from Macy's kick earlier. Finally they both heard Macy grunt above them.
“Alright boys, I think this shows almost over!”
Taylor turned around under him, his cock now right below Cassie's face. Towards Cassie's ass, Taylor was now under all the action, looking right up at it. He stared up at Macy's cock plunging in and out in awe before he moved in a haze, keeping Cassie's cock in one hand and plunging two fingers from the other hand into Macy's vagina. He leaned up and started sucking on one of her balls as well, and she moaned and shuddered with each thrust now.
“T-Taylor!”
“O-OH! OOOOUGH!”
Taylor kept going, even as Cassie spasmed and came into his hand. Macy's thrusts broke their tempo and she leaned in fully as she came buckets into Cassie's guts. The punk came a second time as he felt his insides flood with warmth. Too much for him to handle, as some of it gave him a little belly bump and the rest drained out of his ass and gushed out and down.
Taylor opened his mouth and caught the drippings, his fingers still pumping in and out of Macy as she continued to cum. Finally Macy pulled back and an audible and loud ‘pop!’ signified her pulling out, her testicles popping out of Taylor's lips, too. Cassie moaned before he immediately gasped, a gurgle coming from his tummy.
“Ugh! Uh oh! Rrgh— no!”
A few things happened in quick succession.
Now that Macy was no longer holding him up, Cassie fell junk first onto Taylor's face. Taylor let out a muffled shout of surprise and pushed up into Cassie's full belly on instinct.
However, with no seal to keep it all in, and with Taylor pushing on him, Cassie's now gaping hole dumped cum out, covering Taylor who yelped in shock, not expecting the flood. Macy gasped and frantically looked around for a towel, finding a few and rushing over to help clean up Taylor and, begrudgingly, Cassie as well.
She wiped Taylor's face and when she did she felt guilty. He had a kicked puppy look on his face, and before she could ask what was wrong he coughed up a few globs of cum before saying:
“It g-got on my glasses...”
Macy couldn't help the snort that came out, and she even heard Cassie huff a tired laugh. Taylor flushed and pouted, and even covered in jizz she couldn't help but find him incredibly adorable.
“Sorry Tay-tay. Did you get to cum again?”
“O-oh, uh, no, but th-that's okay! I'm j-just happy to be a p-part of it!”
Macy looked at Cassie's limp, still spurting body, cum leaking out of him like a slow faucet. Shrugging she tossed the ruined towel on his ass, making him groan at the feeling.
“Let me help you, princess.”
Taylor wasn't ready for Macy to lift him up high, his thighs landing on her shoulders as he ducked slightly to avoid the ceiling. He was even less ready for her to immediately start sucking him off. He moaned and hunched over, hugging her head to both keep him from falling and keep her going.
She did it differently than Cassie, although perhaps that was also a matter of circumstance. She sucked slowly, but her tongue slithered and flicked against his shaft and frenulum as she did and it brought him to his finish fast and furious.
When he came, he expected her to pull off, not double down and take it all the way in. She milked his climax the whole way through until he was tapping out on her head. Smiling on his dick, she finally pulled off, giving his perky butt a squeeze that made him jump.
She set him down and he fell to his back in the bed beside Cassie, who was still lying limp, but the towel had been half-assedly used to clean up the barest amount of cum before he gave up and just sat in it. His make-up had run streaks down his face and his hair was a mess.
“You look good this way Assie!”
His response was muffled as he pressed his face into the sheets. “You Amazonian neanderthal, I do not want to hear it right now.”
Macy rolled her eyes, laying down on Taylor's other side and throwing an arm around him. He snuggled up to her easily, looking like he could fall asleep right there.
They all lay in silence beside one another for a while before Macy broke the spell with a question.
“Have you guys ever imagined what it'd be like if you were ducks?”
Cassie groaned. “Oh my God, women actually do ask stupid ass questions after sex. I always thought it was a joke.”
“Pfft, virgin. Of course we do!”
He snarled. “Virgin!? You literally just expanded my ring! I don't even know if it'll go back to normal size! Fuck you ‘I'm a virgin’!”
She didn't give him any more response. After all, this was her first time too, not that he needed to know that.
It was quiet again before Macy said something far less ridiculous.
“You two should move into my room.”
Taylor startled a little. “What?”
Cassie finally turned his head to look over at her too and asked the same thing. She shrugged.
“It's lonely in here and I wanna fuck more.”
“Your aftercare is awful and your pillow talk is abysmal.”
“Sounds like we just need more practice!”
Taylor flushed and she noted that he was just embarrassed easily considering everything he'd just done. Cassie grumbled.
“I don't trust living in a room with you.”
She leaned over Taylor and slapped a heavy hand down on Cassie's ass. He hissed and coiled.
“Shit, bitch, it's still raw! No thanks to you!”
She slapped his other asscheek for calling her a bitch and he didn't do it again.
“I guess it wouldn't be the worst...” Taylor mused. “Plus it can't be any worse than any roommates I've had before.”
Cassie stared at him. “I didn't know you had roommates. I have a single. Which reminds me, how the hell did you get a group dorm to yourself?”
Macy shrugged. “I applied and they never gave me roommates. It even has its own bathroom, which most people would kill for! But Assie’s right. I didn't know you had roommates, Tay-tay!”
Taylor flushed. “Um, they generally don't last long. It always ends with me having to file a complaint for one reason or another.”
The reasons varied from too many of his panties being ripped, to being locked out of his room when he's not wearing his skirt, to even sometimes waking up with things drawn on him. There was even that one girl he found digging around his panty drawer. Creepy.
“See, Assie! Tay-tay would move in with me!”
Cassie just grumbled more until Taylor nudged him and he made the mistake of looking into Taylor's shining, wide eyes. They never worked before when Cassie was, say, tearing his panties off or stuffing his head in a toilet, but for this it felt different and Cassie quickly turned away to hide the blush on his face. Maybe it was all the cum still stuck to his hair and face. That had to be it. Not gross feelings.
“... Mmmmfine.”
Macy let out a knowing hum that Cassie ignored. Taylor looked back at her and winked and Macy realized she still had a lot to learn about these two, as much as they probably did about her. Perhaps they'd done things out of order, but after sex like that, she can't say she'd have done it differently.
And after they move in together, they'd have all the time to get to know one another!
So fear not, friend, this is not the end of the tale. In fact, it is merely the beginning! This narrator knows that these three will no doubt breeze past their vicious bouts of sex and reach new heights!
Macy broke the silence one last time.
“Kinda crazy that we're all circumcised.”
... Perhaps those heights will take a long while to reach.