Chapter Text
David and Ben were not gay. They didn’t have a relationship with each other outside of being best bros who had decided to room together in college. They both enjoyed hot girls, cheap beers, and working out.
They were fairly regular chads but all that really mattered about them was that they lived across the hall from Katy and that they were in shape. They also had the fun contrast of being a brunette and a blond and she could smell the homophobia on them which always got her hot.
She doubted that they were like, evil or anything but it helped if they had something asshole-ish about them, something that she could ‘punish’ them for, and well, if they hated the punishment in a very specific way then that just made it better for her.
It had been simple enough to get the potion inside of them. She was a chubby short girl with glasses who just oozed wholesomeness.
She had baked some cookies and offered them to the boys and they had both dug into the plate without even a thought. She had given them an hour to digest before she had given them the first command. She always starts gently, to just make sure. Simple things like, “open the door”, “don’t speak”, “sit on the floor”.
When the commands are followed without any delay, that’s when she starts to have fun. She always makes them shower first, gives them some enema bottles to clean themselves out with and tells them that when they’re done to come straight to her apartment.
She sets up until there’s a knock at her door and she sees a pair of naked wet boys with those glassy eyes that she’s come to love. Her apartment is huge, it’s actually a combination of a couple of apartments with the walls knocked down. The apartment manager is of course under her control and thinks nothing of why he never manages to get tenants into an entire half of one of his floors.
But that just means that she has plenty of space for her activities.
“Boys get on your knees in front of the balcony. Bend over and spread your cheeks.” The two glassy eyed men do as she commands and soon she has a pair of tight assholes winking at her. This is when she is faced with a dilemma.
Go slow, and gentle these fine pieces of meat into their new workouts, or throw caution to the wind and hurt them?
Katy has been a little frustrated recently, and these boys had been very loud when they were moving in yesterday, they could take some punishment.
Katy got a closer look at the little holes that were going to go through hell this afternoon. They were both tight little pink things, surrounded with a ring of hair, and they both had fat balls and respectable cocks hanging below them.
Tight assholes were nice and everything, but she likes them puffy, red and leaking. She decided to start on the brunette.
She got some rubber gloves and lube before casually talking to the boys.
“Hey, you with the dark hair, what was your name again?”
The response came in a clear voice though a bit confused sounding. “I’m Ben? I introduced myself to you an hour ago Katy.”
Katy’s nose scrunched at the sound of her name coming from his mouth, “Don’t call me by my name while you’re in my apartment Ben, call me . . .” Katy cast her mind about, she wasn’t really one for being referred to as mistress or queen. She would usually gag her toys, but today she wanted some narration, she wanted these boys to cry and beg and plead, so they would need a name to beg.
A moment of inspiration and perverted cruelness struck her, “Call me Mommy, both of you. Do it now.”
A chorus of ‘Mommy’ rang out from the two boys, and it was less of being referred to as such as it was the sound of two grown men say such a childish and demeaning thing.
Oh, she was going to make these boys scream.
Once enough lube had been rubbed onto her gloved hand, Katy gave another command, “I want you to talk to me a lot, ok baby? I want you to tell me what this feels like, and don’t be afraid to get a little loud.”
“Alright Mommy.” Said Ben dreamily, not at all understanding what was about to happen to him as his ‘mommy’ rubbed his asshole.
Katy shoved two fingers in immediately, loving the cry of pain that Ben let out. She rotated them as he gasped and the muscles in his legs clenched and his feet kicked.
“Come on baby, use your words,” she commanded, a smile crawling across her face.
“It-it hurts Mommy, it hurts a lot! Take them out, I don’t like them!” Katy could hear the stutters in his breath as he spoke to her, and it went straight to her groin. Oh, he was hurting, was he?
“Take what out of where baby? You need to be specific if you want me to do something.” Katy smiled at the ass in front of her as she began to quickly twist her fingers rotating her elbow to get some ommph behind it as his groaning went up a notch.
“Take your f-fingers out of my asshole! Please Mommy it feels bad! Don’t move them like that, it hurts Mommy!”
“Oh you don’t like it when I move them like this? Ok baby, I’ll do something different.” Katy slid her fingers out of Ben’s asshole, before sliding three in all at once and slamming them in as hard as she could. She immediately began to finger-bang the poor boy.
Ben screamed at the intrusion and arched his spine in reflex. His body clenched down on what was inside of it but that just made everything worse. His butt was throbbing in pain, but all he could think to do is beg ‘Mommy’ to stop.
Ben was an incoherent mess of pleading and chest heaving sobs as his asshole was violated. It was only after Katy had jammed four fingers inside of him and spread them wide that she got bored of his sobs and decided to switch her focus.
She jerked her hand out of Ben, forcing another sob out of him before walking to her toy wall. She got down a long string of anal beads, a dildo with a flared base and a thin length of smooth wood. She went back to her boys, one sobbing with a gaped asshole and the other pale, his asshole clenched tight in fear.
She placed the dildo in the floor a little behind and to the side of the still virginal blond boy, “Ben, come here and sit down on this.”
Ben shakily let go of his now sore ass and straitened his back. He turned on his knees and Katy smiled at his red eyed and tear stained face. He gave her a mournful look before slowly crawling to the dildo. He stared at his “Mommy” as his sore and puffy asshole rubbed on the dildo head and he began to slowly sink down, whimpering all the while. He paused about a third of the way down and pleaded.
“Mommy please, my asshole hurts so much, and this hurts too! Don’t make me.” He whined, fresh tears going down his red cheeks.
Katy cooed at her cute boy, his tears were so hot. And he was going to cry more. “No baby, sit down all the way. Your cute little asshole needs to keep wide until your friend is as stretched as you are. Do it now.”
Katy smiled at him as Ben gave a sob and his body immediately pressed down the dildo, his asshole pressing hard to the base of the dildo when his full weight was settled on the floor. Once he was fully settled, Ben could not control the scream that came from him. His body started scrambling, trying to get off of this terrible thing even while nothing but “Mommy’s” commands kept him from standing up.
With Ben taken care of for the time being, Katy turned her attention to her other ‘baby’. The blond had clenched his hands so hard on his own ass cheeks that Katy was sure he was going to have an interesting bruise in a few hours.
“What’s your name baby?”
“My- my name’s David. Please don’t hurt me like you did Ben. I don’t want fingers in my ass! I’m not gay!” David was frantic, the sounds of his tortured best friend riling him up, even if the mind control kept him on his knees.
“You don’t want fingers? Okay baby, I’ll give you something else.” Katy ignored David’s chanting of “no Mommy please no.” as she lubed up the first anal bead. It was very small, only about the size of a marble but they would be getting larger as she moved down the string. She supposed that she was being kinder to David, starting smaller and all. She resolved to make up for it later.
“Relax baby, here comes the first bead!” With a little bit of a sing song in her voice, Katy fed the first bead in to David’s ass. As she knew it would, it goes in with little trouble. Her command of “relax” going through even if David was keening through the entire thing.
But she quickly followed the first bead with the second, and the second with the third until she was having to press harder and harder to force the little balls into the blond boy.
By the sixth bead David’s asshole was straining, the wrinkles stretching smooth around the glass spreading him wide.
Katy couldn’t help but talk down to the boy who was breathing heavily as his insides were filled with glass beads. “Come on baby, your cute little asshole is hungry for something to fill it up! Look at how it’s gulping down these beads! Are you sure you’re not gay? I think that we’ll have to test that some time! You would look so cute with a cock down your throat. And maybe we could even get more than one dick up your ass at the same time. But we’ll have to loosen you up for that, come on lets pop in another big bead for practice!” And with that she put her weight behind her and popped in the sixth bead.
David started to sob at that, his begging changing its tune from “stop” to “take them out”.
Katy decided to use that as an excuse. She slapped the hanging balls in front of her. The scream that brought forth made her add a few more hits to each ball before saying what got her ‘mad’.
“Don’t make demands baby! You have to say please to your mommy, or you’ll get punished!”
David immediately began to sob out “Please Mommy please!” and Katy took much pleasure in loudly proclaiming, “Oh, you want another bead so badly? Here you go!”
David didn’t have time to correct her, his words getting lost in a scream as his ass was spread over another glass ball. This one much larger and straining his asshole almost to the point of tearing.
But like the others it popped in with some struggled and his anus continued to wink around the string trailing out of it.
Katy frowned. That last one had gotten close to tearing the skin. She didn’t want to make her toys bleed. She wanted them in pain, not damaged and that last one had gotten close.
But she didn’t want to stop at only seven beads! He still needed to take at least one more for him to be at the same level as Ben, and it seemed like it would be unfair to only stretch one of them so wide.
Katy sighed before beginning to tug at the string, pulling the last ball to the puckered skin and making it gently crown before allowing the asshole to swallow it back up. She was really going to be too kind to David, she would need to make up the difference latter.
“Really baby, you’re going to get spoiled! I’m going to have to even this up later, so be prepared!” And with that Katy tugged the bead out.
The momentary relief made David sigh at the lack of pressure inside of him, but it turned into a cry as she immediately began forcing the bead back in. She was steadily fucking the blond boy with the anal bead, his asshole staying wide open for a half second more with each time she forced his muscles to allow the bead through them.
Pop, pop, pop, went the bead and with each pass his asshole became softer. When she forced it back in and quickly followed it with the eighth bead, his anus only stuttered for a moment before allowing it in and closing over the cold glass, but David couldn’t help but scream and shake his ass at the feeling of biggest thing ever entering his ass.
Katy smiled at the slowly closing hole, and glanced at the beads still hanging outside of his ass. She would have to make him take the whole string one day, but for now eight were enough to stretch him out.
Katy glanced back at Ben to find him crying silently still impaled on the floor. His dick limp and touching the ground, tear tracks coming from his eyes as his abs flexed at the feeling of the soft silicon being behind them. The length of the dildo, and the way he was sitting on insuring that it was pressing right into the turn of his colon. She had read that it was one of the most sensitive places inside of a man’s body.
Katy left David crying on his knees, cheeks still being spread by his hands as the string of beads still hung outside his ass like some kind of tail.
She crawled over to Ben and cooed at him even as he leaned back, sacrificing his balance to try and get a little bit farther away from her.
He ended up falling over, mouth giving a scream as he fell on his back, asshole getting tugged wide for a moment at the dildo slide out of him at an angle and soon he was left gasping like a fish as his asshole was pink and wide, bereft of its pacifier. Katy giggled at him, the way that dildo slid out must have pressed the entire length of it against his prostate.
Talk about a wake up call. The sudden intensity must have felt good, because his formerly soft cock had gotten to a half chub just from it.
“Oh no baby! Your toy fell out! That’s what you get for trying to run from Mommy. We’re going to have to punish you for that.” Katy smiled at her sobbing boy as she reached out to check his anus. It was soft and puffy the way that she loved, but she wanted this boy to feel empty. She wanted him spread and sensitive.
She had an idea.
“Come on honey, stand up! We’re going to fit you for a nice little outfit.” She got to her feet and walked over to a section of her collection. The wall was covered in straps and dull metal hooks.
Katy had been thinking of this for a while, but she had never had a body on hand when the thought had crossed but now she is ready to try it on this sweet boy.
Ben had gotten up and followed her to the wall, his hands having found their way between his cheeks and were coving his anus. He was still in the grip of her mind control, but he managed to feel horror at the loose feel of his anus. It hadn’t managed to close and he could feel the wetness of his well lubed insides on his rough hands.
“Come here baby. Yes, right there, now bend over and grab your ankles! Don’t let go until I say so!” Katy smiled as the bendy boy followed her orders and suddenly she had an ass pointed at her. She smiled as she took the straps and the hooks she had chosen and began to fit them to his body.
The straps were very elastic, but were short enough to ensure that it would take a bit of a stretch to accomplish what she wanted. She couldn’t have them go slack and fall off!
Once she got the straps where she wanted, Katy gently slid the curved hook ends into the puffy anus, four of them each going to a corner and once she felt that they were in correctly, she let go of the straps.
Ben, who had been crying silently at the feel of her manipulating something on his hips and his ass was unprepared for the sudden yank that happened to his asshole. His loosened ass lips had been spread wide and were straining at the stretch of the straps. His asshole could tense a little, the hooks tugging at the edges of his gaping anus as the muscles fought the stain of the elastic. But the muscles would eventually relax, his body being unable to keep up the effort and his ass would be seemingly spread even wider as his flesh gave up the fight and gaped for Katy’s eyes, her enjoyment obvious.
It was hot, the way that his pink flesh struggled to close, only to be yanked wide once more. The gape probably felt huge, but was really only about a two inch hole. For now at least, Katy didn’t plan to take this off for a while. She would see how stretched out he was tomorrow.
Katy grabbed the dildo off of the floor, where it had been forgotten. She quickly and without mercy slid it into the presented asshole and shivered at the tear broken cry of “Mommy Please no!” that she got.
She slid it all the way the base, happy that it still caused the asshole to open a bit as the silicon worked with the hooks to spread his ass even wider. She tapped the flat plastic base a few times before giving an order that she knew would give the boy one hell of a work out.
“Ok Baby! I want you to stay in this position and try to push out the dildo. If you manage to push it out I will give you a reward! If you fail you’ll get punished. You have until I’m done with your friend ok?”
All she got in return was some more sobs, so she gave the gaped and stuffed ass a slap.
“Ok?!”
“Yes Mommy!” Ben shouted, and he began to strain as his muscles battled against not only the hooks keeping him open, but gravity keeping the dildo deep as well.
“Good Boy.” Katy nearly purred as she watched the muscles strain under his skin. He was all set while she finished up with the other boy.
David had calmed down a bit, his sobs slowing down to just gasps.
That just wouldn’t do, Katy wanted him in tears. As she watched his pink little hole wink and flex around the string hanging out of it, she knew exactly how she was going to make it happen.
She grabbed the thin length of wood that she had gotten down earlier and she took hold of the end of the beads, hooking her finger in the ring at the end as she steadily pulled.
The puffy asshole distended outward and David gave a pathetic whine as the huge bead was slowly pulled from his ass, a loud POP sounding as the tired muscle finally gave up and let the glass pass through.
After the huge bead left him, the others slid out easily, his asshole already stretched enough to easily let them pass and soon the puffy ring of his anus gaped around nothing as Katy tossed the beads to the side. She pressed a few fingers into the puffy flesh, feeling the stretch and pulling it open for her own enjoyment. David sobbed out a “Mommy” as she did this and Katy couldn’t wait till he was screaming again.
She stepped over his body, straddling him as his hands still held his flesh open for her, and she couldn’t help but tease him a little.
“Ok baby boy. It’s time to have you pay for the kinder treatment from earlier. So, you’re going to get spanked! But not just any spanking, a very special spanking with a very special tool in a very special place! Won’t that be fun?”
Katy tapped her piece of wood very gently on David’s ass, just letting him feel the thing before she gently glided it between his cheeks, making sure that it was centered right on his puffy wet anus before raising it up and slapping it right down.
CRACK
David screamed and his body shook from his own struggling between her legs. Katy clenched him between her knees to keep him steady as she let him work through the pain that had been visited on him.
Eventually his cries turned to words, a chanting of “Not again, not again, please Mommy don’t hit me again.”
Katy shivered at the desperate begging, his voice only raising in pitch and volume as she centered the wood over the clenching anus again. She raised it up, “Mommy loves it when her baby boy begs and cries! So, let’s give you something to cry about.”
She brought the wood down.
CRACK
This time she didn’t let him rest, she just kept going, slapping the wood down on his most sensitive flesh, basking in the cries and screams that came from between her legs.
But once her mental count came to twenty, she gave him one more for enjoyments sake and stopped straddling the pain mad boy.
She bent close to make sure that she hadn’t damaged him. She had been trying to not focus on one place, spreading the caning around so that the skin wouldn’t break. The anus was an angry pulsing red and was swollen from all of the abuse, but other than a bruise at the edge it looked like nothing was damaged.
Katy was proud of her own self-control and was considering telling the boys to go back to their own apartment when she heard a dull “thud”.
Katy turned and was surprised to see the dildo on the floor. Ben was staring at her, his face a bright red and sweat dripping from his temples. It looked like he had strained enough against her straps to actually push the dildo out!
Katy was impressed. She wondered at what she could do to reward him when David made another groan and suddenly she knew exactly what she was going to do.
“Good job! Come here baby, let’s get you a treat!”
Ben unsteadily got out of his bent over position, all of the blood rushing out of his head. He tottered over to her, his face flinching at the way the straps tugged at him as he moved. Katy could only imagine how uncomfortable it must be to move while wrenched open like that. She pressed her legs tight together.
Ben knelt next to her and Katy didn’t waste a second. She grabbed the lube bottle and immediately began to give Ben a hand job. He gasped and flinched at her touch, but a strict “Stay still” kept him in place as she began to work him over.
It took a while before he began to get hard. Katy was sure that the pain and blood rush weren’t helping, but like hell was she going to give these boys time to recover, she wanted to do this while it was all fresh.
Eventually Ben was fully erect and Katy took her hand off him to cruelly slather the remainder of the lube on David’s now even more swollen asshole.
David gave a short little scream at the touch and Katy knew that what was about to happen next would be absolutely hellish to him. Her pussy clenched in her wet panties.
“Now David, I want you to let go of your ass cheeks! Ohh, your swollen little hole is peeking out, it’s so big now! Ok, brace yourself as well as you can on the floor.” David moved slowly, but he had been holding the same position for a while now so she wouldn’t punish him for the delay. Once he was all settled Katy smiled really big at Ben.
“Ok Baby boy, now slide your big hard dick into David’s hot little asshole! And fuck him till you cum.”
Ben’s eyes widened in horror from where they had gone tight with pleasure, and he shook his head in denial even as he moved toward his best friend’s tortured ass.
David had immediately begun to scream and beg, and his volume had only gone up when he felt Ben’s hand touch his ass. “Please no! Don’t do it Ben, please don’t do it! My asshole hurts so much! Please Mommy no no no no! Don’t make him do it! Please no, don’t! I’ll die! You’ll kill me! Mommy, please!”
Katy had jammed a hand down her pants as she leaned over to get a better look at Ben’s dick gently nudge at the inflamed asshole before the head slid in. Ben paused, body shaking.
Katy knew that with the increased blood flow to the area that David’s asshole must be hot as fire and even with how he had been stretched before, the swollen flesh must feel hellishly tight. David had stopped using words and was just screaming animal noises now.
Katy laid a hand on Ben’s lower back and spoke directly in his ear. “Go balls deep now.”
Ben’s body jolted forward as the order entered his brain and suddenly he was bent over his screaming friends back as he gasped at the terrible pleasure raping his best friends annihilated asshole brought him.
Katy moaned, “Tell me what it feels like Ben. Let David know how nice his asshole feels. Give him a hard slam too.”
Ben gasped before he followed her instructions, pulling out to just the head before slamming balls deep once again, and his mumbled voice was only barely audible over David’s pained screaming. “It feels so good David. Your asshole feels so good. It-it’s tighter than any girl’s pussy and it’s so hot. It’s like it’s boiling, it almost hurts. I-I’m not gay, I’m not but anal feels so good bro. You feel so good on my dick!
Ben began to slowly move without Katy’s instruction. At first little jolts into the now crying boy’s asshole but as the pleasure began to win out, long slamming thrusts. He even situated himself for better thrusting, spreading his legs and placing both of his hand’s on David’s hips to slam him back on his dick.
Katy was rubbing herself to an orgasm as she watched Ben’s fat ball sack slap into David’s limp and soft cock. She jolted at the sounds of David’s harsh sobbing, his lungs now too tired for screaming. She finally came when she watched Ben’s balls began to tighten and pull up below his still strapped open asshole. The pink muscles inside easily visible and busily fluttering with the activity going on.
Eventually Ben pressed in balls deep and Katy could see how his balls and muscles jumped as he orgasmed deep into the tortured asshole of his best friend. He began to pull back, but a harsh, “Stay as deep as possible!” had him leaning his weight back onto his friend.
Katy finished up her orgasm and shakily got to her feet.
She began to walk around her apartment, washing her hands and tossing toys into the “used” bin to be dealt with later, purposely ignoring the boys on the floor, still intimately connected. Soon she was done with the upkeep and she turned to look down on the boys with a little bottle in hand.
“You boys did a very good job and I’m very proud of you! Say thank you.”
Both boys, exhausted and still in pain muttered out a chorus of “Thank you Mommy’s.” and Katy shivered a little.
Huh, maybe she is more into that then she thought.
“Ok, now Ben pull out slowly, try to keep your jizz in your friend. David, clench down. Oh, that sounds like it hurts a lot, but you can do it baby! Now Ben I want you to keep those straps on all night, but come to see me in the morning before you go to school ok? You have your first college class at what, ten o’clock? Then I want you here at nine ok? I need to take those straps off, and play with you a bit! And David, you stay on your hands and knees until you’re in your apartment. Here take this bottle, AH! Not with your hands, with your mouth. Good boy, now apply that to your sore little pink puffy asshole. It’ll help it heal. Do it yourself when you get to your room and then again before you go to sleep. Come to see me when Ben does, ok? I want to make sure that I’ll be able to use your cute little hole again soon. Maybe next time I’ll cane you while you’ve got the beads inside!”
She began to herd the boys out the door, one crawling on his hands and knees and the other walking with a pronounced limp. They walked across the hall to their apartment and Katy remembered one last batch of orders she needed to give.
“Ah, right! You won’t remember anything that happened that involves me or my orders even as you follow them! You won’t know where your aches and pains came from, and you won’t think hard about it at all! And you’re not allowed to cum at all. If you try to masturbate, all you will be able to do is get right to the edge of an orgasm before twisting your balls in your fist and slapping your cock! Then you will put and ice all over your dick and balls until your erection is gone. Ok, Good night you two!”
And then she slammed the door.