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Bailey’s Bulls 01

3574 words | 1 |4.40

Teen sissy Bailey is fooled into getting fucked on a farm.

Teen sissy Bailey fiddled with the straps of her bag as she waited on the corner of the street. A mixture of excitement and nervousness warred in her mind.

Today, she was dressed in a cute powder pink dress with a peter pan collar that had delicate floral embroidery all around it. The flared skirt of the dress swayed gently in the breeze, exposing the tops of her white thigh high stockings, each with a pink bow on the back. She was wearing her matching Mary Jane shoes, her dark hair corralled into two fat plaits with white scrunchies on the ends.

Yes. Today, Bailey was wearing her girliest clothes and accessories in anticipation of a very important event.

See, even though Bailey always wore girl clothing, she didn’t really feel feminine enough. The hormones that she took from time to time had done a good job of stunting her height, and giving her a more petite, girlish figure, but there was something missing.

That something, according to several websites on the internet, was being dominated by alpha male men.

Sissify.net expounded the joys of being held down and roughly fucked by a bunch of dominant men who would fill Bailey’s boicunt with virile cum. Bailey couldn’t deny that the idea alone made her little 3 inch cock twitch and jump with eager anticipation.

Well, it was just Bailey’s luck that she found an advertisement looking for a willing sissy to service a few bulls for a month during the summer. Well, thanks to Sissify.net, Bailey knew that bulls meant strong, muscular black men. Exactly the kind of men that she needed to fully bring out her sissy nature as well as help feminize her. The advertisement promised food and lodgings for the entire duration so Bailey only needed to pack her clothes, text them, then show up at the appointed place and time.

Bailey had responded immediately, eager to finally be fucked like girls were. She packed all her most feminine clothes and her cutest lingerie, keen on getting her boipussy stretched out for the very first time.

Thankfully, she didn’t have to wait much longer.

A pickup truck pulled up to the curb and a tanned young man leaned out of it. He looked Bailey up and down.

“Bull service?” he asked Bailey, chewing on the end of his cigarette as he squinted at Bailey through his curly bangs.

Bailey nodded eagerly.

The young man looked Bailey up and down again, as if he didn’t think that Bailey could do the jobs, but then he snorted and nodded.

“Hop on in.”

Bailey eagerly went over to the passenger’s side and then got in.

– – – – – – – – – – – – – – – – – – – – – – – – – – – – – – – –

Like all teenagers, Bailey had seen a number of porn videos. It was the ones that featured limp dicked feminized boys that had tuned her into the fact that she also would like to become a limp cocked cum guzzling slut. She couldn’t help but think of those videos as the pickup made its way through the town towards the outskirts. Would they all fuck her at the same time? Would they make fun of her tiny little cocklette while they pounded her? How would it feel to have her cock limp and flailing about while they rammed their hard rods into her waiting asspussy? With all these thoughts floating about, it took some time before Bailey noticed that they had left the town entirely.

“Are we heading far?” Bailey asked, her apprehension rising.

“The farm is pretty out there,” the young man said, looking over at Bailey, “It’s more… private… that way.” He leered at Bailey, making the young sissy turn red. The way he was looking at Bailey made the young teen feel like a piece of meat. But instead of feeling horrified, she felt a wave of arousal. It was one of the things that made Bailey so certain of her decision to answer the advertisement. Only sissies enjoyed being objectified like this and made to service men, right?

Bailey squirmed in her seat, folding her hands over her crotch so that the driver wouldn’t see her little dicklette getting hard at the thought of being gangbanged.

Not long after, the young man turned off the main road, taking them towards a collection of buildings surrounded by trees.

“We’re here.”

Bailey got out of the truck and smoothed out her skirt nervously.

“The bulls are this way,” the young man said, leading her around the buildings.

It was a little strange that he wasn’t taking her to her room first, but Bailey shrugged it off. Maybe the men in question were in the back, doing farm related tasks?

Bailey rounded the corner and stopped short.

In two separate pens, were two large bulls.

Animal bulls. With large horns and flared nostrils, grunting as they moved over… over something.

No, not something…


Bailey stood there in shock, unable to believe her eyes.

Two young sissies were cuffed to a frame, their faces addled with what looked like pleasure and pain. Both of them were moaning around the gags in their mouths, their caged cocks limp under their bodies as the bulls pounded their boicunts relentlessly.

“Mmcmmming!” one of them squealed as the bull on top of her rammed into her ass. Her eyes rolled up into her head and she jerked in her bonds. Her friend soon followed suit.

Neither seemed to notice either Bailey or the young man who had brought her here.

“There’s been a mistake-” Bailey tried to say. She wanted to be fucked by a man, not an animal!

She backed away quickly, only to thump right into the muscular chest of another farm hand.

The tall, tanned Latino man grabbed Bailey’s wrists in his large strong hands and looked down at her.

“No can do, puta. You came to serve the bulls, you gotta serve the bulls,” he said with a cruel grin.

“No! Help!” Bailey screamed and kicked but to no avail. Her petite stature was no match for the experienced farm hands who quickly surrounded her and ripped her clothes off.

RIPP went Bailey’s cute pink dress, now nothing more than a rag in the dirt.

The men quickly manhandled Bailey over to a strange looking contraption. It was made out of metal bars, with rings for chains. Bailey found herself being bent over one of the bars, her arms stretched out and cuffed to the corners of the frames. Her legs were forced wide apart and secured in the same way, leaving her ass exposed for everyone to see.

“Please no please!” Bailey begged, but no one came to help her.

Tears poured down her fate as she realized she was about to lose her boicunt virginity to an animal!

“Let me g-mmmphghgh!”

One of the men took advantage of her yelling to stuff a cock shaped gag into Bailey’s mouth and buckle it firmly around her head.

She could only moan and whimper, watching helplessly as the horrible men moved around her and got things ready for what was sure to be a brutal ass-fucking by a bull!

“Get her caged up too, don’t want her to hurt herself!”

Before Bailey could process what that meant, one of the farm hands was approaching her with a metal device in his hands. He went behind Bailey where she couldn’t see and then-


Cold steel encased Bailey’s little cocklette and sac, compressing it until it was nothing more than a little nubbin! With a soft click-click, the cage was locked and the key, pocketed. Bailey shivered all over, fear and terror making her cry harder. She hadn’t been ready to embark on the chastity portion of every sissy’s journey but it was now being forced on her.

“Take her over to old man Angus! She’s gotta pay her homage to him!”

The farm hands came over and wheeled the contraption away with Bailey on it. They passed the pen where the two bulls were still mounting their sissies, heading for a much larger pen.

Which housed a much larger bull.

The name carved onto the sign proclaimed the meaty, muscular bovine creature to be Old Angus. He was taller, broader, and meaner looking than the two bulls that Bailey had seen earlier, his face covered in small little scars that had no doubt come from winning fights. If Bailey had thought the horns on the other two bulls had seemed huge, they had nothing on the massive pair that sprouted from the massive head of this creature!

Old Angust tossed his head and snorted, turning in his pen as if to scrutinize the morsel that was being brought to him.

“Don’t worry, sissy. Old Angus knows how to break in a hole!” one of the men laughed as they opened the gates and brought Bailey inside.

“Mnnhg ommmmmghppph!” Bailey wailed into her gag, struggling against the metal cuffs that kept her spread wide and helpless.

Old Angus had a massive set of balls that swung as he moved around. In front of those balls lay a thick low-hanging sheath where a pinkish red cock had begun to emerge.

Bailey screamed in terror, the sound muffled by the silicone in her mouth. She struggled harder, trashing around in hopes of dislodging herself, damaging the contraption, anything to get away from this nightmare!


The men who were transporting her landed a volley of blows across Bailey’s upturned ass, making her howl in pain.

“Stay still, sissy! If you struggle we won’t slick up your hole!” one of the men growled.

Bailey froze in place. Her limited exploration of her body had taught her that fingering her hole dry was a recipe for disaster. Of course, like every other sissy, she dreamed of one day being able to take a cock with minimal lubrication. But was to be in the future. Perhaps even a distant future. Not now and certainly not for her first time!

Terrified of being ass-fucked dry by the bull, Bailey could only stop struggling and sob quietly instead.

There was the sound of a cap being popped open, then a nozzle pushed into Bailey’s virgin boicunt. Something cold, slick, and slimy was squirted right into Bailey’s sissyhole, followed quickly by a rough and cruel fingering by one of the men.

“Smile for the camera!”

Someone grabbed a fist of Bailey’s hair and yanked her head upwards.

She whimpered, looking into the lens of a handheld camcorder. The young man who had drove her here was holding the device, looking down at her with a cruel expression on his face.

“How does it feel, sissy? Knowing your first time is going to be taken from you by an animal?” he laughed cruelly, “He’s going to break your virgin hole completely!”

Tears coursed down Bailey’s face. This was happening and she was powerless to stop it.

“Look at this fresh teen sissy. She’s about to get her shitter split wide open by old Angus!” the man moved away from Bailey’s face and pointed the camera at her body instead, panning all the way down to aim it at her caged little cocklette.

“Let’s see how many times Old Angus can make this sissy cum!”

Bailey felt her contraption being moved again. The men placed blocks around the wheels to keep it steady, then backed away.

With a loud snort, Old Angus stomped his foot and then trotted forwards to inspect the newest offering. The hot breath of a seasoned bull rushed over Bailey’s exposed bottom as he sniffed her thoroughly.

Satisfied with what he found, he reared up onto his back legs and mounted the frame.

Old Angus had fucked countless females. Some of the cows, some of them not. During the mating seasons, he was accustomed to mating with many cows in a day. But then it was not mating season, the humans brought him these pale, squealing creatures for him to mount over and over again. Old Angus wasn’t picky. If they smelled ripe, he would rear up onto the frame and plunge his cock deep inside whatever hole was waiting for him. He was so experienced that it didn’t take long for him to find the tiny, tight opening of the pale, whimpering creature under him. Without wasting any more time, Old Angus thrust his powerful hips forwards, ramming his thick bull cock into the small hole.


Bailey screamed in agony as her virgin asspussy was brutally split open! Tears streamed down from her wide open eyes, her dainty fingers curling and uncurling as her young mind struggled to comprehend the pain in her bottom. As tight as her untouched hole was, it was not a match for the experienced fuckpole of a muscular beast like Old Angus. The bull thrust over and over again, driving his thick rod deeper and deeper into Bailey’s sissyhole.

Around the poor little pansy, the farm workers cheered. Some of them had pulled out their cocks, jerking themselves off lazily as they watched Old Angust destroy Bailey’s shitter. To make things worse, Bailey’s cocklette began to twitch. It jerked every single time the bull rammed his cock into her boicunt. Bailey wailed when she realized what was happening – Old Angus’s cock was so thick that it was mashing Bailey’s prostate, making her little tic tac try to get hard!

“There she goes!” someone cheered.

Bailey went red with humiliation. Piss jetted out from her cock as her bladder was compressed by the massive cock inside her. It was swiftly followed by precum, squeezed out by the bestial fuckpole that was currently obliterating her boicunt! Every thrust was a dizzying mix of agony and pleasure. The pain of having her virgin asspussy busted wide open warred with the arousal that came with having her prostate hammered in such a firm manner.

Pain, pleasure, pain, pleasure, the two blurred into one as Bailey’s sissyhole surrendered completely to the bull’s cock.

“Mnnnhgh…” Bailey moaned when the confusing mixture of sensations came to a head. Her body had been so tense, so taut like a tightly pulled guitar string, but the string had snapped. She didn’t know if it was the agony or arousal that made her cum, but she was cumming. Bailey’s asspussy began to convulse, squeezing and massaging the cruel invader that was still pounding it viciously. Her caged cocklette twitched pathetically in its cage and spurted out a few ropes of cum onto the dirt under her. Bailey’s whole body shook and shivered as she experienced her first ever painal sissygasm on a bull’s cock, surrounded by lecherous men who whooped and cheered at her humiliation.

There was no respite for the poor teen sissy.

The bull continued to pummel her helpless hole, bellowing loudly as he drove his massive rod deep with each thrust. Each time the meaty fuckstick slammed into Bailey’s freshly devirginized hole only seemed to prolong her tortured sissygasm. She had heard about the wonders of prostate orgasms before, of how sissies easily came from having their P-spots massaged. But never had she thought it would be like this! Her bladder and prostate must have been mush by now, completely flattened by how much space Old Angus’s cock was taking up inside her petite body. But despite the discomfort, her body continued to shiver and shake, shuddering through what felt like an endless painalgasm. Each time she thought it was over, the bull would fuck deep into Bailey’s body again, crushing her prostate and making her cum again!

Bailey lay on the frame limply, moaning weakly as sissygasm after sissygasm wracked her entire body.

It felt like an eternity before the movements slowed down and then she felt something gush into her boicunt.

Bull cum, Bailey realized a few seconds later. It rushed into her bowels, hot and scalding, filling her asspussy up rapidly.

Tears began to form in her eyes once more as she began to realize the depths of depravity she had sunk to.

Not only had Bailey’s virginity been taken by an animal, she pissed herself and cum multiple times from the pain of having her boicunt destroyed by his thick cock. Now, he was filling her body with his sperm, breeding her like she was just another cow. And all this had been filmed by the workers on the farm.

Grunting, old Angus shook his head and dismounted. Bailey moaned as his massive rod vacated her asspussy with a loud squelch. The seasoned bull stuck his snout between Bailey’s asscheeks as if to inspect his work, gave an approving wheeze, then stomped off to the other side of the pen.

Bailey lay on the frame, shivering and crying as the magnitude of what happened started to sink in. Her once tight and virginal sissyhole had been completely broken apart by the bull’s massive cock. It had forced its way inside her and completely remolded her shitter to accommodate its girth. Her boicunt gaped wide open, unable to close at all. Her prostate and bladder felt bruised, crushed by how the animal’s meaty fuckstick. Her body still spasmed a little, remnants of the repeated unwanted painal-induced prostate sissygasms. There was no coming back from such an experience.

Bailey was a changed sissy now.

One of the men opened the gates.

“Go clean her up.”

Bailey didn’t have the energy to turn her head and see what was going on. She was still full of self-pity, regretting that she had answered the ad at all!

She jerked when a soft hand touched her back and the sissy she saw earlier came into view.

The other sissy was a pretty blonde girl with two pigtails. She had pretty green eyes and a cute little pout. Her tits were of a decent size, both nipples pierced with miniature cowbells hanging off them. She also wasn’t wearing anything but a steel collar around her neck and a flat cage that inverted her cocklette.

“Hey hey, it’s okay,” the sissy said softly. She kissed the top of Bailey’s head gently and then wiped her tears away.

Bailey squeaked when she felt two hands prise apart her asscheeks. Before she could jerk away, a soft wet tongue began to lap around Bailey’s ruined sissyhole, soothing the ache there.

“Being fucked by Old Angus sure is an experience, isn’t it?” the sissy said gently, undoing Bailey’s gag and using a rag to wipe the snot from her face.

“Please please let me out,” Bailey whimpered pathetically. Her words soon turned into a moan as the person behind her worked their tongue into her ruined shitter, tickling the inside of her rim.

“No can do, sister slut,” the sissy said, crouching down in front of Bailey, “If Armand says you gotta stay, then you gotta stay.”

She sounded apologetic, stroking Bailey’s hair with a look that said she understood all too well what it felt like to have her asspussy broken by a virile beast.

“Please, please don’t do this to me,” Bailey begged.

The sissy shook her head, “You still have to say hi to Tank and Rocky,” she said, jerking her head at the other pen.

“No, please! My ass can’t take anymore!” Bailey wept, snot dripping from her nose.

The sissy tutted and stroked Bailey’s hair.

“You and I, we’re sissies, our holes were meant to take cocks,” she said softly, patiently, “You’ll understand soon.”

She shoved Bailey’s gag back into the teen’s mouth and then straightened.

Bailey watched in horror as the other farm men approached her and began to move the contraption.

“Mnngh mmmnhgh!” Bailey’s muffled screams were lost on the large farm, ignored by the men who pushed the fuck frame over to where she had seen the two young bulls earlier.

“There we go,” one of the men said with satisfaction, locking the frame into place.

He whistled, getting the attention of the two bulls. They came over, snorting and huffing, interested in the new pale pink thing their caretakers had brought.

“Have fun, sissy!” the men laughed and chuckled as one of the bulls reared up onto the frame.

Something hot and thick pressed against Bailey’s sissyhole. She wept, knowing that she was helpless to stop the breeding that was about to happen.

“Mmmnnngh, mnnngh mnngh!” Bailey’s moans quickly began to alternate between pain and pleasure, the confusing sensation of cumming while being stretched to breaking overcame her young body and she shivered under the powerful pounding of the beast.

Unable to escape, the poor teen sissy could only lie there and wait for her ordeal to be over.

[A/N] Life is getting in the way. I’m still writing, but very slowly because of financial and health issues. I kind of lost passion for some of the series, but I do plan to finish them some day. Thanks for reading still ~ kinkbugs.

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1 Comment

  • Reply RANDOM2 ID:4bn00en3fia

    This might be the best story in this whole app