Anal Stretching Stories

Anal Stretching Stories

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by stretchingfiction
on Mar 4, 2021

by stretchingfiction
on Mar 1, 2021

by britisha_luvs_anl
on Sep 26, 2017

by EclecticDiversity
on Sep 16, 2017

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The Lord God our perverted creator didn't actually rest on the 7th day, it masturbated. For some reason the church doesn't want you to know that god becomes a horny freak when its got the hormones coursing through its divine body and it decided to create a copy of the universe except for one small change; People were far more stretchy. Unknown to the people...

One day The world was exposed to nanomachines made by an evil scientist and the rules changed for everyone on earth.
The first rule that changed was that No could a woman say no. Every person was perfectly healthy thanks to the Nanos. and even women to their 60 look like they are 20 again.
The second was that it hyperstimulated all men. They had a mental sug...

Michael sat in the chair as she entered. Powerone had described her perfectly, long black hair, green eyes, pale skin, very small hands and fingers, DD breasts and small hips. She had a gothic look to her, the black clothes standing out dramatically to her white skin.
"What am I doing here?" Violet questioned, but she already knew the answer. Powerone had o...

Before you start your challenge, you need to determine who you are...What's next?
Male
Female
Neither
What's next?
Male
Female
Neither...

So my story begins when I was exploring an old antique shop on the west coast. It was one of those disorganized and dirty older shops. With the dust thick in places and cobwebs clinging to everything out of reach. Had mostly seen the usual junk when an old trunk caught my eye. After haggling with the old shop owner I was able to get him down to 50 and he jus...

Disclaimer: The following is a work of pure sexual fantasy and is intended for adult audiences ONLY. If you are under the age of 18, please stop reading NOW and go tell your parent and/or guardian that you need stricter internet supervision. Any physical resemblance to a real person that any fictional character herein may bear is probably intentional and is...

Author's note: This is a work of fiction. All characters are eighteen years or older. Don't expect realism and you won't be disappointed when you don't find it! Enjoy!
*****
Even though he didn't attribute any strictly transcendental meaning to it, Sunday still felt somehow sacred to Nick. It was the day when he allowed his lazy side free rein, the mornin...

by britisha_luvs_anl, nastilatinabitch, & buxom_lesbian_slutmom1
NOTE: WE suggest that you read the FIRST TWO CHAPTERS, in order to understand
what's going-on in this third installment.........
Harriet Burnside, our mega-stacked main character of this series, has been summoned to the office of Irinia Kalenko, her department's Head Nurse and lesbian butt-b...

All night I had been teased. Pics of her masturbating, fingering her sweet pussy. Penetrating herself with the dildo and, finally, the mirror pictures, with the large fleshy dildo buried in her tight ass.
I'd been ready to blow five, six hours ago, even before those pictures, but they took me to a whole new level of turned on.
The pictures alone would've e...

By Patty Parker with Karin & Karinna Parker
*ALL CHARACTERS ARE AT LEAST 18 YEARS OLD OR OLDER*
Part 2 in the Series: Lesbian Incest/Anal/Strapon/
A few days later...
Della finds herself in a familiar position, one she always feels a bit awkward in: on hands and knees, knees spread widely apart. As Andy climbs onto the bed behind her, that nagging little...

I have a confession to make. I like to make people suffer. Most of them have it coming. Call me a sadist or whatever. It's simply my hobby. John is my name. Just call me the Anal Scourge. I'm a big and tall, wealthy and powerful Black man who likes to have his fun. Have you ever humiliated someone? Completely destroyed them? It's something I do everyday and...

NOTE: WE suggest that you read the FIRST TWO CHAPTERS, in order to understand
what's going-on in this third installment.........
Harriet Burnside, our mega-stacked main character of this series, has been summoned to the office of Iranian Kalikow, her department's Head Nurse and lesbian butt-buster extraordinaire. After being confronted with the evidence of...

Nothing makes me orgasm harder than when something's in my ass. I'm not picky. A butt plug, a dildo, my own fingers, a pen. Whatever I could find, I'd use to stretch my hole and get myself off. Even thinking about stretching my asshole made me wet. I loved everything about it, the slight discomfort, the pleasure, enveloping around whatever object it was. It...

He sat in the chair, naked except for a leather cock-ring that separated his balls, holding onto this thighs, so that his ass was totally exposed and puckered up, waiting for her kiss. She was in her endless teasing mode; as much as he loved it, she needed to do this more than his desire. Annie was 5'4", 38-25-37 and the most natural of Redheads – Nature's M...

I get home a little later than expected but none the less home! The house is quiet as I walk in, lights dimmed and faint music in the back ground. I knew I was in for a long night as I was warned not to be late. I was sure you gave me these deadlines knowing I would never be able to make them, yet every time I agree. I make my way through the house to the be...

I spent several weeks working in our basement, creating our own fun room. There already was a small room build at the back of the basement that was perfect. About 12 foot square and no windows, this would be the perfect place for me to design and furnish a room dedicated to kinky sexual activities. Once everything was set up, I asked my beautiful wife Nica i...

Introduction
Up to now, all my stories have been fact-based from my earlier life. This is my first attempt at pure imagination. All characters (or websites) are fictional, any similarity to real persons, living or not, are purely co-incidental.
*****
Gerry was bored. Bored with his job, bored with his succession of girlfriends, even bored with his compute...

Erin slowly opened her eyes. She was in her own bed but couldn't recall getting there; however, she was just glad she was awake now and no longer having that horrible nightmare. She had no idea what time it was, but it was still dark outside. As her mind began to clear she realized how sore her entire body was. Her tits and nipples were very tender and painf...

My wife and I were laying around one night and we tossed around ideas that we thought would be a good sex scene to play out, possibly video and save for posterity. We were hoping to post it on one of those internet sites and see what people thought of it. Hopefully we would get good comments. Some of the ideas were plain old sex stuff but some ideas were pre...

CHRONICLES OF THE "SPECIAL" YOGA STRETCH
My boyfriend/ live-in lover/ best friend of three years had mentioned anal sex many many times. We had tried it 2 or 3 times and had to stop because it was VERY painful for me! A few weeks ago, I had a short discussion with him that I didn't know if we'd ever be able to have anal sex unless I went through some "anal...

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The church prepares a girl's anus for her boyfriend.
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A short story about a man's decision to have his girlfriend's anus stretched by an agent of the Secular Church of Acceptance.
Set in the world of my novel, Rise of the Church: Zadie's Journey.
The church featured in this fictional story is a fictional organisation.
This story is pure fantasy and I condone only safe, consensual sex in real life.
'How many times do I have to say no ?'
'I really wish you'd try it. Just once!'
'No!' she said, forcefully, though she couldn't help but smile at his persistence. 'It must be so painful; there's just no chance I'll ever let you put anything in there.'
'I've read that loads of women actually orgasm from anal. Maybe you--'
'Nothing! You could buy me a yacht and I still wouldn't do it.'
'Don't you get bored of having it in the same old hole?'
Max sighed, defeated once again. After half a year of pleading and begging, he had made no progress. He had been toying with the idea of getting the church involved, but he was sure that she'd dump him if he did.
She returned her attention to the TV. 'Can we continue watching this now?'
'You're actually watching this shit?'
'I might sit upstairs and do my own thing.'
'No,' he laughed, 'I just have some work to catch up on.'
Retiring to the study, Max guiltily reflected on the fact that he did indeed desire to punish her for her annoying lack of compliance. He wondered how willing he was to risk their relationship. If she left him, he would at least have the exciting prospect of finding someone more obliging. After all, they had not been together for so long, so they weren't too inextricably tied to each other.
He stared at his phone, amazed that he was actually considering it. He came to his decision. Accessing the website of the Secular Church of Acceptance, he found the relevant number. He listened to the TV downstairs and was satisfied that the daytime drivel would provide sufficient cover. His heart pounded as he quietly eased the door shut and returned to his phone. He called the number.
'Good afternoon, I'm Lilly, and you have reached the anal stretching service of the SCoA. How can I help you?'
'Hi, I was wondering if I could book an appointment,' said Max, his voice hushed. The pretty voice on the other end of the line added to his nerves; he had heard that the convent girls themselves operated the phones, so the voice probably belonged to a gorgeous young woman in a sexy little church uniform.
'Of course, sir. Would you like to visit your local anal stretching centre, or would you prefer that we send someone to you?'
'Yeah, if you could send someone to me, that'd be great.'
'That'll be no problem, sir. Can I ask who you're calling on behalf of?'
'Okay, so as you're not married, we do need to know that she consents to the procedure.'
Max hesitated. 'Yeah, she's actually the one who suggested it.'
'That's great, we love to hear of willing volunteers outside the church!' There was a pause. 'Can I just confirm that she's over eighteen?'
'And could you briefly tell me why she requires the service?'
'She, uh, she's too tight to, you know...'
He imagined she was smiling. 'Yeah.'
After taking his address and some other details, Lilly confirmed that an agent would visit his home the next day. She wished him well and left him to dwell on what he had just done. He felt a little queasy as he weighed his options: he could tell her now or he could let it be a surprise. He knew the latter was the surest path to a turbulent breakup, but his cowardice won the argument, and he resigned himself to the fallout that was to come.
Another tedious game show was on the television. Max checked his watch frequently, paying no attention to the barrage of trivial questions and answers.
'You okay?' asked Annie, obviously irritated by the repetitive movement.
'Just bored of this,' he replied, wishing he could better control the edge in his voice.
'You've seemed distracted all day. Are you up to something?'
'What do you mean? That's a weird question,' he said, acutely aware of how defensive he sounded.
'Are you still annoyed at me for not doing anal?'
'You were acting funny last night, too.'
'Well, if you've got nothing to hide, then I'm sorry.'
They sat in silence for a long while, and Max resisted the urge to glance at his watch. The tension between them remained, and he cursed himself for allowing the mood to sour at such a critical moment.
'Annie, I need to tell you something.'
'I know you're going to be pissed off, but just--' He jumped when the doorbell rang.
Max felt paralysed. He couldn't bring himself to get up.
'I'll get it then,' said Annie, rising from the sofa.
Annie opened the door. 'Can I help you?'
'Hello, I'm Stefan, and you must be Annie?'
There was a pause. 'Shall I come in?'
'Oh... would you prefer to have your procedure out here?'
'Sorry, do I have the right address? I'm supposed to--'
'Yes, you're at the right place,' said Max, approaching the door. 'Come in.'
Annie glared at Max as the stranger began unpacking his briefcase. 'What's going on, Max?'
'He's from the SCoA,' he said, bracing for her inevitable fury. 'He's just going to help you--'
'What, help me satisfy your stupid need to put your cock in my arse?'
'Calm down, this is getting embarrassing.'
Annie let out a short laugh. 'Are you kidding me? You're embarrassed?'
Max gave their visitor an apologetic look. 'Sorry about this.'
Stefan offered a tight-lipped smile, apparently content to wait for Annie to acquiesce. He was holding some sort of restraints, and he had a variety of objects ready to put inside her.
Annie was beginning to look frightened. 'Max, seriously, this is--'
'Just give it a go,' Max insisted, attempting a soothing voice. 'He can stop if you don't like it.'
'Would Annie like to sit on the sofa?' Stefan prompted, detecting a softening of her demeanour.
Max took her arm and gently but firmly sat her down. She made little effort to resist, but she was obviously not happy to be manhandled. Stefan grabbed her leg, making her jump, and lifted it until her knee was touching her chest, exposing her shaven vulva under the hem of the tiny dress that Max had asked her to wear.
'Would you mind holding her other leg?' asked Stefan as he fastened a cuff around her leg.
With some trepidation, Max took his girlfriend's slender leg and folded it against her body. He was surprised to encounter no resistance and wondered if she might secretly harbour some desire after all.
'I can't believe this is happening,' Annie whined, as though reading his thoughts.
Ignoring her complaints, Stefan wrapped the bonds behind her back, holding her legs in place, and began to apply a cuff to her free leg. He bound her wrists either side of her head, seemingly just for the enjoyment of it.
'Is this necessary?' said Annie as the man completed her bondage with a collar, securely linking her neck and her limbs.
Her anxiety enhanced Max's guilt as his penis twitched in his trousers. Tightly fettered, she looked so vulnerable and helpless, and it disturbed him how much that turned him on. He simultaneously wanted to comfort her and ram his eager cock inside her.
'We have a policy of restraining the less compliant clients,' said Stefan. 'It ensures your safety and mine.'
'If I promise to be compliant, can I be untied?' asked Annie, attempting a placating smile.
'It'll be best for you to remain restrained,' he said, dismissively. 'Sir, you might like to stimulate her vagina to help put her at ease.'
'Oh, sure,' said Max, hesitating for a moment before placing his hand on her naked pussy.
'I'm afraid you will remain as you are,' Stefan interrupted, casually shifting her little dress so that it bunched up under her chin, exposing her lovely chest.
Annie looked incredulous. 'What are you--'
'I will begin very small,' said Stefan. 'Just a finger.'
Absently rubbing his girlfriend's clit, Max watched the agent of the church insert a digit into her puckered anus. She squirmed and grimaced, but he was sure that it was merely for show -- a protestation.
'Feel free to enjoy her breasts,' Stefan suggested as his finger slid in and out.
Annie gave a derisive laugh. 'What, do I have a choice?'
'I guess not,' said Max, taking a good handful of her soft flesh.
'I think there's room for two,' said Stefan.
Annie hissed theatrically as the second digit entered her, and Max watched with fascination as her tight orifice enveloped the intruders. His urge to be inside those forbidden depths was stronger than ever, and he desperately hoped that, by some miracle, she would stay with him and allow him the pleasure.
'Don't stop pleasuring her,' Stefan reminded him.
'Sorry, just got distracted,' Max replied, recommencing his lazy hand motion.
'Hmm. She's a bit dry,' Stefan observed, poking a fingertip into the unoccupied pussy. 'Use some of this.'
'Thanks,' said Max, taking the proffered lube and squeezing it onto Annie's genitals.
Stefan allowed himself a grope of a breast as he worked her anus, and Max slipped a finger inside her freshly lubricated cunt. He marvelled at how easily he could feel the stranger's digits sliding around on the other side; the separation between the two passages felt diminutive and delicate. Annie was breathing slightly erratically, and she had closed her eyes as though attempting to inwardly retreat from her torment while surrendering her body to the whims of the two men.
'I'll just put her in a better position for the more invasive part of the procedure,' said Stefan, grabbing Annie's compacted form and rearranging her like an inanimate toy until her head was resting against the seat.
'Invasive?' Annie inquired, looking up at the agent through her now dishevelled hair.
'It's nothing too scary,' Stefan assured her, selecting a metal object from his briefcase.
'What is that?' She demanded, the fear seeping back into her voice.
'It's only a speculum. Just relax.' He said, lightly tracing a finger around the clenched sphincter, encouraging it to let him back inside.
'What's it for? Why do you need to--oh!'
The cold, unyielding shaft sunk inside, gliding into her rectum before she could object. Max watched as the man operated the device, slowly opening her anus and presenting a gape sufficient enough to peer inside her virgin bowel.
'Oh, that's horrible!' Annie whimpered as her sphincter wrapped increasingly taut around the unforgiving prongs.
'You're doing very well,' said Stefan, unaffected by her plight.
'Can't you use something else?' she begged, obviously embarrassed by the unwelcome sounds escaping from deep within her belly as she was opened up.
'We'll get to that,' said Stefan, rubbing her empty pussy with his free hand as though to soothe her.
'Sorry, I keep forgetting to do that,' said Max, sheepishly.
'How much wider does it have to be?' asked Annie.
'Just until it can fit an erect penis inside,' Stefan informed her.
'What, it isn't that wide already ?'
'Not quite. It needs to be the circumference of your boyfriend's--'
'You measured your cock for them?' Annie interrupted, directing more ire at Max.
'Well, yeah, that's what this is for,' Max replied. 'Is that unreasonable? You should be thankful that I didn't give them the measurements of my fist!'
'That's about it,' said Stefan. 'Would you like to look inside, sir?'
Max hesitated. His curiosity was piqued, but he would have liked to avoid further conflict.
'No, I'll have a look,' said Max, ignoring his girlfriend's derisive laugh.
'Feel free to explore inside there with your fingers,' said Stefan.
'Oh, okay,' said Max, glancing nervously at Annie before venturing a tentative finger.
'Yeah, su
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