Anal Sex Punishment Stories

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by alternatereality08
on Dec 18, 2019

by alternatereality08
on Feb 23, 2021

by Alex_likes_Butts
on Sep 12, 2017

by delicatedarkness
on Nov 26, 2017

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Soap has long held a special place among the punishments imposed by mothers to punish misbehaving offspring of all ages. It also proves to be an excellent option for governesses who are responsible for disciplining charges of all ages. Here we are only considering its use with those who are 18 years or older. But as with many traditional nursery punishments,...

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...

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...

This story does involve bodily functions so if that is not something you find compatible with your interests, read no further. It features spanking and caning, so has been placed in the BDSM category but has equally significant Fetish contents. All characters are over 18.
*****
Melody Haynes, in her early 50s, awakened and was surprised momentarily to find...

Fiction Experiment Chapter 1
She had tried the online spanking personals but found only a lot of men interested in imposing their own (usually physically improbable) fantasy. What she wanted - needed - was erotic punishment and the humiliation of it being witnessed, critiqued ... and added to. She needed her limits pushed and exceeded.
So she decided to...

The name is Kyle Jamal Francisco. My close friends and favorite family members call me K.J. I am the villain of this story. Who am I? In the eyes of the world, I am a tall, good-looking young black man currently living in the city of Brockton, Massachusetts. What is my profession? I'm a part-time Criminal Justice student at Bridgewater State College and a fu...

This is a series of stories about the impact of the new female teachers at the traditional school for boys 18 and over, Hamilton Hall, dedicated to preparing them for college but insistent on retaining corporal punishment. The school first hired Linda Crawford and now has both enrolled girls over 18 and brought on two more female teachers. There is some refe...

I was lying on my stomach recovering from a massive orgasm with Seamus' huge fat cock buried up my snatch. I could feel his cock pulsing and throbbing. I had just finished being driven through my second orgasm. The first one was almost simultaneous – I had started coming first and was writhing and screaming when Seamus, riding me hard, fired his load up my s...

Nick's cock slowly invaded the glossy pucker of Anne's anus then exited at the same pace. The sensual scene replayed several times and the warmth of her tight channel soon had him longing for more. Trying to ignore his lack of control over the maddeningly sluggish speed, he focused on his wife as she worked her ass up and down his length. With both his wrist...

Dear Penthouse,
I'm writing this letter for your forum because I have been ordered to detail one of my spanking sessions on paper as part of my punishment. I'm a slender Asian male, 19-years-old, with light creamy complexion and very smooth body. Several weeks ago I made the mistake of shoplifting at my spanker's store and was caught red-handed. As a conseq...

A/N: Please suspend your disbelief for parts of this story. I know a lot of it isn’t realistic or possible, but it’s just a story. It’s likely that many of the insertions that will be written are not possible in real life and should not be attempted.
In a world similar to our world, the expectations for women are very different. Women are expected to have a...

[This story involves bodily functions and sometimes severe disciplining, including caning and spanking, as well as crossdressing. If reading about those offends you, read no further. These stories may be read separately but do gain from being read in sequence.]
Laura Franklin wasn't sure what kind of response she would receive when she sent out notices by m...

[This story contains a good deal of content relating to bodily functions. If that offends you, please read no further. All characters are well over 18. ]
***
Plans proceeded for Eleanor and Annette to be married. Because of her previous notoriety, Eleanor did prefer to keep her activities out of the public sphere, as did Annette, who recognized that her ca...

After fucking me in the shower, you hug me tight against your body for a few more minutes before pulling out of my well-stretched asshole. I enjoy the feeling of my soft bare back and buttocks pressed tight against your well-muscled body. Then you uncuff my wrists and let me rub my still red asscheeks for a minute. I know you enjoy watching this naughty chin...

If you like inter racial and anal, you may enjoy this short story. All characters are fictitious. This has the same basis, but different outcome to the first Jala's Punishment.
*****
If there was one thing I had never tried, it was anal. In a sexually active life from late teens through twenties and into my thirties, I had enjoyed quite a variety. I had be...

In a place known only as the Discipline Society, the government created laws that allowed for the corporal punishment of women under the age of 40. This decision came about due to a belief that younger women were not mature enough to act obediently on their own.
Specifically, the law allowed organizations, such as schools or companies, to punish women who br...

Two days later, Stephanie was again slip shod in her approach to her master and he decided that this time she was going to be really humiliated. So he arranged to meet her in the centre of town and lead her through a succession of back streets till they reached a pet shop.
The took his little cum slut inside the shop and he whispered that she should go sele...

My sexy 32-year-old girlfriend Ashley was dressed in a form hugging pleated grey skirt that came down to just above her knees, a white blouse and some nice black "fuck-me" style boots. God, did she look gorgeous this evening! For added effect Ashley gathered up her long black hair into a ponytail, giving her the look of a wholesome good-girl next-door type....

Author's Note: To the people who constantly appreciated and asked for more, the third part is for you guys. A big thank you for all the love and support. Please let me know in the comments if you have liked reading the story.
Day TWO.
The following day, Grace woke up a little later than usual and found a sticky note beside her bed that read—"Your breakfast...

"...Figging is the practice of inserting a piece of skinned ginger root into the anus or the vagina of a person. It has been used as a means of punishment. It is also used as a BDSM practice." - Wikipedia
Figging. Where one person voluntarily chooses to have ginger stuck up their butt (sometimes their vagina - but more often than not, the butt.) Chewing can...

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NonConsent/Reluctance Anal Punishment for Daughter
A college demands action against a failing student.
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This story is pure fantasy and features themes of NON-CONSENT/RELUCTANCE and FATHER-DAUGHTER INCEST. Continue reading if you enjoy these themes.
I condone only safe, consensual sex in real life.
Set in the world of my novel, Rise of the Church: Zadie's Journey (recently republished).
The church featured in this fictional story is a fictional organisation.
Lola was engrossed in her social media as she stepped into the house. She didn't need to take her eyes off her phone as she removed her shoes, but she did need to look up to peer into the fridge.
She jumped when she noticed her father glaring at her from the side of the kitchen. 'Oh, I didn't see you there, dad!'
James held up a piece of paper. 'Lola, this says you failed your last exam. Have you been skipping college?'
'No, of course I haven't! It was a really hard exam!'
'I pay a lot of money for you to study there.'
'I'm trying really hard -- I'll try harder!'
'You've failed the last three now. What on Earth are you doing?'
'I don't think you have a reasonable excuse,' said James, approaching his daughter and looking her up and down. 'Do you just put that uniform on in the morning to dupe me? Do you hang out in town all day with your mates?'
Lola's college had been taken over by the Secular Church of Acceptance that year, and they had enforced the wearing of a uniform. It was similar to one worn by novices in the church's convents, consisting of a cropped, zip-up jacket with a hood, a short skater skirt, and a pair of high heeled shoes. The little jacket was made of a soft, satin material with a lustrous sheen, and bras were prohibited. It was clear to see that Lola was complying with that rule, as her nipples -- cold from the outdoors -- protruded beautifully beneath the thin fabric.
'I can't believe you'd even suggest that,' said Lola, making to storm off.
James grabbed her arm. 'Look, Lola, the principal wants to expel you.'
Lola stopped and stared at him, aghast. 'What? They should be helping me, not kicking me out!'
'The letter says they'll only let you stay if I punish you.'
'So... what, ground me? I'm eighteen.'
'No. They want me to punish you with...'
After a stunned pause, Lola laughed and took the paper from his hand. As she read, her expression morphed into one of incredulous disbelief. 'He wants you to record it? What the hell?'
Lola leaned against the worktop, reading through the letter over and over.
James continued. 'If you got expelled, I don't think you'd be accepted into another college.' He paused but received no response. 'It's up to you.'
Lola shook her head, letting out a loud exhalation. 'This is insane. This could never have happened before the SCoA took over.'
'I don't think I have a choice if I want a future.'
James had to conceal his excitement; he had harboured secret fantasies about his daughter for a couple of years now, but he had never dreamed that they might become reality. He had watched her transform into a beautiful young woman, and he had been particularly curious about her blossoming breasts which always remained tantalisingly just out of sight under her sexy little uniform. He had only been able to catch fleeting glimpses of under-boob when she had reached up to a high shelf or bent over to pick something off the floor.
'I guess now is as good a time as any,' he said, feeling the blood pumping into his cock as he anticipated exploring his daughter's nubile body.
'I can't believe we're even considering it.'
'As you say, Lola, we have no choice.'
She went silent for a long moment as she stared out of the window. 'How do we even do it?'
'Let's keep it simple. You can rest your leg on the worktop, and--'
'You don't think we should go to my -- or your -- bedroom?'
'Don't you think that would be too, you know, like we're lovers?'
'I'm sorry to ask, but I'll need you to help me get to a full erection.'
'Have you ever put something in your bottom?'
'You need to understand that it will hurt a lot unless I am as hard as I can be.'
'And that means I have to give you a blow job?'
'Oh my God.' Lola put her hands over her face and rubbed her eyes as though she had just awoken.
James unzipped his fly and pulled his semi-erect penis into view before gently pushing his daughter to her knees. 'Take your time, Lola. No pressure.'
'This can't be happening.' She took a deep breath and closed her eyes.
James began to think that she wasn't going to do anything, but she finally opened her mouth and took the tip of his glans between her lips. He held his breath, his heart suddenly pounding, and her moist lips slowly crept towards the base of his shaft which pulsated as more and more blood coursed into it. She sucked it steadily, only taking half of it into her mouth at any time, but it was enough to send his senses into overload. He stared down in amazement as his rapidly expanding cock glinted with his daughter's saliva, and his mind raced with ideas for future punishment sessions.
'Can you take it deeper?' he said, fearing an indignant reaction but instead being rewarded with mute compliance.
Lola choked softly as her father's glans entered her throat, but she believed that it was necessary to help him achieve full hardness in order to ease his entry into her bottom, so she persisted, gagging repeatedly without complaint.
'That should do it,' he said, letting his throbbing cock spring out of her mouth and helping her up.
Lola seemed to be in a daze as he positioned her for her punishment. She didn't resist as he bent her over the worktop and pulled at her college-issued panties. As her freshly shaven genitals came into view, he stopped and stared, entranced by the awesome sight.
'What're you doing?' she said, finally able to speak.
'Nothing... just thinking,' he said, sliding the silky underwear the rest of the way down her long, elegant legs.
James lifted her leg onto the surface, keeping it straight so that the two slender limbs formed a ninety-degree angle. He stood back to assess his daughter's appearance, trying hard not to fixate solely on her exposed genitals which were so perfectly framed by her little skirt. He gripped the back of her neck and pushed her firmly against the worktop before arranging her luxuriant hair to maximise its aesthetic appeal.
'Why are you doing that?' she said.
'The better you look, the more lenient the principal will be,' he said as he neatened the hood of her silky jacket. 'It's difficult to stay mad at a pretty girl when she's making an effort.'
James smiled as he adjusted the position of her stilettoed foot on the worktop to splay her legs a little wider. 'Yes, I think you're stunning.'
His cock was so hard that it ached as he fetched the camera and some lube. He placed the camera on a kitchen stool behind his daughter and carefully positioned it for the best view. He knelt to share its viewpoint and peered between her wide-open legs. He could see up her little jacket, but her young breasts were pressed against the work surface.
'Lola, move your torso this way a few inches.'
'Just so you're framed properly in the recording.'
As she moved, her breasts popped off the edge of the worktop and dangled enticingly; her nipples were still erect, begging to be pinched and tugged. James took another moment to gaze in awe -- every inch of his girl was a delight to behold.
'Sorry, Lola,' he said, applying some lube to his urgent phallus and setting the camera to record. 'Yes, we're all set up.'
Lola made a little whining noise as the tip of her father's cock tickled the sensitive skin around her sphincter. She squeezed her eyes shut as he pressed against her anus, and he stroked her hair to offer some comfort, tenderly tracing her ear as he brushed a strand behind it.
'You'll have to relax, Lola, or I won't be able to enter you,' he said, applying more pressure.
'It feels like an elbow trying to get inside me!'
'You'll be surprised what you can fit in there,' he said, rubbing her bottom and trying to soothe her with a soft touch. He pushed some more, but her anus was hopelessly clenched, and he began to believe that she was indeed unable to receive anal. 'I'm just going to try something.'
Lola gasped as he slid into her pussy, and her dad had to quickly grab her ankle to keep it on the countertop. 'Oh my God, what are you doing?'
'Just try to enjoy it,' he said, holding her down by the back of her neck. 'It might help you to relax enough for the anal.'
'You can't put it in there -- you're my dad!'
'I'm not going to come, you don't need to worry,' he said as he bored into her belly and felt her pussy squeeze his invading shaft in protest.
'It's just wrong, though!' she said, trying to push herself off the worktop.
He persevered with his probing exploration of her most intimate place, pinning her down until she stopped struggling. When he finally let go of her ankle, she didn't attempt to move it off the countertop, and he knew that he could trust her to behave.
'You know this is for your own good, don't you?'
'The letter didn't say you had to put it in my vagina,' she said, jolting forward each time her father thrust into her.
'Sometimes you have to think outside the box,' he said, pulling out and plunging it into her anus with one swift movement.
Lola shrieked and had to be restrained again. Standing on one stilettoed food, she was unable to offer much of a fight, and James easily held her in her prescribed position.
'You'll get used to it before you know it,' he said, standing still with the first inch or two of his solid cock inside her as he waited for her anus to slacken.
Her wailing eventually reduced to a feeble whimpering, and James felt he could continue. He slowly sank his eager phallus deeper and deeper until his entire length occupied his daughter's bowel. Her freshly stretched anus -- unwilling to suddenly abandon its eternal defence of her innards -- gripped the intruder with furious tenacity, but its indignation was no deterrence, and the thick shaft soon commenced its task of reaming the newly conquered cavity.
Lola grimaced -- her cheek pressed against the hard surface -- and willed her anus to give up the fight. She resolved to be good and keep still to allow her father to carry out his duty, but the pain was refusing to recede quickly, and she began to doubt that it would ever go away.
'Dad,' she said, her voice sounding strained, 'how long do you have to do it for?'
James pondered the question. 'I'll have to prove that I was really inside you and not just pretending... I will have to ejaculate inside you and show it to the camera.'
Lola moaned. 'You can't be serious.'
'I'm sorry. Can I trust you to behave now?'
Lola stayed perfectly still as the thick shaft popped out of her stricken anus, and she felt a peculiar sensation as the cool air entered her bowel before her sphincter closed. The throbbing in her rear didn't subside completely while she waited for her father to fetch another stool. She looked back at him with confusion as he planted his foot on the stool, raising his knee as he took his position behind her.
'Why are you doing that?' she said as he prodded her puckered orifice.
'Just to give the camera a clear view,' said James, pushing her back down and watching her sphincter open reluctantly around his shaft as it recommenced its incursion.
In truth, his new configuration was designed to allow the de
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