Mom's Enema
by Mike McGifford
Copyright© 2026 by Mike McGifford
“No mom, you have to be naked for this,” Ray insisted curtly, holding up the nozzle like a pointer, as if he was the teacher and his mother was a little slow, not the grade school teacher she really was.
“Raymond! I don’t think your father meant that!” Jessica gasped at the idea of her son seeing her in the nude even as her fingers went to the top button of her blouse as if they had a mind of their own.
Jessica had always been a rule-follower and something about the way her son was acting, the tone of his voice, his impatience with her, his air of confidence, was causing her to wonder if she really was being silly, reluctant to undress in front of him.
Raymond had once already, Jessica decided, carefully explained that Jim wanted him to administer an enema and he’d only agreed out of the goodness of his heart. She knew she was rationalizing the outlandish request but things hadn’t escalated for her in almost a year and Master Dale’s expectations of her had seemed to plateau. She’d always known that wouldn’t last forever.
So this is how he’s going to push me, Jessica thought to herself. Using my own son despite my wishes that none of my children ever find out.
But then why start with a health routine like an enema? It wasn’t even sexual. If anything, cleansing a colon was anti-sexual and the only connection the procedure had to Master Dale was that he required them as part of her health and fitness routine. What made it stressful was only that for some reason Master Dale had orchestrated things so that her son thought he was doing his parents a favor.
Jessica knew her husband Jim had to have been given his marching orders by Master Dale and her loving partner of nineteen years had to have found it very challenging to make the request of his own son against her stated desire to leave the kids out of their games.
The questions were, would Master Dale expect to escalate once again, this time with one or more of her family members past a simple hygiene thing? The thought terrified her. Having her son present while she received an enema was certainly crossing some sort of line. Maybe it was Master Dale’s way of telling her he was getting bored of her? Was this a sign? Maybe their relationship was coming to an end and he wanted her to be the one to break it off? But Jessica was the happiest she’d ever been! She decided then and there that if Master Dale decreed it, she’d damn well do it!
As she pondered this, her thoughts turned to Jim. He was so much better at being loyal to Master Dale and Mistress Anne than she was.
Jessica thought again of the brownie she’d snuck after lunchtime despite Master Dale’s order that she not snack. She couldn’t even go a day without disobeying while Jim sucked it up and convinced his own son that she needed help with her enema. Jim might be a submissive too, but he was a more loyal one than her. That was obvious to her.
What Jessica didn’t know was that Raymond had received no such request from his dad. In reality, Raymond had only overheard a conversation between his dad and their neighbor and was acting on his own.
He’d heard Mr Parker tell his dad the day before that the time had come to challenge one of the things on Jessica’s no-go list the way Mr Parker’s wife had done with his dad the previous week.
Mr Parker warned his dad that he was going to prepare ‘Little Jessica’ to have her third hole opened. He bluntly told his dad that he was going to pop Jessica’s anal cherry so she could be more ‘available’ and that she’d need to give herself more frequent enemas prior to the occasion starting the next night.
He’d then heard his dad call Mr. Parker, ‘Sir’, before asking if he was required to be there every time or if ‘Mistress Anne’ would be, ‘looking after him’, as originally planned for the next night when they’d arranged for Jessica and him to entertain their guests.
Raymond’s mind had at first gone into overload as he maintained his secret presence and had since been working overtime processing the conversation.
He’d eventually concluded his parents were both subbies to their nextdoor neighbors and his mom was regularly passed around as a party favor for paying customers. His parents were wild! That realization had made Raymond wonder how he could benefit from this new found knowledge.
Could he possibly explore being a dom himself? Half his porn stash was BDSM clips and pictures and the only thing that had held him back was not knowing which of the girls at school he could trust to explore that world with him.
He knew instinctively that exploring with his mom would be a very safe way which wouldn’t get him in trouble with any of the girls at school if he could work things right. It wasn’t about sex, but about the exchange of power.
He truly wasn’t thinking of sex with his mom. He wasn’t averse to it, depite the taboo nature of incest, but that wasn’t his goal. He’d had sex before and it was okay. He knew without knowing how he knew, that sex would be amazing if it was with a submissive woman.
If it happened with his mom, he’d cherish the memory but that memory would revolve around it being sex with a subbie woman, not specifically his ‘mom’. The incest part held little extra draw, he assured himself.
His goal was to see if he could be dominant. To dominate someone who’d never blab about his desires to every other girl in school. To be in control of someone was the sexiest thing he could imagine and it didn’t matter to him that the woman could be his own mother. So he’d hatched his plan.
Mr Parker had said he’d be over to personally witness Jessica’s enema, so Raymond had simply beaten Mr Parker to the punch by arriving home from school, going to his parent’s bathroom and pulling out her enema kit so it was on hand when she arrived home from work, startled to find him there.
He hadn’t even had to convince his mom he was telling the truth. He just told her he’d been tasked with giving her an enema as if he did it all the time.
He’d loved seeing the confused look she’d given him before she’d blushed and asked him why he thought he needed to do that. He’d then simply told a white lie and said his dad had asked him to, as casually as telling her that Jim had asked him to mow the lawn.
“Are you sure about this, Raymond?” Jessica asked when her son didn’t respond to her comment.
“Look, mom. I’ve got a job I promised to do. I don’t know why dad said you need help or why it had to be done in the kitchen where the girls could catch you if they come home unexpectedly but I postponed my plans and I do intend to keep my promise.”
Raymond had crafted his explanation to make his mom think her Master had given special instructions like doing it in the kitchen, when in fact there had been none other than the requirement that she give herself an enema.
The part about his sisters coming home unexpectedly, was to impart a sense of urgency his mom might otherwise ignore. He intended to make his mom play by his rules and not let her put him off and spoil everything by fiddle-farting around until Mr Parker did actually turn up.
Raymond was already hard, just thinking about seeing his mom naked. He’d been thinking about it since yesterday. Would she be old and wrinkly under her clothes or would he be surprised at how young she looked? It didn’t matter. What mattered was him openly seeing it. Not spying like a pervert, but invited to watch her get naked in front of him. He’d never even seen his mom in a swimsuit before so this would be epic.
“But why in the nude, sweetheart?” Was all Jessica could think to ask even as she popped the first button and began reluctantly working on the second.
“I would think the better question would be why do you need an enema at all? One of the kids at school once said that cleaning your butt out is usually so you don’t get poop on something much bigger than this nozzle when it goes in later. I didn’t understand then. A butt is an exit only. Want to explain that to me now, mom?” Raymond raised an eyebrow at his mom, causing her to blush harder.
This was the test he’d decided on. Would his mom explain that a colon cleanse was simply a healthy thing or would she be too embarrassed to talk about it with him? He hoped for the second but was prepared for the first.
Raymond purposefully pretended ignorance so his mom would only consider him slightly curious, like any other teen his age while giving her an opportunity to sidestep an embarrassing subject like she usually did. He knew she thought of him as a kid and now wasn’t the time to disabuse her of that notion.
Of course Jessica couldn’t answer her son without telling him her Master was most likely going to soon demand the use of her most sacred hole. Jim had already told her that. It was actually years past due and although she was dreading it, she also knew she was ready to give it up to him. It was the next logical step in her submission to the Master she loved as much as Jim. As much as Jim loved Mistress Anne.
Jim understood that he’d never get to use that hole himself and they’d long ago, right at the beginning, discussed her removing anal sex from her no-go list and offering it to Master Dale. Jessica simply wasn’t ready back then.
Jim had solved their dilemma by assuring her that Master Dale might just demand it whenever he was ready, list or no list, and it wasn’t something for them to stress themselves about.
That was so Jim. Loyal to the bitter end. Or at least to Jessica’s rear end. He wasn’t even jealous of Master Dale possibly wanting something she would never allow Jim.
Now, she rationalized, Mistress Anne had recently pegged Jim and he’d admitted enjoying it. If her sweet heterosexual husband could live with having his back door opened, she could too.
“It’s just so embarrassing, is all, sweetie,” Jessica admitted to her son, her mind returning to the present as she worked on the fourth button.
Her bra was now in full view and Raymond was impressed by the size of her tits. She always dressed so conservatively, even around the house, that he’d never guessed they were that big.
“Well hurry up then!” Raymond replied, clapping his hands, not having to fake his impatience.
His mom’s stomach was now bare and she was futzing with her belted skirt, clearly reluctant to fully remove any piece of clothing.
“Hand me your blouse first, mom,” he said, holding out his hand like he was doing her a favor by giving her direction.
Jessica made a decision in the back of her mind, accepting that she should just do as she was told and not think about it. She shrugged the blouse off her shoulders before realizing she hadn’t undone the wrist buttons and then she had to slip it back on. The alternative would have been to awkwardly undo them.
She didn’t like that Raymond was rushing her with something so embarrassing yet she was relieved that he seemed oblivious to how uncomfortable the whole thing was for her. How uncomfortable it should have been for them both.
Jessica reminded herself that Raymond was just helping Jim out and she should be relieved that her son didn’t find it weird that she would be doing this in their kitchen. She didn’t want to contemplate the why of it.
The big things that bothered her were that Jim hadn’t said anything about Raymond helping, her being naked or about her doing it in the kitchen. How could Jim have missed telling her those critical details? He had to have been instructed not to, was all she could conclude.
Sometimes Master Dale was just deliciously evil. Still, she could hardly imagine doing this in her own kitchen without some sort of assistance. Master Dale was not just evil. No, he was an evil genius! Her job had to be to pretend taking an enema was no more personal and private than washing dishes no matter what she felt inside.
But Raymond had brought up another good point. She couldn’t delay any longer. Her daughters really could come home unexpectedly from their sleepover.
Jessica briefly wondered why she couldn’t at least get undressed in private but was too afraid to ask in case the question would make her son laugh at her.
He’d be seeing her naked in a minute anyway. What difference did it make if she undressed in private or in front of him?
From Raymond’s perspective, he could hardly believe his eyes. His own mother was, piece by piece, baring her body to his lustful gaze. The cardigan she’d removed when Raymond had told her they’d better get started had not meant anything to her, but now she was discarding skin coverings, warmed by her very flesh. There could be no more pleasing sight, he decided, than seeing a woman strip. That it was his own mom following his orders, just made it sweeter!
With downcast eyes, Jessica once again shrugged out of her blouse. She couldn’t look her son in the eye as she passed it to him and took a deep breath before once more attacking her belt with trembling fingers, missing her son lifting the blouse to his cheek to feel its warmth before inhaling her fragrance.
She was all thumbs undoing the belt, then the button, before drawing down the zipper and allowing the skirt to slide down her legs, exposing the fact that the long skirt hid stockings held up by a suspender belt.
With practiced precision despite her state of mind she stepped out of her skirt, lifted it and held it out to her son without so much as a glance at him. She just knew he was holding out his hand for it as he had for her her blouse and she was right. He accepted it without a word as if taking her clothing items off her was his right.
She was both mortified and oddly thrilled when she realized the snugness around her waist was not her panties but only the garter belt. If he was looking, her own son was suddenly seeing her bottomless for the first time ever.
Jessica wished she could be as detached as Raymond. There was no way he considered helping with an enema to be a sexual thing, but to her it suddenly was. He was probably disgusted by the idea of his mom having to evacuate her bowels nor had any idea why it was necessary.
Unbeknownst to her, Raymond was indeed looking. With laser intensity. His eyes were eating up every detail of her from her barely rounded tummy that no amount of exercise had fully removed to the way the straps of her garter belt pressed into her upper thighs, to the way her clit hood protruded slightly from between her labia. His mom seemed totally perfect to him and she shaved! It was like he was witnessing a half naked, fully grown little girl!
Jessica was trying not to live in the moment at that moment. She thought instead of Master Dale. How he had called this morning and had forbidden her from wearing panties today before reminding her that she was getting an enema this evening. She hadn’t in her wildest fantasies ever imagined it would be anyone other than Jim, Master Dale or possibly Mistress Anne supervising her, though.
That it would actually be Raymond, her own flesh and blood, who she’d thought was staying with friends tonight, was as crazy of an idea as if her school principal himself was doing it yet here she was, standing in a bra, stockings and low heels in front of Raymond, unable to look at him and just as aroused as if her own master was inspecting her.
“No panties, mom?” Raymond couldn’t resist commenting. “I half expected to see you wearing two pairs.”
Raymond’s calm, measured observation about the absence of such an intimate lingerie item was maddenly erotic to Jessica and she even understood why he thought she might have been wearing two pairs. She had been dressing extra conservatively since before Jim and her had started discussing their fantasies of S&M situations.
They’d made an early rule that they would never encourage others to test their marriage and that day, Jessica had gone out and purchased clothing her grandmother would be comfortable wearing. Once she herself was comfortable with the dowdy look, it had just stuck. Now, the only racy clothes in her closet had been gifts from the neighbors.
“This is so embarrassing, honey,” she admitted with her hand covering, yet certainly not touching, her shaved mound, before asking how he wanted her.
“How? Naked, for starters, mom. What part of that didn’t you understand?” Raymond asked in that same forcefully, impatient, condescending way that usually caused her juices to flow when Master Dale said something like that to her.
God I hope I’m not leaking in front of my son, she silently prayed doing everything she could to not imagine her juices coating her thighs lest she manifest.
Jessica didn’t want to think about it. She didn’t want to flex her pelvic muscles to determine the state of her pussy. She wanted solely to get this harrowing experience over as quickly as possible and asking Raymond how he wanted her was the hardest thing she’d ever done.
Then hearing him say she wasn’t even undressed enough was sweet mortification.
Bending over naked with her hands on the back of her head while Master Dale was whipping her buttocks, Jim simultaneously forcing his cock down her throat and Mistress Anne critiquing her oral technique had been easier than this!
Now she could feel herself trembling, her whole body quivering with shame as she lifted her hands, reaching behind herself to unclasp her plain white, reinforced bra while wondering if her son was staring at her secrets revealed or if the sight of her near nudity was just as embarrassing for him.
She knew what it was like to have to order Jim to do something on instructions from Mistress Anne. Things so shameful that had she a choice, she would never in a lifetime have considered asking her husband to do them.
Yet she’d had to loudly demand them of him so that they could both hear her voice and so that the microphone on the video recorder could catch every breathless request. She remembered the first time she’d ever eaten pussy was while her and Jim had serviced the neighbors. It was one of her most precious memories.
While Raymond’s voice held no uncertainty, no hesitation when he demanded her compliance, Jessica knew in her heart her son had to be quaking in his boots at the audacity of Jim’s request.
She could never have done what Jim had been made to, asking their son to administer an enema. She was more than a little surprised he’d been able to do it at all. Jessica would have lost money betting against her husband if she was still a betting woman. She was glad Master Dale had broken her of that nasty addiction.
Still, she couldn’t conceive of the idea of being tasked with supervising her own mother’s enema but such a cruel and exhilarating challenge was exactly what Master Dale was so very good at and why Jim and her were still their neighbors’ living toys after more than 3 years of serving the pair.
The bra came free, the cups loosening immediately. Her son would see her breasts, would see the tattoo on the underslope of her left one that proclaimed she was free use. God she hoped that he was focused on the ceiling, the floor, the wall, anywhere but on her.
For the millionth time she cursed the tattoo’s existence while knowing that her distended nipples were a direct result of her thinking of it. Please don’t let Raymond notice how hard they are, she prayed.
She wanted to peek. At her son, to see where he was looking. At her nipples, to confirm they were as hard as they felt. To the nozzle Raymond held, to see if he had lubricated it.
Instead, she kept her eyes closed and her head tilted forward, wishing that her hair wasn’t still in its bun so it could be hiding her shame by draping across her face right now.
Raymond watched the bra come loose and remain lightly in place, held there by the sheer size of her titties. There was not a girl in school with titties that big, not even his sister Claire whose boobs he’d once caught a glimpse of.
“Give it to me, mom,” Raymond ordered, again holding out his hand.
Jessica shivered at the sound of her son’s voice telling her to pass him her last bastion of modesty yet she did as she was told, ever Master Dale’s and Mistress Anne’s good little slut.
Covering her now naked chest with her arms was all she had left to protect what remained of her modesty.
“Damn you’re hot, mom,” Raymond gushed, unable to help himself.
Jessica noted the wonder in her son’s voice, as if what he wasn’t saying was that he’d always thought she would be a hag without her clothes on. His comment only made her more embarrassed, not more comfortable nude in front of him.
Staring at the way her boobs squished themselves under her forearms was as good as seeing that glimpse of her surprisingly long nipples.
That Jessica was hot was true, too, without a doubt. Standing a foot shorter than him at four foot eleven inches tall, Jessica’s body was a living wet dream far more impressive than her face.
While pretty enough, her eyes were just a hair too close together, her nose a little too large. Her best facial feature, he decided, were her lips. Bold, plump and perfectly formed. Beautiful even though she never wore lipstick.
Raymond returned to his study of his mom’s body. Jessica’s bust and hips were far larger than her waist and her arms and legs were toned and well defined. Raymond was immediately aware that she might well have been able to take him in a fight, as unlikely as having one would be. She was clearly in great health.
In clothes, Jessica was an energetic powerhouse that her kids at school never considered trifling with. Her clothing was however her armor. Without it, she felt meek, a little insecure and totally submissive. And now she knew her son was looking at her, bared to her very soul. She bit her lip and said nothing.
Raymond took a mental breath to steel himself. He figured the time was right to crank it up a notch and test himself. If he’d read the situation correctly, his mom wouldn’t bolt out of the room in righteous indignation. He’d know shortly if his instincts matched his desire.
“The proper response would be, thank you Raymond, or I’m glad you’re pleased, Sir,” Raymond prompted his mother.
“I can’t say that!” Jessica’s head shot up and she looked directly into her son’s eyes, unable to help herself.
“Of course you can!” Raymond smiled, doubling down, meeting and holding her eyes until she lowered her gaze again. “It’s part of being polite,” he told her. “You’re a polite girl, aren’t you, mom?”
“Yes, Sir ... I mean Raymond. “Do you know how embarrassing this is, though?”
Yes! I’ve got her! Raymond congratulated himself, carefully to not start jumping around and punching the air in triumph.
She’d called him Sir although it didn’t really count because she’d corrected herself this time. She had still done it though. He decided he could celebrate properly once she used the title with intent.
“It’s skin, mom. Everybody has it,” he shrugged. “I’m going to be honest with you. Yours is particularly lovely even if I do have to say so myself. If you think that me seeing you like this embarrassing, what would you call what comes next? Bending over and holding your cheeks apart so I can put this nozzle up your butt isn’t going to bother you a little? Just think of me as someone in authority if that helps,” Raymond suggested, picking up the nozzle again and swishing it like a cane as if to show her what could happen if she disobeyed him.
“I ... You...” Jessica couldn’t think of a response.
“Dad’s going to be so proud of you mom, taking your enema like a good girl. Do you think he’s going to appreciate how much effort you’re going to?”
Talking about his dad was a calculated risk. Inferring he might know more about the situation than he was saying, a bigger one. Raymond knew that no risk meant no reward. He’d already taken risks and the naked reward was standing, trembling in front of him. He was ready to take this train all the way to the last stop!
Raymond was tempted to talk about his mom taking his dad’s cock in her butt, then changed his mind. He knew that it’d be Mr. Parker who would be parking his dick inside his mom’s cheating asshole and he wasn’t about to lay all his cards on the table, yet.
The thought of Mr Parker plundering his mom’s butt still bothered him, though. How come the neighbor got to fuck his mom’s asshole while he, the good son, didn’t? At least, Raymond reminded himself, he would be fucking it with the enema nozzle first before Mr. Parker knew what was going on.
Let mom explain to the neighbor why she let her son stick something up her ass before Mr Parker did. That brought a smile to Raymond’s face.
Mr Parker should never have told his dad that he was going to fuck Jessica’s tightest hole for the first time. There are just some things one shouldn’t share with one’s married neighbor especially when the subject was that married neighbor’s wife’s butt hole.
“Please just get it done, Raymond,” Jessica whined pitifully.
“I’m holding the nozzle, mom. I think I deserve to be called Sir, don’t you?” Raymond asked, putting a little edge into his voice to let his mother know she was in no position to make demands no matter how politely she phrased them.
“You’re my son, Raymond not my Mas ... not my father!” Jessica had barely caught herself.
“You don’t seem to be fully grasping the situation, mom. You know you’re a good girl. You undressed for me. You’re getting ready to have a nozzle jammed up your butt, yet you want to discuss semantics? Are you going to remain a good girl for dad?” He asked, closing the distance between them.
Jessica heard him drawing closer until he was well within her bubble but fully dressed while all she wore was a pair of stockings and a tattoo that proclaimed her free use.
She was Master Dale’s good slut above all else, but her son had hit a nerve by asking if she was Jim’s good girl. Jim often told her how proud of her he was following a session either with the neighbors or someone Master Dale had ordered her to satisfy and it sounded very much like being Jim’s good girl and she did want to be good.
Yet she couldn’t let him notice the tattoo. She also couldn’t stop feeling like he was exerting power over her in a way that was scary, exciting and inescapable. Her own son. Emulating Master Dale. All while doing his father a favor.
“Sorry, you’re right ... Sir,” Jessica managed to reply. “I am a good girl,” she admitted, feeling as if a weight was being lifted when she vocalized it.
Raymond almost creamed himself upon hearing his mom call him, Sir. All by herself. His naked mom. Standing close enough that he didn’t even need to reach out to touch her at this point. If he lifted his hand, he could place his palm on the upper swell of her breast. He even for a moment considered doing just that but something stopped him.
He didn’t want to break the spell by pushing too hard, too fast. He’d managed to get her naked. He’d exceeded his goal by getting her to call him sir. His new goal was now to have her invite his touch, not to steal it from her. She was, after all, his mom, not a female he cared nothing about.
“I need you to get the big canning pot out of the bottom cupboard,” he spoke quietly near his mother’s ear, drawing in the scent of fear, arousal and his mom’s peach bodywash.
“Sir?” Jessica asked with a single quizzical word.
“The enema water has to go somewhere, mom,” Raymond assured her. “Unless you would prefer to evacuate in the back yard?”
“Oh, God, Raymond. Why can’t I use the toilet?” She asked just as softly, as if someone else might hear.
“We’re in the kitchen. There’s no toilet here. I don’t know that you could make it upstairs in time,” he replied.
“The guest bathroom,” Jessica tried.
“Tisk, tisk, mom. Don’t think. Just do. There’s a good girl.”
Another milestone. She didn’t half-heartedly fight him over his words but instead accepted them.
Jessica couldn’t decide if her son’s cold, hypnotic voice was calming her or scaring her more. Surely he shouldn’t be talking to her like she was the child and he was the parent?
He’s fulfilling an obligation just the way Jim did when he asked Raymond for his help, Jessica rationalized. Maybe Jim had been told the guest bathroom was off limits the way their master bath sometimes was?
“I ... its ... could you not look while I get it?” Jessica pleaded with her son, already feeling like her face was on fire.
“Why? It’s a little late for modesty now, mom. And when you evacuate it’s going to be loud, smelly and THEN you’ll have some reason for embarrassment. I’ll probably be embarrassed for you too. Maybe. Well probably not. It is after all just a normal bodily function. But for now, enjoy the fact that I can’t stop looking at my good girl.”
Raymond had read that repeating words and phrases over and over was a psychological ploy to normalize the unusual. He could already tell it was working on his mom. He could see it when her mouth twitched like she wanted to smile at being called a good girl.
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