A Proper Young Man's Guide to Anal Etiquette Ch. 05
A Proper Young Man's Guide to Anal Etiquette - Chapter 5
By: Lord Odie
The Obligatory Disclaimer
The following is a work of pure sexual fiction 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 meant as a compliment. Furthermore, all fictional characters in the following fantasy are consenting adults over the age of 18. They are also BDSM professionals and good at what they do. So please, don't try anything that you're about to read at home, if such things were even physically possible. If you still insist on trying things at home, please send all pictures and feedback to me about the experience. If I can't stop you, I can at least make sure you're doing it right. Consider yourself disclaimed.
5. Training Time with Matt's Aunts
Samantha groaned deeply as her nephew worked his second elbow past her resistant sphincter to join its twin. "Fuck, baby!" she cried out as her ruined asshole gave up its pointless resistance and succumbed to the inevitable.
Samantha was his father's stepsister. So, while there was no blood relation, she was technically still family. Matt had been living with her and her wife Mina ever since he'd come of age. Similar arrangements were quit common for young men so they could learn their roles in society in a 'safe' atmosphere before striking out into the world on their own.
"Now just like you've practiced, honey," Matt's more dominant aunt, Mina, said encouragingly. "A woman's anal ring is very sensitive, so you don't want to be gentle with it. Despite her cries, a woman's asshole can take a shocking amount of punishment and be perfectly fine... Eventually."
"Yes, Aunt Mina," Matt said with an annoyed eyeroll as he worked his thick, muscular arms deeper into Samantha's cavernous nether hole while his aunt struggled with their well above average girth. He was currently nude with his mostly erect, thick 11" cock dangling between his burly legs.
Mina only smiled. "Testy..." she cooed. Mina was of Filipino and Japanese descent and stood at barely 5' 1" tall. At 51-years-old, her trim frame and small ass made her mocha colored, 30C-cup breasts look larger than they actually were. Thanks to modern anti-aging therapies, Mina looked like a woman in her early 30's would have looked a century ago. As usual for their family training sessions, she wore her long black hair in two pig tails on the sides of her head. She only wore a black garter blet with matching stockings, dark red high heels, and a pair of impressively strong nipple clamps crushing her always rock-hard dark brown nipples. She stood beside her nephew observing the deep fisting. Her right fist was buried inside Samantha's gooey cunt and her left hand was between her nephew's cheeks. Three fingers were already past his sphincter, and she was planning on adding a fourth in a minute once he relaxed a little more. "So, you think you're ready to train a woman on your own?"
"Yeah, Aunt Mina. I am!" Matt confirmed with an extra hard push that buried his left bicep a few inches up his blonde aunt's asshole. He really was almost at his breaking point with pent up frustration.
"Slow down, baby! Give Auntie Samantha a chance to stretch," the reclining woman groaned. Samantha was a 49-year-old 5' 7" blonde. She was quite attractive with her bob of hair, 36E-cup breasts and curvy thighs. She wore attire similar to her wife, but with white lingerie and significantly stronger nipple clamps. She was hanging in a sex swing in the family's living room at roughly Matt's chest height. The swing had metal bars that spread her legs directly out to a comfortable 170-degrees to either side. Her arms were in a strappado and pulled directly towards to ground. The swing was powered by a winch tastefully hidden in the ceiling.
Samantha wasn't actually a lesbian and only agreed to marry Mina when she'd decided her luck had run out with the men she'd been trying to entice. Mina knew this but didn't really care though. At the time, she was primarily looking for a set of willing fuck holes to hollow out and someone hot to have on her elbow at company parties. Samantha was more than adequate at fulfilling both jobs. But after all these years, the two were basically inseparable.
"Mina, get the cock gag for Auntie Samantha," Matt said without being prompted. "She should know better to complain about something she so desperately needs!" he added working his right bicep in further to catch up to his left.
Mina took a half step back. She was about ready to scold her nephew for addressing her like that, but instead chose to follow his unexpected order. She slipped her fist out of Samantha and her fingers out of Matt to retrieve the gag.
With a slightly panicked look on her face, Samantha tried to plead, "I'll be good! You don't need to gag me, baby! Please, ba..." was all she got out before the long cock gag sank down her throat and silenced her. She knew as well as anyone that a gagged woman without the ability to protest was nothing but a set of holes to be filled. Without being asked, Mina inflated the gag's base until her wife's cheeks bulged out and her jaws looked like they would dislocate.
"That's better," Matt said half to himself as he started to slide his biceps back and forth in his aunt's guts, working them deeper as he went. Samantha stopped trying to protest and just hung in the swing and groaned as much as she could past the cock gag filling her throat as her nephew brutalized her asshole.
"I'm so proud of you!" Mina said to Matt as she returned to her previous position. She reached between his cheeks sank three fingers into his moist butthole and started working in a fourth finger. Her hands were small, and her nephew's sphincter was well accustomed to being wrapped around her fingers as she jerked him off while tucking him into bed every night. No young man should go to bed without his balls drained, after all!
"Just three fingers will be enough for tonight, Aunt Mina," Matt said without looking at his diminutive aunt. Mina stopped in shock for the second time tonight. Her fourth finger was only half in her nephew's asshole. She smiled to herself and slipped it out. "If that's what you want... Sir," she replied instinctively.
Now it was Matt's turn to look at his smaller, more dominant aunt. She met his stare for only a second before lowering her gaze. Matt felt his cock twitch. This felt suddenly right!
"Is there anything else I can do to help... Sir?" she asked suddenly more meekly.
Matt only paused for a few heartbeats. He could sense the change in the home's power dynamics. He could feel it as if it were a tangible thing. Matt's smile grew from young and mischievous to mature and sinister within seconds. Without even seeing it, Mina could sense the change in her nephew's demeanor as well.
"Get the other cock gag and help me get Samantha down. There's another asshole that needs tending too in this house."
Mina started to protest. She'd never let her nephew truly train her asshole the way that she'd taught him to train her wife's loose ass ring. Sure, maybe a deep colonic massage with just one of his thick fists and arms, but never both of them. Never! She opened her mouth to say sternly, "Now slow down there, mister!" but instead surprised herself with, "Yes, Sir." Seconds later, with the 1.75" thick, 15" long cock gag lodged down her throat as she pumped the bulbous end up until it started to hurt her jaws, she still couldn't truly believe what was happening.
* * *
An hour or so later, Mina still hung in the sex swing with her legs spread wide and her arms pulled to the floor beneath her. At one end, Samantha held onto her wife's spread legs and drove the 5.75" wide light-grade torture dildo she had strapped to her waist up her wife's suddenly more spacious rectum in long, powerful thrusts. As far as she knew, Mina had never actually used a dildo this large on her asshole before, and certainly not a torture dildo model! Mina's overstretched sphincter clung to every nub and nob of the torture dildo as Samantha sawed it in and out of her body with a vengeance. The shape of the large dildo was easily discernable through Mina's toned belly as it made its way from her hips to underneath her ribcage.
At the other end, Matt drove his thick 11" cock down his aunt's throat as his large hands wrapped around its outside. He wasn't squeezing too hard, just hard enough to let Mina know he could. His aunt's delicate throat looked odd with the bulk of his cock stretching it well past her clavicle. But her comfort was not his concern as his cum boiled in his balls.
With a final, powerful thrust, Matt bottomed out in his aunt's throat, groaned in satisfaction, and emptied his balls down Mina's gullet at last. Rope after rope of cum blew straight into his aunt's struggling esophagus. Being a pure lesbian, his older aunt truly sucked at giving head. She'd never much cared to learn the skill. That was about to change! After all, Samantha was excellent at it and should make a fine teacher. With a shuddering gasp, Matt shook himself to help him recover.
He felt Mina gagging on his softening cock and realized it had been some time since he'd allowed his aunt breath. He quickly pulled out and Mina gasped a huge breath of air. Her mouth remained wide open as it was held open with a bit-gag wedged between her back teeth. Matt gave the woman several breaths to replenish her oxygen before offering his half-erect cock to her again. Despite being a novice cock sucker, Mina's tongue reached out to lick the tip of his dick to savor the remnants of his orgasm. Samantha was still pummeling the depths of Mina's colon with the large torture dildo, so Mina began letting out satisfied groans once she had her breath back. She was obviously enjoying the treatment.
With his dick at half mast, Matt drove it back into his aunt's throat again without warning, eliciting a pitiful gagging noise from the bound woman. "Get the last few thrusts in, Samantha," Matt said without looking up as he watched Mina struggle on his cock again. "I want you in the swing for the next hour or so. I imagine Mina is going to want some revenge!"
Samantha swallowed hard and missed a beat before resuming. "Yes, Sir," she replied obediently. She bit her lower lip before offering a suggestion. "Sir, my asshole is used to rougher treatment than Mina's is. Should I bring out my heavy-grade torture dildo set?" she asked. "Mina usually only uses them on me on Saturday night so that I have all of Sunday to recover," she added, knowing full well that it was Thursday evening and she had to work in the morning.
Matt thought for a few seconds as he tried to relax his muscles. He closed his eyes and groaned as he felt several hours of piss start to drain into Mina's stomach. His aunt tensed in the swing but could do nothing to fight back. He knew she'd never allowed anyone to urinate down her throat other than her own mother when she'd been younger, but she liked to do it to Samantha quite often. Well, Mina's just going to have to get used to it! Matt thought to himself with a smile. "I think that's a great idea!" he replied aloud, squeezing the last few drops of urine out. "What's your maximum dilation right now? 7.45"?"
Samantha gulped as she pulled the 5.75" wide, light-grade torture dildo out of her wife's raw and obviously sore asshole. "Yes, Sir," she replied.
"Good. Bring a few smaller ones to open you up, and the 7.50" and 7.55" wide ones so we can have a goal," he said as he began stroking his hardening cock back and forth in Mina's throat.
"Yes... Sir," Samantha said obediently before scurrying off to their bedroom to retrieve to requested toys.
Tonight has taken an unexpected turn! she exclaimed to herself silently. But a big part of her nurturing side was so proud of Matt for finally taking charge! Of course, most young men came out of their shells in their early-20's. So, Matt's timing was a little late. But better late than never!
* * *
"So, how is your personal life, Matt? Anyone special?" Mina asked as she laid sideways on his muscled chest on the couch and played with his emptied balls. Samantha was on her knees servicing his half-erect cock after he'd deposited a load into her stomach. The 7.55" wide torture dildo was locked into her rectum for the evening. Mina had already called her wife's boss, Stacey, and told her that Samantha would be out with anal fever tomorrow. Stacey had been trying not to grunt too conspicuously as they talked and mentioned that Samantha might not be the only one. Matt didn't know who his aunt's boss was with, but obviously that someone was actively doing a number on her. Mina had only laughed, reminded her wife's boss that she probably had plenty of sick time built up, and then said goodbye.
Matt just grumbled, "Not really. There's one girl I might be interested in, but we're just talking. Most of the girls I fuck are just convenient holes to fill. Not that any of them seem to mind. It seems like all the girls just want to get in my pants for a chance to put a ring on my finger. It's fun! Don't get me wrong! And I'm certainly not complaining. But I do think that I need to pay a little more attention to them rather than just pumping a few loads into them and dumping them."
"Well, girls will be girls!" Mina replied with a smirk. "They have to land a guy somehow or end up sucking pussy for the rest of their lives like your aunt down there," she said playfully.
"Hey!' Samantha exclaimed, sitting up and pulling Matt's dick out of her throat. I don't have to suck your pussy with such enthusiasm, you know!" she added before returning her attention to her nephew's cock.
"Fair point!" Mina relented. "But seriously, Matt. You could just catch yourself a hottie with a good career like your uncle Jonathan and live a plush life of working out, fucking your personal trainers, fucking your wife's secretary, and fucking your wife when you're bored," she said in all seriousness. "Just find a nice girl who can carry on a decent conversation... and with big tits, a hollow ass, and a pussy like a well-oiled vice!"
"But you're right on you needing to be more attentive!" she continued. "We've been trying to make you take charge for a couple of years now, but you've never really given a shit about anything other than your cock. Until tonight, that is. We don't know what came over you tonight, but you're finally growing up into a man who knows how to properly treat a woman! And we're so proud of you!" she said, beaming with pride. She gave his mostly empty balls a few good squeezes. This caused his spent dick to twitch a few times.
Matt just laughed. This wasn't the first time he and his aunt had had this conversation. But this was the first time he was open to what they were actually trying to tell him. "You're right, of course," he conceded. "I think it's past time that I start paying attention to the anal wellbeing of the women around me!" he concluded with honest conviction.
"Oh, really?" Mina asked, raising her eyebrows.
"Yeah. I think so," Matt replied with a smile.
Mina just laughed, and then groaned as the mass of the 5.75" wide dildo locked up her own rectum shifted uncomfortably. "Well, I'm glad you agree with me," Mina said firmly as she stood up gingerly. The mass of the dildo filling her colon was still quite visible against her skin. "It's getting late, and you have class in the morning. So why don't you find a suitable program for us on our Guten Nacht Bette and then get yourself some sleep."
Matt hadn't realized it was after midnight and he was indeed tired. "Sounds good. Why don't you email your boss and tell her you'll be out tomorrow with anal fever too, and I'll get your bed ready. I think Samantha has some old heavy-grade torture dildos in your size."
"I didn't mean..." Mina looked shocked yet again. This was going to take some getting used to. "Yes, Sir," she replied meekly.
- After learning the ropes of BDSM and anal play from his aunts and their extensive collection of toys, Matt felt ready to attempt extreme anal play on his own.
- As he carefully inserted a strap-on harness and a large anal toy, Matt recalled the advice from Chapter 5 of "A Proper Young Man's Guide to Anal Etiquette" about being gentle yet firm when exploring a woman's sensitive anal ring.
- Feeling confident with his newfound skills, Matt invited a friend over for a session, knowing he had the proper training and equipment to ensure a safe and enjoyable experience.
- When things got too intense during the session, Matt remembered the time his uncle chastised him for ignoring his needs while being too focused on pleaseing his partners, and he made sure to take breaks and prioritize his own well-being.
