A Proper Young Mans Guide To Anal Etiquette Ch 04

A Proper Young Man's Guide to Anal Etiquette - Chapter 4

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.

4. Training Time with Jessi's Mom

Making his way to Jessi's quadplex, Matt ran up the outside stairs to her deck and pressed his thumb to the back door's entry pad. A green light lit up, and an entry tone chimed. He opened the door and let himself in. The layout of Jessi's home was identical to his own. The only differences were in the paint color and furnishings. "Jessi? Do you know what time it is? If you don't login in now, we're going to have to forfeit the match!" he called out.

"Is that you, Matt?" Charlotte's voice came from the bedrooms. "We're back here training."

"Now?!?" Matt replied in annoyance as he made his way through the house.

Upon entering Jessi's bedroom, he found his best friend tied to an overstuffed chair. She was naked except for her white ankle socks and blue sneakers. Her ankles were secured to the chair's top corners with Velcro straps and her butt was pulled off the edge of the seat. Jessi's arms were in a leather reverse prayer binder behind her back. Strong clamps crushed each hard nipple. Her long brunette hair was done up in a ponytail that was half plastered to her sweaty face. The young woman's mouth was filled to the breaking point with an inflatable ball gag. Matt could see a thick punishment catheter secured in her urethra with a tube running from it to the base of her gag.

Her mother Charlotte looked nearly identical to her daughter, just a bit older. In fact, they were often confused as sisters when they were out in public. Charlotte was dressed only in white stockings, a garter belt, and a white waist cincher. As Matt approached the pair, he could see similar looking clamps crushing her own nubs. The 45-year-old single mother was sitting between her daughter's legs atop a rough looking punishment dildo that had to be nearly 6" in diameter, which was close to her maximum dilation. It was quite an impressive size for a woman with such a slight frame. She had red latex gloves on each arm that came up past her biceps. Each glove was covered in nubs and bumps. Currently, both arms were buried up her daughter's ever-expanding nether hole. Her right elbow was past her daughter's sphincter, and her left was a few inches away from Jessi's straining ring of muscle. "I thought you didn't train until 8:00 on Tuesdays?" he questioned.

"Well, normally, that's the case," Charlotte answered. "But I have to work an unexpected shift at the hospital tonight and had to push up our training before I left," she replied before turning her attention back to her daughter and instructing, "Push out, baby. Mommy's elbow is almost inside!" She spoke in a higher pitched, loving, cutesy voice. Not her normal voice that she used when she spoke to Matt.

Charlotte was an RN at Saint Dee's Hospital downtown. The pay was great, but the hours were horrible at times. Her attire made sense now. The white lingerie was part of the hospital's uniform for nurses.

Jessi groaned in objection as her mother's arm sunk even deeper inside her protesting guts.

"Well, can Jessi do this later?" Matt asked. "We need to get online and play a ranked match!"

And anal training is stupid anyway,

he added silently.

What good is a stretched-out asshole to me anyway?! It's not like I can fuck it...

Charlotte almost seemed offended. "No... No! A woman's anal wellbeing shouldn't be pushed off, Matt!" she replied.

Haven't your aunts taught you anything?

she said to herself. "Your match can wait for an hour."

"No, it can't!" Matt protested!

"Are you going to spend an hour training her yourself after your match then?" Charlotte asked with annoyance.

"Well, no," Matt admitted. "Certainly, she can go one night without being trained, can't she?" he asked, already knowing the likely answer. "Her asshole is already pretty loose."

Charlotte just ignored Matt, "Relax, baby. Just ignore the rude, thoughtless boy. Mommy knows what her baby needs. You remember how hard you came last Friday when Mommy's strong arms were inside your needy bottom for most of the night, right?" she continued in the same matronizing voice.

Jessi's eyes met Matt's briefly before the young woman returned her attention to her mother and nodded slightly. She was obviously not completely comfortable with having her mother train her nether hole in front of her male best friend.

Matt wanted to say something more in protest but knew it would be pointless.

"Well, then push out for Mommy!" Charlotte commanded. Jessi groaned as she bore down, and her mother's arm slid forward several inches, nearly inside past her second elbow. She worked them back and forth for a few seconds before adding, "One more push baby, and then both of Mommy's arms will be completely inside her baby's horny bottom. And then Mommy will make sure her precious baby girl asscums really hard! Now push!" Jessi's eyes locked with Matt's, and she groaned even louder. "There we go!" Charlotte proclaimed as both elbows finally sunk past her daughter's anus, as her daughter's eyes almost rolled into the back of her head.

Matt had never really understood everyone's obsession with stretching women's buttholes. You can't fuck a gaping, useless asshole, so what was the point? He was about to turn and leave in defeat until he heard Jessi's lusty groan. Glancing down again, her mother had pulled one of her elbows out past Jessi's over-stretched anus and was pushing it back inside. The poor girl's anus was almost white from the strain of the extreme stretching. It looked like it was about to snap, but he realized Charlotte knew better than to push her daughter that far. The battered ring of muscle grabbed and pulled at every nub and notch on Charlotte's gloved elbow, almost like there wasn't enough lubricant, despite both gloves glistening in thick anal gel.

Quickly enough, Charlotte's elbow disappeared past her daughter's straining asshole, only for her other elbow to slip out. This elicited another lusty groan from the bound young woman. "There we go, baby!" she said proudly. "Do Mommy's arms feel good up your needy bottom?" she asked. Jessi nodded her head emphatically as her mother reversed the direction and her young sphincter quickly engulfed the gloved elbow once again. Charlotte ground both of her elbows together inside Jessi's nether hole, and the young brunette almost melted with lust. Matt could see the outline of the older woman's closed fists rotate around inside the younger woman's guts underneath her toned abdomen.

"You see, Matt. A woman's back hole is very sensitive, especially just inside the anus. See how Jessi wiggles as I rub my elbows together and grind the glove's nubs into her inner flesh? This will send almost any red-blooded woman's sex drive into overdrive!" she instructed. Of course, Matt's aunts had told him the exact same thing during their multiple times a week anal wellness sessions, when he'd assisted Mina in pulverizing Samantha's insatiable backside. But he'd never really been all that into anal wellness sessions with his aunts. He wasn't really attracted to them at all in that way. That would just be weird! Sure, he really enjoyed the daily blowjobs. But blowjobs weren't sex, after all. They were just something women did to make men happy. Seeing Charlotte train her daughter and his best friend like this was almost eye opening! He really didn't see Jessi as a potential romantic partner, but there was certainly more attraction there than with his aunts!

And there was no denying that watching Charlotte work both of her arms around inside her daughter's nether hole in front of him was having a very immediate reaction in his pants! "Yes..." Matt managed to stammer. "I see..."

"Good," Charlotte replied.

There might be hope for you yet, Matthew Downey!

she said silently as she began to increase the speed at which she was thrusting her elbows in and out of her daughter's still tight ass. Turning her attention back to her daughter and changing her voice again, "Now just relax, baby. Mommy will make your bottom feel good. Can you give Mommy and Matt a good hard asscum? Mommy knows her daughter is a juicy squirter, just like her Mommy is. Don't you want to taste you own cunt juices? Mommy has a nice big catheter locked into your naughty little pisshole and it's plugged into your gag. Can you asscum really hard for Mommy and Matt and fill your slutty little mouth with your hot squirt? Can you do that for Mommy, baby?" Charlotte continued to goad her daughter to orgasm as her arms increased the speed and ferocity of their assault on Jessi's defenseless asshole. Changing her tone to address Matt, "Most young women react very positively to a very matronizing voice. My own mother still uses it on me from time to time, and I just melt into a submissive slut every time!" she explained.

Finally, after several minutes of pounding and more sexy motherly coaxing, Jessi went rigid and came harder than Matt had ever seen her orgasm in the many, many times they'd fucked. Charlotte's arms were almost punching into Jessi bowels by that point. Both women's smallish C-cups and clamped nipples bounced and jiggled as Charlotte worked. The older woman's arms were punching so deep into her daughter that her fists almost reached the young woman's ribcage. After nearly a minute of cumming hard, Jessi finally collapsed into her bounds and tried to catch her breath. Charlotte slowed her pace to allow her daughter to recover slightly and gulped in some air to recover herself.

"That was an okay asscum, baby. But Mommy has seen you asscum a lot harder than that! Are you too distracted by Matt to cum really hard?" she asked. Jessi only nodded in affirmation weakly. "You really shouldn't be!" the older woman scolded. "Matt's old enough now. If he were a proper young man, he should be offering to take a personal hand in your anal wellbeing," she said with a sidelong glance at the muscular young man.

The glance was not lost on Matt. He flushed slightly at the thought but said nothing. The idea had never really occurred to him. He found the anal wellness sessions with his aunts more bothersome than anything else. His balls weren't actively being drained, so his interest was minimal. He'd rather be playing video games with Jessi or his other best friend Kyle or emptying his balls into one of the willing and eager young neighborhood women.

Just then, Charlotte's phone rang. Glancing down at it, she saw that the incoming call was from the 35th floor nurse's station at Saint Dee's Hospital. She glanced down at her arms, still buried up her daughter's backside. "Shit!" she said. "Accept call. Voice only." She replied.

Her phone replied, "Accepting call. Connecting to bedroom television for audio visual feed."

"No, god damn it!" Charlotte half screamed. "Stupid phone!" she grumbled as the image of an attractive busty Hispanic woman in her mid-30's came up on the bedroom's 120" high-definition screen. She wore a standard nurse's uniform which consisted of a too-tight white short-sleeved latex minidress that came only partway down her shapely thighs. The neckline plunged down far and wide enough that the woman's thin white lacey bra was half uncovered underneath. In fact, her obviously erect nipples were almost visible at the edges of the bra and the lingerie was nowhere near covered by the dress itself. Below her bra and barely visible was the top of a white waist cincher. She wore white stockings, shiny white heels, and a white hat with a red cross on it. Pretty standard stuff.

"Good evening, Carmen. Sorry, but my phone is being stupid!" Charlotte tried to explain with a shrug of her shoulders.

The video on the other end of the call was obviously coming from a camera mounted relatively high on a wall. Behind the nurse were four empty hospital beds in what was obviously one of the hospital's many rooms. Carmen smiled at the unexpected sight of her coworker with her arms buried up her daughter's asshole and a humorously dumbfound looking young man standing in Charlotte's bedroom together. There had to be a funny story here, but she'd have to ask later. She'd also have to have Charlotte introduce her to the muscular 20-somehting man when she was over for drinks and oral sex next weekend. She would enjoy ruining any innocence the cute young man might have left!

"Sorry to call you again, Charlotte. Good evening, Jessi," Carmen said after a few seconds of relishing some alone time with the unknown young man. "But Dr. Glassley is being her normal, bitchy self. She wants all the on-call nurses in here as fast as possible. She's convinced that there was E. coli in our lunch a few hours ago and wants the entire 35th through 37th floors' nursing shift's bowels power-flushed ASAP!" explained the sexy Latina as two other nurses came into the feed from outside the room. The taller one was a fair-skinned redhead and the shorter one who looked to be of Chinese or Japanese descent with long silky jet-black hair that fell down her back well past her ass. The former was even bustier than Carmen was while the latter looked to have a slightly smaller sized chest. Neither could compete with Carmen in the curvy hips department though. Both nurses smiled at Charlotte's onscreen image and waved.

"That's just dumb..." Charlotte answered, without removing her arms from Jessi's nether hole. "I'm a little busy right now, but I should be there in an hour and a half or so," she added.

Onscreen, the redheaded nurse had unzipped Carmen's dress and helped her out of it while the other nurse was gathering some supplies from a cupboard behind one of the empty beds onto a metal cart.

"Well, Jessi's anal wellbeing is important, after all," Carmen said in resignation as she unhooked her bra and let it slide to the floor while the redhead loosened and removed her waist cincher. With a surprising quickness, she was standing in the middle of the room in just white stockings, a garter belt, heels and her little hat. The bulge that was now visible against her bare stomach spoke to the size of the latex object lodged in her bottom. Matt could just barely see the base of the white latex dildo underneath her bald mons pubis. He could also see the base of a large medical catheter protruding from her urethra, which had a pair of rubber tubes dangling from it. She placed her arms behind her back as the black-haired nurse began working a white leather single sleeve armbinder in place, and the redhead began binding the bases of her 36E breasts with self-adhering medical latex from a roll. They worked in practiced unison to quickly bind their coworker before fetching more supplies from the cart.

"You know, sometimes I think I made the wrong career choice," the Hispanic nurse admitted.

"Why would you say that?" the Oriental nurse asked as she pulled and twisted Carmen's nipples to harden them up for the pair of evil looking stainless steel clamps she'd retrieved from the cart.

"I swear I spend almost as much time being a patient here as I do working here!" replied the mocha-skinned nurse in annoyance.

The busty redhead nurse was attaching a large liquid-filled plunger to one of the rubber tubes exiting Carmen's catheter. The clear cylinder looked like it contained almost a gallon of cloudy blue liquid. "But we're still getting paid, so I don't see what the problem is," she commented as she began to depress the plunger. "Sorry for the temperature. We were running low on healing stimulants and had to get more from the freezer downstairs," she explained as almost half the liquid disappeared into the nurse's bladder in a matter of seconds.

"Oh, holy shit!" Carmen cried out as the freezing fluid quickly filled her bladder. Matt could see her nipples harden instantly on the screen's high-definition display and her teeth started to chatter. And then she let out an uncomfortable groan as her bladder reached its nominal capacity. The redheaded nurse continued pushing the plunger, but slower than before.

"Thanks! That got 'em really hard!" the back-haired nurse said happily as she started wrenching the clamps down on Carmen's now painfully erect nubs.

"Just get in here as soon as you can," the Hispanic nurse said as her coworkers moved her over to a waiting empty bed.

"Will do," Charlotte replied while she watched. But the nurses were busy with their tasks and didn't hear. "Matt, can you please end the call?" she asked, nodding to her phone.

"Of course, Mom," Matt replied, picking up the phone. But instead, he quickly disabled the audio and video pickups and discretely transferred the call to his own phone before placing Charlotte's phone back down.

"Well, I was going to offer to let you stay and watch, but I need to expedite Jessi's training. I'm sorry about your match, but I'll make sure Jessi comes over as soon as she's not tied up," Charlotte said apologetically.

"Thanks," Matt replied and quickly backed out of the room. He kind of wanted to watch, but he really wanted to see what was going on with Carmen. Matt had always had a thing for older Hispanic women.

As he walked down the hallway towards the back door, he heard Charlotte say in her comically motherly vice, "Now then, let's get a few really good asscums worked out of your horny butthole before Mommy has to go into work. I was hoping that you could help Mommy with her anal wellbeing before I left, but it looks like Mommy's needs are going to have to wait until her first breaktime."

Once Matt had closed the deck door behind him, he pulled out his phone and brought up the call. He popped out the phone's earbud and slipped it in so he could listen in. Onscreen, Carmen had been bound face up onto the bed, which was reclined at about a 45-degree angle. The beds themselves looked to be fairly short, maybe only 4' long. Both of her legs were attached to a metal bar at the top and slightly behind the bed's mattress. This pulled her legs behind her shoulders and spread them so wide that it had to hurt her hips. Matt could see her bound arms pulled straight downwards from her body and away from her torso in what had to be a painful position. While his phone had been in his pocket, four large devices had been brought in and locked onto the front of each of the four beds. They looked like clear glass cylinders maybe 12" in diameter and 3' tall. The cylinders were angled slightly backwards and pointed towards the beds. Each was topped with a rubber and steel double grommet of some sort which were 6" or 7" in diameter. The double grommets had a total of three raised rings, each separated by maybe 2". A slightly smaller ring in the middle and two wider rings at the top and bottom. Each cylinder also had a thick coiled tube of some kind extending from inside the cylinder's base and extending out the top. The tubes looked to be maybe longer than any woman could take if fully rolled out, and roughly 2.5" thick. The cylinders were filled with a light blue liquid.