A Proper Young Man’s Guide to Anal Etiquette – Chapter 2
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.
2. Just A Normal Tuesday at Home
Matt tried his best to keep studying. He really did! But it was hard to concentrate with one of his best friends Jessi Stevenson having phone sex with her mother Charlotte just feet away from him.
“Oh, shit! Would you really do that to your own daughter?” moaned Jessi into her phone. The 24-year-old brunette was lying back on Matt’s bed facing him. She was less than three months younger than Matt, making her the youngest of the three friends. Her black volleyball short shorts were bunched up around her ankles and her white and blue uniform top and black sports bra were pushed up on her chest to expose her well-shaped tits. The athletic little number was only 5′ 4″ tall, but she’d played volleyball since middle school and had a toned muscular bubble shaped ass that you would expect a woman to have after a decade of the sport. Her 30C breasts were on the small side but they were ridiculously perky and looked perfectly in-place on her compact frame. Her long brunette hair was done up in a ponytail that was half wrapped around her neck. Matt has always thought his friend had the cutest most innocent-looking fuckable girl-next-door face he’d ever seen.
“Oh, fuck! That would hurt so bad and feel so good at the same time! Would you want me to do that to you after you’ve finished me off?” she continued. “God, you’re such a slut, Mommy!” she said with an excited giggle. Jessi had an earpiece in, so Matt couldn’t hear what her mother Charlotte was saying, but he tried to imagine. Jessi was lying face up on his bed with her spread legs towards Matt. The young brunette’s left hand was holding the base of a 4.15″ thick lightly veined dilation dildo – which she’d secured in her ass after practice – down on the bed while her hips rose and fell, sliding the last 12″ or so of its length through her well-trained sphincter. He could easily see its outline against her trim midriff as its bulk snaked its way through her colon. Her right hand was alternating between viciously rubbing her swollen clit and effortlessly sliding her closed fist into her slightly gaping, dripping cunt up to the wrist, and back out again. A small pool of pussy juice was collecting in front of the dildo as the slick fluid dripped steadily out of her front hole. Her rock-hard nipples moved delightfully with her smallish breasts as her body shifted. From Matt’s position across the room, he had an excellent view of the girl’s swollen and cock-free pussy. All he really wanted to do was walk over there and shove his cock into the brunette and fill her cunt with his cum.
Jessi and Matt – along with their other friend Kyle – had been best friends since high school; ever since Matt had come to live with his aunts, Samantha and Mina, when he’d come of age. Samantha was his father’s stepsister, and Mina was her wife. So, family, but no blood relation. No one would bat an eye at that. The three of them lived less than a block from each other and had become regular staples at each other’s houses. They all used the back or side doors and didn’t even knock; and they called each other’s mothers/aunts, “mom/aunt” too. They’d stuck together all through high school. After they graduated at age 20, they attended the same local college together. Matt was secretly terrified at what would happen when they all graduated at the end of the semester. The thought of separating from them as they all officially entered adulthood and went their separate ways in the world always brought a knot to his stomach.
It was fairly common when a young man came of age for him to be sent off to live with non-blood relatives. That way, a young man could sow his oats and not worry about violating Escort any social norms. It didn’t always happen. For example, Kyle still lived with his biological parents. But there were strict rules at home, and he spent a lot of time at his neighbor’s house with their two slightly older daughters. Mother/daughter and sister/sister incest were commonplace, and no one batted an eye at all at that. In fact, if mothers and sisters didn’t regularly fuck each other, it was considered very odd! But male incest was still slightly taboo. Not that there was any chance of pregnancy or anything like that! Accidental or unwanted pregnancies had become unheard of generations ago! A woman basically couldn’t get pregnant unless she wanted to, thanks to breakthroughs in modern medicine. Technically speaking, it was as safe as sex could be. But it was still frowned upon in most of the United States. Although, as aways, Europe was a little more open minded. In fact, Matt had known several exchange students from Spain who had informed him that there was no such taboo back home.
“Mommy… Oh, fuck! Mommy!” cried Jessi as she sank her dildo’s entire length up her unbelievably perky ass and ground her buttocks down on Matt’s bed while she pounded her closed fist in and out of her sloppy cunt and came hard. She squirted a little onto Matt’s comforter for, not the first time. Her orgasm lasted for maybe fifteen seconds before she went limp. She lay there panting as she tried to catch her breath. Despite the young woman’s conversation being half private because of the earpiece, Matt could hear Charlotte – Jessi’s mother – cumming loudly on the other end of the line anyway. That must really hurt her ear, Matt thought.
“Was that one good for you too, Mom?” she asked after a minute or so, bringing her gooey right hand up to her face. “You do remember I’ll be home for Tuesday Night Endurance Training with Aunt Kim and Aunt Bobbi in a few hours? You could have waited until I got home and done all this to me for real, you know?” she asked as she played with her still stiff nipples with her left hand and began sucking the sticky fingers of her right hand clean. “Un, huh. Whatever you say, Mom. I have to go. Matt and I need to finish studying and I think he’s going to blow if I don’t take care of him. Love you too! Bye!” she said as she took out the earpiece and tossed it onto the nightstand with her phone.
“Did you at least enjoy the show?” she asked, propping herself up on her elbows to look at her best friend over her C cups.
“I did!” Matt replied. He’d pulled his pants down ten minutes ago and was idlily stroking his 11″ cock, patiently waiting for her to pay him some attention. He’d thought about joining her on the bed but didn’t want to interrupt her while she was talking to her mother. “You going to take care of this?” he asked, motioning downwards. Although he’d already fucked several girls earlier in the day, the sight of Jessi always got his dick hard!
“Well, considering that I made it hard, I’d probably better make it soft,” Jessi replied, sliding off the bed. She removed her uniform top and bottom and bra as she went. “It’s the only responsible thing to do after all!” she added. Crawling up to her friend, she pushed him back into his desk chair and crawled up onto his lap. Spreading her pussy lips, she lowered herself down onto his throbbing erection. Despite having recently fisted her own cunt, her front hole was well trained and gripped his pole like a velvety vice.
“Shit! That’s good!” Matt moaned as he felt the head of his cock bottom out in Jessi’s pussy. An inch or two of his shaft still remained outside of her body.
“You’ll have to hold my dildo, so it doesn’t come out,” she reminded him as she felt it begin to slip out. Really, this isn’t his first time fucking her. He should remember things like that without having to be told! She berated her friend silently.
“Sorry!” Matt replied as he grabbed the base of the 4.15″ wide dildo and slid it safely back inside Jessi’s ass. Her round breasts were right in front of his face. So, he did what any red-blooded American boy or girl would do: he picked one, bit down on the nipple lightly, and started sucking.
Jessi moaned as Matt went from one nipple to the other. She loved that! Her breasts were relatively small, but her nipples were incredibly sensitive! “You can get a little rough with my ass, you know,” she reminded her muscular friend for the hundredth time. “The dildo might feel better against you cock if you moved it around a little bit,” she suggested. And it’ll feel so much better for me while you fuck my cunt! she added silently.
After a few thrusts, God! Why is he so dense! Jessi asked herself Bayan Escort as she felt Matt finally start to fuck her ass with the dildo. Real men don’t have to be reminded of things like this! she continued in thought. Maybe I’ll visit Professor Anderson during his office hours tomorrow. I need to ask him a few questions about his syllabus anyway. And I always leave his office so sore I’m pretty sure I walk funny!
“Better?” Matt asked.
If you have to ask… she started to silently reply before, “Yes, better,” she said aloud.
Fucking boys! No appreciation for a proper woman’s anal wellbeing! It’s their cock and balls and nothing else matters!
Unlike the much more promiscuous Europe, most Americans kept their number of active sexual partners to a dozen or so. Usually these were limited to family members, coworkers, close friends, neighbors and people like that. Basically, anyone who might have joined you at the bar for Happy Hour a century ago was likely to be a sexual partner these days. Adults generally had their circles of friends and partners well established and didn’t need to venture outside their circles much. Younger adults in their late teens and early 20’s were still feeling their way out in the world and tended to be significantly more adventurous with their sexual encounters! Add to that the competition amongst young women for the woefully inadequate supply of young men, and you had the perfect recipe for behavior that any sane person from generations past would have called shamelessly immoral behavior! Matt was actually the third guy she’d had sex with today – not counting the two female teammates she fucked before practice and her mother before she’s left for school that morning – and it was only 5:00 in the afternoon! She liked him as a friend, but she didn’t see him as potential boyfriend material or anything! He was far too immature for her consideration! She needed a real man seeing after her needs.
Despite her aggravation at Matt’s inexperience and ineptitude, Jessi felt her orgasm building. Between her friend’s pleasantly thick cock, the dildo that he was finally starting to ream her asshole out with in earnest, and his teeth and limps on here sensitive tits, she was getting close. Out of the blue, she felt Matt’s hand smack into her meaty ass cheek shockingly hard. She couldn’t help but yelp in surprise, and a little bit of pain. She also felt herself squirt a little bit more.
“Sorry!” Matt apologized, removing his hand.
It took Jessi a second to reply, as the slap had almost pushed her over the edge. “No… No! Don’t be sorry! Do it again… Harder… Please…” you fucking asshole! Use me like a man should use a woman! she added silently.
Unsure of himself, Matt smacked her cheek again. And then again, a little harder.
“Oh, fuck… Matt! Spank me! I need it! I deserve it! Matt!”
Matt smiled and really let her ass have it! This feels oddly right, he thought to himself. He could feel the vibrations from impacts his hand was making against her buttocks in his cock. It felt good.
Jessi came hard and suddenly, squirting all over Matt’s groin. She felt a little embarrassed. She usually only squirted that much for Professor Anderson and her mother. It took her a minute to recover as she milked his dick with her well trained snatch.
“I’m gonna cum,” Matt whispered, as he kneaded Jessi’s red ass cheek with one hand and fucked her asshole with the dildo with the other.
Moving quickly, Jessi slid off Matt’s lap and sank to her knees. She licked the tip of his cock, savoring the flavor of her own juices, before effortlessly hoovering his entire 11″ length down her throat to his large balls. Her mother had made sure she was an accomplished cock sucker before her 20th birthday, and all that effort had paid off in spades! She bobbed her head up and down a few times and felt the head of Matt’s dick start to swell, announcing his imminent orgasm. Quickly, she pulled off and aimed the impressive tool at her small tits while jerking him roughly. She was rewarded for her efforts within seconds as rope after hot rope of white jism splashed over her tits.
Matt groaned in satisfaction. After a few heartbeats, “I was really wishing you would swallow it like most girls do,” Matt said, a little disappointed.
“Sorry,” Jessi lied. “I always forget,” she added with an eye roll. Men get to cum down my throat. Boys have to cum on my tits, she said to herself as she squeezed the last few drops out of Matt’s sizable cock. It’s too bad he’s not more sensitive to my needs. I could really get used to this dick if its owner knew how to properly treat a woman… she added as an afterthought. “I need to Escort Bayan go get cleaned up.”
“But what about the mess you left in my lap?” Matt complained, motioning to her squirt that was soaking the hair on his lower abdomen.
Jessi reached down to retrieve Matt’s discarded shirt. “Here you go,” she replied, tossing the garment to him. He muttered something unintelligible and annoyed under his breath as he began wiping the brunette’s squirt off his body.
“I’ll be right back,” she added aloud before he could protest further. Holding her dildo in her ass with her right hand, she collected her cloths up with her other and headed for the door and the bathroom to clean up. She almost ran into Samantha, Matt’s aunts, at the door.
The older blonde woman wore a thin green skin-tight T-shirt that left nothing of her 36E breasts or their large areolas and fleshy pierced nipples to the imagination. Her bald muff and shapely hips were bare underneath. Matt could see the 1/2″ thick dilation catheter locked into her urethra from his position, but not the base of the 6.55″ wide anal dildo that was locked inside her back hole. Although, the outline of the large tool was clearly visible underneath her trim abdominal skin as the sizeable latex tool made its way upwards to disappear underneath her ribcage. It was her usual around-the-house outfit.
“Oh, sorry, Jessi,” she apologized as she looked the young woman up and down greedily. “I was just coming to remind Matt that dinner is in half an hour. You’re more than welcome to stay as well,” she added. With one finger, she reached out to scoop up some of her nephew’s cum, which was running down the side of Jessi’s boob. She quickly sucked it clean and nonchalantly reached out to scoop up another blob.
“Thanks, Auntie! But I have training tonight with my mom. Her sister and her wife are coming over for Tuesday Night Endurance Training. I’ll have to go home as soon as we’re done studying,” Jessi replied to Matt’s aunt.
“That’s too bad,” Samantha said, offering a cum-covered finger to Jessi’s lips. Not wanting to be rude, she opened her mouth and let Matt’s aunt wipe her finger clean on her tongue and lips. Matt’s spunk actually doesn’t taste too bad, she concluded. “You know you’re always welcome for dinner!” she added, scooping up a third finger of her nephew’s seed.
“I know, Auntie,” Jessi said as Samantha stepped aside to allow her to pass. “But I really need to be headed home.”
Stepping into Matt’s room, Samantha watched her only nephew pack his thick cock back into his pants as she sucked his fresh cum off her finger. When is he going to grow up?! she wondered to herself for the umpteenth time. “Did you hear me, honey?”
“Yeah, Aunt Samantha,” Matt replied. “I’ll be down in a bit.” He was more than a little angry with himself. He heard what Jessi didn’t say. He needed to be more mindful of a woman’s needs. When am I going to grow the fuck up? he asked himself. “And Jessi’s cunt drooled and squirted all over my bed again…” he complained. Again, the words of the woman from the gym echoed in his brain: “Young men usually do around your age.”
Samantha looked over at the small pool of viscous gash juice and the stream of squirt that had been shot downwards and sighed. The stain and fluid resistant comforter didn’t absorb the juices at all. Matt really should have made her clean that up before fucking her, she mentally said. “Well, that was rude of her,” she said aloud as she walked over to his bed and knelt down, groaning as she did so as the thick faux cock in her ass forced her organs to rearrange themselves as her torso shifted. More for me, I guess, she said to herself as she began sucking up the young woman’s delicious pussy juices.
As his aunt sucked and licked his comforter clean, Matt was treated to the delightful view of his aunt’s shapely upturned buttocks, the thick black base of her 6.55″ wide dildo spreading her cream-colored cheeks, and her empty and slightly agape cunt just below. Something about that ass screamed “I need to be spanked” and her pussy looked like it could use a good fucking from a hard dick. And deep down inside Matt, something started to click.
“All cleaned up,” Samantha announced after a few minutes. “Your comforter just needs to dry, and it should be good to go by bedtime.”
“Thanks, Aunt Samantha,” Matt said, still watching the mostly nude older blonde woman.
“I’m going to go check on Jessi,” she said, turning to leave. Matt watched his dad’s stepsister’s ass sway out the door before returning his attention back to his studies.
After a few minutes he heard Jessi’s voice waft out of the bathroom down the hallway and into his bedroom, “Oh! Auntie Samantha! Right there! Right there! Fuuuuuck!!!” accompanied by wet squishing noises that sounded suspiciously like a fist pounding into a recently well fucked cunt.
Well, I guess Jessi is done studying for tonight, Matt concluded.