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 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 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.
