A Proper Young Mans Guide To Anal Etiquette Ch 08

A Proper Young Man's Guide to Anal Etiquette

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.

8. Morning Commute

A couple days later, Matt was pulling his car out of the garage on his way to school like he did every morning. His car was nothing to brag about, but his father had bought it for him for his 21

st

birthday and it was his. And he was proud to have it! Most young people his age didn't have, nor did they particularly want one. They were fine with having their relatives, friends, or neighbors drive them around. Or just using ride sharing. Matt never quite understood the lack of interest in the freedom that a car brought that most of his generation lacked. But he didn't care. He loved being able to drive himself wherever he wanted to go, when he wanted to go there!

As he was monitoring the screens to make sure the car's AI didn't hit anything while moving, he jumped when an alert chimed to let him know that a pedestrian was too close, and the car automatically braked to a stop.

What the fuck?!?

he thought to himself. Sure enough, there were feet in the pickup just behind his door. Cranking his neck around, he was surprised to see Jessi walking up to his heavily tinted window. Rolling it down, "What the fuck are you trying to do? Be the first person on the planet in twenty years to get hit by a damn car?!?"

"No, fuck face! I was waiting for you," she answered with an eye roll. "Unlock the door," she demanded, walking around the front of the car to the passenger's side. Matt had to admire the petite brunette. Her long hair was up in a sexy ponytail. She wore a tight red crop top that ended an inch or so below her nipples and no bra. This did an amazing job at showing off her amazingly perky 30C breasts and hard nipples. Her short, pleated skirt barely covered her bubble butt. In fact, as she walked, her skirt would blow up and from his lower point of view seated in the car he could see the crease her buttocks made in her skin as it met the backs of her thighs, which was his favorite part of any butt! If the skirt were any shorter, he'd have been able to see the base of her daily anal plug. Which wouldn't have been proper at all! Her midriff was bare today. Obviously, she was wearing a plug or a short dildo today, not a full-length dilator dildo like she normally did, or he'd have been able to see its outline underneath her skin clearly. That would have been incredibly improper!

Without a further word, she opened the door, slid inside, tossed her small bag in the back, shifted her bottom from side to side until she felt her stubby dildo engage with the seat's magnetic hardpoint, belted herself to the seat, and looked at Matt expectedly. "Ready when you are."

"Really? You've always had your mom or your next-door neighbor, Rich, drive you to school. I've told you I could bring you along with me you for years and you never took me up on the offer. What gives?" the young man asked curiously.

Jessi smiled shyly. "Well, everyone knows the proper payment for a girl getting a ride from a guy is sucking him off at the destination. And you've always been so immature - like most guys our age, to be honest - that I didn't want to. But after the other night when you fucked my brains out and fed me your cum a few times, I figured I might as well start riding with you," she answered while looking him straight in the face. "Sorry. Nothing personal about before," she added apologetically.

Matt looked back at his best friend for a few seconds before smiling. "No apology needed. And you're right. Women should have their anal wellbeing taken care of first, and then treated like fuck toys afterwards," he said, smiling larger.

"You finally get it!" the young brunette replied with an overexaggerated jazz hands. "Finally!!!" she added with a friendly giggle.

Matt joined her in a good laugh. "But you know you can't ride in a car like that, don't you?"

Coyly, the lithe brunette replied, "Why, whatever do you mean?"

Unbuckling himself, Matt sat up on his knee to better access his friend. "From now on, show up 15 minutes before I normally leave so I can get you properly situated and we're not late to class like we're going to be today after you repay me at school," Matt said sternly as he grabbed Jessi's ponytail and firmly pulled the petite woman forward.

"Yes, sir," she replied meekly. She moved her arms behind her without being told and let them slide through the hole in the back of the seat as Matt pushed her backwards again. She felt her elbows touch as they were pressed together once her shoulders again touched the seat.

"And wear a full-sized dilator dildo from now on too," he continued as he grabbed her right leg and brought it up to a waiting cuff on the seat's top right corner. With a soft click, it was secured in place.

"Yes, sir," Jessi replied even more obediently. "Only full-sized dilator dildos to school from now on," she confirmed as her left leg was similarly positioned to her other side. Now both legs lay several inches behind the plane of her torso.

"Good," Matt said absentmindedly as he pulled up her crop top up to her neck to expose her smallish breasts. He gave each nipple an extra hard twist for good measure, which elicited a cute squeak of pain and half protest from his best friend. Finally, he pulled the front of her skirt up and tucked it into the waist band to expose her bald and dripping cunt. Her pisshole was filled with a .35" thick catheter topped with a green gem. Sitting back down, Matt tapped a few commands into the car's center council and Jessi's slightly gaping pussy and stuffed full asshole appeared across the car's 24" main screen in high definition for a small camera mounted to the front of the passenger seat.

"Now this is how you'll be riding in my car from now on," he said with finality as he repositioned himself and buckled his safety harness.

"Of course, sir," Jessi said, moving her shoulders and hips from side to side to get comfortable in the semi-extreme position. She often found herself in more stressful positions at home, but this still took some getting used to.

"We'll start off with a medium pace for the first few miles. I'll adjust it once you've had a few good asscums and we're on the highway," he commented as the seat's hardpoint started to thrust up and down.

Jessi let out a soft cry of surprise as her asshole was suddenly violated. It was anything but unexpected, but it still caught her off guard. It always did.

"Is that an oversized plug?" Matt inquired. A normal butt plug had a smaller neck just behind the wide part where a woman's asshole would sink into to keep it from falling out. An oversized plug meant that part of the plug just inside the anus was inflated after insertion so that it was too big to slide out past her sphincter. This was normally called the plug's knot.

"Yes," the brunette confirmed. "It's about half an inch larger than my maximum dilation. It's not coming out until it's deflated."

"Good." he replied. Matt played around with the power settings and thrusting depth for a few seconds until he was satisfied with what he saw on the car's screen. Jessi's poor anus was being yanked downwards harshly as the seat tried to jerk the large plug right out of her overstretched hole. Of course, that wasn't possible at its current size. So, the young woman was just tugged down into the seat, only to bounce back up once the hardpoint shot back upwards. The mass of the plug's 4.85" wide knot pulled her abused anus down and away from her shapely buttocks until it formed a cone of downwards pointing flesh. The plug's 4.15" wide neck was almost completely extracted from her colon before it sank back inside.

"Oh, fuck!" Jessi cried out slightly louder. But to her credit, she didn't ask him to turn her seat down. "You'll stretch me out to a larger size in no time if this keeps up!" she half complained, half requested through gritted teeth.

"Good point. Let's alternate full-sized dilation dildos and oversized plugs. Sound good?" he asked. Although, it wasn't really a question.

"Yes... yes, sir," she replied.

A knock on the driver's side window distracted him momentarily. Glancing over, he saw his Aunt Mina bent down and looking confused. Rolling down the window, he simply asked, "Yes?"

"Why are you just sitting in the driveway?" she started to ask as the heavily tinted window was lowered. "You're going to be late for... oh!" the Filipino and Japanese woman said in surprise. "Jessi! I didn't know you were riding with Matt this morning!"

"Hi... Aunt Mina... beautiful morning... this morning... isn't it?" the young brunette asked as she bounced up and down on the seat.

"Jessi will be riding with me to school from now on," Matt explained.

"Ah. I see. Well then, drive safe, honey!" Mina said, standing up and turning towards her own car, still parked in the garage.

"You too, Aunt Mina," he replied. Matt watched the older woman walk away as he rolled his window back up. She really did have an amazing ass!

Turning his attention back towards his passenger. "Well, let's get this show on the road!" he said, shifting the car back into reverse and navigating it towards the highway. "Would you like me to turn up your seat a little?"

Jessi was moaning pretty consistently now, and she almost didn't hear Matt's question. "Yes... yes please... Matt."

"Do you need to asscum that badly?" he asked, tapping the seat's power dial, but not turning it.

"Yes! Jessi needs to asscum that badly!" she half demanded.

Matt only smiled as he turned up the seat's power by a few notches.

"Oh... gods yes! Thank... thank you... Matt!" was her only reply before her moans grew louder and her head lulled back against the rest.

"You're welcome!" the large young man replied. He sat back to enjoy the show.

Fuck! My dick is hard!

* * *

"There we go. All the way down to the base, like a good little slut," Matt groaned as Jessi's head bobbed up and down in his lap. He was so fucking horny by the time he'd parked the car in the multi-story parking garage that it was all he could do to hold back from blowing his load down the young woman's talented throat immediately.

The young brunette turned her head to the side slightly to look up at her best friend straight in the eyes as she felt his 11" cock start to twitch down her throat. She knew he was close. She was pulling up an inch or so, only to slam her head back down until her lips met his public bone. Most guys loved this move, and Matt was no different. Finally, she felt his head swell and she knew his flood of jism was coming in only seconds whether he wanted to hold back to enjoy her oral hole more or not. Immediately pulling back until just the tip of his dick was between her lips, she said in a husky voice, "Thank you for all the asscums, Matt! I think I made the right choice to ride with you from now on. Can I have my snack now?" she added sweetly before locking her lips around the head of his cock, applying a shocking level of vacuum, and jerking his shaft with her hand.

"Fuuuck...!" was all Matt could say in reply as rope after rope of his hot cum exploded into the young brunette's mouth. His hips bucked up and down ever so slightly as he emptied his balls. Jessi was an expert at blowjobs and didn't spill a drop though. Finally spent, he collapsed back into his seat to catch his breath. Jessi milked his shaft for several seconds with her soft fingers to ensure that every drop of his orgasm was safely deposited in her mouth before releasing his head for her strong lips. She gave the expended gland a kiss on the tip before sitting up. Still looking at the young man, she made a good show of swishing his cum around in her mouth, savoring the salty flavor. She opened her mouth several times to show him his seed coating her mouth and pooling on her tongue. After a minute or so of Jessi showing off, Matt finally said, "Swallow."

With the single word, the petite brunette did just that. She then reopened her mouth to show him that she'd swallowed it all like a good little girl. "Can I have more tonight?" she asked, licking her lips. "We're supposed to study again. Although, the flavor is missing something," she added as she played with her still uncovered tits.

"Oh?" Matt inquired. "And what is that?"

"Well, your cum tastes much better when it's mixed with my cunt juices," she replied with a smile.

"Ah," Matt said with an equally large smile. "That makes sense!"