The Life of Ryan - Cover

The Life of Ryan

Copyright© 2019 by Smoothie75

Chapter 23: Troublesome Twins

Erotica Sex Story: Chapter 23: Troublesome Twins - Ryan Sheaffer is the ultimate playboy: 23 years old, spoiled, and hot as fuck. After experiencing some deep personal tragedies, he buries his grief by creating a lifestyle that satisfies his incredible sex drive. He relentlessly pursues extreme carnal indulgences...pushing himself and his many companions to their sexual limits. The young women and men who become part of his life have no idea what they're in for once he gets started...because there has never been anyone quite like Ryan.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   mt/Fa   Fa/Fa   Ma/Ma   Ma/mt   mt/mt   Mult   Consensual   Reluctant   Gay   BiSexual   Heterosexual   Fiction   DomSub   Light Bond   Group Sex   Orgy   Anal Sex   Analingus   Cream Pie   Double Penetration   Exhibitionism   First   Masturbation   Oral Sex   Sex Toys   Tit-Fucking   Voyeurism   Nudism  

No one got up very early the next day, but later in the afternoon Chad came over, and he, Ryan and Matt headed down the crude stairs off the bluff behind the back yard, down to the beach. Despite living right on the beach, Ryan hadn’t been down there in a couple weeks, and it was a perfect afternoon for skimboarding. The tide was in at just the right level, and there was a long, smooth flat section of beach just a little ways down from Ryan’s house. The three young bucks spent part of the afternoon throwing down their boards and skimming across the water.

Jenna and Kerri took longer to recover from yesterday, but around 5:30 they made their way down the stairs and path to the sand. The boys were treated to the always welcome sight of their toned, luscious bodies and perfect racks clothed in very small bikinis. They laid out on towels to watch the boys. About 20 minutes later, Lydia and Andre came down to deliver a large basket full of Lydia’s signature barbecued chicken dinner, one of Ryan’s favorites, and set up a short table and beach chairs.

There were many people on the beach this afternoon and evening, but with it being private for the homeowners who lived alongside it, there was still plenty of space. Ryan’s next-door neighbors were Rochelle Miner and her 16-year old twin daughters, Sabrina and Selena, the ex-wife and children of a very well-known Hollywood movie studio executive. With all the privacy fencing and foliage between their properties, Ryan had only met them a couple times before, but was savvy enough to tell that these girls were t-r-o-u-b-l-e. The blonde Barbie dolls were spoiled rotten mischief-makers, and their mother was usually too drunk to keep up with them. Occasionally Ryan had spotted other semi-famous Hollywood youth on the beach with the girls as guests, and by chance, Marcia LeCarre, one of his old modeling agents who had become quite a power player was there with them one day. She was very excited to see him again, especially his now-adult but still lean and gorgeous body, which was clad only in a Speedo as usual.

Today, the twins and three teenage “pretty boys” came down to the beach to hang out and smoke on a small wooden deck that had kind of been built at the bottom of the stairs leading down from their backyard. The girls had been tuned in on their hot young neighbor since they first met a few months ago, but this was only the second time they’d seen him down on the beach frolicking in the surf, mostly unclothed, with his friends. Their own beaus had to endure the girls blatantly ogling Ryan, Matt and Chad through their binoculars, and wished they would go inside.

Ryan’s skimboarding took him down the beach a little ways until he was nearly in front of the teens, who he hadn’t taken notice of yet. When he landed on the board wrong one time and went crashing into the water and sand, he heard them laughing at his folly, and turned around and flipped them a goodnatured bird and a smile. Now, he knew they were watching, and so did Chad who was nearing that area on his own skimboard. They showed off some tricks and continued having fun, and soon, two of the teen boys ventured down to see if they could try out their skimboards. Jake and Dylan were two cool cats. Jake was a classic all-American jock type, not very tall, but very muscular for a 17-year old. Dylan was a thin, smooth, blonde, 16-year old who was way, way too cute for his own good. Ryan secretly wished they weren’t so young, but still enjoyed looking at them and hanging out in his Speedo with them for a bit.

Chad gave the teens a few lessons in skimboarding, something he was really good at. Soon, the girls and the other boy, Todd, came down to hang out and visit with them and watch Jake and Dylan make fools of themselves trying to get the hang of this new sport. Todd was a slender, light-skinned emo model princess boy, with spiked black hair, several earrings and piercings, and a few tattoos.

“So Ryan,” Selena suddenly blurted out, “do you like our new bikinis?”

“Uh, yeah ... very hot,” Ryan said hesitantly. Indeed, they were pretty fucking awesome ... about as minimal as you could get without looking like you were trying to look like a stripper, and on two young, firm, toned, tan young vixens like the twins, both of whom had the most perfect, large breasts that you could stare at for days. “You like mine?”

The girls and Todd all laughed out loud.

“When are you going to invite us over for a pool party?”

“When you turn 18. Why, don’t you have a pool?” There was a tall, thick hedge between their yards as well as a row of trees inside the hedge on both sides, providing a thick border of privacy. He knew they obviously had a pool, but thought it was an odd request from this young girl.

“Well of course we do, but if you’re having a party at yours, you should invite us over.”

Ryan grinned. If they only knew. Or ... did they?

“I don’t think your mom would like you coming to my ‘pool parties’, ladies. They’re usually not ... uh ... PG-13 type of events.” Ryan winked at Chad and they both chuckled.

“Well we’re not 13,” she said.

“Yeah,” Sabrina chimed in, “you’d be surprised how ... very mature ... we are. She lifted her bikini top to flash Ryan some tit. Jake took notice and came to check the conversation ... and the tits ... out.

“Oh shit ... don’t do that, you’re...”

These teen babes were actually propositioning him. Ryan’s cock was indeed swelling a bit. He certainly had enough ass in his life already, but damn these kids were hot ... especially the twins. He decided to not make it easy for them though. “Sorry girls, I live right next door to your mom...”

Selena laughed. “Even when our mom is sober, which isn’t often, she doesn’t really give a fuck, so neither do we. We aren’t gonna get in trouble for going topless in your pool.”

“Depends on what you mean by ‘in trouble’ ... and besides, at my pool, things don’t just stay R-rated either ... sometimes they get X-rated. I have lots of friends over, but they all are at least 18 and know what the deal is at my house.”

“Dude,” Jake piped in, “we’re in to crazy shit you know, like whatever. We’ll fucking whip off our clothes and fuck for you right here, right now if you want! We don’t care.” Selena grabbed his crotch and started rubbing a growing erection in his shorts. “If you’re having sex parties, let us in on them, man, there’s lots of older people who would love to get their hands on this,” he said, grabbing his own crotch too, “and THIS!”, he said, grabbing a handful of Selena’s tits.

He wasn’t wrong about that. Except Ryan didn’t really have any “older” people over for such things, unless being in your mid-twenties was considered old. Ryan realized they must have already spied on him and his companions when they were up to naughty things at his pool before. His first thought was YEAH, he would LOVE to watch these two hot-bodied teens fuck. And he didn’t mind that they were approaching him about this, since normally he’d love it...

Selena flashed him her tits next. “We’re not little girls, are we? Besides, we do what we want, just like you used to.”

“You’re still pretty young, and ... how do you know what I used to do?”

Jake answered that one. “Dude, Lacey Nichols is my big sister, and she’s told us all about you in high school.”

There was a name Ryan hadn’t heard in quite awhile. Lacey went to the same high school he did. She was a year older than him, quite a party girl, and though he had not ever slept with her, she was best friends with a couple girls who had themselves draped all over Ryan during his junior year. She would definitely have known about his wild exploits then, and if she shared that info with these kids, there was no point in being hypocritical about age barriers. Ryan himself had indeed hooked up with several college students and even some older women when he was their age.

He took in a deep breath and steeled himself to resist. “Man, you guys are awesome ... and very tempting, but we’ve got to get going,” Ryan replied, pretending to not be interested. Of course, he already knew it was only a matter of time before he got to show these cocky teenagers how to REALLY fuck, but for now it was fun to hold them in suspense and deny them what they wanted. Ryan loved that they were all fascinated with him and eager for his aura; it was fun to be the object of someone’s fantasy and keep them at bay, like he did on his webcam shows. However, the problem with a Speedo is that you can’t hide much, and his arousal was becoming more clear.

Selena slid over to Ryan before he could back away, and put one hand on his shoulder and the other on the bulge in his Speedo, which she gave a couple loving strokes to. The head of his cock was just about peeking out the top if you looked right down on it, which she was doing.

“See? You do think this would be good ... very, very good ... and my sister and I are going to be on a mission now, so you may as well figure out you won’t be able to resist us forever. See ya soon!”

With that, she raised her head up and kissed him on the lips, gave his crotch a final pat and turned to head back towards the stairs up to her house. Todd and Sabrina had already started back. Jake, having noticed Ryan checking him out as well as Selena, made a bold move and opened the top of his board shorts. He whipped out his thick, hard cock and gave it a couple of strokes in Ryan’s direction, and said “If you’re not going to fuck her today, then I think I will. My monster here is ready to have a fucking awesome time. Hey, have you ever had identical twin babes like these at the same time? It’ll blow your fucking mind, dude!”

With that, he put himself away, hollered to Dylan, who was still skimboarding with Chad, and headed back up the beach as well. Dylan was really enjoying learning this skill, and chose to stay down at the water with Chad, who was also enjoying himself in the water today.

Ryan burst out laughing and rolled his eyes, and remembered all the crazy, bold things he did to get laid as often as possible in high school himself, including with people much older than himself. Heck, he still thought of himself as a very young person now, at 23. As he turned to walk back towards the beach in front of his house, he couldn’t help but reach in and grab his own cock and rub some of his precum around the head.

When he reached Matt and the girls, they took notice of his huge erection as he approached.

“Uh oh, those girls down there are putting their moves on you now too,” Matt said. “They are baaaaaaad!”

“You’ve met them?”

“Oh yeah. A few weeks ago I was down here by myself, and they came over and practically tried to rape me right there on the beach. They thought I was their age.”

“Well you’re only three years older. Damn, they sure are hot. I’m sure it will happen eventually if they want, but right now I’m having all the sex I need without going after teenagers.”

“Ry, we need to have them over and fuck the shit out of them. Can you imagine how awesome you and I would be tag-teaming them together? We’d go nuts. Besides, no one in your neighborhood gets in trouble for anything; you’re all too rich and powerful. I want us to fuck ‘em sometime! They’re twins and they’re 16!”

“I know that... , “ he sighed, “well ... maybe ... we’ll see.” The idea appealed to him quite a lot, to tell the truth.

Kerri stood up. “Well, c’mon Jenna, I guess us old ladies ought to get back to our crochet and bingo.”

Jenna feigned arthritis, rising slowly and painfully. “Oof ... oh yeah, we’ll leave the sexual relations to all the young ‘uns. Maybe if I can find my glasses, I’ll get back to my bedroom, and you can come in and see if we can remember how to have sexual relations with me, like when we were younger.” Ryan and Matt roared with laughter.

“Too bad, Jenna,” Kerri said, leading Jenna up the path, “that looks like a mighty nice boner that young boy has in his little shorts. It sure would be nice to suck on it if we were still young enough.”

Ryan, smiling, snuck up behind them and pinched their asses.

“Ooooh, you naughty young man! Now is that any way to treat a lady?”

“When I’m done with you, you are definitely not going to feel like a ‘lady’, my dear,” Ryan said in a husky voice. “You’re going to feel like a well-fucked slut covered in my cum and not interested in walking for awhile!”

Ryan and Matt chased the girls up the stairs. Clouds had been rolling in, and a few raindrops began to hit their bare skin. Ryan lead them up the back stairs to his veranda, and through the French doors to his room as they all shed their swimsuits on the way. He headed into his bathroom and turned on all the heads in his giant shower closet, pulled the bench out to the middle, and motioned them all in. It was time for a shower orgy.

After a couple minutes of kissing and groping under the showers, Ryan had the girls kneel on opposite sides of the marble bench and lean across it. He had no interest in oral sex or foreplay right now; he just wanted to fuck really badly. Matt and Ryan each positioned themselves behind a girl, put their cockheads at the entrances to their pussies, and drove them in deep and hard. Gasps and moans came from all four of them as they began a “core four” orgy, as Ryan nicknamed them. Each of them enjoyed the variety of new partners that their open and adventurous relationships allowed them, but there was something extra exciting about the times they would get together for their own foursomes once or twice a week.

As Ryan passionately drove his cock in and out of Jenna’s hotness, his eyes feasted on sexy, tight little Matt directly across from him, fucking Kerri as hard as he could. He loved watching every shiny, lean muscle on his toned, youthful frame. He loved watching his nice cock going in and out of Kerri. And he loved the intense facial expressions and grunts of pleasure that showed how excited Matt really was. His own cock was starting to pump faster and faster into Jenna’s tight, wet pussy, while his hands grabbed her perfect ass and slammed it back towards him with every stroke. Jenna started whimpering and gasping, and soon launched into a strong orgasm, pounding her fists on the bench and shuddering with intensity.

Kerri came just a few moments later, but the boys continued rutting away. Ryan tried the same thing out on Jenna that he had with Amy earlier in the week; pausing as her orgasm crested to let her absorb her own body’s feelings, but then starting to thrust furiously again just as she thought her orgasm was ending. Always a hypersensitive little nympho, Jenna started freaking out and thrashing around, wanting desperately to both stop Ryan’s onslaught and fully accept it and relish it at the same time.

The steam from the hot shower surrounded them, the spray made them all slick and shiny, and the sex raised their body temperatures even higher. For a full 20 minutes, Matt and Ryan continued making the girls cum again and again. Finally Matty couldn’t hold out any longer, and with a long, expletive-filled scream, he doubled over on Kerri’s back while his cock spewed a lengthy series of ejaculations deep inside her pussy.

It was so hot to watch Matt cum, because he was a guy who felt every physical sensation very deeply, and his orgasms were always overwhelming events that were very exciting, almost comical, to watch. Ryan’s lust always increased dramatically when watching anyone cum, but especially Matt ... it was as if he could feel part of Matt’s orgasm within himself. “Fuck yeah, Matt! Cum like a sex freak! That’s hot, yeah, cum more, more, more! Keep cumming you hot little fucker!”

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