The Life of Ryan
Chapter 32: Miami, Days 2 & 3

Copyright© 2019 by Smoothie75

Erotica Sex Story: Chapter 32: Miami, Days 2 & 3 - 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  

In the morning, Ryan and Danielle had sex in bed and again in the shower before heading into a long day of meetings and appointments. Ryan was a little wiped out at first from the night before, but after some coffee and a high-protein breakfast, he felt rejuvenated enough to become a major businessman for the day. Much was accomplished in the final negotiations of the terms of the merger that day, and Ryan played his part well. He knew he was more of a figurehead than anything else, but as such, he was involved in some very high-level discussions and planning sessions. He relied on Alison and Paul quite often to explain things to him since some of this was definitely above his level of understanding, but with his education, brains, and overall familiarity with his father’s company, he was able to keep up with a lot of it too, and even offer some opinions and suggestions here and there.

He was able to wink at Jasmine and subtly flirt with her from across the table during one meeting, and was amused to see she was noticeably distracted and didn’t speak quite as smoothly as she was known for doing in such proceedings. He was also able to grab Danielle’s ass once during a coffee break in the break room, and pull her to him for a quick but passionate kiss. He whispered very nasty, tempting things in her ear, which he then also nibbled on and growled into, and pulled away just in time to avoid being caught by one of his own executives who walked in right then. But the most surprising part of his day was that Alison ... his liaison and Paul’s executive assistant ... kept looking at him and finding reasons to talk to him. She seemed to always be checking on him and kind of ... hovering ... even when he didn’t need her. For someone who is always being hit on by women everywhere, it was obvious to Ryan what she was doing, even if she didn’t realize it herself.

The first day’s business was concluded by 5:00, and the representatives of the Sheaffer Group were scheduled for a dinner cruise that departed at 6:00. They loaded into several limousines to transport to the docks, which, with traffic, were a good 40 minutes away. Ryan was supposed to share a limo with Paul, but Paul received a phone call mid-afternoon that his wife had been in a serious car accident back in California. She was in the hospital in stable condition with some broken bones and injuries, but Paul needed to fly back home immediately to be with their young children. Ryan wished him well, and made a note to send a catering service to his home for a couple weeks to help with meals. He also made up an excuse for needing to confer with Paul’s secretary Danielle, and had her join him in his limo.

Within a minute of the door closing, both Ryan and Danielle threw their garment bags in the far end of the limo, and frantically kissing and tearing each others’ clothes off.

“Spent that entire day in a suit and tie...” Ryan gasped, “trying to conceal a hardon in all those meetings...”

“Oh yes,” Danielle growled, “I was climbing the walls today thinking about your cock! I need it!” She had his pants unbuckled and unzipped, and reached in to grab his hard pole.

“Gonna fuck the daylights out of you between here and the boat dock...”

“Yes do it! Oh fuck, you make me so hot!”

“Get those fucking clothes off then!”

90% of their clothes were viciously separated from their bodies within 30 seconds, and Danielle straddled Ryan and lowered herself down on his wonderful cock and began pumping herself up and down. Ryan buried his face in her breasts and kissed and bit her sensitive nipples while he rammed his cock up into her ravenously. His 8 ½ inches plunged up to her cervix as she rode him, and soon he laid her back on the car floor and assumed missionary position to keep plundering her depths.

“Fuck me harder!” she screamed. “Yes! Give me that cock! Give me that fucking! Yes!”

“You like that? Yeah ... I’m like a caged animal today, just let out, and now I’ve just got to FUCK ... oh yeah ... gotta slam my cock into you so hard now! Ugh, ahhhhh ... yes!” Ryan came hard inside her, but barely rested a few seconds before continuing to slam his cock in her like a jackhammer.

Traffic and busy city streets rolled past them through the limo’s windows, and the hot fucking couple just kept going at it for another 20 minutes. Danielle had her face pressed against the window, her ass in the air, with Ryan’s cock plunging away doggy style when finally he announced he was about to cum again. An intense but blissful look came over his face, and he grunted and unloaded a delicious load of cum deep inside Danielle, and then collapsed on her back.

Just 15 minutes later, they both emerged from the limo at the dock, dressed in their “classy casual” attire for the dinner cruise, and looking just a little flushed and tousled.

An hour later, Ryan was finishing an incredible seafood dinner served on board the ship. He had been cornered by one George Thomason, the CFO of the company merging with Sheaffer, and his wife Claire. They had insisted Ryan sit at their table, and had been talking non-stop about their amazing, beautiful 26-year old daughter Zoe. They had shown Ryan a dozen pictures of her on his phone, and suggested Ryan meet her sometime. Ryan was amused to realize they were trying to hook him as a catch for her, and imagined parents in another generation who would go so far as to arrange marriages for their grown children. Truthfully, Zoe was fairly decent-looking and sounded pretty smart, but she lived in Connecticut and Ryan was certainly not looking for a girlfriend or wife. He politely made small-talk with the Thomasons and the other people at his table. About the time he was done eating, Jasmine happened to catch his eye and recognize that he needed rescuing.

“Ryan, there’s someone I’d like you to meet ... do you have a minute?”

“Oh, certainly. Excuse me, George and Claire, it’s been nice chatting with you.”

“Well come on back when you have a chance. Maybe we can get Zoe on Skype and you two can meet!”

“Ahh, well, we’ll see. Thank you!” Ryan winked, taking backwards steps to walk away, with Jasmine pulling his shoulder gently.

Jasmine pulled Ryan out of the buffet and into the corridor.

“Sorry about them – they’ve been trying to get successful, rich young men interested in their weird daughter for years. She’s a smart one, but she’s got some ... personality quirks that are pretty annoying when you meet her.”

“No problem, I’m flattered. I’m not even what you’d call successful just yet. I just inherited all this.”

“You seem like a successful person nonetheless. You carry yourself like an entrepreneurial young professional.”

“Really? My acting skills are better than I thought then. I’m actually a pretty big slacker and partier most of the time!”

“Yes ... we know about that too...” she said with hesitancy in her voice. ‘Before this merger, I was assigned to research you in particular ... who you are, what makes you tick, what kind of man you are ... I never imagined I’d be drawn to you myself, but I knew your story and some things about you. It made us wonder if there was anything of substance when it came to you in the role of business owner ... but guess what? When you are involved in your dad’s business, you do come across as a leader. A young and maybe too casual one, but definitely a sharp and successful person.”

Ryan smiled at her. Honestly, this was good for him to hear.

Jasmine winked at him. “I also know of another way in which you are ... highly ... successful.” She grabbed his crotch and massaged what she felt there, while kissing him and pulling him near to her.”

“I keep thinking I want to be more than just a hard-fucking playboy, but there’s really no way to stop myself from enjoying this all the time,” Ryan said, as Jasmine unbuckled his belt. “It makes me feel incredibly good, super powerful, and I have sooooo much fun... (ooohhh, yeah, grip my cock like that!) ... so I just go with it.”

“For now, just go with it for me then. Ah, have you been a busy boy already this evening?” Jasmine noticed the moistness of his cock and the warm drizzles of cum on the inside of his boxers. He had unloaded two floods of cum deep in Danielle’s pussy less than two hours ago.

“Yes ... twice in the limo on the way here ... but don’t worry, there’s more where that came from ... literally.”

“Wow. Okay then. But we better not do this right here...”

Jasmine pulled Ryan’s untucked shirt down over his cock, which was protruding above the waist of his pants, and lead him down the corridor and down some stairs. The dinner cruise ship wasn’t a huge one, but it was large enough to accommodate up to 3 groups at a time. The Sheaffer group had the biggest entertainment room on the top floor, but below it was a level with two smaller facilities that were empty. They found their way through the darkened room and out on to a deep patio set up for entertaining. It was an open-air deck, but extended further into the ship than the balcony of the upper deck, so no one above could see people below them.

The horny couple found a wide, padded bench against one wall, and Jasmine quickly rid Ryan of his pants and boxers while he unbuttoned his shirt. She laid him back on the bench, and engulfed his long cock in her mouth.

With the ocean breezes, the motion of the ship, and the sounds of the party going on right above them, Ryan stretched out and relished every moment of this blowjob, which was quickly rejuvenating his cock. Jasmine tongue-bathed every inch of it, from the smooth area behind his balls to the head of his cock. As she rolled his balls gently in her mouth, his hot 8 ½ inch shaft towered above her face.

“I’m going to fuck you now,” she said, “and we’re going to be very quiet. You might be the boss in your company, but I’m not, and I could get fired for something like this.”

“I would never allow it, though,” Ryan told her. “Technically, after tomorrow, you’ll be working for me ... and I know true talent when I see it.” He winked at her. Jasmine, still mostly clothed, stood and removed her panties from under her skirt and straddled Ryan’s mostly naked body. His cock found her pussy, wet with anticipation, and soon they were intimately connected, rocking away in the warm ocean breeze.

45 minutes later, Jasmine returned to the upper deck with a fresh load of cum squishing around in her pussy. Ryan remained below for awhile, partly so they would not reappear together and make it too obvious for anyone who might have been looking for them, and partly because he was tired and very satisfied, and enjoyed lying there on the bench looking at the ocean and gently massaging his softening cock. He did not notice the 38-year old, blonde executive assistant who was watching him from the deck’s entryway. Alison had said hello to Jasmine as she re-entered the party room above, and noticed the “just fucked” look on her face. She said nothing about it, but went looking in the direction Jasmine had come from, and now she stood here ogling her young boss’ incredibly sexy, lean young body and that gorgeous cock ... no wonder he was pretty much “sex on legs”. She quietly reached into her panties and fingered herself as she indulged her voyeuristic desires and visually soaked in every detail of Ryan’s exposed flesh. If there was only a way that she could ... no, not allowed, no way ... but if only...

Alison continued fingering herself while admiring Ryan, who was sitting on the bench, leaning back against the wall behind him with his hands clasped behind his head, watching the ocean and enjoying the cool air on his sweaty body. Alison had two fingers inside her pussy, and now her thumb and finger from her other hand were playing with her clit. The boat hit a small wave that gave her a little jolt, and Alison gasped out loud as she almost triggered an orgasm. Ryan heard the little gasp, and quickly looked to his side and saw Alison turning beet red and hustling to try to pull her panties and skirt back up.

Ryan winked at her to let her know it was okay ... and then motioned to her to join him.

She paused. She wanted to so badly ... but this was SO not the type of thing she would ever do. She started to walk closer to him, arguing with herself. Wasn’t he too young for her? Wasn’t he her boss? Wasn’t she the ultimate female power executive who never slept around? By the time these questions crossed her mind though, her feet had taken over next to the naked and gorgeous stud. His hand grabbed hers and pulled her to him. She began to protest and back away, but with his other hand, he raised a finger to his lips.

“Shhhh ... don’t say anything ... never say anything ... its okay, really ... just experience pleasure and move on...” Ryan urged. He pulled her skirt down and her panties quickly as well, and moved her to straddle him. His rock hard cock was aimed straight up at her pussy, and without thinking much more about it, Alison slid herself down onto this incredible fuck pole, triggering an orgasm inside herself almost instantly. She buried her face in his shoulder to stifle a scream.

Ryan reached up to grab her tits through her blouse and bra, and began eagerly thrusting his cock up inside her. She came again in less than a minute, and tears of relief began rolling down her cheeks after she was finished gasping her pleasure from it. Alison may have been nearing 40 years old and all-business most of the time, but Ryan had always found her toned and manicured body very attractive and was more than happy to provide this release for her and enjoy more pleasure for himself. He thrust up into her over and over, as the ship continued its journey around the bay and the party was in full swing on the deck directly above them. Alison came four more times in the next 10 minutes, before Ryan balls emptied yet another load of cum deep inside of her.

 
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