OSL: New York - Cover

OSL: New York

Copyright© 2014 by bluedragon

Chapter 7: Montauk

Erotica Sex Story: Chapter 7: Montauk - A vignette to be read after An Ordinary College Sex Life 3.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Consensual   Spanking   Light Bond   Swinging   Group Sex   Orgy   Oral Sex   Anal Sex   Sex Toys   Cream Pie   Exhibitionism   Double Penetration   Big Breasts   Public Sex  

-- SATURDAY, JUNE 24, 2006 --

I grunted and gripped her tight ass harder, pulling her body against mine despite the viscous resistance surrounding us. Her long, lithe legs scissored behind me, supporting her own weight while she thrashed in our lovemaking.

I grunted again and really began to pound her. Our movements were slow, but powerful and steady. I pushed our bodies forward until her backside was pressed up against the far wall – there was a glass partition there that made a distinct thumping sound each time her ass slammed into it, and the glass reverberated far louder than any concrete wall would have done. That sound, the water sloshing, and my lover's ecstatic moans together filled the cavernous area and echoed around us until we were surrounded by an aria of lustful pleasure.

Her ass banged into the glass with metronomic precision. I'm sure her asscheeks were flattening just slightly for the viewing pleasure of anyone who happened to be on the other side of it, not that I cared to find out. I was too busy reaching my orgasm, and so was she. All at once, she shrieked with a final call of, "I'm cumming! I'm cumming! Oh fuck me and fill me!"

I did just that. My cock felt the internal spasms of her pussy going into overload, an uncoordinated assault of pressure and flowing honey that vibrated against my shaft while I slammed myself to the hilt inside of her and exploded. And my dick spat out burst after burst after burst of creamy goodness as the sticky jism lodged itself against her inner walls.

She thrashed about in the throes of euphoric pleasure, her hair flying into my face and her torso shaking so much that she splashed water everywhere. It was all I could do just to hold on and not lose my footgrip on the swimming pool's floor beneath me. But I dug in with my toes and kept our bodies pinned against the wall while I successfully saturated her spasming snatch with all my spunk. If someone were on the other side of that glass, they would undoubtedly see her asscheeks quivering against the transparent panel.

In the end, the pool's miniature tsunami settled down as the water calmed to an almost flat surface. Adrienne laid her head on my shoulder and sagged against me, tightening her long legs around my waist. With the waterline coming up to our chests, natural buoyancy made her feel light as a feather in my arms, and I held her tenderly while we both panted and gasped to catch our breaths.

"Weren't ... you ... supposed to ... meet Taylor ... like five ... minutes ago?" I wheezed. Fucking in the water was hard work.

"She won't ... mind," Adrienne panted in reply with a sheepish grin. "I really ... needed that ... and besides ... when was the last time ... we ever fucked in a pool?"

I blinked, wracking my brain for such an occasion. I honestly couldn't remember, and I shrugged with a smile. "Well ... there was the hot tub ... in Big Bear..."

Adrienne smirked. "Not a 'pool'. Not exactly..."

In the corner of my eye, I saw a disembodied head seemingly rise from nowhere above the pool deck. The woman's pale white skin stood out in stark contrast to her jet black hair, perfectly framing her obviously Asian features. At first, the floating head looked a little strange, and I frowned as I tried to figure out exactly where she'd come from. But then I remembered there was a hidden staircase recessed into the floor, leading down to the Underground Bar, and the beautiful girl had only ascended the stairs high enough to see us.

"Hey, Mia," Adrienne greeted breezily, still impaled on my prick with her legs wrapped around my waist. "You were down there the whole time?"

"Yes, the whole time," came the response in a clipped Hong Kong British accent. The Chinese girl rose just a little higher until her naked shoulders came into view, interrupted only by the thin string of a halter-top bikini around her neck. Her arms came up, elevating the plush bathrobe she wore as she hitched it up from her elbows and onto her shoulders, and then wrapped the warm fabric around her body. She folded her forearms on the deck and set her chin on them. "It's one of my favorite places in the house, so quiet and peaceful ... Mmm..." Her voice trailed off and her eyes turned a little glassy as she sighed dreamily.

I blushed as Adrienne and I exchanged a glance before turning our attention back to Mia. I thought about saying something, but Mia was still staring off into the distance and had gone so quietly still that I didn't feel like interrupting her little moment. But then a moment turned to two ... and ten ... and Adrienne and I exchanged another glance, wondering whether we should just leave her alone.

But like an animatronic robot suddenly switched 'on', Mia came back to life and fixed us with a silly grin. "At least, it was quiet and peaceful until you two decided to go skinny-dipping."

I blushed. "Sorry."

Mia smirked and shook her head. "Don't apologize. It's not the first time I've watched people make love on the other side of the glass. The view was quiet ... stimulating." Her eyebrows waggled suggestively, and only now did I notice the way her cheeks were flushed as if she were still coming down from her own orgasmic high.

Adrienne grinned and gestured with one hand. "Have you two been introduced?"

Mia shook her head. "I don't believe I've had the pleasure." She ascended the stairs fully and approached the edge of the pool deck, and then squatted with her knees together and off to one side while extending her hand. "Mia Cheng."

"I'm Ben," I replied, shaking her hand and feeling a little awkward at being buck naked with an equally nude Adrienne still mounted on my deflating cock. Then again, my life had been crazy enough lately for me to become a bit jaded to these kinds of situations.

"Mia's the interior designer of this house."

"Really?" Impressed, I smiled broadly. "You did a great job. I've never seen a more beautiful home."

"Well, Jeff Lee deserves most of that credit," Mia replied. "He's the architect who designed the house."

I nodded. "I know. We met on the helicopter ride over."

"He's here?" Mia visibly perked up, a wicked smile crossing her face. "Where is he now?"

"Down by the docks," Adrienne explained. "Taylor has him designing a boat house or something. She went off with him but said she'd be back to talk business with me. I was supposed to meet her a few minutes ago."

"Ah," Mia said with a nod. "So it's a work trip."

Adrienne shrugged and slid herself off my cock, settling her feet down to the bottom of the pool. "Well, work and leisure. We fly home tomorrow morning, but Taylor promised me the business stuff would be done before dinner and after that we would just get to hang out and enjoy ourselves."

Mia swept her arms around the luxurious indoor pool area. "Definitely a good place to enjoy yourself." She added with a twinkle in her eye, "And even I enjoyed your ... enjoyment."

Adrienne glanced at me with a curious look before turning her attention back to Mia. "Speaking of 'enjoyment': Do you know what 'Playroom night' means?"

Mia perked up again. "Say what now?"

"It's something Taylor said to Jeff right after we landed. She told my boyfriend here that he had busy day ahead of him, when as far as I know he's just supposed to hang out and relax. And she told Jeff not to wear himself out."

Mia's eyes sparkled as she suddenly stared at me like a piece of meat. "A Playroom night ... hmm..."

"I take it you know exactly what that means," I surmised knowingly.

Mia hummed and smiled broadly. "Oh, yes. 'Taylor's Playroom' is a part of the house we only finished a few months ago. It's not part of the regular tour, and there are only about a dozen or so who have been in it so far. Kind of a big deal. Most people who visit don't even know it exists but Jeff and I put sooo much work into that place that I'm a little disappointed we haven't gotten to show it off more but I guess I sorta understand why Taylor wants to reserve it for special occasions and I guess THIS is one of those special occasions and oh, I know you're special A.D., but this is Ben's first time and I never really thought he'd ... but oh, now that I think about it it makes TOTAL sense I mean you've been talking and talking about him and ... oh, I'm rambling, aren't I?"

Adrienne and I both grinned. "Sounds intriguing," Adrienne laughed. "And knowing Taylor, I'm guessing it's sex-related?"

Mia's smile turned into a feral grin. "You have NO idea."

I'd seen that look before. The Tri-Delts got that look quite often, a look that said: 'I wanna mount you.' And I suddenly began to wonder if maybe I should have been resting up instead of fucking Adrienne in the pool.

"In any case," Mia began as she stood upright and swept a hand through her hair, pulling her bangs over the top of her head before shaking out the long mane of silky, straight hair. "I'd better get some things taken care of early then. I'll see you later, A.D.?"

"You bet," my girlfriend replied.

"And you..." Mia paused and gave me a sultry look, her eyes momentarily widening as they sparkled with delight. "I'll see you later, too."


While a normal shower only took ten minutes or so, Adrienne and I spent more than twenty trying out all the various functions of the elaborate, high-tech shower area in the locker room adjacent to the indoor swimming pool. It seemed like there were close to fifty heads both on the walls and ceiling, featuring a multitude of options from full-body massage to overhead rainforest torrential downpour. The floor was soft and squishy, and a padded bench in the center looked flat out designed for shower sex. But just when we started to think about testing THAT out, Taylor walked in, fully-dressed, with Charlotte two steps behind her.

"Hey you two. Having fun?" Taylor greeted, out of range of the sprays.

Adrienne giggled and patted my arm. "Boys with lots of buttons to press."

I frowned and mock-glared at my girlfriend, silently flicking some water at her.

Adrienne laughed and addressed Taylor. "So you managed to find us."

Our host shrugged. "Closed-circuit security cameras. None in this room, but I knew you went from the pool into the locker room."

"Ah. Well, we should get dressed," Adrienne replied. "Getting all pruny."

"Computer! Water off!" I ordered into thin air. The speaker system chirped a confirmation, and a moment later all the shower sprays ceased.

"You're a quick study," Taylor complimented with a smile, letting her eyes roam up and down my naked body.

"In more ways than one," Adrienne added with waggled eyebrows.

"We'll see," Taylor promised. "In the meantime, I'm sorry Ben, but I have to steal your girlfriend for a couple of hours."

I nodded. "I'll just hang out and relax."

"Make yourself at home. We've got a media room with more movies and video games than you can imagine. There's a game room with billiards and two bowling lanes. A private gym if you want to work out. Go suntan out on the back patio ... well ... I could go on and on. Charlotte's at your disposal. She'll show you around and give you some options."

"I'll be fine," I replied with a smile.

Taylor smiled as well, and after a quick peck for me, Adrienne left the shower area with her to grab a robe and go do their business. Then, I realized that I still had some soap on me from Adrienne's most recent breasts-as-loofahs exercise, and I turned on the nearest shower spray to wash myself off.

Meanwhile, Charlotte waited patiently and watched me. I caught her smiling at me when I glanced over, and turning my back to her, I rather deliberately clenched my buttocks, causing her to giggle. But I only spent a few more seconds rinsing off before I shut off the water and turned around to find her holding a towel open with both hands.

I stepped into it, but rather than hand it to me, Charlotte began rubbing me down. I silently arched an eyebrow, to which she replied, "Just part of the service."

I chuckled and let her dry me off, rolling my eyes when she paid careful attention to ensuring that my package was completely free of water droplets, albeit with her hands always on the opposite side of the terrycloth. Once I was finished, she followed me into the locker room and let me get dressed on my own.

Figuring turnabout was fair play, I took the opportunity to size her up while she checked me out. Charlotte was a brunette of medium height who wore her hair clipped behind her head and had a pair of stylish eyeglasses perched on her nose. She was dressed with a business-casual sense of professionalism despite it being a Saturday, with a crisp shirt and pencil skirt that modestly covered her body while still revealing her to be in athletically good shape. And although not nearly as showy about her looks as the gorgeous supermodels Taylor and Adrienne, Charlotte was quite pretty with warm eyes, high cheekbones, and a pleasant smile.

But while I didn't mind her ogling me, and though it was fun to engage in light flirting, I didn't expect anything to come of our playful banter. When I finished getting dressed, she was all business as she gestured out of the locker room and asked, "So is there anything in particular you'd like me to show you?"

I thought about that and said, "Well Adrienne gave me a short tour of the house on Wednesday. Honestly, I know my way around and you don't have to babysit me. I can occupy myself until she gets back, and I'm sure there's other work you could be doing."

Charlotte frowned. "I'll leave you alone if that's what you want, but my schedule is clear for the afternoon and Taylor ordered me to ensure that you were attended to. You're our guest."

I shrugged and thought about it. I'd known all along that Taylor would be doing business with Adrienne and I figured I'd have to entertain myself for a bit. Holing up in a media room, no matter how well-stocked, seemed like a waste of opportunity, being in a luxurious mansion like this. If all I wanted to do was play video games or surf the internet, I could have done that at home. "Well, I was wondering what I might be able to do here that I couldn't do at home."

Charlotte thought about that for a moment and suggested, "You could go sailing in the bay, and the weather is excellent for a variety of water sports. We have staff on hand who can guide and accompany you if you don't know how to sail, for example. The golf course, unfortunately, won't be complete until August. But the stables have recently been finished and you could ride a horse around the countryside. It's quite beautiful."

The mention of stables and horses immediately called Dawn to mind, and I realized it had been a long while since I took a horse ride at Morris Camp. Perhaps I'd get a chance to do so again when I visited with my sisters in July. But in the meantime, the opportunity was right here, and it certainly sounded like a fun way to explore the property from a different view.

"A horse ride sounds like fun," I replied. "Let's do that."

Charlotte smiled and glanced down at her pencil skirt. "I am unfortunately not attired for a ride. Perhaps I can take you there and then one of the ranch hands can guide you around better than me?"

I frowned. "You just got done telling me that your schedule was clear and Taylor had ordered you to attend to me, right?"

She blushed prettily. "Then perhaps you can give me a few minutes to change."

"Don't I get to watch you get dressed?" I cracked with a bemused smile, although I prepared to defend myself against an indignant response.

But Charlotte's eyes glittered as she smiled right back at me, and for a moment I found myself reminded of Kim. Still, she shook her head in the negative. "I will meet you at your guest room in ten minutes. I'll also have someone bring you a change of clothes so that yours don't get too dirty."

I shrugged and nodded. "Sure. Lead the way."

Charlotte walked out of the locker room first and led me down the hallway. While the indoor pool and Underground Bar were at the very end of this particular wing, going in the other direction I knew we would pass the private gym on our way back to the central hallway that would take us back to the guest wing. Even though the door to the gym was shut, I could hear the barked orders of a female voice yelling inside.

"Seventeen! Eighteen! Nineteen! Keep going! Don't slow down! Twenty-two! Twenty-three!"

"Sounds like a drill sergeant," I commented.

Charlotte glanced back at me. "Jonathan's regularly scheduled workout," she replied as she passed the glass door and glanced inside. I noticed her eyes pop wide open for a moment, but she continued on down the hall.

I also glanced through the glass door, and my own eyes popped open. But rather than keep going, I couldn't help but stop in my tracks and gawk.

Lying flat on her back across a workout bench was a well-muscled brunette with her long hair braided Lara Croft style and her sports bra pushed above her spherically-rounded fake tits. She grasped a barbell above her head, which was still locked into its rack, and her legs were thrown over the shoulders of one Jonathan Kwong, President and Owner of my new company, as he repeatedly thrust deep into her body.

"Twenty-eight! Twenty-nine! Oh, yes! Fuck! Fuck! Harder! Come on! Pound me! YEEEESSSS!!!!" the brunette screamed. She tightened her legs, tossed her head left and right, and continued counting until she finally got to "Fifty! Alright!"

Jonathan stopped lunging, backed away, and revealed his thick column of manmeat in the air while the brunette rolled off the bench and crawled over to a large, round exercise ball. Folding her arms and bending over it, she spread her legs into an A-frame and wiggled her naked ass back at him. "Fifty more! Let's go!"

Obediently, Jonathan grabbed onto her muscular hips and rammed himself back inside her cunt.

"One! Two! Let's Goooo! Five! Six! Seven!" the brunette barked.

By now, Charlotte had reappeared by my side. "That's Rebecca. She's the personal trainer for everyone in this house. And she knows just how to motivate Jonathan."

I whistled softly, and without turning away from the sex scene before me, I commented, "I need to have personal workouts like that."

Charlotte chuckled. "From what Adrienne tells me, you already do."

Popping my eyebrows, I shrugged and blushed and headed back down the hallway.

You know, she's right...


Precisely ten minutes after leaving me in my guest room, Charlotte returned properly kitted for an equestrian competition, with skinny khaki breeches tucked into riding boots and navy high-collared polo shirt. The only thing missing was a show coat, which would have been too warm for the weather.

I was expecting such attire, as men's versions of the same had been brought to me by Melissa, one of the maids. I'd taken one look at the fancy clothes and initially insisted that I had plenty of jeans and shirts I didn't mind mucking up. But Melissa had pouted prettily and told me I would look rather dashing in the outfit, and somehow I found myself dressed like a riding dork by the time Charlotte arrived.

We took a golf cart from the house out to the stables and parked it right alongside another cart. I followed Charlotte inside the barn, smiling and nodding at the various employees who glanced over at me. But once my eyesight adjusted to the comparatively dim light inside the barn, I found myself surprised to recognize two more figures in proper riding gear already there.

"Hey, had the same idea we did?" Kaitlyn Reynolds greeted buoyantly as she buckled a black riding helmet over her head to complete the equestrian look. The youthful, stacked blonde beauty flashed me a beaming smile that lit up the entire barn.

Charlotte gestured at me. "I gave him plenty of options; he picked horse riding. Said he's done it several times before."

"Really? It'll be my first time," Kaitlyn replied a little nervously. "I'm terrified I'm going to fall right off the horse, but Cassandra's an old pro and she told me it'll be a piece of cake."

We all looked over at the fourth person in riding attire. Jonathan Kwong's assistant Cassandra Cooper was already inside one of the horse stalls, rubbing a dark brown mare's head and speaking softly to her. Unlike Kaitlyn and Charlotte, Cassandra didn't wear a riding helmet and instead wore her golden blonde hair loose and cascading down her back. The horse was already saddled, and after a moment of further horse whispering, the statuesque Australian took hold of the mare's bridle and led it out of the stall.

"Harry is just outside," Cassandra said as she addressed Charlotte, her voice and accent like smooth butter. "I'll take Kaitlyn out to the pen and give her the crash course."

"Do you have to call it a 'crash' course?" the younger blonde complained as Cassandra continued leading the horse out the other end of the barn. Kaitlyn glanced back at me and Charlotte, adding, "I'll see you guys later."

I waved, but Charlotte was already heading through a side door to find 'Harry'. Harry turned out to be a grizzled old cowboy of indeterminate age straight out of Central Casting. He could have been in his seventies, but then he could have been forty with just a few extra weather-beaten lines etched into his face. Whatever his age, he certainly knew his way around the horses as he prepped two docile mares for me and Charlotte before leading them both at the same time out of the barn in the same direction Cassandra and Kaitlyn had gone.

Along the way I found that Charlotte was a bit of a novice herself, having only begun riding after they'd completed these stables on the Montauk property a few weeks ago. While I was no expert, I'd gone riding every summer at Morris Camp from the age of five up until a few years ago. I felt comfortable skipping the helmet, allowing myself to only surrender so far to the dorky equestrian gear, and knew enough about riding to confidently instruct others. So after Harry left us alone, I was more than happy to give Charlotte a few tips on how to sit in the saddle and balance her weight. She was exceptionally good at taking direction.

At the other end of the pen, Kaitlyn had her mare ambling along relatively well, and Harry supervised her while Cassandra returned to the barn to fetch her personal horse. A couple of minutes later, Cassandra led me, Kaitlyn, and Charlotte out of the pen and onto a dusty trail that she said would take us through the woods and right to the boundary of the Kwong estate before looping back along the beach. We'd be back with plenty of time before dinner, and hopefully Jeff, Taylor, and Adrienne would all be done with their respective business by then.

As we headed away from the stables, the path was easily wide enough to accommodate the horses side-by-side, rather than having us go single file. At first, Kaitlyn rode up front with Cassandra while Charlotte stayed next to me. But after about five minutes, it became clear that although it was her first time, Kaitlyn was a natural rider and didn't need much help. On the other hand, Charlotte couldn't quite remain stable in the saddle, even though we weren't moving very fast, and she wound up trading places with Kaitlyn so that Cassandra could help her out.

I certainly didn't mind the switch. While Charlotte was both beautiful and friendly, she had a hard time dropping the guest-host relationship in conversation. This made it difficult for me to make chit-chat, as she was both self-conscious of her riding and anxious to make sure I wasn't unhappy with her level of service or some such nonsense.

Conversely, Kaitlyn seemed more my age and had a bubbly personality that readily lent itself to joking, enjoying the atmosphere, and yes, a bit of flirting. I couldn't help myself. Physically, she was just my type: blonde, busty, and beautiful. But I tried to keep my attention on her bewitching green eyes and not on her bodacious figure. I'd comment on the picturesque scenery, and we'd banter about cool things that caught our attention, whereas Charlotte would've tried to play tour guide in explaining exactly what geographical area of the property we were on.

Kaitlyn and I also got to talk about our significant others. We'd exchanged brief biographies on the helicopter ride, discussing Jeff's architecture background and that Kaitlyn was studying the same major at Columbia. I'd already told her about knowing Adrienne since high school and going to college together before she dropped out to become a model. But this ride was the first opportunity for me to tell Kaitlyn about me and Adrienne growing up on the same street since we were 10, dating in high school, breaking up, getting back together, breaking up again, and getting back together again up through college.

"That's kind of crazy," Kaitlyn laughed. "You've had this epic romance with her, from girl-next-door to all the ups-and-downs of multiple break-ups and now getting your face plastered all over the tabloids because she's a world famous supermodel."

I snorted. "Yeah, no kidding. Certainly the tabloid thing I never imagined ever happening to me while I was growing up."

Kaitlyn gave me a rueful smile. "My own relationship feels so much more ... tame."

"Tame?"

She shrugged. "Jeff and I met less than two years ago, and there honestly hasn't been a whole lot of drama between us since then. We met, we fell in love, and it's kind of been smooth sailing ever since."

"Almost sounds as if you wish things hadn't been so smooth."

Kaitlyn barked a short laugh and shook her head. "Oh, hell no. I like smooth and happy just fine, thank you very much. I can appreciate how unique that kind of relationship is, especially in THIS town. Even John and Taylor: they'd known each other forever, mostly as 'just friends', before they finally settled down and got married. And I know firsthand that there was a lot of angst and heartache in getting there."

"Angst," I sighed. "I definitely know THAT feeling."

Kaitlyn gave me a concerned look. "But you're past that now, right? You and Adrienne? I see the way she looks at you. She adores you, and that's important. It's the way Jeff looks at me, like I'm both the Alpha and Omega of his existence. And as long as you have that, the two of you can get through anything."

I took a deep breath. "I sure hope so. Tell the truth, this latest iteration of me and Adrienne 'together' is only quite recent. She lived here in New York for all of the past school year, and she wasn't around much the year before that, either. The last time we were together as a romantic couple was back when we were college freshmen, before the modeling fame hit. And I'm still trying to wrap my head around how this is going to work with her current career."

Even though our horses were still ambling along the trail, Kaitlyn reached out and rubbed my shoulder. "You'll make it work. I know it."

I gave her a bemused smile. "So sure about a couple you've just barely met?"

She shrugged. "I've known Adrienne for a while now, and even though you and her getting back together is only a recent thing, I know the way she talked about you all the way back to the first day I met her. And I can see in your eyes and hear in your voice how important she is to you. Yeah, I'm pretty sure you'll find a way to make it work."

"Said with the vast wealth of experience of someone who's still in college."

"Well you're just barely out of college yourself, and don't tell me you haven't learned quite a bit from your own experiences."

I rolled my eyes. "Well they say every mistake is an opportunity to learn from it. And if that's true, I've had a LOT of opportunities."

Kaitlyn laughed. "Yeah well me too then – more opportunities than I want to admit. But my life has been so much better for having Jeff in it ... and Taylor ... and John and Cassandra and everyone else. These are special, special people here. I know you and Adrienne are heading back home to San Francisco tomorrow, and the two of you may not come back here all that often, but your lives can only be enriched by having special people like them around, people you can really depend on."

I smiled and nodded. "I know. I have my own group of people like that: people that mean everything to me."

Kaitlyn reached over and rubbed my shoulder again. "Then yes, I'm sure you and Adrienne will make it work. Because having friends like these made me realize that I'm not alone; and if you have those kinds of friends, then neither are you. Friends like that will NEVER let you fail."


In the woods, the four of us had needed to re-order into a single file line, with Cassandra leading and me bringing up the rear. Conversation had been difficult, with most of the commentary being trail-related and intended to keep everyone safe on the paths. But once we hit the beach we were able to spread out into a four-wide group. So everyone could talk together, Cassandra closest to the water off to the left, then Kaitlyn, me, and finally Charlotte on my right.

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