OSL: New York - Cover

OSL: New York

Copyright© 2014 by bluedragon

Chapter 9: Madam

Erotica Sex Story: Chapter 9: Madam - 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  

-- SUNDAY, JUNE 25, 2006 --

I felt something tickle my balls, and with a start, I jerked awake.

"Mmph!" somebody grunted, and as I sat up, I realized I'd just shoved my dick an inch into a girl's throat. She couldn't quite take it, gagging before pulling off my prick and coughing. And my eyelids fought for a bit before successfully breaking through overnight crustiness to open so that I could identify my mystery fellatrix.

Through slightly bleary eyes, I glanced down to find a sweet-looking brunette still coughing over my cock, and I began to apologize. But she beat me to it, coughing once more before raising a hand and saying, "I'm sorry, sir." Pushing her glasses up the bridge of her nose, she promptly inhaled my cock, this time deep-throating me without any trouble.

Consciousness had not yet filled my brain. Certain aspects of my environment were familiar, and yet not immediately recognizable. And though my memory banks were slowly chugging to life, the cascading waves of pleasure rippling from my dick and up through the rest of my body kept overwhelming my mental attempts to get a grip on the situation.

Eventually, I realized that this was really happening and not a dream, that some number of hours had passed since I'd fallen asleep, and that after a restful slumber my body was ready to begin another day. It took me another minute to recognize that I was in the same Kwong mansion guest bedroom I'd shared with Adrienne the night of her birthday party. And only then did I remember that she and I had sort of "adopted" Charlotte for the night.

The lovely brunette had fallen asleep between us, sandwiched on both sides by warm, naked bodies still cooling in the aftermath of our final round of lovemaking. She'd apparently been the first to rise, and had unknowingly initiated the now-standard wake-Ben-up routine. Tenderly patting her cheek, I let her attend to my morning tumescence and glanced to the side for my girlfriend.

Adrienne still slept a couple of feet away, her back to me while cuddling herself around a Cal King pillow. A quick glance at the nightstand clock informed me that it was 10:50am. While we'd slept in a bit, there was no rush to move. There was nothing scheduled for us to do today except fly home, and we still had more than seven hours to get to the airport to do that.

Knowing just how busy and active Adrienne had been last night, I let her sleep in, set my head back down on my pillow, and allowed Charlotte to complete her morning task. A few minutes later, I filled the talented cocksucker's stomach with a fresh batch of protein, patted her on the head, and kissed her in thanks. Then, she asked, "Would you like me to help you get dressed, sir?"

"No thanks, but I'd really like to return the favor," I replied, smiling as I glanced down at her naked pussy.

Taylor's personal assistant blushed and adjusted her glasses. "My apologies, but I have other responsibilities I must attend to."

Arching an eyebrow, I commented, "You have time to help me get dressed but not enough time to let me give you a nice morning orgasm? I could make it fast."

She shook her head. "Duty takes precedence over pleasure," she stated as if it were the most obvious thing in the world. I didn't press her, so after one more kiss goodbye, Charlotte slipped out of bed, gathered her clothes, and left the room.

Adrienne continued to slumber, even snoring just a bit, so I slipped out of bed as well and went through my morning routine. Finding her still out cold when I was done, I scribbled a quick note before silently padding out the door. The aromatic smell of hazelnut coffee led me down the hall and all the way to the kitchen. And I was quite pleased to find Dorothy, the head cook in the mansion, waiting for me with a smile.

Dorothy told me the hot food would be delivered shortly and sent me out to the dining table with a blueberry muffin, some fruit, and a glass of orange juice. I thanked her and left the kitchen, and as I entered the dining room the two people already at the table looked up at me and smiled.

"Good morning, Ben," greeted John Kwong, Owner and President of Jonathan Kwong Enterprises, and my top-level boss. Every now and again it was easy to think of him as "just John", the husband of one of Adrienne's close friends. Winding down from the orgy in the playroom last night, for example, I'd had no problem seeing him as just one of the guys; he wasn't even all that much older than me. But even on a Sunday morning, he was dressed in a neatly-pressed shirt and slacks as he ate his brunch at the dining table, prepared to tackle today's business. And the presence of his equally business-ready assistant Cassandra in the seat beside him only reinforced the "org chart" way of seeing him this morning.

"Good morning, Ben," Cassandra chimed in with that wonderful Aussie accent.

So I replied politely, "Good morning, Mr. Kwong, Miss Cooper."

'Mr. Kwong' had been holding a copy of the Wall Street Journal in one hand as he read, but with a bemused sigh he set both the newspaper and his fork down on the table and gave me a look. "Away from the office, I'm just 'John'," he reminded me.

I grinned and shrugged, apologizing, "It's gonna take me a while to get used to that."

He waved me off and shared a smile with Cassandra before gesturing to the table. "Please, pull up a chair and relax. Believe me, you should be saving up your energy instead of wasting it worrying about office protocols when we're more than a hundred miles away from the office."

"Saving energy?" I queried while sitting down and placing my plate in front of me.

John smirked as he sat back in his chair and deliberately looked me up and down. "You don't look like a worn-out rag, squeezed of every last drop before being hung out to dry. Clearly, Taylor hasn't gotten to you yet, which means that your great ordeal is still yet to come. My wife can have a voracious sexual appetite, especially when she's been made to wait an extra unexpected day."

I blushed and risked a glance at Cassandra, reading her face for any reaction. While I assumed John's personal assistant would be quite aware of her boss' activities, and she'd been present when I'd asked about the Playroom during our horse ride, Cassandra's lack of participation in last night's events left me unsure of exactly how much she knew. It wasn't every day that I met a couple with the kind of open relationship that John and Taylor apparently had, and my not fully understanding its dynamics made me unsure of how to act in this situation. I bought myself a little extra time by nodding slowly and taking a bite of my muffin. But after chewing and swallowing my bite, the best response I could come up with was, "Maybe I should have Dorothy bring me a little extra food."

"Maybe you should," he commented while sharing another knowing smile with Cassandra. He then returned his attention to his newspaper, and Cassandra went back to fiddling with her Blackberry while also spooning up a bite of yogurt.

I tried to focus on my food, but my lack of understanding still bugged me. Here John and Cassandra sat, going about their daily routine of reviewing business on a Sunday morning, immediately after joking around with me about my upcoming sexual liaison with the boss' wife. The whole situation was just ... weird. I couldn't entirely wrap my head around it. For one thing, I'd gone to great lengths over the last couple of years to work at NOT getting involved with "taken" women, figuring it was best not to meddle with someone else's relationship. And I knew from past experience that if I'd been in John's shoes, I wouldn't have been so nonchalant about my wife hooking up with some guy I barely knew.

I mulled these thoughts while finishing my muffin and some of the fruit. Dorothy came out of the kitchen to bring me an omelet and two slices of french toast. But I only ate a couple of bites of each before I set down my fork, looked across the table, and asked, "Can I ask you a really personal question?"

Both John and Cassandra looked up at me. In the intervening time they'd chatted a bit about work while continuing their meals, but I'd caught them during a lull, and when he realized I was looking right at him, John replied, "Sure."

Furrowing my eyebrows, I took a deep breath and gave him a straight look. "How is it that you're okay with me potentially sleeping with your wife?"

John's eyebrows rose and he gave me a bemused smile. "You worried I'm gonna fire you or something?"

I sat up straight and shook my head. "No, no. This has nothing to do with my job. It's just ... I'm not a sexual novice by any means, as you've probably heard by now. But I have been going out of my way to avoid encounters with other men's women."

"Like the way you avoided Kaitlyn last night?" he asked with a touch of sarcasm and a smirk.

Again I glanced over at Cassandra, gauging her to see how much she already knew of last night's events. But while she appeared intrigued, she didn't seem surprised by anything we were discussing.

"Actually, I did avoid her at first," I finally replied. "We had to stop and talk about the situation for me to wrap my head around it before we actually did anything. And even so, I don't think I could have gone through with it if Jeff had been in the room with us."

"Worried about how Kaitlyn's boyfriend might react?"

"Sure. I ... uh ... Well let's just say I haven't had the best experiences when other guys found out I'd hooked up with their girlfriend. Plain and simple, you and Jeff are the first guys I've ever known who would be perfectly okay with me sleeping with their women, so I've never really had the chance to ask this of any other guys before. Truth be told, I don't have many male friends, period."

"Really? The way Adrienne describes your lifestyle I would have thought you'd have a bunch of guys making nice just to be in orbit of all the girls that surround you."

I shrugged. "Never really worked out that way. Most of the guys I ever talked to were always worried about me stealing 'their' girls away."

"Well please let me reassure you that I'm not worried about that in the slightest."

I looked around the palatial mansion and weighed what John had to offer Taylor versus what I had to offer, and I chuckled. "I'm sure."

John shrugged. "So you understand how I can be okay with her wanting to, put plainly, 'fuck your brains out'."

I blinked and furrowed my eyebrows. "Actually ... not so much. I mean, I understand why she wants to 'fuck my brains out'. I've developed this reputation, a reputation Adrienne apparently has made bicoastal, and it's led more than one woman my way looking for their own 'Big Ben Experience'. I understand that women can be just as sexual as men, that they feel lust and desire and sometimes just want a spectacular orgasm with no emotional strings attached. I get why Taylor wants this to happen, but ... I'm still..."

" ... still trying to understand with how I'm okay with you sleeping with my wife."

John and Cassandra shared a look as they communicated something with just their eyes. I recognized the special bond the two had, some form of mental intimacy that was no doubt the result of the inordinate amount of time the two must spend together. I started to wonder, knowing the openness of John's and Taylor's relationship, if Cassandra were also sleeping with him. It seemed likely, but then again, she hadn't participated in last night's events.

"Well you've already worked out that I'm not worried about you stealing Taylor away from me," John began thoughtfully, his stare a little vacant as he processed. "And I think you know that Taylor loves me. The most obvious answers to your question are right there ... so ... really ... this isn't a question about how I'm okay with you sleeping with my wife. It's more that you wouldn't be okay with another man sleeping with your wife. Am I right?"

I sat up straight and popped my eyebrows. Glancing over, I caught Cassandra giving me a knowing grin. I gathered that she'd figured the same out already.

"Well..." I began slowly, working that idea around in my head. "I can't say I disagree. I've been in a similar situation before. I knew my ex-girlfriend loved me beyond all measure. I had absolutely no worries about some other guy stealing her. But I also knew she had her own cravings and desires and I did my best to fulfill those needs. After all, she let me sleep around with other girls and I thought it only fair that--"

"Stop right there," John interrupted. "'Fairness' has nothing to do with it."

I frowned. "Excuse me?"

John shook his head. "Trying to balance what's 'fair' in a relationship is the first step in undermining it. A relationship isn't about 'fair'."

"I know, I know. My girlfriend reminds me of that all the time, that our relationship shouldn't be about being 'fair' but rather about understanding what we each need. Trying to balance what's fair is emotional accounting."

"You have a very smart girlfriend," Cassandra said, joining the conversation for the first time. Her eyes narrowed slightly. "But you did just say 'my girlfriend', not 'Adrienne'. It's not like we don't know her name."

I blushed and averted my eyes for a moment, but only for a moment. Adrienne and I had already discussed how to handle these situations: Don't go out of our way to advertise that I was also dating Sasha, but don't hide it if asked directly either. So I readily admitted, "My other girlfriend, Sasha. She's back home in San Francisco."

Cassandra smiled triumphantly and sat back in her chair.

"I get that trying to do what's 'fair' isn't the right approach," I continued. "Like I said, this was with my EX-girlfriend and ... well ... that's done with right now."

"But it still comes back to you not being fully comfortable with the idea of your current girlfriend... girlfriends ... sleeping with other guys," John stated. "Is that why Adrienne told us she was off-limits? Because you wouldn't be okay with it?"

"No, no. She insists that being faithful to me is entirely her choice."

Cassandra frowned and leaned forward again. "You used the term 'faithful', thus implying that were she to have sex with another man she would therefore be UN-faithful?"

I shrugged. "I suppose."

"So you view Taylor having sex with Jeff, or with you, as being 'unfaithful' to Jonathan?" she added.

I blinked. "Well ... if you're trying to parse the word."

"Not parse the word, but parse the meaning as it is in your head," Cassandra clarified. "Do you see Taylor having sex with other men as being a betrayal?"

"Not when John is perfectly okay with it." I arched an eyebrow and turned my attention back to the man in question. "Are you?"

"Absolutely." John smiled at me. "But again we come back to the main point: You wouldn't be okay with it. You would see it as a betrayal."

I sighed. "Is that so wrong of me? I mean, I'm aware that it's totally hypocritical. I certainly want to – and do – have sex with many other women who are not my girlfriends."

John shrugged. "Not wrong, just honest."

"But how do you handle it?"

"Because I handle it."

"But how?"

"Does it really matter?"

"Yes!"

John pressed his hands together and gestured with them as if asking me for patience. He waited an extra beat and gave me a sincere, but serious, look. "Do you think that you should be okay with your girlfriends having sex with other men?"

I frowned, scrutinized his question for some hidden meaning, and replied cautiously, "Yes..."

John's stared at me a little harder. "Why?"

"Because that's only..." I trailed off, realizing where my train of thought had gone, and stopped myself before saying the word 'fair'.

John's eyebrows went up, an expectant look on his face. Cassandra smiled again and said patiently, but a little condescendingly, "I thought you were past trying to do what's fair."

I sighed. "I can't help it."

"Because you feel guilty," John explained.

"Yes."

"Guilty over your supposed hypocrisy."

"Yes."

"Out of fairness, if you get to have sex with all these different women, then it's only right that your girlfriends be allowed the same freedoms since they have lustful urges and desire pleasure and variety as well."

I sighed again. "Yes."

"So let's say you allow your guilt to rule your decision-making. Seeking to assuage that guilt, you force yourself to grant permission to your girlfriends to take other male lovers. But instead of resolving your hypocritical guilt, you create resentment that your girlfriends allowed some other man's filthy penis into their temples of faithful purity to you."

I groaned and slouched a bit in my chair.

John and Cassandra shared a look and a chuckle. John reasoned sagely, "You can't balance your supposed 'wrongs' by allowing your girlfriends to do something equally 'wrong'."

"I know, I know."

"Do you?"

"I do. A solid relationship is based on giving and being accepting of your partner, but not at the expense of each other. You can't make up for hurting them by allowing them to hurt you."

"Right," John agreed.

"But that doesn't mean I won't feel guilty over what feels like an imbalance of expectations. My girlfriends know I'm going to end up sleeping with other women. They don't expect monogamy from me, and half the time it feels like they're the ones pushing me to nail these different girls. Those are their expectations. On the other hand, I expect them to only have male-sex with me. And should they ever fail to meet that expectation..."

"You would feel betrayed."

I nodded slowly.

"It's okay to feel that way."

"But you don't."

"I would, under certain circumstances. You talk about expectations. Sure, I expect Taylor to enjoy the company of other men, but not just any man. If she were to screw around behind my back, if she were to have sex with someone against my express permission, then I would feel betrayed just the same."

I shook my head. "But I don't want my girlfriends to have sex with ANY other man, period. There's not a single guy I can think of who I'd be okay with fucking Adrienne or Sasha ... The thought ... I ... I just can't handle it."

"Again, it's okay to feel that way."

I sighed again, took a deep breath, and asked once more, "How do you handle it?"

"You're not me, Ben."

"I know I'm not. Billionaire..." I gestured upward at the vaulted ceilings for a bit before touching my own chest. " ... me."

"Money has nothing to do with it. If anything, most rich guys I know want to – and expect to – fuck everything that moves, but can't stand the thought of someone else laying a finger on 'their toys'." John shook his head.

I chuckled at that.

He leaned forward, putting his elbows on the table while giving me that sincere, serious look again. "You and I are not so very different, at least when it comes to these complicated relationships. It certainly can be hard striking the right balance between permissiveness and expectations." He gave Cassandra a significant look, and something passed between them nonverbally.

I nodded in agreement.

"You and I both have multiple women in our lives, women who love us and yet are willing to share us. Ignore the money thing for a minute and focus on that."

"Okay."

"The key in that last bit is that our women are willing to share us. They're okay with you banging other women. And if they're okay with it, why the hell do you feel guilty?"

"Because..." I trailed off before letting myself say another word in the direction of 'fairness'.

John fixed me with a serious look. "You don't have to feel guilty for the good things you have in life. I've been far more fortunate than most, and the source of all the wealth you see around you is the result of dumb luck more than anything -I- did to deserve this. I happened to be born to a wealthy man I never met who left me just about everything when he died. Yay me. I watch the news about starving children in Africa and see the homeless on the streets of New York. I want to help them, and I do in my own ways. But the important thing is that I don't try to help people out of guilt. If I only felt guilt then no amount of aid or charity short of giving away everything could ever fulfill it. I've had to learn to accept my good fortune and realize that I have to live my own life without being beholden to anyone except for the people I care about."

John got a moist look in his eyes and he turned to slide a hand on top of Cassandra's. She smiled back at him and put her other hand on top of his. Any doubts I'd harbored about their level of intimacy were washed away.

Looking back at me, John said, "A man's duty is first and foremost to his family, whether blood-related or not. I've chosen to take advantage of my good fortune to better the lives of those most precious to me, as I think everyone should. Some only have the means to take care of their families and don't have much left to share outside of it; I happen to have a little extra, and so I do go out of my way to help make the world at large a better place. But in the end that global view still comes back to improving the world for my family and for my future generations."

I smirked. "Self-interest."

John weighed that for a moment before smiling. "I suppose you could say that."

I simply grinned.

John raised his eyebrows. "You want to know how I can be okay with you sleeping with my wife? I'll tell you straight up that it has nothing to do with me trying to balance what's fair against my sense of guilt."

"But instead it's entirely about wanting Taylor to be happy," I stated with some modicum of understanding as I nodded slowly. "Your wife can have a voracious sexual appetite, you said. And I suppose your life is better if she can satiate those needs with someone else ... lest YOU spend every waking moment as that worn-out rag squeezed of every last drop before being hung out to dry."

Both John and Cassandra grinned at me. "I think he's got it," Cassandra said in that alluring Aussie accent.

"I wouldn't say I've GOT it," I muttered before taking a deep breath. After exhaling slowly, I gave them both a thankful look and added, "But it's a start."


The conversation continued to flow once we changed topics, and my breakfast wound up going cold. When John and Cassandra got up to leave, Dorothy returned to us and offered to cook me up a fresh omelet. But I couldn't bring myself to let my food go to waste, so I declined the offer and spent the next few minutes polishing off my plate.

My note had suggested that Adrienne join me for breakfast, and when she didn't arrive I assumed that she was still asleep. But when I returned to our guest room, I found it empty. And after a cursory look around, I found that she'd written a note for me. It read:

Taylor invited me to get brunch with her upstairs on the balcony. Come join us in the Master Suite and maybe I'll find you something new to eat.

She'd signed the note with a smiley face and her familiar stylized "A".

With a smile, I left the guest room and headed for the "hidden" back stairs. There was an unmarked door at the end of the guest wing, decorated to appear as just another part of the wall, that could be locked during social events. Adrienne had pointed it out to me as a private way to get from the guest wing up onto the second floor. Knowing what I knew now about the Kwongs' lifestyle, it made sense for John and Taylor to have convenient access to visit their friends and play partners. Feeling just a bit naughty by my use of the "secret passage", I found myself padding quietly up the treads and moved so stealthily that I accidentally surprised a maid with a cleaning cart backing out of one of the upstairs bedrooms.

I quickly apologized for my sudden appearance behind her, and realizing that I didn't actually know where the Master Suite was, I took the opportunity to ask.

"Down this hall and to the left," the pretty maid explained politely, gesturing with one hand. "It has its own marble foyer. Can't miss it."

I thanked her and walked down the hall. Sure enough, the Master Suite had a grand entrance of its own. But when I knocked at the door, nobody answered. Adrienne had said that she and Taylor would be on the balcony, so I went ahead and let myself in. I glanced around the empty sitting area and marveled at the sheer size of the television screen there. A doorway led to the Master bedroom, but the sitting area itself had patio doors that led directly out onto the balcony, so I headed for those.

From the entryway, I hadn't been able to see the two ladies outside on the balcony, but as I approached the patio doors I got a better angle and stopped dead in my tracks. Taylor and Adrienne were indeed out on the balcony, but they no longer sat at the table where their half-finished breakfasts remained. Instead, Adrienne leaned back against the railing with the open ocean and clear blue skies as a backdrop. And Taylor stood pressed up against her, cradling my girlfriend's head with her left hand while the two shared a tender, passionate kiss.

My hand had frozen just before grasping the door handle, and I let it fall away while I leaned to the side to get a better view through the glass. The Sapphic liplock built and built, with Adrienne's fingers gliding up Taylor's back before sliding into the raven-haired beauty's short locks. Finally, they broke for air, with my girlfriend letting her head fall back as she gasped for oxygen. And Taylor took the opportunity to kiss her way down Adrienne's graceful neck and tug aside Adrienne's shirt to expose her shoulder.

My girlfriend had dressed comfortably, donning a sexy pair of buttercream satin pajamas that left a wide expanse of her cleavage exposed, and even more skin came into view as Taylor slipped the shoulder strap down Adrienne's arm. The dark-haired goddess raised her hands to unfasten Adrienne's shirt buttons while bending over and continuing the butterfly kisses down my girlfriend's chest, until a rosy nipple briefly came into view before she surrounded it with her lips.

Adrienne moaned and clutched Taylor's head to her bosom, her body sagging against the railing while she felt her friend's mouth and tongue go to work. Shortly after, Taylor switched breasts and also slid a hand into Adrienne's pants, and even though I hadn't so much as touched myself I could feel my cock trying its best to bust through my shorts.

My girlfriend let John's wife fingerbang her almost to the point of orgasm, but not quite. Before she got there, she pushed the older woman away and backed her up until Taylor slid her tight ass onto the table. Then it was Adrienne's turn to slowly undress Taylor, starting with the buttons on the older model's magenta satin shirt. Once she had an unbroken line of creamy white skin exposed from throat to waist, Adrienne seized a strawberry off a nearby plate and trailed it delicately across Taylor's lips, between her breasts, and down into Taylor's pajama shorts.

Though the strawberry was hidden from view, I could tell the moment it entered Taylor's pussy from the way she shivered. Adrienne grinned wickedly, her hand forming a bulge inside the front of Taylor's shorts that pumped in and out rather suggestively. After a few seconds, Adrienne pulled the strawberry out and rather lasciviously swirled her tongue all around it before biting the majority of the fruit off the stem. Taylor abruptly got back to her feet, her hands seizing Adrienne's head as she shoved her tongue into my girlfriend's mouth. And I had to fight every urge in my body to rush out the door and join them.

It was a good thing I resisted, because otherwise I would have interrupted what came next. Kisses and fondling and fingerbanging weren't going to cut it anymore, for either of them, and Taylor grabbed Adrienne's hand to lead her away from me and out of view. Only now did I follow, opening the patio door in front of me and stepping out onto the balcony. But as I skulked after them, I realized the ladies had used another set of patio doors to enter the Master Bedroom. And I arrived just in time to see Adrienne yank Taylor's shorts down to mid-thigh and hoist the older woman up and onto the massive four-poster canopy bed.

They'd left the doors open behind them, so for the first time I could hear as well as see the action before me. With a cocky grin, Adrienne gave Taylor a playful shove in the chest that made the dark-haired beauty laugh as she fell back. As Taylor's legs came up to counter her fall, Adrienne snagged the shorts and yanked them completely off her lover's legs. And my girlfriend wasted no time before diving face-down into Taylor's crotch.

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