Big Brother Boss Ch. 02

That same night, Riley found herself at the foot of her bed, wearing nothing but the lacy red bra she had on that day and a pair of matching panties, with her husband sitting on the bed in front of her, totally naked, cock erect and eager for the lewd attention it had been promised.

Riley intended to make good on that promise. It was a tradition the two of them had: whenever Riley was promoted to fuck some new boss, she would give Dave exactly what the boss had gotten, while she regaled him with the details of her new office lover. Given how long she had worked for Henry Abbot previously, the two of them hadn't gotten a chance to revisit this tradition in some time.

Riley didn't titty fuck her husband often, but when she did, he enjoyed having her keep her bra on while she did it.

"You know, HE had me take this off first." she smirked at her husband.

"Oh I'm sure he did, but I prefer the visual" Dave winked.

"Well, you know what they say: the customer is always right!"

Riley began by wrapping her lips over the head of his cock and sucking it like a lollipop, not once taking her eyes off her husband.

"Ohhhh yeah". Dave briefly closed his eyes as he moaned, adjusting the onslaught of pleasure his wife's skilled mouth was providing, before opening up to make eye contact with her again, grinning from ear to ear. Dave ran his hands through he golden hair, but spoke not another word, except for the moaning and groaning sounds that occasionally escaped him.

Once Riley was satisfied that the tip of Dave's cock was well and sucked, she began to work her way down his shaft, a half inch at a time with each slow, lascivious stroke. Each time her mouth ascended his pole, she worked her tongue around his cock, causing him to gasp and involuntarily thrust into his wife's mouth. Riley loved the feeling of having full control over his sexual response. She especially loved that she could exert that control with just half his cock in her mouth.

Riley's hands massaged the base of Dave's cock as she finally took the last of his shaft to the back of her mouth. Most days, this would be as far as she would go, but tonight, Riley looked up at her husband, mouth full of cock, and winked at him, removing her grasp on his shaft as she plunged forward to take the rest of his length in her mouth like a pro. After the practice she'd had that morning with Levi, it was almost effortless.

"Oh FUCK, baby! That's so good!"

"Mmhmm!" Riley murmured her acknowledgment around the base of Dave's cock, causing him to moan and attempt to thrust his cock even deeper into her supple throat. Riley reached out and grabbed both of Dave's hands and placed them on the back of her head, urging him to push her deeper. Her husband didn't hesitate.

"OH SHIT. FUUCK! YES BABY! I fucking love it! Swallow that cock!!"

Dave humped a full 7 inches of dick down his wife's throat, completely lost in ecstasy. Normally, Riley would have started gagging by now, pulled away, or give some indication for him to stop, but not this time. She simply moaned in delight as he continued his onslaught.

"Holy shit baby, you're so fucking good at this! UHNG! Don't stop! FUUUUCK!"

Riley was lost in a trance, transported mentally to that morning when she performed this very act on her much larger boss. For a time, her mind was completely blank, focused only on how to give her husband as much pleasure as possible. She bet she could deepthroat him until he unloaded inside her mouth. As fun as that sounded, she had other plans for him. Dave released his hands from his wife's head as she slowly withdrew her mouth from his cock, sucking forcefully as though she didn't want to let him go.

"OH! FUCK! Uhhhhng!" Dave thrust forward as if to keep his cock inside Riley's mouth as long as possible, but he eventually popped out. He took a second to catch his breath

"Wow...Uh, do I have your boss to thank for that blowjob?"

Riley pretended to be offended "I'd say you have your wife to thank for that blowjob!". Dave raised an eyebrow and Riley rolled her eyes "Well...you don't not have my boss to thank for it—and for this..." Riley shot Dave a sultry smile as she directed his cock underneath her bosom, which was pushed tightly together by the push-up bra she was wearing, creating an irresistible and incredibly fuckable valley for her husband's cock. She slipped the head of his cock underneath her bra and let go, letting the bra do the work of squeezing her generous, pillowly breasts around her husband's cock as she descended onto it.

"Ahhhhh. Yeahhhhh!" Riley's tits were so soft, so encompassing, that Dave could just put his head back and get lost in the pleasure.

Riley moved her hand to play with her husband's balls as she rose and sank at a tantalizing speed. "Is this how you like it, baby?"

"Yessssss..."

Riley giggled and simply enjoyed the act of making her husband happy. She enthralled him with a verse of moans and coos that she knew would encourage and delight him. Occasionally, she would feel his cock throb against her breasts, which released tiny shivers of pleasure in her own body. Her eyes were closed, her lips were pursed, everything was as it should be. For a time, the thought of the acts she performed for Levi Cochran that day, the things she said to him, melted away.

Dave placed his ravenous hands around Riley's tits and squeezed gently, sighing as he did, taking in the magnificent view. He reached around and unbuckled her bra strap, letting it drop to the floor. Riley giggled as her husband palmed her magnificent breasts, squeezing them insistently around his straining cock, thrusting slightly. They felt so fucking good. Dave was always more of an ass man himself, but that didn't stop him from properly appreciating a perfect pair of tits when he saw one, and his wife had one. Luckily for him, her ass was also out of this world, and he had made up his mind that he was going to treat himself to it as well.

Dave thought, as he often did, about how many other men had the good fortune to be in his position; how many other men had grabbed, sucked, and fucked his wife's tits. Though it might shame or enrage other men, it turned him on immensely to think about how much his wife got around. Neither of them could control the situation anyway, so why not make the most of it?

"So you did this for this Cochran guy today, did you?" Dave asked.

"Mmhm" Riley affirmed

"Did he squeeze your tits just like this?"

"Yes, baby."

"Mmf. Is he handsome?"

"Not as handsome as you, baby" -- this wasn't a lie per se. Dave was almost 20 years younger than Levi, a stud in his own right, and more conventionally attractive than Levi. That said, Levi had a certain confident, mature allure that Riley couldn't deny. For his age, he was an incredibly handsome man.

"Is he big?"

"Mhmmm. He's just about as big as you." Riley had prepared this lie already. She couldn't bring herself to tell her husband about the towering cock she had just been fucked by, and he didn't need to know.

"Is he good?"

Riley cocked her head as if to think, "Better than Abbot!"

"Better than me?" Dave raised his eyebrows.

Riley smiled wryly "Now, if I said 'no' would you believe me?"

"Not so much anymore!" Dave exclaimed, half laughing.

"Well then I guess you're just going to have to try and top him, stud!"

"Alright! You asked for it!"

Riley shrieked with laughter as Dave grabbed her and got behind her, pushing her onto the bed. She fell face forward onto the mattress with her feet still on the ground, and her juicy, heart-shaped ass sticking right out toward her husband's crotch. He grabbed her hip with one hand and smacked her ass with the other. Riley let out a sharp squeal as her husband promptly positioned his rock hard cock against the panty-clad folds of her sex. With one hand he squeezed her ass, while he used the other to run his cock up and down across her perfect cameltoe.

"Oh fuck you're so damn hot..." Dave moaned

"Fuck your hot wife and her hot, tight pussy, baby!"

Dave groaned as he slid Riley's panties over her ass and down her legs, her perfect glistening moistness revealed to him. He wasted no time in plunging into her familiar wetness.

"AHHH god damn, that's good!" Dave smiled contentedly

"OHHH FUCK! Yeah baby! Fuck me!"

"UGH! FUCK! FUCK! YES!" Dave slammed rhythmically into his bombshell wife, fucking with all the confidence of a man who had nutted earlier that morning, and knew he had the stamina for it.

Riley was quickly engulfed in the flames of passion, feeling the delicious stretching, aching, filling sensation of her husband between her legs. She was relieved to find that Dave's cock felt as good inside her as it ever did. Earlier that afternoon, she had wondered and worried about what sort of impact the unrivaled fucking she had received earlier would have on her body, but there wasn't any noticeable difference. He still felt plenty big for her. She smiled and glanced back

"That's it, baby! Give it to me hard and rough!" Riley cooed, "Pound your wife's sweet pussy!"

"Ahhh yes! YES! FUCK!" Dave did exactly as instructed, humping and thrusting with reckless abandon. He slid his hand down between Riley's legs and began to massage her clit. She instantly gasped and a shiver of pleasure ran up her body, a ripple that Dave could feel in her snug little cunt. He looked down to see his wife's perfect bubble butt, his pride and joy, slamming and jiggling against his hips, adding immensely to his pleasure. He groaned and tried to hold his own impending orgasm as bay while triggering his wife's.

"OHHHH THAT'S SO GOOD! Don't stop, baby! Make your girl cum!! AHH!" Riley gasped again as her eyes lidded shut from the pleasure. Dave was incredibly skilled with his fingers, and after years of sex together, he knew exactly how to drive her wild with them while fucking her. "OH! OH! OH! YESSSSS! I'M GONNA CUM, BABY! I'M GONNA CUM ON YOUR BIG FUCKING DICK!"

The rhythmic coupling of Dave's hips and Riley's perfect, succulent ass sent unbelievable bursts of pleasure shooting through Dave's cock and up into his groin. He felt the familiar sensation of a growing tightness in his balls which each thrust. He knew his wife was close. He let himself go to enjoy the tantalizing softness of her silky folds around his cock, the way his balls slapped against her pussy each time he slammed forward, the exquisite sexual pressure caused by her ass pressing tightly against his groin. It was more than any man would be able to bear.

"Fuck honey! I'm gonna cum! I'm gonna fucking explode inside of you! Milk my cock! YES!"

"YES BABY! Cum for me! Nut in my naughty little pussy! Make me cum on your big fucking dick while you fill me!"

Riley's lewd language tipped Dave over the edge, and now his body felt as though he was plunging off a cliff, free-falling towards ultimate sexual gratification "I'm cumming! I'm cumming! Oh my god, I love my hot, slut wife!"

"OH! UNG! I'M CUMMING WITH YOU BABY! I FUCKING LOVE MAKING MEN CUM!"

This was the last straw for both of them. Powerful orgasms ripped through both of the lovers as they descended into a cacophony of gasps, moans, and cries of passion that even the neighbors could hear and recognize. Neither of them cared. They were completely lost to pleasure and married bliss. Dave's ground his feet into the floor to completely slam his hips as deep as he could go into his gorgeous wife, and held firm while he pumped jet after jet of his cream into her welcoming pussy, feeling the unrivaled sensation of relief and satisfaction wash over him as his wife writhed in orgasmic bliss beneath his strong, toned body.

Riley's own orgasm cascaded in a symphony of pleasure. Knowing this was the fourth load she had received in her pussy today, from three different men, drove her absolutely wild with sinful lust. She humped her own hips back hard against her husband's, instinctively attempting to milk as much from his cock as possible, while her own body rewarded her generously for her promiscuity. She trembled and mewled as her husband staked out his territory and reclaimed her body as his own.

As Dave's orgasm subsided, Riley felt him gradually backing off, releasing the pressure on her ass. Gradually his cock softened, and the both of them began to catch their breaths. Dave slid out from Riley and fell backward onto the bed next to her, still breathing deeply, as the two lovers allowed the hard earned afterglow to wash over them. Dave spoke up first:

"Better than your boss?"

"Much better", she lied.

In bed that night, while her husband lay fast asleep besides her, Riley couldn't help but think about Levi Cochran—the things he did, the things he made he do, the things she voluntarily did and said. She felt ashamed, embarrassed, nervous, and incredibly aroused. Despite the amount of sex she had that day, she began to fantasize about what the next day with her boss might bring. She couldn't help herself. With every other boss she'd had, she played the role of the dutiful slut, pretended to be everything her bosses wanted her to be, acted the way she knew they wanted her to act. She often enjoyed having sex with these other men, and she wasn't ashamed of that, but she was someone else before, during, and after the act. With Levi, there was no acting—she didn't have to play the part of the eager whore, she just became one. Her reactions were every bit as real as those her husband elicited from her.

Riley attempted to rationalize what had happened that day with Levi; yes, he was obviously well endowed, more so than any other guy she had been with, but he was also something new. She knew that the first time having sex with a new man was always the most exciting, the most physically stimulating time. She allowed herself to believe that the thrill of fucking Levi would wear off sooner rather than later, that she could once again tell herself he enjoyed sex with her husband more than sex with Levi, but she couldn't say that now. The truth was that Levi Cochran fucked her better than any man ever had, and that what her body yearned for now, more than anything, was to be fucked by him again.

***

The next morning, Riley entered Mr Cochran's office at 9:40 am to find him impeccably dressed, as if expecting special company. Riley appreciated his sophisticated sense of style and impeccable grooming habits. It was clear that his self-presentation, as well as his charisma, played a big part of his rise to the top of the corporate ladder.

"Ah Mrs Williams, come in. Thank you for being on time."

"Of course, sir!"

Levi walked over to Riley as he looked her up and down. She was wearing a short, form fitting black dress, stockings that came almost to the top, and a pair of high, black heels. It was a welcome departure from her more casual, yet still very sexy, attire from the day before. Levi smiled and extended his hand to take hers. She coyly accepted his offer, and he led her by the hand over to his desk.

"That's a gorgeous outfit you've chosen today, Mrs Williams. You'll look incredible in it bent over my desk."

Riley smirked. Straight to business.

Once Levi had her in front of his desk, he wrapped his arms around her hips, caressing her perfect curves and the silky fabric accentuating then so well. Gently, yet insistently, he pushed her back forward, bending her over his desk as promised, while keeping a tight grip on her hips, which he ground into his crotch. Riley could tell that he was already partially erect—it was hard to miss. Levi slid his hands down below her waist and stroked her smooth, flawless thighs, then teasingly rolled the snug hem of her dress upwards. It was short enough that it didn't take much effort to reveal her delectable ass underneath. As before, Levi found no underwear underneath, only the naked folds of her sex.

Riley had a perfect view of the San Francisco skyline as her boss pawed at her exposed butt. She smiled. She knew exactly the power that her ass had over men, and she milked it for all its worth, swaying and thrusting her hips at him. It wouldn't be long until he was balls deep inside of her.

If only she knew which hole he'd be balls deep inside...

Riley heard Levi's pants unzip and drop to the floor. Levi, now at full mast, rested his impressive cock between her cheeks and ground into them greedily, moaning as he did. Levi sharply slapped her ass and squeezed roughly, soaking in the way it felt against his skin. After a minute or so of this, Levi stopped, and Riley heard him opening a drawer in his desk. She looked over her shoulder to see him take something out, but couldn't see what it was.

"What is that?" Riley asked.

"It's lube, sweetheart. You'll need it"

Realization dawned on Riley, and she turned around, bewildered, "Wait, you want to put that in my ass??"

"But of course," Levi replied slyly. "After all, I still have one more hole to sample."

"But...there's no way you're going to get that to fit!"

"Oh I fully intend to make it fit, Mrs Williams. All of it. And it shouldn't be a problem for you, your husband fucks you in the ass, doesn't he?"

"Well yes, on occasion, but--"

"And after all," Levi continued "I'm just about as big as him!"

Riley paused-- what was he talking about? He was considerably bigger than her husband and he knew it. Was this some sort of joke? If it was, she didn't understand it. Riley watched Levi squeeze the lube from the bottle into his hand and begin to stroke his 10 inch cock with it, working it over his full length. His thick, veiny cock glistened from the wetness, and Riley felt herself getting wet in spite of herself. Satisfied, Levi stepped closer and approached Riley, cock in hand, and she felt his enormous mushroom head press against her tiny asshole. In that moment, something dawned on her

"Wait...were you...listening to my conversation with Dave last night?"

Levi grinned "What else did you think that implant yesterday was for?"

"But that's—OH!" Riley's protestations were interrupted as her boss began to plunge his cock into her tight asshole. Levi wasn't gentle, and wasn't gradual; he pushed insistently against her reluctant ass, as though desperate to be as deep inside as possible.

"Immoral? Unethical? That's as may be, but I like to keep tabs on my employees, as I said, and I am well within my rights to do so."

Riley was stunned into silence, her jaw open wide, not from learning that her boss was eavesdropping on her every moment of the day through an implant in her thigh, but from the feeling of him shoving more cock up her asshole than she had ever taken before.

"Ahhh fuck that's tight!" Levi Growled. He already had nearly half of his cock up Riley's ass, but was encountering resistance

Riley caught her breath and sound began to escape her throat once more "Baby! Be gentle!"

"I'm not your 'baby', I'm your employer. You'll address me as 'Sir', 'Master', 'Daddy', or 'Mr Cochran' if you must, and I'll decide how gentle I will be. Is that clear?"

"Oh fuck!! Y-yes sir!"

"Now, I know you can take this cock to the hilt, so fucking take it!"

Riley steadied her breath, and relaxed, allowing her tight ass to accept more of his girth. Her boss began to slide further into her.

"Ohhhh yes sweetie, that's it..."

Riley felt a flip switch in her brain. She was no longer worried about his size, or his lack of respect for her privacy and autonomy. The only thing she cared about now was accepting his entire length inside of her. Levi was sliding forward steadily now. There was only a few inches left to go, then two, then one, then--

"Ahhhh that's fucking it!"

Riley felt her boss's balls bottom out against her pussy and his groin press insistently against her hips. She had a full 10 inches of man meat inside her asshole, and it felt...incredible. Riley had no idea why she was so nervous or resistant at first. She was built for this. Levi proved what Riley knew all along—that she was a grade A slut with an incredible talent for taking cock and pleasing men. She no longer had anything to fear from Levi's cock; it felt as thought it were made for her. Riley moaned, loud and long, "OHHHHHH YESSSS!"