Work Hard, Play Hard

Liam was balls-deep in Alice, trying to ease a tension headache & work through all the things that were bothering him. Screwing the little Belgian or Bulgarian slut (wherever) had been better than this, but perhaps it had just been because Elena was still fresh & new to him, whereas he'd worked with (& had access to) the paralegal Alice for nearly three years. He pulled out, crouched, spat on her shaved pussy & stuck his cock back in.

Since he'd taken the au pair in the bathroom a couple of months ago he'd been able to sneak in a few rides on her each week without arousing his wife's suspicions. It was convenient having the cunt living under the same roof where he could get at her whenever Jules was distracted or had taken sleeping pills. Last week he'd finally fucked the young woman up the ass & it had been phenomenal, the 18 year old was extremely willing, extremely responsive but she'd drawn out the process, had made him wait, work for it.

The frustration & challenge had been tantalizing & when he'd finally bent her over, on the incline bench in his personal gym, the victory had been more satisfying somehow. He'd taken her savagely & after he'd had enough he'd made her finish him off with her mouth, made the little tease savour her own ass-juice from his dick. She was a natural tease. He remembered how she'd teased him in the shower that first day, how she'd made him lose control on the tiled floor.

He'd discovered, to his delight, what a natural little actress she was. After that first time, on the bathroom floor, he'd felt more powerful than he could remember, having forced his way inside her. He'd loved that feeling, it felt like the reverse of his dynamic with Jules, or Trev. He'd asked her, told her really, to 'put up a fight' every now & then, while he was getting in her. & she had, wonderfully. He was amazed at how great at role-play she'd been, perhaps even better than Jules! (Although in a very different genre). Elena was able to materialize tears on demand, more convincingly than a lot of professional actors. As a man who'd a lot of sex, (perhaps a bit of an addiction it had been suggested), he was always looking for something new, something 'more'.

In the gym she'd beckoned him with her finger & then she shoved him in the chest. He'd twisted her around before ripping her leggings & fucking her in the tight little asshole & she'd put on an award-winning performance, begging him to stop, telling him it hurt, tears streaming down her pretty young face. For a moment he'd even worried it wasn't an act, but afterwards, she'd sat her cunt on his lap & had ground herself happily against him, asking if he'd 'enjoyed her performance'. He really had. He'd loved growling at her to 'take it' & loved telling the dirty slut he was in charge. She'd definitely earned a good bonus that month.

On his desk the little brass tube containing his fountain pens rattled with each thrust he made, he'd have to remember to put it somewhere else the next time he used Alice like this. He glanced down, she was writhing under him, biting the knuckles of her left fist, the other hand flat against the desk trying to brace herself. He drilled harder. He usually liked how submissive she was, but in the next contract negotiation he'd suggest she up her game with flirtatiousness, enthusiasm, playfulness. She seemed to have become a bit of a starfish lately. Again he wondered how he'd navigate the logistics of a threesome with Alice & Elena, would it be easier to get Elena to his office, or Alice to his home? Or should he book a hotel room for an afternoon (maybe he could set up a hidden camera or two before the girls checked in).

Meanwhile, Alice's contract negotiation was coming up too, which meant both partners in the small firm (himself & Matthew Chan) would evaluate her at the same time. He loved those half-year meetings, Alice was a great sport, it was fun to get on either end or DP her. He slowed his thrusts a little as he thought about Matthew's smooth brown cock. It was smaller than his (he'd yet to find one that wasn't) but so, fucking hot. He imagined sucking it, but the one time he'd attempted taking a step like that with him, (the last time they'd been DPing Alice together), he'd been irritated when Liam had tried to give him a helping hand. Matthew wasn't just straight, but overtly homophobic. Liam cringed when he remembered the look of disgust on Matt's face & hoped he'd accepted his excuse that the crystal they'd smoked had made him do it.

Liam was homophobic too. He was straight (& certainly acted it in public) but had a dark secret, that he'd been bottoming for someone since he was in his early 20s & even with Elena, he'd wanted the feeling of Trev's dick rearranging his insides from behind. Perhaps it was just the novelty of receiving anal sex, of being physically overpowered, but he was finding himself more & more hungry for cock lately. He'd even looked up some gay cruising locations, read a SubReddit & masturbated to photos the guys had posted. He'd left the office early that day, & had gone to a dingy bar where he knew there was a glory-hole in the bathroom stall.

He'd sat on the toilet seat for nearly two hours, jerking himself off & watching porn on his phone. He'd almost been ready to give up when finally, a hairy red cock poked through the hole (Liam's had been too wide to fit, he'd tried). He'd jerked the guy off & then; sucked. It was the first time he'd had anyone's dick (aside from Trev's) in his mouth & he'd still been inexperienced, but it had seemed to satisfy the anonymous guy on the other side of the stall, Liam swallowed the load. He'd gone back the next day, & the next. He was really developing a taste for it, not just for cum but for dick.

He'd soon worked out that the first time he'd been too discreet going to the bathroom, the trick was to make eye contact with someone in the bar first, give them a little nod, then he didn't need to wait all day for attention. After a few weeks he'd used a pocket knife to widen the hole enough to poke his own cock through & he'd found himself becoming a very popular attraction. A few times the bartender, a bearded African American man with a pot-belly, had performed fellatio on him. Finally the man had told Liam he'd wipe his bar tab if he'd breed him. Liam could obviously afford the drinks but he'd been intrigued & while another man handled the customers he & the publican had sojourned to the kitchenette & he'd fucked the man, who'd ended up being incredibly vocal & appreciative. It had been his first time as a top, as well as with a black guy, after all the noise he'd been too shy to leave via the front so the man had let him out the back.

It had been a fun new experience but Liam still preferred to fuck pussies & he doubted he'd do it again, he liked the consistent, wet pressure of cunt, & he preferred to BE fucked by men. A few days later the bartender, John, had returned the favor & bred Liam. He'd closed his eyes & pretended it was Trev, or that Trev was watching them. Fuck that was hot. Trev was so naturally dominant, he knew just how rough to get, just how hard to make Liam take it. In many ways, Jules reminded him of Trev & sometimes, to his shame, he wondered if that's why he'd married her. He was both turned on by, & resentful of the power his wife had over him. Perhaps he wanted to be dominated by men, but he thought he wanted to dominate women.

Years ago, when they'd first met she'd made him chase her attention. She had an icy, untouchable air & he'd been dying to see what she'd be like with his dick in her mouth. At the time she was still a junior at Albrecht-Asprey (yes, THAT Albrecht-Asprey) but had already been known as 'the financial witch' (oftentimes bitch) in their circles. The more she ignored him, the more he wanted her. He'd all but given up when she'd been so disinterested at the launch party for his new firm with Matt (where he'd hoped to impress her).

It seemed like everyone had left (including Matt) aside from the catering staff who were cleaning up, collecting their platters & chafing dishes & he & Trev had snuck into the stairwell together. Liam had been gratefully taking his cock up his tailpipe, his hands braced against the safety railing, whimpering 'fuck me, fuck me, fuck me'. He'd just felt Trev squirt inside him & was turning around to beg him to suck him off when he'd seen Jules leaning casually against the fire exit door, watching them. She had her phone out & he guessed she'd stepped into the quiet space behind them to make a private call.

Liam's first instincts were to yell at her, or sprint away, or cover his face but she'd smiled knowingly & just said "he ain't heavy, right, brothers?" & chuckled & made her way past them down the stairs. Liam had been too stunned to finish & he & Trev hadn't said a word to each other. He'd almost had an anxiety attack driving back to his apartment but the next morning she'd sent him a text asking if he'd like to pick her up for dinner at 9pm that night. After six months of practically ignoring him, SHE was asking him to dinner. He'd showed up at her loft at exactly 9pm & was impatiently standing outside her door, about to knock when she opened it. She was in a full latex bodysuit, no mask, but blonde hair in a tight, high ponytail. There were two perfect circular cutouts for her incredible tits, a full, bouncy pair with large pink nipples that made his mouth water & from her crotch stood a large, bright red dildo.

She was dangling a leash from one of her long fingers & he'd wordlessly come inside, entirely forgetting the tense argument he'd had with the maitre d of the most overpriced restaurant, where he'd aggressively negotiated a last-minute reservation. He mutely removed every stitch of clothing & allowed her to fasten the leather collar around his neck. She'd picked up a small riding crop from a bar stool & led him to a floor to ceiling mirror. He'd braced both hands against it, spread his legs & bent over & she'd whipped him until every patch of his ass & balls had been red & swollen & then deliciously, fucked him hard, choking him with the leash as she did.

He looked at his reflection as it happened, staring into his own tear-filled eyes, gazing at his own red face as he gasped for air, his mouth a surprised 'O'. She whispered behind him "good girl, let mommy fuck you. You spread your pussy, mommy's going to fuck you like your brother fucks you. You're a pretty girl. Take mommy's dick baby-girl." It was the first time he'd been pegged, the first time he'd received the attention of a dominatrix & he almost proposed marriage right then, with the massive red dildo reaming him until he came in thick ropes of jizz against the mirror. She still called him baby-girl in the bedroom, it felt weird now that they actually had twin baby girls.

With a loud clatter the tube holding the pens & some other things had rolled off the desk & hit the floor & Liam was jerked out of his daydream & back to the present. Alice's poor cunt must've been feeling pretty raw by then, he supposed. She'd need tonight to recover before she visited Matthew's office for his turn on her for the week. Their law firm was small, 'boutique' they called it, so she couldn't afford to pause her traditional office work for more than a couple of sessions each week. Although sometimes, if one of the partners was either under a lot of stress about a case, or was conversely celebrating a big win, they'd add an extra session, or a quickie.

A few days ago Liam had facefucked her in one of the handicapped stalls at the King County Courthouse on the third floor. Not for any of the above reasons, more from boredom. While she was gagging on his dick there'd been a knock on the door, he'd opened it to find one of the pink-faced junior clerks curiously peeking inside & he'd let the young man join them. He'd briefly considered giving him a go with her but instead, had just let him watch & jerk himself off. Watching the young guy rub one out had been great, it even helped Liam finish. Alice had gobbled his knob & swallowed his stringy ejaculate. He'd given the clerk a business card & the lad had promised to ensure their paperwork would get VIP attention & be filed quickly from then on.

He ignored the spilled pens but saw the clock & decided he should wrap this meeting up. He snapped his fingers & pointed at the floor. Alice got down obediently on her hands & knees like a dog wearing heels & stockings. He always insisted she wear stockings, preferably with a garter belt (they reminded him of Jules). He grabbed his tie, which he always lay on the back of his chair when he was plowing her & made her bite down on the middle section of the silk. He wrapped the ends around his fists a couple of times & knelt behind & thrust his dick back into her red & chafing slit. She moaned through the makeshift gag. Then, pulling the tie like the reins of a horse he resumed his fuck session.

What had he been thinking of earlier? Right. Matt's offer. Matt was the kind of man who knew everyone, who always knew a guy who knew a guy who'd be able to get them what they wanted. He wasn't as successful in the courthouse as Liam, but he'd been worth his weight in gold when it came to hooking big clients. No matter what city or State they were in Matt would figure out the best clubs, the best drugs, the best girls. The most recent time he'd been in Oregon (on a last minute work trip that interrupted his birthday plans) Liam had entered his hotel room & found two perfect naked specimens giggling & showering together in his bathroom. For a second he'd been irate that the suite had been double-booked, or the girls had been able to break in somehow, but then he saw the card from Matt saying 'happy 41st' with a bottle of Hennessy.

Soon he had one eating his ass while the other girl deep-throated him. Then he'd fucked girl-one & girl-two had twisted the neck of the cognac bottle into his asshole & fucked him with it at the same time. He couldn't tell them apart, they may well have been twins for all he cared. It had felt incredible & he'd closed his eyes & imagined doing something like it with Trev. When he'd cum on the girl on the floor, the other girl had made a beautiful production of licking her friend's tits clean. He'd almost been late to the meeting he'd been in town for, & had arrived at Andina Restaurant still smelling faintly of whore pussy. He'd nailed the pitch though & when he'd returned to the suite after midnight he'd woken the young sex workers up for round two.

Now Matt had landed their biggest & most connected client. 'Oscar' as they referred to him, (also known as 'the Hollywood Heavyweight' by the press), was a screen legend. He'd burst onto the scene as a young man acting opposite Marlon Brando in the mid 70s. He had longtime working relationships with Scorsese AND Polanski. His public reputation was as a silver screen powerhouse, often starring as a gangster or serial killer (there were rumours he was friends with both in real life).

His private reputation was as a connoisseur of the perverse, a gonzo journalist of sexual depravity & gratification, as Hunter S Thompson had been for drugs & bikers. Matt had secured their contract with Oscar in part with Jules' assistance, whom he'd insisted on taking to LA with him while he pursued the whale. Liam understood better than Matt what an asset she was when it came to convincing the super-privileged. Her good breeding put them at ease, as did her credentials & position at Albrecht-Asprey. She'd been the deciding factor when the legend had finally chosen to switch to their smaller, but very motivated firm, especially when he'd been assured he wouldn't just be receiving legal advice but also top-notch investment strategies. Liam would have liked to have joined them on that short trip, of course, but had been arguing at trial those days. Regardless, Matt & Jules had sealed the deal.

Now Matt was teasing him with hints at an exclusive erotic invitation at Oscar's Paul R Williams designed mansion. He'd been stingy with details but had dropped enough hints that made Liam's cock rock-hard. Not to mention he was dying to spend more time interacting with the glitterati of the entertainment world. What was the point of representing the dirty old man (aside from the fees & prestige) if he couldn't party with celebrities?

Knowing Matt, he imagined the 'invitation' was to something especially fucked up & he was desperate to secure a spot. But Matt had insisted that in exchange for greasing the wheels, Liam would need to 'introduce' him to Elena. That definitely meant he was going to try & get in her if he could. OBVIOUSLY Liam wasn't intimidated, he'd seen the size of his coworker's cock many times, but something about the whole situation irked him. First of all, he hated feeling like he was being 'shaken down' by Matt. He shouldn't have to beg him to include him, they were equal partners. He felt like Matt was flaunting the fact that he was 'the people person' when it came to their organization.

Secondly, Elena was HIS. Sure, they'd shared chicks before, even from their first trip to a stripclub together, before they'd even gone into business they'd stretched a few dancers between them. Sometimes, when they both hired escorts they'd swap the girls halfway through the night for a bit of extra variety (the gold digging sluts would whinge until they paid them a bit extra but it was still cheaper than hiring them two separate times). But there were some pieces that were off-limits. A live-in nanny, like a wife, or a girlfriend, should be off-limits. He'd found her, he'd broken her in. She was his & he didn't want to share her.

He also felt as though she'd been given to him by the universe (if that wasn't too airy-fairy). She'd been a little reward for how much shit he'd suffered while his wife had been pregnant & then the mess the twins had made of her pussy for a while & how exhausted he was, because he'd wake up sometimes when he heard them crying. Not to say he didn't love the twins. Obviously, he loved those little girls. But he hadn't exactly jumped for joy when Jules had said she was pregnant, all that change hadn't been easy.

Plus, he planned on getting Elena to peg him, Jules had been so busy with the babies & work that some weeks she barely got around to it. He was so hard-up for prostate stimulation & domination that a few times he'd even considered the five hour drive to Trev's place, just to get fucked properly. That couldn't go on. He needed a more reliable source of satisfaction. But could he count on Elena & Matt not to discuss his proclivities? He'd draw up another NDA for Elena, an even more aggressively worded one but still... he couldn't have Matt suspecting he wasn't 100% straight. He WAS 100% straight, he loved pussy. It's just that physically, getting a dick in the ass gave him something extra. But he wasn't queer. He wasn't.

He wasn't.

He was pulled back to reality by mumbling, Alice was trying to say something through the silk tie that was digging into her mouth, it sounded like she was asking how much longer. He sighed. Sometimes, the crystal he smoked made it more difficult to cum, & he was distracted, under a lot of stress. He yanked the tie a little to shut her up. Then considered & pulled the 'reins' into his left hand & felt around under the desk with his right. Got it. A small tear-drop shaped glass award on a little dias from the California Law Association or somewhere. It had fallen off the desk along with his pens. He couldn't believe he hadn't thought of it earlier. He paused thrusting for a moment while he gently pressed it into his ass, careful of the smoothly faceted edges.

It worked, when he resumed riding Alice's pussy the feeling of the cold glass filling his hole brought him to an overdue climax. Just before he came he pulled out, twisted the young woman around to face him & creamed all over her forehead to punish her for telling him to hurry up. God that felt better. He felt his shoulders loosen, his headache eased. He was careful to stand up with the award still clenched between his cheeks & stayed facing the paralegal so she wouldn't see how he'd finished. She'd bent to pick up the pens & accoutrement that had been shaken off his desk earlier.