Watching Her With The Lawyers

by Summers, A. B.

  WATCHING HER WITH THE LAWYERS

  A.B. SUMMERS

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  The WHILE MY HUSBAND WATCHES Cuckolding Series:

  While My Husband Watches

  While My Husband Watches 2

  While My Husband Watches 3

  While My Husband Watches 4

  The WATCHING HER WITH Cuckolding Series:

  Watching Her With The Neighbor

  Watching Her With My Friend

  Watching Her With My Boss

  Watching Her With The Waiters

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  WATCHING HER WITH THE LAWYERS

  A.B. SUMMERS

  1

  Mark the neighbor in my living room . . .

  My old friend Thomas at the downtown Hilton . . .

  My two bosses, Franklin and Stephen, at Franklin’s mansion in the suburbs . . .

  Those three waiters, Henry, Richard, and Jackson, at our favorite restaurant, Hogarth’s . . .

  My head spins as I review the history of our marriage over the past year. I’ve now watched Cynthia with seven different men, and I’ve joined in each time. The heights of ecstasy we hit were unparalleled, beyond our wildest dreams. But all of it came at a price.

  At first the price wasn’t much. So we cut Mark the neighbor out of our lives after that first ménage, when he took my wife from behind, pouring his cum deep inside her asshole while I came in her mouth. Then I made sure my old friend Thomas was no longer welcome into our lives. No problem there. But then we started to up the ante.

  The first time I saw Cynthia get taken by two men, it was my two bosses who filled her from top and bottom, front and behind, above and below until I could no longer hold back and forced myself in there, once again pushing my cock into my wife’s mouth as two men fucked her raw. The rush was incredible, but I paid for it with my job, writing my resignation letter the very next day.

  Watching Cynthia with the waiters, my wife getting airtight on that table as those three young men filled every hole . . . man, that was worth it. Too bad we’ll never go to Hogarth’s again, but there are plenty of good restaurants in town.

  So yeah, it’s all been worth it. I think so and I know Cynthia does. But I can’t help notice the disturbing pattern of escalation that’s happening with us as we go deeper and further into the hotwife lifestyle. Each time now it’s been one more guy, one more cock, one more set of swinging balls slapping against my sweet Cynthia’s chin as she sucks and moans, fucks and howls, spreads and screams. So how far can this possibly go? Just one man is almost out of the question for us now. It’s just too fucking mundane, as ridiculous as that sounds! Two men sounds like a stroll in the park—nice but not really exciting. Three would be great again, but how do we find three men we sort-of know but not well? After all, Cynthia and I had agreed early on that we wouldn’t turn to the Internet to find random fuckbuddies, and neither would we hit up any close friends. But our rules have trapped us, I feel now. Where do we go from here?

  Can we go back to the restaurant? Unlikely we’ll get away with it again. And besides, it’s a been-there-done-that thing now. This is about adventure and experimentation, and it needs to be new every time. That’s the only way we can recapture that high.

  Cynthia feels the same way I do, I know. She is way past that restless stage already, that stage where we fuck in the dark, lights out, me always taking her from behind while she rides her dildo and sucks on my fingers, both our eyes closed tight as we come like animals in the night. It is great, but that beast inside us needs to be fed.

  And this time, it is Cynthia who’s going to bring home the bacon, serve up the beef, feed that beast that’s pulling at its restraints, yearning for a new experience, something more, something harder, something that’s going to come at a price.

  And the price, this time, is going to be her job.

  2

  Cynthia works at an advertising firm, but recently she’s been working with a lot of lawyers. Four lawyers, to be exact. Day in and day out for the past two months, all five of them packed into a conference room up on the eleventh floor of the Capers Tower downtown.

  Cynthia’s firm is getting sued by a former client for something they put in one of their ads. Not unusual, but this case could involve big money and so the firm assigned Cynthia to work with the lawyers full-time as a liaison to the rest of the company as they gather information and prepare their defense.

  She had a hard time at first, she told me. Her advertising firm is well-regarded and so they get to hire the top graduates from all the top schools. For the creative departments this works out great, because you get a lot of smart, earnest young people. But for the “harder” departments like accounting and legal, you basically get . . .

  “. . . a bunch of assholes,” Cynthia had told me after her first week confined to that conference room with them. “All four of them.”

  This was a couple of months ago, and I remember it well because we fucked hard that evening before dinner, with Cynthia asking me to pull her hair while sliding two fingers into her asshole as I took her from behind. It was a pretty wild session, I remember, with Cynthia bucking and grunting as I pulled her pony-tail. At one moment she was snorting so loudly I thought I was riding a horse—a mare in full heat, of course. Holy shit I came HARD that day!

  Now I am getting hard just thinking about it, which is too bad because I am at work. I could go jerk off in the bathroom, which I do sometimes. But lately I’ve been holding it in for when I get home, because Cynthia’s been insatiable these days again . . . yes, these days as that restlessness is creeping back into us . . . that yearning for another session . . . new men, new cocks, new situations.

  Which takes me back to that day Cynthia complained about those lawyers:

  “Assholes,” she said again after both of us came and were lying on the couch together, sweaty and wet, the smell of semen and cunt heavy in the air. “Every one of them. Just because they all went to law school at fancy universities and are getting paid well into six-figures, it doesn’t mean they can treat everyone like shit.”

  “No, it doesn’t,” I remember saying to Cynthia as I glanced at her exposed nipples, then reached over and casually plucked at the dark red tips, stroking them until they got rigid and pointy again.

  She barely noticed, her face pointing straight ahead as she talked. “Fucking Jack, with his pinstriped suit and striped shirt. Who wears a striped shirt with a striped suit!”

  “Ridiculous,” I mumbled as I leaned forward to suck on my wife’s other nipple. I was now
here near getting hard again, but over the past year Cynthia and I have become so familiar with one another’s bodies and sexuality that it’s almost second-nature for me to pull on her tits, squeeze her ass, finger her asshole even if we’re not about to have sex or anything.

  “And that guy Marcos,” she went on as I caressed the smooth white skin on her wide hips. “Fine, I get that he’s from Spain. But I really think he puts on a much heavier accent than he needs to. He’s always drawing out his sentences, putting emphases on strange words. It’s almost an Italian accent that he puts on, like maybe he thinks white American women are going to swoon over him.”

  “Do they?” I whispered as I licked her cleavage.

  “Do they what?” Cynthia said, looking down at me. “Are you even listening to me?”

  I chuckled as I looked up at her smiling face. “Of course I’m listening. You said this Spanish guy was faking an Italian accent to get American women to swoon over him. So do they swoon over him or what?”

  Cynthia shrugged. “Probably. I can see him convincing a few women to suck his cock.”

  I laughed even as I felt my soft cock stir at the thought of my wife being convinced to suck this lawyer’s Spanish cock. “What about the other two lawyers?” I asked her quickly.

  “Well, there’s Anders, who’s half-Swiss, half-German or something. Tall and blonde. Kind of soft-spoken, but when he does talk, he proves himself to be a world champion asshole like the rest of them.”

  I laughed again as the picture in my mind expanded to three men with my Cynthia now: Jack in his striped shirt and striped suit, cock sticking out of his pants. Marcos smiling and nodding as he explains to my wife how wonderful it would be to suck his Spanish-Italian dick. And then Anders, quietly standing over my wife as he jerks himself off while mumbling shit like, “Achtung!” or “Schnell!”

  “Who’s the fourth guy?” I remember asking as I felt Cynthia quiver a bit as I began to stroke the front of her pussy with the back of my hand. She was getting hot again, I could tell, and I wasn’t sure if it was because she was thinking of this fourth guy or if my playful stroking was getting her going.

  She sighed as she slowly opened up her thighs, exposing her pink lips that were peeking out through her thick brown pubic hair. She let me stroke her pussy lips for a while as she stayed silent, and I do remember getting a distinct feeling that a fantasy was forming in her mind. I didn’t care, of course. In fact I loved the idea. After all, I was already fantasizing about those three lawyers she described standing over my naked Cynthia. The only thing that would make it better would be adding a fourth to it.

  “The fourth guy is Parker,” Cynthia said finally, her voice low and husky as I put the tip of my finger into her pussy while I touched the hood of her clit with my thumb. “He grew up poor in the Bronx and ended up graduating at the top of his class from Columbia Law School. And I guess I kinda expected him to be a bit more down to earth based on his roots. But nope. He’s as arrogant as any of those other guys. I mean, I really thought he was going to ask me to make him coffee and then rub his feet, the way he was ordering me around this week.”

  “Would you have?” I whispered then as I pushed my finger all the way inside her, feeling the wetness start to flow from my wife’s depths again.

  “Would I have what?” Cynthia muttered back through a moan as she adjusted her hips and spread her legs wider.

  I smiled devilishly as I curled my finger up inside her pussy. “You know what.”

  Cynthia’s eyelids were already fluttering and her mouth was opening and closing like a fish as she took long, deep breaths, her heat rising as I fucked her with my finger. I was enjoying this tremendously, just like I know she was. By then we were already comfortable with the idea of Cynthia fucking different men while I watched, and I knew she was playing with me when she asked, “Would I have what?”, just like I wasn’t talking about fetching coffee when I asked her, “Would you have?”

  “Would you have . . .” I whispered again as I pushed a second finger into her and felt her body quiver. “Would you have . . .”

  She was nodding by then, her eyes closed tight, her mouth forming an O shape as I was certain she was imagining a cock pushing its way down her throat. Yes, a cock, and not my cock. Hah! Oh, fuck that turned me on!

  Her orgasm rolled in soon after that, rocking her naked body through and through as I furiously rammed my fingers as deep into her cunt as I could, my thumb flicking and pressing her stiff clit as she moaned and thrashed.

  “Would you have, Cyn?” I kept whispering as I watched her come. “Would you have?”

  “Yes,” she moaned as she finished. “Oh, fuck yes.”

  And finally, when she went still and I took my fingers out of her pussy, bringing them to her face to sniff for a moment before smelling them myself, I asked her the question:

  “Will you?”

  3

  Of course, she said no at the time. It would have been career suicide. Besides, she thought the guys were assholes, and why give assholes the pleasure of coming all over her face, down her asshole, inside her pussy? It wasn’t even a consideration at the time.

  But that was two months ago, and now as I sit here in my office, I cannot help but think that there’s a reason this is all coming back to me now. We’re looking to take this one step farther, aren’t we? Raise the stakes? Up the ante? The last time it was three new men. Now it’s time for four, isn’t it? And we’ve got four ripe for the picking. Four lawyers. And there’s something about the idea of watching these four young, arrogant, Ivy-Leaguers groan and shout as they come all over my Cynthia that makes me excited.

  I think about it all day in the office as I go through the motions, answering emails, shuffling papers, getting on conference calls and trying to sound professional. My cock is hard all fucking day, and my underwear feels wet from all the pre-cum that has been oozing out of me as I imagine my Cynthia with these four lawyers, every cock hard, every hole filled.

  I imagine myself watching, perhaps standing outside the conference room. Maybe it’s one of those rooms with the glass walls. Maybe it happens at night, with all the lights off in the office except for the bright white lights of that conference room. The room is lit up like a stage or an arena on Fight Night, and I think of my sweet Cynthia getting undressed by these assholes, pushed down onto the cluttered mahogany conference table, spread wide, opened up, cocks fighting for access to her mouth, her ass, her cunt as she writhes and gasps, whimpers and shivers, sucks Marcos’s big brown cock while jerking off Anders’s long white one, bucking her hips as pinstriped Jack comes in her asshole even as Parker stretches her cunt with the girth of his made-in-the-Bronx shaft.

  Somehow I make it through the day without jerking off or coming in my pants, and I drive home as fast as I dare, barely stopping at the Stop signs in our neighborhood as I screech into our driveway as if my sex drive is fueling my car.

  But I am disappointed to see that Cynthia isn’t home, and I fucking SHOUT in frustration as I crack a beer and sink into the couch to wait, my cock still semi-hard despite my annoyance. Still, I hold back from rubbing one out, and I decide to wait for my wife.

  Cynthia is in a foul mood when she gets home, and although she is usually ready to have sex in the evenings before dinner, she is clearly not in the mood right now. So although I have been aching for it all day, I grit my teeth, hold my horses, and ask my wife the classic question:

  “Babe, what’s wrong?”

  She forces a smile as she tosses her bag onto the couch and slips off her shoes. With a sigh she sinks into the armchair, and I sit down across from the coffee table, my cock pitching a tent in my pants, a patient smile on my face as I wait for her to respond.

  Cynthia glances at my cock and lets out an exhausted chuckle. “I know, honey,” she says. “Just give me a minute. It’s just been . . .”

  I nod and then
shake my head, indicating that hey, I have a hard-on, sure, but I am here to talk. I am always here to talk.

  “The lawyers?” I say without thinking.

  She looks at me with surprise for a moment and then nods. Things have calmed down with the lawyers since the first few weeks, so she hasn’t talked about them recently. But I know the case is drawing to an end and tensions are running high as the five of them work long hours under serious pressure. Still, Cynthia hasn’t complained about anything specific besides the long hours for over a month now.

  “Yeah,” she says finally. “For a while there it seemed like we were all getting along. I mean, they were still assholes in general, but after the first month they stopped being assholes to ME, you know? They saw that I was a great asset to their team, and it almost seemed like we . . . we . . . were having fun.”

  I nod and then shrug. “Yeah, babe. But now the pressure’s back on again, right? You said the case is almost done, and everyone’s running on low sleep. When the stakes are high, people get nervous and defensive. Don’t lose your cool, hon.”

  Cynthia takes a breath and blinks as she smiles at me, a clear, affectionate smile. “Yeah,” she says, and now her expression hardens, and I swear I see some anger in there, maybe even fear. Mostly anger though. “Yeah, the stakes are high. And the case is almost done. But things aren’t going our way. Most likely we’re going to have to settle out of court, and our company is going to have to pay up big.”

  “Really?” I say. This is news to me, and it is bad news. “How bad is it?”

  Cynthia sighs again. “Bad. Like someone-may-get-fired bad.”

  I raise my eyebrows. “Who? You?”

  Cynthia smiles now. “I hope not. Probably not.”

  “One of the lawyers?” I ask.