by JR King
Why I wanted to meet the city’s hottest MILF for one last tryst?
It’s quite simple, truly.
Just meeting Valerie wasn’t going to do the trick. Usual douchebaggery: leverage and no-limits sex. I’d have to nail her in some depraved way to get the job done, thus proving to my infatuated mind and unruly dick that she didn’t have a magical pussy.
Of course she’d felt golden when I was a teenager and she a widowed mistress who knew how to wring any guy out in the sack. Then I grew up. Even if younger, I was the master. I had come to understand that spending fractious amounts of money made Valerie horny. The more she spent, the hornier she got, firing on all cylinders up until she got really knackered. Each time it so happened that her horniness gave me carte blanche. Painful deep-throating, anal sex, the presence of another woman; these were just a few examples of things she’d accepted after retail therapy.
Now Valerie stood in the doorway, loaded shopping bags in hands, her eyes lively. “Champagne and caviar one last time?” she deftly announced the evening’s prescription. Or so she thought.
“Come inside, love. Meet Jasmine,” I answered grimly.
I’d chosen Jasmine because I liked that she looked younger than she was. The dome on her head was blonde and she was skinny as a rail. I liked that she looked illegal, liked that she was wearing a big-cocked strap-on. Perfect for what I had in mind as a parting gift to a horny cougar.
Right, I was such a dog. Considering that straight men love juicy girl-on-girl action, I’d say I was healthful.
Valerie looked flustered and disoriented, weighing her options. Like a guppy, she opened and closed her mouth several times. No sound spilled from her lips as her mind warred with my invitation.
Jasmine, little vixen that she was, pulled on a bra strap so it snapped back against her shoulder. “Are we doing this?”
This wasn’t going the way I’d planned. Unsmiling, I cleared my throat and altered my command, my voice toneless. “Coming or going, Valerie?”
Anxiety was evident in her eyes as she watched me pensively. Fascinated by her toes all of a sudden, she asked, “Why her?”
I cursed inwardly, trying to calm my sadistic fires. “Will you step up to the plate, or not?”
“This isn’t how I want to spend my last day in Boston,” she offered in defeat, pride strangling her words a little.
“Much ado about nothing, then.” I shrugged unapologetically at her refusal, slamming the door in her face. “Goodbye.”
I took a minute to consider answering to the repeated raps on the door.
“Open up, Alex! Open the door!”
Happy I’d gotten a rise out of her, I opened and asked, “Would you like Jasmine to fuck you?”
Valerie nodded blindly.
I became the sort of asshole no one can stand. “Then come in and ask her. Ask her nicely.” To combat my anger and my cotton dry mouth, I turned away and went in search of a drink.
The women spent fifteen minutes limbering up.
“Like, Jasmine?” Valerie’s lips, full and ripe for sucking, were currently posed in the most delicious pout. The Syble babydoll from Agent Provocateur she wore had pink print florals dotted all over, A-line styled with satin bows on the shoulder straps.
“Next,” Jasmine said lowly.
A minute later, Valerie tugged nervously at the hem of the Monica babydoll. It had elasticated shoulder straps and lace detail, and the bra cups were adjusted at the exact angle above the bust, giving off that underwire effect. The pink rosette detail sewn on the empire line teased the eye cleverly. With a shrug, she asked, “Is this better?” The gesture made the left strap of the skimpy babydoll fall off her shoulder, baring her left breast to the height of the nipple.
I was so pleased by the sight of her décolleté that I disregarded Jasmine’s answer. In the clutch of the moment, just when I thought of sliding my cock in between the mounds, I realized I wasn’t switched on—wasn’t attracted to either one of the women. I watched them fuck and roll around in sticky, odorous bedsheets before I went home, showered and changed, and met Aidan at the Symphony Hall.
For those of you out there who think I was a shit heel, I’ll explain.
Hauntingly beautiful music echoed through the halls when the lights dimmed. My eyes were focused on a cello player’s hands as the bow moved fluidly against the strings. The seats were the same but the music was different.
Many years ago, our first date was here.
Remember Nabokov’s Lolita?
I felt like her, loving every minute of it.
“We’re here.”
I bounced up from my seat, trembling, and exited the limo, fumbling with my jacket. Valerie stepped out last and walked up beside me, agonizingly slow. “Is that a new habit?” she laughed as I chewed at the inside of my cheek.
“What if someone we know sees us?” Scuttling aside her, I was like a fish out of water. Daryl Hannah walking beside Tom Hanks, maybe.
“We won’t. Surveillance will make sure of it.”
“We have a security detail?”
“That’s how I grew up. Father hired a young guy, Robert, who will make sure everything’s perfect. Relax and enjoy. You’ll like him.”
I don’t have to spell out the rest for you, do I?
As soon as we were seated, I turned to her and we looked at each other. Lust was in her eyes. Anxiety was in my eyes.
“You’ve never been?” she asked. Her fingers were skittering over my kneecap, and I guessed her intention. The rows surrounding us were empty, the melody enthralling the far-off audience on the right side.
“Not with a woman.” I squashed the lofty smile that tried to curl the hard line of my lips.
“Not even your girlfriend? Your parents have season tickets here and at the opera all year long.”
“Melissa is a sweet enough girl, but her brains aren’t her best attribute.”
“Might as well make it unforgettable.”
My lips curled amusingly at the daring. I was silent, enjoying the music as she leaned in and kissed the skin above the open collar of my slim fit suit. My eyes fell shut and my mind floated, cradled in the addictive miasma of Felix Mendelssohn’s gut-wrenching sonata A Midsummer Night’s Dream.
“Such a beautiful boy.” Valerie’s breath was dewy and minty and warm, her hand caressing the back of my neck. She reached for my belt and teasingly slid the leather from the buckle. I looked up at the feel of her nails tracing the outline of my hardening flesh. I didn’t know what washed over me, I just had a sudden urge to control her, and so I snapped my fingers to the floor. She fell to her knees and her hands slid up my legs. She put her lips to the zipper of my trousers, drawing her tongue along the French fly.
“May I, please?” she begged humbly, her words dribbling down my spine like silvery beads of molten platinum. I felt the heat of her breath as she exhaled over the wool fabric. I reached for my zipper, but her hands had already busied themselves, undoing it efficiently. “Ace?”
I gave her a slight nod and closed my eyes again, refocusing on the dulcet tones. “Be a good pet and suck me all the way down, Valerie.”
She obeyed and gave me a relaxing blowjob.
Right here in this seat.
I realized I’d outgrown that boy in some ways, and in others, I really hadn’t. Isn’t it weird to fully comprehend that at the end of the day, you’re just…you? The point of telling you this is that I wasn’t a monster. I’d always carry Valerie in my heart. A first love tends to stick.
Alexander Turner
The Guys’ Night Out
Gradually, the dreary sky of the afternoon cleared. Fog due to impending rain hung in the air. Alibi on Charles Street was on of my favorite bars, you already know why. Other than that you could find me at Bristol Lounge or City Bar. Very Harvard in intelligence and Abercrombie & Fitch in looks clientele. No backward girls with fake nails, discolored extensions, and pierced belly buttons.
It began with, “Here’s to t
he girls that we love the best. We’ll fuck ‘em in the east, we’ll fuck ‘em in the west; we’ll fuck ‘em in the north, we’ll fuck ‘em in the south; we’ll fuck ‘em in the rear, we’ll fuck ‘em in the mouth; we’ll fuck ‘em high, we’ll fuck ‘em low; we’ll fuck ‘em fast, we’ll fuck ‘em slow; we’ll fuck ‘em standin’, we’ll fuck ‘em lyin’, and if we could fly we’d fuck ‘em flyin’! And when they’re dead and long forgotten, we’ll dig ‘em up and fuck ‘em rotten.”
And then, “Slainté.”
For those of you who aren’t familiar with the term, it was Gaelic for health, so for my boys and me it meant excellent health.
If you’re still interested, the last Saturday of any month was guys’ night out. August was no exception. Most of the day I spent chez moi, watching Elena and working, so time for some fun now, Four Seasons-style.
I was in rare form, Tony was some kind of a grand poobah incarnation, and Aidan was plain miserable. His bonus toast went like this: “To the oil companies I defend even as they destroy entire ecosystems. To the chemical companies I defend even as they knowingly pollute ground water, anticipating mass pollution to fuel the pharmaceutical companies they’re in bed with. To the tobacco industry I defend even as they claim their product has adequate disclaimers. To the pharmaceutical industry I defend even as they peddle untested drugs on the market and embargo extremely damaging results of clinical trials. To all the insurance companies whose claims I help deny, and let’s not forget all the financial frauds and goombahs who are my clients. Due process FTW.”
That snatched the happiness from my face. “It’s a good boner killer. I might inwardly recite it when struggling with endurance.”
Tony said, “That was fucking deep. I’m talking Grand Canyon here. I think we should just acknowledge we live in glass houses, ‘kay?”
Aidan, who was very cause-driven and the inspiration behind many of my private and public views on the environment, said, “So we are evil? Is that it? As a lawyer, where should I draw the line?”
Sorting through the statements, my attention was fixed on the neck of the Corona bottle held nonchalantly between Aidan’s fingers as he swung it back and forth. “What constitutes evil, anyway? Is it something we are or something we do?”
Tony offered, “Padding bills, Aidan. That’s what you do to motherfuckers.”
I allowed the rim of my martini glass to loiter on my lips. Vodka martini that is, shaken not stirred. For someone of my caliber, pulling off the James Bond look is easy. Can’t believe I wrote that, can you? “Is this a popular sport these days? Debate?”
“Debates and sex-tapes,” I heard in perfect unison.
With a scrunch of the brow, I snorted. “Sex-tape? Reeks of schtup, schtup, schtup. Pecker-contest at best.”
The mention of sex-tapes brought about playing Beat That. Basically, we regaled each other with extraordinary accomplishments of sexual nature recently achieved. We loved women, and we cared about our dicks. How could we not? Women were just like Rubik’s Cube. A challenge so frustrating that you want to smash it to little bits and be done with the exercise, but you won’t. For smart guys, we coaxed and cherished as we were compelled to keep playing until we figured it all out. Heck, we’d rather go to war—Trojan-style—for a woman than for oil. If you’re troubleshooting about Trojan condoms, look no further.
Girls were starry-eyed when they saw the three of us. Why wouldn’t they be? Two bona fide CEOs and a top lawyer were quite the sight. As a trio that had far too much disposable income, and—even after having worked at a steady clip all day—had a great deal of expendable energy left, we were enviable, consequently cumulating stares of disbelief. But, to be young, wealthy, and good-looking in Boston had its disadvantages. It was quite annoying that the women we spontaneously met wanted to become permanent fixtures in our lives. The look how perfect I am as your slave kind of thing disgusted us.
Hazardous as it was, love at first sight wasn’t part of our repertoire on guys’ night out. None of us sandbagged girls with flowery words about dating, or a relationship, or a fucking future together. In short, we were looking for a good time for one night, and made it clear as we skipped cheesy lines and told the truth, which is better than what most single guys did. Was it our fault if women got attracted to us, tasted our cock, and suddenly wanted to appear in the family Christmas picture? If truth be told, that shouldn’t be our problem. Before physically engaging, we gave the lowdown then showed the girl the time of her life, and made sure she was driven back home stylishly and safely. Forget getting our phone number. Besides the fact that none of us were phone talkers, with our level of clout, we sure as shit wouldn’t call back a one-night-stand type of girl, there’s a clear distinction to be made here. Our parents had raised us to be gentlemen: there are girls you fuck and girls you marry.
After a few more rounds, “It’s cinched. Tony’s oh for two,” I concluded. “Best jack hammering technique, I should write it down.” Tony wouldn’t lie about fucking some Italian model into oblivion. Having witnessed his prowess with women firsthand, I was relatively certain of the story’s validity.
“Two young Indian women are checking us out,” he appraised us.
Aidan asked, “Steel or casinos?”
I traced the direction of Tony’s gaze. I could see the lusty glossiness of their eyes from where I sat. “Steel, fucking steel,” I told him. “Dibs on the left one.”
“Too early for pussy, Alex.” Aidan slammed back the last of his beer. “What’s the POA?”
I proposed, “How about Jean-Georges’ joint at the W?”
“Heard through the grapevine that Starwood is struggling to keep that thing afloat, boys.” Tony’s truffle pig grunt sounded like vacuum-cleaner noise. “Place will burn out in two years, three years tops. I wouldn’t be caught dead eating there.”
Ignore him, Tony was jealous of my Starwood shares. “I assume you’ve got a better idea, 007?”
“Zagat,” he answered.
Not exactly the restaurant bible, but since the elitists at Michelin that had a keen eye for fine dining hadn’t bothered to rate Boston, we consulted Zagat on our iPhones. As charmed children of a meat-and-potatoes type of household, hipster organic tents and granolified restaurants that used tofu and seitan and tempeh—or other soy-based products—as meat analogues weren’t our thing. Tacky places with laminated or ring binder menus weren’t high on our list either.
Tony was the first one to dip his feet. “Wellfleets at B&G? ‘Tis the season. Or how about the new trattoria on Newbury?”
“I second the second one,” said Aidan, casually waving over the waitress to settle our bill. When she swooped in to pick up his credit card, I noticed her nails were and acrylic horror, nightmarishly long and painted a hideous shade of orange. I had no way of knowing if her toes matched, she wore ALDO pumps.
“Good save.” I lifted my hand to look down at my Audemars Piguet wristwatch. “We can make second service.”
Before standing up, we had a custom of individually repeating this tongue-twisting alliteration three times: Peter Piper picked a peck of pickled peppers. Just to make sure we weren’t buzzed to the point of doing a face-plant.
Each of us passed with flying colors.
Okay, perhaps I exaggerated a little here…
Glancing at the table beside us, Tony asked Aidan, “Didn’t you tap that a fortnight ago?”
The stupid grin fell off Aidan’s face.
Tightening my tie, I spoke to no one in particular, “What did I miss, Mr. Darcy?”
Aidan put his hand to his heart, a dorky smile on his face. “A true gentleman never kisses and tells.” Then he added, “Left handed layup. Nailed the wench hard three times, lads.”
“It’s the artificial blonde, champ,” Tony informed me.
I hardly checked out women, but when I did, I specifically went for the tits first, ass later. That’s the way to do it. Single or committed, any man who maintained he was a paragon of moral perfectio
n and never eye-fucked women is really a pathological liar; we have eyes, right?
The e-cigarette Ms. Double-D in a size zero dress with bleached blonde hair just fitted between her lips promptly fell from her mouth. Her fingers fumbled in her lap and, after a refitting, her rake thin girlfriend removed the sparkly object. Pretty enough and very queen-bee style, I would fuck her.
“I hope she’s on the pill,” Aidan said as we all stood up. “I’ll piss myself to death if she isn’t.”
I looked at him, slack-jawed. “You brainless twat,” I wanted to shout. I didn’t do that, though. “Did you shoot baby batter into her without making sure she was?”
“Quite possibly. Judge not, lest ye be judged, Alexander the Great.”
I whistled slightly bare. “Nice stunt. Fucking congrats if there’s a bun in the oven.”
“Bad booty call.” Aidan doubled over as if he’d been gut-shot.
“Fucking faggots,” Tony muttered. “Gentlemen, paparazzi trash is larking about. No hitting on the noggin, or else Jerry might detesticulate you.”
Our antics always made good fodder for the Ihavenolife kind of gossip columnists. I might have forgotten to mention it; Jerry Parkman represented the three of us. Fastening the top button of our jackets as we stood, we proceeded to exit the Four Seasons Hotel head down. Our names were called from several directions. A valet opened the limo door, and the pop and flash of cameras erupted like a small lightning storm.
“Aidan! Big win this week! Dating anyone?”
“Alexander! Over here! Quick one!”
“Tony! Look here! Any truth to the rumor of an engagement to the Italian model? Pre-bachelor party tonight?”
We didn’t pose for pictures, only smiled and waved as we climbed in. A fast limo ride later, Tony’s bodyguard was leading us into the newest eatery on Newbury Street.
Time for a history lesson, dear one. To quote Emerson, a friend may well be reckoned the masterpiece of nature, and I had two of those. The guys were tall and leanly built like I was. There was Aidan, my childhood friend, a firebrand lawyer for a white-shoe firm who could dissent any argument. Because he was heir to the fortune of one of the most influential American families, many feared him—few knew him for the gentle person he was. With his boyish physiognomy of curly brown hair slicked up in a tapered crew cut and joyous green eyes, he looked more like an overgrown teenager than my elder. Just one year. Then there was chiseled-face and copper-haired Tony, who since Harvard had become my dearest friend. His rough-hewn handsomeness and swimmer’s build rivaled mine fiercely. The two of us got plenty of tail while at Harvard. Looks were a tool of our trade, something we used to snare resources when we partied too hard and didn’t put in work. Cock-gobbling sluts literally begged us to do MFMs. You guessed it right, MMFs: not going to happen. I loved these guys like I would love a brother.
