Oysters & Chocolate


Dirty Martini

The First Time I Went Whoring

By: Ilan Mochari

Tags: Fetish Money Shot Porno Shot Prostitute

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More than dog-style fucking; more than tight-lipped oral; more than snug, intimate anal—my favorite sex act, bar none, is the admittedly onanistic pleasure of climaxing on a woman’s face and watching the semen drip down her cheeks.


And here’s the thing—I’m also a serial monogamist, a thirty-two-year-old restaurant manager whose bedroom partners have always been serious girlfriends.

And here’s the thing—I’m also a serial monogamist, a thirty-two-year-old restaurant manager whose bedroom partners have always been serious girlfriends. Perhaps the ruthless men of the world, who dump the sweet girls and jade them for the rest of us, fantasize about relationship sex—enduring intercourse, marathon cunnilingus. The nice guys like me—I believe we fancy bold sex acts: the ones we hesitate to ask for, lest our girlfriends perceive the request, or the act itself, to be demeaning or unduly perverse.

One day last summer I found a way to fulfill my fantasy without upsetting my girlfriend in the process. It was a sizzling afternoon in early August. The restaurant was empty save for two elderly ladies who came every Wednesday for iced tea after their matinee across the street. I dismissed the bored waiters, told the bartender to shout if we got busy, and went downstairs to the office.

I needed to hire two new bartenders and three new hosts so we’d be adequately staffed when the students returned and business picked up. So my initial foray onto craigslist.org was professional, not libidinal. But, after a few minutes of reading résumés and cover letters in the stuffy office, my mind drifted. I started mulling how, with every girlfriend I’d ever had, I’d hidden my fantasy until around the one-year mark, so leery was I of disturbing a nascent relationship’s status quo. I tended to keep quiet, feigning bliss with the bounded whims of Becky, Paula, Stephanie, Elyse, and now, Katie.

In Katie’s case, I was particularly petrified because I had the feeling we were mates for life. Though we’d only been dating eight weeks, we’d already shared our desires to be parents, eventually—and I didn’t want my little need to sabotage us. I recognized the flaw in such defensive thinking—how did it help, long-term, to conceal anything? But here I was, the reluctant recidivist, concealing again, as I had with Becky, Paula, Stephanie, and Elyse. What made confessing to Katie even riskier was she seemed to like me equally. The first time I realized this was when I’d turned thirty-two in July. Within her gift, a black leather wallet, she’d enfolded a slip of pink paper with lines from Browning’s “The Last Ride Together”:

“My whole head rises up to bless
Your name in pride and thankfulness!”

There it was, in writing: An irrefutable sign she shared my tender feelings. There were other signs too—in bed, I’d noticed her eyelids shutting hard, her teeth clamping her thin lower lip. Her edgy gasps and frail fingertip gestures—I had not witnessed, or marveled at, anything like them since I was a virginal nineteen, doing it with virginal Becky.

Katie’s sweet nudges, her melting flourishes, marked an invigorating change in my sex life compared with how indelicate everything had been with her predecessor, Elyse. In fact Elyse made me want to be indelicate. It started one night at a party, when her best friend from high school, Tori, after one conversation with me, had deemed me “malleable”—and had whispered a drunken, congratulatory message to Elyse about it. I only saw them whispering and giggling into their sleeves and had no idea why. But, later that night, when we were trading party observations, Elyse divulged Tori’s secret. Our relationship plummeted after that. Things I’d overlooked—her provincial pals, her blonde mustache wisps—became irritating. And I became selfish and hurried in bed, as if to show her how malleable I could be. And, when Elyse confronted me and I refused to change, she ended it, claiming I wasn’t who she thought I was. I spent the next several months of my free time at movies and in bookstores until the night I saw Katie in jogger’s shorts in the poetry section and initiated a Browning conversation. After this chat, she asked for my number. She called the next day on her way home from school—she taught ninth-grade English—and we stayed on the phone for three hours, discussing Browning, Shelley, Keats, Yeats—everybody.

So I felt, with Katie, as if I had a lot to lose.

So I felt, with Katie, as if I had a lot to lose. And it wasn’t just the poetry or the sex or the potential parenting. It was the reciprocity.

I wanted to come on her face so badly.

I’d pictured it a thousand times: How her eyes, dark brown like wet soil, would seem luscious and lambent at the key moment, how my semen would splatter on her perspiring forehead and bony cheeks, dampen the edges of her matted black bangs. It was hard not to drift into some Katie-related reverie while reading formulaic cover letters and overlong reference notes in the windowless restaurant office with the cool air from the ceiling fan tickling my neck. Had I been at home, I’d have visited my favorite porn sites. At work, I simply toggled from the job listings of craigslist.org over to the personals. And, within the personals, I found a section called “Casual Encounters” that, before I could enter, asked me to affirm that:

  1. I am at least 18 years old.
  2. I understand casual encounters may include explicitly sexual content.
  3. I am not bothered by explicitly sexual content.

Outside the open office door, I heard the bartender, Luke, milling about and sighing. The heavy magnetic door of the beer fridge wapped shut. He stomped up the steps with the bottles clinking in their cardboard cases. From the prep kitchen came the midday smells of sliced onions and cooked bacon. The head chef, Tony, chatted with our dairy supplier in Spanish about quantities of leche and crema and queso and margarina.

Secure in the fact that none of my coworkers would intrude, I entered Casual Encounters and started clicking through listings. Most of them were from men seeking men, or men seeking women. A few were from couples seeking third parties or other couples. The few ads in which women sought men were not so much personal ads—more like open calls for sugar daddy arrangements.

Still, I kept looking. At that point, it was only looking. Sure, I contemplated how jealous I’d be if Katie were “only looking.” But I ignored those feelings—it was the boredom and solitude of a slow day at work, combined with a sense that I’d earned the right to stray, based on my personal history. Katie liked me now, but how did I know she wouldn’t up and dump me after two years, to date a co-worker, as Paula had done? How did I know she wouldn’t move to San Francisco for an old flame, like Stephanie? Or decide she was too young to settle down, like Becky? And how did I know she wouldn’t dump me for the request itself? True, that had not happened yet. But the request—even when it was granted—had never been met with enthusiasm. Elyse and Paula had flat-out said “No”—both of them, when I asked, turned their backs to me in bed and, a few minutes later, after finding their panties, said something right out of the movies like, “I think I should go now.” I wound up apologizing to both of them, and—days later—our relations were restored to normal. Becky and Stephanie, for their parts, acquiesced—but I discerned the ease and relief in their postures whenever, on future occasions, I’d forego my fantasy and discharge in a traditional place. They didn’t like my fantasy. Or maybe they didn’t love me.

The last thing I wanted was for Katie to dislike anything about me—even a sole sexual attribute.

Regardless, I had historical evidence to support my fear of confessing. The last thing I wanted was for Katie to dislike anything about me—even a sole sexual attribute. And, even if Katie did prove to love me and my fantasy, even if she was destined to become my wife, the mother of my children—well, how did that prepare me to sustain yet another year-long wait, which I’d already gone through with four previous girlfriends? Wasn’t now my chance to freelance, before the time came when I’d have to notify Katie of my Wednesday-night whereabouts?

So I did some more looking. Soon, a singular woman-seeking-man ad caught my attention. It included a picture of the woman in a white bikini, and it wasn’t seeking a sugar daddy:

Hi there,

Portia is in downtown Boston. If that is good for you, call me @877/222-5694 to make an appointment. $300/hr. Hope to see you.

In the snapshot, Portia was wading in shallow beach water with the foamy light green splashing her tanned slender thighs. Her breasts—photogenic fakes, I was certain—filled out the suit. Straight blonde hair fell past her shoulders. My swift verdict: not bad for $300.

When I got home, I dialed Portia. After four rings I went to voicemail: “If you’d like to make an appointment, please leave your number and I’ll call you back.” Five minutes later she called. “My name’s Keith and I’d ... um, I’d like to make an appointment,” I stammered after we exchanged hellos. I paced my kitchen, rearranged the word-magnets on my fridge. I had hoped to be unruffled and business-like on the phone, as if scheduling a dental cleaning. But this was different—this had the potential to ruin a relationship, or incarcerate me. And all this risk, for what—my own wanton fulfillment?

“I have an hour available at eight and another at 10:30,” said Portia. Her own phone manner was rehearsed and insouciant, as if she actually were a dental receptionist. She lugged my mind from the realm of risk to the reality of timeslots. “Longer than an hour,” she continued, “it would have to be tomorrow.”

“Eight’s good,” I said, pulling a Budweiser from the fridge. I pressed the icy can to my bald, beading head, awaiting further instructions. When none came—I waited maybe three seconds—I asked: “So, where do we meet?”

She reminded me it was $300 for the hour, and said to call again when I reached the Marriott in downtown Boston. I saved her number on my cell and cracked the beer.

I was high-strung about the hazards—but also enlivened by them. The imminent adventure roused me—for, when I had no plans with Katie, I was sluggish and predictable at night—like the character in Browning’s “Householder”:

Savage I was sitting in my house, late, lone:
Dreary, weary with the long day’s work:
Head of me, heart of me, stupid as a stone:

In other words, I watched television and masturbated and pined for Katie to visit, counting the hours to our “Good night” phone-chat. Without Katie to primp for, I lounged in the same day’s boxers and dress shirt—generally a short-sleeved button-down that, on summer eves like this, became soaked in the armpits and lower back.

Plans with Portia jolted my weeknight pacing and filled my movements with urgency.

Plans with Portia jolted my weeknight pacing and filled my movements with urgency. For the first time since my frat-boy days, I brought a beer into the shower to save time. As I sipped and soaped by turns, weighing the dual taste-smell nature of the word “suds,” I pondered Portia preparations. Should I bring condoms? Yes, though she likely had a supply. How would I get there? Taxi. With rush-hour finished, it was the fastest way from Cambridge—and the least sweaty. Would I get by, sans dinner? Surely. What else did I need? Cash—to the ATM down the block for $300 plus cab fare. How would I dress? Something easy to remove, I decided, nearly spitting up my beer laughing at myself. And I knew Katie would’ve laughed too, had she heard my licentious litany in a different context—say, recited by a fictional film character or one of her male friends.

Katie. Did I still want to do this? Of course I did. “Want” wasn’t the question—my misgivings stemmed from outsourcing my want to a paid professional rather than trusting the want to my best female friend. I was a husband telling a shrink what he couldn’t tell his wife. Only I was doing, not telling. And I wasn’t a spouse, I was a boyfriend. A cheating boyfriend. Could I live with that label? Could I look Katie in the eyes twenty-four hours later and tell her I loved her?

I knew I could. For, in my heated rationalization, the chance to act on my fantasy now—as opposed to waiting one year with Katie—was distinct and separate from our relationship.

And, more importantly, Katie would never find out.

In the stuffy cab I started sweating. The air conditioning “got shot,” the driver said. I nodded curtly and gazed out the open window. It was a familiar riverside scene, for summertime—the cloudless sky, the boat-filled brown water of the Charles, bikers, joggers, dog-walkers, Frisbee-tossers, sunbathers on green grass. My armpits dripped at every red light, licking my ribs and dampening my designer T-shirt—one of those white vee-necks with the front pocket. The leather seat toasted the backs of my thighs, adhering. I kept my hands in the side pockets of my dark-green cargo shorts. My left hand gripped the thick five-hundred-dollar wad I’d withdrawn from the ATM. It was an amount I hadn’t carried since my waiter days, an amount making me wish the cab were an armored car. Meanwhile, my right hand gripped my cell phone, which I feared would tumble from my baggy pocket and get left behind in the taxi. Then I’d be unable to phone Portia once I reached the hotel, and my fantasy night would be ruined.

I sneezed twice upon entering the frigid Marriott. I had hastily pushed the revolving doors as if I were an awed kindergartener, an instant zealot of the unusual entrance contraption, eager to dash through. The lobby, all polished and glassy, felt almost windswept in its locked-in chill, a sharp climactic contrast to the oven-like ride. My moist forehead grew dry. Again, I felt inside my pockets for my cash and my cell.

I was ten minutes early.

I feared I was an object of suspicion—as if the grinning doorman, the uniformed bellhops, and the red-capped concierges could all determine in a glance that I was not a guest of the Marriott but a misdemeanor-in-waiting. Through the carpeted foyer I found a meeting area with dozens of empty black leather couches. I sat beside a clear glass coffee table, on which there lay crinkled copies of the Wall Street Journal, New York Times, USA Today, and Boston Globe. After dialing Portia I picked up the Journal, only to drop it when she answered: “Is this Keith?” she asked.

“I’m in the lobby,” I said. “Sorry I’m a little early.”

“Are you alone?” she asked.

“Yes.”

“I’m available now,” she replied. “Come up to room 1719.”

At her door I stared at 1-7-1-9. Each digit was an italicized silver figure, slender and slanted with pointed edges, fixed to the door by small screws. It was the type of font you might find on any hotel door. But, for me, the four digits were poignant and iconic, a quartet of symbols I knew would last in my memory because of the occasion’s rarity. All these months later, I recall the diagonal slope of that seven as clearly as the curve of Portia’s spine. And I remember, too, how—in my hesitation—I found apt meaning in the 1-7-1-9: At seventeen I got my first blowjob, and at nineteen I lost my virginity with Becky.

I thought of Katie again before knocking. I was cheating on her.

I thought of Katie again before knocking. I was cheating on her. There was no gainsaying that. But it was pleasure for pleasure’s sake—life was short, and she’d never find out. I reminded myself that I was a thirty-two-year-old man and unmarried at that. Maybe when I was sixty-four and married, I’d be content to spend my summers sipping iced tea and attending matinees. Yes, that might pass for revelry at 64. At 32—wasn’t I supposed to be running red lights and pissing on walls? Wasn’t I too young to be a malleable life-mate?

I knocked.

“Who is it?” said a now-familiar female voice behind the door.

“Keith,” I said. “Your eight-o’clock.”

I heard a few clicks. She opened and peeked over my shoulders, leaving the chain attached. She quickly unlatched it and ushered me within. In the dim room the only light came from the hallway and a shaded desk lamp beside which sat an open laptop. Otherwise, it seemed like a typical hotel suite, with a tightly made queen-sized bed, a cabinet-encased television, and a small couch. “Nice to meet you,” I said, and we shook hands.

“You’re young,” she said. She kept her left hand on the open door. There was a golden wedding band on her ring finger. Her face resembled the Portia of the photo—tan and taut at the cheek bones, long blonde locks. Her upper thighs, in their tight denim cutoffs, were thicker than depicted, but I couldn’t complain—I liked what I saw, especially the spherical breasts in the tight, white, low-neck tank-top. Her cleavage struck a thick black line, a shadowy stripe between piano keys.

She was older than she appeared in the photo. Even in the dimness, I discerned laugh-lines on her face and crow’s feet by her eyes. But I didn’t care. In a matter of seconds, I sized her up physically and knew my desire was there. Perhaps because I was a naive first-timer, I was touched and flattered at her declaration that I was young—I didn’t realize she might have said it without believing it. For I was completely bald and, at six-four, on the tall side—no one ever seemed to think I was young. My hairline had begun receding in my early twenties. And, through the years, I’d seldom been carded when buying drinks. “I’m not that young,” I protested.

Her hand stayed on the door. I heard the electric thrumming of her laptop and the gentle whoosh of the air conditioner. “Well, before we get started, do you have any ID on you?” she asked.

“None,” I said. All I’d brought was the cash.

“I just want to make sure you’re not a cop,” she said, smiling. Her small teeth were perfectly aligned and her thick lips pink and glossless. “You’re not a cop, are you?” she asked.

“No,” I said. I wondered if Massachusetts law obliged police to reveal their identities, if they were asked.

“I’m just paranoid about getting busted,” she said, shutting the door. She flicked a light in the bathroom, which was on the left as you entered. “First time?” she asked.

“How’d you guess?” I said.

“I could hear you standing in the hallway,” she said. “Well, Keith, let me tell you about how I like to do things. First, you’ll find soap and water in the bathroom, and you can wash your hands. There’s also toothpaste and a toothbrush. But, before you clean up, I just need to make sure about money. It’s $300 for the hour. If you could put your money on the desk, right by the computer, I’d appreciate that. Do you have any questions?”

I shook my head and put my fresh bills on the table.

My reflection in bathroom mirror made me feel older than thirty-two.

My reflection in bathroom mirror made me feel older than thirty-two. My face was a landscape of crisscrossing creases and my forehead was wan and line-streaked. My nose floated between two parentheses, sideways arches from which my cheekbones protruded. Who was I to be remarking on crow’s feet and laugh lines?

Then again, I wasn’t charging $300 an hour.

When I came out, Portia was standing hunched by the desk, typing on the laptop. My cash was still there. “I’m setting up tomorrow’s appointments,” she said without looking up. “Make yourself comfortable on the couch.”

I suppressed an urge to mention that she could email on her own time, not mine. “How long are you in town for?” I asked, once I sat.

“Till Friday,” she said. “I come up two or three times a year. If you enjoy tonight, I can get your email address and let you know the next time I’m in the area.”

“Where do you live?” I asked.

Florida,” she said, joining me on the couch, inches away, facing. “Don’t ask where in Florida. I don’t like sharing too much, for obvious reasons. Besides, I want to learn more about you,” she added, brushing my bare knee with her palm. “What’s a tall young man like you seeing me for?”

I shared my fantasy, including specifics of how my girlfriends had reacted to the request. She nodded and smiled, as if she’d heard it a thousand times, or as if she’d expected worse—whatever that was. I felt tamed. And I now felt that Katie’s predecessors were tame, too. Really, was a little splash in the face such an affront? Was it so far afield, considering all the favors a man could seek? If they had loved me, wouldn’t my girlfriends have wanted to do anything I’d ask for? Or did love, too, have its limits? And what were the limits? Pissing and defecating on your lover? Whipping and asphyxiating? Could you sincerely broach these topics with a spouse, your life’s lasting love? Or were these selfsame subjects the reason Portia came to Boston three times a year?

All I know is, Portia heard my request and grinned. She made me feel like I was about to become the easiest $300 she’d ever made. “So—I guess—that’s probably one of your milder requests, right?” I stammered.

She shrugged. No response. It was as if she feared I’d change my request if she revealed the tame truth about it. She sat Indian-style on the couch and looked directly into my eyes like a doctor about to deliver some serious news. She finally spoke. “Well, Keith, we’ve got a full hour,” she said, her tone dry and prognostic. “If you like, we can do what’s called an RGE—a real-girlfriend experience. We would talk on the couch for a while, start out with foreplay, and slowly remove each other’s clothes. And when you’re ready to go deeper, you just tell me.”

“Okay,” I said. I glanced down at her toned thighs in their tapered cutoffs. My raw physical attraction persisted, stiffening. But I couldn’t bring myself to kiss her—yet. I touched her thigh and she held my hand to it.

“It’s okay, Keith,” she whispered, and I was relieved, for it seemed like my RGE was underway. She arranged herself so that she sat behind me, her legs surrounding mine, her breasts on my back. Her fingers kneaded my neck, probed the tense nodules of my shoulders. “What do you do for work?” she asked.

For several minutes I rambled about my career and workday, eventually segueing into how I met Katie, while Portia massaged and pressed with rudimentary questions—“Do you like working there?” “Does Katie want children?”—At length, I leaned back, turning to kiss her full-on. But she kept her lips closed, even when my tongue pressed. Her hands were active though, and with a strong, skilled palm she rubbed my crotch—such alacrity, here the palm, now the fingers. I feared I’d never endure for my fantasy. Her other hand caressed the small of my back, my buttocks. My eyes were shut for a while. Then they wandered the dim room—the laptop, open and thrumming; my money beside it; the open bathroom door. She undid my belt and I shut my eyes again. “Let’s go to the bed,” she whispered.

On the bed we fondled and kissed, our clothes still on, her mouth still closed.

On the bed we fondled and kissed, our clothes still on, her mouth still closed. “How come you don’t kiss?” I asked.

“I have a boyfriend back in Florida,” she said. “He knows what I do. He understands it’s a job. I won’t kiss other guys, though.”

“You must think I’m a bad boyfriend,” I said.

And why did I care what she thought? I don’t know—but it meant a lot to me. Perhaps it was part of wanting an RGE? Perhaps we humans—or the sensitive ones, like me—prefer being liked by our lovers—even the professional lovers. Either way, I felt wounded when Portia didn’t reply. For the first time in maybe fifteen minutes, we were neither groping nor chatting. And, as if she were my girlfriend freezing up, I moved to reestablish our halting rapport. I clasped her left hand, thumbing the golden band. “Boyfriend? Or husband?” I asked.

“We’re not legally married,” she said. “But we live together. He’s my daughter’s father.”

“How old’s your daughter?” I asked.

“Keith ... I’m sorry, but it freaks me out to answer questions,” she said.

“I’m sorry,” I said. I sat up on the bed. Had my life been a movie, this might have been the moment when I rose righteously and declared, “I can’t do this.” Fidelity would conquer greed, morals would defeat smut. But my loot was on the table and, more than that, I remained attracted to Portia’s face and physique. Sure, we had different definitions of an RGE, but what did that matter? We were in bed together. Her hand had rubbed my crotch. The ice was broken. It was time to act like a paying client, rather than a dumbstruck rookie. In a restaurant setting, it was easy for me to be a boss when I was employing people to perform. Why not in a dim hotel room? I pulled off my shirt and, as I unbuttoned my shorts, I asked, “Do you have condoms?”

She rolled onto her slender side and reached for the bedside drawer. Without another word from me, she sat up and pulled off her tank-top. Now her breasts appeared overlarge for her frame, dwarfing her bony ribcage. But they still enticed me, and I reached for them immediately. I tongued her left nipple and it grew stiff, a fact I wanted to attribute to my skill and appearance rather than to the air conditioning. The wrapped condom remained in her palm. I hastily pulled off her cutoffs and panties. She was completely shaven. I turned her over, just to get a good look at her muscular ass, then I lay on my back. “I want you to blow me for a few minutes,” I said. “Then you can put the condom on me, and mount me. When I’m ready to come, I’ll tell you. You remove the condom and I’ll finish on your face.”

“I don’t do oral without a condom,” she said.

“Are you serious?” I exclaimed. I was hard and steamed—and subordinating my libido to her health seemed like an outrage. I sighed. Would she have insisted on such precautions with a veteran client, or one who didn’t seem so damn harmless?

“This is my livelihood, Keith,” she said. “I have to be safe.”

“This is my livelihood, Keith,” she said. “I have to be safe.” I heard the faint tearing of paper, then crinkling. She held the base of my prick and placed the unwrapped condom at the head. She unrolled the rubber slowly, pinching the tip. Then she began, her warm lips surrounding my shielded shaft—up down up down, squeezing, gliding, licking. She knew exactly what to do. Yet a consequence of her skill was a discomfiting detachment, felt in the metronomic efficiency of motion. Only through repetition and practice could anyone get this good—and so dryly automatic—at anything.

And, strange to report, I found myself likening her rehearsed adroitness to the imperfect savoir-faire of my restaurant employees. For example, Luke, the bartender, often undermined his exemplary service by sounding too canned when bidding customers farewell. “Have a marvelous day” was his favorite inauthentic signoff. And every now and then he’d draw my reprimand. “Luke, they’re tipping you not to make it seem like a job,” I told him, on more than one occasion. Luke had been serving, rather than tipping, for so long, that he struggled to comprehend—customers paid for an illusion of individualized attention, and didn’t appreciate it when our staff failed to fake the requisite passion.

But Luke still got great tips because he was, on the whole, a great performer. And the longer I lay back and savored Portia’s performance, the more I found myself struggling to focus on larger questions—here musing, now blanking, here moaning, now my hips moving in unwitting rhythm with her head. Her impersonal flourishes ceased to bother me and became an acceptable by-product of her overall excellence. Her lips clamped so tight, her tongue pressed so hard, her mouth generated so much heat that I well-nigh forgot I was wearing a condom. I shut my eyes. I didn’t know how much longer I could last. I tapped her shoulder, hoping she’d recognize the tap as the signal to switch from blowing to fucking. But she kept on with her warm mouth for another few seconds, as if by finishing me then she could avoid fucking me later, or avoid my dream ending. A part of me wanted to relent, but I had come here for a purpose and in her ignoring of my tap I grew resolute. “Okay, Portia,” I whispered, tapping her shoulder again. I held her shoulders and coaxed her head toward mine.

With her on top of me, I mashed her breasts together and gripped her ass. I stuck my thumb in her mouth and she sucked and bit lightly. The intercourse itself, though, felt like typical sex with a condom—it was watered-down liquor when I was used to Scotch, an indoor pool when I was used to the Atlantic. It might have seemed blissful when I was seventeen and had no gauge for salacious thrills. It might have been splendid, too, if I’d been in the midst of a dry spell. Not that fucking Portia was rote and listless—it was still screwing, still sensational. It just wasn’t what I’d grown accustomed to lately: Katie grabbing my ass in all the right places as her wetness surrounded me. Yes, Portia knew how to move her middle—but I wasn’t coming any time soon. My eyes drifted around the room again and settled on my $300. “Want to try another position?” she asked.

“Just blow me again, real quick, and then I’ll finish,” I said. She went back to work. When the time was right, I whispered, “Okay,” and she slowly, gently, removed the condom.

I moaned a rapid succession of soprano shrieks.

And so I arrived, at last, at the big moment. I kept my eyes closed and stroked myself gradually, then rapidly, as if I were in my own bedroom, as if no one were watching. Becky, Paula, Stephanie, Elyse, Katie—I was about to do with Portia what I’d seldom done with the five best female friends I’d ever had. If my life were a movie, then this would’ve been the juncture for opining on why it was easier, sometimes, to share fantasies with strangers than with intimates—and why we humans often rely on pornography or outsiders for thrills. But, in truth, this moment—on my back in a whore’s hotel room—was bereft of philosophizing. In those precious seconds prior to orgasm—an orgasm I knew I’d remember forever—I emptied my mind of analysis and thought and cleared my brain for the buildup of pleasure. A few strokes before I burst—right when I knew I was on the verge—my breath grew short and quiet, and I peeked to make sure Portia’s face was still there. I burst. My tip throbbed with wrenching spasms. I moaned a rapid succession of soprano shrieks. My load splashed the bridge of her nose and sprayed her lips. She held still for it all, all ten seconds or so. As I came and came, I closed my eyes again and thought about all my ex-girlfriends—Becky, Paula, Stephanie, Elyse. I wished I could come on their faces, figuratively declaring “Take that,” for cumulatively taming an honorable beast like me, to the point where he feels he has to offload his carnal thirsts on a stranger like Portia. I watched Portia drying her face with her tank top. And now the room was quiet again but for the laptop and air conditioner. Portia kept flipping her shirt around, searching for a dry part, rubbing her cheeks again to see if she missed a spot. I wished I could finish on her again and make her ruin another T-shirt. I wished I could come again and again on the faces of my exes, until they used their entire wardrobes drying themselves.

When Portia got up to find a robe, I reclined on my elbows, naked on the bed. My mind remained lost in thought, vengeance, but I was bodily tranquil, sedated. “You really do give great head, Portia,” I said, as she knotted her waist-string.

Por eso me pagan,” she said, grinning. “That means, ‘That’s why they pay me,’ in Spanish.”

“I knew that,” I said. “Lo sabia. You pick up a phrase or two, working in restaurants.”

She nodded. “So, want to give me your email?” she asked. “I’ll probably be back again sometime in October. Right before it gets too cold.”

She offered me pad and pen. As I wrote she went to the bathroom, emerging with a glass of water. I was still naked on the bed. “I hate to kick you out, but I have to clean up for my 9:30,” she said.

I left pen and pad on the bed and dressed. We said goodbye with a handshake at first. And, when I leaned in for a kiss, she gave me her cheek.

In the bright hallway I stared at 1-7-1-9 and envisioned adding “32” to the numerals—the age when I finally had a one-night stand, finally fucked someone who wasn’t my girlfriend, finally managed—in some measure—to do exactly what I wanted in bed, without worrying about whether the request would ruin a rapport or hurt feelings. The orgasm was superb, certainly, but what I savored about the night, then and there, was the privilege of uttering commands like “Blow me,” of telling a woman what you wanted and getting it.

During the air-conditioned cab-ride home, I pressed my forehead to the rolled-up rear window, and again observed the riverside, this time from the opposite side of the road. It was dark out now. And, in the starry black sky, there hung a colossal moon of lava-like orange, a few slivers short of a perfect circle. A few bikers and joggers remained, visible thanks to their nighttime gear, which seemed to capture, fleetingly, the light of the moon and the lampposts that lined the street. I leaned back into the soft leather seat.

My deepest conclusions were sadly obvious: orgasms calmed a man. Nighttime views and climate-controlled taxis helped a body relax.

In vain I searched for meaning in the day’s events. I wanted to find some lasting lesson, some profound kernel, in the marked easing of my mood from the first cab ride to the second. But I resolved nothing. My deepest conclusions were sadly obvious: orgasms calmed a man. Nighttime views and climate-controlled taxis helped a body relax.

And so it seemed to me that I’d gone whoring for the first time in my life, yet all I’d gleaned from the outing were routine facts. I told myself I needed time; that a night of sleep would clarify the episode. And, if it didn’t, surely the weeks and months to come would yield acute truths. Again I stared out the cab window at the bright moon and felt the air conditioning on my cheek as I shifted in my seat.

I wasn’t nervous about seeing Katie. I knew she’d never detect my indiscretion. Not that I’d grown guiltless about betraying her. But I was confident I could hide the guilt, mainly because Katie had no reason to suspect it. For, even if she’d spontaneously visited my apartment and found me strangely missing, and even if she asked where I’d been, I could have told her, “I went to see a whore,” and she’d have laughed out loud. She’d never have believed me capable of such a thing.

On the ride home, I could scarcely believe I’d done the deed myself.

As it turned out, Katie never asked where I’d been and I never told. The next time we chatted on the phone, we picked up where we’d left off, discussing the destination of our first major trip together. My preferences were England and/or Italy, where we could visit all the places Browning had written about. We wound up going to London over Labor Day weekend.

Did I long to go whoring again? Absolutely. As the weeks and months passed, I realized I wished to go whoring for the same simple reason most men had gone whoring through the ages: a ceaseless desire to shunt your sexual selfishness onto someone who was paid to ignore the greed.

I felt tempted when I received Portia’s follow-up email in October. But I knew I wouldn’t succumb. For, by this time, Katie and I talked every day and slept in the same bed most nights. In other words. I’d have gotten caught. I wish I could report that my love for Katie was so irrevocably intense that paying for Portia was out of the question. The truth is, my love for Katie was so irrevocably intense that paying for Portia was a valid question. For I still had not confessed my fantasy to Katie. And now, more than before, there was way too much on the line to risk doing so—we’d planned to meet each other’s families over Thanksgiving. I longed for Portia—or some other whore—to fulfill my fantasy yet again. The only thing that stopped me—detestable though I may be for admitting it—was the fear of getting caught.

I can hardly be the only devoted partner in the world harboring a sexual secret.

If that’s reprehensible, so be it. Perhaps such me-first solipsism is how the male mind works, when it comes to sex. Or, at least, that’s how my male mind works. And can you blame me for closeting my fantasy, or hiding the one time I went whoring? I’d waited my whole life to find what I’d found with Katie. Why wouldn’t I lie like a coward, if the truth might rob me of what I’d always wanted? Think what you will about faith and trust and honesty between partners. I was faithful and trustworthy and honest with Becky, Paula, Stephanie, and Elyse. Where did it get me? A lasting relationship takes pragmatism too—strategic discretion about what to share and what not to. I can hardly be the only devoted partner in the world harboring a sexual secret.

If anything, I’ve remained content to have gotten my turn with Portia. Some men and women may believe that by aggressively acting on a fantasy, you lose the charm of coincidence, the joy that might come by laconically letting fate and destiny bring the dream to you. But I know better. And there are still times, when I’m fucking Katie, and wishing so badly I could finish on her face, or express my desire to do so, that I console myself by thinking back on my night with Portia, even if my clearest memories of it are the narcissistic meaning of the numerals on her door, or how comfy and relaxed I felt on the air-conditioned ride home, gazing at the moon, grateful for the artificial breeze caressing the side of my face.


 

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