My Three Jessicas


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Written by Isaac M. Isaac is a first-time Jewrotica writer.

[Note: This piece contains cheating. Cheating and adultery are not acceptable in any stream of Judaism and, in fact, is a serious violation that is prohibited in the Ten Commandments as well as the ethical laws for non-Jews in the world. That said, it is something that happens in our society, is part of the conversation and therefore this story is being published on Jewrotica despite some discomfort on the part of the editing team.]

Rated R

In New York, in 1988, when I was still in my sap-filled twenties, I dated three Jewish women all named Jessica in one year. Dated may not be quite the right word: had a lot of sex with is more accurate. That’s pretty much all we did. A dinner or two, some movies; but mostly just fucking.

The hitch is that I am still involved with Kate, as I have been since we left our (heavily Jewish) liberal arts college five years earlier. We have been coasting for months. We get the Sunday Times every Saturday night, and stay in reading it with Empire Szechuan cold sesame noodles for dinner followed by H&H bagels and Fairway for breakfast. We go to Woody Allen movies the night they open, and have partial season tickets to the Mets. We never moved in together, and have separate lives along with separate apartments. It is essentially over, although neither one of us is willing to actually say so, to actually start the conversation.

Kate is Jewish, too. This being Upper Manhattan, and Brooklyn, pretty much everyone is Jewish. Including, of course, our shrinks. We all have shrinks. Although the geography is more expansive, we travel by cab and subway rather than mule, and there are no Cossacks, we live in our own Anatevka with its own traditions, except instead of Tevye with five daughters, I have four women. (1) (Footnote: Yes, all their names and some personal details have been changed.)

Jessica O.

I work in casting at a downtown, Off-Broadway theater, and Jessica O. is the assistant to the managing director. She is a small town New England girl with big city desires. She has deep maroon fingernail polish that matches her lipstick, setting off her blue eyes and her curly 80s hair. She only wears tight skirts and heels, and has a luscious fleshiness from head to toe.

We joke together at work, make fun, flirt, trade the little touches on the arm. Then one night after a performance, we find ourselves the last ones in the theater after a performance. We both realize we are alone together at the same moment. I take her hand and lead her backstage. Up against the back of a wall of the set, our mouths and hands attack and grasp and move everywhere, releasing months of anticipation. I am ready to do it right here, there is even a couch on stage, and the thought of us fucking there, and then watching the show the next night, with actors whose names you would recognize sitting on those cushions, adds immeasurably to the thrill. My hand starts to slip under the waistband of her hose, and she grabs my wrist and pulls it out.

She says something about another time or not now or not here. I am in that aroused state where I don’t understand what is being said, and don’t remember exactly why we didn’t end up at one of our apartments. We live on opposite sides of town, take separate cabs. She gives me a good, deep kiss as she gets into hers.

Monday at work there is that distance; she is avoiding eye contact and I cannot tell whether it is because she wants me to go away or because she wants me to grab her and doesn’t want to show that at work.

One night, we leave the office together with a group of others. As people peel off in their various directions, Jessie and I are alone, heading for the subway. We each take the 6 from downtown, and then I change at Grand Central to cross over to the Westside. Neither of us mentions the other night. We talked a while ago about doing the crossword puzzle on the subway, how that is much better than reading. As we get on and find seats, she asks me if I have the puzzle. I do, and we start working it together. We lean against each other, talking about clues, filling in the boxes, suggesting answers, sharing the pencil. When she takes it from me, there is delightful tension in waiting to see what she will write, as she presses a breast against my arm and fills in an answer on the paper resting on my thigh. All the while, among the screech and lurch and rush of the train, with the people swaying around us, it is better than being alone.

We get to Grand Central, where I am to get off and catch the Shuttle. We keep doing the puzzle, without acknowledging where we are and what this juncture signifies. She has not invited me to keep going with her, and she has not said goodnight or “Isn’t this your stop?” The train jerks to a stop, and the doors open. I stay next to her, eyes on the puzzle. The doors stay open for what seems like minutes. She leans ever so lightly yet firmly against my shoulder. Then, the doors close, and the train picks up speed and we head toward 86th street, and her bed.

We go through the door of her tiny studio apartment, and it is immediately fireworks and insatiability. Tearing off clothes while we kiss and grope, we plunge onto her bed. She does not push my hand away this time; she grabs me and pulls me inside right away, and wraps her legs around my hips and rakes those maroon nails across my back. She is a firecracker, and delicious.

We get together four or five times over a month or two, always at her place. One time, she wants to watch me come, so she jerks me off and afterwards leans over and wipes the come all over my stomach and chest — with her breasts.

Another time, at work, she walks into my office and we pretend to talk shop while we whisper and make eyes. I peek out into the hallway and then close the door. I get on my knees and go down on her as she sits in the side chair, until she can’t stand it and slides down onto the floor. There are people talking on the other side of the wall; someone could knock at any moment. She comes, and quickly gets up, straightens her clothes. She opens the door, and says in horror, “You didn’t lock it?”

Jessica likes to use her mouth and her teeth, and she grabs and pinches. I come home after one encounter and while undressing discover a large hickey under my right nipple, the size of a dollar coin. A hickey, for fuck’s sake; is there anything more adolescent and tawdry? This is the cost of fucking someone who scrapes you with her nails and bites your nipples, no matter how good it feels at the time.

This would not be a problem, except, as you may recall, I have a girlfriend. I need to hide this from Kate. More even than lipstick on a collar, this is in-your-face evidence that is not explainable. I do not want to hurt her. I am not the guy who wants to get caught in order to get out of a relationship. But how do I hide a hickey? I have no idea how I come up with this absurd solution: With a serrated kitchen knife, I carefully scrape away some skin on the mark until it looks like, well, like a scrape – something decidedly less sexual. I concoct a bizarre yet actually plausible scenario of climbing on my desk chair to yet again fix my ancient window blinds — which I often do have to do. I really should get some new blinds for different window shapes so they don’t keep breaking. Only this time, the chair rolls, I slip, and as I fall my chest, right at the spot where the hickey is, scrapes across the sharp edge of my IKEA desktop. I tell this story to Kate, show her the wound, and she buys it. Or at least she lets me believe she buys it.

Despite the hickey incident, I see Jessica O. a few more times. The fucking itself is still fearsome, but the before and after is increasingly uncomfortable and, frankly, boring. We have run out of banter and the crossword is now just a puzzle.

Then one evening, when I am alone at my place, I feel an itching sensation in my crotch. Uh oh. I go into the bathroom for a closer look. Yup, there they are. If there is one thing more tawdry than a hickey, it is lice. The thrill is definitely gone. Plus, there is no story ridiculous enough to explain or hide this from my partner. I spend the day ridding myself of nits, washing myself multiples times, and doing several loads of laundry. There is a temptation to read a moral lesson into this, comeuppance or something. But I don’t do that. It is simply the end of those fireworks, and the end of Jessica O. and me.

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