Jessica's Pussy
Short story | Fiction | 23 min read
A friendship that began with army men and a trampoline kiss stretches across two decades, narrated with crude humor masking real tenderness. The narrator tracks his fascination with his best friend Jessie through grade school games, a near miss in high school, and a reunion at her wedding that tests what they've always meant to each other. What happens in her childhood bedroom hours before she marries someone else becomes the story's reckoning. Contains explicit sexual content, drug use, infidelity. "That was me and Jessie's last play date"
I had been interested in Jessica's pussy since about the fourth grade.
But I never called her Jessica.
She was always Jessie to me.
So this story should really be called Jessie's Pussy but that's too similar to Jessie's Girl which I think is a song so I call the story you're about to hear Jessica's Pussy and it is, as you might imagine, all about Jessica's pussy.
The first thing you need to know about Jessie's pussy is I never got to have it. Other guys did. A lot of other guys did, starting, for her, I think, in around the seventh grade. Jessie gave her pussy to them. She never gave no pussy to me.
They were the men's volleyball team, the soccer players, even the theatre geeks if they played a prominent enough part in one of our school plays, which was dumb shit like Guys and Dolls, but, look, if you were one of the main Guys in Guys and Dolls, Jessica gave it up for you. I don't think she ever fucked any of the guys in West Side Story, which is too bad 'cause that's a much better musical. And if you're thinking I'm trying to indicate I'm gay by making comments on which musical is better, Guys and Dolls or West Side Story, grow up—West Side Story is obviously the superior musical.
So to fuck Jessie's pussy you had to stand for something.
And I didn't stand for something.
You know how they say familiarity breeds contempt? Well forget that 'cause that's a bullshit phrase—doesn't mean anything, doesn't have anything to do with this story and I never should have typed it. Fuck backspace.
In the first grade Jessie and I did things like cut each other's hair—well, I cut her hair (she asked me to) and when my mom saw it she sent Jessie home right away and called Jessie's parents to warn them about what they were about to see walking through their door.
It wasn't that bad.
I've cut lots of girls' hair since then and I never would have had the confidence that I do today if I hadn't had that first key experience cutting Jessie's hair. It wasn't that bad.
So that was first grade. Technically my first kiss was in the second grade with Jessie on her trampoline. My sister was there and she tells the story that we bounced and bounced and bounced and on that third and highest bounce, Jessie and I kissed each other in mid-air, lip-to-lip, like fucking astronauts. And that is pretty much how I remember it, too. Jessie and I have always been operatic best friends. If I was going to blow up with someone in a space shuttle..Jessie, definitely, hands down.
By the third grade—second grade maybe—Jessie and I had given up on kissing in mid air and exploding in NASA rockets and we were into strategy war games, mostly. I would go to her house where she had bags and bags of these little green military men—
Look, if you're just reading this story 'cause it has pussy in the title, you should probably find something else to read, bro.
—and we'd set up these military men all over her room, her on the side with the bed, me on the side with the door, and the idea was that eventually we would have a war. You know, rubber bands and shit, we'd shoot down each other's guys. But that never happened. We spent so long setting up the guys and creating terrain out of her shoe boxes and dirty clothes and making sure that each of us had the most superior tactical positions possible!—that we never actually got around to shooting each other's soldiers down. My mom would call for dinner or her mom would call for dinner and I'd be like:
"Do you want me to help you clean these up?"
And she'd be like: "No."
I don't think we ever had a single fight. We just worked on our strategic positioning afternoon after afternoon after afternoon and then I imagined Jessie cleaning up hundreds of military guys, all in different positions, each with a different weapon, in this war between us that never turned into a war.
So where was I? Oh yeah: Jessica's Pussy. I'm just going to call it Jess's Puss from here on out because I know your time is valuable.
Jess's puss was of infinite fascination to me starting around the fourth grade. I mean Jessie and I were like BFF material, riding Hot Wheels, living like two doors down from each other. So sometimes I'd be in Jessie's room and she'd be changing to go to the swimming pool.
Jessie didn't have a swimming pool but her eccentric neighbor Candy did. Candy is another fucking story for another fucking time.
Jessie would go in her closet, which had sliding doors, and she'd push off her shorts and her little girl panties and she'd put on her one-piece and it had this gusset and from where I was sitting on the floor I could see up between Jessie's butt cheeks and her legs and I could see her little pussy from the back and then she'd pull up the one-piece and her pussy would snug itself against that gusset and then we'd go swimming but the whole time, whether Jessie was diving off the diving board or pretending the plastic snake was real and screaming, "Snake!!!" loud enough for the whole neighborhood to hear, I was thinking about Jess's puss.
Nothing could take my mind off it.
Even eccentric Candy, who was single and rich and ate with a table full of non-sexual blow-up dolls—even Candy couldn't take my mind off Jess's puss. The way it snugged into that gusset, the crack between the lips of it clearly visible through her one-piece. I wanted to touch it, lick it, suck it, fuck it, from sometime around the fourth grade. That's when my innocent curiosity of it became a basically adult wanting of it. I was always trying to work up the nerve to touch her there, surprise her on the edge of the diving board, just put my hand between her legs and let her know I wanted her and her pussy to..well..to basically be mine.
Cut ahead 14 or 15 years.
Now Jessie is 24. I'm 24 as well. Jessie is getting married.
She invites me out to dinner to discuss her wedding plans.
We have sushi. This is just me and Jessie, without her husband, Jon, who doesn't come in until later. If you're excited to meet Jon, you'll have to hold your horses.
Jessie takes a full year to plan her wedding. She uses a three-ring binder with insert sheets, color-coded tabs, multi-colored markers, gel pens, regular pens, Polaroids (yes, this was before the age of the digital camera, but let me assure you, we did have pussy back then)..anyway Polaroids of locations, flowers, flower arrangements that looked like flower arrangements she actually wanted to use at her wedding. It's sort of like..imagine if..well I know this is difficult but imagine a world without Pinterest. Imagine if there was no web, and you had to do everything on Pinterest manually. That's what Jessie's was doing.
The binder was three inches thick.
It was comprehensive.
It contained movable construction paper models of the seating configuration. It was not only important to seat the right people at the right tables, she told me, but also to position the tables correctly with respect to each other. There was likely to be eye contact between guests at adjacent tables and that, too, would affect the conversation. Seating dynamics are very complex for weddings. I think that alone is reason enough for me to never have one.
But I sat and listened to Jessie's plans. And not just because I wanted to get in her pussy—I really cared, I was her friend her whole life, I was happy she was getting married and Jon was cool. I mean he was like highly educated and shit; that's the type of thing Jessie needs. She's kind of a non-practicing intellectual, as in: she drinks and smokes and swears and says that she'll someday write a book. She paints on canvas in cemeteries. She gets The Big Lebowski. So, like I said: basically a non-practicing intellectual. But fuck intellectuals anyway.
If you're just reading this story because you're an intellectual, please stop now. You're as unwelcome as the pussy-only crowd.
Who's left? Just us crows.
Right so Jessie and I would drink on these excursions, too, ok, so we're like gorging on sushi talking about her wedding plans and The Benefits of Natural Parenting—I'm pretty sure that's an essay title so we're gonna treat it like one. And afterwards it'd be freezing cold and I'd be wearing nothing but a hoodie and Jessie would have this all-wool, Little Red Riding Hood head-to-knee jacket which was appropriate for the climate we were in, which was Ohio. At the end of these nights it would invariably be a full moon—fuck you, alright, it was always a full moon, this is my short story, go write your own. We'd be in some alley on Fifth Street smoking endless cigarettes, buzzed and knowing that we always wanted to and could do so at any time, right now, boom, Jessica's Pussy—story's over. But we never did. Neither of us made a move. I can't speak for Jessie but I don't usually fuck people who are planning weddings, like, with the person they want to spend the rest of their life with. Some sex is just sex—but that sex is not just sex. That sex is like potentially life-changing sex where you end up in the movable seating chart sitting next to the bride. And, Jessie always knew that she was going to have children and I always knew that I was not. So. I never wanted to get married, either, and she always did. So.
I'm in my apartment. There are all these people sitting on the floor and lying on throw pillows. We've been up all night. We've been to the park. We've been hanging out on Fifth Street. We've been talking to cops on horseback. Well, I was talking to cops on horseback. Why? Because talking to cops when I'm on ecstasy is one of my favorite things to do.
Then I remember.
Today is Jessie's wedding.
There's a drum circle going on in my living room and my downstairs neighbor is banging on her roof with a broom handle. I vaguely wonder why she doesn't just come upstairs and ask us to be quiet.
I stand up.
Everyone lounging looks at me like I've broken some sort of unspoken code. Why are you standing up? You look like you're going somewhere. That involves action. That involves planning and motivation and all sorts of qualities one lacks when one is coming down off MDMA.
I say, "Today is Jessie's wedding."
Some of these people know Jessie. Some of these people have probably fucked Jessie. Some of these people I know for a fact are on Jessie's seating chart.
Excuses all:
"I don't feel like getting up."
(Yawn.) "I was just about to go to sleep."
"Yes," I say, "but Jessie and I played army men when we were kids and I have to go to Jessie's wedding! She's my best friend!"
This last part wasn't true. But she was a good friend and I know this sounds disgusting but she was a special friend. Not like the kind of special friend you keep locked in the basement electrocuted in a basin of water for torture purposes, but a special friend like you almost had sex, you've kissed a billion times, and—most importantly—you saw Pulp Fiction in the theater together on opening weekend.
That's major right there. That's bigger than Star Wars. If I had the choice of having sex with Jessie that night or her dad coming in while we were dry humping and telling us we had to leave right then to see the show..I wouldn't have changed a thing. We got off the bed and went to the theater and saw Pulp Fiction on opening weekend. That's what friends are for, and, let's face it, there's a lot of pussy out there. Why should Jessica's be so special?
It probably wasn't safe for me to drive, not due to the effects of the ecstasy but due to the fact that I was tired as hell after having not slept all night. I was that kind of lazy dangerously close to sleep, but could you imagine if the girl whose hair I mangled in the first grade and who changed into her swimsuit in front of me and who screamed, "Snake!!!!" as loud as she could got up there and was looking over the audience and her Hot Wheels captain was..just..not there?
They had it outside. I drove up to the farm. Parked in some mud. I was wearing clothes that Prince would wear if he was doing ecstasy at his own house and wanted to be fashionable but comfortable. My shirt was a shimmery purple-green thing that looked like colors were moving around it like oil on water. It was unbuttoned so you could see my chest hair. I wore sunglasses. No shoes. Honestly can't remember the pants but knowing me at the time they were probably corduroys with the widest wales known to man.
I knew some people. I knew Jessie, who was hidden off somewhere. I knew Jon as the three of us had gone out many times together. Jon would drink beer and Jessie and I would split a bottle of wine. John was a practicing intellectual. I went up to him and said hi.
"Matthew!"
He shook my hand.
"Congratulations, Jon. I can't imagine a better partner for you. Or one for her, to be frank."
I actually speak like that. I'm very formal. I say things like, "to be frank."
"Nice glasses!" he said. "Are those Oakleys?"
"No, these are thrift-store specials."
That's the type of thing I love about Jon. He has no godly idea what a pair of Oakleys looks like. He's a history major—which in case you haven't been keeping up is less marketable than a philosophy major. And yet he reaches out, trying to connect on the point of my sunglass manufacturer, having absolutely no idea that I am not a fashion guru, that all my clothes including the shimmery shirt come from the thrift store on Fifth Street, a block from my apartment. It's the only place I ever shop.
"You're not wearing any shoes!" he says.
"Well, it's such a nice day."
"Go inside, Jessie wants to talk to you. Or she said she had a gift for you or something."
"She's the bride. Aren't I supposed to have a gift for her?"
"Don't worry about it. We're just glad to see you—you never RSVP'd!"
"Oh, yeah, I ran out of stamps like six months ago."
"That's hilarious."
"Well, have a great life. I'm going to find a seat. I have to sit up close 'cause these aren't prescription."
"Didn't you drive?"
"Jon, it was kind of a late night."
"Find Jessie. I'll save you a seat."
"Are you serious?"
"Yeah, I think she wants to play you some music from The Piano or something."
"She did that like a million years ago. Grief. Did she tell you everything we did?"
"Pretty much, bro."
"That's good. Well, Make cute babies. Have a nice life, man."
"Aren't you staying for the reception? You're at the main table, right next to Jessie!"
"I know. I helped design the seating chart."
"Jessie even made a special cheesecake just for you!"
"Jon, I picked out the recipe. You know I planned more of this wedding than she did."
"Well thanks for all your help. You're a good friend to Jess. Here. See? I'll put my jacket around this chair. This is yours. Can you see from here?"
"Yes, I think so. So she's inside?"
"Somewhere in there."
"Alright. Have a great wedding. I'll be cheering you on."
Jon gives me a hug—which is not the sort of thing Jon would ever do—which is what makes what I'm about to tell you even worse.
I go inside the house through the front door, past the upright piano where Jessie's did once play for me music from The Piano. And with her slight mistakes and stops and starts it was even moodier than the original and always would be.
Jessie's parents greet me and smile and laugh and throw back their happy faces and shake their hippie hair. I could never be unhappy around Jessie's parents, not just because they created my best friend, but because Jessie's dad is the only person in Dayton who knows Japanese cinema like I do, I mean Jessie gets bored once her dad and I start talking—I'm almost more BFFy with her dad than I am with her. And it's the same thing with her mom, except with us it's novels. The woman has read everything. And, I guess, so have I.
They tell me Jessie's in her bedroom.
"The same one as before?"
They laugh.
"I'm pretty sure you remember how to get there."
So, this isn't the bedroom that Jessie and I used to play army men in, in the house that was two houses down from mine. Jessie has like five parents and three houses—I'm leaving out a lot of detail for your simplicity.
And you say, "Thank you."
And I say, "You're welcome."
This bedroom, the one I'm going to now, is the one where Jessie and I were dry humping and then instead of taking our clothes off and actually humping we left and went to see Pulp Fiction on opening weekend.
I open the door and these is Jessie, Jessica, Jess, sitting in an ergonomic office chair, her back to her desk. The desk is surrounded in poetry collages, stuff she did in high school. Jessie is wearing her wedding dress, smoking a Kamel Red, and her feet are propped up on some articulated part of the chair, the white dress pulled up over her knees, and her frilly white panties, with a solid white gusset, are staring me in the face.
"Close the door," she says.
I close the door.
"Sit," she says, pointing at her bed with the cigarette."
I sit on her bed, looking freely at all parts of her: her face, her knees, her inner thighs, her shoulders, her neck, her cheek, her crotch.
She is smiling as she says, "This is a sad day."
I mean she is smiling blissfully.
"Did you hear what I said?"
"Yeah, I heard what you said. You said it's a sad day."
Jessie sucks on that cigarette like she's trying to suck the cancer right out of it. She offers it to me.
"I quit."
"Why?"
"Because they fucking cause cancer."
"You're cranky."
"Well I was up all night doing ecstasy, and I'm so tired I can hardly keep my eyes open."
"Thank you especially much for coming, then. We never got your RSVP."
"I stopped opening mail about six months ago."
"But you remembered the date from our planning sessions."
"That's right. I do pay attention when we talk."
"Do you want to ask me why this is such a sad day for me?"
"I think I can guess."
"No, you can't guess. Why don't you take off your Ray-Bans so I can talk to you."
I think about telling her they're not Ray-Bans but then I just cut the shit and take off my sunglasses.
"Jesus, you do look like shit. Here, take this."
"I told you I don't smoke."
"I'm not asking you to smoke it. I'm asking you to hold it for me while I do something."
I take her cigarette and take a nice big drag.
"Feels good, doesn't it?" Jessie says.
Then she uses both hands to push her panties over her butt and off her cunt and all the way down her pressed-together legs and then she throws them on the bed next to me. The entire rest of our conversation Jessie's pussy is exposed. It's just: Jessie's body, her beautiful hair, her wedding dress, and her pussy, naked, legs apart, feet propped back up on the articulated part of the chair.
"Can I have my cigarette back, please?"
I take another drag and give it back to her.
"Are you still high off ecstasy?"
"No, I'm just really, really tired."
"I'm actually surprised you came."
"I would have never not come to this, Jessie."
"Did you see Jon downstairs?"
"Yes. He's saving me a seat like three rows back."
"You should be able to see well from there. Are those Ray-Bans prescription, or..?"
"They're not prescription."
"I'm gonna tell you something," Jessie says.
"What is that?"
"Jon and I have never fucked."
"Seriously?"
"Seriously."
"Why not?"
"You know," Jessie says, cigarette in mouth, "I find that why is usually not the most important question to ask."
"What question do you find is the most important to ask?"
"How."
She lights another cigarette.
"Well, Jessie, how is it that, in this progressive age, you and your husband-to-be have not fucked yet?"
"I don't know. We just haven't. What I do know is that I'm about to be married and you're my best friend and we almost fucked a million times—"
"A billion."
"What?"
"It was more like a billion."
"Alright, a billion. We almost fucked a billion times and never did and I'm asking you how you want this to go? Do you want to take your cigarette and walk downstairs and see Jon and I get married and then leave and go do more drugs with your drug friends or do you want to be sitting in that seat in the third row down there with Jon's jacket slung over your shoulders knowing that you got to have me before my husband, on my wedding day, at the farmhouse, with my sisters in the next room and my parents downstairs and Jon outside none the fucking wiser."
"Isn't that a little immoral?"
"Not until we say the vows."
"Jessie, don't you think that's kind of a technicality?"
"No. Because Jon and I have come this far. We're getting married. Nothing's going to stop that unless there's flash flood or a tornado or something. I don't see what the big deal is."
And she starts touching herself with both hands, the cigarette still between a pair of fingers.
And my cock starts getting hard.
"You know what this is?" she says.
"Yes."
"No you don't. Ask me what it is."
"What is it?"
"It's Jessica's pussy. Sounds like a short story title, doesn't it?"
"Not really. If this was a short story it should be called Jessica's pussy and why the dick is stronger than the cock and marriage will still last forever or some Fiona Apple-type shit, you know, like a one-thousand word poem that no one can pronounce because it's written in a dead language. Something like that. I don't believe you never fucked Jon."
"Do you want me to come over there and lie with you on the bed?"
"Only if we're gonna lie here like Bill Murray and Scarlett Johansson in Lost in Translation and say a bunch of philosophical shit and then at the end of the scene I'll just touch your toe with my hand and then we both fall asleep."
She comes over to the bed. Jessie kneels over my cock and she's rubbing her pussy on me through my corduroys and I'm flooded with everything that girl and I have ever been through. Maybe we should have fucked that night when we were in high school instead of seeing Pulp Fiction. If we had, we prob'ly woulda fucked a lot of times since then. I look up at Jessica. Her eyes are closed, head slightly back, hair wisps going every which way. I can't help it: my hand goes out between her legs and my thumb and index finger and the almost-webbing in between them feels the wetness of Jessica's pussy. I slide my hand back and forth a few times, taking the wetness and rubbing it on her clit with my thumb.
That's Jessica's pussy, the thing I've been thinking about since we kissed on the trampoline in the first grade, since every time she changed into her swimsuit and I saw it snug into the gusset, since she stood on the diving board and I could see that crack between her little-kid pussy lips. I'm genetically, culturally programmed to be fascinated with Jessica's pussy.
"Jessica?"
"Yes."
"Do you still have any of those old army men?"
I can feel her pussy muscles relax when she says it: "Yes."
She lifts my head by my chin.
"Is that what you want?"
I nod.
She lowers her dress and goes to the closet, cigarette between her lips. And that fucking beautiful girl pulls out two bags of army men from a high-up shelf. She sets the pack of cigarettes between us, on the side with the bed, me on the side with the door.
We chain smoke Kamel Reds.
Jessica never puts back on her panties.
And her in her wedding dress and me in my thrift store corduroys, we sit on the floor and get cancer and strategically set up hundreds of those little green military men. We didn't even have rubber bands—we couldn't have had a war if we wanted to.
We set those men up until it was Jon knocking on the door seeing if Jessie was ready and then Jessie's parents both knocking on the door asking if everything was alright and everything was "still going as planned??"
"I'll be down in twenty minutes!" Jessie yelled.
And the two of us hardly looked at each other. We did sometimes look up at the same time and we smiled, and one of our smile would ignite the other's, and we'd look down again. We chain-smoked Kamels and set up military men all over her room and we never got past the setting-up phase.
Jon was at the door.
"Jessie, would you please unlock this?"
"It's not locked," she said.
So Jon comes in and sees his future wife sitting on her knees in her wedding dress meticulously arranging military men so they'll be safe from cover in case of a possible attack.
He sees me, my back to him, engaged in the exact same task.
"Well, we're getting married in five minutes," Jon says.
Jessie lights another cigarette. With the tasty nicotine thing bobbing between her lips, her eyes looking down surveying all her military men, she says:
"I'll be down in two."
Jon closes the door.
Jessie flashes me real quick, shows me that horny, beautiful vulva.
That was me and Jessie's last play date.
When she went downstairs to get married, I stayed in her room and perfected the arrangement of my army men.
I never much thought of Jessica's pussy again.