Jack and Jill

Senior year in high school. One day my best friend tells me about this girl he met who I “had to meet.” I was somewhat popular, at least with the large nerdy population of my school and I’d thought I’d met everyone, but apparently this girl Jill slipped past my radar. After he mentioned her I kept hearing about her though, this brash, blindingly intelligent poet, lesbian, activist. Frankly it was starting to get annoying. Who was this chick?

A month later I found myself cornered in my best friend’s kitchen. He presented us to each other, like some landmark meeting of the minds. I suppose we were both sort of big personalities so everyone wanted to know how we would react to each other.

We eye each other. We circled each other. We asked some pointed questions about books and music. We fell into banter. We sat down on the floor and started a long conversation. We sang some songs. We tested each other. Eight hours later we were best friends.

That’s how it went in high school. I had this close group of friends and we all dove headlong into this incestuous relationship somewhere between friendship and something more. Every moment was swooning over an intellectual crush or a sexual one or trying to figure out which was which. Everything was blurry lines and cuddle piles.

Months went by and Jill and I talked every day. We talked for hours. We talked about everything. So At some point I fell in love with her. In some ways it was the first time I fell in love, or at least the first time I fell in love with someone for more than physical or situational reasons. It was confusing and weird and awkward and wonderful.

Jill mostly dated girls, seemed to have a crush on my friend Lindsey, but very obviously had a crush on my best friend Martin. Lindsey had a crush on Martin as well, but Jacob had a crush on Lindsey. No one had a crush on me, or at least not that I knew of. This was the way high school was.

So That summer I decided to seduce Jill.

Jill and I, more than any of our friends, had the most in common when it came to music and literature. We were also both writers, where most of our friends were musicians or artists. We talked about stories we were working on, we obsessed over poetry, we locked ourselves in her room and listened to The Doors. We were angsty and horny and we though we were so very deep.

This was the first time in my life I became aware of the changes that came over me when I wanted someone. Later on I would realize that this was my form of seduction.  I take someone apart, find their buttons, find out what they want, find out what they like and then I become that as much as I can. I figure out the puzzle of their desires and then I show it to them, tempt them with it until they ask me for it and think it was their idea. That’s how it works.

I’m not sure how that worked in my teenage mind. I suppose I thought since she liked women I would be more emotional, more vulnerable, chatty and catty and soft. I wasn’t very subtle,. I started listening to Melissa Ethridge and telling her how I had a gay Aunt and how I identified with her “so much.” It was silly and juvenile and she saw through most of it.

Still one night we laid in her bed and I massaged her back and traced little patterns on her arm with the soft pads of my fingers. I touched her so lightly that we could feel my fingerprints flutter across in the tender insides of her elbow. Her eyes closed and my touches grew bolder. I traced up her leg and across her belly and even circled the dark outline of her nipples through her shirt. I moved closer, not sure if she was asleep and kissed the side of her mouth.

The next day she gave me a letter. She asked me if I thought she was asleep. She asked me if I liked her circle-yes-or-no. She quoted songs. She showed interest.

I really wish I had a copy of the letter I sent as a reply. I don’t remember it all but it was long and it was as eloquent as I could muster and in the end I told her that I loved her and that I wanted her in my life in any capacity, but she needed to know. I told her that I wanted her and that I needed her and that she was amazing.

We met at Martin’s house and we stood on the porch shyly. She asked if I meant it all and I wrote to her. I did. She asked if I was going to kiss her and so I did.

And my heart exploded in fireworks.

We fell into the a strangest practice. You see, We were sexual people. We liked to kiss and we liked to touch, but we were also scared and awkward and dramatic. Plus there was the fact that neither of us was really sure she liked boys. So somehow we ended up going back to her room every day after school and I fooling around and I would always end up going down on her.

You see, Jill was pretty comfortable with her body. I on the other hand wasn’t comfortable with mine. She didn’t seem to mind this because she really wasn’t sure what to do with a penis. I liked making her feel good; in fact I loved that it. Plus she was multi-orgasmic.

So it came to be that for part of a school year and half of a summer I would go over her house every day and we would make out and then I would go down on her for an hour or two. I don’t mean this facetiously or even proverbially; it was literally between one and two hours.

Initially she showed me how she liked it. She told me where to lick and where not to lick and when to go slow and when to go fast. Once I knew the basics I improvised well and soon my world became the incense she burned and the light smell of her sex and the tuft of blond hair and her thighs closing around my head and her hands in my hair and the power rush I got from making her come over and over again. Sometimes it was twenty times in an afternoon.

We tried other things, sexually. She occasionally, awkwardly, reached into my pants and toyed with my penis. She didn’t seem into it and so I wasn’t very interested. We even tried PIV sex, but she was super tight and didn’t like penetration particularly and it ended up being painful for her and weird for me. Really I just wanted to eat pussy all the time. Honestly, I still do.

The physical part of our relationship was lovely, if a bit unorthodox. We had conversations about love, art, poetry, literature, philosophy for hours on end. We hung with our friends, life was good.

Until the walk.

We were walking one day, holding hands and some of her other friends were down the block. Her queer friends. She immediately dropped my hand. I didn’t really think about this at the time, but it stuck in my head for days after. There were other ways I was segregated from parts of her life. We both had a lot of friends in various cliques and so on. We were social butterflies and social chameleons. There were very clearly parts of her life in which I was not welcome.

I was living Chasing Amy.

The insecurities started there and grew and by the end of the summer we were broken up. From then on we were on and off friends and eventually when I started college as she finished up high school I was on my way to becoming an angry young man and deemed her an undesirable.

Still I think about her a lot and that Summer remains this strange defining moment in my life. It was when many of my curiosities about sex were addressed and the desired that were building inside of my teenage mind finally got acknowledged.

And ever since I’ve told people I was trained by a lesbian.

4 thoughts on “Jack and Jill

  1. I’m really into backstories, so reading these posts about your sexual beginnings has been enlightening.

  2. I’m really into backstories, so reading these posts about your sexual beginnings has been enlightening.

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