Adventures in Virginity: Breaking up with my first grade teacher

"Ms. Shout wanted to have her way with my oversized imagination"

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Adventures in Virginity: Breaking up with my first grade teacher

I had to end the affair with my first grade teacher. Ms. Shout had taught me much, both in the ways of love and the alphabet, but we had grown apart — that, and another older woman had entered the picture.

My mother had set me up with Ms. Shout.

"Shawn said his teacher was an old, bald witch,” my mother told Ms. Shout the first time they met, then grinned at me like the petty cockblocker she was.

I wanted to head-butt her straight in the ovaries. Strangely enough, Ms. Shout wasn't offended.

“He does have a big imagination,” Ms. Shout said. Then she snuck me a covert wink, which I correctly interpreted to mean that she wanted to have her way with my oversized imagination.

Our relationship progressed like most grammar-school romances. During recess she cheered me on as I dominated foursquare with black magic tricks and won fistfuls of participation ribbons at track and field. Each time she passed my desk, she patted my head or let her ass graze my elbow. Sometimes she sat with me, pretending to help with my work while her vanilla-flavored body heat infused me. She asked me to write her love notes telling her everything about me: my favorite color, food, animal. Then she returned these letters with notes of her own written in red ink, things like, “I love pizza and penguins too!” I was smitten with her intellectual superiority — that and her boobs, which, at the size of apples, eclipsed every other girl in our class.

Had I known my cute phase was about to plummet into an awkward abyss of plastic glasses and neon jump suits, I might not have been so quick to dump Ms. Shout. But, I was young and naive. I had a thousand reasons for breaking up with Ms. Shout, all of which obscured the one true reason. I was in love with another woman. Well, woman wasn’t exactly the right word. Neither was love. I was in rabid lust over the idea of a woman. Her name was Jessica Rabbit.


Jessica Rabbit waltzed into my home in the early 1990s with the VHS of Honey, I Shrunk the Kids. An animated short, “Tummy Trouble,” preceded the film; in it, Ms. Rabbit plays a nurse who parades across the screen in a minuscule uniform while pushing a rack of milk bottles. The bottles' rubber nipples bounce like the nurse's curves. These dual milk racks appealed to both the child I had been and the man I would become.

Up until that point, I had been content with Ms. Shout's limited range of physical affection. But after Jessica Rabbit gave me a booster shot of sexuality, I wanted more. Granted, I wasn't exactly sure what "more" entailed, but I felt confident that Jessica Rabbit and I could make some interesting sexual sparks with finger-paints and my penis.

My cartoon paramour inspired in me an uneasy intensity. It was as though I had an extra bladder filled with sexual energy and no idea how to relieve it. I knew I needed to do something, but what? I tried wrestling with my My Pet Monster doll. I lay shirtless on the cold seat of the piano bench and licked the lacquered edges. I performed a marathon of high-diving bellyflops on the trampoline. Nothing helped.

Jessica Rabbit was no Disney princess. She wasn’t drawn to represent a female fantasy. She was an animated Marilyn Monroe, a busty Amazonian woman straight from the fetishistic mind of R. Crumb. She embodied a purely heterosexual male fantasy. As such, she was just as much an imaginary creature as a loquacious rabbit who walked upright.

As naïve as I was, I knew women like Jessica didn't date, let alone marry, guys like Roger Rabbit: dudes half their size who wear suspenders, who have no apparent skills or income, are clinically insane, and of a different breed entirely — unless you count the creepy relationships Hollywood princesses have with their fluffy dogs. Perhaps Jessica Rabbit was like a glorified babysitter, an escort paid to look after Roger until the final piano crashed down on him, leaving her heir apparent to Bugs Bunny's fortune.

And yet, Jessica's affection for Roger gave me hope that some woman would love me despite my rampant flaws, that my parents would not have to continue to pay older women to hang out with me when they left the house. If Jessica did love Roger, she was obviously into some freaky shit. I wouldn't even mind putting on rabbit ears or my fluffy unicorn costume if that's what turned her on.

So it was that one night Jessica Rabbit came to me in bed, strutting back and forth through the landscape of dreams. I woke sweating in the darkness of morning with my heart pounding like a primal drum to the thought of her cartoon ass bouncing back and forth. The image would not dissipate. So I did what any sane boy in my situation would do: I squirmed out of my He-Man underwear and lay naked in bed. This felt like a step in the right direction. To intensify the sensation of sheets against my bare skin, I tucked my Winnie the Pooh comforter in tight around my body. I wanted to feel as though I was encapsulated in warmth, like I had burrowed inside Jessica Rabbit’s skintight dress.

Overnight I had become a heterosexual. I always liked women, but this was something else entirely. I lay awake imagining getting hedonistic with Jessica in a bounce house and spraying the painted clothes off her with a firehose. 

My lust was tempered by melancholy. I couldn’t even pretend I would grow up and marry Jessica Rabbit the way girls my age comforted themselves with fantasies of becoming real princesses like their favorite Disney heroines by marrying Prince William or Harry. I knew too that I would never have a physical relationship with a cartoon character that would match even my mild affair with Ms. Shout. Unfortunately, this knowledge did nothing to discourage my lust. Perhaps I knew on some level that Jessica Rabbit was merely a stand-in for what I wanted in a woman the way my hands were stand-ins for vaginas. 

My lust for Jessica Rabbit was more visceral and immediate than anything I had felt for Ms. Shout. Adults often assume children's feelings are immature, that kids don’t know what true love or loss is. Kids may not understand these concepts, but they feel these emotions just as intensely as adults. Every day, children cycle through the range of human emotions, from extreme love to rage. What’s worse is that children have few experiences to qualify these feelings, to assure them that their lust for a cartoon character will eventually subside like a pesky case of morning wood. For all I knew, I would spend the rest of my life lusting after a figment of another man's imagination.

I was learning what it felt like to cope with sexual longing, to deal with a constant desire to do things that were biblically evil. I was learning that I couldn’t just lie in bed all day, lovesick for Jessica Rabbit. Life moved on. I needed to get out of the protective warmth of my bed, of the erotic escape of dreams, strap down my desires in my He-Man underwear, and walk about my days ignoring the fact that I wanted to get naked and chase every attractive girl I saw with a Super Soaker.

What I didn’t know then was how sexual longing motivates some men to develop skills that make them more appealing. Some master instruments. Others sports. Some excel in school to acquire professions that give them such peacocking feathers as wealth, status, and power.

Part of why I tried so hard in school was to please women. I wanted to be praised by Ms. Shout and all the other young teachers fresh out of college. I learned early on that creativity was a good way to get their attention. I loved how Ms. Shout smiled with carnal lust when I brought my famous imaginary friends in for show-and-tell or I built her dream house out of Legos. Creativity was my wooing strategy of choice.

So it happened that Ms. Shout asked me to stay after school. She needed me to finish a drawing of Martin Luther King, Jr. giving his iconic "I have a dream" speech. The inspirational piece was to be hung at the local grocery store, right next to the customer service desk that sold lottery tickets and cigarettes. It was a huge honor.

I sat in our classroom alone with Ms. Shout, using a rainbow of crayons to color audience members and to give MLK a sweet flattop. The classroom phone rang. Ms. Shout answered it and a short argument ensued. Her reaction told me immediately that this was a personal call. It was about a boy, and love gone awry. Perhaps my cockblocking mother was phoning to spill the news that I was cheating with Jessica Rabbit.

Ms. Shout put the phone down, returned to her desk, and started crying. I knew what it meant to cry. I did it several times a day. I didn’t know what exactly made her hurt, but I understood her feeling of helplessness.

Ms. Shout was perfect enough to be a Disney princess, to have found her Prince Charming, and yet she had found herself in a classroom with me, crying, while I dreamed of another woman. If things had fallen apart for her, what chance did I have at lasting happiness with Jessica Rabbit, or a real woman for that matter? I began to cry. I cried over the prison of youth, over the years I would be confined to my juvenile body, unable to act on my adult feelings. We cried because we could not make the real world reflect our interior lives. We cried knowing our need for love and affection would never fully be satisfied.

My tears provoked Ms. Shout to throw her arms around me. She shook slightly in my arms, convulsing with pain and laughter. She knew that this feeling would pass, perhaps, and that she would find fleeting bits of happiness again with a new lover.

She held up my disjointed picture to the light streaming through the windows. She said it looked like we were done. With that, our affair ended. She released me into the sunny afternoon, to walk home alone, kicking rocks and dreaming of Jessica Rabbit.

Read other chapters of Adventures in Virginity:
Birth of an affection fetish ,
Building a Penis Pump at Age 10 ,
The case of the aspiring vagina archaeologists
Exploring masturbation with the Pink Panther

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