The Mammoth Book of Best New Erotica 2 by Maxim Jakubowski

Author:Maxim Jakubowski
Language: eng
Format: epub, mobi
Publisher: Constable & Robinson

Surrender Dorothy

Lisa Montanarelli

Dorothy was my best friend in college. When we first met, she was, by her own definition, “straight”. But her definition of straight changed like the wind. Dorothy was the first woman I had sex with, and vice versa. She framed this event as an act of charity – to help me determine whether I enjoyed having sex with women – as if she somehow represented all women on the planet. After having sex with me, she decided that she also had to sleep with her best friend from high school, who would be crushed if she ever found out that Dorothy had slept with any woman other than her. Thus one charitable act led to another, and soon Dorothy was shepherding me into sexual configurations of various numbers and genders. Since I was the shy one, I was happy to rely on her to organize our sexual forays. Until she finally came out as bisexual, she had a way of organizing group sex, then fleeing the scene, racked with guilt. As I later discovered, Dorothy fantasized about having sex with virtually everyone she knew, and my burgeoning bisexuality provided an opportunity for her to test-drive some encounters that would otherwise have been difficult to rationalize, given that she still called herself “straight”.

My first threesome was orchestrated by Dorothy and a guy she was fucking named Matt, who happened to be my ex-boyfriend’s roommate. What I remember most about the experience was Matt’s effort to make sure everyone felt included by mentioning both our names as he came: “Oh, Dorothy . . . oh, Lisa.” As I fell asleep that night, I couldn’t help feeling as if I’d just had my first bisexual experience, even though I’d already identified as bisexual for a year and had sex with both men and women individually. Nonetheless, if I had sex with a man at 7 p.m., and a woman at 8, who’s to say I didn’t go through a heterosexual phase at 7 and find my true lesbian identity an hour later? After my first ménage à trois, I felt as if I’d jumped through the final hoop of true bisexual identity.

We finally cornered Dorothy into coming out as bisexual. It was a bit like gang warfare, and it happened during a surprise party that I organized for her 19th birthday.

Several months earlier Dorothy had confided her core childhood masturbation fantasy in the wee hours of the morning, when our inhibitions were down. Since the age of seven, she had fantasized about crawling through a paddy wagon of authority figures, consisting of her grammar school teachers, camp counsellors and babysitters. Eventually, she came to the last link in the chain – the school principal, who would spank her hardest of all. That was the part of the fantasy that made her come.

I admired Dorothy’s sexual precocity. But I also realized that she was telling her childhood fantasy from the perspective of her present 18-year-old self. She was thus embellishing this

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