Worst Laid Plans: When Bad Sex Happens to Good People

Worst Laid Plans: When Bad Sex Happens to Good People

True tales edited by Alexandra Lydon and Laura Kindred

224 pages.

Abrams Image.

$19.50 (or 7.85$ US if you’re in the states & buy through Amazon)

The back cover of this book says it all: “it has been said that the only bad sex is no sex.   The contributors to this book respectfully disagree.”

Comediennes Alexandra Lydon and Laura Kindred of the famed Upright Citizens Brigade theatre troupe have compiled those tantalizing true-life tales of sexual experiences gone horribly, horribly wrong.   From a young woman giving up her backdoor virginity because of a bet to an aborted attempt at the seduction of a midget met on Craigslist, their monologue-style stories illustrate the downside of putting yourself out there.

Honestly, while most of the stories were pretty funny, they were disappointingly tame in what I thought would be the be-all, end-all Sexual Hall of Shame.   A worthy bus read, even if just for intrigued glances from other horny bus riders.

Where the book really succeeded was in its overall sense of humour, reflected in the clever titles and the glossary at the end, which included hilarious terms like “The Cliterati” (the elite academics of the female anatomy, learned in the art of its manipulation, the most cunning of linguists) and ignoranus (one who has never experienced anal intercourse).

When I sifted through my sexual Rolodex, I realized, much to my own chagrin, that I had quite a few stories that would have fit within the context of the book.   So here’s the one I went for:

Throughout high school, I had a crush on one of my close guy friends.   He had it all: he played the guitar, wore the epitome of silly retro clothes and borrowed his mom’s car so we could drive around and hot box it while listening to Sublime.   But, being the naive and inexperience young thing that I was, I never told him how I felt and moved away for university, my thoughts still drifting to him now and again.

Fast forward a few years and I’m home for Christmas and ready to escape my family for an informal high school reunion on Boxing Day at one of my favorite bars.   A girlfriend greeted me by saying he was looking for me.   I toured the crowded, dimly-lit bar twice but he was nowhere to be found.   Ready to give up, I headed back to my table where he was waiting for me.   We chatted, we batted eyes, a hand may have slipped on a thigh.   Needless to say, my heart was racing!

The lights come on, he’s looking dreamy as ever and word spreads of an after party.   He asks what I’m up to and I cleverly respond with “whatever you’re doing.”   We decide to head back to my (parents’) place, which, in retrospect may not have been the best course of action.   I’d been living on my own for so long that the “ask back” was standard practice by then.

The guest bedroom in my parents’ house is directly across the hallway from said parents, so we crept quietly into the basement.   There we were on the leather couch that we’d watched so many movies on in our teenage years and I swear I’d never been so turned on in my life.   Furtive yet gentle kisses, our bodies pressed together, the longing being felt all the way to the tips of my toes.   He slipped my tights and bottoms off and kissed his way down my bare stomach.   Yes, I’ve always given at least 10 extra points to men who lick my pussy in our first encounter together.   So he’s doing his thing, my head is spinning faster than an out-of-control carousel when suddenly I hear a voice from the top of the stairs calling out “Jessica, what are you doing down there?”

He stops dead in his tracks and looks up at me.   I cover myself up with a blanket and bolt up the stairs to intercept my Mom, whispering through clenched teeth “Mom, I’ve got him down there.”   She sleepily wanders back to bed, me shooting daggers from my eyes at her back.   I rush back downstairs and he’s put his shirt and jacket back on.   “I think I should probably just go,” he muttered, unable face my eyes.   “No, no,” I stammered, but knew I had to see him to the door.   Yes, there’s the story of when I got cockblocked by my Mom with my high school crush.   And I never even got to handle the penis I’d been fantasizing about for so many years… maybe next Christmas?

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