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A Wicked Wednesday post/flash fiction by K.C. Cave.

This week’s prompt: an unexpected meeting that you remember for years. Here’s a fictional encounter, one where a young woman’s voluntary deflowering doesn’t go as planned (does it ever?).

backseatHannah’s panties were bunched down around her ankles as “Biff Baxter” fumbled with his dick. Her first attempt at coitus in Biff’s classic ‘68 GTO was not going as planned.

Thrusting her hips back, she reached between her legs to guide the football star’s straining cock to her pussy. His futile thrusting had been going on for, like, a half-hour. Well, it seemed like a half-hour. Hannah’s frustration was growing.

“Lower, lower…no, goddamn it, wrong hole,” Hannah growled over her shoulder, her head crammed into the armrest as Biff attempted to take her virginity doggy-style in the backseat of the goat.

“I’m pushing, but it won’t go.”

“I thought you knew what you’re doing,” Hannah shot back, disgusted by the puerile efforts by Hilltop High’s star quarterback to make her a woman—both to mark her eighteenth birthday two months before and her imminent graduation.

His real name was Leonard Eels, pretty lame for a varsity hero and universally acclaimed Big Man on Campus.  Thus everyone, including teachers, coaches and Principal Poop, called him “Biff Baxter.”

“It’s your fault. You’re too small. Or tight. Or something.”

Right, Hannah thought. Blame me.

This was not how she had imagined her magic moment of blossoming womanhood would turn out.


Hannah pushed him back with her bare ass and flipped over. After pulling her panties back into position, she smoothed her skirt down and settled on the backseat. A glance at Biff, collapsed against the opposite door, revealed his lower lip protruding. The big baby was pouting.

Right. The guilt trip. “Well, I guess I can at least get you off,” Hannah conceded.

His eyes lit up. “A blow job?”

“Better than that. Push down your pants.”

Biff rearranged himself in the middle of the backseat, his jeans and tightie-whities scrunched below his knees. He spread his arms across the back of the seat, eager to be serviced.

Hannah found her purse on the floor of the car and pulled out a small bottle of hand lotion. She slathered the stuff on Biff’s straining, but not very large, dick. He was a circumcised fatty, Hannah decided. Thick, but not long—barely four inches. And, she noted, his pubes could use a trim.

“Slide down.”

Biff obeyed, giving Hannah better purchase to his throbbing cock. Enclosing his member, she swirled her lubed palm over his red dick head. Biff’s hips rose off the seat, his eyes rolled back, and gurgling sounds escaped from his throat. Hannah slid a hand down to his balls and articulated each gland as she jerked him off, slowly and deliberately. She was just about to begin alternating strokes with both hands, when…

Jism sprayed out of Biff—big copious strings of white cum that splashed the upholstered headliner, the back window and…

“My hair! Jesus, don’t you have any self-control? How am I going to go home with your jism in my hair?”

“Me? Me? Whudja expect? And where’d you learn to do that? That felt incredible. That’s the best handjob ever.”

“I was just getting started, you moron. Where’s the Kleenex? Ugh! What a fucking mess. Pull your pants up and take me home.”