The Pangs (and Pleasures) of Regret

Emily couldn't believe it. She and her roommate, Alexis, had taken their usual Saturday night trip to the local college bar to have a good time and maybe pick up some guys. For the first two hours, everything had gone amazingly. They'd gotten a bit drunk, smiled and laughed, flirted with guys, and even danced with a few. Finally, she had gone to the bar to order a drink and take a break from dancing when she spied Jonathan.

About 6'1" with a thin build that nevertheless hinted at a hidden surprising athleticism, he had caught her attention from the first glance. He was standing back from the bar a bit, so she had stepped up to initiate the conversation herself.

Despite his lithe body and decent fashion sense, Jonathan had quickly proven to be a tad awkward and unconfident, stuttering nervously through his sentences and struggling to her in the eye. With every exhibition of awkwardness, Emily smiled an increasingly predatory smile. Guys like this were her favorite.

As a three-year veteran of the university tennis team, sporting 5 feet 10 inches of beautifully tanned skin with long blonde hair, smooth muscular legs, and D-cup tits-a rarity for a girl in her elite physical condition-she was used to intimidating the more introverted, nerdy types.

She loved it.

Sex was just like tennis to her, especially in three key ways: she was loud, she loved being in control of the game, and she always came out on top.

Jonathan had been perfect for her next conquest, and she'd been determined to take him home with her. But, at one point, she had turned around to look at some loud noise that had caught her attention, only to turn back around and see that he was gone. Maybe he'd gotten too nervous, or his friends had wanted to leave; who knows. In any case, she never saw him again that night despite searching until it was finally time for her and Alexis to leave.

When they got back to their apartment, Emily went straight to her room and shut the door, Jonathan still on her mind. If she couldn't fuck him tonight, she'd have to make do. She rummaged through her bathroom drawer and picked out her biggest dildo, about 6 or 7 inches. She loved to assume all guys were this huge; it made the fantasies much more fun.

She went to her bed and cleared everything off it except for one sturdy cylindrical decorative pillow about 4 feet long and most of a foot in diameter. It wasn't quite the size of a real human, but it would do for a male torso in a pinch. She stood it up, strapped the dildo to it, and pushed it down as if it were a hapless, submissive guy.

She climbed over it and reached her head down, licking the shaft from base to tip. She spit in her hand and rubbed the huge cock, stopping occasionally to suck it as far down as she could, until she was sure it-no, he- was ready.

Her thin pants grinding against him and growing wetter every second, she ripped off her shirt and bra, letting her huge tits bounce against her chest as a show for the Jonathan she imagined was there, with a seductive look in her eye to match. Continuing to shake her boobs sexily, she pulled off her damp pants and soaked thong and straddled the cock, though not yet inserting it.

"You ready for this, kid? I'm about to change your life," she said breathfully to the pillow.

She slid down onto "Jonathan"'s dick, her pussy so wet it filled her until her labia hit his base.

"OOOOOOOHHHH," she moaned loudly. She didn't care if Alexis heard.

She slid carefully up and down the shaft, impaling herself again and again, continuing to moan loudly.

"Oooh, you're so big! Fill me up, Jonathan, fill me up!"

Her cunt so wet it was dripping out and dampening his cotton skin, she collapsed her chest onto his chest and reached her hands out to pin his imaginary arms to the bed. She humped him slowly but forcefully in this position, and waves of incredible pleasure began to wrack her body as his dick tapped his G-spot.

"Stay there, boy! Stay right there!" she exclaimed as she held his body tight and thrust against him, the pleasure building in her body to an incredible, almost unbearable, level. Every time she completed a thrust, her pussy lips compressed and spat out wetness like the wringing of a sponge with a sexy, sticky squelching sound.

As the pleasure built, it brought with it a pressure that demanded to be released. She let go of his arms and slid her hands under his torso, gripping him in a tight whole-body bear hug as the pleasure reached a beautiful, powerful threshold.

"AAAAAAAAHHHHHHHH!" she moaned as the orgasm swept over her.

It hit in waves, every heartbeat sending a new wave of pleasure rippling through her bloodstream, carrying it through her entire body from head to toes. Still bouncing up and down on her lover's cock, she leaned up and grabbed her boobs, feeling their inexplicable simultaneous softness and firmness, running fingers over her sensitive erect nipples that throbbed in tune with the rest of her trembling body.

As the orgasm subsided, she looked down at "Jonathan" and noticed that in addition to the sweat she'd been producing and the wetness she'd been leaking the whole time, at the moment of orgasm she must have blasted him with a powerful squirt. Nothing else could explain the sheer volume of fluid on his stomach.

She leaned down and placed her boobs where his face would have been, imagining him sucking gently on them, and lay there for several minutes. With her fantasy for the night fulfilled, she raised herself off his cock and rolled to the other half of the soft queen-sized bed. She wondered for a moment if her Jonathan had managed to orgasm at all, then realized she didn't care. Sex was just like tennis after all; all that mattered was being in control and coming out on top. Who cares about the opponent?

As she drifted off to sleep, completely naked and still slightly wet, she pondered whether she should have put her toy away before going to sleep. She decided against it; after all, what good one night stand didn't include a Round 2 the next morning?