March Madness

You shook your head ruefully as you walked to the car amid the jubilant postgame throng. You should have known the kind of trouble you'd get yourself in on gameday. He kept baiting you, and you kept biting when you should have known better.

"Care to make it interesting?" he had smirked as the two of you had approached the sports bar a few hours earlier. The Deacs were actually in the tournament this year, and the whole town was thronging every place with beer and a big screen in hopes that this was the year. It was going to be a great game, and you had been in high spirits. High naughty spirits. So you sensed what he was putting out there.

"All day long," you teased. "How much do you want to put on it?"

"Skin in the game, eh?" he mused.

"You got it. How much?"

He leaned in close as he pulled the building's door open for you. "What if I don't want to bet money?"

Oh, yeah, high naughty spirits. You knew both your imaginations could get radical; this was going to get interesting. "What did you have in mind?" you purred, imagining all kinds of things he had in mind.

"Let's put your skin in the game," he murmured. "What do you say to a swat a point?"

"This is a basketball game," you replied, putting a finger to your lips in a sarcastic mockery of thinking about it. "That could be a lot of swats."

"Yes it could. How much of your skin are you willing to put on the line for the old Gold and Black?"

You remembered pursing your lips in real thought now. This was the best team in a while. This really could be the year. If the team got hot, it could mean over 100 swats. Did he want you to root against the team to save yourself?

No, you had decided. This was the dedication of a fan being tested. You'd cheer for the team knowing every single point would be tallied on your ass later. And you'd cheer anyway. You almost laughed out loud--you'd be taking it for the team. Like literally.

"You're on," you had said with a nod.

And you had been on. Every basket, every cheer from the room, you knew was going to get burned onto your ass. The Deacs had been on fire today. Your anticipation of joining them had grown stronger and headier as the game progressed.

You shook your head slightly as you walked across the parking lot now to the car, darkly amused at your stupid pride that had pushed you to raise the stakes. You had been crazy to think you could get something past him.

"If he misses both of these," you had leaned in close to whisper as the substitute guard took position at the foul line just before halftime, "you send me a dick pic from the men's room."

He glanced at you with a grin. "And if he makes it?"

"Your call," you shrugged. This guy wasn't a starter.

You hissed slightly as you slid into the car and the butt plug shifted inside you. You should have known he would have anticipated you trying to up the ante, and he had come prepared to make you pay for your overconfidence. You had sent him pics of you inserting it in the ladies room, and had been wearing the slender silicone plug ever since. The fullness back there had been a distracting buzz in the back of your head for the whole rest of the game.

Distracting and arousing, too. Arousing enough that it hadn't been the only kinky side bet you had tried to talk him into. And you had lost and lost some more. You hadn't been trying to lose, but had gotten to a place of something like weird curiosity. How wild a stack of consequences could you think of? The tally rose, and little by little, extra pieces had ended up on the table.

Or been removed. You had to surrender your panties at the end of the third quarter. Your stupid double-or-nothing meant you had to hand them over right there in the booth. No trip to the ladies room. You had ended up cutting the sides with his pocketknife and jerking them out from between your thighs, sliding them past your plugged ass (and now moist slit). He had stuffed the now-tattered panties between the bench cushions. You'd never see them again, and some employee cleaning up after the chaos of the game was going to have a story to tell.

It had gotten both dreadfully worse and gloriously awesome as you went for broke in the last quarter. You were totally up over that 100 swats. Way over. You had double-or-nothinged your way into multiple hundreds now, with different implements, in different positions. Over multiple days. You'd be taking it for the team all week.

And you'd be giving it up all week, too. Starting right now.

"You racked up quite a tally in there," he quipped. "And as I recall, you have something you need to do before I even start the car."

You gave him a little bit of saucy side-eye as he reclined his seat slightly, and you reached for his zipper to free his cock. It was lucky, you thought, that he had parked in a corner of the lot, so nobody was really walking by.

Lucky, or crafty, you added as you wrapped your lips around the head of his hardening prick. You swirled wet tonguing kisses around him, refraining from bobbing your head much, in case the motion caught somebody's eye on their way to their car and they checked to see what was going on.

You didn't get interrupted by a gawking passerby, though he did sweep your hair to one side so he could watch you suck him off there in the parking lot. He took a few pictures, and you were in a provocative enough mood that you even looked right into the camera for one of them. He'd be keeping that one, you were certain.

Uninterrupted though you were, the exhibitionism of it got to you. Yeah, you were sucking a dick in the parking lot after a big win. Yeah, you were celebrating, and you probably weren't the only one. You pondered that as you craned your neck properly to deepthroat him. There were probably victory blowjobs happening in more than one car in this very parking lot. Be true to your school, you thought wryly.

It gave you a satisfied flutter that it didn't take much of you touching your nose to his pelvis for him to give the grunt you knew well. He had been turned on the whole game, too, betting and grinning and keeping the mental total. You backed off slightly and kept your tongue moving gently on the underside of the head as it filled your mouth with his salty cream. It was really hot in the car now, and you wiped sweat from your forehead as you took in the full load, swallowing and then popping your lips from his spit-gleaming shaft with theatric relish.

"That's one," he whispered, taking a moment to catch his breath as you got settled back into your seat. "I'll be looking forward to that every morning this week."

"I'm a woman of honor," you jibed as he brought his seat back up and started the car. He got the air going, and backed out of the parking space to start home.

"Then I guess you had better work on the next step. The car didn't start until I came. You don't get out until you do."

You made a sound somewhere between a whine and a giggle, and got your own pants open. At least you weren't wearing any panties now, so your fingers could find your little pleasure nub without anything in the way. And you were ready for some attention down there--you could feel the full swell of arousal, and your clit almost gave a spark when your finger caressed it. You ran two fingers in a tight circle pattern over that little kernel as he drove, closing your eyes to concentrate on dirty thoughts and hunt your climax.

Once, you had the sensation that you were being watched, and opened your eyes slightly. You were at a red light, and there was a semi truck in the next lane. You couldn't see the driver, but for a moment you wondered if he could look down and see your hand being naughty. You felt another nervous rush of exhibitionism. You weren't normally someone who showed it off to strangers, but hours of titillation during the game, the deep press of the plug in your ass, and your currently questing fingers had taken you to a pretty bold headspace. So what if there might be a trucker watching you masturbate in traffic? He'd have a story to tell about that one time in Winston-Salem. He might even beat off later thinking about it. Thinking about having seen you.

The idea that your pleasure-seeking might drive someone else's hit you hard. It was the push you needed, the tweak to your headspace that brought your orgasm on like a wave. Your whole body tensed as you came boldly right there in the passenger seat, crying out in triumph as your climax crested over you. The plug felt enormous as you clenched around it.

The light turned green, and you slumped back in your seat, breathing heavily with your eyes closed, basking in the glow. The car stank of sex now, and you smiled lazily, knowing it was all far from over. You felt him reach over and gather a fingerful of your wetness, and opened your eyes to watch as he tasted it.

"Yep," he said. "Still a favorite. I'd put that on my ice cream if I could."

You rolled your eyes, and rode home in a happy post-orgasm daze, imagining what was to come.

You didn't have to imagine for very long. You walked into the house ahead of him, still glowing, with an exaggerated hip swing, letting him imagine the plug peek-a-boo-ing from between your cheeks. You turned to face him as he closed and locked the door, but he smiled and shook his head, twirling a finger.

"Turn around, bare it all, and bend over."

You licked your teeth at him, keeping eye contact as the rest of you turned around until you had to rotate your head, too, and started undressing. You took it slow, a no-music striptease, feeling his eyes on your shoulders, on your legs, on your back, on your skin, on your ass. You could feel the warm moistening build further between your legs; you knew you'd be expanding his own arousal, and it turned you on to know it. At last, you bent over, stepping your legs apart so he could see the purple silicone base of the last thing you were wearing, bracing your hands flat against the accent chair in the living room.

You felt him step close behind you, his hand caressing the curve of your rump. You pushed it out and gave it a shimmy. He gave it a light test swat, and at your giggle he reached his fingertips between your cheeks and wiggled the plug at your backdoor a few times. You inhaled deeply, and as you exhaled he withdrew the flexible length of the plug. You felt the pressure within you subside as the plug left you, and sighed with both relief and anticipation.

Then you felt his finger teasing at the edges of your rosebud, and almost moaned. You weren't sure if fingering your ass was anyplace on your debt tally, but you didn't get a chance to think much about it before that finger sank deep. Your legs started shaking immediately. He knew exactly how to touch you back there, how to work the angle and the depth just so. He worked that deliciously wicked finger of his right where it needed to be. Right where you needed it. Right where you wanted it.

You were already half-orgasmic when you walked in, and you could feel your pussy drooling as your sensitized back passage radiated pleasure. You started pushing back against his finger. Wanting it deeper, harder. He understood and obliged you, briskly finger fucking your ass while you moaned and gasped. And then came.

You seized up completely around that finger, your knees locking back and your eyes squeezing shut and your moan turning into a thin keening wheeze as your insides spasmed. You were shivering in delirious delight as he withdrew his finger, and he gave you a minute or two to come down from the peak and catch your breath.

"Ready for the next payout?" he asked, his voice both humorous and strikingly seductive.

"Ready, sir," you breathed. "Sir" for the next three days had started once you walked in the door, you knew. Stupid three-pointer.

The first real swat landed, his hand cupping your left cheek perfectly. You went up on your toes and grunted from somewhere between surprise at the sting and arousal at the submission. Then that hand landed again. And again, and again, and again and again and again.

You had a long way to go, you knew, as the fire spread across your cheeks, your sex started leaking down your thigh, and the rapid SPACK! of his hand, hard on your skin, filled the room. There'd be his belt later, and a flogger, and the special cane, and not just on your ass, you knew. You would have welts and stripes on your back, and your thighs, and your tits, too, by the time your debt was clear. He would be taking your mouth again, and your cunt, and your ass, claiming you over and over. You'd be working this off for days, submitting willingly, dipping in and out of a lush red fogbank. Immolating punishment and soaring pleasure would combine into something that would drive you near madness before the debt was paid. Your stupid-bet-happy ass was about to get you taken all the ways.

Yeah, you were going to take it ALL for the team.

Worth it.