The Winning Bid

The highest bidder looked Gary up and down with a certain measure of disdain. What? Gary wondered. Did he expect me to show up on his doorstep wearing nothing but that stupid panty I modeled at the women’s charity event? And it WAS a women’s event now wasn’t it?

“Come in,” said the man, verbalizing his obvious displeasure. “I hope you brought me the item I paid eight hundred dollars for.”

I thought you paid eight hundred for the panty and ME, Gary stood in the dim vestibule thinking. Three hours of my dubious services, while dressed in a freak’s outfit. “It’s in my backpack,” Gary replied, unshouldering the nearly empty zip-up black thing.

The man turned back from the edge of his one-level mansion’s livingroom, with its incongruous mix of modern and antique filling most of the available space. “And I assume you’re going to model it for me?” the man said with raised eyebrows.

“Of course.”

“Good.” The man raised a stiff right arm, apparently pointing in the direction of a nearby hallway. “You can change in there,” presumably meaning a hidden bathroom. The winning bidder at last smiled, albeit faintly. “Time for the day’s first vodka martini. Do you drink?”

“Sure,” Gary replied. It was eleven a.m.

“Good. Then go change. Let’s get this show on the road.”

As Gary lay in bed, ass in the air atop two pillows, being fucked, he looked off at the antique lamp on the nearby table wondering what his wife Deirdre would think of all this NOW. The whole thing had been her idea. Having Gary model her crazy best friend Carolyn’s latest creation at the auction; adding in for good measure, three hours of her husband’s services to the winner bidder, whatever that implied. Now, three weeks later and to everyone’s everlasting surprise, the winner had not been an elderly, affluent, country club type female but a male standing at the back of the auditorium whose face hadn’t even been visible. “Eight hundred!” the auctioneer had shouted in response to the man’s raised hand, a scrolled up auction bifold in it.

“Do I hear nine hundred? Nine hundred?...Eight hundred. Going once, going twice...” Then a gavel had been pounded, making Gary, still out there mid-stage wearing nothing but Carolyn’s latest concoction of satin and lace, wince.

Now the winner was pounding Gary’s ass like it was a horizontal gavel, having said, about twenty minutes ago after a third round of very dry, very potent martinis, “I assume that my eight hundred dollars buys me a fuck.”

“S-Sure,” Gary had stuttered in reply.

“Then finish your drink and let’s get you out of your little outfit and ready for sex.”

Gary was secretly terrified—and thrilled. The psychology of it wasn’t too hard to fathom. This was his chance to get back at Deirdre for embarrassing and humiliating him like that. With another man in their bedroom and elsewhere on a semi-regular basis for starters. But also for dressing him up in Carolyn’s costume and gleefully pushing him out on stage in front of two hundred smiling strangers.

Two can play at this game, Gary thought, legs in the air as his host administered the first of two shallow enemas. It would not be the first time he’d been fucked but it would be the first time in quite a while. Six months or so before he met Deirdre and they began dating.

“I think I may be...bisexual,” a slightly wine-drunk Gary admitted to his new love after she withdrew her warm tongue from his ear and hissed, “Tell me your deepest, darkest secret.” They were in his car, a restaurant parking lot, second date. Bliss? Or had Gary just torpedoed the whole thing?

Deirdre had pulled away, blinking long lashes. She was neither smiling nor frowning. “I’m OK with that. I have a high sex drive. Hope you’ll be OK with THAT. I’m not a one-man girl in other words...”

Over the past eleven years of anal abstinence Gary’s hole had tightened up. But now as the winning bidder plied his trade Gary’s sphincter was loosening up and true pleasure was starting to kick in. “Oh fuck me!” he heard himself say, as if his relentless partner needed any urging. “Fuck me! Shoot your load in me!”

Gary sensed a smile curling his partner’s lips as the man replied, “In due time. Relax. I’m only getting started. I can go all afternoon...”

He could not. A half hour later, though with Gary indeed carrying the winning bidder’s load of semen inside him, along with the ghost of his cock, the man handed Gary yet another vodka martini, a red plastic sword spearing three plump olives. When Gary had sucked the man’s cock, after his enemas but before, and in preparation for, intercourse, that’s what he’d tasted the whole time: tart green olive juice.

Gary accepted warily, woozily. He still had to drive home to Deirdre, after all.

“So I’ll leave the panty behind,” Gary suggested, giving the horizontal white ruffles a downward glance with his hand.

“Why?”

“You don’t want it?”

The man sipped his drink. “I wasn’t bidding on it,” he said, “I was bidding on you.”

Gary felt suddenly flattered. “Really?”

“How old are you? Thirtyfive? Thirtysix?”

“Thirtyseven.”

“There you go. I’m twenty years older. I don’t qualify for the 18-year-olds anymore. I’ll take twenty years younger,” he added, before taking another sip, “any day. With great legs?”

“So I...” At which point Gary forgot what he was going to say. He was drunk. Yep, drunk. The winning bidder filled in the blanks:

“Saw you up there on stage, liked your body. Plus wearing that thing,” and pointing now below Gary’s navel, “suggested to me you were fem. Submissive. A push-over. Just the kind I like.”

“My wife made me wear it!” Gary blurted.

“Still. Even so. Not many other types of men are gonna get up in front of an audience dressed in...that ridiculous thing.”

The man grinned as Gary looked down at himself, once again embarrassed; humiliated. Fucking Carolyn. Fucking Deirdre!

“I don’t even know why you put it back on.”

“You mean...?”

“After we fucked.”

“I thought you’d want me this way.”

The man laughed. “The way I wanted you was bent over in my bed just now, sweet ass in the air. Can you come back tomorrow?”

As the man took another sip of vodka Gary swallowed. Something. It was the size of an olive.

When a bleary Gary arrived home his wife Deirdre was waiting patiently for him in the kitchen, chopping veggies. He’d been gone the regulation three hours plus travel time. A rather dubious five hours total.

“How’d it go?” a bright-eyed Deirdre inquired, looking her husband up and down much as the winning bidder had done when Gary arrived on his improbable doorstep. “I thought I heard a car pull away just now.”

“Uber,” her husband said succinctly. “Too much to drink...”

“Oh?”

Gary nodded.

“That’s what you did all day with this guy? Got drunk?”

“Pretty much. I cleaned his pool for him,” Gary lied. He’d thought about it on the ride home and that was the best he could come up with. He couldn’t very well claim he’d mowed the guy’s lawn, could he?

“It took you three hours to clean his pool?”

“We talked a lot. Shot the shit.”

“You wore Carolyn’s panty?”

Gary looked down—at his trousers. “Uh-huh.”

Deirdre flushed out a smile. “I liked them on you. I’m gonna order a few more pairs for you, from Carolyn. Yellow and...You can wear ‘em around the house. You’ll look cute, hon!”

Gary, meanwhile, was clumsily fishing out the winning bidder’s prize. The pink one made of billowy satin with row upon row, front and back, of white lace ruffles and bedecked with pink ribbons and, front and center, just below the elastic waistband, a large bow. The ultimate in sissy panties in other words.

Gary held the thing up. While Deirdre looked surprised.

“He didn’t want it?”

“Not really.”

“He bid eight hundred dollars for it and then didn’t even keep the thing?”

The thing indeed.

“Want to return it to Carolyn?”

Deirdre made a face. “Of course not. No. It’s been...worn. Twice.”

Her face brightened the way it did whenever she talked about that guy from work she was “dating”; i.e. openly fucking. “No. Keep it. Put it on for me. I want to see you in it again!”

“Now?”

“Why not? You wore it for him all day. Why not me?”

As a grumbling and increasingly unsteady-on-his-feet Gary switched out his shirt and socks and shoes and pants and briefs for Carolyn’s pink sissy panty he eventually said: “I have to go back there tomorrow...”

“Back where?”

“Guy’s house.”

“Why?”

“Cause...I left my car there. My car. Gotta go get it.”

Deirdre frowned. Hands rose to her boxy hips. “You know I can’t give you a ride tomorrow. I’m meeting my friend for a bike ride at eight. I’ll be gone most of the day.” Deirdre blinked incomprehension. “Why’re you smiling?”

“Me?”

“You.”

“I’m not.”

“Yes you are. What’s the big secret? Cat got your tongue?”

“No. Nothing.”

As a bleary-eyed Gary stood there in his sissy panty he was thinking about tomorrow. Tomorrow morning, late. Martinis. That cock up his ass again. The pleasure of its thrusts. The moans. The load (though less than today’s) of sperm he’d gladly welcome, gladly receive.

“So how are you going to get your car tomorrow?” Deirdre asked.

“Uber,” Gary grinned.