Ballroom Affair

Story Info
A high end fundraiser becomes something more.
3.8k words
4.43
45.4k
27
4
Story does not have any tags
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
tryst
tryst
63 Followers

The party was huge. A hundred or more costumed people drinking and dancing their way around the city's most exclusive hotel's ballroom, an invitation only affair put together by Merlin Oberon, the famous billionaire turned philanthropist. The night's gala had already raised, according the thermometer-like gauge on the wall, nearly fifty thousand dollars to support stem cell research, and the fete was only two hours old.

Peter Overbee was smashed. He wasn't a frequent drinker, and it'd taken three Manhattans to assuage his nerves enough to climb into the costume his wife had provided, and there'd been two more since their arrival. It'd been a semi-private joke, really. Olivia wore the pants in the family -- her family's money, as much as her personality, made that inevitable - so a Halloween role reversal had seemed, at its conception, harmless and funny. She was wearing a custom Armani suit, he a too tiny designer gown from some exclusive boutique he'd never heard of. And, he was forced to admit, they both look fantastic.

But his scalp itched insanely under the expensive ash blonde wig. The mascara and false lashes made him want to rub his eyes. The foundation and powder coating his face felt like an oppressive mask. The breast prostheses glued to his chest, combined with the unfamiliar four inch heels and unaccustomed liquor intake, kept him off balance. The weird slickness of the expensive hose, stretched by garters, sliding over his shaven legs, made him feel exposed above the short hem of the gown. Worst of all -- worst by far -- was the throbbing half erection trapped away by the gaff his wife had insisted he wear. Not only was he drunk, he was scared. Being excited by wearing women's clothing had taken him utterly by surprise.

Embarrassed, horny, and confused, Peter just wished the night would end. He bent toward his wife, aware of the pressure of his breast against her arm, and whispered loudly that he had to use the restroom. Gwinn grinned crookedly. "Be sure to use the right one, babe."

"Which one is that?" he snapped.

Her eyes narrowed at his anger. She raised a convincingly thickened eyebrow. "I guess that depends on which way you want to swing, hot stuff."

He softened his tone. "Come with me? Please?"

"Scared, babe?"

"Please?"

"Alright, hon. We need fresh drinks, anyway. We'll hit the bar on the way back."

Peter let Gwinn tuck his arm under hers, and was grateful for her support. The movement elevated his drunkenness by at least two notches before they'd walked twenty feet. His head reeled. He heard himself giggle as his wife wrapped her arm around him to keep him from falling off his heels.

She leaned into his ear. "Let's both go in the boy's room. I'll bend you over in a stall and do you from behind."

He giggled again. "What kind of girl do you think I am, anyway?"

"Why, a nasty little slut. Of course."

"Well!" he huffed, as they left the ballroom and entered a corridor. "I --"

His indignant protest was silenced by his wife's mouth crushing his as she backed him against the wall. Her tongue stabbed between his startled, parted lips as she pressed hard against him.

He groaned into her mouth as her legs forced his apart and her groin began rubbing his insistently. His eyes widened as he felt a long, hard bulge in her slacks where there should be nothing of the sort. Her arms trailed down his sides and drifted back to cup his buttocks just above the level of his hem.

He groaned again, more urgently, and found himself grinding his smooth belly against her erection, draping his arms over her neck and pulling her tighter.

He broke the crushing kiss. "Oh, God, this is so fucking hot," he moaned into his wife's ear.

Gripping his ass tightly, she forced him up and down against her crotch. "See? I knew you were a dirty little bitch. Ready to fuck me right here in the hall, aren't you, slut?"

He whined, tried to reclaim her mouth with his. She pulled back. "Look at you, cunt! That whore-red lipstick's all smeared. Have you been sucking cock, baby? Have you already been on your knees with a dick down your throat?"

"I'm not . . ." he panted, ". . . Just for you . . ."

His lips found hers, attacked them. His false breasts were mashed into her strapped ones. His cock, bent backwards and trapped, throbbed with agonizing urgency. On his tiptoes, he was able to position the dildo under her costume to ride just at the base of his cock. He threw his head against the wall and gasped for breath. A little more. Just a little more.

Gwinn jerked away so suddenly he almost slid down the wall.. Her eyes raked him from top to toe and back up. "God, what a gorgeous slut you are."

His arms reached for her. "Don't stop. Please. I was almost there."

"Not yet, baby. Not here. But, believe me, I'm going to fuck you til you scream when we get home. Now run along and do your business. And don't forget to fix your face." Swatting his ass, she strode back into the ballroom.

Stunned, he just leaned against the wall, reeling only on the inside. Voices of approaching revelers, headed back from the restrooms jolted him to alertness. Three men, all leering at him as if they'd just watched him fuck in public. He hurried, as evenly as he could, away from them, their lewd stares. Still emotionally numbed, he turned into the men's room. And stumbled to an abrupt halt, his confusion compounded, a vivid image etched onto his retinas.

Cold, gleaming marble floors, walls, and countertops. Sterile blue-yellow fluorescent lighting. The echoing clack of his spike heels, then near silence. Only his shrill intake of breath, the muted sixty-cycle buzz of the lights, and the trickle of piss into water as the only other person in the room used the urinal.

That person also wore a dress -- red to Peter's black -- tall heels with nylons and garters. Smooth ass cheeks, parted only by a thong, seen because his hem was lifted to pee. Raven hair down nearly to that round ass. Long sleek arm topped by lengthy scarlet nails braced overhead against the wall as he relieved himself. The other hand, visible between his sleek legs, was delicately guiding the tip of his cock.

He slowly turned his head, obviously more than a little drunk himself. "Sorry, mam. Little girl's is next door."

Peter gaped. "No. It's . . . I'm a guy, too. You just surprised me. Wow."

"No shit?" he laughed. "You're a dude? Damn, you sure look fine!"

"Hey, you had me totally fooled, too. Only one little thing gave you away." Slowly, he moved toward the rank of porcelain on the wall.

His dark-haired companion laughed, looked down. "Little! Eight inches hard, I'll have you know! A little skinny, maybe, but --"

"Hey," Peter laughed, "that's way more than I want to know." In profile, Peter saw the guy was showing some amazing cleavage. Totally believable. And his face, from the customary two partitions away, was stunningly beautiful, totally feminine. Pale blue bedroom eyes. A chisel-sharp widely bowed mouth, a high gloss deep vermilion, smiling impishly. "God, you're beautiful!" The words were out before he could stop them.

Flushing bright red, he jerked his eyes forward. Guys don't look at guys in bathrooms. Guys don't tell other guys they're beautiful.

His companion laughed -- not exactly like a woman. "Thanks. I needed that. The way tonight's been going . . ." He shook his head, causing the black tresses to cascade, bent forward a little and jiggled as he apparently tucked himself away. Peter was almost positive those amazing tits actually bounced.

"Yeah," Peter agreed, making himself face forward again, "been strange for me, too."

"Bad strange or just strange?"

Peter giggled a little. "Just strange, really. Maybe even a little good strange."

The guy had stepped back a little, was digging through his purse, but his eyes were interested and focused on Peter. "Oh?"

Peter felt the warm rush as a long-full bladder released. "Ah. My wife. This was her idea and, uh, she really likes it." His urine stream faltered briefly as his dick swelled at the memory.

"Oooh," his new friend cooed. "Somebody's been feeling frisky tonight." He'd extracted a silver cigarette case and lighter, delicately picked out a long, slender white smoke.

"You can say that again. I was scared shitless at first, but, jesus . . ."

"Umm," he said, lighting his cig. "Can I be nosey? Is this your first time out?"

Peter laughed, rearranging the parts below. "This is my first time, period!"

"You've got to be shitting me!" he said. "No way in hell this is your first time dressed! You're a total fox, man!"

Blushing, he still felt pleased. "Compared to you, I look like a bull dyke. I, uh, have you, I mean . . ."

The brunette exhaled, thought for a moment. "My wife and I," he waved the double band on his left ring finger, "have been doing this for two years now. "I've been full time for about a year."

"Full time! Oh my God! You mean --"

There was an eternal silence after Peter choked off his shout. The lovely face opposite him seemed to fold up into itself as tears welled from the eyes. He raised his hands, covered his face, and turned for the door.

"No," Peter yelled, leaping, scrambling in his heels. "Wait! Please! I'm sorry!" He managed to grasp the brunette's arm. "Please. I didn't mean it that way." He made his voice more soothing. "It's just that this, this dressing has me so fucked up. I mean I hate it and I love it and it makes me feel sick and feel great. And when you said that, I kinda panicked inside. I'm sorry. Please don't run away."

The girl -- or whatever -- allowed herself to be soothed. Peter somehow found himself hugging her. Gently holding her as her tears slowed. She was a few inches shorter that Peter. Her hair smelled fantastic. Dully, he realized it wasn't a wig.

"It's these fucking hormones," she finally told Peter's false chest with a sigh. "Keeping just the right levels is a total bitch. I'm sorry I freaked out -- but people have been giving me the eye all night, whispering, laughing, and . . ."

"Hey, hey.," he soothed. "Fuck 'em if they can't take a joke."

Her blue eyes twinkled as she looked up at him. "So I'm a joke now, huh?"

His brown ones stared back. "You don't hear me laughing, do you?"

"Uh uh," she breathed playfully, twisting away, giving his arm the touch of a large, warm breast beneath the thin red fabric of the gown as she pranced flirtatiously toward the bank of sinks and mirrors. "Come here. We've got to fix your face, dude."

Nothing, not one thing about her, looked male, sounded male, felt male, or smelled male. An utter stone fox, long and lean. Eight inches, Peter reminded himself. A little skinny.

She turned, hoisted herself onto the countertop, found a replacement cigarette, and crossed her legs. "Let's see what we've got to work with. What you carrying in that little clutch purse. Can't be anywhere near enough."

Peter approached, virtually hypnotized by her dangling leg, the grace of her cigarette, her restrained sensuality. Tease. Flirt. As he stepped up to her, she parted her legs for him to step between. The revealed red panties bulged.

She grabbed his purse, snicked it open. "About what I thought. Well, lipstick and powder at least." She speared Peter with blue eyes. "Guess we'll have to use some of my stash. Here. Hold this," she said, handing him her cigarette. He recoiled slightly. She laughed throatily. "Oh, come on, it won't bite. I'm just asking you to hold it, love. Besides, you think it looks sexy when I smoke, don't you?"

He nodded mutely, staring into the mirror at the lipstick stained cigarette burning between his slim, manicured fingers. He adjusted it in his hand until it looked more natural. It did look sexy. Bend the wrist a tad. Relax the hand.

She grabbed his attention. "Bend down, babe. Let Rachael work on those sexy eyes of yours." She scooted forward on the countertop until her groin touched his belly, her legs wrapped around his, pulling him close.

He closed his eyes as she set about her task. His breath was shallow and rapid as she deftly fussed over his face. The heat from her groin was overwhelming as he fought for some sense of stability. It was futile. All he could do was feel. The heaviness on his chest, the tight hug of the dress. The containment of the stockings. The upthrust angle of his heels. The silky legs wrapped around him. His hips wanted to rock, press against her where they met.

Her voice was distant, something about lipstick. He felt the press and slick glide against his lips, tasted the candy sweetness. Then something else. Gloss? Even slicker. His hips were moving just a little now. His bent-back cock strained against the imprisoning gaff.

"Jesus, hon, you are one hot babe," Rachael said softly. "Open your eyes. Check out the fox in the mirror."

He did, and was stricken. His red lips glistened and pouted to be kissed. His eyes were heavy-lidded with makeup and desire. The cigarette seemed to belong in his hand Hot. Too fucking hot. Fuckable. His hips moved obviously, though unconsciously, against Rachael.

She guided his cigarette hand to her lips, drew deeply, locking gazes with Peter, then, through loosely pursed lips, exhaled slowly into his face. "Looks sexy, huh?"

"Yes," he whispered hollowly.. "Nasty."

"Umm. Slutty. Do I turn you on? I love to suck things. Cigarettes . . ." she demonstrated, repeating the upward exhale. "Other things, too." She slid her legs up his, encircled his waist and locked her ankles behind his back. She leaned back against the mirror and began meeting his thrusts. "I'm so fucking hot, love. Looking at you, feeling how turned on you are, too. You are, aren't you, babe?'

"God yes."

"I'm such a slut, baby. Are you a slut, too?" So close, just from rubbing against her.

"I . . ."

Loud drunken voices grew louder beyond the door and shattered whatever it was that was happening inside Peter. Rachael just giggled as he leapt backwards, staggering in his heels. Agilely, she stepped to the floor and caught him by the arm before he fell. They were arm in arm and moving toward the door before it was flung open and a pirate and vampire waltzed in.

"Hey!" the pirate began.

"All done guys," Rachael interrupted in a rough baritone. "Come on, dude, the girls are waiting." She led the still panicked Peter past the vapidly staring vampire. As the door swung closed behind them, Rachael breathed wickedly into Peter's ear, "But we aren't done, are we, slut?"

"I . . . I can't . . ."

"Of course you can, baby. Meet me tomorrow afternoon, six-ish, at the Salazar Hotel. In the bar." Her soft breast pressed against his harder one. Her lips barely grazed his. Her could feel her erection burning against his sleek thigh. Then she was gone, leaving him panting. Moments later, still dazed, he began moving unsteadily back toward the ballroom. Olivia was leaning insolently against the wall just around the corner. She raked him with narrowed eyes. "Hot, babe. The cigarette's a nice touch." She stepped in close behind him, pressed the lump in her slacks between his cheeks and kissed the side of his neck. "Let's go home and fuck."

He looked stupidly down at the half smoked Virginia Slim between his fingers, ground his ass back against her. He tasted Rachael's lipstick as he amateurishly puffed smoke. "What kind of girl do you think I am?" he repeated.

One of her hands came up and squeezed his false tit, then tucked something into his cleavage. "The kind who'll do anything, all night long, for a thousand bucks."

She swaggered to him. "Suck it for me, love. Suck some smoke, slut. Imagine it's my cock sliding between those gorgeous lips." Her groin met his, ground into him, while she leaned back and stared at his face through narrowed eyes. "Be my slut, baby. Be my nasty little whore."

Something warm and wet happened deep within Peter as his wife's false cock dry fucked him through his dress. He humped her back and brought the smouldering tobacco to his ruby lips. As he drew on it, filling his mouth with acrid smoke, he filled his panties with cum. It was an orgasm like none he'd ever experienced before. Even after his cock had twitched its last, the inner heat went on and on. He found he'd wrapped one leg around his man-wife and was shamelessly grinding into her, blowing smoke into her face just as Rachael had with him a lifetime earlier. He heard himself repeating her words, "Yeah, I'm a slut, baby. I'm your filthy little slut. Fuck me, honey. I need you to fuck me so bad."

He awoke the next afternoon, alone in their shade-darkened bedroom, with a crushing, sick hangover and no memory of how it came to be. He hurried to the bathroom, barely making it to the toilet before the vomit exploded from his stomach. The dry heaves seemed unending. More wretchedly ill than he could ever remember being, he curled up on the cool tile of the floor and prayed for death.

An odd feeling called him back toward consciousness. Through tear-blurred eyes, he saw that he was wearing the purple teddy and panties he'd given Olivia for her birthday the year before. Even as he formed the question in his mind, much of what'd taken place the night before crashed upon him like a tsunami. The costume party. Olivia grinding against him. Rachael nearly seducing him. Holding the cigarette and wantonly begging his wife to fuck him. And, even worse, how she had fucked his formerly virgin ass with her strap-on as he'd howled, like a drunken whore, for more.

He wretched again, before nearly tearing the nightie in his feeble haste to get it off. Dragging himself to the basin to rinse his mouth, he nearly cried as the mirror revealed his face. Mascara had run down his cheeks, haloed around his eyes. Traces of lipstick scarred the corners of his bruised mouth, and the fresh memory of Olivia fucking his face with the dildo crashed upon him. He sank to his knees and gave in to the tears of horror overwhelming him.

Sometime later, he dragged himself back to bed and sobbed himself to sleep.

Neither mentioned, or even alluded to, what'd happened. That was awkward at first, but he welcomed it, as opposed to the alternative.

The next-to-worst thing was that Olivia was amazingly more passionate than before the party. They fucked daily, for the first time in their marriage, and she relished a more dominant role in bed as well as out of it. She demanded he use his tongue on her at least as frequently as his cock. She was aggressive and wanton. She loved toying with his asshole and nipples. Her favorite position was now on top. He loved every instant of it, too. Still, every time she fixed him with the feral gaze he'd first seen the night of the party, it reminded him of how wonderful it'd felt to be the fuckee, not be the fucker. He sometimes found himself lost in fantasy, remembering, and suffered ghastly attacks of guilt and shame. He became moody and depressed, but that didn't prevent him from screaming out the most intense orgasms of his life when they fucked.

The very-worst-things, though, were the business card and lipstick he'd found while unloading the little clasp purse he'd used that night. "Rachael Nixon, CPA," it read, with office and cell phone numbers. It smelled of her perfume. He'd thrown it away and retrieved it from the trash three times before the week was out. The lipstick was the expensive brand she painted his lips with while they nearly fucked in the men's room.

He couldn't get her out of his mind. More than once, as his wife rode him, through slitted eyes, he imagined it was Rachael he was inside of. And, as Olivia toyed with his ass, he dreamed it was Rachael preparing him. Eight inches, but a little skinny.

It was all pretext, of course. Even he knew that calling her to return her lipstick was an absurd excuse. Still, he refused to think about it. He held his cell phone open, her number on the screen, for long moments before hitting the send button.

tryst
tryst
63 Followers
12