Ballroom Affair

by Tryst

Copyright© 2013 by Tryst

Erotica Sex Story: A high-end fundraiser changes a man's life

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/Ma   Consensual   TransGender   CrossDressing   Fiction   Cheating   Oral Sex   Anal Sex   Fisting   Body Modification   Transformation   .

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?"


"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.

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.

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