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Dom TS Billy Bausch checked his very expensive gold Rolex as he turned off the highway...damn. He had come straight from the office and was still attired in his finely tailored suit, but due to the Friday rush hour traffic he was going to be fashionably late for the cocktail hour. At the age of twenty-seven, William Harrison Bausch III had it made, with a great executive position that he loved along with a $10,000,000 trust fund, he was already very financially secure. Not only that, but Billy had also been blessed with good looks, leaning more towards handsome than pretty, with a full head of fine blond hair, blue eyes, a gym toned body and a dimpled smile that made him a notorious ladies' man. Yeah, life was good. Billy pulled his Porsche up to the iron gate of the old Carson Estate and handed the guard his invitation. He chuckled to himself at the pretentious shiny gold stationery printed with fancy black font like it was a golden ticket to a magical place. Maybe it was...Billy had no idea what was in store for him this wonderful evening. Publicly, these exclusive "by invitation only" alumni events at the Carson Estate were just stale fundraisers for a university scholarship fund, but in reality this was a gathering of a select group of well-heeled perverts and kinksters for an evening of unbridled debauchery. Each event usually had a fetish theme; oral, anal, bdsm, watersports, age-play, rope bunnys, etc. but tonight was to be something special, a Sissy Boi Auction. Given how much he had to "donate" to get his golden ticket, Billy was expecting that this event, and the merchandise, would both be extraordinary. What was a good looking, well-heeled straight young man like Willliam Harrison Bausch III doing at such an event? In a word, "Boredom" ... Billy enjoyed breaking up his pampered, entitled lifestyle with the occasional thrill of indulging in some forbidden fruit. Except for a couple of drunken mutual jerk-off sessions with his frat bros, his sexual history had been totally straight, but tonight Billy would be crossing a line into engaging in gay sex. Sure, the mincing little gurl would be dolled up like a chick, but underneath the frills it would still be a dude sucking on Billy's big dick or taking it up her boi pussy. However, in Billy's head, fucking a sissy boi just seemed a lot less gay than fucking a dude. It didn't make sense, but somehow it did. The guard handed back Billy's invitation and waved him through the gate. The Carson Estate was an old Tudor style place with a dozen bedrooms that sat on about 160 acres and was surrounded by an eight-foot-high brick wall that provided excellent privacy from any nosy neighbors. Billy pulled into the courtyard where high priced cars were already parked, but instead of pulling in line with the other cars, he backed his little baby into the tight space between the garage and a tree where she would be safe from door dings. He loved this car that his parents had given him as a prep school graduation present almost more than life itself. He put his leather driving gloves along with his phone in the glove box and checked his look in the mirror one last time before he got out and headed for the main entrance with the confident stride of a young stud in his prime. The front door was open to the early night air, but as Billy approached, he saw that it was manned by another security guard. Having been here many times before, it was not a surprise when the guard waved a wand over him and asked if he had his phone on him. The rules were quite strict about NO recording devices or cameras being allowed on the premises in order to protect the privacy of the guests. "Hey, Charlie. Am I the last to arrive?" "Hey, Billy. No, we still have a few more coming," Charlie replied nonchalantly as he took Billy's golden ticket and crossed him off the guest list on his clipboard. "How's the food? I'm famished." "Great as always. I hear the lobster rolls are going fast..." "Thanks. I'll make sure to get some. Catch you later..." Billy headed into the living room and scanned the crowd, noting the usual suspects amongst the guests and also taking in the cute sissy boi/gurl merchandise. This was a very different scene than he was expecting. He had expected the sissy bois to be like something out of a drag show with exaggeratedly feminine acting twinks in heavy makeup, big longhaired wigs and outlandishly frilly outfits, but instead found normal acting college sissy bois sexily attired in female clothes with tasteful makeup, their actual hair nicely done up and for some reason they all were wearing tiaras like they were in a beauty contest. Billy smiled to himself. This was an auction, so you could say that was sort of like a beauty contest... In fact, there was one gorgeous sissy boi that was dolled up like he was in a beauty contest, in a red one-piece women's swimsuit and red heels with a sash over his shoulder that proclaimed ironically "MISS PERSONALITY". All the feminine sissy bois were decked out in what could only be described as sissy fantasy outfits. There were two maids, one in black and one in pink, a playboy bunny, a schoolgirl, cheerleader, nurse, meter maid, etc. Billy scored a lobster roll from the closest sissy boi...if you could call him that, or was it her? Either way, he/she was hot... a tall athletic black gurl with a ripped bod wearing a purple and gold belly dancer costume that left his washboard abs on full display. From bottom to top, his feet were in gold trimmed purple slippers, diaphanous purple harem pants permitted a view of his muscled calves and thighs as well as the purple thong that cupped his healthy bulge and cleaved his solid protruding buttocks, the short gold embroidered purple vest left his trim waist and solid pecs exposed, his full lips were painted a rich dark purple and his striking light brown eyes were lined in black like an ancient Egyptian. His dark mahogany skin made a perfect contrast to his golden tiara and the rings, bracelets and necklace that he wore. Sure, it was all costume jewelry, but on this Nubian stud they looked like a million bucks! Billy checked out her name tag as he took a bite of lobster roll, "Thank you, Sheba." Sheba smiled revealing white teeth and killer dimples. "Anytime, Sir," she replied coyly in a rich baritone that made Billy's knees turn unexpectedly weak. Thankfully she moved onto the other guests, but Billy found himself devouring his roll and swallowing hard while checking out her solid butt cheeks rolling hypnotically as she moved on... No way. Billy didn't think he could survive a night with a gal Sheba... Billy needed a drink. Now. He turned to a tall sissy holding a tray with flutes of champagne that had her back to him, giving him a chance to check out her discreetly. He admired her tapered waist that had a wide black belt around it, the perky butt that stretched her fingertip length red minidress becomingly and the sheer black seamed stockings that led down to four-inch red fuck me heels that had straps around her ankles secured with little red heart shaped locks. Her outfit practically screamed "SLUT". Nice...Very nice... Billy's revery was broken when she turned around and caught him checking her out. She seemed surprised to find him there and smiled, "Oh, hello... Who's little boi are you?". The normally confidant William Harrison Bausch III was totally flustered by her. "I-I'm Billy..." he stammered. She had found his Achilles heel. Billy was only five foot four inches tall and he was a little sensitive about his one shortcoming...to coin a phrase. "You look like you need a drink, little Billy," she smiled down at him as she held out the tray. Tawny, at Five foot eleven inches, made Billy feel like a little boi. He eagerly took a flute of champagne, "Thank you...Tawny." Billy said as he noted her nametag and quickly downed the contents. As he put the flute back on the tray, Tawny took a cocktail napkin and gently wiped his mouth. "You really did need that, didn't you little man?" she smiled. Billy noted that her lips and nails were painted the same deep crimson red as her dress and heels. Was she teasing him or flirting with him? Or both? Either way she was putting him off balance and he was at a loss as to how to respond. "I-I like your outfit..." he lamely responded to her taunts. "Well, thank you, Billy. Aren't you sweet? You look very nice in your little suit." The compliment had a lot of backspin on it. Billy pretended not to notice, "Thank you, Tawny." She offered him another flute and as he took it, she leaned in and whispered, "You can call me Mistress Tawny, my sweet little sissy boi Billy." "Thank you... Mistress Tawny," he whispered back. His big cock was rock hard in his boxer briefs. WTF?! He was flirting with a tranny and couldn't remember the last time he was this turned on. Tawny then took it up a notch. "Let me show you the bidding table, little Billy..." she grabbed Billy's bicep in a tight grip and steered him across the room. Blushing furiously and all too aware of how strong Tawny was, Billy submissively allowed himself to be guided to the table where the silent auction for the sissy bois was taking place. There was a bidding sheet for each gurl on the table and a glamour shot of how they were dressed this evening along with an earlier picture of them in their previous male persona. Billy could hardly believe that the smiling young college student in the photo was actually the smoking hot, intimidating gurl that still had a vicelike grip of his bicep. "Finish your drink, little Billy." She husked in his ear and squeezed his arm even tighter. "Yes, Mistress," he replied automatically and emptied his glass. Why did obeying her orders feel so good? "Good boy. Take another one and read the rules. I expect a generous bid from you Billy. Do NOT disappoint me." "Yes, Mistress Tawny." Damn... it even felt good to just say her name. Billy took another glass of champagne like a good boy and Mistress Tawny moved on to the other guests. Billy took a look at the rules. It was simple enough, take a room key, then fill in a bid for each gurl on the bid sheet by their photo along with your room number. At the appointed time they would announce the winning room number for each gurl. Billy grabbed a key. It was for room nine. He added the room number and a generous bid for Mistress Tawny. "Hi, Billy," He turned around to see a fellow perverted kinkster checking out the gurls' photos. "Oh, hi Phil. Should be an interesting night." "Oh, yeah. Umm, I would have thought that one of those sweet maids would be more your speed." "Well, the night is still young," then he noticed which sissy Phil was bidding on. "Sheba? Really...?" Phil gave him a wry smile. Billy smiled back, "You're a better man than I, Gunga Din..." Phil laughed and shrugged his shoulders. Billy noticed another familiar face approaching, "Hey Tom. Who are you bidding on?" Tom gave him a stern look, "Miss Personality over there. I want to spank that smirk off the little bitch's face..." Billy grabbed his glass and circulated among the crowd. He got a spring roll from Billy the pretty little blond in a black maid dress and an empanada from the other very cute maid Pink, who true to her name, was in a pink satin maid dress with a lock of her hair dyed pink. Maybe Phil was right, maybe he should bid on one of those pretty maids. "Another drink, little Billy?" Shit. Tawny was at his elbow again. It sounded to Billy like more than a suggestion. He took another flute of champagne. How many was this already? "Good boy. Drink up." She stood there expectantly. Billy drained the glass and put the empty on her tray. "Thank you, Goddess Tawny. my Mistress." She glanced down at the tray. Billy got the message and took a fresh glass. Christ. He had only been here a half hour and was getting buzzed from slamming champagne on a mostly empty stomach. He grabbed a spring roll from Miss Personality and decided that Phil was right, someone needed to wipe that smirk off the little bitch's face. Billy weaved through the crowd toward the auction table to put in a bid on Miss Personality and her spankable little bubble butt. He smiled at the thought of the squirming little gurl bent over his knee squealing for mercy as he spanked that curvy little butt until it was as red as her swimsuit. He got to the table and checked out her before and after photos. Damn, even as a boy he had that same smirk that made you want to smack him in the face. "What do you think are you doing, Billy?" a stern Mistress Tawny demanded quietly. Suddenly he was a bit more sober. Tawny took hold of his tie and led him down the table to her photo, "Do you realize that you have been outbid?" Billy looked through bleary eyes to see that he had indeed been outbid... Twice! No wonder Mistress was cross. "I'm sorry, Mistress Tawny..." Billy put his room number down and doubled his original bid. "That's alright, little Billy..." she soothed. Then with a conspiratorial look she added, "If you double that number again, you can have me for the whole weekend... all to yourself, sweet little boy..." Billy polished off his drink. Even for him, that was a lot of money... Tawny was tempting him like a devil on his shoulder, except Tawny was standing in front of him, holding onto his tie like a submisive's leash. "Just think about it sweet boy. Just you and me, little Billy... it's just a number... write it down and Mistress Tawny is ALL yours, ALL weekend. Do it little man, make Mistress Tawny happy..." Billy glanced down at the bid sheet and with trembling fingers, picked up the pen. "That's my good boy. Do it for Mistress Tawny..." Billy wanted so much to please her in that moment, that he did it. He bid a ludicrous amount of money for the company of a domineering gurl. "Oh, Billy. You're such a good boy. You've made Mistress Tawny so happy. Your ALL mine now...I OWN you for the weekend...ALL weekend." She gave him a quick peck on the lips, a swat on his butt, a fresh drink, and then went off into the crowd. Billy stood there for a moment staring at the bid sheet, feeling like a gambler who had just lost it all on one roll of the dice. Slowly it dawned on him that he hadn't so much bought Tawny for the weekend but somehow had sold himself TO her. He took another drink of his champagne and another treat from a passing sissy. What the hell just happened...? Ding...ding...ding... The president of the group got everyone's attention by tapping his glass with a fork like it was a wedding. "Attention everyone. The bidding closes in five minutes, so please get your final bids in now. Thank you." The crowd of perverts descended on the biding table like vultures. Billy looked around and noticed that some of the sissies were starting to look nervous. It had all been fun and games up to this point for them, but their gurly fates were to be sealed in the next five minutes. Billy was nervous too. Part of him was hoping beyond hope that he would be outbid for Tawny so he would be off the hook for the insane price she had pushed him to write down. But what if he lost? He would be going home alone and frustrated. Maybe he should bid on one of those very cute little maids while there was still time... "Last call, Billy boy..." Shit. Tawny was at his elbow again like a mean cat playing with a helpless little mouse. He drained his glass and took a fresh one. "In less than five minutes you'll belong to me for the whole weekend, little man...sissy boi" she whispered before moving on. Billy's big cock rose to full staff at the threat. He started to sweat as he saw people glance at Tawny's bid sheet, react in surprise and move on to another sissy. The hope for a last minute rescue seemed to be slipping away... Ding...ding...ding... "One minute, people..." Shit. Please...please...please... Ding...ding...ding... "The bidding is closed." There were some groans from those who had been outbid and giggles from the rest of the crowd. Billy had a sinking feeling in his stomach and considered making a run for it, but all too soon they were ready to announce the winners. Billy polished off the last of the liquid courage in his glass. "Before we begin, let's have our hostess for the evening who has generously opened her home to us for these shenanigans, Mrs. Emily Carson," Everyone gave the sweet old gal a round of applause as the president waved her up to the front of the room. "I think it only fitting that we bend protocol and announce Emily's winning bid first. Congratulations Emily, you placed the winning bid on Sissy Juliet!" There was a round of applause as a sweet little doe-eyed pantyboy in a poofy pink sissy dress minced forward on her Mary Janes and curtsied to her new owner. The crowd applauded and wolf whistled, making Juliet blush. Shit. I could have nailed that tonight Billy thought jealously... "Next up we have Tawny." Billy swallowed hard. There were wolf whistles and applause as Tawny stepped forward. "Tawny was by far our highest bid for the evening, and she goes to... Number Nine!" There was more applause, but in his head, Billy just heard the fateful echo of "Number Nine...Number Nine...Number Nine..." With a nervous smile on his face, Billy wove through the crowd to stand next to Tawny, who with a flourish took off her tiara and placed it on Billy's head, claiming him as her property. They looked like a prom king and queen as they took a bow before Tawny took him by the hand and led Billy away to his fate. "You are all mine, little Billy boy," she whispered in his ear as they left the room. Instead of taking him upstairs, Tawny led Billy towards the entrance where Charlie was still on duty. "Got my stuff, Charlie?" "Right here, Tawny," Charlie replied after giving a quick glance to Billy's tiara. He'd seen weirder things before on his job. He handed Tawny a gym bag and plastic grocery bag. "Thanks, Charlie. You're the best," Tawny smiled, handing Billy the gym bag, then leading him by the hand out the front door into the night. "You play safe..." Before Billy could say anything, Tawny asked, "Where's your car?" "By the garage." Tawny stopped and gave him a stern look. "By the garage, Mistress Tawny." "Better, slave boy." Billy felt a shudder of submissive pleasure race through his core at Mistress Tawny's comment. What neither of them knew was that the tiara Billy was wearing was specifically designed by Doc Dante to magnify any stimulation of the pleasure centers of a male's brain. Basically, any pleasure that a wearer would normally feel was cranked up to eleven! When Billy had arrived he was certain that a gurl would be sucking his big cock this evening............nope, Billy was going to be Tawny's cock sucker. Billy would be hooked for life and became a sissy boi, thinking about cock and yummy cum 24/7. |
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MMMMMMMMM lucky billy 
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