Sissy Auction 01: Billy buys Tawny

"See Billy... It matches your pretty panties and tiara perfectly!" Tawny almost squealed. Billy swallowed hard as she looped it around his neck under his open shirt collar and buckled it tightly around his neck.

"Th-Thank you, Mistress..." This was all going too far too fast...

But Tawny was quickly plowing ahead. She stood up before him in her boots before him and slipped on long black liquid spandex fingerless gloves that ran up to her mid bicep. She stood before him with her booted feet shoulder width apart with her hands on her hips, looking down at him triumphantly, "Like what you see, little man...?"

"Y-Yes, Mistress..." he replied weakly. He loved what he saw. A domineering Mistress in black; black boots, black stockings, black panties, black leather corset and black sleeved gloves standing over him and almost daring him to find some shred of manhood left in him to try to defy her. Billy had none...

She chucked Billy under the chin and ran her thumb over his red lips, "Time to give these dick sucking lips a test spin, Billy." She pressed her thumb against his lips and he yielded, allowing it to enter and sucking on it obediently. Tawny started sawing her thumb in and out of Billy's sucking mouth, "Yeah, you've got that sucking instinct, Billy. You're just a natural born cocksucker..."

"Mmm..." Billy gave out another involuntary moan of submissive excitement and sucked harder on Tawny's pumping digit.

"Sounds like you're ready for the real thing, girl," Tawny husked.

Tawny smiled down at him.

Billy knew instantly what was expected of him, but his straight boy brain was having trouble processing it. His new Mistress stood over him with hands on hips, expecting him to give her a blowjob like some faggot cocksucker. What scared Billy and gave him pause was the sudden realization that he would be crossing a line from which there was no going back. He would be a cocksucker. He would be Tawny's cocksucker for the rest of the weekend. Even if he never sucked another cock ever again, for the rest of his life he would remain a cocksucker.

Billy flashed on the image of Scrooge seeing his tombstone and imagined his own epitaph.

HERE LIES

WILLIAM HARRISON BAUSCH III

PANTYBOY AND COCKSUCKER

REST IN PANTIES

Tawny sensed Billy's hesitation and smiled down at him, admiring how pretty he looked with his handsome face made up. "Don't worry, Billy," she said as she reached down and cupped Billy's chin, "I'll walk you through it." Her cock rose to full hardness in her panties at the sight of Billy kneeling before her in his pink panties and black stockings. Tawny inched forward so that the bulge in her panties was an inch from Billy's red lips. Her hard cock twitched in her panties when she felt her boytoy's warm breath on her dick through the thin fabric.

Billy was so close to Tawny's hard cock that the scent of her perfume was overwhelmed by the masculine scent of Tawny's cock and feel the heat emanating from her turgid equipment. He involuntarily licked his lips and swallowed the extra saliva his mouth started producing in response to the proximity of a hard cock. He glanced up nervously, taking in the sight of Tawny's trim body before their eyes locked.

"Kiss it," Tawny ordered quietly while looking down at him. "You know you want to..."

Billy wasn't so sure about that. He had a lot of plans for this weekend and none of them included kissing a tranny's cock through her panties. But Tawny had a firm grip on the ends of his tie looped around the back of his neck and pulled him forward gently. The young executive puckered his red lips and closed his eyes...as he was pulled inexorably forward until...

CONTACT!

Billy had kissed the pantied crotch of many a young lady, but the sensation of feeling a hard cock beneath the thin fabric was a weird and erotically charged experience. Tawny moaned above him at the contact, encouraging Billy to continue. He smooched the length of the nylon clad cock with renewed vigor, pressing harder with his lips, slipping his tongue between them to apply a series of wet kisses to the length of Tawny's hard cock. "Now you're getting with it," Tawny enthused. "Take it out, Billy...Take out my cock."

Billy lifted the leg opening to Tawny's panties, releasing her hard cock. It slid across his cheek as it sprang free, leaving a trail of glistening pre-cum. Billy backed off in surprise, until Tawny's grip on his tie held him in place. Swinging her hips, Tawny playfully slapped her hard cock on Billy's face, leaving trails of pre-cum on his cheeks and forehead. Billy gasped in both humiliation and excitement as he felt the weight of a warm meaty cock slapping his cheeks and forehead over and over until Tawny pressed her cockhead against Billy's lips.

"Open up, little man," Tawny demanded quietly, pulling on his tie, increasing the pressure on the back of his neck. "Open those pretty dick sucking lips for Tawny..."

Billy looked up and held Tawny's gaze as he slowly complied with her desires. He could hardly believe what he was doing. Billy was opening his mouth to suck on another dudes' cock! He couldn't believe his own actions. What was it about Tawny that caused him to surrender to her so completely? Billy had bought her fair and square at the sissy auction, so why wasn't she on her knees sucking his cock? But those questions were about to become academic...

Billy's lips parted and for the first time in his life, he willingly yielded entry to another man's hard cock accessing his oral cavity. Billy experienced the new taste and sensation of a cock in his mouth as he wrapped his lipstick coated lips around it and tentatively bobbed his head forward, his cheeks hollowing as he applied suction to the hard cock, making his new status official.

Billy was now a cocksucker...

A pantyboy cocksucker...

The thought made him moan around the cock in his mouth while his own painfully hard cock jerked in the confining nylon prison of his new pink panties. He grabbed Tawny's panty clad ass and used it as leverage to pull himself deeper onto his Mistress's hard cock. The feel of creamy but solid girlyboy ass in nylon panties combined with sucking on the big dick in his mouth was pure ecstasy.

If he was going to be a cocksucker, Billy was determined to be a good cocksucker. He wanted to please his new Mistress with every fiber of his being. He assaulted her cock with every oral trick he had ever received from an endless line of skanks that had sucked on his cock over his lifetime. His new mission in life was to please Mistress Tawny.

Above him, Tawny let out a moan of "Fuck...Yeah..." the moan spurred by the sensations of Billy's hot mouth sucking her cock and Billy's hands kneading her pantied ass. The sound of Tawny moaning in pleasure encouraged Billy to step up his efforts. He bobbed his head faster, sucked harder, applied more pressure with his swiping tongue on the big cock in his mouth and took the liberty of exploring more of Tawny with his kneading hands. He explored her lower body, squeezing her jerking butt cheeks and running his hands down the backs of her silky stockinged thighs and the upturned muscles in the back of her calves. Billy was rewarded with more animalistic grunts and moans from the pantyboy standing over him who he was reducing to an animal in heat.

Tawny was getting close above him and Billy ravished her with his mouth and hands until he felt the panty clad young tranny grab his head and stab her cock deep into his throat. Tawny moaned out her orgasm while Billy grabbed her pantied ass and pulled her in to get every inch of her spasming cock down his throat. His tongue and sucking mouth milked every last drop of Tawny's cum out of her softening cock and down his throat, draining the essence of the satiated and momentarily helpless pantyboy above him who had to hold onto Billy's shoulders for support as her knees buckled from the intensity of her orgasm.

His fate was now sealed.

Billy was now a cocksucker...

He kept sucking on Tawny's softening cock like he was nursing, drawing every last drop of semen into his mouth until she recovered and withdrew. "Wow. You really are a natural born cocksucker, Billy," she gasped and patted his cheek.

"Thank you, Mistress," Billy panted in reply. He had done it. He had sucked another dude's cock and swallowed his sperm. Billy's stomach flip flopped at the thought. Now that the passion had passed, he was left with shame and guilt, along with a sour taste in his mouth. But there was no time to dwell on it.

"Oh, Billy. What a mess you made..." Tawny yanked off his dress shirt and used it to wipe the mix of sperm, saliva and phlegm from his chin and chest. Billy just knelt there in his family room in his tiara, panties and stockings, passively allowing his new tranny mistress to apply a fresh coat of deep red to his swollen lips.

"Sorry, Mistress," Billy apologized. He wasn't sure why he was apologizing for having made a mess while sucking her dick, but it just came out in response to being scolded.

"That's alright sweety. Just stand up for Tawny." Billy got up on his stockinged feet but froze when Tawny held open her red dress for him to step into. This was all going too far...Billy wasn't into dressing up, but Tawny seemed determined to doll him up like a sissy. "Put your feet into your dress, Billy," Tawny ordered with a tone that sent a shudder through the young man.

Billy lifted his stockinged right leg and stepped into the red micro dress. He inhaled at the erotic sensation of the soft material sliding over his stockinged leg. He followed with the left leg and was rewarded with another erotic rush of his stockinged legs sliding against each other and the dress material at the same time. Before his brain could even process these sensations, Tawny started to slide the dress up his thighs, pulling it up over his butt, putting his hands through the arm openings before pulling it up his torso until the cap sleeves rested on his shoulders. She turned him around and slowly zipped up the back of his dress. A glint caught his eye and he saw himself reflected in the dark screen of his plasma TV as through a mirror darkly, the tiara on his head and the pink collar around his neck sparkling with his every movement while below he saw a now almost pretty young man with his face made up wearing a red minidress and black stockings. As he felt the zipper being slowly drawn up his spine, pulling the dress tighter around him, Billy felt like Tawny was imprisoning him in the dress as she zipped him up until he was trapped. Tawny grabbed the wide black belt and pulled it tightly around his midriff like a corset before buckling it shut.

"Oh, Billy. Your butt looks amazing in that dress," Tawny enthused as she groped his pantied ass through his skirt.

"Th-Thank you, Mistress..." Billy hated how lame he sounded, but he couldn't seem to stop himself, "I'm glad it pleases you, Mistress."

Tawny stepped closer behind him as she continued to knead his buns with both hands and brought her lips to his ear. "Oh, it pleases me, Billy," she husked. "Your butt is going to please me all weekend, my little Billy." She nibbled his earlobe...

"Oh, yes, Mistress," he moaned in response to Tawny chewing on his ear, but he was aware that he had not only just agreed to surrender his anal virginity to her, but he had also offered up his butt to her for the entire weekend.

"Let's get you into your shoes..." Tawny almost threw Billy into the chair and grabbed her red high heels off the floor. "Give me your foot," she ordered and after a moment's hesitation, Billy nervously extended his stockinged foot to his Mistress. She immediately started to cram his foot into her four-inch red heels. There was no way he would be able to walk in these shoes, but there was no going back once Mistress Tawny got his foot in and then buckled the ankle strap closed. He was about to protest when Tawny locked the strap securely around his ankle with the little red heart-shaped padlock that now dangled over his heel. Billy sat there helpless to resist as Tawny locked his other foot into the ridiculously high heels.

"Don't you look just precious..." she teased. Then Tawny noticed her nametag still attached to his dress. With an evil grin she slid the cardboard out of the tag and with an eyebrow pencil from her bag, wrote on the back side before sliding it back in. Billy looked down at his nametag and saw that Tawny had christened him as "Billie" with little hearts dotting the I's.

Great, now she's feminized my name, too...

"On your feet, Billie..." she smiled down at him and held out her hands. He clasped her hands and she helped him stand up on the four inch heels strapped to his feet. He experienced a slight wave of vertigo as he rose to a brand new height. So this is how a six foot tall dude sees the world...

"Remember to take small steps, Billie..." Tawny instructed as she took a step back. Billy almost tumbled on his first step and he silently cursed the amount of champagne he had imbibed earlier. After Tawny guided him through the first few steps, Billy found himself getting the hang of the heels once he stopped fighting them and just went with it.

Tawny admired how his butt swayed when he walked away from her, "You've got the hang of them now, Billie. Work that moneymaker, girl!" Billy blushed deeply as he realized that he was swishing like a drag queen as he minced across his family room with hips swaying, his butt jutting out invitingly while he walked with his elbows bent to help his balance like a limp wristed fairy. What really concerned the cross-dressed stud was that he was enjoying it. He was enjoying being Mistress Tawny's little sissy Billie...

"Let's take this into the bedroom, little Billie," Tawny husked as she picked up her bag and took a firm grip of his bicep. He started walking down the hall, leading the way but Tawny's grip on his arm left no doubt who was in control. As they walked down the hall, they passed pictures of Billy in what was now quickly becoming his past life. The pictures of the smiling young man enjoying kayaking, skiing, dirt biking, fishing and other macho activities seemed to be mocking the young sissy as her Mistress steered her to her fate.

They entered the master bedroom suite which was furnished with heavy dark masculine style wood furniture, including a four-poster bed with a heavy headboard and footboard. Billy had screwed a lot of gals on that bed in both vanilla and kinky scenes. Tonight, he would find himself on the receiving end of a very kinky scene. Billy froze when he caught his reflection in the dresser mirror which he had strategically placed opposite the bed. He thought he looked both ridiculous and sexy as hell at the same time.

"See what a pretty little girl you make, Billie..." Tawny cooed in his ear like an evil angel.

"Yes, Mistress," he readily agreed.

"You want to be my pretty little girl, don't you Billie?" Tawny asked as she patted his bottom.

"Oh, yes, Mistress..." he volunteered himself, not believing the words coming out of his mouth, but he was transfixed by the image in the mirror. He wanted so much to be a pretty little girl for his Mistress.

"That's my little Billie. Climb up on the bed like a good girl." Tawny ordered as she slid open the mirrored closet door and busied herself looking for something.

Billy climbed up on the bed on his hands and knees like a good girl, watching his reflection in the mirrored doors and finding it hard to believe that the pretty sissy kneeling on his bed was actually him. Tawny slid his closet door shut and approached him with a handful of his ties. She had selected not only his narrowest ties, but some of his most expensive designer ties as well. He cringed at the thought that they would likely be ruined and he mentally added it to the tally of just how expensive this tryst with Mistress Tawny was getting to be.

"Kneel here and put your hand out," she ordered pointing at the footboard. Billy shuffled forward until his knees were against the footboard and extended his fist. Tawny looped the silk around his wrist and tied it tightly. "Comfy?" He swallowed and nodded silently. She then secured the other end of the tie high up on the bedpost but left a good amount of slack. Billy started to get nervous as she did the same to his other arm. With his arms secured, he was truly at her mercy and a dozen different nightmare scenarios flashed through his mind. Tawny looped another tie around his ankle and then tied the ends over the top of his stockinged thigh securing his ankle to the back of his leg. Once she had done the same to his other leg, Billy was trapped in a kneeling position with his butt on his heels and his arms secured to the posts of his bed. Instinctively, he tested his bonds and found that there was a good amount of slack in the ties securing his wrists but not enough for him to be able to reach either of the knots on the posts. He suddenly regretted having invested in a king-sized bed where the posts were more than six feet apart. His breathing and heart rate increased as Billy experienced the submissive side of bondage for the first time in his privileged life.

Mistress Tawny chucked him under the chin and smiled down at him, "You've been a very good girl tonight, little Billie."

"Thank you, Mistress..."

"But you have challenged my authority several times this evening." Billy swallowed hard and his arms tested his bonds again. "You bid on another sissy at the auction without my permission, you did not freely surrender your car keys to me, you hesitated to pleasure my cock with your sweet mouth and hesitated to step into your Mistress' pretty dress rather than accepting it as the honor it is to wear anything that has touched your Mistress."

"I-I'm sorry, Mistress..." Billy almost whined.

"Shh... I know you are, little Billie. However, discipline must be maintained." Mistress Tawny reached down and unbuckled the wide black leather belt from around his midriff. She stepped back and posed with one hand on her hip and let the belt dangle menacingly from one finger of her other hand through the belt buckle. "How many lashes do you think you have earned?"

Lashes...? Was she serious...? Billy tried to respond but even as his mouth opened and closed, no sound came out. He had no words...

"Let me give you one so you know what you're in for, Billie. Stick that spankable butt up in the air for Mistress Tawny..." With his legs bound, the only way for Billy to present his ass to his Mistress was to lean forward over the footboard. Tawny stepped to the side and Billy heard the belt slice through the air and slap his upturned butt...HARD!

"FUCK..." he groaned. The lash stung. Billy could swear that he actually felt the belt contour itself on impact to every curve of his perky butt cheeks.

"Language young lady, language," she remonstrated. "Now how many lashes like that one have you earned this evening?"

OMG. Billy didn't want ANY lashes like that one, but he had to give Mistress a number. He knew better than to lowball it... "Twelve, Mistress..." The number sounded PAINFULLY high to him as soon as he said it...

"Are you certain, little Billie?" she asked all too sweetly.

Billy knew how this game was played. He had to beg for it... "Yes Mistress. Please give me twelve lashes on my sissy ass so I can be a good girl for you... Please Mistress... Make me into a good little sissy girl..." What unnerved Billy was that as soon as he started speaking, he meant every word with every fiber of his being...

"That's my girl," Tawny ran a hand gently over his sore buns and raised his skirt so she would have a clear shot at his pink pantied ass. With a sob, Billy leaned forward to present his nylon clad butt to his Mistress for discipline. He heard the belt coming...