Sissy Auction 01: Billy buys Tawny

Tawny led him to the trunk of his car and had Billy open it and put the gym bag inside. Then she took his keys from him and held open the passenger door for him, "Get in, Billy." It was weird on so many levels; having a girl hold open a door for him, getting into the passenger seat of his own car, letting someone else drive his baby. Seeing his hesitation, Tawny explained, "You're in no condition to drive."

"Oh. You're right, Taw-Mistress Tawny..."

"Hold that thought."

Billy got into his car and sat down.

Tawny leaned down, "Buckle up, Billy. It's going to be a bumpy night." She closed the door and Billy buckled up while Tawny walked around the rear of his car. As she got in on the driver's side the interior light came on and Billy was treated to an unobstructed view of her long stockinged leg in red pumps. Damn she has hot legs, he thought. I'd love to spread them and bury my face in there. Then he thought, dude, she's a guy...

Tawny had to slide the seat back to make room for her long legs, reminding Billy of his shortcomings in the height department. Ouch. She started the car and dropped the plastic bag in his lap, "I had chef make something for you." Billy opened the bag, finding napkins, a bottle of water and a clamshell doggie bag. He popped it open and discovered a grilled chicken sandwich on a bun, steak fries and ketchup...Real food!

"Tawny, I love you!" he blurted out.

She turned, smiled and chucked him under the chin, "I love you too, little Billy." Then she leaned in and kissed him on the lips. Billy felt her tongue press against his lips and he yielded, allowing her entrance. Tawny pressed her advantage, taking full possession of his mouth while her hand gripped his jaw tightly. Their tongues dueled with passion and the hot meal in Billy's lap lifted noticeably as he enjoyed his first makeout session with another male. For the first time in his life, Billy found himself in the sexually submissive role and he was loving it. Tawny's strong grip was as exciting as her demanding tongue exploring every surface of his oral cavity. Somehow, he found the courage to reach over the console and stroke her stockinged thigh. Mistress Tawny moaned encouragement into his mouth and he moaned back in response. Her thigh felt amazing through her silky stocking and Billy tried to press his tongue into her mouth, but she nipped him playfully with her teeth and he relented, submitting completely to her assault.

Sadly, she withdrew and started the car.

"Wow..." Billy panted.

"Put your address in your phone," Tawny instructed as she adjusted the mirrors.

"Yes, Mistress..." Billy fired up the GPS and the woman's voice directed "Turn left.."

Tawny put the car in gear and pulled out of the courtyard through the main gate and made a left, while Billy cringed at someone else driving his baby. "Eat your sandwich like a good boy."

"Yes, Mistress..."

"You really love this car, don't you, Billy?"

"Umh - hmm," he swallowed. "It was a graduation present from my folks."

"Poor Billy. Does everything you have come from Mummy and Daddy?"

OUCH! That stung. Mainly because Billy knew it was true. The car, his Rolex, the downpayment on his house, the connection that got him his cushy job...they all came from mom and dad. Tawny had a talent for finding all the kinks in his armor and making him feel small and vulnerable. Why was that turning him on...?

"Yes, it does, Mistress..." he confessed.

"My poor little man," she patted his thigh in sympathy as he finished his sandwich. "it sounds like you've been training to be a boy toy your whole life." Then Tawny surprised him by gently taking his hand and putting it on the gearshift under her hand. He could feel the vibration of the road as her thumb gently stroked his hand.

Maybe it was the champagne talking, but the words just came out, "I want to be your boy toy Mistress Tawny."

She smiled at him and squeezed his hand, "That's my sweet little Billy."

They drove in silence the rest of the way, simply enjoying being with each other and holding hands. As they entered his neighborhood, Billy started to get nervous. Not about the neighbors spotting him in a tiara and holding hands with a tranny, but that his secret kinky life was about to spill over into his vanilla existence. Once that door was opened, there would be little chance of ever closing it again.

As they pulled into his driveway, Billy hit the garage door opener and Tawny pulled his car inside. "You can breathe now, Billy," she teased as the door closed. "Your baby is home safe and sound."

"Thanks, Tawny," he smiled.

"Now stay," she ordered as she got out of the car. He watched with admiration as Mistress Tawny walked like a cat on the prowl around the front of his car, passing his kayak, skis, golf clubs, all the relics of his former life as a self-confidant young man. She reached his door and looked down at the handsome young man in his expensive tailored suit with her tiara in his thick black hair. She smiled at her prize and opened the door for him, "C'mon out, little Billy."

Billy meekly got out of his car. Tawny had set the tone for their weekend together. This might be his house, but she was the one in charge. She grabbed him by his red silk power tie and pulled him close. She towered a head higher than Billy in her heels, enhancing her authority over him. She leaned down and kissed him gently on the lips before leading him by his tie over to the door that led into his house.

Billy punched the code on the alarm and they went inside. His heart was beating in his chest as they entered into his living space. Things were about to get real as Billy's kinks breached the walls of his white bread world. They stepped into his family room.

"Do you have any wine?" Tawny asked.

"Y-Yes, Mistress."

"Fetch me a glass like a good boy, Billy," she smiled as she squeezed his right butt cheek possessively and then gave him a pat to send him on his way.

"Oh, red or white, Mistress?" Billy asked as he opened his wine fridge.

"Red," Tawny replied as she eased herself into Billy's favorite easy chair. Billy opened the wine and turned the radio on to a light jazz station. When he returned with her glass, she handed him the car keys, "Be a good boy and get my bag out of the trunk."

"Yes, Mistress." Billy took a deep breath as soon as he stepped into the garage. What have you gotten yourself into, Billy? What are you gonna do with a tranny in your house the whole weekend? What if she doesn't leave...? He didn't want to follow those thoughts any further. He could get in his car and leave...No, Tawny had poured more than a bottle of champagne into him one glass at a time over the last hour. The last thing he needed was a DWI. Billy got the gym bag out of the car and took a deep breath before he went back inside.

Tawny had taken her shoes off and sat curled up on his chair. She reminded Billy of a plotting cat eyeing a wary mouse. "Just put it here, Billy boy," she pointed next to her chair. As he put it next to her, Tawny smiled up at him from her wine, "Why don't you show me my new toy...?"

Billy got her drift. She wanted him to strip for her. Billy blushed as he took off his suit jacket and hung it over the back of a chair. Next, he kicked his shoes off then unbuckled his belt, undid his fly and stepped out of his slacks. After he draped them on a chair, he stood a bit defiant in front of Tawny with feet shoulder width apart, unbuttoning his cuffs and completely loosening his tie, letting it hang around his neck. As he started to slowly unbutton his tailored white shirt, Tawny teased back by licking the edge of her wineglass. Billy was glad that he had manscaped before the auction as he revealed his sculpted torso to her. Tawny beckoned him closer with a finger... Billy took a step forward and she put her wine down and grabbed the ends of his tie. He leaned down until his hands were on the arms of the chair and she kissed him again, pushing her tongue into his mouth while her hands explored his gym toned body, tweaking his nipples, tracing his treasure trail over his abs until she cupped his bulge in his black boxer briefs. Billy moaned into her mouth in pleasure as handled his goods. She broke the kiss...

"Kneel."

"Yes, Mistress Tawny," he husked before lowering himself to his knees on the carpet before her and lowered further until he was sitting on his heels.

Tawny playfully slipped her stockinged foot into Billy's open shirt front and ran the ball of her foot over his chest, teasing his nipples with her toes before tracing his treasure trail down to the tent in his boxer briefs. She was enjoying the view of the handsome young executive on his knees before her. The tight bodied little man had just the right amount of manscaped body hair in all the right places, including the short stubble on his jawline. Billy smiled up at her revealing a set of killer dimples, she admired his high cheekbones, blue eyes and thick black hair still topped off with her tiara. Damn he was cute she thought. Tawny saw a lot of potential in little Billy.

She lifted her foot, "Give me a nice footrub, Billy."

"Yes, Mistress," he smiled his dimples at her as he took her foot and massaged her sole deeply with his thumbs.

"Mmm, that feels so good," she took a sip of wine while she used her free foot to explore his torso.

Billy was loving this. Tawny was enjoying having her foot massaged and Billy was loving the silky feel of her other stockinged foot sliding over his chest and teasing him with her toes felt amazing. She pulled her foot away from his hands and switched feet. Billy massaged her other foot and extended the massage to her calve.

"Mmm, do you like my stockings, Billy?" she purred as she took another sip of wine.

"Oh, yes, Mistress. They're so silky smooth and your long legs look great in them," he enthused as he rubbed her foot and calve.

"Then I've got a treat for you," she gently pushed on his chest with her foot, forcing him to lean back until he was on the carpet before her on his back and elbows.

Billy watched with trepidation as Tawny put her wine down and opened the mysterious gym bag. She rummaged around for a moment and then pulled out a small packet. She looked down at Billy with a Cheshire cat grin as she opened the packet and pulled out a pair of shiny opaque black stockings.

Seriously? She had to be kidding. Billy had never worn ladies' stock...well, ladies' anything before. Not that he had anything against crossdressing. He thought Tawny was smoking hot, but trying it himself was a kink that had just never crossed his mind. Apparently, that was about to change. Tawny was already rolling up one of the stockings on her hands in preparation of putting it on him. With a mental shrug, Billy obligingly held out his foot for her.

"You really never have tried this before, have you?" Tawny giggled. "Point your foot like this," she demonstrated with her own stockinged foot. Billy complied and pointed his foot at her and she rolled it over his foot then started to work it up his calve. It felt nice...really nice. It felt even better when she ran her hand over his nylon clad calve to smooth out the stocking. As she worked it past his knee and up his thigh, Billy was a bit surprised at how nice his leg looked in the shiny black stocking. "Feels good doesn't it, little Billy?" Tawney asked as she rolled up the other stocking.

"Oh, yes, Mistress..." Billy almost gasped as he pointed his other foot at Tawny eager for her to stocking that leg too. Billy laid there on his elbows allowing Mistress Tawney to encase his legs in ladies' hosiery. He knew how great stockings felt on a girls' legs but he had no idea how awesome they would feel on his own legs. Then when Mistress started rubbing her stockinged feet on his nylon clad legs he actually let out an involuntary moan, "Mistress Tawny, that feels amazing..."

"Get up here and sit in Mistress Tawny's lap, little man," she ordered. The scene would be emasculating for Billy, but the truth was that Tawny couldn't resist getting her hands on the hot little stud. Billy didn't need to be told twice.

"Y-Yes, Mistress Tawny," Billy readily agreed and scrambled to his feet. As soon as he stood up, Tawny wrapped an arm around his waist and with the other under his knees, swept Billy off his feet and sat him on her lap. Billy had never been manhandled before, but he loved the feeling of being overpowered. Before Billy could even react, Tawny was on him like a quarterback on a cheerleader at homecoming. Tawny kissed him deeply, practically devouring him while stroking his stockinged legs. Billy kissed her back passionately, thrilling to the silky feel of her stockinged legs on the back of his thighs and the sensuous feeling of their nylon clad legs sliding against each other. He was also enjoying the new sensation of being the object of someone else's unbridled desire. Tawny was pawing at him passionately, kneading his butt, exploring his chest and taut abs, exploring every available inch of her new toy. She was loving how easily Billy was sliding into the role of a submissive. The poor boy had no idea how far he would slide this weekend under Tawny's tutelage.

When they finally came up for air, Tawny noticed that some of her lipstick had rubbed off on Billy's lips. "Let's make you pretty, Billy," she husked as she grabbed her gym bag and rummaged a moment for her makeup bag. "Oh, look! These will be perfect for you," she pulled out a pair of hot pink full nylon panties along with her makeup bag. "Stand up and get out of those nasty boxers, Billy." Billy would have hesitated, but Tawny easily lifted him off her lap and stood him up. He had no desire to humiliate himself by putting on girls' panties, but he already knew better than to defy Mistress Tawny.

OMG. Could he get any more adorable? Tawny thought as she watched Billy shyly turn his back to her as he pulled down his black boxer briefs and for the first time in his life, stepped into a pair of ladies' panties. The nylon felt amazing as it slid up his stockinged legs and great on his butt as Billy pulled them up first in back then in front. The soft material gently cupped his cock and balls when he pulled the pink nylon panties into position in the front.

"Don't be shy, Billy. Show Mistress Tawny your pretty panties," she taunted playfully. A blushing Billy worked his way a bit deeper into Mistress Tawny's heart when he shyly lifted his open dress shirt by the tails to show his new Mistress his pretty pink panties. To Tawny it was a classic sissy move, as if Billy was about to curtsey for his Mistress. She also found it deeply ingratiating. Tawny reached out and ran her hands over Billy's pantied rear and front. She felt him shudder with pleasure at the contact and smiled as her boytoy succumbed to a newfound fetish for wearing ladies' panties. Billy would make an excellent pantyboy. Tawny would see to that.

"Sit down, Billy," she ordered and without hesitation, Billy sat at her feet and looked up at his Mistress like an expectant puppy. "That's my good little pantyboy." Billy blushed. "I don't want to take a chance on ruining my dress," Tawny said with a gleam in her eye as she stood up and turned her back to Billy. "Unzip me," she ordered.

Billy reached up with trembling fingers and grasped the zipper between her shoulder blades and slowly lowered it down Tawny's back, revealing the tightly cinched black leather corset beneath, solving the mystery of her tapered waist. Tawny slipped the dress sleeves off her shoulders, then with a gentle tug at the hem, her saucy red minidress slid down her frame and puddled at her ankles. Billy finally got to see the parts of Tawny that until then had only existed in his imagination. The angular shoulders suggested masculinity but below that the leather corseted narrow waist flared out slightly to her teardrop shaped butt cheeks framed perfectly in black nylon high cut panties with scalloped trim at the leg openings where just a suggestion of bare skin before the seam of her black stockings traced down her long legs to her heels, leaving an overall impression of nothing but delicious femininity.

Billy had to fight the urge to bury his face in the crack of her nylon clad ass and settled for drinking in the sight of the sexy rear view of his new Mistress. Tawny turned around and Billy found himself at eye level with the healthy bulge in the front of her panties. "Like what you see, little man?" she teased with her hands on her hips. Billy looked up at her and blushed furiously.

Tawny smiled and sat down. "God, I love teasing him," she thought, "he's even more adorable when he blushes." She took a compact and a tube of liquid lipstick from her makeup bag. Using the compact mirror, she checked her look and then popped open the lipstick to touch up her deep red lips after their make-out session. As he watched her sensuously running the tip over her lips, Billy unconsciously licked his own. "Wait your turn like a good boy, Billy," she teased.

What? She had to be kidding. Billy didn't want to wear lipstick any more than he'd wanted to wear panties and stockings... What if he enjoyed it as much as he was enjoying the lingerie? But before he could object, Tawny put her arm around his head and cradled it like it was a football with her hand gripping his jaw. He looked up into her eyes silently pleading, but when he felt the applicator touch his lower lip he broke eye contact with her and glanced around nervously as he suffered the humiliation and emasculation of the involuntary feminization of his handsome face. He felt like his masculinity, his identity, was being erased with each swipe across his lower lip. Billy started to sweat.

"You have such sweet lips, Billy," Tawny cooed as she moved on to his upper lip, "You have such a nice cupid's bow, perfect for sucking cock." Billy was drawing in quick ragged breaths, a warning that his flight response was kicking in, but Tawny had already finished painting his lips so they matched hers. "So pretty..." she cooed, admiring her handiwork. "But we have to wait for those to really air dry. Let me help you with that, Billy..." She leaned over him like a sexy vulture and gently blew on his moist red lips. It was so wickedly sensual that Billy let out a soft submissive moan and squirmed in his panties at her feet.

For the next twenty minutes, Billy endured having his eyes lined in black, red eyeshadow applied to his lids and even had to suck in his cheeks to allow Tawny to apply blush to his stubbled cheeks. Finally, she presented him with the compact mirror so he could see her handiwork. Billy was stunned at what she had done to him. He had been expecting an over-the-top drag queen makeup job, but Tawny had actually made him pretty, accentuating what he already had and highlighting his lips, cheekbones and deep-set blue eyes.

Billy felt like it was a different person looking back at him from the mirror, a prettier, more sensual and decidedly less masculine version of himself. He had indeed been erased.

"I told you I was going to make you pretty, didn't I little Billy?" she cooed in his ear.

"Yes, Mistress..." he almost gasped. Even his voice sounded different...softer, gentler.

"You want to be pretty for me all the time, don't you, Billy?"

"Yes, Mistress..." It was true. He wanted to be pretty for her... and himself.

"Good boy..." Tawny brought their painted lips together for a quick gentle kiss. Billy moaned in response. Tawny pulled away and smiled, "I have something special for you." She reached into her bag of tricks, searching for Billy's gift, but found something else...a pair of patent leather ankle boots. "Slip those on my feet, Billy..." While she continued to dig in the bag, Billy slipped the shiny black boots on her feet, admiring the pointy toes and three-inch heels as he zipped them up. "Here it is!" Tawny excitedly held up something pink and sparkling, a rhinestone encrusted pink dog collar...