Sissy Auction 01: Billy buys Tawny

"One, Mistress." Two! He should have started on two since she had given him a taste... too late now...

"Two Mistress." Billy leaned even further over the footboard, trying to lessen the impact of the lashes.

"Three Mistress. Four Mistress." Billy's ass was starting to burn... maybe Mistress would show mercy...

"Five Mistress. Six Mistress." Halfway there, he could do this...

"Seven Mistress. Eight Mistress. Nine Mistress." His voice started cracking... it was all too much...

"Ten Mistress..." Billy sobbed, he was leaning fully over the footboard now with him arms painfully outstretched behind him like an obscene hood ornament. Only two more...

"Eleven Mistress. P-Please Mistress." Please take one off for the test lash...please...

"Tuh-Twelve, muh-Mistress Tawny. I did it. I took twelve like a good girl, Mistress..." Billy babbled.

Tawny moved to him and wrapped her arms around him, "Good girl...That's my good little girl..." she cooed in his ear as she petted his back.

"I did it Mistress... I did it..." Billy babbled like a proud toddler.

"That's my sweet little Billie. Mistress Tawny is so proud of you..." she whispered seductively in his ear. "Mistress Tawny is going to claim you now."

Billy knew exactly what she meant...and he was ready.

Mistress Tawny broke their embrace, grabbed a bottle of lube and a towel from her bag of tricks then climbed on the bed behind her new sissy. She pulled Billie's pink panties down over his bright red ass mounds. Poor little thing, his butt was going to be sore tomorrow. Tawny would have to apply some lotion and an ice pack, but that would have to wait. She filled a syringe with lube, then after loosening Billie up with her thumb, she injected a healthy dose of lube up his virgin canal. The procedure may have been almost clinical for Tawny, but it was far more traumatic for Billy...

Billy felt the bed sag behind him as his Mistress climbed onto the bed. She was going to fuck him. He glanced up at his reflection in the dresser mirror before him, noting the defeated male wearing women's clothes, makeup and a tiara. Once Mistress Tawny took his anal virginity his transition to being a sissy boy would be complete.

Behind him he felt his panties being pulled down and drew a quick intake of breath at the sensation of cool air on his burning bottom. Then he felt Tawny's lubricated thumb gently circling his most private spot. It was actually a pleasant sensation until Tawny suddenly pressed forward and her thumb popped inside, breaching his anal ring. Billy bucked forward as much as his bonds would permit, but it was pointless, Tawny's thumb remained lodged up his rectum and started to massage his prostate.

"Just try to relax, girl," Tawny advised soothingly as she started to saw her thumb in and out.

Billy flashed on how many girls he had used pretty much the same line on when he breached their virgin bottoms in this very bed. If they could only see him now they would throw his words back at him while laughing hysterically at his situation.

He tried to relax but the sensations were so unfamiliar that his brain was having problems processing what was happening. There was a feeling of fullness that caused an instinctive reaction to clamp down painfully to expel the intruder, but it kept moving in and out while pleasurably massaging his prostate. Finally it withdrew, leaving Billy panting in relief until he felt something cool and slender being inserted deep into his chute. It was the lube syringe and the cool sensation of the liquid being injected into his spasming colon was momentarily soothing.

Then he felt Tawny move behind him and something blunt and large pressed against his entrance. He knew it was Tawny's cock but it felt like it was the size of a baseball bat! Tawny pushed forward and his sphincter failed him again, letting the head pop inside. The pain was searing. Billy bucked forward again in a vain attempt to escape. "It hurts...it hurts! Please take it out...please...Mistress...Please...!" he begged, but Tawny just applied a series of short gentle thrusts, working more and more of her hard cock up inside him until he was fully impaled on her hard cock.

"Hang in there, Billie. It will get better," she soothed, but he knew it was a lie.

He deserved this. That's what Billy told himself. He had told the same lie to girls he had buggered so he was literally being hoist on his own petard. All he could do was sob "Please" over and over, again and again as Mistress Tawny painfully tore his anal virginity from him. Thankfully she was using slow long strokes to fuck him, making love to her sissy boy as she claimed him. Tawny's gentle lovemaking was drawing it out, extending Billy's ordeal by fire but after a while the pain started to ebb. The pain was still there but it was manageable and there was something else, an intense sensation of stimulation, fullness and...completeness. While Billy wasn't exactly enjoying having Tawny fuck him, he realized he NEEDED Tawny to fuck him. From now on he would be empty whenever she WASN'T fucking him.

That's when she picked up the pace. Tawny started to fuck Billy faster, harder, deeper...her hips painfully spanked his sore butt with each hard thrust. "Fuck me Mistress! Fuck me hard! Claim me...Please..." Billy wailed as he spilled his seed into his pink panties, his pleas also pushing Tawny over the edge.

Tawny gave one final thrust and emptied her load deep into her new sissy boy's bowel, seeding his core. She pulled Billy back to her and hugged her sobbing little sissy closely.

"Your mine now, little Billie," Mistress Tawny whispered in his ear as she hugged him tightly. "It'll be okay. You'll see. I've got you. Tawny's got you...".

Billy knew it would be okay as he relaxed back into her strong, sweet embrace. He belonged to her now. Everything was going to be okay. Billy sighed contentedly as he relaxed back into her.

Mistress Tawny had him...and he knew she would never, EVER let him go.

THE END

Thoughts, suggestions, comments?