Busty Secretary in Trouble

THHHHHHHHHERWWWWWWICKKKKKKK!!

Stephanie screamed, hollering at the top of her lungs as Mr Thompson whipped in number two with a devilishly naughty slice that curled around the width of her wobbling tits at the most tender place of all...the junction between nipple and areola.

"NOT THERE AGAIN SIR!!" she spluttered, reaching around with grasping fingers to trace the searing cut,"...Oh awwwwwwwwww not theeeeeeeeere ..p..perrrr ohhhhh please it HURTS A LOT!!" she squealed as she pushed and pulled each tender mound apart trying to cool off the build up of heat.

Mr Thompson dropped to his right knee in front of her, watching as she kneaded her flesh revealing the rapidly rising blood welts to his close gaze as he sniffed the scent of her pain sweat. That loud thwack and the wail of misery that followed was the most beautiful thing he had ever heard. He had to listen to it again. And again.

He wouldn't have stopped caning Stephanie's soft, vulnerable breasts for anything in the world. The way they jumped and bounced as she thrashed and screamed was magical. They were difficult targets but he did his best to aim for her nipples and they were soon adorned with crisscrossing welts that weeped droplets of blood where the multiple blows overlapped.

Both participants in the display of cruelty and agony lost track of time. Stephanie, alternating between cradling her breasts and rubbing her cunt, tried desperately to focus on the latter rather than the savagery taking place on the former. She was completely unaware of the building heat in her slit, lost in an ocean of pain that poured over her chest. Her boss, the sadistic maestro of this tribute to torment, was oblivious to everything except hurting the gorgeous tits hanging in front of him and the innocent girl desperate to escape.

After what felt like an eternity, his cock demanded attention and he knew it was time to relieve that pressure in Stephanie's helpless fuck hole. Dropping the cane to the floor he fetched the nipple clamps he had hidden in his desk for precisely this occasion.

As he lifted the clamps to their destination at the tips of his secretary's battered tits, covered in welts, drool and tears, his cock bobbed in front of the miserable girl. She knew better than to ignore it and wrapped her soft hands around his member, lovingly stroking it back and forth. While enjoying the cock massage he attached the clamps to her bruised nipples saying, "This is what happens to bad girls who grow their tits so fucking huge. You have to be punished Stephanie."

The squeeze of the clamps was nothing compared to the thrashing she'd endured. Then he began turning the screws. The two metal plates pressed together, flattening the nipple between them and Stephanie again found the energy to scream. She was sure her tender buds would be irreparably crushed but he had far too many tortures in store for her tits to allow them to be permanently damaged. Once both nipples were exploding with pain he let the chain between them drop.

He stepped behind his hapless victim, then bending his knees, he lined up the head of his penis and slowly, steadily pushed inside her tight pussy. He savored every moment of this first penetration and once he was fully buried in her he stayed there, letting her feel his presence in her most intimate place.

Soon the needs of his cock took over and he began thrusting in and out, his strong hands pulling her narrow hips back onto him. The chain connecting her pain filled nipples jumped about. Reaching around her to cup her suffering tits, he ran his fingers over the raised lines left by the impact of the cane. The heat rising from her skin matched the heat in her belly as he pushed into her depths.

Stephanie was lost in despair. She was a sensual girl and enjoyed sex often. There was never any shortage of boys eager to make love to her, make her feel special, wanted, cared for — good. She felt all that fading away, being replaced. The pain in her breasts, the bite of the clamps on her nipples would now forever be associated with sex.

She sobbed and her whole body shook. This expression of her pure misery was the loveliest thing Mr Thompson had seen since he started breaking her. He came, flooding her pussy with his semen for the first as her Master.

Fucking hell. And to think he had nearly sacked her!!