That is how he ended up with the woman of his dreams wearing just a pair of cheer shorts and a tight pink t-shirt that strained to conceal her perfect giant breasts. He bent down and whispered in her ear, "this is going to be fun," as he started the clock. Slowly opening his bag, he pulled out a thin long feather and though the chest of the tee-shirt was stretched there was enough room to slide the feather up the sleeve of the shirt, and in under a minute she was giggling and moving to stop the tickling. Smiling he stopped the clock, "47 seconds," he said in a voice dripping with smug confidence continuing "I think that shirt is working too hard and has to go"
"As you wish" she commented with a sly grin as she sat up and slowly pulled the t-shirt over her head. slowing as the shirt worked to pull over her breasts, when free of the shirt her chest bounced while revealing a sexy, strategically sheer pink bra, showing almost everything except her nipples. Slowly she returned to her position and as she stretched her legs, she brushed the cold steel of the shackles that awaited her if she failed and a shiver went up her spine, not sure if it was a shiver of fear or anticipation.
He was pleased, choosing such a sexy revealing bra means she wanted to look good if she lost. "Back to the mission at hand," he thought and then pulled out a cooler and removed two ice cubes and closing the cooler. Slowly he traced over the cloth covering her nipples with the cold ice, taking his time making sure her nipples were nice and hard. When they were straining against the fabric, he pulled out two clips from his bag and slowly fastened one to each nipple. He was glad that she did not immediately make a noise or move, but time was wasting after the second clamp was attached, he pressed a button on each and they began to vibrate.
While she succeeded in restraining a moan when the clamps were attached she let out an "OOOOOOooohhhhhh" when they both started to vibrate. She always did have sensitive nipples he thought.
He stopped the clock at 3:52 and removed the clamps, "Two penalties in under 4 minutes" he told her, "Maybe you want to lose, but for now lose...." He continued as she sat up and started to reach behind her back to unfasten the bra, "The shorts."
She was surprised but that is one of the things she liked about him, he surprised her. She stood up and removed the shorts revealing a matching French cut sheer pair of pink panties, and again retorted "As you wish." Shaking her ample bosom before returning to her position.
He started the clock again, and pulled something out of his bag, a thick metal rod with a dull point at the end. He quickly ran it up from the base of her heel to the top of her foot. Reflexively she jumped. He stopped the clock and laughed which pissed her off. "Panties please" he said, extending his hand, "make that 3 penalties in under 4 minutes." He decried as he showed her the 3:58 on the timer.
She made no show of seductively removing the panties, she slid them off and kicked them towards him with her foot. She was pissed, both at him for that dirty trick and because for the first time she realized she might just lose this. Silently she laid back down and settled in. When she was settled, he started the timer and began to rummage through his bag of tricks. She heard two thumps on the nightstand beside the bed, and then heard the click of a lighter, as saw the light from the two candles that were just lit.
"No!" she exclaimed, moving to make sure he couldn't pour wax on her. She immediately knew her mistake.
He stopped the timer and said, "I was just setting some mood lighting, I wasn't going to drip them on you." Beaming ear to ear with a grin knowing victory was imminent. "I would like that bra now, please."
Slowly she unhooked the clasp and let the straps fall off to the side, holding the cups to her breasts and watching as he stared with hunger and anticipation, she had not felt in another's gaze in years. Removing the bra completely she sat there fully exposed giving herself a moment to recompose and hoping to distract him, which she felt was her only chance at winning now. Running her hands up her thighs over her stomach up over her breasts she asked, "Do you like what you see?"