Jack simultaneously wanted to cry and rejoice. He didn’t know how much longer he could suffer this way--but maybe, just maybe, some alone time with the cruellest woman would be worth it.
After an exchange of pleasant greetings, Helen McNeal had joined their party. She was wearing the tallest shoes yet: imposing 5” black platform heels that had a menacing point. She stood at 5’10” in them, and looked intimidating in her tailored white suit and pinstripe vest, showing off the shape of her toned, 140-pound body.
“What’s all this?” She said with a laugh as Janet and Erica continued to step on Jack’s body, noticing the sign. Jill excitedly explained the competition to her, and as soon as she was done, Helen’s lips curled into a wicked smirk.
“Let me show you how it’s done, ladies. Step aside.” Janet and Erica looked disappointed, but they stepped off.
Jack desperately wanted to cough and curl up into a ball. He was humiliated, and every single inch of his tormented body ached. The only thing keeping him in place was the desperate, stubborn hope of losing his virginity.
He was only able to get a few breaths of air into his lungs before Helen was on top of him. She stood with one foot on his stomach and the other at his pelvis. The toe of her left foot trapped his cock beneath it, putting continuously more pressure on it while her other foot busied itself by tapping on his stomach. Jack nearly howled in pain, and tears sprang to his eyes. He fought not to let them roll down his face.
“What a great idea to have such a handsome pain-doll available!” She was positively joyful. “It’s too bad he’s not real,” she added sardonically. “I’d love to hear the pathetic noises a real man would make.” The rest of the women bit their lips at this idea, a few unconsciously rubbing their thighs together. They murmured in agreement. Helen continued to slowly, torturously grind Jack’s cock beneath her foot, her eyes flashing darkly. Then Janet got an idea.
“Hey,” she said excitedly, getting the group’s attention. The pressure on Jack’s dick was eased just slightly. “It’s a quiet night in the neighborhood, why don’t we take the doll outside?”
Jill agreed immediately.
“Yeah.” She nodded enthusiastically. “Just to give our guests somewhere to wipe their feet.” She grinned, and a shiver of fear ran down Jack’s spine. “And maybe show off some of these decorations,” she added. “I’d hate for them to go to waste.”
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