Training With Jenny

Jenny turned on him, her thumb over the speed dial of her phone. "Do you know what I want right now, Daniel? I want your cock inside me. Your nice long thick cock, all hard and ready for me, fucking me deep and filling me up. But I can't have that. And you know why I can't have that? Because the last time you were inside a woman you came without permission."

"I'm sorry," he whispered. "I've learned my lesson. I promise--"

"Oh, no, you haven't learned your lesson, not when you're asking me to get you off, as if you have a right to cum tonight." She strode back over to him and leaned down. "You want an orgasm from me? Try this." She grabbed his cock and started jacking him off, rough and tight. Her hand moved so fast he could barely see it. "Come on, jerk your hips, work your cock. You want to get off? Huh?"

He felt his balls pull up tight, felt himself crest the wave, felt the release start to wash over him. "Oh, oh yes--yes!" One hot jet of cum spurted from his dick, and--

--and she let go of him, ruining the orgasm.

"Fuck! Fuck, Jenny, dammit, don't stop!"

Her evil little smile got wider, and she reached for him again. Before he realized what was happening, she was stroking his still-hard penis again, scratching her nails over skin now far too sensitive to bear touch, rubbing her palm all up and down the shaft, stroking her thumb over the head of a cock that felt like it was on fire. His whole body spasmed, trying to get away from the painful touch. "Please--!"

His mistress laughed. "'Please?' How am I supposed to know what you want just from 'please'? First it was 'Oh, Jenny, please let me touch myself,'" she mocked. "Then 'Please touch my dick for me.' Then you want to suck my breasts, and when you finally let me stroke you, you told me you were cumming, and you know that means I have to stop stroking you. Then you begged me not to stop! And when I touched you again, suddenly you're whining that you don't want my hands on your cock. Make up your mind."

He couldn't fucking think, and while he was searching desperately for words, she kept up the torture. He had thought his cock hurt when he'd been teased and denied before, but it was ten times worse having her polish his cock after an orgasm--even a ruined one. He whimpered and bucked, but he was tied to the stool. He couldn't even close his legs to deny her access to his genitals.

"Please, Jenny, it hurts!"

Her voice went low and seductive. "Yes, it does. That's why it's called punishment." She let go of his dick, and he gasped for breath. Jenny picked up her hairbrush, and before he could fill his lungs to scream she brought the hard back of the brush down on his dick. One, two, three. She turned the brush over.

"No! Stop! Please! I'll do anything--"

Gently, smiling, she dragged the bristles of her hairbrush over his hypersensitive cockhead. He screamed.

Then the sharpest of the pains was gone. He hung his head, panting. After a moment her hands soothed slowly over his trembling thighs. In another moment, he felt the vibe in his ass start up again. Jenny got up, and came back in a moment with a glass of cool water. He sucked it down in little choked swallows, and she stroked his hair until he was breathing normally again.

She started to touch him again, this time all over his body: his shoulders, his arms, his chest, down the outside of his hips, around the curve of his ass. The vibrator inside him was working its magic again, and he was hitching back and forth trying to make it press in just the right spot. When her hands ghosted up the inside of his thighs and reached for his cock again, he flinched. But it didn't quite hurt, this time. He was still too sensitive, but he could bear it. Before he knew it, he was getting aroused again. His cock had never quite gone down after the ruined orgasm, but it perked up again now and twitched in front of him.

Jenny licked over the still-sore tip of his cock, and got up. "Time to go, Daniel." He blinked up at her. "Melissa's expecting you home in twenty-seven minutes. You should get going."

She unsnapped the handcuffs and untied his ankles. She bent him over the desk again and pulled the butt plug out. After so many hours, it felt strange and unsettling to have the hardness gone. She threw him his clothes and his wallet and keys.

"Wait," he said, when he had struggled into his t-shirt and pulled his briefs up over his still-hard cock. "Where's my shorts?"

"I gave you back your underwear," Jenny said. "You were so concerned about it before. I'll keep your shorts. I think it's a fair trade." He stared at her, but she only shrugged and pointed at the clock. "Twenty-three minutes. You better get a move on."

So he stood, again, on her doorstep, the sunset blaring into his eyes, wincing at his predicament. With his ass sore and his cock terribly hard in underpants that barely covered his erection he would have to walk across the set--still full of people--to where he'd left his car. And then he'd have to drive home, beg his wife's forgiveness for cumming inside her without permission, and tell her every last thing his mistress had done to him tonight.