Category: BDSM Stories

Training With Jenny

by ValensGirl©

Back by popular request: the characters from "Negotiations With Jenny" return for a whole story. Daniel learns that his mistress and his wife are serious about certain things.... --VG


Daniel stood on the steps up to Jenny's trailer, shifting from foot to foot nervously. The sun warmed the back of his neck and he was half-hard already, as he usually was when he was about to see Jenny. It made working with her and playing her lover on their TV show a bit awkward, but most of the time she had kept their private sexual affair completely off the set. He wondered why she'd called him over here today. Two o'clock sharp, her text had said. He checked his watch: 1:58. At least he wasn't late.

"Door's open," Jenny called when he knocked. She was sitting at a small table, going over some notes with about five colours of highlighter. The long dark hair she usually wore up for her role curled down her back in thick waves, and she looked ridiculously good in those glasses. Once again he blessed the luck that had made his wife agree to let Jenny be his mistress.

She held up a hand when he started to speak, and finished marking up the page she was on before she turned to look at him. She dragged her eyes up and down his body in a way that made him flush and try to stand up straighter. He wished suddenly that he'd worn something more formal than a t-shirt and cargo shorts. But he could have been in a tuxedo and she'd still have made him feel stark naked by looking at him like that.

"Melissa called me last night," Jenny said.

Daniel swallowed. This whole thing had been his wife's idea in the first place, but it was still embarrassing as hell when he knew she and Jenny had been talking about him. He wondered what they said. Did they compare stories? He always had to tell Melissa exactly what Jenny did to him after their nights together. Did they check to be sure he didn't leave anything out?

"She told me something that concerns me." Jenny was tapping her pen against her notepad now. "She said you came without permission after I sent you home two days ago."

That was the other thing. Melissa controlled his orgasms. She said when and where and how and if, and in the six months he'd been seeing Jenny, he had never been allowed to cum with his mistress. She teased him until he thought he'd explode, spanked him and made him lick her pussy, and even on two memorable occasions had made him suck her husband's cock, but at the end of the night she'd send him home hard, and his wife got to say whether or not he could cum.

He was bright red to the roots of his hair at the thought of his wife telling Jenny what happened once he was home, though. "It wasn't like that," he stammered.

"Oh?" Jenny's smile went suddenly sharp, and he instantly regretted his protest. "I'm nothing if not reasonable. Why don't you tell me what happened?"

He looked at the floor. "I tried. I really did. But you know how you edged me last time?"

He could hear the evil little smile in her voice. "Five times."

"Yeah, and then...and then you told me to touch myself in the car all the way home." His cock twitched in his pants at the memory. He had narrowly avoided running a red light, and had been so rock-hard by the time he pulled into his driveway that it was difficult to walk the last few steps up to his front door.

"And that gave you the right to just shoot your load without asking?"

"No!" His head jerked up to look at her. She was watching him again, staring pointedly at the tent in his pants. "Melissa was in this white, filmy, lacy thing when I got in, and she pulled my pants down and went down on me before I even got my shoes off."

"You came in her mouth?" Jenny's voice rose in disbelief. If he ever came in Jenny's mouth without permission, he had a feeling it would be the last time she'd ever touch him.

He shook his head wildly. Melissa's wet mouth had been exquisite torment on his hot, sore cock, but he had held out. Just barely. "She dragged me into the bedroom and started riding me, and I--"

"You came inside her."

"No. Yes. I--she started talking, Jenny. She said she'd been imagining what we were up to, and she said she'd been touching herself thinking about you. She started to cum while she rode me, talking about your breasts. And I--she hadn't said I wasn't supposed to cum, and I--I forgot."

There was a pause, and he risked glancing at her face. Jenny's eyes were dark and her cheeks were slightly pink. The image of her and Melissa flashed across his mind's eye again, and he sincerely hoped they would never actually make out in front of him. He would probably die from sheer arousal.

"You forgot." Her voice was flat. "After all this time I've spent with you, Daniel. Trying to train you to have a little bit of control over yourself. You just forgot?"

He looked at his shoes again. "I'm sorry," he muttered.

"I can see you can't control your own little cock yet. I still have to do it." She sighed. "Strip and come here. If you're going to get hard while telling me about your transgressions, I want to see it."

He stripped down as fast as possible--when Jenny said "naked" she meant "naked right now"--and went to stand where she gestured, right between her knees. His cock stood out stiffly in front of him, rudely displaying his arousal at just the right height for her to fondle or suck. He put his hands behind his back and arched his hips forward in the way she liked, hoping she would be pleased with him.

She raked her eyes over him again, and skimmed her palms up his outer thighs. She smiled, but it wasn't quite a pleasant smile. She had a plan, and he was probably not going to like it. She ran the fingers of one hand lightly over his penis and even at the gentle touch he had to fight to keep from bucking into her hand. Her smile went wider. "Did you touch yourself this morning?"

He nodded, and had to clear his throat before he could speak. "Yeah. Melissa told me to."

"I hope she didn't let you cum."

It was still embarrassing to tell Jenny what happened with his wife, but after describing how he'd cum without permission, he guessed he didn't have much left to hide. "She made me eat her out, but I had to just jerk myself until she told me to stop." His hands twitched behind his back. He really wanted to be touching himself again right now. "And, um. She gave me a handjob last night and made me go to sleep without cumming."

"Mmmm, good. It really gets me wet thinking of you all hot and bothered like that. I bet you'd hump anything I asked you to, right about now, and I've hardly even touched you." She trailed one fingertip around the head of his cock and cupped his balls with the other hand. As she talked, she began to squeeze, gently and then tighter and tighter. He bit back a moan. "But that's not enough, Daniel. I can't just have you shooting off without thinking first. I think you need some help with your memory, so you don't just forget next time."

She toyed with his erection until he was squirming and trying not to thrust into her hands. She looked up at him from under dark lashes and asked in a low, sultry voice, "How should I punish you, Daniel? For cumming without permission, and getting hard when you told me about it?"

"W-whatever you want, Jenny." He had no idea what she intended, but he knew he would hate it and love it at the same time.

Jenny smiled like the cat who caught the canary. "Yes. Whatever I want." She bent down to rummage in a bag at her feet. "Over the desk, Danny. Spread your legs."

He obeyed, arching his back and displaying himself for her. He felt her hands smooth down his back and over his ass, tracing the curves of muscles and smooth skin. Then she squeezed his ass in her small, strong hands and he jerked against the desk. "Stay still." He felt her knee between his legs, spreading him wider, and something wet and cool dripping down the crack of his ass. Then she was working something inside him, smooth and hard and as thick as two of her fingers. He grunted and tried to keep from wriggling away from her touch. She gave the object a little twist, smacked his ass, and said, "Stand up."

He twisted around awkwardly, feeling the butt plug hard inside him with every movement. He couldn't meet her gaze. He wasn't sure if it was more embarrassing to have something stuck up his ass, or to know that he was still hard even with a plug inside him.

"Look at me," she said, and tilted his chin up. He swallowed but obeyed, feeling flushed and hot all over. She held a small, black, rectangular object in her palm. "See this? This, Daniel, is a remote control." She pressed a button and suddenly the plug in his ass started to vibrate. His hips jerked forward without his conscious thought. She laughed. "Oh, yes. You're going to wear this for the rest of the day, Daniel. I know you can't leave the set because you have to go talk to the director in half an hour. So you're going to wear this, and whenever I want, I'll press this button."

She demonstrated again, and again his hips bucked. She grinned. "I'd love to see you dance around waving your cock for me all afternoon. But you'd better get dressed." She tossed him his shirt and cargo shorts. "Oh, and don't you dare touch yourself. Don't try to hide your hard-on, either. I'm sure you can come up with an explanation if anyone asks."

He pulled on his shirt and looked for his underwear. She hadn't given them back. "I, um, where's my--?"

She dangled his black briefs off one finger, just out of his reach. "Now, Danny, you don't really want these, do you? It would be so uncomfortable trying to put them back on over that big boner you have there."

The vibe in his ass pressed against something sensitive when he bent to pull his shorts on. He zipped them up very carefully over his straining dick. "Um, Jenny, will it stay in?"

She grinned and gave him another zap with the vibe. "You'll just have to make sure it does, won't you?"

He made it to his meeting with the director, but he couldn't concentrate on a word either of them said. He kept shifting uncomfortably in his seat, feeling stretched wide by the plug and trying to find a position where it didn't press against his prostate. Every time he moved his legs, or breathed deeply, or had to lean forward to act like he was following the conversation, his shorts dragged over his cock and made him hyper-aware of how hard he was. For over an hour the torment went on, Daniel tensing every few seconds in dread that the vibe would come on, while with less than half his attention he did the best acting job of his life pretending he wasn't hopelessly aroused. His boss said nothing, but Daniel was absolutely convinced the bulge in his pants was obvious, and he wondered how much of a perv the director thought he was.

Jenny had mercy on him until the last five minutes of his meeting. Just as he was getting ready to stand up and shake his boss's hand and leave, the plug up his ass started to vibrate. He sucked in a breath and tried to keep his face blank, but making small talk while his mistress fucked him remotely with her toy was humiliating and next to impossible.

He escaped at last and almost ran out the door, looking for somewhere private to hide. There was a big tree fifty feet away and he made a dash for it. He leaned up against the wide trunk, gasping, trying to get his breath back. The vibe was still going strong, and every step he'd taken struck sparks up inside him. He wanted nothing more than to rip open his pants and start stroking himself. He shoved his hands behind his back, and concentrated on the rough scrape of tree bark against his palms as he bucked his hips helplessly into the air. He really hoped no one could see him.

The chime of his cell phone made him jump. It was Jenny.

Thought you should know I've cum twice in the last hour thinking about your poor hard cock.

He had a sudden vivid image of her with her head thrown back, moaning in orgasm, her sweet soft breasts rising and falling as she strummed her clit fast and wet. He groaned.

His phone chimed again. Oh, and again just now when I turned on the vibe. ;-) Have you kept it inside you?

The plug felt even bigger when she talked about it, and it was still buzzing. He swallowed hard and scrabbled at the keys. Yes. Jesus...

The reply shot back. Put your hand down the back of your shorts and check. Don't you dare touch your cock. I know you want to.

Keeping his back to the tree so no one could tell what he was doing--though he had to admit that he looked obscene enough with his erection outlined through the front of his shorts the way it was--he shoved his right hand into the back of his pants and probed around for the base of the plug. His awkward fingers felt electric on his butt cheeks; the first touch he'd had since Jenny had put this thing inside him. When he found the plug, he could tell it had slipped out slightly. He told her so.

Push it back in, and hold it there. I'm going to cum again while you hold yourself fucked open for me.

It seemed to take forever for her to cum this time. Her fourth orgasm of the afternoon, he told himself. All the while the plug jittered and buzzed and vibrated inside him, and he could only rock forward and backward in tiny little jerks, pressing the plug harder inside himself and darting his eyes around, panicked, hoping no one was going to walk by.

Finally the vibe clicked off, and a few seconds later his phone chimed again. Ahh, satisfying. You know my blue dildo. :) I love how you're just dying to masturbate right now. Aren't you?

His hands were shaking and he had to backspace every other letter. It hurts, Jenny. Need to touch my dick.

Yeah, no. I want you aching and sore, leaking into your shorts and thinking about the punishment you're going to get tonight.

He slammed his head back against the tree and groaned. Tonight? Fuck, how long was this going to go on?

Go get supper at the canteen. Sit somewhere people can come up and talk to you. Be friendly. Be back here at six.

She turned the vibe on a few more times during dinner while he was being as sociable as he could while trying to hide an erection the size of Florida. Never before had he cursed his popularity on set or the friendliness of the cast and crew. He was waiting at the door of her trailer ten minutes before he had to be there, every nerve on fire and his cock like an iron bar in the front of his shorts.

Jenny opened the door in a towel, hair damp and pinned up loosely. Beads of water rolled down her neck and disappeared into her cleavage. Whatever he had been planning to say died on his tongue. She waved him inside, kissed him on the cheek, and sat down on the edge of her desk to start brushing out her hair.

"Strip," Jenny said. He peeled out of his shorts and shirt in record time. She grinned when she saw his stiff cock, and he flushed as red as his prick. "Sit over there." There was a high stool next to the desk. When he sat down it put him just about on a level with her, and within her reach. The hard seat pressed against the base of the plug in his ass. Jenny brushed her hair thoroughly, watching him squirm, then set down her brush and reached over to tweak his nipples. "Did anybody notice you?"

He mumbled a yes, and she made him tell her exactly who they were and what he thought they'd seen, while she ran her nails up and down his chest and belly. She made him spread his legs wide so she could see his cock and poor blue balls, but she didn't touch them, just dragged her nails up the inside of his thighs. When he told her about standing behind the tree with his hand down the back of his shorts, she buzzed him again with the vibrator. He cried out. "Jenny, please! God, please touch me."

She gave him an innocent look and trailed her fingertips in a circle around his bellybutton. "I am touching you."

"My cock. I need--please touch my cock, Jenny."

The instant he said it he realized he was going to regret it, but God, he needed it so badly. She just smiled at him, though, and said, "All right." She leaned over the side of the desk and dug a pair of handcuffs out of the drawer. "Let's put these on." She cuffed his hands behind his back and took the belt from a dressing gown draped over the desk chair and used it to tie his ankles on either side of the stool so he couldn't close his legs.

Then she dropped the towel.

He couldn't take his eyes off her breasts. Small, soft, round, perfect tits with hard little rosy nipples, skin still damp from the shower and practically glowing. She cupped one breast and flicked the nipple with her thumb and let out a throaty sigh of pleasure. He groaned. She moved closer to him, so that her pussy was pressed right up against his knee, and purred, "So do you still want me to stroke you, or do you want to suck my breasts, Daniel?"

He almost fell off the stool in his eagerness to suckle her. She laughed, and pushed her tit into his mouth, stroking the back of his head. He lost himself in her glorious breasts, licking her soft skin and sucking on her nipples and smelling her sweet, clean skin. He was careful not to use his teeth, but he sucked harder when she groaned and started to rub against his knee. She grabbed the back of his head hard and ground down against his leg, faster and faster until she came, mere inches from where his aching cock still lay neglected against his thigh.

"Ahhhh," she said, settling back against the desk. "I needed that. It's been a whole two hours and sixteen minutes since the last one." She threw her head back and laughed at his expression. "You poor thing. Let me make it up to you."

She took his shaft in her hand and started to seriously stroke him. Her first light touches--on the cock which had been hard pretty much since Melissa had made him jerk himself for her that morning--made him moan. Jenny knew exactly what got him off, and in under a minute he was fucking her hand and bracing for the denial he knew would come. He couldn't stand to tell her he was about to cum, because the instant he did that she would take her hand away. But if he actually shot his load, a second time, without permission...oh, God. "Jenny..." he groaned.

Sure enough, she pulled her hand away, leaving his prick bobbing hard between his legs. He swore quietly under his breath. So close. So fucking close.

After a few seconds she started to touch him again, rubbing her thumb over the shiny head of his cock and then wrapping her hand around him again. This time, when he started to rock his hips, she turned the vibrator on. He was back on the edge in an embarrassingly short period of time, and she kept him there for long minutes, teasing his balls and the underside of his shaft and working the dripping pre-cum into his skin.

He writhed and swore and begged through a third and a fourth round of edging. She got out the lube and slicked him up, fingered herself in a lazy fashion, turned the vibe in his ass on, turned it off, told him matter-of-factly the things she wanted to do with his wife. He whimpered and pleaded until he wasn't even sure he was making full sentences. "Please, Jenny. Let me cum. Please let me cum. Please please please..."

She jerked her hand away from his penis. He gasped and panted hard and looked up at her stern, beautiful face. She tipped his head back and ran her fingers down his neck. "Did you just ask me for an orgasm, Danny? When you know Melissa's the one who owns your cock?"

She walked away from him and rummaged in her bag for her phone. "I think I should call Melissa right now and tell her you're trying to con me into getting you off."

"No!" He jerked forward in his seat and was brought up short by the ties around his legs. "Please don't! I'm sorry. I'm sorry!"

Category: BDSM Stories