Punishment Leads to New Experiences

Kevin was supposed to pick up Molly at 7. They had plans to see a movie and then to get drinks. But Kevin's after work socializing dragged on; drinks with the bros just couldn't be contained, and not being married, he couldn't sell the others on an excuse to leave early. After 7 had passed he sent Molly a quick, succinct text.

"have to cancel, can't get out of work stuff. Srry, but im yours all weekend"

Molly read the text and angrily threw down the phone. A Friday night wasted. She was wearing that orange dress he liked and had just gotten a wax. And she was so fucking horny! Her plan to fuck till dawn was completely ruined!

She eventually composed herself and responded.

"tmrrw at 5, my place. Dont be late. Expect punishment."

Right after sending the text, Molly hit up her Amazon wish list. Next day delivery was a gift from heaven.

Kevin read that text once at the bar, then again when he arrived at home alone and regretted not finding her waiting in his bed. How bad could the punishment be, he thought, as he struggled to sleep.

The next night, Kevin arrived at Molly's apartment just as the sun started setting. She wordlessly buzzed him in, and he made his way up the three flights of stairs. He knew that her anger would be measurable by what she was wearing when she opened the door.

The door opened and he was let in and given a welcoming hug and kiss, although not as passionate as he had hoped for. She was wearing a dark red turtle neck sweater, expansive enough to minimize visible skin, but tight enough to show that she wasn't wearing a bra underneath. That was paired with baggy jeans and sneakers. Her blonde hair was done up in a tight braid.

"Sorry again about last night. For what it's worth, I'm sure I would have had more fun with you."

"Oh, I'm certain of that."

"So what did you end up doing?"

"Well, I did some shopping... and thought of ways to punish you."

As they talked, she led him by the hand down the hallway to her bedroom. He briefly considered that his punishment might be waiting there, and that it may be less of a punishment and more of something fun. As hungry as he was, he was more than willing to change plans to a late dinner, if she had other plans for him.

Entering the bedroom, he saw what was laid out on the bed. Pink lace panties, matching pink lacy bralette, and sheer black nylons. His mind raced to remember whether he had confessed his mild nylon fetish to Molly during any of their past pillow talk sessions. She had never worn nylons around him before, but it was just reaching fall, and they had just started dating that summer; maybe she only wore them in cold weather.

"I like that" he said, gesturing toward the bed. "Is that what you'll be wearing tonight? Or is that what I would have gotten to see you in last night, if I didn't cancel?"

Molly stood facing Kevin, holding both his hands, her smile growing. "Nope. That's what you'll be wearing on our date tonight." He flinched, and his mouth dropped open. Before he could speak, she added, "Remember, you said you're mine all weekend. This is what I want... so get changed."

He stammered, "I... can't... wear... that...out.... I'd be arrested as soon as hit the street. It would show everything..."

Molly cackled and rolled her eyes. "Of course you'll have clothes over this." She motioned to what he was wearing, a basic black sweater and jeans. "Only I will know what you're wearing underneath though... unless I decide to tell someone."

He considered the outfit laid out for him again. His gaze moving from the bed to her and back. Her expression growing more excited by his fear. He started bargaining. "No videos... and no pictures."

She moved her body against his seductively. "No videos. But I'll take pictures if I want, for my own personal use. You've got naughtier pictures of me on your phone... so you're just gonna have to trust me." She bit her lip and stared at him, waiting for his response.

"I've never done this before..."

"Well, maybe this won't be your only new experience tonight..." She reached down and rubbed his crotch through his jeans. The growing bulge told her that he was ready to relent.

"Ok, let's do this. It's just dinner and then back here, right?"

"Yes... probably..."

Kevin sat on the edge of the bed and started removing his shoes and socks. That was followed by his shirt and pants, and then his boxers. Molly stood back, leaning against her dresser, ogling his body. She considered his hairy chest and whether she should also require him to shave it, but didn't want to push her luck.

When he was naked, he picked the panties off the bed and considered them. He felt the material in his fingers; smooth material, but rough texture from the lace. There wasn't much material there to cover his rear, let alone contain his front.

"Go on, get to it. I got those special for you. I'm sure they'll fit."

He stepped into them and pulled them up. As he suspected, his cock flopped right out, rendering them entirely decorative. Molly laughed. "Ooohhh... I like... twirl for me so I can see it all."

Kevin raised his arms and spun teasingly, showing off his ass in the pink lace. He picked up the top and considered it also. He obviously didn't have breasts to support, but it looked like she picked one with a minimal cup size that would snugly fit his chest like a tight crop top. He pulled it over his head and worked his arms through, completing the look.

"Perfect fit, just like I said." Molly was unconsciously moving her hand across her own chest as she watched him. Kevin caught her intentionally tweaking her own nipple, and considered making a move that would distract her from completing the look. But she quickly caught herself and commanded "Be careful putting those on. We don't want any snags."

Kevin picked up the pantyhose from the bed. They were scratchier than he thought they'd be, but also seamless and very sexy. At least, they'd be sexy on Molly, not stretched over his hairy legs. Nevertheless, he sat on the edge of the bed and carefully started working them over his toes and up his legs. He'd seen enough nylon porn to know the proper way to put them on, which kinda surprised Molly. She briefly suspected that maybe he had done this before.

Soon both legs were pulled up, and he stood to raise the rest up to his hips. The tights better supported his genitals than the panties did, and the look of his stiff cock straining under both the pink lace and black nylon was kinda doing it for him. It was doing it for her too. She stepped to him and ran her hands up his nylon-clad thighs, teasing his cock through the nylon.

"Oh my..." she said softly, her gaze not moving from his crotch. "I'm liking this a lot more than I thought. I mean, I knew you'd hate it and it would be a good punishment, but, like, this is really, really doing it for me..." She leaned in and kissed him, moving her hands around to his ass and gripping the nylon covered cheeks as tightly as she could.

"We could skip dinner," Kevin tried, hoping to end the punishment early.

That suggestion broke Molly's trance. "Ha ha... no such luck. We're absolutely going." She stepped back and took her phone out of her back pocket, raised it up and commanded "pose for me, baby. Pose sexy..."

Flustered, Kevin considered how to do that, struggling at first until Molly suggested "How about on the bed, on your side, like that Burt Reynolds poster."

Fortunately Kevin knew exactly which one she meant, and he assumed the pose, not bothering to try to cover his own crotch. Molly gleefully laughed as she snapped pics, then suggested, "One more, standing next to the window, your back to me, then look over your shoulder at me."

Kevin moved to the window and assumed the pose, spreading his legs and tightening his ass for full effect. He heard the phone click a few more times, then Molly say "Oooh, yeah... I like that one... That'll do for now. Finish getting dressed." She smacked him hard on the ass and then left the bedroom and went into the bathroom across the hall. Kevin re-donned his pants, sweater, socks and shoes, and looked at himself in the mirror carefully. No one would be able to tell what he was wearing underneath. As long as he didn't get hit by a car on the walk to the restaurant.

Kevin exited the bedroom and met Molly by the door. She had added a khaki colored army style jacket with large pockets to help protect her from the chill fall air. Kevin tried to give her one more embrace before they left, but she slipped out of his grip and stepped into the hallway. Maybe the punishment wasn't over yet.

They made their way hand in hand to their favorite local restaurant; Henrietta's, just three blocks away. It was the perfect mix of just upscale enough to ensure a mellow crowd and good food, but not so upscale that they wouldn't be comfortable, or would have to worry about their card being declined. They'd been there enough that they even knew some of the wait staff, not on a first name basis, but enough that the staff knew they were cool and steered them away from any suspect new menu items.

When the hostess asked whether they wanted a boot h or table, Molly quickly spoke up "Table, please," knowing that the tables would put them on display in the middle of the room, rather than on the outer edges. She gave Kevin a wink as they were lead to their table.

Their waitress recognized them from past visits and so greeted them with the more friendly, less formal intro. They ordered drinks, and at Kevin's insistence, ordered their food right away. He apparently was in a hurry to end the meal and leave as soon as possible.

Molly teased him when they were alone (aside from the other people just feet away at their own tables). "Why in such a rush? Are you uncomfortable for some reason?" She leaned in closer. "Got your panties in a knot?"

Kevin could feel himself blushing, and while not exactly physically uncomfortable, he couldn't shake the combination of nervousness and heightened sexual desire. He wanted to be alone with Molly, both because there wouldn't be anyone there to see him, and because he really, really wanted to be alone with Molly. If he could have, he'd have taken her there on the table. He considered the bathrooms, but to his memory they weren't conducive to such a discreet rendezvous.

Molly's teasing continued. "You just need to relax, babe. I'm the only one here who knows what a naughty girl you secretly are..." She bit her lip again, knowing how much that turned him on. He felt her foot under the table, moving up his leg, potentially lifting the leg of his pants and exposing the nylons. He moved his leg away from her to prevent that, making her laugh again.

The waitress soon came back with the drinks, and Kevin immediately ordered a second before taking a sip. The waitress gave him an odd look, but Molly quickly waived her in closer. Molly raised her hand to the waitress's ear and whispered something that Kevin couldn't hear. The waitress looked at him and smiled, then stood up. "Oh, I see. That definitely warrants a second drink. And I promise I won't tell anyone." She and Molly exchanged a knowing look, and she left to get the second drink from the bar. Kevin immediately downed half of his drink while Molly beamed.

Molly reached across the table and took Kevin's free hand in hers. After taking another gulp, Kevin quietly said "I can't believe you did that."

Molly rubbed his hands suggestively. "Don't be mad babe. Remember, this is just getting even for you standing me up last night." She leaned in again. "And I promise, you're going to have such a good time tonight, you'll feel silly for ever being upset with me." They were both blushing now, and Molly let go of his hand to take a sip of her own drink. "Tonight is going to be a night we never forget," she added, just loud enough for the couple at the next table to glance over. Now they were both fully blushing, and only the tight nylon prevented Kevin from inadvertently lifting the table off the floor. Kevin's second drink was delivered without any eye contact.

By the time the food arrived, the teasing was replaced with more normal, socially acceptable conversation. They enjoyed their food and drinks, and engaged in some good natured speculation about some of the other people in the restaurant just out of earshot. It was fully dark outside and much cooler when they paid their bill and exited the restaurant.

"You should have worn a jacket," Molly suggested, buttoning up her own.

"I'm actually pretty comfortable," Kevin replied. "Must be the extra layer..."

Molly had Kevin's arm in hers, and she pulled him closer as they walked back toward her apartment. When they passed an alley, she turned and pulled him in. It was dark, and there didn't appear to be anyone there. They passed by an empty dumpster and she turned again, leaning back against the wall. They were now almost entirely invisible to anyone passing on the street.

Kevin was about to lean in and press his body against hers, assuming that was the reason for this detour. But she held up her hands and kept him at a distance. "This is the next part of your punishment babe. And frankly this is the part I'm most worried about."

Kevin looked around. "Worried we'll get caught? I don't think anyone can see us."

"No, worried you won't go through with it... Now be a good girl and get down on your knees."

Kevin was puzzled. Molly opened her coat and unbuttoned and unzipped her pants. When she pulled them down slightly, and pulled down a pair of black silk boxers she usually only wore around the house on rainy days, out flopped a blue plastic cock. Kevin could just barely see it in the dim light. It looked like half of the toy was in her, and the other half was tapered and smooth, not meant to look like an actual cock.

From out of her coat pocket, Molly took a remote control and pressed a button. The fake cock started buzzing, and she let out a groan and parted her legs. "God, I've been wanting to turn that on since we got to the restaurant. You'd better get down there and start sucking or I'm gonna cum without you. And if that happens, you won't like what comes next."

Kevin was incredibly turned on by all of this. He'd never had any inkling toward bisexuality, and never imagined a scenario where he's have to give a blow job behind a dumpster, even if it was a fake cock. He quickly did the mental math and decided that all was good. He leaned in to Molly, feeling her vibrator moving against his thigh, and kissed her, then withdrew and licked her lips the way she liked. Now it was his turn to tease "You want me to suck your dick, babe? Say please..."

"Uhhh," Molly groaned. "Please babe, get on your knees and suck me. It either goes in your mouth now or in another place later."

That threat shocked Kevin into action. He lowered himself and found himself face to face with the vibrator. He took it in one hand and gently worked the other end deeper into Molly, making sure that it was working her clit also. The exterior part was somewhat hinged, so he could lower it aginst her leg (no doubt how she hid it on the way to the restaurant) or raise it up to point to his mouth. His other hand worked around Molly and slid under her boxers to grasp her ass, making sure that one fingertip stayed deliciously close to her other hole.

He reluctantly took the tip into his mouth and looked up at her to find that she was gazing down at him wide-eyed. Her hand grasped the back of his head and pulled him in, the same way he'd done to her many times before. In her other hand, she pressed the button two more times, increasing the vibrations and causing her to moan aloud again.

They quickly found a rhythm, and between the vibrations, the teasing of her ass, and the overall satisfaction of her fantasy coming to fruition, she quickly climaxed. Kevin took the toy from his mouth and raised it up, giving him room to lower his mouth to her thighs and to lick up the dripping wetness.

Soon Molly turned off the vibrator, signaling that it was time to go. Kevin stood and pulled up her pants and boxers, making sure her cock was tucked away. They embraced and kissed, and both considered fucking right there against the wall. Molly was the first to break the kiss. "Just one more task and your punishment is complete," she whispered. She then pulled him by the hand back to her apartment.

Back at the apartment they quickly shed clothes as they made their way to the bedroom. Molly was left in just the black boxers, with the blue vibrator still poking through. Kevin was down to the pink lace and nylon.

Molly pushed him onto the bed, on his back. "Do I need to tie you up?" she asked?

"Maybe," he playfully replied. "Depends on what you have in mind with that." He motioned back to the toy, still half inside her.

The light in the room was dim, with just the street lights outside diffused by the filmy curtains making it possible to see each other. Straddling his hips, Molly massaged Kevin's chest, sneaking a hand under the pink lace to tweak his nipple. She kept up steady pressure on his cock by rubbing her ass against it. Soon, she moved back, straddling just his thigh, allowing her to look down at his cock straining to be released.

"I know about your thing for nylon. You told me about it once when we started dating. I guess I was saving this for a special occasion. Here we are." She leaned over and kissed Kevin's mouth. They were both overcome with passion and lust, and they kissed like new lovers. A string of saliva strung between their lips after the kiss ended, and neither paid it any mind.

"So I kinda have a fetish too," she added, "one I haven't mentioned to you before. I really, really, like to watch." She took Kevin's right hand and lowered it between his legs, slid it into the pantyhose and under the pink panties. He grasped his cock, which was aching to be touched. While she watched him do that, she withdrew the vibrator from her pussy with a loud groan. She set it down on the bed then slid her hand under her boxers. She slid back and forth against his thigh while her fingers worked her sensitive places. She wordlessly nodded, and he started stroking himself.

Her eyes stayed fixed on his cock in its nylon cover, while he watched her face, noted her expression changing, gauged how much longer she had until she exploded. He wanted them to finish together.

She raised a hand to her bare breast, played with her nipple, then wet her fingers in her mouth and worked the other nipple. Her head fell back as she let out another loud moan, then she caught herself and returned her stare to his cock, not wanting to miss out.

Kevin slid the lace to the side and used the texture of the nylon to work his own sensitive places. It worked too well, and soon he was convulsing and nearing his own end. "Oooohh... Molly, can I... It's so close...."

"Yes!" she shouted and ordered, "Fuck yes, I wanna see it... I wanna see you ruin those tights!"

And with that he exploded, with each spurt blasting through the nylon and simultaneously seeping around and soaking the entire area. Without ever moving her gaze, Molly exploded too, soaking the boxers and Kevin's nylon-clad thigh below. They were both panting and giggling when she finally collapsed on his chest.

After catching their breath and more wet kisses, Kevin joked "I'm not sure these panties will wash clean." They both laughed.

Molly snuggled closer and said, "I have one more secret. The waitress..." She felt Kevin tense under her. "I told her it was your birthday and that you didn't want anyone to make a fuss..." Molly laughed again.

"Oh, thank God!" Kevin laughed and pulled her closer. "Is it ok if we change before bed?"

"Yes. Punishment over..." They kissed again and soon were naked under the blankets.