The Amazing Mrs. Henderson 1

By PinkFlowed.

Penny and Don Henderson had been married for 24 years, and while they still loved each other deeply, their sex life had become stagnant. Penny longed for more excitement, but Don was content with their routine.

Penny was a sexually confident woman and wasn’t afraid to express her desires. She had always been open with Don about what turned her on, but lately, he seemed less and less interested. Penny had tried everything she could to reignite the spark, but nothing seemed to work.

One evening, they attended a party at a friend’s house. Penny had a few drinks as the night progressed and became more relaxed. She chatted with friends, including a few men flirting with her shamelessly.

Penny noticed Don sitting alone in a corner, nursing his drink. She felt a pang of guilt and decided to go over to him and make sure he was okay. When she reached him, he looked up at her and smiled weakly.

“Hey, babe,” she said, sitting down beside him. “Are you having a good time?”

Don shrugged. “I’m okay. Just feeling a bit out of place, I guess.”

Penny put her arm around him and leaned in close. “You know, you shouldn’t feel that way. You’re my man, and I love you.”

Don looked up at her; momentarily, she could see the desire flickering in his eyes. She leaned in and kissed him, feeling his hands move over her body in a loving embrace.

Suddenly, Penny pulled away and stood up. “Hey, everyone,” she said, raising her voice. “I’ve got a joke for you. What do you call a man with a small penis?”

Everyone looked at her, waiting for the punchline.

“Don!” Penny said, bursting into laughter. “You call him Don!”

Don looked shocked for a moment, but then he laughed too. The group joined in, and soon everyone was in hysterics.

Penny felt a rush of excitement that she hadn’t felt in a long time. She loved being the center of attention and could tell that Don was enjoying it too. She leaned over and whispered in his ear.

“I think we just discovered a new kink, baby. You like it when I humiliate you, don’t you?”

Don showed Penny his shy, boyish smile, and he slowly nodded as he realized himself. Penny felt a wetness between her legs as she thought about what they could do with this new discovery.

Penny and Don left the party and went home. They didn’t waste any time getting into bed, and Penny took charge, using every curse word and dirty phrase she could think of to describe how she wanted to be fucked.

Don was like a different man, responding to her every command and begging for more. Penny was in ecstasy, feeling more alive than she had in years.

Penny soon realized she loved making the “Don jokes” at parties. She loved the attention it brought her and how it made her feel powerful and in control.

She started to make jokes more often, and the reaction was the same each time. People would laugh, and Don would look a little embarrassed but also turned on.

Penny could see that the jokes were having an effect on Don. He seemed to enjoy being the butt of the joke. Penny could feel the power dynamic shifting in their relationship.

One evening, they attended a party at a friend’s house. Penny was feeling particularly bold and had come up with a new joke.

She waited until everyone gathered, had drinks in hand, and cleared her throat.

“What do you call a man who can’t get it up?” she said, grinning mischievously.

There was a moment of silence, and then someone said, “I don’t know. What?”

Penny pointed at Don. “You call him Don!”

The group burst into laughter, and Don blushed bright red. But Penny could see the desire in his eyes and knew he was turned on.

And so, Penny became known as the woman who could make everyone laugh with her Don jokes. She loved the power it gave her and how it made her feel alive. And she loved the way it brought her closer to Don, making their sex life more exciting than ever before.

Penny had always loved making people laugh, and after her success with the Don jokes at parties, she decided to take it to the next level. She signed up for an open mic night at a local comedy club called “Funny Boner’s.”

She spent weeks preparing, reviewing her material, and practicing her delivery. When the night finally arrived, she was nervous but excited.

As she took the stage, she could feel the eyes of the audience on her. She took a deep breath and launched into her routine.

“Hey, everyone! How’s it going tonight? You know what they say, laughter is the best medicine. Unless you’re my husband, Don, Viagra is the best medicine!”

The audience erupted in laughter, and Penny felt a rush of excitement.

“I mean, seriously, my pussy is so hungry, it’s eating Don’s dick like a hungry lion. But, sex with Don is like throwing a hotdog down a hallway.”

The crowd was in hysterics, and Penny felt she was on top of the world. She continued with more jokes, including some new ones she had created.

“Don’s dick is so small. The first time I saw it, I thought it was a zit on his balls.”

The audience roared with laughter, and Penny could see people wiping tears from their eyes.

“Don asked me if I wanted to see his ‘little friend.’ I thought he meant a puppy.”

“Don’s penis is like a shrimp – small, pink, and not very filling.”

“Don’s so small, he could use a Cheerio as a cock ring.”

The crowd ate it up, and Penny knew she was killing it. She could see Don in the audience, looking uncomfortable but aroused.

“As I bid you farewell, remember to embrace your desires, explore your fantasies, and always keep a spare set of batteries!”

When she finished her set, she received a standing ovation from the audience. She could feel the energy in the room, and it was intoxicating.

After Penny’s successful open mic night, the owner of Funny Boner’s approached her with an offer. He wanted her to do a weekly gig at the club, and he promised her a steady paycheck and the chance to perform in front of bigger audiences.

Penny was thrilled. She had been waiting for this opportunity, and she couldn’t wait to get started.

She spent the next week working on new material, pushing the limits of what was considered acceptable for a female comedian. She was determined to shock and awe her audiences, to leave them gasping for air with her explicit language and graphic descriptions.

Before her first weekly gig, she tried out her new jokes on Don and a group of her girlfriends. They all got into the spirit of the humiliation, egging Penny on and demanding proof of her wild sexual exploits.

“You want proof?” Penny said, grinning wickedly. “I’ll give you proof. Don, show them your dick.”

Don hesitated momentarily but then reddened as he complied, pulling down his pants to reveal his slender dick, already hard with the humiliation and pointing straight out, with just a slight upward curve, in its full three-and-a-half-inch glory.

Penny looked at it critically, and then she turned to her girlfriends. “See, I told you. That peewee wee-wee couldn’t satisfy a goldfish.”

The girls howled with laughter, and Don looked embarrassed. But Penny could see the desire in his eyes, and she knew he loved being the object of her ridicule.

“You know what I love about Don? His dick is like a chameleon– it blends in with the rest of his body.”

The girls laughed, and Don looked like he wanted to crawl into a hole and die.

But Penny could see the arousal in his eyes, and she knew he loved every minute of it.

On the night of Penny’s opening gig at Funny Boner’s, Don was nervous. He wasn’t sure if he was ready to see his wife perform such explicit material in front of a live audience.

But Penny was confident and strutted onto the stage with a microphone in hand.

“Hello, all you dirty motherfuckers!” she yelled, and the crowd roared with approval.

She launched into her act, using every foul word and vulgar phrase in her repertoire. She laughed at her body, joking about her stretch marks and saggy tits.

“I used to think 40 was old, but now I’m 50, and I’m like, ’40 was a piece of cake.’ I used to be able to seduce men with just a wink. Now, I need a whole routine… with choreography.”

“I used to have a sugar daddy, but now I have to settle for a Splenda daddy.”

And, of course, she made plenty of jokes at Don’s expense.

“I asked Don to be more adventurous in the bedroom. He suggested we try doggy style…but I think it was only because he wanted to lick his own balls.”

The crowd laughed and hooted, and Don felt himself blushing.

“As I bid you farewell, remember to live life like a gangbang: grab it by the balls and make it scream with pleasure,” Penny finished to a standing ovation.

But then something unexpected happened. As Penny left the stage, a man approached her from the back of the room. He introduced himself as a booking agent and told Penny that he was impressed with her act.

Penny couldn’t believe her luck – this could be her big break. But as she shook the man’s hand, she couldn’t help but notice something strange about him. He was unusually tall and broad, with a muscular build that reminded her of a horse.

As the agent spoke to her, Penny was distracted by his presence. She kept stealing glances at his crotch, wondering just how well-endowed he was. She had always been a size queen in her youth, and the thought of being with a man who was hung like a horse made her wet with excitement.

But Penny knew she had to focus on her career, so she tried to push the thought out. She nodded politely as the agent explained his plans for her – he wanted to book her on a national comedy tour and even get her a spot on a popular late-night talk show.

Penny could hardly contain her excitement. This was it – her big break. But as she walked away from the agent, she couldn’t help but think about the bulge in his pants and wonder if he was like a horse.

After she met with the booking agent, Penny rushed home to tell Don the good news. As soon as she entered the door, she launched into a barrage of jokes centered around the agent’s horse-like appearance.

“Don, you won’t believe it! I met my new booking agent today, and he’s like a horse! I thought you were hung like a hamster, but this guy could probably satisfy a whole stable of mares!”

“They say you should never look a gift horse in the mouth, but when it comes to my agent, I couldn’t help but take a peek!”

“My agent’s package is so big, he needs a special permit just to carry it around.”

“They say good things come in small packages, but in my agent’s case, it’s more like a huge fucking gift!”

To her surprise, Don burst out laughing at her jokes. Penny had always thought Don was sensitive about his shortcomings in bed, but he seemed to take it all in stride.

“That’s hilarious, Penny,” he said, still chuckling. “You really know how to make me laugh. And hey, if this guy can help you make it big, then I say go for it.”

Penny was taken aback by Don’s reaction. She had expected him to be embarrassed or humiliated by her jokes, but he was laughing with her instead.

Penny was touched by Don’s support, and she knew that he meant every word. As she leaned in to kiss him, she felt a surge of affection for her husband.

“Don, you’re the best,” she said, snuggling up against him. “I’m so lucky to have you in my life.”

They started to get a little frisky, and soon they were making out passionately on the couch. Penny was thrilled to feel Don’s dick growing hard in his pants, and she eagerly unzipped him and began to stroke him.

“Fuck, Penny,” Don groaned. “I don’t know what’s gotten into you, but I love it.”

Penny grinned wickedly as she took Don’s dick in her mouth, relishing his taste on her tongue. As she bobbed her head up and down, she couldn’t help but think about her new booking agent and wonder how well-endowed he was.

Penny couldn’t shake the image of her new booking agent’s horse-like appearance from her mind, and she found herself growing more and more curious about the size of his cock.

“Hey, Don,” she said, pulling away from his dick. “Do you ever wonder how big other guys are?”

Don looked at her quizzically. “What do you mean?”

“I mean, do you ever wonder if other guys are bigger than you?”

Don shrugged. “I guess. But why does it matter?”

Penny hesitated for a moment, unsure of how to answer. “I don’t know. I guess I’m just curious. Like, if you found out that a guy you knew had a really big cock, would it bother you?”

Don thought for a moment, then shook his head. “No, I don’t think so. As long as you’re happy with what I’ve got, that’s all that matters.”

Penny smiled, feeling a rush of affection for her husband. “I am happy with what you’ve got, Don. More than happy, actually. But I can’t help being curious sometimes.”

Don chuckled. “Well, I guess curiosity killed the cat. But in this case, I’m happy to indulge your curiosity.”

Penny grinned wickedly. “Good, because I think you might have to do some serious indulging soon.”

* * *

Penny couldn’t wait for her new booking agent to come over for dinner. She had spent all day preparing a delicious meal and was excited to introduce him to her husband.

Penny regaled her guest with her trademark raunchy jokes as they sat down to eat, this time with a particularly suggestive undertone. Don blushed at some of the more graphic punchlines but couldn’t help but be amused by his wife’s irreverent humor.

“What’s the difference between a hot, steamy bowl of soup and a good, hard fuck?” Penny asked.

Her agent thought momentarily and replied, “I don’t know.”

Penny smiled coyly, picked up the ladle, and asked, “Would you like some soup?”

The dinner was a success, and the conversation was lively and dancing with a sexual undertone. Penny finished, “The secret to a great dinner party? A pinch of spice, a dash of naughtiness, and a lot of dessert!”

After dinner, they moved into the living room, where Penny poured each a glass of wine. As they chatted and laughed, Penny became more attracted to her agent.

She had always been drawn to men with a certain raw sexuality, and there was something about his rugged good looks and muscular physique made her pulse race.

As the evening progressed, Penny found herself increasingly bold in her flirtation. She made suggestive jokes and innuendos and even brushed against him a few times.

“They say actions speak louder than words, but sometimes a well-placed whisper can work wonders too,” Penny flirted outrageously with her agent as Don watched the pas de deux play out with fascination.

To her surprise, her agent seemed to be reciprocating her advances. He touched her arm and leaned close to her, whispering in her ear, “You’ve got a killer sense of humor, but I feel your skills extend beyond making me laugh. Care to prove me right?”

Don watched the exchange with a mix of amusement and arousal. Part of him was turned on by his wife’s uninhibited sexuality, but he couldn’t help feeling a twinge of jealousy.

As the night drew to a close, Penny’s agent thanked them for the evening and leaned in to kiss Penny. Don watched in shock as his wife turned the goodnight peck into something completely different, her mouth open, her tongue flicking out to meet him.

For a moment, Don felt his world spin. He had always known his wife was wild, but seeing her kissing another man like this shocked his system.

As Penny and her agent continued to make out, Don felt mixed emotions. Part of him was turned on by seeing his wife giving in to her desires, while another part felt a deep sense of betrayal.

He wondered if he should step in and stop the whole thing, but he found himself frozen in place, unable to move.

Penny’s agent broke away from the kiss, turning to Don with a sly grin. “You don’t mind, do you?” he asked, his voice dripping with seduction.

Don felt his face flush with embarrassment. He wanted to scream out, “Hell, yes, I mind. Get the fuck out of my house!” and yet, a twisted part of him wanted to whisper, “No, I don’t mind. I want to watch you screw my wife because I’m a sick fuck who gets turned on by this shit!” But words caught in his throat, and he said nothing.

Penny stepped in, sensing his discomfort. “Don, baby, it’s okay,” she said, her voice soft and reassuring. “We’re just having a little fun.”

With that, she turned back to her agent, and the two resumed their passionate embrace. Don watched silently, like a voyeur, as his wife made out with another man right before him.

As Penny and her agent’s passionate embrace continued, Don couldn’t help but feel like a third wheel in the room. He felt like he was intruding on an intimate moment between them, even though he was Penny’s husband.

He watched silently, his eyes fixated on the couple as they explored each other’s bodies. He could see the way Penny’s hands roamed across her agent’s muscular frame, pulling him closer to her.

At the same time, he couldn’t help but feel a twinge of jealousy. His wife was a sexual creature, but he could never have imagined that she would be so uninhibited with someone else in front of him. As the intensity of their passion grew, Don felt himself getting more and more aroused.

As he watched Penny and her agent explore each other’s bodies with abandon, he couldn’t help but feel a mixture of excitement and jealousy. He was excited to see his wife in such a passionate state, but he was also jealous that he wasn’t eliciting such a response from her.

As the moments passed, Don became increasingly turned on by the sight of Penny’s body writhing with pleasure under her agent’s touch. He felt a stirring in his loins that he hadn’t felt in a long time.

He watched as Penny’s agent ran his hands over her curves, squeezing her breasts and kissing her neck. Penny moaned softly, her body open and desirous of his touch. He had never seen his wife behave this way, which was thrilling and intimidating.

The agent then moved his hand down Penny’s thighs, slipping his fingers between her legs. She gasped and writhed under his touch, her eyes closing in ecstasy. Don felt himself growing harder as he watched the scene unfold before him.

He knew he should feel jealous or angry at seeing another man intimately touching his wife. Still, instead, he was overcome with lust. He had never been so turned on in his life.

Penny moaned deeply as her agent’s fingers found their way between her legs. She had never felt so aroused before, and his touch as her husband watched drove her wild with desire. She trembled as he worked his fingers expertly, moving her panties to the side, teasing her clit, and sliding inside her easily.

As Penny writhed with pleasure under the agent’s touch, Don watched in fascination. He had never seen his wife so turned on. The agent’s fingers worked their magic on Penny’s body, and Don couldn’t help but be captivated by the sight of his wife lost in ecstasy. He felt shock, jealousy, arousal, and a strange sense of excitement. He had never seen her like this before, so completely and unabashedly consumed by her passion.

Penny’s moans grew louder as the agent continued to stimulate her, and her body began to tremble with pleasure. Don could feel his arousal growing, and he realized he was enjoying this far more than he would ever have anticipated.

Finally, Penny let out a cry of release, and the agent withdrew his hand from between her legs. She collapsed onto the couch, panting and spent, and the agent turned to Don with a grin.

“So, what do you think?” he asked, and Don found himself at a loss for words. He wasn’t sure what he was supposed to think, what he was supposed to say, or what was supposed to happen next. All he knew was that he was excited and intimidated by this newfound sexual energy with his wife and her agent.

Don took a moment to gather his thoughts. He had never expected this kind of situation to arise, but he couldn’t deny the intensity of the experience.

“I don’t know,” he finally said, his voice a little hoarse. “It’s all so new to me.”

The agent chuckled. “I can imagine. But don’t worry, we’ll take things slow. I just want to give you a taste of what’s possible.”

Don realized it was not over and couldn’t help but feel excitement and apprehension as the agent began to undress in front of Penny. He watched as Penny’s eyes grew wide with amazement at the sight of the agent’s enormous cock, which hung heavy between his legs. She had seen her fair share of impressive equipment, but this was special.

“Don, you have got to see this,” she exclaimed.

Don moved from behind the agent, his eyes widening in disbelief. “Wow, that’s… impressive,” he muttered, feeling a twinge of inadequacy.

Penny noticed the look on his face and smiled reassuringly. “Don’t worry, baby. Size isn’t everything. It’s how you use it. But let’s be honest, a little extra size wouldn’t hurt.”” she said, winking at him.

Penny gave Don a little kiss, then turned back to the agent with a mischievous glint in her eye. “Now, let’s see what we can do with this big boy,” she said, stroking the agent’s impressive member.

Don felt his own arousal growing. But for now, he sat back down and watched as Penny took the agent’s cock into her mouth, eagerly sucking and licking him with abandon. Don felt a mix of awe and arousal as he watched her expertly pleasure the agent, taking him deeper and deeper into her mouth.

As the agent moaned with pleasure, Don felt a surge of jealousy tinged with admiration. He wanted to be the one experiencing that kind of pleasure, but at the same time, he was oddly proud of how Penny could take the agent’s massive cock down her throat.

With a mix of fascination and arousal, Don watched as Penny continued to suck and lick the agent’s cock, her hands moving up and down his shaft as she worked him closer and closer to the brink of orgasm.

She stopped abruptly, shimmied out of her panties, raised the hem of her dress, and climbed atop him, straddling the agent’s hips.

As Penny rode the agent with wild abandon, she couldn’t help but make a joke. “Looks like I finally found someone who can give me what I need,” she moaned. “Sorry, Don, but you’re officially out of a job.”

The agent chuckled and grabbed her hips, thrusting deeper inside her. “Don who?” he said, grinning. “I’m all the man you need now.” Penny laughed and gasped as he hit just the right spot. “Oh, fuck yes,” she cried out. “That’s it, right there.”

Don watched in shock and arousal, unsure if he was turned on or deeply hurt by his wife’s comments.

“I don’t always make the right choices, but I make the most entertaining ones,” Penny couldn’t help but continue with the Don jokes as she rode the agent harder and faster. “You know, Don, I always knew something was missing in our sex life,” she said with a sly grin. “I just never knew it was something this big.”

The agent laughed and pulled her down to kiss her deeply, his hands squeezing her ass. “You like that, baby?” he asked, his voice low and husky. “You like feeling my big, fat cock deep inside you, stretching out your married cunt?”

Penny moaned in response, unable to form coherent words as she was lost in the moment. Don looked on with jealousy and desire, his own dick straight as a nail in his pants, as he watched his wife being fucked senseless by another man.


Part 2…

Penny couldn’t believe she had made it to Las Vegas, the world’s entertainment capital! She had worked hard and honed her craft, which had all paid off. She was now performing for a week in the lounge at one of the biggest casinos on the strip. She had also brought Don along with her, partly because she wanted to share a working vacation with him and introduce him as part of her act.

As she stepped onto the stage, she greeted the crowd with a big smile. “Hey, Vegas! Are you ready for some dirty jokes?” The crowd cheered in response. “Great, because that’s all I’ve got.” She launched into her set, telling raunchy jokes and making the audience laugh. But then she switched gears, bringing Don out onto the stage.

“Ladies and gentlemen, I want you to meet my husband, Don,” she said with a mischievous grin. “He’s the inspiration for most of my jokes, and tonight, he’s going to be part of the act.” Don looked nervous, but Penny put her arm around him and whispered, “Don’t worry, baby, it’s going to be fun.”

As Penny continued with her set, she started making jokes about Don, much to the audience’s delight. “You know, my husband loves it when I sleep with other men,” she said with a wink. “In fact, he begs me to do it. He’s such a good little cuck.” The crowd laughed as Don blushed and tried to hide his face.

“I’m not promiscuous. I’m just really friendly! I’ve been around the block so many times, I have a VIP parking spot.”

“I know it’s not easy being married to a woman who’s constantly in demand, but hey, someone’s got to be the center of attention.”

“They say ‘the road to success is paved with hard work,’ but in my case, it’s also paved with many hard dicks!”

“Don always wanted me to be more ambitious, and I’m happy to say that I’m ambitiously fucking my agent!”

“My agent is a true sex magician. With a flick of his wand, he can make my husband disappear… from my thoughts!”

“They say curiosity killed the cat, but with my agent, it’s more like curiosity made me scream with delight!”

Penny continued to make Don jokes throughout the rest of her set, each more outrageous than the last. But Don just continued to squirm in his seat on stage, certain that everyone could see his erection.

“Thank you, ladies and gentlemen! Remember, life is like Don’s dick: it’s short but will screw you if you give it a chance. So, give life a chance and get fucked! Goodnight, Las Vegas!”

And as they walked off stage together, he couldn’t help but feel a sense of pride in his wife’s success, even if it meant being the butt of her jokes.

Penny had never felt more alive than on stage in Las Vegas. Her jokes about Don’s inadequacies and sexual exploits with her agent had become a huge hit with the audience, and she was basking in the attention.

But Penny wasn’t satisfied with just making fun of Don. She really loved to see him red-faced and humiliated. She began to weave more and more risqué jokes into her act, pushing the boundaries of what was acceptable.

She started with subtle hints, alluding to Don’s lack of stamina and endurance. But soon, she was making overt jokes about his small penis and his inability to satisfy her. The audience loved it, and Penny was emboldened to go even further.

“Don’s hung like a matchstick, tiny and only good for lighting things up briefly.”

“I once asked Don if he had a ‘grower or a shower.’ He said he was neither, just a ‘disappointer.'”

She began to tell stories about her sexual encounters with other men, describing in graphic detail what they did to her and how much better they were than Don. She made more jokes about cuckolding him, and the audience laughed.

“I asked Don if he wanted a threesome, and he said, “Sure, who’s the other guy?”

“Don’s favorite position is doggy-style because he can pretend he’s someone else.”

“Don, I don’t mean to brag, but I think I’m becoming quite the expert. I know it’s not fair that I get to have all the fun, but hey, that’s just the way the cookie crumbles.”

“Don thinks of himself as a ‘martyr for love.’ I like to think of him as a cautionary tale for those considering a career in stand-up comedy.”

Don sat in the front row, his face red with embarrassment and arousal. He was still not used to his wife doing this to him in front of all these people. But Penny didn’t care. She was on top of the world and would keep pushing the limits until she couldn’t anymore.

“They say you can’t have your cake and eat it too, but in my case, I can have my cake and eat it with whoever I want. Don, I can’t blame you for wanting to watch me with other men. I mean, I’m a lot of woman, and one man just can’t handle it all… even if you don’t have much to work with.” She winked at him playfully, enjoying how he blushed and looked away. “But don’t worry baby, you’ll always be my number one, even if you don’t quite measure up to my studs.”

The audience roared with laughter as Penny delivered her increasingly explicit Don jokes. They were captivated by her boldness and unapologetic humor. Don sat in the audience, feeling both embarrassed and turned on at the same time. He couldn’t believe his wife was publicly humiliating him like this, but he couldn’t deny the excitement he felt from it.

“I tried to give Don a blow job but couldn’t find anything to suck on.”

“I told Don to go fuck himself, and he said, ‘I would if I could find it!'”

“Don’s sexual technique is so bad, I thought he was trying to perform CPR on me.”

“Don don’t feel bad. I have to rely on other men to do the job too.”

Penny continued to push the envelope with her jokes, and soon the audience was in hysterics. Don squirmed in his seat, feeling like everyone was laughing at him. But at the same time, he couldn’t help but feel a strange sense of pride that his wife was making them all laugh.

Penny’s jokes became more explicit as the show went on, causing the crowd to gasp and hoot with delight. Don felt shame and arousal as he sat in the audience, watching his wife humiliate him publicly. But as she continued, he couldn’t deny the excitement he felt building inside him.

“Don is my rock, my support system. But let’s be honest, my agent is more like my ‘rock-hard’ support system!”

“Don always told me to seize every opportunity that comes my way. Little did he know I’d be seizing my agent, too!”

“They say ‘love knows no boundaries.’ Well, apparently, neither does my agent!”

“Don always wanted me to have a ‘working relationship’ with my agent. Well, he didn’t know how hard we would be working together!”

“Don used to be my number one fan. Now he’s just my number one cuckold!”

“Don always told me that success comes with sacrifices. Well, the sacrifice I had to make was Don’s dignity!”

“Goodnight, folks. Remember, comedy is like a good fuck. It should leave you breathless, satisfied, and desperately wanting more!”

After the show, as they returned to their hotel room, Penny continued teasing and taunting Don with her jokes about his inadequacy. He couldn’t help but feel a twinge of jealousy as he watched her flirt with other men in the casino. Still, he also felt a strange sense of pride that she was his and so desirable that other men couldn’t help but be drawn to her.

As they lay in bed that night, Penny continued to make jokes at Don’s expense, but now there was a new edge to them, a new level of eroticism that sent shivers down his spine. He felt himself getting harder and harder as she whispered in his ear, telling him all the ways she wanted to be fucked by a real man. “Don, you should take notes from my agent. He knows how to keep a woman satisfied.”

And as he watched her climb on top of him, Don couldn’t help but feel excitement and anticipation as Penny straddled him enveloping his rigid rod with her wetness, her eyes filled with mischief. He knew that she was about to take him on a wild ride. Their eyes locked, and at that moment, they shared an unspoken understanding of the thrills that awaited them.

Penny leaned in closer, her lips brushing against his ear as she whispered, “Are you ready for the wildest rollercoaster of your life?” Her voice dripped with a seductive tone that sent shivers down Don’s spine.

He nodded eagerly, his heart pounding with anticipation. “Penny, I’m with you all the way. I’m eager to see where this ride takes us.”

With a devilish smile, Penny began to move her hips, slowly grinding against him. Her movements were tantalizing, a teasing dance that stoked the fire of desire within both of them. As she continued to ride him, Don’s senses were overwhelmed by the exquisite sensations that washed over him. Penny’s body moved with a grace and rhythm that left him breathless. Every movement and undulation sent waves of pleasure coursing through his veins.

He couldn’t help but surrender to the intense pleasure that Penny was bestowing upon him. Her hips swayed in perfect synchronization with his, creating a smoothly oiled machine of desire and ecstasy. Their bodies moved together, a dance of passion and intimacy that knew no bounds.

Penny’s eyes sparkled with mischief as she leaned in closer, her lips grazing his ear. “Do you like how I ride you, Don? Can you handle the heat I bring?” Her voice dripped with a seductive playfulness that only fueled his desire further.

Don could feel himself reaching the edge of pleasure, the tantalizing grip of ecstasy tightening around him. Penny’s movements became more intense, her pace quickening as she guided him toward the brink of release.

With a mischievous smile, Penny whispered, “I hope you’re ready for the grand finale, Don. Hold tight because I will take you on a crazy ride.”

And at that moment, as their bodies moved in perfect harmony, Don surrendered himself completely, surrendering to the sensations that washed over him and the force that was Penny. The world around him faded away, leaving only the intoxicating sensation of Penny’s touch, the rhythm of their lovemaking, and the electrifying connection they shared.

Time seemed to stand still as they reached the pinnacle of pleasure together. Waves of ecstasy crashed over them, engulfing them in a whirlwind of passion and fulfillment. It was a moment of pure bliss, a testament to their deep connection and their profound love.

As their bodies trembled with the intensity of their shared release, Penny collapsed against Don, their breaths mingling in the air. They lay together, basking in the afterglow of their passionate union.

* * *

Penny took the stage the next night and immediately launched into a new set of jokes. This time, they were all about Don’s supposed chastity and how she controlled their sex life. The audience laughed and cheered as she described Don being locked up in a tiny chastity device while she had the key.

“Let me tell you, ladies and gentlemen,” Penny said with a sly grin, “People always ask me how I keep Don under control. I tell them it’s a combination of love and genital imprisonment. I guess I just like to keep my man under lock and key. What can I say? I’m unsure if I’m his wife or his warden, but I’m in charge either way.”

The crowd erupted in laughter as Don shifted in his seat, feeling humiliated and turned on by his wife’s words. He could hardly believe she was talking like this in front of a room full of strangers, but he couldn’t deny the excitement he felt from it either.

“I always say, if you love someone, set them free. And by ‘set them free,’ I mean ‘lock up their penis.'”

“It’s like having a naughty little pet that you have to keep on a leash, except the leash is made of metal and attached to his crotch.”

“I always wanted to be a prison guard when I was younger, and now I get to live out my dream on a smaller scale– much smaller.”

“I call it ‘penis management.’ It’s like time management but with his junk.”

Penny continued with her jokes, describing how she would tease Don mercilessly while he was locked up, driving him wild with desire before finally granting him release. The audience hung on her every word, laughing and cheering as she painted a vivid picture of their intimate life.

“I must say, Don’s dedication to being a cuckold husband is impressive. It takes a special kind of guy to have his heart in his pants and his pride on the floor.”

“Don likes to call himself a ‘chastity warrior.’ I call him my Iron Man, minus the cool suit and superpowers.”

“I’ve come to accept that chastity is Don’s love language. It’s like he’s saying, ‘I love you so much, I’ll let you fuck anyone else!'”

Don couldn’t help but feel like a helpless pawn in Penny’s game, but he was also grateful to be a part of it. He knew he would do anything to please his wife and make her happy, even if it meant enduring public humiliation night after night.

“Before I leave, remember that life is like a gang bang: it’s messy, unpredictable, and you’re bound to get screwed at some point! Goodnight, everybody!”

As Penny’s set ended, the audience gave her a standing ovation. Don stood up with them, his face flushed with embarrassment and arousal.

That night, during Penny’s dinner break, Don wondered about the new direction of Penny’s jokes. “Hey, Penny,” he said, “I noticed you told many new jokes about chastity tonight. What’s up with that?”

Penny grinned mischievously. “Just exploring new territory, Don. And besides, it’s not like your little thing is good for anything anyway,” she teased.

Don felt a pang of embarrassment and hurt. Still, he couldn’t deny that a part of him found Penny’s deep jabs and humiliation arousing. “I guess I just don’t understand the appeal,” he said.

“Well, that’s because you’re not a real man,” Penny replied with a smirk. “Real men understand the thrill of being dominated and controlled by a strong woman like me.”

Don looked at Penny in disbelief. “Are you serious? You want me to wear a chastity cage?”

Penny, with a mischievous grin, gushed, “God, yes! I think it would be so hot. Imagine how much more intense our sex life would be if you couldn’t even touch yourself without my permission.”

Don felt a mix of shock and curiosity as he tried to determine if Penny was serious.

“And it will keep you from wasting so much time jerking off,” she smirked.

“I don’t know, Penny. It seems like a big step. And what if I can’t handle it?”

Penny placed a hand on his shoulder. “We can start slow, baby, and see how it goes. We can always take it off if it’s too much for you. But I have a feeling you’re going to love it.”

Don takes a deep breath and nods. “Okay, let’s try it.”

Penny grins and pulls out her phone. “I’ll order one right now. This is going to be so much fun.”

* * *

As the lights dimmed and the audience settled in for the night’s second show, Penny took the stage with a sly grin. “Welcome back, you dirty perverts,” she quipped, eliciting a round of raucous laughter from the crowd.

She launched into a series of Don jokes that were even more risqué than before, pushing the boundaries of acceptable comedy. The audience ate it up, cheering and hooting at every punchline.

She introduced Don to the new audience and continued, “I heard that in some cultures, it’s considered bad luck to finish too quickly. Maybe you should look into that, Don.”

“Don is so bad in bed. I fake an orgasm during foreplay.”

“I hope you don’t mind that I have to fake it every time we have sex, Don. I just don’t want to hurt your fragile ego.”

Penny didn’t hold back, cracking jokes about Don’s supposed lack of sexual prowess, his small penis, and his inability to please her in bed. Don sat in the back of the club, feeling a mix of humiliation and arousal.

“They say good things come in small packages, but Don’s package is more like a fun-size Tootsie Roll.”

“Don always says he’s a grower, not a shower. I just wish he’d grow a little faster.”

“I told Don I wanted to try something big and exciting in the bedroom. He suggested a new duvet cover.”

As Penny’s set drew close, she made one final joke that brought the house down. “I tried to order Don a new chastity device tonight,” she said with a wicked grin, “but I couldn’t find a cage small enough!”

“As I exit this stage, remember that laughter is like a tube of lube. It makes life’s rough moments a little more enjoyable!”

The audience erupted into applause, and Don could feel the eyes of every person in the room on him. He couldn’t believe he was being publicly humiliated like this, but at the same time, he couldn’t deny the intense rush he felt from it.

When Penny came in later that night, she was buzzing excitedly. “Don, you won’t believe it!” she exclaimed. “My agent just got me booked for a month-long comedy tour! And the best part is, he’s coming with me,” she said, practically bouncing excitedly. “We’re going to be hitting all the big comedy clubs in the country. It’s going to be amazing!”

Don’s heart sank as he realized what this meant. He would be left alone to jerk off for an entire month while Penny gallivanted around the country with her agent. But he couldn’t deny the excitement in her eyes and knew he couldn’t stand in the way of her dreams.

“That’s fantastic, honey,” he said, sounding enthusiastic. “I’m proud of you.”

* * *

As Penny was packing her bags, she noticed a package had arrived for her. She picked it up and brought it in, examining the return address. It was the chastity device she had ordered for Don!

She smiled mischievously, knowing that Don was hesitant to try it out. She opened the package to find a note from the company thanking her for her purchase and including some instructions for using the device.

Penny couldn’t resist the temptation to tease Don a little more. She took a picture of the note and texted it to him with a message: ‘Looks like you’re in for a fun month while I’m on tour. 😉’

As she headed out the door to the airport, Penny couldn’t help but feel excited about the fun she would have on her tour and the thought of Don being locked up and under her control for the entire month while she was gone.


To Be Continued…


*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.

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