Consulting the Cuckold Humiliation Handbook - Part 5 (Patreon)

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“I know this is hard,” Peyton said as Alan’s fingers hovered over the keyboard. “It’s necessary, though. I think we both agree on that now. You’ve admitted as much several times and I think if you were honest with yourself you’d admit that you’re a little bit excited right now, wouldn’t you?”

Alan looked at his laptop screen and then at Peyton. He nodded, though she could see he was unquestionably feeling a mixture of agony and excitement.

“What do you think the message should say?” Peyton asked.

“I…I think it should say that my wife is looking for someone new to have sex with,” Alan answered.

Peyton reached out and caressed her husband’s leg. She watched his face and witnessed his excitement as her fingers neared his crotch. She was about to implement yet another piece of advice from Cuckold Humiliation Handbook, so of course he was excited, just as he’d been excited every step of the way.

The Handbook Says: Make Your Cuckold Find a Lover for You

“Don’t you think it should start with something else, Alan? Don’t you think the men reading this message should understand why your wife is looking for someone new to fuck?” Peyton asked.

She rubbed Alan’s cock through his jeans as the last words spilled from her lips and he closed his eyes and moaned at what seemed to be an obvious sense of pleasure.

Peyton was determined to get Alan to embrace what she wanted. She wasn’t going to put the words in his mouth. She wanted him to humiliate himself.

Alan typed and Peyton watched the screen to see the beginning of his message to her prospective sexual partners: 

It’s recently come to my attention that I’m incapable of providing my wife with the sexual pleasure she craves and deserves. My lack of size, stamina, and skill in the bedroom has left her deeply unsatisfied and she deserves better. That’s why I’m looking for someone far superior to me to fuck my wife.

“How about that?” Alan asked.

Peyton unzipped his pants and reached inside to free her husband’s unimpressive cock and stroke him softly. “That’s wonderful,” she said as Alan moaned. “How did it feel to type that out?”

“Strange,” he said. “I…I don’t know. It’s this weird mixture of good and bad.”

Peyton leaned closer and offered him a soft, lingering kiss on the cheek. “I know,” she said. “Being a cuckold is going to be difficult for you. You’re going to have to confront your significant shortcomings as a husband while watching someone else make up for them. You’re going to watch another man fuck me. You’re going to watch me break my marital vows and you’re going to watch me do so because you have failed to give me what I deserve. But, you’re going to experience the most intense pleasure of your life while you do so. It’s going to be like riding the most intense rollercoaster you’ve ever been on and I’m going to be there every step of the way to help you, I promise.”

Alan turned to Peyton and they shared a kiss. It started soft and reassuring, like Peyton was using the lip to lip contact to tell her husband that she still loved him. Somewhere along the way Alan surrendered to his desire and the kiss became something more. His lips parted. His tongue moved into her mouth and Peyton welcomed it as she stroked him faster. She wanted arousal coursing through her husband’s body as he finished his message and posted it to the various websites where they’d be searching for a man to fuck her.

“I love you, Alan,” Peyton whispered. “You have shortcomings that make you imperfect as a husband, but there’s a solution to every problem. In this case, bringing another man into our marriage is that solution. I know you’re nervous about it, but I’m not going to leave you. Our marriage is going to change. That’s all. I’m going to have sex with another man and you’re going to watch. You’re going to be my cuckold in every way I desire and as long as you’re good for me I’m going to make sure it’s pleasurable for you.”

Peyton released her grip on Alan’s cock and sat back with a smile on her face.

“Are you going to be a good cuckold for me?” she asked.

Alan nodded, though Peyton could still see the anxiety on his face.

She pointed to the laptop screen and said, “What kind of man should we be looking for?”

“The opposite of me?” he suggested with more than a little pain in his voice.

“Does it hurt to say that, darling? Does it hurt to know that your wife needs someone that is almost the exact opposite of you in bed?” Peyton asked. It wasn’t entirely true – Alan’s deep desire to pleasure Peyton was a good quality – but he came up short in so many different ways where sex was concerned that searching his opposite was a good place to start.

“It does,” Alan admitted. “I know it’s true, but it still hurts a little.”

Peyton leaned closer and ran her fingertip over the underside of Alan’s stiff cock. She teased the tip gently and whispered, “Is that why your cock is so hard, Alan? Is it because you’re in pain, or is it because you’re thoroughly aroused at the idea of another man’s big, beautiful dick plunging into your wife’s pussy and making her scream in pleasure in a way you’ve never done?”

Alan closed his eyes and a shudder of what looked like pleasure moved through his body as Peyton continued to tease him.

“What kind of man do you want?” Alan asked.

“I want someone tall, good-looking, and fit,” Peyton explained. “I want him to have a big cock – at least eight inches – and I want him to be able to last more than a few minutes once he’s inside me. I want a man that likes taking charge in the bedroom, though I don’t need him to be dominant or overly aggressive. I also want a man that has some experience with cuckold couples.”

Peyton wasn’t going to say it, but she wanted someone with experience because she planned on having her eventual lover participate in Alan’s humiliation. She’d deemed it a necessity to help him be the best cuckold possible and she didn’t want to have to train two men.

“Okay,” Alan said as his fingers began to move over the keyboard again:

If you’re interested in showing my wife what it’s like to be with a real man you’ll need to be tall, good-looking, in good shape, and in possession of a big cock (at least eight inches). You’ll need to have at least some experience with cuckold couples and you’ll need to possess both the skill and stamina to give her the kinds of orgasms she’s been missing out on for the entirety of our marriage.

Yes, her standards are high. She’s worth it, though. She’s beautiful, sexy, and in desperate need of a man to show her a kind of pleasure I never have. If you can give her that, I promise she’ll show you a kind of sexual pleasure you’ve rarely experienced. She’s that good.

“What do you think?” Alan asked.

Peyton felt an unexpected sense of joy. It seemed that the lessons she’d tried to teach her husband had taken hold. He seemed to understand that he’d consistently failed to give her what she wanted, and even more importantly he seemed to understand that she genuinely needed to be with someone better.

“It’s perfect,” Peyton said. Once more she wrapped her fingers around Alan’s cock and stroked him. “Are you ready to post your little message? Are you ready to start the search for a man to fuck your wife?”

Alan nodded between moans.

“Go ahead,” Peyton said. “Post it to all the sites we picked.”

She kept her fingers moving up and down Alan’s shaft as he posted on Reddit, Fetlife, SDC, and SwingLifestyle.

“How does it feel to know that you’re a little bit closer to being a cuckold?” Peyton asked when he’d finished.

She knew full well that Alan found it impossible to think clearly while he was getting a handjob. That would have been the case with almost any man. That was the point, though. She didn’t want him thinking clearly. She wanted him thinking about his orgasm. She wanted him thinking about how badly he wanted to cum, not how nervous he was about the idea of someone else fucking his wife.

“I’m so turned on,” he said.

Peyton smiled and leaned closer. “That’s good,” she whispered. “I want you to be turned on. I want your dick to be stiff as you think about someone else fucking your wife. I want you to be out of your mind with desire as you think about someone satisfying me in a way you have always failed to satisfy me.”

A notification from Fetlife popped up and Alan clicked the message. It read:

Do you think your wife would enjoy this?

The sender had included a picture of an exceptionally large-looking cock with his fingers wrapped around the base. Peyton knew she wouldn’t be choosing him – a man that couldn’t be bothered to write more than a sentence was not worth her time – but he had provided her with an opportunity to have a little fun with her husband.

“What do you think, Alan? Do you think I’d enjoy having that big, beautiful cock inside me? Do you think I’d enjoy having that massive cock pounding my tight, wet, married pussy?” she asked in a soft, seductive tone.

Alan nodded as his eyes remained fixed on the picture of the cock.

“Would you want to watch, Alan? Would you want to watch as I cuckolded you with that massive cock? Would you want to watch that cock stretch your wife’s pussy?” she asked.

The desire was obvious in Alan’s voice as he said, “Yes. Peyton…yes.”

Peyton released his cock before Alan could cum and he gripped the edge of the desk as a look of frustration briefly washed over his face. He wanted an orgasm but she wasn’t going to grant him that pleasure until she was ready.

“Check the other sites,” Peyton instructed. “Let’s see if anyone else has messaged you.”

Alan’s Reddit inbox featured quite a few lewd messages and links to pictures, but none of the guys seemed particularly serious. SwingLifestyle hadn’t produced anything in the handful of minutes since he’d made his post. SDC had produced a seemingly viable candidate, though.

“He looks like an intriguing prospect,” Peyton said as she stared at the picture of a good-looking guy in a t-shirt and jeans. He had a smile on his face and a phone in his hand as he stood in front of the bathroom mirror. He’d managed to resist the urge to pull his cock out, too, which she took as a good sign.

“What does he have to say for himself?” Peyton asked.

Alan scrolled down to his message and they both read it:

Though I’m open to all kinds of play, the most satisfying experiences I’ve had on SDC have come with cuckold couples. I love being the man that shows a married woman what great sex actually feels like. I love the look on her face when she has a great orgasm for the first time in years.

I find it equally pleasurable to see a different kind of look on the cuckold’s face in that moment. There’s something so satisfying about seeing him realize that he truly cannot please his wife like I can. That moment changes a man’s life. It changes a marriage. I love participating in that moment. I love being the catalyst for that kind of change in a marriage.

It takes time to know if I’m the right man for your wife, but I’d certainly like the opportunity to be that man. If we click I’m quite certain I can give her what you’ve failed to provide for the duration of your marriage. I can show your wife what it’s like to get fucked by a real man instead of a man that was always destined to be a cuckold.

Let me know if you’re interested.

Scott

Peyton felt a flutter of desire spread from between her legs as she read the message. That was the kind of man she wanted to be with. She wanted someone with the confidence and skill to fuck her like Alan had never fucked her. She wanted to enjoy the kind of orgasm that would change her marriage forever.

It was his apparent understanding of cuckolding that Peyton found most intriguing. She couldn’t help but imagine Alan watching her cum with Scott’s cock inside her. She imagined that look on his face as he witnessed her have an orgasm unlike any he’d ever provided. She imagined that moment where Alan truly understood just how inadequate he was as a lover.

“Are you thinking about it?” Peyton asked her husband. “Are you thinking about that moment?”

Alan turned to her and nodded. He looked intrigued and anxious.

“It won’t be easy,” Peyton said. “Whether it’s Scott or another man that makes that moment happen, it won’t be easy for you. It will be painful. It will make you feel anxious.”

She wrapped her fingers around his stiff cock and stroked him slowly.

“You’ll be hard, though,” she said. “I promise. By the time you watch another man fuck me you’ll be hard as a rock. You’ll feel a kind of arousal you’ve never felt before. You’ll beg me for the chance to masturbate while he’s fucking me. I’ll deny you and you’ll feel enormously frustrated. You’ll wish you could cum while he makes me cum. You’ll wish you could climax while he cums with his big cock buried deep inside your wife’s pussy.”

Alan was caught up in his lust again. Peyton’s slow stroking and dirty talk had led him to a place of wild desire. She knew she could make him cum whenever she wanted.

“I want you to write him back,” Peyton instructed. “Tell him that we’re both interested. Tell him how eager you are for your wife to be with a man that can actually satisfy her. Tell him you’d like to arrange a video chat to take the next step.”

Peyton rubbed her thumb over the underside of Alan’s cock head as he placed his fingers on the keyboard and wrote a reply:

Scott,

Thank you for your message. Though the idea of being cuckolded makes me nervous, I know that my wife deserves to be with someone better. She deserves the kind of sex that I now know I’ve never offered her. She deserves to have the kind of orgasm you described.

For that reason she’d like me to arrange a video chat between the two of you. Please let me know if you’re interested.

Alan

He clicked ‘send’ and Peyton smiled as she leaned in and kissed her husband’s neck while teasing his cock.

“You might have just sealed your fate,” she said. “You might have just ensured you’re going to be a cuckold. You might have just started a chain of events that will end with another man making me cum. How does it feel?”

“It’s incredible,” Alan admitted.

Peyton released her husband’s cock, stood, and pulled his chair back. She stepped in front of him, lifted her skirt, and pulled aside her panties.

“Feel my pussy,” she said.

Alan reached out and ran his fingers over her pussy lips before slipping inside her. Peyton knew she was wet. She could feel it seeping through her panties as she read Scott’s message. Her incredible desire for the kind of pleasure a man like that could offer sealed her intention to cuckold Alan. Any hesitation she’d had washed away. Now she was determined.

“That’s because I want to cuckold you,” she said. “It’s because I want to feel another man inside me. I want to feel another man’s body on top of mine. I want to feel another man fucking me to the kind of orgasm I deserve.”

Peyton stepped closer, straddled her husband in his office chair, and took his cock inside her. Alan groaned as a mixture of surprise and pleasure washed over his face.

“I can barely feel you,” she said. “I could ride you for hours and your cock wouldn’t give me what I needed.”

Peyton grabbed the back of Alan’s chair and rode him while thoughts of another man danced through her head.

“Think of me riding someone else, Alan,” she said. “Because it’s going to happen soon. Today was the first step. Soon I’ll cuckold you. Soon someone else will fuck your wife. Soon someone else will satisfy me like you’ve never been able to satisfy me. Soon someone else will make me cum while you watch.”

“Fuck…Peyton,” Alan said as he grabbed her ass and groaned.

Peyton watched her husband have an orgasm. She watched the intense pleasure wash over his face. She felt his fingers dig into her ass while he unleashed his load inside her. All of it brought a smile to her face. A cuckold-fueled orgasm was a good orgasm, as far as she was concerned.

“Was that good, honey?” she asked when Alan finally looked up at her.

“It was amazing,” he said.

She kissed him softly and whispered, “Savor it. You won’t get to enjoy my pussy very often once I cuckold you. Make sure you remember how good it feels.”

Alan smiled, though Peyton detected a hint of anxiety in his eyes. She wasn’t sure if he was ready to be cuckolded, but it didn’t matter. It was going to happen. It was only a matter of time. She’d make it pleasurable for him, but some of the pain couldn’t be avoided. He’d just have to learn to deal with it.