The Chastity Contract Trap

The Chastity Contract Trap

 

A Male Chastity Erotic Novel

Janson Wooding

 

This is a work of fiction. All of the characters, organizations, and events portrayed in this work are either products of the author’s imagination or used fictitiously. Any similarity to real persons, living or dead, is coincidental and not intended by the author.

 

The Chastity Contract Trap

 

Copyright © 2026 Janson Wooding

 

First Edition

 

Cover Design by James, GoOnWrite.com 

 

All rights reserved. No part of this work may be reproduced or transmitted in any form or by any electronic or mechanical means, including photocopying, recording, or by any information storage or retrieval system, without the written permission of the publisher.

 

 

A Wood and Iron Press Book

 

The characters and events portrayed in this work are fictitious. Any similarity to real persons, living or dead, is coincidental and not intended by the author. Contains adult material that might not be suitable for all audiences. This work is a fantasy; in your own life be sure to follow safer sex practices.

 

All characters depicted in this work of fiction are 18 years of age or older.

 

 

Chapter 1

 

Spencer Gordon looked across the conference table at his client. He had just delivered the good news—such as it was—and was surprised by Lorraine's response, but his professionalism didn’t allow him to let that surprise show. 

He remembered what he had said to her as her words still echoed in his ears.

“The prenup is solid. All of your family money is protected. The only real question here is how much of your shared assets you want to go after. Well, that and any financial support for your adult children.”

Lorraine had pushed back a lock of her dyed blonde hair from her face and dead-eyed Spencer when she said, “I’m willing to give up almost all the marriage’s shared assets if he’ll make a concession.”

Spencer was confused. “I don’t understand. You caught him cheating. I’ve seen the evidence. You could sue him for the entirety of your shared assets and probably win. You can split it fifty-fifty if you don’t want to fight. Why make any concessions? I am good at what I do, I can assure you of that, Ms. Stanford.”

He used her maiden name when addressing her. It helped the clients move past the marriage and onto the next phase of their life.

“He wants the money from the marriage to start up a new business. Every dollar I keep from him makes that more difficult. I don’t need the money, but I’m going to make him earn those dollars from me.”

“Okay,” Spencer said easily. “How do you want to do that? I’m happy to have a long, protracted fight. Lots of billing hours for me.”

In response Lorraine reached into her purse. It took Spencer a moment to recognize what she had placed between them. He wasn’t an idiot, but he was confused as to why his client had put a bright silver cock cage made of steel between the two of them.

“Is that what I think it is?” he asked cautiously. He had seen a variety of strange behaviors in his clients when it came to negotiating a divorce agreement. Displays of sex toys and intimate photos and videos weren’t all that strange, unfortunately.

“It’s a cock cage,” Lorraine said easily.

“I can see that…is it some memento or prized possession of his?”

“No. Not at all. I just want him to wear it.”

“Um…I can think of a hundred ways that would be very complicated.”

Lorraine spoke as if she hadn’t heard Spencer’s words. “I found him in our shared bed fucking his whore. I found pictures they exchanged. I found videos they exchanged. I found text messages they exchanged. None of that surprised or upset me. We got married too young. We had kids too young. We were in love.” She paused and corrected herself. “I was in love. He wanted…my family money. Do you know what he wants most right now? Or maybe it’s his whore who wants it.”

“To get married?” Spencer suggested. It was a common enough situation. Husband and wife get divorced and literally the next day one of them is marrying their affair partner.

“I doubt he’s that stupid. No. He wants to get her pregnant.”

“This would be his…affair partner? Vonda is her name, correct?”

“Vonda.” Lorraine made a face. “She’s a decade younger than me. Time isn’t exactly ticking for her, but…”

“You think a divorce agreement where he has to wear…that,” and he pointed to the object in question on the table, “will prevent her from getting pregnant?”

Lorraine nodded her head. “I’m sure he didn’t knock her up before our separation because of the prenup. But that’s now why I want him to wear it.”

After a quick mental review of the document in question, Spencer remembered a clause in the agreement of serious financial penalties for the offending party if an inadvertent pregnancy and child were to occur.

“I doubt I could write an agreement like what you want that would be effective,” said Spencer. “Let alone be approved by a judge. You can’t prevent a person from procreating for the rest of their life. I mean…you could request he get a vasectomy, but that runs into other problems.”

Once more Lorraine shook her head. “Nothing like that. I want him to wear it for three reasons. First, I don’t want him to have sex. Second, I don’t want him knocking her up. Third, I want to punish him. But I only want him to wear it for a year. Twelve months. Isn’t twelve million the amount he could expect to take away from the divorce if we split everything fifty-fifty?”

“Yes,” Spencer agreed. “About twelve million.”

“A million a month. Would you go a month of not having sex to earn an extra million dollars, Mr. Gordon?"

He didn’t want to answer her because he knew the answer right away and it wasn’t to reply in the negative. Instead, Spencer pivoted the conversation.

“Even if he were to agree and even if there was a judge who would approve it there is another real problem.” He poked the chastity cage with a single finger. “This thing doesn’t look exactly foolproof. I’m a man. I can see how it works, but I know how male anatomy works as well. It’s pretty easy to imagine how this would be defeated. Plus, how would you know if he was wearing it or not?”

Lorraine smiled and leaned in. As Spencer had already pointed out, he was a man. It was impossible for him to miss the cleavage she flashed him. He remained professional even as his cock started to harden under the table. He was glad it was wood and not a more trendy glass top. 

“I have a plan for that,” she promised him.

Spencer knew this was a bad idea. But he was intrigued. He wanted to know what she had planned. It wasn’t exactly evil, but it certainly danced close to the line.

“This isn’t going to be easy. Nor will it be cheap.”

“I’m more than willing to pay handsomely to get what I want,” said Lorraine.

Turning his note pad to a fresh page, Spencer started jotting down notes. “What are those ideas, exactly?”

 

Chapter 2

 

Basil didn’t exactly suck in his gut when he fucked his girlfriend, but he didn’t let it hang out either. Vonda was ten years younger and it definitely showed. She was still in the prime of her health, but he had slowly put on weight over the years. The gut he sported wasn’t bad, but it was obvious, especially when Vonda was on all fours as he gave it to her doggystyle. 

He fucked her as hard as he could. He liked seeing a woman’s ass shake with the impact of his body against hers, but Vonda’s ass was trim and muscular. It shook but not the way that really got him going.

She did moan beautifully, however. 

When she was in this position he didn’t have to see her fake tits. She had them since before he met her. Without a doubt she had them done to attract men, though Basil had never directly asked her the question. It wasn’t that he hated fake tits—and Vonda’s were exceptionally well done—it was just the idea. A woman should be all natural, anything artificial done to make her more attractive seemed…wrong.

Even so, he didn’t mind her wearing makeup, he didn’t mind the ornate floral tramp stamp above her ass, or the ring she had in her belly button.

“Give it to me, baby,” Vonda moaned. “Make me cum! Fuck me hard!”

In response Basil grabbed her hips and admired her tattoo for a moment before letting his eyes travel down to her dusky rose asshole. He wanted to spit on it and shove his thumb up her ass to make her squeal as she came. It was all he could do to fuck her as hard as she wanted. 

“Harder!” she demanded

Basil did his best. He summoned up an image of Lorraine licking Vonda’s asshole as he fucked the younger woman. 

That did it. 

Automatically he pulled out of her pussy and shot his load all over Vonda’s back and ass, making sure the last couple of drops landed on her tight little pucker. All the while he was imagining cumming all over his soon-to-be-ex-wife’s face.

Vonda groaned in frustration. It wasn’t that she minded him cumming on her instead of in her—it did make cleanup easier, though—it was that she wanted the hot injection to help her cum. She was right on the edge when he finished and she didn’t want to stop now so she did what any good girlfriend—or nasty fuck buddy—would do. She lifted one hand from the bed and found her sopping wet pussy.

Arching her back and going face down on the mattress, Vonda gave Basil the full view of her ass and pussy, both spread wide, both wet—her pussy from her amrita and her asshole from his cum—as she started masturbating.

This wasn’t a tease. She just wanted to get off. Basil had slumped back and was watching her play with herself. It was a nice show. He wished he had gotten the show before he had cum. He wanted to run his fingers through the cum he had shot onto her back, but he couldn’t make himself do it. 

Vonda wasn’t subtle about what she was doing. She practically sawed at her slit, rubbing her middle and ring fingers over her clit while plunging them deeply into her pussy. It was rough and obscene, the exact sort of sex she liked.

“Fuck…” Basil breathed at the display. Most men would pay handsomely to watch a woman do this and all he had to do was keep her happy.

“Uh! Uh! Uh…yeah!” Vonda’s entire body quivered. Her fingers stayed deep in her pussy while the climax rolled over her body. Every limb, every digit trembled with electric energy as the aftershocks hit.

“You’re such a good fuck,” he complimented her.

Flopping to her side, Vonda gave him half a grin. “Thank you.”

“You’re getting my cum all over the sheets,” he pointed out.

Trying not to groan in annoyance, Vonda moved so that she was face down. “Sorry. It was a good fuck.”

“I need to shower and get to work,” he said.

“Sure.” She lay face down on the bed while he moved off it and into the bathroom. Her fingers were wet with her amrita. Normally she’d be tempted to taste them, not just for her satisfaction but to encourage him as well, but that moment had passed.

The annoyance of his cum cooling on her back and sliding down her sides motivated Vonda to move off the bed and to the bathroom. 

Slipping into the shower with him, she gave her older boyfriend a willing smile. He was in the middle of shampooing his hair. 

“I couldn’t wait to see you again,” she said playfully. 

He gave her a confused look.

In response she turned around, showing him her back. “And I wanted to wash off your cum.”

“Makes sense,” he agreed and stepped aside to let the water wash away his leavings.

After a few seconds, Vonda grabbed some body wash and turned back around while Basil rinsed his hair. She started running the wash-filled puffball all over his chest. 

They looked each other right in the eyes for a moment before Vonda went down on her knees in front of him. He was only an inch taller than she was. He didn’t like her to wear heels when they went out together. It wasn’t that much of a sacrifice. Heels hurt her feet. Flats were more comfortable.

Basil started to object when she took his cock in her hand, but then stopped when she put it in her mouth. She could still taste a bit of his cum and her pussy on him even though he had been in the shower a minute. 

It wasn’t that Vonda hated giving blowjobs. Normally she enjoyed it. Sucking on a man to get him hard gave her that thrilling feeling of being in control of him. 

What she didn’t like about sucking Basil’s dick was the silver CBR he wore.

The first time they had sex he was almost smug when he took off his pants to display the PA piercing he was sporting. She had seen pierced cocks before—Vonda was a woman of the world, after all—but pretended to be impressed and surprised. The taste of metal in her mouth wasn’t fun but it wasn’t annoying either. She would suffer through it.

Giving him a blowjob now was just part of her role of the dutiful girlfriend. Just a little more time and he and his wife would finalize their divorce and she could get pregnant and Basil could start his new business with the money. Then she’d be set for the rest of her life. It wasn’t exactly an original plan, but it was the best she could do. It wasn’t that she was old, but she could see her looks slowly starting to fade. As much as she slathered sunscreen all over her body, freckles and wrinkles appeared regardless. She wouldn’t be young forever. Then she’d be down to her skills…and money. Sex skills and money could keep her looking youthful for a long, long time with the help of a good plastic surgeon.

Basil didn’t exactly get hard. Half-hard at best.

“I just came,” he told her when she looked up at him.

“I like cleaning your cock with my mouth,” she said and got back to her feet. Anything to let him know she was happy to service him, happy to play the role of the submissive.

The moment she stood up his hand went between her legs, feeling her pussy. She was still a bit wet from her amrita but it was being washed away by the water. 

Basil wasn’t really fingering her, he was running his fingers across her mons, feeling the smoothness.

Getting her pubic hair lasered off years ago was the best decision about her body she had ever made. Better than the tattoo. Better than the implants. So convenient to not have to shave every day. It turned on every man she fucked so much.

Every man except Basil.

It wasn’t that he hated it. It was that he pursued her—and Vonda was an easy catch—because she was a natural redhead. He was disappointed that her pussy wasn’t decorated with a little red triangle when he went down on her.

When they started their relationship in earnest and he encouraged her to stop shaving or waxing or whatever it was she did to remove her pubic hair, he was crushed to learn his natural-redhead girlfriend would never grow scarlet curls between her legs ever again. 

He wasn’t disappointed to the point of dumping her, but he had investigated to see if a merkin was something that was practical to correct the problem.

It was not.

“Is this going to be hot and wet for me when I get home?”

Vonda moaned and leaned into him. “Always. I’m always wet for you.” She allowed him to finger her some more. A nice orgasm in the shower would be nice. “When will you be home?” She had to time everything carefully.

“Work this morning and then that fucking meeting with the lawyers this afternoon,” he groused.

She tried not to tighten up but the mention of the divorce proceedings annoyed him to no end. It annoyed her as well.

“Want something special waiting for you when you get home?” Vonda asked, a dozen scenarios whipping up in her head, most of which she was easily capable of doing, the rest of which she was willing to do if it meant she could stay with him.

Then marriage. Then a baby.

Not necessarily in that order.

She moaned softly as his fingering became more strident. She knew she wasn’t going to cum but she at least had to give him that illusion. He sank his teeth into her shoulder and she winced against the pain. Maybe a little more and she could cum. Her hand found his cock and she tried to jerk him off but the water from the shower wasn’t helping. 

“Yeah,” he said, stepping back and withdrawing his fingers from her pussy, wiping them off on her belly. “You naked on my bed with a plug up your ass and clamps on your tits.”

She laughed and kissed him but made a note of the request. Basil finished showering and stepped out. After quickly washing herself Vonda followed him. After he dressed and left for work, she went back to the bedroom, dropped her robe, got her vibrator out from under the bed in the special box that contained all their toys, and gave herself the orgasm she had wanted and deserved.

 

Chapter 3

 

Spencer placed what Wynona thought was a small piece of metal artwork on the table between them. It took her a moment to understand what she was seeing mostly because simply pulling the object out of his case would have been skirting the bounds of sexual harassment…if they weren’t opposing lawyers.

“Is that what I think it is, Spencer? Because if so…it’s completely inappropriate. I’m not one to run to the state bar, but…”

“Ms. Marrit, would I ever do something like that to you?” he asked with an amused smile on his face.

She inhaled and let the breath out in a long, slow exhale. “Not without some nefarious goal in mind.”

“Nothing nefarious at all. What you see before you is Mr. Norwood’s chastity cage.”

“I got that it was a chastity cage, thanks.” It took her a moment. “I’m sorry, are you saying that it belongs to my client?”

“Yes.”

“Is Mrs. Norwood returning it to him?” Wynona asked carefully.

“Not exactly. And she goes by Ms. Stanford now. I’m using it as a prop to open the somewhat uncomfortable discussion we’re about to have.”

Wynona groaned, and not in a good way. “I hate taking these cases for rich clients,” she complained.

“It pays the bills,” said Spencer.

“I know, I know. Is this going to be creepier than the McKinleys?” she asked. “Those two freaks arguing over who got which piece of…um…”

“The term we settled on was bespoke erotic art,” he reminded her.

“Right. Arguing over which piece of porn each one of them got to keep.”

“Maybe creepier,” said Spencer.

“I need to increase my hourly rate,” she muttered to herself. “All right, lay it out for me.”

Spencer tried to stifle a smile and completely failed at it.

Wynona sighed. “Are you really going to be a middle school boy right now?”

“Sorry. Phrasing.” He cleared his throat. “Okay. I’m not sure how much Mr. Norwood has told you, but at some point while Mr. Norwood and Ms. Stanford were married he had a Prince Albert piercing done.”

“I’m afraid I’m going to need to know exactly what that means.” Wynona wasn’t eager to find out, but apparently it was her job now.

“It’s a body piercing of the male genitalia.”

“I should have guessed that…”

“Do you mind if I get a bit graphic now?”

“Yes I mind, but go ahead.”

“It’s the type of piercing that is done through the underside of the penis and out through the male urethral opening. The most common piece of jewelry associated with it is commonly known as a CBR, a captive bead ring.”

“Got it. Thank you. Why do I need to know this? And I know I’m going to regret asking a second question, but why is it called a Prince Albert piercing?”

“Second question first. It’s called a Prince Albert, or a PA as the kids say, because supposedly Queen Victoria’s husband, Prince Albert, had one. Rumor has it that he had a huge…well, you know, and he needed the ring through it to keep his…um…manhood under control. They wore tight pants in his time.”

“How do you know this?”

“I’ve done a lot of research. Believe me, it was not all fun. And three years of law school barely gave me enough critical reasoning skills to separate the facts from the bullshit found online. Want to know more?”

Wynona wanted to hide her face in her hands, but remained professional. “No. I knew I was going to regret the question.”

“Answering your first question, you need to know this because in addition to having a bit of intimate jewelry, during their time Mr. and Mrs. Norwood played chastity games. For him.” He gestured at the tiny phallus shaped metal art sculpture between them.

“Great info. Am I to return this to Mr. Norwood as an act of goodwill on the part of his soon-to-be ex-wife?”

“Not exactly.”

“This keeps getting worse and worse.”

“Ms. Stanford has a complex proposal for your client.”

“I’m guessing it has something to do with that.” She pointed to the chastity cage.

“You’ll notice that it has a unique hook at the end,” said Spencer, carefully rotating the cage for her viewing.

“How do you touch that thing with your bare hands?” Wynona asked him.

“It’s been washed. Sterilized. Besides, statistically speaking, more than half of the people you shake hands with have had a cock in them at some point in the past twenty-four hours.”

She gave him a look of annoyance. “State bar complaint looming,” Wynona warned.

Spencer cleared his throat. “I do know a bit of your personal history as well, Ms. Marrit.”

His reminder caused her to blush, but only slightly.

“Okay, what’s the proposal that Ms. Stanford is suggesting?”

From his case Spencer pulled a piece of a paper and slid it across the conference table. “I assure you it was nowhere near anyone’s genitalia. It’s safe to handle.”

“Thanks,” she said sourly and started reading.

After a minute of reading she looked up. “There’s no way he’s going to agree to this. There’s no way a judge would approve it.”

“Ms. Stanford assures me he’ll agree. And we don’t necessarily have to take it to a judge. It will be a private agreement between parties.” He smiled. “And we can charge exorbitant fees to maintain and monitor the agreement.”

“I can’t see any man, especially Mr. Norwood—and I know my client well—agreeing to the following.” She read from the document. “‘Mr. Norwood agrees to wear the chosen chastity cage and refrain from penetrative vaginal sex with any female partner for the length of the agreement, one year from signing.’”

She sighed and added, “I have so many questions.”

“I have so many answers,” he told her.

“He gets basically a million dollars a month to wear the thing,” Wynona mused. She looked up at the lawyer across the table, a man she had worked with on many divorces, a man she had known since law school. 

A man she had known intimately.

“Would you wear one for a million bucks a month?” she asked him.

Spencer chuckled ruefully. “I haven’t gotten laid in…I don’t know how long. Six months? Longer? Sure. Pay me for the privilege of not having sex.”

“When was the last time you…um…?” She paused and found some courage. “Enjoyed in some self-love?”

“That’s a different question, isn’t it?”

“It sure is,” she agreed and went back to reading. She wasn’t hating the proposal. It gave her ideas.

 

Chapter 4

 

“Hold still,” Lorraine muttered. The straps of the harness were cutting into her skin, but she barely felt them. The slippery purple phallus projecting out from her crotch wasn’t behaving.

While she struggled, Ethan reflected that sex with Lorraine was always wild. When she asked him if he wanted to try anal, he had quickly agreed. He didn’t think it would entail him getting fucked in the ass.

But he didn’t say no.

Maybe he was a bit too curious about it. Maybe he had a thing for older women. Maybe he couldn’t say no to a strong, dominant, and beautiful woman.

Who was going to know anyway?

“There we are,” Lorraine sighed as she saw the purple dildo slide into Ethan’s dark brown puckered muscle. Watching it was beautiful.

Ethan moaned. He didn’t know what was happening. He sucked in his breath. His ass tried to clamp down on the object inside him, but it was too slippery, too hard, too big. He felt violated.

He felt wonderful.

“Hold still,” Lorraine cautioned him as she adjusted her position. He was on all fours and he felt vulnerable. He didn’t know how she had managed to talk him into this (yes he did—she was strong and in control and she assured him he would love it). 

Experimentally Lorraine slowly moved her hips forward, going deeper into Ethan.

“Oh…fuck…” 

“Do you like that?” she asked him.

He wanted to say no. Somehow getting fucked in the ass by a woman seemed to be the least masculine thing he could possibly do. But if that was the case, why was his cock rock hard? He wanted to lift a hand and jerk off while she was up his ass. 

“Holy fuck yes,” he blurted out.

Lorraine chuckled. “I knew you would. My husband loved getting pegged.”

Ethan was glad he was facing away from her because he winced right then, not because the dildo she had up his ass was hurting—quite the opposite, in fact—but because he didn’t like being reminded that she was married. It seemed wrong, like he was breaking a rule, but this had all been her idea from the start.

“Are you ready?” she asked after he didn’t respond to her comment.

“Ready for what?” He couldn’t think clearly.

“For me to fuck your ass. Wait until I start hitting your prostate.”

“Wait. What?”

Lorraine didn’t wait and she didn’t answer his question. She just held onto his hips and started thrusting, slowly at first, but then with increased speed. He was uncertain if he was actually going to like it. Having something up his ass was a completely new experience and it felt wrong, but then she started doing her thing and then it felt incredible.

He wasn’t sure what she meant about hitting his prostate…until she did exactly that. He went from starting to enjoy the experience to being right on the edge of orgasm in the blink of an eye.

“Oh fuck, oh fuck, oh fuck,” he repeated over and over. Ethan desperately wanted to jerk off, but he didn’t dare upset his balance now. Never before had he come so close to cumming without touching his cock. Everything about sex shifted for him right then.

“You okay?” Lorraine asked him.

“Uh-huh.”

“You want me to keep going?”

He realized that she had stopped moving. She hadn’t pulled out of his ass, but had backed up a bit.

It killed him to say the words.

“Yeah…but go slowly.”

“I’m not hurting you, am I?”

“No…”

Once again Lorraine started her thrusting. She partially attributed her flat abs to the many, many times she had pegged Basil. It wasn’t the only thing, of course, and she had to spend more time in the gym now to keep her belly under control, but it was worth it when she got to fuck pretty young things like Ethan.

Her enjoyment of pegging was somewhere between academic and controlling. There was a mild sexual buzz to it, but she knew she wasn’t going to get off from pegging Ethan’s ass. His enjoyment of the act, however, was completely different.

She leaned forward and continued to thrust with just her hips while curling a hand around his body to find his hard cock.

“Oh, you are hard!” she exclaimed. She wasn’t truly surprised, but it was nice to find him in that state.

“Yeah…” he grunted.

“Sometimes men go soft when they get fucked in the ass.”

“Uh-huh.” Ethan wasn’t able to fully focus on her words.

“It’s really strange when they cum and they’re soft,” she whispered in his ear. “Do you want to cum?” Lorraine started pumping her hand up and down on his erection.

He knew he wasn’t going to be able to hold out much longer.

“Yeah…”

“Are you going to be able to make me cum?”

She kept thrusting, kept working his cock. He tried to parse the words, but they weren’t making sense in his head.

“How?” he finally asked.

“You’re going to eat my pussy and maybe we’ll get out some more toys.”

He nodded. Her hard purple cock was going deeply again. He loved this. It was a lot of effort, but he loved it. He knew he was going to ask her to do it again. He knew he was going to run his mouth and ruin this relationship, but it was worth it. 

She let go of his cock and ran her hand down to his balls. “So full, so heavy,” she complimented him. “I want you to cum. Will you cum for me?”

Ethan nodded. She released his balls and started jerking him off again, thrusting as fast as she could.

He came a second later, his spunk making a mess on her bed, making a mess of her hand. He was gasping and straining. He hadn’t felt like this in a long time.

Forced to lock his arms so he wouldn’t collapse, Ethan focused on breathing through the aftershocks. Then Lorraine pulled out of him. That was weird, but it didn’t hurt. It was just…strange.

Now separated, he collapsed to his side as she loosened the harness’s straps and pulled off her sopping wet cotton panties. A moment later she was back on the bed, positioning herself over him, lowering her pussy to his face.

“Eat me,” she told him. “Make me cum.”

Ethan didn’t need to be told twice. He was coming down from his sex lust but that didn’t mean he wasn’t willing to show off his cunnilingus skills.

It only took him a few minutes to coax an orgasm out of her, then she cuddled up next to him, unconcerned with the sweat and cum that covered both of them.

“This is nice,” she said after giving him a kiss. “We’ll do it again. You take getting pegged much better than my husband. He always saw it as some sort of punishment. He loved it, of course, but he felt it made him less of a man. Silly, right?”

“Yeah,” Ethan immediately agreed even though he had had the exact same thoughts earlier. “Silly.”

“I’ll give your ass a rest. We won’t do it today.”

“Thanks.”

“How about tomorrow?” she asked, half-serious and half-teasing.

“Uh…I have plans,” he answered, dodging the question.

“Oh? Doing what?” Lorraine asked the question innocently, but there was nothing innocent about Lorraine.

“I have a…uh…date.”

“With who?”

“Just…someone I’m sort of seeing,” he confessed.

“You are? Is she a girl?”

“What?! Yes, of course she is!”

“Good, good. Just checking. Can I meet her?”

“Are you crazy? No!”

Lorraine frowned. “That’s too bad. If I like her, I’d love to have a threesome with the two of you.”

It was so easy for Lorraine to leave Ethan speechless.

 

 

Chapter 5

 

“Fuck no,” said Basil as he pushed back from the conference table. Wynona was a good lawyer and if he wasn’t paying her for legal advice he not only would have talked her into his bed, he would have fucked her so hard that she would beg him for more.

“It’s not worth a million a month to you?” asked the other lawyer in the room, the lawyer Basil hadn’t been introduced to.

Basil looked back to Wynona. “A million?”

“You didn’t allow me to get that far.” She extended the written agreement across the table to him. “It’s a generous offer…except for the restriction she wants to impose.”

“It’s a sick and perverted suggestion,” Basil raged, not bothering to look at the agreement. “She just wants to control who I have sex with. Hell, it’s not even that. She just doesn’t want me to have a kid with Vonda. She doesn’t want me having sex with Vonda. To even suggest that I’d put something like that on my cock is borderline criminal.” He paused for a second. “Is it criminal?” he asked Wynona, looking for an angle against Lorraine.

“No. But it is…perhaps unethical, that’s why, except for that one piece of paper, we’re doing this as a verbal agreement at first.”

Basil sniffed and glanced at the paper, but didn’t read it. “Doesn’t matter. Even if I wanted to do it, there’s no way she could know if I was wearing a chastity cage all the time. Plus, I know a little bit about this sort of thing. Those toys don’t work.”

The two lawyers glanced at each other. 

“Do you want to lay it out for him, Spencer?” 

“I doubt he wants to hear this from his wife’s lawyer,” he replied.

Basil’s eyes narrowed on Spencer. “You’re Lorraine’s shyster?”

Spencer gritted his teeth and remained calm. “I’m her lawyer, yes. Wynona and I thought we’d make the suggestion to you together and see how it went, both of us answering questions.”

“Why isn’t she here?”

“You two don’t have the best relationship right now,” Spencer answered.

Basil nodded. “True enough. Anyway, even if I agreed to it, it would be so easy to defeat that thing. It’ll never work.”

The two lawyers looked at each other again. Wynona gestured to him, letting a man take the lead on the details of complete chastity. 

“We know—according to your wife, at least—that you have a PA piercing,” he began.

Basil interrupted right away. “So? And I can take that out any time I want!”

“We’ve looked into it and with a PA piercing, completely secure chastity is possible.”

“No it’s not,” Basil contradicted him.

“It is, barring removal of the lock itself but that would be supplemented by breakaway security tags. We’ve done a lot of research on this. If you want a million a month on top of the amounts specified in your prenup, you’ll have to wear a chastity cage of Ms. Stanford’s choice, with your approval, and subject yourself to regular inspections by a third party, also agreed upon by both of you.”

This time Basil didn’t say anything.

“We can give you time to think about it,” said Wynona. “It’s a lot to process.”

“She wants to stop me from having another kid, doesn’t she?”

“The agreement is only for a year,” said Spencer, half dodging Basil’s question. “What you do after that is entirely up to you. There will be no more money afterwards, of course. Your two children with Ms. Stanford are adults and—”

“Was this your idea or hers?” Basil demanded of him.

Spencer’s eyebrows went up. “Hers, I assure you.”

“You ever see a man with a pierced cock?” he asked the both of them.

Once more the lawyers exchanged a glance. Spencer just shook his head. Wynona said no.

“Want to?” He gave her a lop-sided grin.

“That’s not necessary, Mr. Norwood.”

He stood up and rested one hand on his belt. “You might be seeing a lot of it if I agree to this scheme.”

“It’ll be a third party,” she reminded him

“Sure, sure.” He picked up the simple contract. He noted there were no names on it. Basil wasn’t stupid. He knew that was so no one could be blamed if it became public. Not that the general public would care, but this sort of thing certainly wasn’t a common agreement and the legal system wasn’t about to endorse it. “What else did she tell you about me?”

Spencer spoke up first. “Other than the piercing? Nothing. There’s nothing else I need to know.”

“Very little,” Wynona agreed.

“A man who pierces his cock is strong and brave, wouldn’t you agree?” He didn’t direct the question at either one of them.

“I don’t have an opinion on that,” Wynona offered.

“Sure,” Spencer conceded, interested in where Basil was going with this.

“She and I played with chastity in the past. During better times. Ever get a lap dance from a stripper? Dancers are there just to get men hot and bothered and hard and eager to go fuck their wives and girlfriends. Wearing a chastity cage is sort of the same. Put it on in the morning and wear it all day and get all sorts of eager. Makes the sex better that night.”

“Right,” Spencer agreed, sorry he had said anything.

“This is going to be a year-long tease,” Basil mused. “She’s going to want me to fuck her so hard after I get that last million from her…Fuck it. I’ll do it. Where do I sign?”

 

No immediate agreement was signed. Details had to be worked out. A proxy agreement would be put into place that would serve as the legal cover for the yearlong caging of Basil’s cock. Basil left the office feeling good about himself. He had resolved to go home and fuck Vonda until she was screaming so loudly the neighbors called the cops.

The closest neighbors lived two hundred yards away through a wooded lot.

“What do you think of all this?” asked Wynona as she and Spencer put the finishing touches on the contract.

“I think he’s definitely cheated on his wife in the past with someone other than his current girlfriend.”

“Without doubt. But on a different note, I think that he asked Lorraine to put the chastity cage on him in the first place.”

Spencer was taken aback. “You do?”

“He’s got small man energy. Has to prove himself. He wants to show off his cock. He wants people to know he has a piercing. He wants people to know that he’s been in a chastity cage before, but his wife or partner or girlfriend or whatever can’t leave it on him because they want his cock so badly. That’s what he thinks.”

“You think he believes he’ll wear it a few days, maybe a week, and Lorraine will be begging him to take it off so he can fuck her,” Spencer summarized.

“Yes. Maybe not that quickly, maybe not so reductively, but yes.”

Spencer shrugged. “Whatever. Not my life. As long as they keep paying the bills, I don’t care.”

“Have you considered it?” Wynona asked while reading through a few more lines of the contract and making a small note.

“Considered what?”

“Wearing a chastity cage.”

He laughed. “Definitely not. If I could get laid today, I wouldn’t be doing anything to prevent that.”

“What happened to your last girlfriend? Hadn’t you been dating her for over a year?”

“No. She ended it right before we had been together a year. It just didn’t work out. I could ask the same of you. Weren’t you seeing that guy Bill from Albertson, Emerich?”

“Was seeing,” she said. “No longer. It didn’t work out.”

“Maybe working in family and divorce law was a bad decision for the both of us.”

 

“That’s right,” Basil murmured. “Take it all the way down your throat.”

He had found Vonda in his house. Their shared house. He knew she looked to him as a means of support. She didn’t work. She needed a man to take care of her and give her money. It was a good thing she was beautiful and loved to fuck and be fucked. It didn’t matter if she worked or not. Once the year was up she’d be begging for his cock, just like Lorraine. Maybe he’d fuck the two of them together. That would be epic.

Vonda looked up at him with wide eyes. She easily took his cock down her throat. He wasn’t massively endowed. She had learned to deepthroat years ago. It was a little strange to feel his CBR in the back of her mouth but she could handle it. She could handle anything.

“You like sucking my cock, don’t you?” Basil asked.

“Uh-huh,” she moaned around his hardness. 

“I’m going to cum on your face,” he decided. “And you’re going to leave it on until I get back home tonight. You’ll look pretty with my dried cum on your face.”

She half-smiled at him around his cock. More than once he had fucked her before they went out on a date and he had insisted she not clean up so that his cum was leaking out of her pussy the entire time. 

Vonda kept telling herself it was worth it.

“Can I swallow some?” she asked, taking his cock from her mouth and then licking the underside before pumping it with her hand. He was already throbbing, ready to cum.

Basil’s eyes had closed. “Yeah. Some. Not all.”

“Hot,” she pronounced and pumped her fist faster.

Basil let his head flop backwards but then he brushed aside her hand and started jerking himself off. It only took a few seconds. His eyes snapped open and he looked down at her. Vonda opened up her mouth, ready to take as much of his cum in her mouth as possible. 

He aimed for her forehead. When the first spurt shot out, Vonda closed her eyes. The first bit hit her forehead. She felt some land in her hair. The second shot landed on her nose and cheek. She dared to open her eyes and managed to get the last bits in her mouth.

The real trick was swallowing the cum while making the appropriate sounds of satisfaction. Basil’s cum tasted fine, no worse than any man’s. When he was done cumming she sucked on the head of his cock, but he pulled back a bit and traced the softening flesh through the cum that was sliding down her skin.

Backing off a bit, Basil used his fingers to work his cum into her skin, feeling it dry as he played with it. The bit clinging to her hair was the best. He liked marking his territory this way. Cumming on her. Cumming on any woman. Cumming in any woman. She hadn’t let him piss on her, not yet. But it was going to happen. He vowed that. 

“I’ve got to get back to the office, babe,” he told her. “But when I get back, I’m going to fuck you so hard you’re not going to walk straight for a week. Keep that cum on your face.”

With that he tucked his cock away and zipped up his pants. He didn’t kiss her goodbye. A minute later he was back out the door and in his car, driving away.

Basil had caught her wearing her yoga clothing, a tank top and tight fitting pants. She had been slightly sweaty from doing yoga when he walked in the door. That was fine. He didn’t need to fuck her. A blowjob was all that he had needed. She hadn’t removed a single stitch of clothing. It was hotter that way.

Going to the walk-in closet Vonda opened the door to find Grant still hiding there, trembling slightly.

“He’s gone,” she reported. “Sorry about that.” She stepped back so he could exit. He was wearing only a pair of boxer briefs. He had been too frightened to put on the clothes she had tossed in after him when Basil arrived home unexpectedly.

“You said he never comes home in the middle of the day!”

“So I was wrong. Big deal. We didn’t get caught.”

“We could have!”

“That made it more fun, didn’t it?”

They had been making out and she had just started a blowjob when she had heard the front door open. It was easy enough to switch from blowing Grant to blowing Basil. 

While she wasn’t going to tell either man, it had been fun for her to switch like that. The risk of getting caught was a thrill she hadn’t expected. She wanted to do it again.

“You have cum in your hair,” Grant pointed out as he grabbed his clothes from the closet and started dressing.

“Want to add to it?” she teased him but paused when she saw him dressing. “What are you doing?”

“Getting the hell out of here.”

“I want to suck your cock first.”

He paused. She was beautiful. She was dangerous.

“This is too crazy.”

“What’s the worst that could have happened?” she asked him as she fell to her knees in front of Grant and pushed his pants back down from where he had been trying to zip them up. “He would have screamed and yelled and kicked you out. You would have left. No biggie.”

“What would he have done to you?” he asked, concerned.

“Nothing,” she answered breezily, taking his still soft cock in her mouth. He wasn’t huge, but he was bigger than Basil. It was more work to blow Grant. That’s why it was called a blowjob.

Grant knew the smart thing to do was to leave. But his cock was in Vonda’s mouth. She implied she wanted him to cum on her face. Would that be better than fucking her pussy?

He decided to stay. It was unlikely Basil would return any time soon.

As he drove back to his office, Basil cursed himself for not having the courage to tell Vonda he wouldn’t be able to fuck her for a year. He knew she wanted a baby. He knew she loved fucking him. It would be a crime to make her wait a year as well, but he had his fingers and mouth. He could make her cum that way. He could buy her toys.

Keeping Vonda in line would be easy. 

 

It had been easy convincing Ethan to let her tie him down to her bed. He was almost eager to do it. Once he had agreed, he stripped down and she helped him put the cuffs on his wrists and ankles. From there it was easy to attach each limb to a corner of the bed. 

Lorraine had laid out the ball gag that was part of the restraint kit but she didn’t insist he put it in his mouth. Partly because she wanted to hear his moans, partly because she wanted to ride his face with her pussy, but mostly because she needed his face unobscured.

“You’re so pretty,” she told him and followed the words with a kiss, pushing her tongue deeply into his mouth. 

Ethan gasped when she pulled back from the intense kiss. “I wish you wouldn’t call me pretty,” he complained.

“Why not?” she teased him. She was wearing a modest bra and panty set that was thin enough that he could just barely get the outline of her nipples and labia, which was nice but his cock was already hard. He didn’t need to be any harder.

“It’s…a bit humiliating. Emasculating. Couldn’t you say I’m handsome or attractive?”

Lorraine chuckled and gave him another quick kiss. “You’ll think differently when you’re older,” she assured him.

Before he could complain, she moved on the bed, straddling his face. She lowered her pussy down on him. Ethan didn’t mind, though the experience would have been better if she had removed her panties. Even so, he could smell her pussy through the thin material. Before she sat on his face he could see they were damp with her amrita soaking through. Once she had mounted him, he could taste her pussy and he moaned softly.

Wrapping her hand around the base of his hard cock, Lorraine licked off the bead of precum that had formed on the tip. His moan reverberated from his throat to her pussy. She enjoyed that.

With no intention of sucking him off, Lorraine sat up and pulled aside the crotch of her panties, giving Ethan full access to her pussy.

“Make me cum,” she ordered him, moving her hips to give him easy access to her clit. 

Ethan knew just what to do. They had been playing together for months now and he was accustomed to her wants and needs. Being pinned down like this made it more difficult, but it made it more fun as well.

The orgasm he gave her was pleasant enough to make her want to move forward with her plan.

“I love it when I can barely breathe and you ride my face,” he panted when she got off him.

Once more Lorraine chuckled and gave him a kiss on the lips. She tasted herself and, as always, found it rather pleasant.

“We’re going to play a game,” she told him.

“Okay, what sort of game? Do I get to cum at the end of it?” He grinned at her confidently.

Not answering right away, Lorraine went to the pile of Ethan’s clothes and searched through them until she found his pants and his phone inside the pocket. “We’re going to play Truth,” she said.

“Truth or Dare?” he asked.

“No. Just Truth,” she answered. “Are you seeing and fucking someone other than me?”

He saw his phone in her hand but said nothing about it. He wasn’t worried. She didn’t know the passcode.

“Yes,” he said comfortably. He had told her about Gemma before.

“What’s your girlfriend’s name?” Lorraine asked.

“Gemma.”

“Does she know about me?”

Ethan hesitated. “No,” he answered finally. 

“But I know about her.”

“Yes…”

“What would she think about you fucking someone else?”

“Uh…I don’t know. We haven’t had a conversation about being exclusive or anything like that…”

“Honesty is the best policy, don’t you think?” asked Lorraine. “I think you should tell her you have a woman you’re fucking on the side.”

He nodded in agreement. “I probably should,” he agreed. “But you two are never going to meet, so…”

Lorraine nodded in agreement and tapped absently at Ethan’s phone. “I want you to call her right now and tell her everything.”

“Nope.”

“How about texting her then?”

“Definitely not.”

“I’ll do it for you because…you’re a little tied up at the moment.”

“Not going to happen.”

“Hmm.” Lorraine went over to him and held the phone in front of his face. Before he realized what she was doing, the facial recognition app had opened the phone for her.

“Hmm. Let’s take a look, shall we?”

“No! Don’t! What are you doing?” For the first time Ethan truly strained against his restraints. Lorraine was a woman of means; she didn’t buy cheap toys. As hard as he pulled, he couldn’t break the bindings. 

“Any pictures of her?” Lorraine asked. “I just want to see what I’m up against.” Lorraine went into the photos app and started sorting through the pictures. 

“That’s an invasion of my privacy!” Ethan insisted.

“Yes it is. Hmm. Is this her?” Lorraine held up a picture of a pretty brunette smiling into the camera along with Ethan.

“That’s my cousin.”

“Hmm. Maybe.” She continued her search. “Oh. This is her, isn’t it?”

This time Ethan appeared in the picture with a very attractive woman with straight black hair and bright red lipstick.

He considered lying, but didn’t see the point. “Yes,” he sighed. “Why are you doing this?”

“Do you have any nudes of her?” Lorraine asked as she resumed searching the photos.

“No.”

Lorraine looked at him skeptically and moved back to take a picture of him. He glared at her, but there was little else he could do in his predicament.

“Should I send her this photo of you tied up in my bed? How would you explain that? Oh look! You have a really long text history with her.”

“Don’t…” he begged.

“Ah ha! I knew you had nudes of her!” 

Lorraine now brandished the phone showing a topless picture of Gemma who was pouting. 

“Nice tits on the girl. A little small, but variety is nice, isn’t it?” She accentuated her own tits by arching her back and showing off. “You lied to me. You said you didn’t have any nudes of her.”

“That’s just a topless picture. She’s obviously wearing pants.”

Lorraine nodded. “True enough. Where do you keep the good ones?”

With a sigh Ethan talked her through the process to open the semi-hidden folder with the many nude pictures Gemma had shared with him. As she looked through them, she was impressed. The young woman was attractive and didn’t get vulgar in her pictures. There were no full spread gyno shots. Mostly she focused on going topless and showing the curve of her ass. Occasionally Ethan popped up in the pictures with her, in an equal state of undress, and in a series where she had taken a series of selfies with his cock her in her mouth. 

Lorraine was well-familiar with that cock. She would have recognized it anywhere.

“Are you done yet? Can you untie me?”

“I haven’t texted her yet.”

“Please don’t.”

“Are you serious about her?” Lorraine asked. “Do you want to continue to date and fuck her and maybe move in together and—heaven forbid—eventually get married?”

Ethan gave the question some thought. “Maybe.”

“Then you need to be honest with her. You know. The Truth.” Clearing her throat, Lorraine activated the voice to text and spoke into the phone. “Hon, I have something serious to tell you. I need to be honest.” She then stopped. “I’ll let you have input on this. It’s going to happen.”

“Why are you so intent on ruining my life?”

Pursing her lips, Lorraine said, “I found my husband fucking another woman. I might not have been so upset if he had told me he wanted to fuck someone else. I might even have let him do it. But now he’s going to be my ex-husband. My ex-husband is wearing a chastity cage for the next year. Does that sound fun to you?”

Ethan shook his head. “No…”

“Good.” She pressed a button on the phone. “And send. Now we wait.”

 

 

Chapter 6

 

It had been a while since Basil had been inside the Kink Ink Tattoo and Piercing Parlor. It was still in a nice location on the edge of the arts district adjacent to the restaurant strip and within walking distance of the student slums. 

The last time had been under better circumstances. 

The business’s normal hours were listed on the door. The place didn’t officially open for two more hours. When Basil tried the door, it swung open. Stepping inside he saw a young woman behind the reception desk. She gave him a smile.

“Mr. Norwood?” she asked politely.

“Yes.”

“Go on back,” she told him. “They’re waiting for you.” She indicated the way.

He hated being first or last. He was sure he was last because he was ten minutes late for the appointed time.

Giving the receptionist the once over—the dyed pink and purple hair was a bit much, but he liked her low-cut blouse that showed off her substantial tits—he headed down the corridor.

Most of the doors were closed. One of the open ones had voices and light coming out of it. With a sigh he entered.

“Well, I’m here. Let’s get this over with.” He interrupted the quiet conversation that had been taking place. Smirking, he looked around the room. 

He nodded once at his lawyer. As always, Wynona looked put together and professional. Basil couldn’t stop thinking about what she would look like naked. 

The other lawyer was there as well. Basil couldn’t think of his name immediately. George, maybe? He nodded once at his wife’s hired gun.

It had been months since he had seen his wife. Basil didn’t let his gaze linger on her. The last thing he wanted was for Lorraine to think he still desired her, even if he did. Even if she was still a hot piece of ass.

At least he was going to be able to get his dick out so everyone could admire it.

Trixie, the part owner of the parlor, and also the full-time piercer, was seated on a rolling stool in the corner of the room. As part of the dress code of the parlor, and to give it the sheen of an upscale operation, she was wearing medical scrubs. They were pale blue and had her name and the insignia of the parlor embroidered on the breast above the pocket. Incongruously, beneath the short sleeves of the scrub top, her arms were covered in flower and butterfly tattoos. It was sort of sexy in a trashy way.

“Are we all here?” asked Wynona.

They all looked around and nodded at each other. 

Turning to Trixie, Wynona asked the piercer, “Are you sure you’re fine with doing this?”

The short woman with the dyed black hair cut on a bi-level, nodded once curtly. “This isn’t the weirdest thing I’ve been asked to do while working here.”

Basil wanted to add that it was probably the most profitable thing she had ever done. He knew that because he saw the prepared invoice for her services. 

“Anyone have any last minute questions or concerns?” Wynona asked.

Everyone remained silent.

“I’m going to remind everyone here that while, strictly speaking, this is not illegal, it is questionable for a divorce decree. The dollar amounts for the agreement have been finalized and Ms. Stanford has deposited the requested money into the escrow account which will be paid out to Mr. Norwood at the appropriate times.” She pulled the short contract from her briefcase. “I think we all need to sign and verbally agree to keep this on a need to know basis.”

The paper made its way around the room with everyone signing, even Trixie.

“Are you sure you all want to watch?” asked Trixie.

“I think it’s going to be necessary,” said Spencer. 

“Definitely,” agreed Lorraine.

Basil bit back the snide comment that was on his tongue.

“If you would…uh…unzip, Mr. Norwood,” said Trixie. 

She hadn’t been so shy when she had shoved a needle through his dick several years ago, that Basil definitely remembered. But then again, when that had happened, the audience had been one person: Lorraine. 

Smirking, Basil unzipped his pants and, without being told, he pulled out his cock. For a man of short stature he was inordinately proud of his manhood. It wasn’t any more impressive to Trixie than the dozens, perhaps hundreds, she had seen in her time. It was—at best—average, even with the thick CBR in the PA piercing. Spencer glanced and then looked away. Surprising herself, Wynona looked at her client’s penis and critically evaluated it. If anything, the piercing made it look smaller, but she wasn’t a size queen so she didn’t really care.

Only Lorraine was bored by the display.

“You’ll feel some tugging. If I do anything painful, let me know,” Trixie told him.

“I can deal with a little pain.” He sniffed. “Hell, I can deal with a lot of pain.”

On the advice of her counsel, Lorraine remained silent.

“I sterilized the cage before you arrived,” Trixie assured him as she started to work. “You can come in any time to be inspected or for a cleaning.”

“He’s also required to report to you regularly to make sure it hasn’t been removed or tampered with,” Spencer reminded the group. “We’ll print a schedule for you.”

“It’ll be worth the twelve mil,” said Basil.

Trixie worked efficiently. She had done this before, more than once. Many times, in fact. First she used the specialty pliers to open up the CBR and remove the bead before sliding out the ring, being careful not to pinch flesh in the process.

The next step was to slip the retaining ring behind his balls. That was easy. They had chosen a solid ring, less seams being more hygienic. She noted that Basil had removed all of his pubic hair. Probably through waxing. Maybe a laser. He was very smooth, she could feel that even through the nitrile gloves. Once the retainer was in place, she moved onto the main shaft of the cage. 

At the front was a curved hook that was essentially the ring of a CBR that was welded to the shaft body. It took a bit of lube and some maneuvering, but eventually Trixie got it through the fistula and out through the meatus. 

From there it was just a matter of lining up the various parts with the lock. Once the lock was in place Basil’s penis was effectively encased in a cage of steel bars that not only prevented intercourse, but an erection of any sort.