Double Chastity
Elliot Silvestri
Double Chastity
An Erotic Male Chastity Novel
Elliot Silvestri
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.
Double Chastity
Copyright © 2023 Green Bush Publishing
First Edition
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 Green Bush Publishing 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
Harmony slowly stirred her coffee while looking at the young man across the table from her. Before she could say anything Cooper spoke first, “Do you think the waitress thinks we’re on a date?”
She waited a moment to answer, sipping from the cup before saying, “It’s more likely she thinks you’re taking your mother out for brunch.”
They were having brunch, but it was a Friday, not the weekend. Cooper had a stricken look on his face. “Do you really think…”
“I’m almost twice your age,” she quickly pointed out. “But I thought that’s what you were looking for.”
He was twenty-four. She was forty-five. Harmony liked to think she could pass for early thirties. She knew she could because she had done it in the past.
“I…I am,” he said. “I have a thing for older women.” He put some scrambled eggs on his fork and ate them. “We’ve already discussed that.”
“Indeed we have.” Harmony ignored most of the food on her plate. She hadn’t maintained her body for all these years by indulging in consuming rich foods. “I want to take you back to my place and fuck you.”
Cooper made a strange noise, something between choking and doing a spit-take. It took him a moment to recover. Harmony patiently waited.
“Keep your voice down,” he hissed at her.
Harmony made a show of looking around the diner. It was nice enough as these places went, but it was hardly anything special. She had brought him here to gauge her reaction to him in person. Online he was charming and witty. In person he was handsome, if a little naive. “Why? No one cares what we are saying.”
That was true. The place was busy enough and everyone was minding their own business.
“Still…” Cooper looked nervous. He was hiding a secret. Harmony liked secrets.
“Most men would have been happy to jump at the chance to get into bed with me.”
Seeing that he was at a crossroads, Cooper focused himself. “I do. I want to do that. But—”
She cut him off. “You still want to do anal, right?”
He paused before answering. “Um…that wasn’t how I was going to put it.”
She smiled and leaned forward, giving him a little more of a hint of her cleavage. “That’s how I would put it. Do you want to know where I want to put it?”
Cooper wasn’t sure what he was getting himself into. That didn’t stop him from leaving the restaurant with her, however.
Harmony lived in the middle of suburbia in a small house with a neat flower garden that took up most of the property in front of the house. It was set off from the neighbors by a white picket fence. It was pleasant and unassuming. Cooper felt out of place visiting her. He liked living downtown at the edge of the art district. The rent was almost reasonable and there were a thousand things to do every night and day.
Unfortunately one of those things wasn’t fucking middle-aged women. For that he had to come to the suburbs.
He parked his car behind hers in the driveway. She gave him a nod and a wave, summoning him to the front porch where she unlocked the door. He couldn’t help but look at her ass as she walked up the four steps to the porch. It wasn’t small and trim, but full and rounded.
His cock stiffened in his pants. He was nervous and excited. It was going to happen.
Inside she led him to the kitchen.
“Drink?” she offered.
“Uh…no.”
“Fine.” Not wasting another second she abruptly turned and walked up to him, tilted her head up and kissed him.
Her lips were soft. His tongue automatically parted her lips and invaded her mouth. She happily let him explore for a moment before pushing back.
“Okay, well, it doesn’t take much to get you ready, does it?” she asked.
“Sorry. Did I seem too eager?” He hoped he hadn’t fucked things up already. He had been careful to put his hands on her hips, not her ass.
“Not too eager,” she said. “I kissed you. But I could feel your cock.”
“Sorry.”
“Don’t be. I like a hard cock.”
“Thanks…”
She smiled again. “You’re nervous. When was the last time you had sex?”
“Uh…a few weeks ago.”
That definitely crossed over the time they had been chatting online, but that didn’t bother Harmony.
“Was she your age? Was she any good in bed? How did you fuck her?”
Cooper was slightly alarmed at her forward questions. “Yeah, my age. She was…fine. Good. No complaints.” He didn’t answer her third question.
Once more, Harmony sized him up. She pointed down a hallway. “My bedroom is down there, on the left. Go there and get undressed. I’ll join you in a minute.”
“Uh…really?”
“Yes. Really.”
“Where are you going?”
“To put on something a little more comfortable.”
Harmony was wearing a brightly colored floral dress that showed off her curves without being overtly sexy and just hinted at her cleavage. To Cooper’s eyes, it looked very comfortable. She had kicked off her shoes at the front door and was padding through the house in stocking feet. He wondered what she was wearing under the dress. It was obvious she had planned to bring him back to her house; that had been their general plan all along.
“What are you waiting for?” she asked.
He realized he had been deep in thought and hadn’t moved.
“Right. Sorry.” It was all he could do to prevent himself from running down the hallway and tearing off his clothes.
Her bedroom was nice. Somewhat plain, but nice. The wallpaper was a floral print as was the bedspread. She only had a queen-sized bed, but she hadn’t promised him an orgy, had she? The nightstand, dresser, and bed were a matching set, all yellow.
Briefly Cooper wondered if he was being set up. They had been flirting and sexting for almost two months now so he was reasonably sure he was safe.
He threw caution to the wind. As long as he got fucked, he didn’t care what happened next.
Kicking off his shoes, he quickly stripped off his jacket, polo shirt, pants, and socks, leaving them in a pile next to the bed. He stopped at his tight red boxer briefs. His cock was bulging underneath them and he wondered if she wanted him completely naked or if she wanted to strip off the last piece of clothing in a special reveal.
He could have posed on the bed, but that seemed silly. Instead he looked out the window onto the back yard and saw that she had very little lawn and a whole lot of flower beds. Cooper couldn’t name any of the flowers other than a stand of sunflowers.
“I thought I told you to strip,” said Harmony.
He turned around to face her.
“Holy shit,” he breathed.
His cock was already hard but that didn’t stop it from throbbing in anticipation of what was to come. He hoped.
Harmony had removed her dress. Her long chestnut colored hair was pulled back into a severe bun at the nape of her neck. What she had on now she must have had on underneath her dress earlier because there was no way she had changed outfits so quickly.
Her top he could only describe as a corset. Maybe it wasn’t a real corset, but it pushed her tits up to create some impressive cleavage that her dress had been partially hiding. He knew it had to be a bra because it didn’t go all the way down her body to her hips, but he didn’t care what it was called. It was black, contrasting sharply with her pale skin, and some of the black material was opaque, but the panels over her nipples were sheer. He could see her hard nipples pressing at the thin material.
Around her waist she wore a classic garter belt, also black, which matched the bra and the tiny panties that hid her pussy. Or maybe it didn’t really hide her pussy because the front triangle was sheer showing she had no pubic hair. Maybe it was a thong or g-string. Cooper wanted to know but wanted to drink in her body before he found out.
The garter belt’s suspenders were attached to sheer stockings that came up to mid-thigh. Unlike the rest of her lingerie the stockings were nude rather than black. But that only made sense with the floral dress she had been wearing.
Harmony stood in front of him for a long moment, letting him get his fill of her body. She knew exactly what she was doing.
“Holy shit,” he said again. “Did you…did you have that on underneath your dress?” He had to know the answer to that question.
“Yes, of course. A lady is always prepared.” She frowned at him. “I thought I told you to strip. Your underwear is still on.”
“Right. Sorry.” He hooked his thumbs into the boxer briefs and was about to pull them down because at that moment he would have done anything she asked.
“Wait. Stop. Let me.” She took three confident steps toward him, he noted she still wasn’t wearing any shoes, and then knelt down in front of him.
Kneeling should have made him feel like he was in command of the situation. It didn’t. He felt completely vulnerable. She was in charge.
Harmony hooked her fingers into the elastic waistband of his underwear and pulled them down. His cock sprang out. She smiled and curled her fingers around his shaft.
Cooper shivered.
“Allow me,” she said before putting his cock between her lips that he only now noticed had been painted bright red. She must have done that when she sent him to the bedroom.
She fellated him for less than a minute. She didn’t need to get him hard and she certainly wasn’t going to let him waste his load in her mouth.
“I love sucking cock,” she said, rising to her feet.
“I can tell,” he said, his voice shaking. He wanted to grab his cock and jerk off but he managed to control himself.
It was a huge effort because when she got to her feet, she turned around and walked to the nightstand next to her bed.
She was wearing a g-string.
She had a ripe, full ass.
Cooper wanted to fall on his knees and press his face between her fleshy globes and worship her.
He was frozen in place. That was for the best.
Harmony bent over—again, knowing exactly what she was doing—and opened the nightstand drawer. “Here it is. Thought I had it in the other room.”
Plucking the object from the drawer she turned around. “Lay down on the bed. I can’t wait to fuck you.”
In one hand she had a jar. In the other she had a tangle of black polyester and nylon straps. Cooper knew exactly what both were.
The jar was full of lubricant.
The straps were a harness for the dildo mixed up in the bands.
They were really going to do this.
She handed him the jar. “You know what to do with this, right?”
Cooper nodded.
Harmony then expertly untangled the mass of straps and proceeded to pull on the harness like a pair of shorts. There was a strap that went low around her waist and one each of her legs, plus another that went between her legs. The straps were already adjusted to her body. When everything was in place Cooper focused on the flesh-colored dildo that jutted out from Harmony’s crotch.
It fell somewhere between realistic and completely fake. Cooper wasn’t sure which end of the spectrum would have been better, so this was a good solution.
Harmony looked up at him to see that he hadn’t moved.
“Are you nervous?” she asked. “Do you not want to do this?”
He shook his head. “No! I want to! It’s just that you’re so beautiful…”
She laughed at him. “Okay, that’s a sweet thing to say. But I fully intend on pegging you. If it goes well, then maybe we can plan on doing other things later.”
“Right, right! Gimme a second.” As fast as he could, Cooper got on the bed and lay on his back. She looked expectantly at him. “Oh. Right.”
He knew what he had to do but he had never done it in front of another person before.
If he wanted to go through with it, he needed to throw away his shame.
Cooper opened the jar and got some of the slippery lube on his fingers. He then drew his legs up to his chest, exposing himself to Harmony.
She watched with disinterest.
He smeared the lube on his asshole and then was bold enough to push his finger past the sphincter, getting some of the lube inside where it would do the most good.
Seeing that he had properly prepared himself, Harmony dipped her hand into the open nightstand drawer to pull out a condom packet. This she rolled onto the artificial phallus and then dipped her fingers into the lube jar, rubbing it on the head and length of her shaft.
“Ready?” she asked him.
There was only one correct answer.
Cooper nodded.
She directed him to put a pillow under his ass and then to hold the back of knees. It felt wrong and it felt wonderful.
Harmony moved on top of him. It was a perverse twisting of two lovers in the missionary position. She held the fake cock in one hand and placed her other hand on his chest, bracing her position.
It felt ungodly weird to have something probing at his asshole.
“Just relax,” Harmony murmured to him. “I’ve done this lots of times.”
He wasn’t sure if that reassured him or not. He tried to relax and just breathe while telling himself that this was normal and natural and sexy and fun.
When she abruptly slipped inside him he gasped in delight. She laughed at his reaction.
“Oh! Your ass is very eager, isn’t it?”
“Yeah…” He couldn’t believe he was doing this.
Harmony put her weight onto his chest, still leaning on her hand. She wiggled her hips, getting adjusted. “I’m so turned on right now,” she said.
“You are?” He was dumbfounded.
“I like fucking men in the ass. Hold your legs up. I’m going to use your asshole and you’re going to love it.”
She had taken her hand off his fake cock. It was most of the way inside his body now. Once more she dipped her fingers into the lube jar and this time applied it to his already hard cock.
Slowly she began thrusting her hips while moving her hand up and down on his cock.
Cooper moaned. “Oh…fuck yes.”
“You like that?”
“Fuck yes.”
She laughed and picked up the pace. “Too many men are afraid of being pegged.”
Cooper just moaned in reply.
“They think it’ll make them gay.”
“Uh-huh.”
“They don’t get to know how sexy it is.”
“Yeah…”
“How good it feels.”
“Uh-huh. Keep going,” he begged. His cock was throbbing. His ass was filled. It felt unusual but he quickly grew to love it.
“They don’t know the little magic button every man has inside his ass.”
Cooper was panting now. He couldn’t talk. Harmony was still holding his cock but she wasn’t stroking it at all. She could feel his heat and the throb of his lust through her fingertips.
“I love watching men cum,” she said, completely releasing his cock now and taking hold of his legs so she could fuck his ass as fast as she wanted.
Cooper’s eyes went wide when she did so. He didn’t protest. He couldn’t process everything he was feeling, both physically and emotionally. His cock was rock hard but flopping up and down in response to her thrusts, slapping on his stomach.
“Oh…oh fuck…oh shit,” he said over and over.
She didn’t stop. She looked at his cock waiting for that magic moment.
It only took a few more thrusts.
He erupted all over himself.
His thick spunk shot out of his cock landing on his neck, his chest, his stomach. There were three large spurts followed by a half dozen more that dribbled down the length of his cock. She had made him cum without touching his cock for over a minute.
“Fuck! Oh fuck! Shit!” Cooper continued cursing. Harmony stopped moving her hips. She let the orgasm wash over him. He threw an arm over his eyes, perhaps in shame of what had just happened. He needed some time to process everything.
To pass the time she looked at his cock. At its largest he was an impressive specimen. He wasn’t huge by any means, but that was more than fine with Harmony. She had been with men of all sizes and she honestly preferred an average sized cock. Too big was painful and distracting; too small was disappointing. Goldilocks had it right.
He had trimmed down his pubic hair. Cooper didn’t have a lot of body hair, which was nice, but there was no way that he didn’t trim the length of the dark curls around the base of his cock. He didn’t shave at all. She’d have to get him to shave his balls at the very least if they were to continue this.
“I made a mess,” he said after a minute.
“That’s fine. I like messes.” She ran her hand over his body, smearing the cum over his skin. He tried to shy away but he didn’t have anywhere to go. “It’s sexy.”
Finding a bit of courage he said cautiously to her, “Did I do good?”
She laughed. “You did wonderfully. Very sexy. I loved the way you came. Did you enjoy your first prostate orgasm? Or have you had one before?”
He shook his head. “No. I’ve never cum like that before.”
“Good. Did you like it?”
“Yes.”
“Wonderful.” She leaned forward and kissed him. “We’ll have to do this again.”
“Right now?” He was alarmed at the prospect. It had felt good but his ass felt stretched and sore.
She laughed again. “No. Not right now.”
He grimaced and wiggled around.
“Is my cock hurting you?”
“A little. I’m not used to having something up my ass.”
“Maybe you should get used to it,” she said with a giggle. “Hold on. Let me pull out.”
She withdrew the dildo and Cooper experienced a sense of loss that made no sense. Physically he felt a little better.
“Did you…did you enjoy yourself?” he asked with some trepidation.
“I like fucking men in the ass. I love pegging them. It’s been a while since I’ve taken someone’s anal virginity.” She paused. “But that’s not what you were asking, was it?”
She moved off the bed and carefully removed the condom from the dildo, dropping it into a wastepaper basket on the far side of the bed. It was like it had been set there for just that purpose.
“No, not exactly.”
She turned back to him and loosened the straps to the harness. He suddenly felt even more vulnerable. She was dressed—more or less, her breasts and pussy were covered at least though her ass cheeks were exposed—while he was fully naked.
“What were you asking?” She lowered the harness and stepped out of it, placing it on top of the dresser before moving back to the bed.
“Did you cum?” he asked her.
“No. I usually don’t from pegging a man.”
“I’m sorry.”
“Don’t me. I still enjoyed myself.”
“I can make you cum,” he said boldly.
“How are you going to do that with this limp cock?” She toyed with his manhood, flopping it back and forth, emphasizing how soft and small he was.
“Give me a couple of minutes. I can get hard again.”
“I don’t doubt it. But you aren’t going to fuck me today.”
Cooper was surprised. “Why…why not?”
“I never fuck on the first date,” she said and managed to keep a serious expression for a few seconds before laughing. “Do you think we just fucked?”
“Uh…yes?”
She chuckled and nodded her head. “Yes. We fucked. We had sex. We had anal sex. I fucked your ass. I pegged you. But I don’t let men put their cocks in me on the first date.”
“Oh…why?”
“Just a rule I have. Men are so eager for sex but they usually don’t consider the woman. I made it a rule that I only let them fuck me on the second date. Maybe.”
“Do you want me to leave?” he asked. He was confused.
“Do you want to leave?”
“No. Not really. I just…don’t know what else you want right now.”
Shaking her head she leaned forward and gave him another kiss, this one quick and on the lips.
“You’re so young and innocent. I want to get off. I want to cum. I have needs just like you.”
His brow furrowed. “But you said you didn’t want me to fuck you.”
“That’s right. But you have fingers and a tongue, don’t you?”
“Yeah…”
“And if those are no good I have three different vibrators in my drawer. All of them have proven more than competent at getting me off.”
“What…what do you want me to do?” Cooper was confused and uncertain. Dating an older woman like Harmony was confusing.
“Let’s try this. I want you to go down on me. If you can eat me out and make me cum, we can talk about a second date.”
“I can do that!” he said eagerly.
“Good boy,” she said and knelt up, pulling the sides to her g-string down over her hips. It took him a second to realize that she was wearing the undergarment over her stockings and garters. Did that make her a slut? He hoped so.
Once the sheer garment was off her legs and tossed aside like a wisp of nothing he saw that her pussy was completely shaved. He wanted to touch it and feel how smooth her skin was.
“Should I clean up first?” he asked, indicating the cum she had smeared all over his chest and stomach.
Harmony shook her head. “No. Of course not. I like a dirty man.” She rolled onto her back and spread her legs, exposing her pussy. Her lips had opened up just a little. He could see moisture on them. This play had turned her on more than he had realized. She pointed to her sex. “Your tongue, my pussy. Let’s see if you can make some magic.”
Cooper moved into position between her legs. He thought back to high school when he had first eaten pussy. Kara wasn’t exactly his girlfriend, but she was willing to have sex with him. He considered himself a pussy connoisseur after that.
Harmony lay back and relaxed. Cooper did everything every woman he had ever been with said she liked when it came to cunnilingus. He licked her lips. He gently sucked her clit. He put his fingers inside her and artfully stroked that little hidden spot. He used his tongue and lips and entire face when it seemed right. He listened to her breathing. She gave short, one word directions and guided him by putting her hand on his head.
It was an effort but he was delighted when he made her cum.
It wasn’t Earth-shattering for Harmony, but it was acceptable.
“That was nice,” she said. “Now get dressed and go home. I’ll call you when we’re going to do this again.”
Cooper wiped his face with the back of his hand. The scent of her pussy clung to his skin. He could feel the dried remains of his cum on his skin. “Could I take a quick shower?” he asked.
Harmony laughed and shook her head. “No. I want to send you home like the dirty boy you are.”
Chapter 2
Cooper managed to get home early and went right to the shower. He felt dirty and guilty and ashamed.
But he knew that when Harmony called him again, he’d go right to her and fuck her.
No, he thought as he paused in his shower, soaping up his face for the third time to make sure her amrita scent was completely washed away, he’d let her peg his ass again. She seemed to like doing it and he wanted to do it again. He desperately wanted to do it again.
He just wished he could ask his girlfriend to do it to him.
And just like that the guilt came back.
He was certain that Mallory loved him. That was the problem. He couldn’t ask her to peg him. She wasn’t embarrassed or shy about sex, but that was a kink too far for her. He was positive about that.
And truth be told, he sort of liked sneaking around behind her back.
He couldn’t wait for Harmony to contact him so she could peg him again.
He’d just get it out of his system and then break it off with Harmony. Then everything would be fine and he could focus on Mallory.
He all but dropped his towel after leaving the bathroom to find Mallory in the bedroom. “What…why are you home early?”
He didn’t want to make it sound like an accusation, but it came out that way.
Mallory didn’t notice. She was in the process of undressing. Her pants were already in a wad at the foot of the bed and she pulled off her blouse and threw it down as well, leaving her in plain flowered underwear and a white camisole. Mallory rarely wore a bra; she didn’t need to because her breasts were so small.
“I have a headache,” she complained as she slipped into their bed.
They had only been living together for six months, having been dating for just over a year now. The only real complaint that Cooper had—beyond the lack of pegging—was Mallory’s frequent migraine headaches.
“Bad one?”
“Yeah. I had to leave work. Turn off the lights. Close the blinds.” She wasn’t ordering him, but her pain caused her to be blunt. He did as she asked. From the nightstand on her side of the bed she found her sleep mask and put it on, further darkening the light that reached her eyes.
He dropped his towel and went to his dresser to put on clean clothes.
“How was your day off?” Mallory asked.
“Good,” he said. “Just…relaxed. Went to the gym. Came home sweaty. Wanted to take a shower.”
He hoped it didn’t sound like he was trying to cover up his deception with a lie.
“Want to fuck me?” she asked.
He turned. He had already put on underwear and had a t-shirt in hand. “But your headache…”
“Just let me lay back. I don’t want to move but I’m horny and I want you to fuck me.”
They had done this a couple of times before. Sometimes she got some relief from the orgasm. Supposedly semen had some chemicals in it that would help, but Cooper thought that was a myth.
When he didn’t answer her right away, she pulled up the mask just enough to reveal one eye. “You don’t want to? I understand…”
“No, no,” he said. “I just wasn’t expecting you to ask.”
Cooper didn’t want to make it look suspicious that he didn’t want to have sex with his girlfriend, but he had already cum with Harmony just an hour earlier.
He figured he could get it up for Mallory.
Tossing aside the t-shirt he dropped his underwear and joined her on the bed. Somehow, even wearing her sleep mask, she managed to reach out with her hand and find his cock.
He was soft.
He was rarely soft when Mallory asked for sex.
She didn’t seem to notice or mind.
“Come up here. I want to suck you a little.”
Cooper moved up to the head of the bed and she turned her head to take him in her mouth. Something about knowing he was going to have sex with two women on the same day excited him and in short order he was sufficiently hard.
Moving away from her he pushed down the covers, exposing her body. She didn’t protest, nor did she help, when he started easing her panties over her hips and down her legs.
Her body was long and lean. Only at that moment did Cooper realize how much thinner and taller his girlfriend was compared to Harmony. Her pussy had a narrow strip of hair just barely covering her slit. He briefly reflected on the smoothness of Harmony’s bare pussy and realized that Harmony must have her hair waxed off. It was far too smooth to have been shaved.
Pushing apart Mallory’s legs, he lowered his face to her sex. She moaned softly as he licked her slit. Her lips opened up to him and he tasted her amrita. More soft moans filled the air as he ate her pussy. With his free hand he pumped his cock, making sure he stayed hard for her.
“Please…” she begged.
He knew exactly what she wanted. He moved on top of her and pushed her legs open wider. It was easy to slip his cock into her and start pumping away.
It was a bit disturbing to fuck a woman who was masked and softly moaning, but Cooper knew that he had to perform.
Having sex with his girlfriend suddenly seemed like the most normal thing in the world at that moment. He kept his motions slow and gentle until she asked for him to go faster.
“Faster, not harder,” she mumbled. “Make me cum. Put me to sleep.”
He knew he could hold off long enough to make her climax. The real trick would be to cum shortly after her so she wouldn’t get annoyed at his need to continue to fuck.
Mallory was easy to please in bed. He hoped that didn’t make him a lazy lover. It only took a couple of minutes to get her off. He recognized the sudden change in her breathing and the way she clutched at him before her entire body tensed up.
Not wanting to lose the opportunity to cum in her and give her the relief she needed, Cooper focused on the fantasy that first came to mind: Mallory watching in horror as he was on his hands and knees getting pegged by Harmony.
He came hard. It was much more intense than he had expected.
“Thank you, thank you, thank you” she whispered several times before rolling away from him. In a moment she was asleep and snoring softly.
Cooper briefly considered going back to the shower. Instead he left her alone in the bed, covering her up, before going to the bathroom to wipe off his cock with a wet washcloth.
He stared at himself in the mirror for far too long before he was able to stop hating himself.
Chapter 3
Harmony: Are you free tomorrow afternoon?
Cooper looked at the text on his phone for a long moment. Hiding Harmony’s contact information on his phone under the work sub menu was slimy, but he needed to do it. He didn’t want to be caught.
Mallory was in the kitchen happily making dinner for the two of them. Texting the woman who had fucked his ass while his girlfriend was being the perfect domestic partner was very, very wrong.
He responded as quickly as he dared, pausing the game he was playing to do so.
Cooper: I’m working
Her response was quick.
Harmony: You have one of those shitty jobs that you can’t get away from?
Cooper: Yes
Cooper: I have tomorrow morning free though
That wasn’t exactly the truth. Working in IT he had some leeway with his hours and no one would expect him to show up in the office before noon. Mallory would have gone to her job early, Monday being their busy day.
Harmony: I hate working under a deadline, but for you I’m willing to do it.
Harmony: My place 8am?
Just seeing the words made Cooper get hard. He wanted to say no, but his body and his lust told him to say yes.
He gave in to his desires.
Cooper: Yes
Harmony: Be sure to bring your ass.
Cooper felt guilty about hiding this from his girlfriend. Mallory was wonderful and loving, but he promised himself it would only be a few times and then he would end it with Harmony having gotten the pegging fantasy out of his system.
He didn’t want to acknowledge how good the guilt and secret relationship felt.
The way Mallory gave him a little kiss when he came to the table for dinner made all of those feelings much more intense.
The next morning he was sure to bring a change of clothes with him. He even stopped at the store to buy a pack of baby wipes just in case Harmony wanted to send him to work with cum and her amrita all over his body.
He wasn’t sure what to expect when he rang the bell to her place. Would she be wearing the same outfit? Something different? Sluttier? Sexier? Plainer? Would she be naked except for the strapon harness?
The last thing he wanted to admit to her was that he had fantasized about sucking her fake cock while fucking Mallory the previous night. No one wanted to hear that.
He was semi-disappointed when she opened the door wearing what could only be described as a business casual outfit. It was fine, but plain.
“Have you had breakfast?” she asked, inviting me in.
“Uh…yeah.”
“Good. No time to waste.” She stepped in front of Cooper before he could move out of the foyer. “Strip.”
“What?”
“Strip,” she said, looking up at him. He was at least a foot taller than her. Perhaps the size difference hadn’t been as noticeable before when she was in heels in the restaurant and they had been horizontal on the bed, but it struck him now. Even though she was shorter than him, she seemed to have authority over him. Maybe it was her age, maybe it was the way she conducted herself, but it was probably his need to be pegged by her again.
“What? Why?”
“I can’t peg your pretty little ass if you have your clothes on, can I?”
“Right, right.” Cooper undressed. He kicked off his shoes, pulled off his shirt, dropped his pants and pulled off his socks, but when he started to take down his boxer briefs, she stopped him.
Her hand cupped his stiffening cock through the material.
“Eager to see me?”
“Yes,” he moaned.
She tilted her head up and pursed her lips. He got the hint and bent his head to kiss her.
It was then he realized the front door was open and Harmony’s storm door was a full length glass pane. The chance that someone would be walking by and see them was remote, but still it wasn’t something he wanted to do.
As they kissed her hand went into his underwear. He shivered when her fingers curled around his shaft.
“Good boy! You’re already hard for me.”
“Are you going to fuck my ass?” he asked, trying not to sound too eager.
“I’m going to peg your pretty little ass,” she promised.
He didn’t resist as she tugged down his underwear, letting it slip to the floor, exposing him to passersby.
“Want me to suck your cock?”
“Right here?” he asked, his nerves suddenly spiking.
She licked her lips and glanced at the open door. “Right here, right now. If you say no, I’m not going to suck it at all today.”
Regretting it right away, Cooper nodded.
Harmony fell to her knees and licked the length of his cock’s underside, taking the head between her lips and sucking eagerly.
Cooper shivered at the attention. In only five seconds she already had him on edge, ready to cum.
Her fingers gripped his balls, circling around them, pulling them away from his body, separating them. He liked being under her power.
“Do you want to cum in my mouth?” She looked up at him.
“I want to cum…”
“If you cum right now I won’t peg you, is that what you want?”
He shook his head. “No…”
“Ready to get your ass fucked?” she asked, getting to her feet but not letting go of his cock.
“Yeah…”
She released him. “To the bedroom. You lead the way. I want to look at your ass.”
He suddenly felt what it felt like when women were ogled. He sort of liked it and sort of hated it.
It was easy to remember the way to the bedroom. The sheets were already pulled back in anticipation of his arrival. There was a towel on the bed and the jar of lube on the bedside table along with Harmony’s harness and dildo. A condom packet rested discreetly on the table’s corner.
This wasn’t about romance, it was about sex.
He was fine with that.
“Assume the position.”
“What?”
Harmony laughed at his shocked reaction. “Get on the bed on your hands and knees,” she said.
“Oh, right, right.”
He crawled on the bed and then looked at her as he settled on his hands and knees. She casually undressed. She wasn’t putting a show on for him. Her business casual clothing came off to reveal a matching set of lingerie. The bra and panties were pale yellow and decorated with small flowers. The outfit wasn’t exactly sexy but it was cute and the sort of thing he would fantasize about women in his office wearing under their clothes.
He was disappointed when she didn’t remove the bra and panties. She just stepped into the harness and adjusted the straps. The fake cock hung obscenely from her crotch.
Cooper’s cock was hard; he wondered if her pussy was wet in anticipation of what they were about to do.
“Get ready for me,” she said.
“I am.”
She shook her head. “You haven’t lubed up yet.”
“Shit. Right, right. Sorry.”
“Not half as sorry as you would be if I went in dry with this bad boy.” She opened the condom packet and rolled it on as he opened the lube jar and applied the slick and viscous fluid to his asshole. She dipped her fingers in as well and added lube to the condom-covered dildo.
“Lots of men don’t like being pegged in this position,” she said as she got on the bed behind him.
There were no kisses exchanged now. This was all about the business of pegging. They both wanted to do it and it was going to happen.
“Why?”
She laughed at his question. It was ridiculous and logical by equal measures. “Because getting fucked in this position makes you gay, of course.” She grabbed his hip with one hand and the base of her strapon with the other. He sucked in a breath as she probed between his buttocks, looking for his opening.
For a second he didn’t know what to do. Getting pegged in missionary was one thing, but she was right, he suddenly felt so vulnerable and afraid, but at the same time he wanted it to happen.
The only thing to do was to reach down between his legs and grab her dildo, guiding it to the right point. His cock was hard and he was easy, so once, with his assistance, she found his opening and the right angle, it was easy for her to push all the way inside his ass.
He groaned loudly at the intrusion.
“That’s what I wanted to hear,” she praised him. “You like that?”
Cooper breathed heavily for a moment and then nodded. “Yeah…”
She withdrew the silicone cock halfway and pushed it back into him. “Like that?”
He grunted. “Yeah. Fuck my ass.”
“Do you feel gay?” she asked him.
It wasn’t a question he was prepared for.
“No…”
She frowned. “That’s fine. Why don’t you jerk yourself off while I fuck you?” she suggested.
Her suggestion seemed wrong at first. He wanted to cum just from having his ass fucked, but he realized that it didn’t make sense one way or the other. He just wanted to feel dirty doing this.
Jerking off would help that.
Balancing himself on just his knees and one hand, he started jerking off with his right hand as Harmony set up a steady rhythm fucking his ass.
It felt good. It felt really good. He wondered what it would feel like if there was a third person in the bed, a woman he could fuck with his cock while Harmony fucked his ass.
Abruptly she fully withdrew the dildo. He moaned in frustration. He could jerk off by himself any day of the week. He had come to her place to be pegged.
“What’s the matter?” he asked. He even stopped playing with his cock because he didn’t want to cum this way.
“Just giving you a rest. I want to get a good look at you.”
The room had an overhead light, but most of the illumination was coming from a pair of windows that looked onto the backyard. The curtains weren’t drawn. Light was streaming in. He started to turn around so she could see him, but she grabbed his hips and held him in place.
“No. Don’t move.”
“Okay…”
Looking over his shoulder he could see her bend down to look at his asshole. Oddly, she didn’t touch him there, but lower down and forward. Her fingers traced over the thin skin of his sack and along his taint. It felt incredible. Using her other hand she reached forward between his legs and gently touched his cock, but just barely.
“You have a nice cock,” she complimented him. “Just the right size.” Her forefinger found the sensitive spot just behind the meatus. He gasped. “And sensitive too. I like that.” Her fingers traced down the underside, over his sack, along his perineum, to just outside his asshole. “Want me to put it back in?”
“Yes,” he said firmly. He was under her control and he loved it.
While she didn’t exactly shove it back in, she wasn’t gentle about it, but he was well-lube and ready for her. His asshole easily took the dildo a second time.
They got down to the serious business of pegging. She went harder this second time and he loved it.
Without her having to ask he started pumping his cock.
“Don’t cum until I tell you,” she said.
“Uh-huh…”
“I’m warning you. Cum without my permission and we’re never doing this again.”
That was more than enough threat for Cooper.
“Tell me when you want me to cum,” he said.
She threw back her head and laughed as she continued thrusting her hips into him. “No, you tell me when you’re about to cum and then maybe I’ll give you permission.”
It was a game. Cooper was fine with that. He was enjoying the sex and if she was giving him commands like this, she was liking it as well. For just a moment he wondered exactly what she was getting out of this. While she might like pegging men, did she get any sexual pleasure from it? Did she cum from it? Would she make him eat her pussy again?
“Oh fuck!” he blurted. “I’m close. I’m going to cum!”
She stopped moving. “Don’t you fucking cum!” she ordered.
He stopped pumping his cock with his hand and put it down. Her dildo was still up his ass and he tried not to focus on that pleasure.
“I won’t,” he promised.
“Get the towel and put it under your cock. I don’t want you dirtying my sheets.”
The towel was at the edge of the bed, just within reach. Using one hand he quickly unfolded it and placed it under him, doing his best to judge where his cum would land when he ejaculated.
“Good boy.” The compliment caused his cock to jump.
“Th-thank you.”
“Think you can cum without touching yourself?”
It was a challenge that Cooper wanted to meet.
“Yes.”
“Good.” She ran her hands over his back and ass. “You’re one of those good boys who has that magic button inside his ass. You can cum from being fucked in the ass, can’t you?”
Her words of encouragement was all he needed.
“Yes.” He nodded firmly.
“Let’s make it happen. Chest down to the bed, ass in the air.”
He adjusted his position. It made no sense but it made him feel more vulnerable with his ass like that. It was a position he had fucked women in the past, a position he had seen plenty of women assume in porn. He had never done it himself.
Harmony knew exactly what she was doing. Once he was done moving she fucked his ass with enthusiasm. He could only moan and gasp. He wanted to hold back cumming, but he barely lasted a minute before she was done with him.
It was a painful orgasm. But it was also an orgasm like none he’d ever had before. Maybe the one he had had when she had first pegged him, but this one seemed better, different.
His asshole tried to tighten up on the dildo, but it really couldn’t. His balls tightened up to his body. He felt the orgasm in the root of his cock. It seemed like the cum wouldn’t stop, her ejaculated five, six, seven spurts and only then did it stop to a series of some dribbles.
“Good boy,” she said again.
He was starting to desire that praise. It felt almost as good as the orgasm she gave him.
He hated it when she pulled her faux-cock out of his ass.
“That was incredible.”
She slapped his ass and laughed. “Thank you. I think of myself as a very accomplished cockswoman.”
The name she gave herself made him chuckle. He had to ask the question. “What do you get out of this, out of pegging me?”
This topic had been skirted in their conversations before. He wanted a more direct answer.
“I like dominating young men. I like pegging them. It gives me a thrill that I can’t get with men my age or just getting fucked with their cocks.” She paused and thought for a moment. “I like pegging young men because I like knowing that I can still attract men, young handsome men.”
Before he could let the compliment go to his head she said, “Clean up your mess. Don’t get any cum on my sheets.”
She flopped off the bed and took off her harness as he wiped his cock with the towel. None of his semen had gotten on her clean sheets.
“Do you need to use the bathroom before you make me cum?”
He looked down at his now limp cock. She had spent him completely.
“I don’t think I can do anything right now.”
She smirked at him. “Like I’d let you use your cock on my precious pussy. You haven’t earned that yet.”
Earned it?, he asked himself.
Pulling down her underwear Harmony lay down on the bed. “You can use your mouth and fingers on me. Make me cum again like you did last time.”
That wasn’t a problem for Cooper. He noted that the crotch to her panties were wet, but that was only because her pussy was soaked with her amrita. She hadn’t been lying. Pegging him—and presumably other men—really did get her off. Maybe she had orgasmed quietly while she had been fucking him.
Cooper dove in between her legs and started licking and sucking with gusto. He quickly decided that she didn’t shave her pussy; she got waxed. Her sensitive skin was baby-smooth. He loved that.
Using all his tricks Cooper quickly had her on edge. He noted she liked it when he firmly sucked her clit while teasing her asshole with his finger. Maybe Harmony liked some anal play for herself. He didn’t violate her trust by attempting to violate her ass with his finger.
When she was close he wrapped his arms around her thighs and sucked on her clit. That made her cum. Her amrita ran steadily and soaked his face. He swallowed it, considering it an honor. He wondered if she would have soaked the bed if not for his mouth.
After her climax had faded she pulled him up to her and kissed him without the least bit of shyness. Obviously she didn’t mind the taste of her pussy on his lips, tongue, and face.
They held each other like lovers for a few minutes. He enjoyed the comfort of her skin against his.
“The next time we do this you have to do something different,” Harmony told him.
Cooper’s heart jumped. She wanted to do it again!
“Yes. Sure. Anything.”
She ran a finger over his lips and chin. “Anything? Don’t make that promise.”
“Anything,” he repeated.
“Good. Then I want you to shave your cock and balls. Everything needs to be smooth all the way back to your pretty asshole.”
Chapter 4
Cooper delayed and delayed and then delayed again. His schedule wasn’t lining up with Harmony’s, which gave him time to dither. In the meantime, he made sure that Mal was happy. He didn’t insist on sex every night for the next week, but he did offer. More often than not she accepted.
When they had sex it was gentle and loving. Every time he put her to sleep happy; she was grateful for the attention. Her migraines had seemed to diminish in intensity and duration, which he was grateful for. He loved Mallory and didn’t like to see her suffer because of her migraines.
Harmony gave him a deadline. Monday morning, like the previous week, or she wouldn’t see him again. She didn’t have time to waste with a man who didn’t want to bow to her wishes.
Cooper had gone almost a week without getting pegged and he realized he needed it. There was no way he was going to ask Mallory for it. There was no way he was going to confess his misdeeds to her. The only thing to do was to give in to Harmony.
It wasn’t the sex that bothered him now; it was having to shave. And it wasn’t so much the shaving—the hair would grow back—but it was knowing that Mallory would ask why he had suddenly removed all his pubic hair.
She left for work early on Monday morning, as usual. He jumped in the shower and borrowed her razor without telling her. After a near twenty minute shower the hot water started to give out and he realized that he had a lot of body hair even though he didn’t think he was particularly hairy. Cooper decided he was done before the hot water was spent. It wasn’t perfect, but it was good enough. If Harmony wouldn’t have him this way, it wasn’t worth it. That’s what he told himself.
He looked at himself in the full length mirror on the back of the bedroom door. He couldn’t decide if he looked ridiculous or younger or what. He rubbed in some skin lotion and hoped for the best. After checking Mallory’s razor for the hundredth time, making sure all his hair was gone, he double checked the bathtub drain and flushed the last of his hair down the toilet. He couldn’t leave evidence in the garbage can.
When he arrived at Harmony’s house, she opened the door, this time wearing a red and black flowered dress. “You’re late,” she pointed out. It was eight fifteen. He was supposed to arrive at eight am.
“Sorry. I was getting ready for you.”
She closed the door. There wouldn’t be any casual exhibition today.
“Let’s see then. Strip.”
He did so eagerly, wanting her to inspect him and see what he had done for her. This time she allowed him to remove his own underwear. He liked being naked in front of her while she was fully dressed. It was impossible to hide his growing erection when he dropped his pants.
Harmony nodded in approval. “Shaved. Very nice.” She reached out and gently caressed his cock. To Cooper it looked bigger than normal. Was that because he was eager to get pegged or because his body hair was gone giving him a larger appearance?
“How…how do you remove your hair?” he boldly asked her. It seemed wrong to ask about her personal grooming.
“I get waxed, but I’ve considered permanent laser removal,” she said. She trailed her fingers over his pubic bone, feeling the smoothness that would be replaced by the next day with a bit of stubble. “Would you like a blowjob?” she asked abruptly.
He blinked. “Really?”
She tilted her head. “Yes. Why? What were you expecting? To get pegged?” She licked her lips which were painted bright red, matching the flowers on her dress.
“Well…yes.”
Harmony laughed. “I just like having a cock in my mouth. I’m not going to let you cum.”
His eyes went wide. “You’re not?”
“Not in my mouth.”
She led the way out of the foyer. Her dress clung to her hips and ass. Cooper followed his cock.
When he arrived in the bedroom Harmony was reaching behind her back in an effort to catch the zipper. “Here, let me,” he offered.
“Very generous.”
He unzipped her and she allowed the dress to puddle at her feet. She had on black thigh high stockings, a pair of full-coverage high-waisted black panties and matching bra covered in a floral design picked out in red thread. He marveled at the fact she had so much interesting lingerie and had bothered to match it to her dress. And shoes, he realized when he saw she was wearing bright red high heels.
“Ever been tied up before?” Harmony asked him, indicating the bed.
The top corners had straps attached to the corner posts with thick leather cuffs attached to the straps. There were more straps and cuffs on the bed as well. Cooper wasn’t an innocent; he knew what the equipment was for.
“Uh, sort of, well, no. I’ve tied up girlfriends in the past…but with nothing like these.”
“Amateur,” she teased. “But everyone starts somewhere. Lay down. I’ll put the cuffs on you.”
Up to that moment Cooper thought that he was going to tie up Harmony. When she told him to lay down, it suddenly all made a lot more sense.
The smart thing would have been to say no. The truly smart thing would have been to say no to meeting Harmony in the first place.
He lay down on the bed and Harmony helped him put on the cuffs, making sure they were tight enough to hold him but not so tight they were cutting off his circulation.
“These go just above your knees,” she said, picking up the second set of straps that weren’t already attached to the bed frame.
He knew he should have said no. Instead he allowed her to put them on him. His erection didn’t abate at all through the process. He wanted this to happen. Of course, it was easier to maintain an erection when she kept stroking and teasing him as she tied him up.
In short order the cuffs on his lower thighs were hooked to the ones around his wrists, pulling his knees up to his chest, leaving his ass and cock fully exposed.
He liked the position; it left him vulnerable.
“God I love a man who can hold an erection like you,” she said, running her hand over his cock and balls, down to his perineum, and circling his asshole.
He shivered away.
“You like that?” she asked.
“Yeah…”
After pulling her hand away, Harmony got out the harness and jar of lube. She let him watch as she took her time putting on the harness and then adding a condom and lube.
“Ready for me?”
“Yes.”
“No you aren’t. Your pretty little asshole needs lube.” She proceeded to add lube to his back entrance. Though she had violated him with the dildo twice now, it was something else to feel her finger touching his asshole…and then to delve inside him.
“Oh fuck…” he breathed.
“Like that?” she asked as she got herself into position.
Cooper could only nod. His hands were immobilized by the bondage straps. His legs were up, practically over his head, and he couldn’t move. His cock was completely vulnerable to her.
He liked it when she eased the strapon into him.
“Ohhh…” he groaned as she filled him up.
“Good boy,” she cooed as she slowly rocked her hips back and forth fucking him. Harmony held one of his legs, steadying his body, while her other went to his cock to gently stroke him. “Good boy,” she repeated.
Cooper didn’t know how to feel. Her cock in his ass was incredible. He knew he could cum from that alone, but her hand stroking his cock at the same time intensified everything by a factor of ten. Emotionally, he felt awful because he was cheating on Mallory, and being in this feminine, exposed position, he was afraid. The fear and the guilt made everything intenser still.
He started to hyperventilate.
“You’re not going to cum too soon, are you?” Harmony demanded.
Cooper shook his head. “No…no…I’m not…but you need to stop or I’m gonna cum…”
She laughed and shook her head. “Nope. I want to see you shoot your load all over yourself.”
The curvy older woman didn’t have long to wait. A few seconds later Cooper was anxiously straining, trying to get everything to stop, but that just made him climax so hard that he only saw white for a few seconds.
He was left with his cum all over his chest and stomach. Harmony was nodding her head and holding his cock tightly. So tightly that it was almost painful.
“That was impressive,” she said. “I was trying to keep you from cumming, but you came anyway.”
Her fingers were a tight circle around the base of his cock. Before she let go he realized that she had been attempting to create a cock ring that would prevent an orgasm. That explained part of the intensity.
“Thank you, that was incredible.”
“You’re welcome.” She withdrew her cock from him and idly ran her fingers through his semen, smearing it around, and then tasting it. After giving him a wicked smile, apparently the flavor agreed with her, she did it again, but this time offered her fingers to him.
He knew enough not to refuse.
The taste wasn’t offensive but not exactly what he would call desirable.
“Good boy,” she complimented him again. He loved to hear those words.
“I’ve got a present for you before you go.”
Once more Harmony went to the night stand, this time going into the bottom drawer. What she produced took Cooper a moment to comprehend. It looked like a terrible modern art version of a flaccid cock made from anodized metal with a purple tint.
Then he realized he was seeing a cock cage.
He knew exactly what it was.
“I’m going to put this on you,” said Harmony. “I want you to wear it until I see you again. It’s up to you when that happens.”
She sat down on the bed with some baby wipes and started cleaning his cock.
“Wait! What the fuck are you doing?”
Harmony barely gave him a glance. “I already told you.”
“You can’t put that on me!” he protested even as she was doing so. He was trying to wiggle around and escape her, but Harmony had done this before.
“Hold still and let me put it on or I promise you that I’ll never fuck you again.”
Cooper stopped moving and calmed himself. “You can’t do this,” he insisted.
“It’s a fun game,” she said while circling the ring of the cage around his balls. She then proceeded to start forcing his penis down the length of the curved shaft. “Think of how turned on you’ll be all the time while wearing this. If you come by tomorrow, I’ll fuck you again and we can take it off.”
“I have a girlfriend!”
It was the only thing he could think of to say to get her to stop.
Chapter 5
Harmony stopped briefly in the struggle to close the cage around his manhood and slip the lock into place.
“You didn’t tell me that you had a girlfriend.”
Drawing heart from her stopping, Cooper said, “I’m sorry. A lie of omission. I didn’t think you’d fuck me if I told you I had a girlfriend.”
Her lips curled back into a sneer. Instead of yanking the cage off him, she instead slipped the lock into place and snapped it closed.
“Fucking leave. I don’t fuck liars.”
Cooper looked down at his captured cock. The dark purple metal surrounded his flesh and it seemed wrong on every level.
Working quickly, Harmony released the straps from his legs and opened the cuffs, freeing him. He hadn’t realized it until that moment, but his legs had started to go numb from the awkward position she had placed him in. He groaned and tried to get to his feet. The metal around his cock seemed to affect how he moved.
“Get out, get the fuck out!” Harmony seemed on the edge of exploding.
“I’m sorry,” he apologized. “But it’s just as wrong for you to fuck men half your age!” He struggled to his feet.
“You’re an adult,” she snapped at him. “And I’m an adult. We can do whatever the fuck we want. But you lied to get laid!” She went to the closet and pulled out a robe, wrapping it around her body. “Get out!” she shouted again.
Unsteadily Cooper made his way to the door and eventually to the foyer where he had left his clothes. There was no way he was going outside naked. He could get the cage off later. He spent a moment quickly dressing while sensing Harmony seething in her bedroom.
She had seemed so stable up until that moment.
“Are you fucking gone yet?” Harmony shouted from her room. “I swear to God if I come out there and I see your face, I’m going to call the cops!”
Having already put on his clothes, Cooper grabbed his shoes and ran out the door, slamming it behind him to let her know he was gone.
It felt weird and wrong to have the cage around his cock. It made walking, let alone running, feel like a foreign activity. He scrambled into his car and drove away trying not to act like he was the wheel man for a bank robbery crew.
Instead of going straight home, Cooper stopped at the local big box home improvement store. He wasn’t stupid. There had to be a way to get the cage off his cock. A quick check of his junk while in his car confirmed that the lock holding the cage closed was simple and tiny. A decent pair of bolt cutters would take care of the problem.
He judged that the smallest pair would do the job. Thirty-seven dollars would equal freedom. Though it was an innocuous purchase, he was glad for self-checkout lanes. As much as he wanted to, he didn’t open up his pants while his car was in the parking lot. That would have been risking some sort of police inquiry.
After driving home he went inside the apartment he shared with Mallory, but after dropping his pants to cut off the lock, he hesitated.