His Wife. His Keyholder. His Cuckoldress - Part 8

Click here to read the previous parts of the story.

"How long has it been?" Monica asked as she smiled at the sight of Austin's chastised cock.

"Almost a month," he replied while rubbing his cuck sitter's foot.

She laughed softly. "And your beautiful wife is adding more orgasms to Colton's count tonight, isn't she?"

Austin nodded. He was currently six orgasms behind Colton, but there was a very good chance that number would reach double digits by the time Penelope returned home the next morning. Most of their encounters were multi-orgasmic for Austin's wife and their overnight encounters always were, so he'd have his work cut out for him that week if he hoped to earn his release.

"I have good news for you," Monica said.

Austin looked up at his wife's beautiful friend and saw a sweet smile on her face. "Really?"

She nodded. "Penelope said that any orgasms you give me tonight will count towards your number. So while Colton is busy satisfying your wife's married pussy, you can try and earn the right to take your tongue to my clit to keep up with him."

Monica spread her legs and her skirt rode up, revealing a pair of sheer white panties. He saw her pussy lips through the thin, delicate material and Austin was certain he could see a hint of wetness, too.

"How many times do you think Colton will make your wife cum before he sends her back to you?" Monica asked.

"Half a dozen, maybe more," Austin answered.

Monica pulled her foot from his hand and used her toes to tease his locked cock. Austin closed his eyes and moaned. He'd been locked up for so long - and teased every single day of his imprisonment to keep him in a maddeningly horny state - so all it took was the gentle touch of her toes to put him right back in a state of intense arousal that had his cock aching in the small chastity device.

Monica lifted her toes and rubbed them over Austin's face. He stuck his tongue out to lick up what he could of his precum and she laughed in delight, seemingly at his willingness to be used as little more than a toy for her amusement.

Monica set her foot back in his hands, inched her hips forward until her ass sat at the edge of the couch, and lifted her skirt to her waist. She pulled her delicate panties aside and Austin stared at her plump pussy lips while continuing the foot massage.

Her fingers moved between her legs and moved in slow circles over her pussy lips. Every time her flesh spread open Austin could see the wetness that had formed inside her. He felt his mouth watering at the prospect of getting to taste her and he subtly leaned forward to get just a little closer to her utterly perfect-looking pussy.

Monica plunged three fingers into her well-lubed cunt, closed her eyes, and moaned. She fucked herself as Austin watched from a few feet away. The sounds of slippery penetration filled the air and he moaned as his cock throbbed in its little cage without even a hint of direct stimulation.

"Does Penelope suck his cock, Austin?" Monica asked.

"Yes," he answered. "She said she loves sucking his cock, actually. She said there's something so hot about being on her knees for a man like Colton. She said she loves how turned on he gets, how he moans, and how he wants to fuck her so much harder after she's given him a blowjob."

Monica smiled at him while pumping her pussy with her fingers. "When was the last time she sucked your cock?"

"It's been months," he answered. "Maybe longer."

Monica pulled her fingers from her pussy, leaned forward, and held them up. The smell of her pussy filled Austin's nose as he held her intense gaze and felt his cock throbbing in its little cage.

"You don't really deserve to get your cock sucked, do you?" Monica asked.

"No, I don't," Austin replied.

"Any man who asks to have his dick locked in a cage doesn't really deserve a blowjob, does he?"

He shook his head. He had no argument to counter that assertion. He had asked to be put in chastity, after all. He'd requested that his cock be turned into a small, soft, utterly useless appendage. He'd asked that his wife take control of it, that she step into the dominant role in their marriage, that she put him in the submissive role as a result. Penelope had taken it further than Austin had expected - he'd never imagined her fucking someone else - but he'd asked her to take control and she'd run with it.

"I'd like you to suck the juices off my fingers, Austin," Monica said softly. "Would you do that for me? Would you the sweet, slippery pussy juices off my fingers?"

He nodded and opened his mouth. Monica smiled and pushed all three fingers onto his tongue. He closed his eyes as the taste of her pussy filled his mouth and a moment later Austin had closed his lips around her fingers.

"I wonder if your beautiful wife is on her knees sucking cock right now, Austin," Monica said. "I wonder if she has her lips wrapped around Colton's thick shaft, if she's on her knees in that naughty little lingerie set you dressed her in before she left. I wonder if his hands are in her hair, if he's gently fucking her face while he looks down at her, if he's thinking about how he's going to take your wife to his bed and show her that he's the superior man, that she shouldn't ever let your cock in her pussy again."

Monica began to fuck Austin's mouth with her fingers as she filled his head with wondrous dirty talk. He thought of Penelope on her knees for Colton. He thought of her sucking cock in the strappy bra, panty, garter belt, and stockings set he'd dressed her in. He thought of her looking up at him with lust in her eyes. He thought of how she'd spent the better part of a month giving her body to Colton as often as she could. He thought of the many times Penelope had come home from being with Colton and how utterly satisfied she'd seemed each and every time.

Monica pulled her fingers from Austin's mouth and stood up. She took off her skirt and panties and quickly penetrated her pussy once more, this time with four fingers. He watched from just a few inches away as Monica fucked herself deeply. Then she grabbed a handful of his hair and shoved her fingers into his mouth. She fucked his face, this time with even greater vigor, and she did so while smiling down at him.

"Look at you," she said. "Look at how eager you are to serve me. Look at how happy you are to let me fuck your face while you think about your wife offering her mouth for that same pleasure. You know that she loves giving Colton her body. You know that she's getting more and more into it as the weeks go by."

She pulled her fingers from his mouth and Austin said, "I know. I do. I know that she loves letting him have her, letting him do as he pleases with her, letting him fuck her pussy as many times as he can handle before she comes home to me."

"On your back," Monica instructed.

Austin quickly moved to his back on the living room floor and Monica stepped forward until he was looking up at her wet pussy.

"Should I let you make me cum?" she asked.

"Yes, please," he replied.

"Will you continue to be a good boy for me if I let you cum, Austin? If I give you the gift of tasting my sweet pussy, will you continue to behave?" Monica asked.

He nodded vigorously. "Yes, I will. I'll be good, Monica. I want to make you cum as many times as I can. I'll do whatever it takes to earn the right to serve you. I will."

Monica squatted over his face until her pussy was just a few inches from his mouth. Austin lifted his head to lick her but she swiftly grabbed a handful of his hair and pushed down.

"I didn't give you permission to taste me, Austin," she said.

Monica moved to her knees and scooted back until her pussy rested over his caged cock. She reached down and shoved four fingers into the slippery confines of her body once more. Those fingers then made their way into Austin's mouth. She stretched his lips wide and pushed her flesh deep enough that his gag reflex triggered just a little.

Then Monica sat down on his cock. Her pussy lips spread and she took his caged genitals inside her. Austin moaned as he felt the wetness and intense heat of his cuck sitter's cunt around his long-denied dick.

"Does that feel good?" Monica asked with a smile. She started fucking his mouth as the words left her lips. Her fingers moved in and out, leaving saliva over his lips and chin. Austin couldn't answer, but he nodded as best he could, though his moans made it perfectly clear that he was awash in pleasure.

"We're going to have so much fun tonight, Austin," she said before closing her eyes and moaning. "You'll have the opportunity to make me cum as many times as Colton is going to make your beautiful wife cum. Unlike him, though, you'll have to earn each and every opportunity. You'll have to do anything and everything I want before I'll let you get me off. You'll have to be willing to suffer for me, Austin. You'll have to be willing to give up something to get what you want."

Austin's loins tingled with pleasure. He wasn't going to cum - it was damn near impossible to do so in his cage - but her pussy felt spectacularly good and the addition of her fingers vigorously fucking his mouth delivered an unexpected wealth of arousal.

"Will you do as I desire?" she asked.

He nodded.

Monica moved her hips faster, bathing his caged cock and balls in the juices of her slick pussy. Her fingers moved faster in and out of his mouth and they seemed to go a little deeper with each penetration until he was taking every inch of her flesh. He gagged over and over, but that only seemed to deepen Monica's excitement.

"Fuck...fuck...fuck...I'm cumming!" she cried out.

Monica held her fingers deep in his mouth as she closed her eyes, arched her back, and rolled her head towards the ceiling while her thighs trembled wildly. Austin beamed with pride at having given pleasure to his wife's friend, and at having added another orgasm to his count.

After she'd cum, Monica pulled her fingers from his mouth, wiped them on his chest, and leaned down to offer a soft, surprising kiss while his caged cock remained inside her.

"That was exquisite," she said softly. "And the first of many orgasms you'll give me tonight."

"I'll do anything to make you cum," Austin said.

Monica climbed off his cock, backed up, and instructed, "On your hands and knees."

Austin rolled over onto his hands and knees and Monica grabbed his ass cheeks, gave them a good squeeze, and then ran her fingers over his flesh. She caressed his balls and stroked his caged little cock before running her fingers through the precum leaking from the tip.

"Does Colton fuck your wife from behind?" Monica asked.

"Yes," he answered.

Monica rubbed her slippery, precum-coated finger over Austin's asshole and he instinctively moved his hips forward to escape her touch. Monica put a hand on his lower back and guided him towards her once more. Her finger found his asshole again and she rubbed it in slow, gentle circles.

"Does she like taking his dick doggystyle?" Monica asked.

"Yes," Austin answered. "She said she likes how hard he fucks her from behind, that it seems to unleash an animalistic side of him, that she likes the feeling of being taken by him in a way she's never really felt before."

Monica grabbed Austin's hips with both hands, moved directly behind him, and pulled back as she thrust her hips forward. She did it again and again and again. She was fucking him doggystyle, just without a cock. The more she did it, the harder she dug her fingers into his hips. She managed to thrust with exceptional power, too, and Austin could hear the lust in the way she was breathing. He looked over his shoulder and saw that same lust in her eyes alongside what seemed to be a wealth of aggression.

Monica reached forward and grabbed a handful of his hair. She pulled hard and he arched his back and let his head roll towards the ceiling as she continued to thrust her hips. She smacked his ass a handful of times and Austin yelped from the sharp pain and the surprise of being spanked like that.

Then, Monica released his hair and stopped thrusting. She leaned forward and he felt the soft fabric of her blouse against his bare back before her lips found his neck and offered a handful of hugely erotic kisses.

"It's fun having a toy to play with," she whispered before biting down on his earlobe and pulling hard enough that Austin winced from the sudden surge of pain. "And you're really quite the toy, Austin."

She kissed his neck once more and then stood and put her panties and skirt back on.

"We're going for a drive," Monica informed him. "But first, I want you to retrieve that purple vibrator from your wife's nightstand."

"Can I get dressed?" Austin asked as he stood.

Monica smiled. "No, you may not. Your chastity device is all you need to wear."

Austin briefly considered asking for Monica to share the details of whatever she had planned, but instead he decided to place his trust in his cuck sitter. He retrieved the purple vibrator from the bedroom and returned to Monica, who had her keys in one hand and her purse in the other.

"You can hold on to the toy," she said. "You'll be using it in the car."

Austin smiled at the idea of pleasuring her pussy on their drive and he happily followed Monica towards the door. It wasn't until they were a few steps away that he stopped upon realizing that he'd have to be naked in the driveway.

"I can't go out there like this," he said.

"Yes, you can," Monica replied with a smile. "Don't worry. It's dark out. No one will see that little locked up dick of yours."

She opened the door and stepped out onto the porch. Austin remained in the house as Monica turned back to look at him.

"You could choose to stay in the safety of your house, Austin, but if you do I won't permit you to give me another orgasm," Monica explained. "If you follow me, though, there's a chance I'll let you give me more orgasms than Colton is going to give your wife tonight. There's a chance you might actually catch up and get a great deal closer to earning your release from that lovely little cage of yours. Don't you want that, Austin? Don't you want to set your dick free? Don't you want an orgasm? Don't you want to feel your wife's perfect, wet pussy around your cock again?"

Austin answered by stepping out of the house. Monica smiled, locked the door, and headed to her car with Austin right behind her.

"Actually, come here," she said right as Austin made a move for the passenger side of the car.

He stopped, returned to his cuck sitter, and waited with his hands at his sides as he worried that a neighbor would see him.

"Before we go, I'd like you to kiss my ass," Monica instructed with a smile.

Austin dropped to his knees without hesitation. Monica turned around and he pursed his lips and kissed her ass. She looked over her shoulder at him and lifted the back of her skirt, showing off the wondrous globes of her backside.

"Again," she ordered.

Austin kissed both of her ass cheeks. He did so again and again, losing himself in the unexpected joy of being naked in public and made to kiss a beautiful woman's ass.

"Very good," Monica said as she unlocked the car. "You can get in."

Austin rushed to the passenger door and got in as Monica started the car. She put it in reverse, looked at him, and offered yet another smile, this one with a decidedly naughty feel to it.

"I'd like you to suck on that toy, Austin," Monica instructed. "I'd like you to suck on it like you'd suck a real cock. I know there's very little chance Penelope will ever make you do something like that, but the idea of it turns me on, Austin, so I'd like to see you wrap your lips around your wife's vibrator and suck it like you're trying your very best to give a man pleasure."

Austin had sucked her fingers with such gusto that it seemed like a small leap - if a leap at all - to suck on the toy. He brought it to his lips, wrapped them around the shaft that had offered his wife a great deal of pleasure over the years, and it took it in his mouth.

"You don't have to move it so fast," Monica said as she backed out of the driveway. "That's really only when your man is about to cum. When you first start sucking his cock you want to take your time. Use your mouth to make love to his cock. I promise, that's what Penelope does when she gets on her knees for Colton. In fact, she's confessed that she so thoroughly enjoys blowing him that she likes to spend a fair bit of time on her knees. She likes to start slow, Austin, to tease him, to lure him into that state of desire before he fucks her with such vigor."

Monica reached over and caressed Austin's thigh, moving her fingers in small circles as they approached his caged cock.

"Now close your eyes as you suck that cock for me, Austin," Monica said softly. He closed his eyes and her fingers encircled his dick and caressed his balls. "That's it. Suck like a good boy for me, Austin. Suck that cock to earn a chance to make me cum again. Take it deep, too. Take it nice and deep. Right to the point of gagging."

Austin took the cock deep as Monica teased his dick and balls in an expert fashion. He surged in the cage and he felt the pain of his cock's attempt at growth being so easily defeated. He took the toy deeper, too. He took it as deep as he could go, pulling back right before he gagged and doing so over and over to please Monica and ensure that he'd be given another chance - many more chances, hopefully - at making her cum.

The sucking, teasing, and dirty talk went on until the car came to a stop and Monica instructed Austin to open his eyes. "It's a lovely house, isn't it?"

"It is," Austin answered.

"Would you like to look inside?" Monica asked.

He looked back at his cuck sitter and saw the devilish smile on her face. "Is this Colton's house?"

She nodded. "Do you know what's happening inside, Austin?"

"I do," he said. "Do they know...do they know we're here? Did you let Penelope know we were coming?"

Monica shook her head. "They have no idea. She did tell me there's a beautiful bay window that looks out onto the backyard, though, and I bet that if we went back there we'd have a great view of Colton fucking your wife. Isn't that something you'd like to see, Austin?"

"I...I don't know," he answered. "I really don't know."

Monica squeezed his cock and pulled hard enough to get his attention. "Well, I do know, Austin. I want you to see it. I want you to watch him fuck your wife. I want your little dick to be locked up in this tiny cage while you watch another man fuck your beautiful wife. It would turn me on to see you witness it."

She opened the door, got out, and leaned over to look at him before adding, "And if you refuse to get out of the car, you won't get another chance to make me cum. Now bring the dildo and follow me."

Austin opened the door, took a deep breath, and got out. He quickly looked up and down the sidewalk and then followed Monica through the grass and into the backyard. She stopped at the edge of the house, peered into the yard, and then took Austin's hand and led him to a spot with a great view of the bay window she'd mentioned.

All Austin saw was the back of Colton's head. He was sitting on the couch but from the backyard it looked as though he was alone.

"Is she there?" Austin asked.

Monica ran her fingers down his back and grabbed his ass as she watched next to him. "She's there. She's on her knees for him, Austin. Your wife is sucking his cock. Now put that fucking toy in your mouth and suck just like she is."

Austin lifted the dildo to his mouth and sucked on it. Monica caressed his balls from behind and he felt his cock surge in the tight little cage as he couldn't help but imagine Penelope on her knees in Colton's living room with her head bobbing up and down in his lap.

Then her head appeared. She stood up and leaned forward to kiss Colton. She was naked. His hands moved to her breasts and played with them as they kissed. Austin was stunned at the excitement that coursed through him. It was different than watching the videos Penelope had filmed with Colton. It was hotter. The fact that they were effectively spying probably made it more exciting, too.

Penelope crawled onto the couch and rested her arms over the back. Colton got up and moved behind her. He ran his hands over her ass cheeks and up her back. He grabbed a handful of her hair and pulled back, putting a smile on Penelope's face.

"It's a good view, isn't it?" Monica asked.

Austin nodded as he continued to suck the toy at her instruction. Penelope's mouth opened wide. She was moaning. She had to be moaning.

"He's inside her," Monica whispered. "He's inside your wife's pussy. Look at her, Austin. Look at how much she enjoys having his cock inside her. Look at how good he's making her feel."

Penelope's eyes were closed and her mouth was still open as Colton fucked her. He still had a handful of her hair and he seemed to pull back with every thrust. As far as Austin could tell, she loved getting fucked like that.

"It seems like she likes it doggystyle, Austin," Monica said. "But then, most women like it doggystyle when a man like Colton is fucking us. It's when a man like you is fucking us that we don't really care for being taken from behind."

Monica rubbed his asshole with a finger and Austin couldn't help but moan around the toy he was still sucking on. He wasn't sure why it felt good, but it did.

"Give me the toy," she said.

Austin happily pulled the vibrator from his mouth and offered it to Monica under the assumption that she was going to masturbate while they watched Penelope get fucked. He only hoped that he'd get credit for having given her the orgasm.

She turned the vibrator on at the lowest setting and he watched her hand move towards her pussy. That wasn't her intended destination, though. Instead, Monica moved the toy between Austin's ass cheeks and pressed it against his hole.

"Wait," he said.

"Watch your wife, Austin," she replied. "Watch her take it from behind while I fuck you from behind."

Monica pressed the toy against his asshole and the tip slipped inside him. Austin knew it was far smaller than Colton's cock and he was thankful for that, because the pain was far less than he expected. And, much to his surprise, the vibrations actually felt good.

"That's it," Monica said. "Let me fuck you, Austin. Let me fuck you doggystyle while your wife takes it from behind. Let me pump this tight little asshole of yours while you watch him pump her pussy from behind. Look at how much she likes it. Can you imagine how it sounds in there? Can you imagine how loudly she's moaning as he fills her with his fat dick? You remember how big it was, don't you? You remember seeing it in those videos and pictures she sent. You know he's stretching her out, Austin. You know he's bottom out nice and deep inside your wife."

Austin couldn't resist the pleasure of the moment he was caught up in. He couldn't resist the thrill of watching Penelope fuck another man. He couldn't even resist the growing sensations of satisfaction emanating from his asshole. His cock started dripping precum. His loins tightened and released in the most thrilling manner that made it seem like he was closing in on an orgasm.

Austin started breathing heavier as Monica fucked him faster. He put his hands on his knees to keep his balance and he watched his wife arch her back deeper and roll her head towards the ceiling. He watched her near an orgasm just like he was doing.

"Look at her," Monica said. "She's about to cum with that big dick pounding her tight cunt from behind. Colton's about to add another orgasm to his count, Austin. He's about to make it a little more difficult for you to ever get out of that cage that keeps your cock locked up so tight."

Austin watched Penelope cum. There was no question she was climaxing. He recognized the look on her face. She was cumming with another man's dick inside her and Austin was standing there in the yard with a dildo up his ass courtesy of his cuck sitter.

When Monica pulled the toy out, Austin was disappointed. He wanted to cum with it inside him. He wanted to claim a climax since he hadn't experienced one in nearly a month. He was desperate and it actually felt like the toy might get him there.

"Get on your knees," she said. "You're going to eat my pussy while I watch them fuck."

Austin dropped to his knees and spun around. Monica tossed the toy into the grass, grabbed a handful of his hair, and lifted her skirt before pulling him to her pussy.

"Make me cum, Austin," she instructed. "Do a good job and I'll let you get me off again while we drive home."

Austin would have preferred to watch Penelope get fucked again - and in a different position, no doubt - but going down on his cuck sitter was a lovely alternative and he happily got to business worshiping her pussy and earning himself another orgasm to keep pace with Colton.