<p>“How long has it been?” Jade asked as she caressed and gently squeezed Dean’s balls.</p><p>“Nine days,” he replied.</p><p>“Are you desperate?”</p><p>“Yes,” Dean said.</p><p>Desperate didn’t begin to describe it. His cock had been locked in a metal chastity cage for nine days. He hadn’t been offered any sort of release but he’d been teased relentlessly by his wife.</p><p>“How desperate?” Jade asked.</p><p>Dean felt her breath on his neck as she leaned closer and kissed him. He felt the leather of her boots against his bare skin as he laid on his back in bed and subjected himself to her teasing. It was the only way he stood a chance of being released.</p><p>“I’ll do anything,” Dean said.</p><p>He knew the risks that came with saying something like that. He knew that Jade could ask for something he wouldn’t want to do. He knew that she had a sadistic streak and that she found pleasure in pushing his limits far beyond anything he’d ever imagined.</p><p>Dean watched as Jade moved between his legs. He saw her long dark hair spread around his torso and before she pulled it back. He felt her hands move up and down his thighs. He stared at her breasts, which looked splendid in her tight black corset.</p><p>“You should be careful about claims like that,” Jade said before she took Dean’s locked cock into her mouth.</p><p>She’d gone with a metal cage this time around because she wanted the teasing to be easier. She wanted him to feel it when she blew him while he was locked up and it worked like a charm. It was an experience of pleasure mixed with agony. It was everything he loved about a blowjob without the ability to get hard and truly enjoy it.</p><p>“Please, Jade, I’ll do anything. I swear. I’ll do anything if you’ll just let me out and let me cum.”</p><p>It felt like his body was buzzing with desire. He could feel his thighs trembling as her mouth moved up and down on the locked cock. He could feel his head swimming with desire.</p><p>“Are you absolutely certain?” Jade asked.</p><p>Before Dean could answer she swallowed his locked cock once more. She sucked hard on it and moved her tongue over the flesh that poked through the metal cage. He couldn’t speak. It was an exquisite experience.</p><p>When she finally relented and let his caged cock fall from her mouth, Dean said, “Yes, I’m absolutely certain.”</p><p>Jade played with his balls and looked up at him. A sadistic smile crossed her face. “Do you remember what happened last time?”</p><p>Dean remembered. Last time Jade made him drink her piss before she’d let him out. She made him sit on the shower floor and straddled his face. Over the course of five minutes she unleashed her full bladder into his mouth in short spurts. She demanded that he swallow every drop, but Dean gagged on the last bit because the taste was so strong.</p><p>Jade released him from chastity anyway. She jerked him off in the roomy shower they’d had installed when they renovated their master bathroom. She didn’t give him the orgasm he craved, though. Instead, she ruined it. She masterfully brought him to the edge and then let his cock go. His cum slowly seeped out and he was robbed of the pleasure he sought. Jade laughed as she saw the agony on his face.</p><p>She also collected all the cum in her hand and demanded that he eat it as punishment for not swallowing all her piss. Not only had Dean not gotten the orgasm he wanted but he’d swallowed piss and cum in the span of ten minutes. There was no question it hadn’t gone well.</p><p>“I remember last time,” he said. “I’ll do better this time, I promise. I’ll earn my orgasm. I will. I’ll do anything. I don’t care. Anything you want, I’ll do it.”</p><p>Jade swallowed his locked cock once more. Dean groaned as the agony and pleasure returned. He felt desperate for release and yet he had no idea if Jade was actually going to give him a chance to earn it.</p><p>She released his cock from the grasp of her soft lips and slid off the end of the bed. She looked splendid in her boots, stockings, panties, and black corset. Merely admiring her was enough to make Dean’s dick ache.</p><p>“I’ll be right back. I’m going to prepare your task,” Jade said before flashing her sadistic smile once more.</p><p>She left the room and Dean stared down at his locked cock. It looked like it was trying to burst out of the chastity cage. His flesh was as swollen as it could get in the limited space afforded to it. The longer he stared, the more it ached. He was aroused by the mere sight of his dick in chastity.</p><p>Fifteen minutes after leaving the bedroom, Jade returned with a man in tow. Dean felt a brief moment of joy.</p><p>“Dean, you remember Simon, don’t you?” Jade said as she introduced the tall, fit blonde guy that followed her into the room.</p><p>“Yes,” Dean said.</p><p>Simon smiled and looked at Dean’s locked cock. “If I remember correctly, the last time I saw you I fucked your wife to a loud orgasm while you watched from beneath her, right?”</p><p>Dean nodded. That’s exactly how he knew Simon. He was an occasional bull that Jade brought in when she felt the need for a long, thick cock in her pussy.</p><p>Dean was thrilled. He couldn’t believe that his test was going to be so easy. He loved watching Jade fuck another guy. He loved seeing her moan loudly. He loved seeing her cum so hard with someone else inside her. It was going to be a breeze to do that again. He’d earn his orgasm in no time.</p><p>Dean watched from the bed as his wife kissed Simon. His locked up dick strained against his cage as cuckold-fueled desire surged through his body. Jade was a good kisser and she seemed to be putting extra effort into arousing Simon.</p><p>Jade’s fingers deftly unbuttoned Simon’s shirt and pulled it off as they continued kissing. She ran her hands up and down the other man’s muscular chest and slipped one into his pants. Simon moaned as Dean’s wife found his cock.</p><p>“Fuck, that feels good,” Simon said as he turned to Dean and smiled. His eyes darted to the locked cock. He was clearly feeling a sense of dominant delight.</p><p>Jade fell to her knees and finished undressing Simon. His cock popped free and she licked from the base to the head before taking it in her mouth.</p><p>A sense of warmth and joy spread through Dean. He was finally going to earn his release in a way that wasn’t humiliating or painful. He was going to get to cum after watching his wife fuck someone else and it was going to be beautiful.</p><p>“Do you like watching me suck his cock, baby?” Jade asked.</p><p>Dean nodded vigorously from the bed. “It’s beautiful,” he said.</p><p>Jade’s sadistic smile returned. “Do you want to watch him fuck me?”</p><p>“Yes. Desperately.”</p><p>Jade stood up and moved closer to the bed as Simon followed. She leaned over and grasped Dean’s locked cock.</p><p>“This pathetic little thing can’t give me any pleasure, can it?” she asked.</p><p>“No, it can’t,” Dean happily agreed.</p><p>“Simon’s cock can though. He can fuck me hard. He can pound me with that long, thick, beautiful dick of his. He can make me scream. Is that what you want to watch, baby? Do you want to watch Simon make me scream as he fucks me?” Jade asked as she played with Dean’s balls.</p><p>“Yes. I want to see him give you what you crave,” Dean replied.</p><p>“He’s going to do exactly that,” Jade said before squeezing Dean’s balls hard enough to make him gasp. “Will you do something for me?”</p><p>“Anything,” Dean said.</p><p>“Will you eat my pussy before Dean fucks it? Will you get me nice and wet like a good cuckold is supposed to do for his wife?”</p><p>“Of course,” Dean said. He couldn’t contain his smile. His evening was turning out so much better than he thought it would.</p><p>Jade climbed into the bed and spread her legs. She positioned herself in a way that made it so Dean had to move to his hands and knees to eat her pussy as she desired.</p><p>“That’s a good cuckold,” Jade said as Dean began to worship the space between her legs.</p><p>Just as Jade’s moans began to fill the bedroom, Dean felt Simon’s hand move over his naked ass cheeks. His head popped up as a moment of panic passed through him. </p><p>“Keep eating my pussy, Dean. Don’t worry about that,” Jade said softly.</p><p>Dean went back to work, but Simon’s fingers traced between his ass cheeks and over his asshole. It twitched in response and Dean leaned forward.</p><p>Jade grabbed a handful of his hair and yanked upwards. She looked into his eyes and said, “Are you going to do this again, Dean? Are you going to misbehave and earn yourself another ruined orgasm? Did you really not learn your lesson last time?”</p><p>Dean saw the anger in her eyes and heard it in her voice. He didn’t want to disappoint his wife but he didn’t like that Simon was playing with his asshole.</p><p>“I’m sorry,” he said. “It’s just…he’s touching me back there.”</p><p>Jade laughed and slapped Dean across the face. It was more surprising than painful, but she had his attention. “Simon is going to do whatever he pleases, Dean. He’s the real man in the room. You’re the submissive, locked up cuckold. Now shut the fuck up and eat my pussy.”</p><p>The moment he returned to eating Jade’s pussy, Dean felt Simon’s fingers on his ass again. This time they were wet as they moved between his cheeks and gently rubbed around his asshole. Dean tried his best not to react, though his mind was not focused on what he was doing. It was focused on what was happening behind him.</p><p>As Jade moaned louder Dean was certain he heard the sound of masturbation behind him. It sounded like a hand moving up and down a slick cock. It sounded like Simon was jerking off.</p><p>Simon’s hand pressed on the small of Dean’s back. Moments later Dean felt the head of the other man’s cock against his asshole.</p><p>Despite his desire to please Jade, Dean couldn’t continue licking her pussy when it felt like he was about to get fucked by a man. He ceased eating his wife’s pussy and lifted his head. As he was about to turn around and put an end to his impending violation, Jade sat up and took a tight grip on his hair.</p><p>“Ow, fuck,” Dean said as Jade’s other hand found its way around his neck and applied surprisingly strong pressure.</p><p>Simon’s cock remained at the entrance to his asshole but prodded no further as Jade took complete control over him.</p><p>“Did you really think you were going to earn your release by watching me get fucked?” she hissed.</p><p>“Yes,” Dean said.</p><p>“You stupid fucking cuck.” She released his throat and slapped his face. “You stupid, worthless fucking cuck. You delusional little bitch. Of course that wasn’t going to be how you earned your release. Of course you were going to have to work for it.”</p><p>Jade pulled on his hair and Dean titled his head back in response.</p><p>“Open your mouth,” she demanded.</p><p>He did so and she promptly spit onto his tongue.</p><p>“Tonight, you’re my plaything. You’re my little toy that I get to abuse for my pleasure, and I’ve decided that Simon is going to fuck you for as long and hard as he wants. If you take his cock like a good whore I’ll release you from your cage and give you the orgasm you crave. If you don’t, you’ll stay locked for another month, maybe longer. What do you want?” she asked.</p><p>Her conditions were clear and Dean knew she’d follow through. He’s spend another 30 days in lock up if he didn’t go along with what she wanted.</p><p>“Please,” was all he said at first.</p><p>“You have to make a choice,” Jade said. “I’m not going to make it for you. Either Simon fucks your tight little ass or you stay caged for another month or more. What do you want, you worthless fucking cuckold?”</p><p>Dean took a moment to curse himself for being aroused by his wife’s cruelty. Despite the pain of being choked and having his hair pulled, his cock was throbbing in its cage.</p><p>“I want Simon to fuck me,” he said.</p><p>As soon as the words left his lips Dean screamed in pain as Simon’s cock pushed into his asshole.</p><p>“That’s it, whore,” Jade said. “Take his dick like a good little faggot.”</p><p>It was only a few seconds, but it seemed like it took forever for Simon to bottom out in Dean’s asshole. Every inch was agonizing as he got stretched and filled by the other man.</p><p>“He’s inside you now,” Jade whispered as she maintained her grip on Dean’s hair while rubbing his back with her other hand. “You’re his now. You’re his whore and he’s going to use you.”</p><p>Simon did exactly that. He grabbed Dean’s hips and fucked him. He did so skillfully, too. Everything but the head of his cock departed Dean’s ass before plunging back inside over and over.</p><p>“It hurts,” Dean said as he felt the pain spread through his pelvic area.</p><p>“I know it does. A good whore takes it, though. This isn’t for your pleasure, Dean. This is for his pleasure. This is for my pleasure. You’re working. You’re earning the release you crave so badly. You get fucked and you get an orgasm. That’s how it works. You do what I say and you get treated to something nice. Otherwise, you can spend the rest of your life in that little metal cage.”</p><p>Simon pulled out and Dean heard him spit. He wanted it to be over, but he knew it wasn’t. Instead, the big cock filled his asshole once more. A little extra lubrication made it easier, though. The pain subsided a bit.</p><p>Jade stared into her husband’s eyes and said, “That feels a little better, doesn’t it? You’re starting to enjoy being a fuck hole for another man, aren’t you?”</p><p>Dean didn’t offer an answer. He wouldn’t have said he was enjoying it, though. It was just less painful.</p><p>“Fuck him harder,” Jade demanded. “Use his asshole. It’s yours. Do whatever you want with it.”</p><p>Simon took a tighter grip on Dean’s hips and pulled back as he pushed forward. He fucked the cuckold harder. The pain returned. Dean moaned loudly. There would be no pleasure in this for him. His wife was right. He was a fuck hole being used. In that moment he existed for Simon’s pleasure.</p><p>“You’re doing so good,” Jade said. “You’re being such a good faggot for him.” She laughed.</p><p>Simon began to grunt in a way Dean recognized. He was getting close to cumming.</p><p>“You’re going to take his load in your ass, just like a good whore should,” Jade said. “He’s going to pump you full of cum. It’s going to be leaking out of you all night long.” Again she laughed.</p><p>Simon grunted loudly and buried his cock in Dean’s asshole. He spanked the cuckold’s asshole while cumming inside him. Dean yelped in pain. He felt deeply humiliated as another man painted his rectum with his seed.</p><p>After Simon pulled out, Jade released Dean’s hair and said, “Stay there.”</p><p>He let his head fall to the bed but his ass stayed high. It felt like it was still gaping open after the long, hard fuck he’d received.</p><p>Jade’s fingers found their way to his chastised dick. She slipped a key into the lock and in an instant he was free.</p><p>“You earned this,” Jade said as she began to stroke Dean.</p><p>He turned to look at his wife but she smacked his ass and said, “Look forward. I didn’t give you permission to stare at me.”</p><p>Dean looked forward as Jade jerked him off. She was denying him even while giving him the orgasm she’d promised. Instead of a sweet, sensual handjob with lots of kissing and intimacy she was milking him like he was a farm animal.</p><p>Dean whimpered when Jade released his cock. Moments later her fingers filled his asshole.</p><p>“This would be better with a little bit of lube, right?” she asked. Her fingers pushed deeper inside him. “Simon’s cum seems like the perfect lube, don’t you think faggot?”</p><p>Her fingers were warm and slick as they wrapped around his cock once more. The cum she’d retrieved from his ass felt spectacularly good. It was deeply humiliating to know he was being jerked off with someone else’s semen, but Dean knew that was the point. Jade wasn’t going to let him cum without humiliating him.</p><p>The combined thrills, humiliations, and degradations of the evening finally resulted in an orgasm as Jade stroked Dean’s cock with a firm grip and played with his balls. He grunted and groaned and felt a long, beautiful build-up of lust between his legs before the cum exploded out of him.</p><p>A supernova of pleasure worked its way through his body as his cock twitched and released a steady stream of cumshots.</p><p>Just a few seconds later Jade appeared in front of him. She had a puddle of cum in her hand. His cum.</p><p>“Open up,” she demanded.</p><p>Dean opened his mouth and Jade poured the cum onto his tongue.</p><p>“Swallow, whore,” she said.</p><p>Dean swallowed. His cum tasted salty and bitter, but he took it all.</p><p>Jade moved behind him and slipped his softening cock back into the cage. In just a handful of seconds he was back in prison.</p><p>He’d earned his orgasm, though, and the pleasure of it made everything worth it. Every bit of pain and humiliation was worth getting to experience the bliss of release with his wife’s hand around his cock.</p><p>“Thank you for your services, Simon,” Jade said.</p><p>“My pleasure. I’m happy to do it again whenever you want.”</p><p>“You hear that, cuck? Simon is happy to fuck your faggot ass whenever I want,” Jade said before laughing. “I’m sure he’ll be begging for it before the week is over, so I might require your services sooner than you might think.”</p><p>Dean wondered if he’d really beg for another man’s cock in his ass. Could he be so desperate for an orgasm that he’d actually beg to get fucked?</p><p>He wasn’t so sure his wife was wrong. It had been a great orgasm, after all.</p>