The Cuckold and the Cuckquean Celebrate Halloween

Tucker bent over, plucked an orange cup from the grass, tossed it in the garbage bag he was dragging behind him and marveled at how careless some people could be. Most people, really, at least based on the Halloween party detritus strewn across Theo and Mary's backyard.

A remarkably cold breeze blew through the backyard. The paper pumpkins hanging from the trees swayed and several of the candles that ringed the yard blew out. As the breeze slowed, the yard felt into a state of total silence.

Tucker jumped as he felt Mary's hand on his lower back. She laughed. "Sorry about that."

She too was dragging a garbage bag behind her as they'd been tasked with cleaning while their spouses - Theo and Caitlin - were in the bedroom tending to the desires that had grown over the course of the party.

Tucker turned and looked up at the second floor window into Theo and Mary's bedroom. He'd hoped to catch a glimpse of his wife - perhaps pressed up against the window in her Catwoman costume as Theo took her from behind - but she wasn't there.

"It's hard, isn't it?" Mary asked.

Tucker glanced at her breasts - she was dressed as a particularly sexy version of a pirate and it was hard not to look at her cleavage - and shrugged his shoulders. He wasn't sure why, but he didn't want to admit that sometimes he found it difficult to be a cuckold. She was right, though. It didn't seem fair that he and Mary - who was a cuckquean to her husband - had been tasked with cleaning up the considerable mess left behind by the Halloween party. Tucker would have much rather have been up in the bedroom watching as his wife and her bull had sex, but it was not to be.

Mary took his hand in hers and squeezed it. "Why aren't we closer?" she asked.

"What?"

"Why aren't we closer? Why aren't we better friends? Why does it always seem like you'd rather just hide yourself - your true self - away from me? I mean, we have so much in common. It feels like we should be closer."

She was right. They had a great deal in common. They both found it thrilling to watch their spouse fuck other people. They were both subjected to sexual denial, sometimes for long periods of time. They both got off on the kind of humiliation that was endemic to cucking.

When he didn't answer, Mary dropped her garbage bag, moved behind Tucker, and reached up to rub his shoulders. He too was dressed as a pirate - Caitlin and Theo were delighted by the idea of their cucks wearing what looked like a couple's costume - and he was thankful for the thin shirt he wore as even a few moments of massage washed the tension right out of him.

"I'm sorry," he said. "You're right, of course. We should be a lot closer. It's just...there's something about the idea of you knowing exactly what's going on in my head that makes me...I don't know, anxious. Caitlin knows what turns me on, but she doesn't fully understand it. It's just so different from what turns her on, so of course she can't understand it."

Mary kissed the back of his neck and Tucker felt a shiver of pleasure rush down his spine. They were permitted to indulge in limited physical affection - kisses and groping, mostly - but they rarely did so outside of those times when they were both in the room to watch their spouses fuck. It felt different in the backyard. It felt far more intimate - even a kiss on the neck - and it generated an entirely different kind of sensation that Tucker found quite pleasing.

He turned around and Mary smiled before saying, "You know this part of me - this part of my sexuality - better than anyone in the world. That kind of intimacy...I don't know, I think it just makes me a little bit nervous."

"I understand. Strangely enough, the fact that you know this part of me - this part of my sexuality, as you said - it's the fact that you know that part of me so well that makes me want to be closer to you. I want to share this with someone on a deeper level. I'm not sure that's actually smart, but I can't help but want it."

"Why wouldn't it be smart?"

Mary smiled and caressed his face in a manner that made Tucker weak in the knees for just a moment. "It's a deep kind of intimacy, Tucker. Like you said, we understand each other in a way our spouses don't."

Tucker heard a moan - his wife's moan - and looked up towards the window. He felt Mary grasp his cock through his pirate pants.

"You’re still caged?" she asked.

"I am," he answered. "I've been caged all month, actually. Locktober."

"Have you cum?"

Another moan from the bedroom. Tucker looked up again but Caitlin was probably in the bed and there was no chance of him seeing her from the backyard. He looked down at Mary, who was now teasing his cock through his pants.

"No, I haven't."

"Me neither."

Tucker felt the connection to her. The connection he'd been resisting. The connection that was perfectly natural between two people who found pleasure in indulging in the same kink.

"Does he tease you?" he asked.

Mary nodded. "Every day. He makes me edge. Sometimes he does it while telling me about how much better your wife's pussy is. Sometimes he uses the head of his cock to edge my pussy by rubbing it all around my labia - and my clit - but denying me the pleasure of having him inside me. Sometimes he fucks my mouth nice and slow while telling me that your wife sucks his cock better than I ever have."

She kissed Tucker's neck and he moaned before reaching down and gathering the bottom of Mary's skirt. He pulled it up and rubbed his fingers over her panties. She was wet - soaked, really - and she moaned against his neck.

"Caitlin teases me too," he confessed. "She likes to make me strip and then she sits on my cock. She takes me inside her and rubs her wet pussy all over me. She tells me that my cock doesn't deserve to be unlocked and that it doesn't deserve to be inside her. She tells me that your husband fucks her far better than I ever have, that she might leave my cock in chastity forever because it's basically useless to her."

Mary stepped back. "Sorry," she said. "You almost made me cum and Theo wouldn't like that."

Tucker smiled. "Sorry about that."

She picked up her garbage bag and started collecting trash once more. "It's okay. I like getting close. I like being edged. I like being denied. I can't imagine anyone else would understand why I'd enjoy that, but I bet you do."

Tucker nodded as he too resumed cleaning up while his wife moaned with another man's cock in her pussy. "I do. It was experimenting with denial that got us started on this, actually."

"Yeah?"

"I can still remember the conversation. We'd just finished having sex but I hadn't cum because Caitlin got there so fast. She'd been on top and she climbed off and took my cock in her hand. She kissed my neck and asked if I wanted her to make me cum. She was asking in that sexy kind of way that's meant to be a turn on as she assumed that of course I'd want to cum."

"Did you tell her you didn't want to?"

He nodded. "Yeah. She didn't understand it. I couldn't really explain it, either, because I actually didn't understand it. I just told her that I was turned on by the idea of not being allowed to cum. We talked about it a little and the night ended with her sitting on my face and riding my tongue to a second orgasm. It was a huge turn on."

"I can imagine," Mary said as she collected the pieces of a carved pumpkin that someone had seen fit to smash. "We got started at a Halloween party."

"Really? Do tell."

She shot him a smile and Tucker felt a surge of desire for her.

"This was almost a decade ago. Back when we lived in the city. We went to a huge party at a warehouse. Theo was dressed as Roman soldier - he'd just read a Julius Caesar biography and was obsessed - and he honestly looked really, really hot. At one point I left to go to the bathroom and when I came back I saw him flirting with a blonde woman in a slutty vampire costume. She was actually flirting really hard - lots of touching him and that sort of stuff - and I felt this instant sense of arousal. It was like my whole body had been flooded with it. I'd never felt anything like it."

"What did you do?"

"I watched," she said before bending over to pick up a beer can and offering a remarkable view of her breasts that Tucker gladly soaked in. "I watched them flirt for a few minutes and then Theo saw me. He looked embarrassed for a split second - like he'd been caught doing something naughty - and then he saw that I was turned on. At least that's what he said afterwards. So he kept on flirting. When she touched him he didn't pull away. When she leaned in to kiss his neck - or kind of bite it, as she was a vampire - he looked at me and he made this face like her kiss was the most incredible thing. I can still remember how wet my pussy got, how I had this tingling feeling between my legs, this feeling of overwhelming desire."

Tucker couldn't help but feel a touch of arousal at Mary's story. He'd been in that same position countless times with Caitlin and it always proved hugely arousing. "What happened next?" he asked as Mary dropped to her knees to collect yet another smashed pumpkin.

She tossed the pumpkin pieces in the trash bag, wiped her hands on the grass, and then sat back on her knees and smiled at him. "We went home and he fucked me while we talked about him fucking the vampire girl. It was so hot. The sex was so good that I was hooked. Things have evolved over the past decade and it's really been the most remarkable journey."

"Sorry I haven't made an effort to get to know you better," Tucker said. "You're right that we should really be much better friends given that we have this really specific thing in common."

Mary lifted her hand and beckoned him closer. Tucker dragged the garbage bag behind him as he approached. He stopped a few yards short of her - she was still on her knees - but she urged him to come close enough for her to reach up and play with his cock.

"When was the last time a woman was on her knees for you?" she asked.

Tucker's cock ached in the cage. Even the smallest touch was enough to drive him crazy with desire after more than thirty days in the steel prison. "The last time was when Caitlin had gotten on her knees to do a cock comparison between me and a bull."

Mary smiled. "And when's the last time your wife got on her knees to suck your inadequate cock?"

Tucker's legs trembled for a moment and then Mary reached up and loosened the rope belt that kept his pirate britches up. His pants fell to the grass the moment the rope came untied. She teased him through his underwear as he answered, "She hasn't given me a blowjob from her knees since she first cuckolded me. So...seven years, I think."

Mary pulled his underwear down and leaned in to kiss his thighs. Her lips made their way to the cage and he felt their warmth and softness against the bits of flesh that poked through the tight cage.

"Theo almost never fucks me. He says my pussy isn't worthy of his cock. He says that your wife's pussy makes him cum so much harder. I get so fucking wet when he talks to me like that."

She took his caged cock in her mouth and Tucker groaned at the mixture of pain and pleasure that burst from his loins.

"Does that feel good?" she asked while teasing his balls with her delicate fingers.

"Yes. It hurts too, though."

"That's how it goes for a cuck, isn't it?"

Tucker smiled and nodded. "It is."

Mary took him in her mouth once more. He could feel her sucking on his caged cock and it served as a painful reminder of just how good a blowjob felt, except without any of the actual pleasure of getting his dick sucked.

Then it was over. She stood and kissed him. She did so with surprising depth and passion while caressing his balls and teasing his caged cock. She almost certainly knew that her kiss would make him suffer, and it did. The pain between his legs was incredible, but there was such intense pleasure with it.

As she stepped back from the kiss, Mary glanced up at the window. Tucker turned his head to see Caitlin smiling down at both of them. To his surprise, she was still dressed in her Catwoman costume, though he knew it featured a very well-placed zipper that would allow Theo access to her pussy. It was technically meant to make going to the bathroom easier, but Caitlin had purchased that particular costume so she could get fucked in it.

Caitlin gestured for Tucker to turn around and he did so. Mary then stepped next to him and took his caged cock in her hand. Caitlin smiled from the bedroom window as she watched another woman tease his cock.

Mary kissed him on the cheek and Caitlin gestured for them both to come upstairs. "It looks like we're needed," she said. "You should put your pants back on."

Tucker hastily got dressed as Mary collected a bit more trash. She led the way inside and he followed. They headed straight for the master bedroom and found Theo naked in the bed. Caitlin stood in the same spot by the window, only she'd turned around and Tucker could see his wife's pussy and admire the puffy pink lips indicating that she'd already fucked her bull once.

"It's fun teasing his pathetic little cock, isn't it?" Caitlin asked.

Mary nodded as she tucked her hands behind her back.

Caitlin stepped away from the window and approached her bull's cuckquean. She reached up and slipped her fingers into Mary's mouth. She pushed them deep. Those fingers then moved under Mary's dress and - judging by the look on her face, at least - they quickly moved inside her.

"What made you wetter? Teasing my husband's little dick or knowing that your husband was up here fucking a far sexier woman than you?"

"Knowing that my husband was fucking you...that your pussy was satisfying him...that he was satisfying you instead of me."

"Because you don't deserve the satisfaction his cock can provide, do you?" Caitlin asked.

Mary shook her head and moaned. Tucker could hear the sounds of fingering, making it seem like she'd gotten even wetter.

Caitlin then looked at Tucker. "And you don't deserve the pleasure of my pussy, do you cuck?"

"No," he said. "I'm not capable of satisfying you like Theo is, so I don't deserve to fuck you. I don't deserve to come anywhere near your pussy and anytime you let me inside you it's a gift that I cherish."

Caitlin pulled her fingers from Mary's pussy and stepped towards her husband. She pushed them into his mouth and he tasted his neighbor's sweet juices. "Did it feel good to have her pretty little mouth around your worthless cock?"

He nodded.

"Her husband instructed her to tease you. Did she do a good job?"

Tucker nodded vigorously.

"On your knees, darling," Theo instructed.

Tucker watched Mary fall to her knees and look up at her husband, who'd gotten out of bed and was standing in front of his lovely submissive wife.

"How did it feel to suck on the cuck's pathetic little dick?"

"It felt good to do as you instructed. It felt good to tease him, too. I could see that he liked it. I could see that it caused him a bit of pain, too. I liked knowing that I was doing as both of you desired, though."

Mary glanced at Theo's cock and he smiled. "Would you like to suck my dick?"

"Yes, please," she said.

Caitlin pulled her fingers from Tucker's mouth and stepped back. Theo then slid over until he was standing in front of him.

"Why are you still standing, cuck?" Caitlin asked.

Tucker fell to his knees and stared at the cock that was now just a few inches from his mouth.

"Will it make you jealous if my cuck sucks your husband's glorious, perfect cock?"

"Yes," Mary answered. "Please, let me suck it. Let me pleasure you, Theo. Let me use my mouth to make you feel good."

Theo laughed, took his cock in his hand, and guided it to Tucker's mouth. "Suck on it, faggot," he instructed.

Humiliation coursed through Tucker's body as he parted his lips and took the dick into his mouth. He tasted his wife's pussy on the soft head and the increasingly erect shaft. He wondered if Theo had cum, if Caitlin's pussy was brimming with another man's load.

"Don't worry your pretty little head," Caitlin said, "there's something for you to do. After all, my pussy is filled with your husband's cum."

Tucker felt the same jealousy he knew Mary was experiencing. It was humiliating, but he liked cleaning cum from his wife's pussy. It turned him on. It made his cock throb in the cage.

"Does he cum in your pussy, Mary?"

"No," she answered. "When he does fuck me, he uses a condom."

Caitlin laughed softly. "Of course he does. Your pussy isn't worth of his cum. You're not worthy of giving him the ultimate pleasure, the thing every man wants. You're not worthy of taking his load in your worthless cunt."

Mary moaned and Tucker couldn't help but do the same. Theo and Caitlin had developed a skillful back and forth in the year they'd been cucking their spouses together and it proved wildly arousing for all four members of their naughty little group.

"Now worship the cunt that your husband prefers over yours. Worship the cunt that he seeded and lick his load out of me."

Tucker heard the sound of pussy worship and jealousy coursed through him. He wanted to be eating his wife's messy cunt. He wanted to be cleaning her. Instead, his mouth was stuffed with a fat cock. His jaw ached. His eyes were watering.

Both cucks in the room did their duty until their respective spouses were satisfied. Tucker's chin was coated in saliva and his mouth tasted of cock and pussy. His dick throbbed, though, as it always did when he was subjected to any form of cuckold humiliation.

"Get naked and get on your back, Tucker," Caitlin instructed.

He did so as everyone in the room watched. Tucker couldn't help but feel inferior to Theo, who was larger and far more muscular than him. He got on his back and when Theo stepped closer Tucker thought he might soon be covered in a shower of cum.

Instead, Caitlin turned to Mary and said, "Take off your panties, hike up your dress, and ride his worthless dicklet. Edge yourself with it. Be a good little slut and edge yourself silly."

Mary removed her panties, pulled up her dress, straddled Tucker's crotch and settled onto it. He felt his caged cock slide into her wetness and groaned immediately. She rested her hands on his chest, smiled, and began to move back and forth over his imprisoned, small, soft dicklet.

"That feels so good," Mary said.

Caitlin laughed. "That's not something I've said all that often with my husband's dick inside me."

Theo moved behind Caitlin and grasped her breasts through the faux leather of her catsuit. She turned her head to kiss his neck and reached back to stroke his cock. Tucker watched while his caged dick was bathed in the heat and wetness of Mary's pussy.

"Do you want me?" Caitlin asked.

"I do. I always do. You make me feel better than any woman ever has, Caitlin. You make me cum harder than I've ever cum in my life, even after a year of fucking you. I can't believe how hot it still is."

They kissed and Mary looked back. She and Tucker watched the tongues of their spouses entwine. They watched Theo's hand slip inside Caitlin's catsuit to play with her tits. Mary's legs began to tremble, so much so that she had to lift her pussy to prevent an orgasm.

"Look at your little cuck," Caitlin said as she turned back to them. "I think she almost came watching us kiss."

"I think it turns her on to know that you make me cum harder than she ever has," Theo said. "I think she likes knowing that she's the inferior woman in the room, that even if she tried her hardest she couldn't come anywhere near making me feel as good as you do."

Mary sat down on Tucker's cock once more and began to ride him as slowly as possible.

"You feel the same way, don't you cuck?" Caitlin asked as she looked at her husband. "You love that you're nothing compared to Theo, that you couldn't fuck me to the kind of orgasm he gives me if I gave you a hundred chances."

Tucker nodded and his cock throbbed in the cage.

"Mary, my sweet little cuck slut, if you could choose between sucking my cock or cumming while you ride Tucker's little cage, which would you choose?"

"I'd suck your cock," she answered.

Theo smiled and stood astride Tucker's body while facing his wife. He stroked his dick in front of her mouth as she continued to grind on Tucker's little locked up dicklet.

"Keep riding him," Theo said. "Don't stop while my dick is in your mouth. If you stop or you cum, there will be a punishment. Do you understand?"

Mary looked up at him and nodded.

Theo slipped his cock into his wife's mouth, grabbed her head with both hands, and began to slowly fuck her face. Tucker had enjoyed a similar view of his wife giving a blowjob many years ago and that memory - and the sight of his fellow cuck sucking dick - brought with it a wealth of arousal.

It wasn't long before Mary was moaning with great vigor around the dick in her mouth. Saliva spilled out and dripped onto Tucker's stomach. She rode him slowly, but it seemed that she was on her way to an orgasm. The only question was whether or not Theo would pull out of her mouth before she came and secured a punishment for herself.

Theo didn't pull out. He slowly fucked Mary's mouth until she climaxed. Her whole body shook and Tucker experienced a wealth of arousal, a bit of jealousy, and more than a little sympathy for the fact that she was about to be punished.

"I'm sorry," Mary said as Theo pulled out and rubbed his spit-soaked dick all over her face.

"It's okay," he replied. "There must be a punishment, though."

"I know."

Theo took a step back and promptly sat on Tucker's face. His hairy ass cheeks spread and his asshole landed right on Tucker’s mouth. He tried to roll away but Theo was damn near smothering Tucker's face, making it impossible to fully escape the reality he found himself in.

"I didn't say you'd be the one to get punished," Theo said to his wife.

"Eat his ass, cuck," Caitlin chimed in. "Suffer the punishment for Mary's weakness. Lick his asshole. Tongue fuck it. Be a good cuck."

Tucker was awash in arousal, disgust, and humiliation. He was being pulled in all directions. Then Mary began to grind on his cock once more. She lured him away from the disgust. She filled his body with pleasure.

He put his tongue to work. He ate a man's asshole for the first time in his life. He licked it. He lapped at it. He pushed against it. He wasn't sure he'd ever felt so humiliated - the facesitting made it so much worse - and he was absolutely certain he'd never felt so powerless. He did it, though, and there was something oddly freeing about completely surrendering to the punishment.

Eventually, Theo stood up and Tucker saw his wife smiling down at him. She held his gaze for a few seconds and then looked at Mary and said, "How would it feel if I made you suck my husband's cock until he came in your mouth?"

"Humiliating," Mary answered.

"Why?"

She glanced at him and then looked back to Caitlin. "Because...because he's an inferior man. He's not worthy of a blowjob. To be made to suck him off while being denied the opportunity to suck off my husband...it would be deeply humiliating."

Tucker believed her. He was a cuck. Of course Mary would have preferred to give her husband a blowjob to completion. Of course she would find it humiliating to be made to suck the dick of a man who'd spent an entire month in chastity because he was unable to satisfy his wife's sexual needs.

Caitlin walked towards the nightstand and returned with the key to Tucker's chastity cage. She then dropped to her knees and unlocked him.

"Suck him off, whore," Caitlin demanded.

Mary went to work right away. She might have found it humiliating, but she wasn't going to disobey. She'd been a cuckquean for nearly a decade and she was very well-trained.

It was the first blowjob Tucker had received in years and it felt spectacular. Beyond spectacular, in fact. He was hard in a matter of seconds and on the verge of an orgasm not long after.

"Fuck!" he cried out right before cumming in her mouth.

"Don't swallow," Theo instructed.

Tucker's mind went blank as he came and pleasure enveloped him. A month without an orgasm meant that the pleasure of it was overwhelming in the best way possible.

"Now feed him his load," Theo said.

Tucker saw his wife stroking her bull's cock as Mary crawled on top of him. He knew that Caitlin and Theo were engaging in foreplay by humiliating their cucks. It brought him a wealth of pleasure to know that he'd helped turn them on.

Tucker opened his mouth as Mary hovered above him. She pursed her lips and a moment later his cum slowly poured out. She transferred every drop of it to him and smiled.

"Now kiss him," Caitlin said.

Mary leaned down, closed her eyes, and kissed him deeply. Their tongues swirled in the cum and soon it coated the entirety of Tucker's mouth and likely did the same with Mary.

"Now swallow," Theo instructed.

They both swallowed and Mary kissed him on the cheek before sitting up.

"There's quite a bit more cleaning to be done," Caitlin said. "You may leave and get started on that while we fuck."

Tucker was disappointed that they wouldn't be allowed to watch, but he wasn't surprised. He and Mary were tools to be used for the pleasure of their spouses and they'd served their purpose and could now be put to work cleaning up the mess of the party.

They got up, got dressed, and left the bedroom right as Caitlin crawled into the bed and looked back at Theo, who followed her into the bed and guided his cock into her pussy from behind.

Tucker wanted to watch, but he was a good cuck and he was going to follow orders. There was enough mess that it would probably take a few hours to clean up and with any luck he and Mary would be called back to the bedroom to have a little more fun before the night was over.