The Journey of a Submissive Cuckold - Part 10

Click here to read the previous parts of the story.

For a dominant woman there's often great pleasure in a man's willingness to push his sexual boundaries for her pleasure. Annalise is that kind of domme and she finds herself intensely aroused by your willingness to give yourself over to her in the name of feeding your submissive side. It's made all the more arousing because you know that your wife is across the country having sex with her boyfriend as you're giving up your manhood for Annalise's pleasure.

---

"Are you nervous?" Annalise asked as you walked through the doors and into the sex club's locker room.

"Yes."

It wasn't being at the club that made you nervous, though. You'd been numerous times with Annalise. You'd witnessed countless pleasures and experienced more than a few of your own.

"Strip," she instructed.

You removed your clothes, doing so a little slower than usual because of the nerves you felt. Annalise must have noticed as she stepped closer, kissed your neck, and moaned softly.

"It's okay to be nervous," she whispered, her breath tickling your neck. "Just remember that you're doing this for me. Remember that tonight, in this club, you exist for my pleasure. You will do as you're told for my pleasure."

Her hand slipped into your underwear and she caressed your freshly shaved balls and caged cock. She moaned like a woman already lost in the pursuit of an orgasm and her lips found their way to yours. The kiss was slow at first, but soon Annalise's tongue was deep in your mouth and any nervousness had washed away in favor of letting your body be enveloped in arousal.

You removed the rest of your clothes and stood there naked with your cock in a cage and a plug stretching your ass. Annalise turned around and gestured to her zipper. You tugged on it and helped her out of her dress, revealing a black basque with lace detailing that made her look both elegant and sexy. It looked exquisite paired with her thigh high leather boots and you felt an urge to drop to your knees and worship right there in the locker room.

"You look incredible, Annalise," you said.

"Why thank you," she replied with a smile. "Lindsay is especially fond of this look and if I'm being honest, I wore it because I want to entice her. I want to inspire that desire she sometimes feels where she tries to conquer by fucking me hard with her strapon. Who knows, perhaps I'll even inspire her to unleash her inner domme and surprise me with something naughty."

You'd watched Annalise submit to Lindsay's strapon before. You'd watched as your domme offered her pussy to her kinky friend. You'd listened as Lindsay directed cuckold dirty talk towards you, telling you that you could never hope to fuck Annalise the way she does, that even if your domme allowed your worthless dick inside her that you'd never be able to satisfy her. Your cock had throbbed in its cage each time you'd witnessed their encounters and you hoped you'd get to witness such pleasures that night at the club.

Annalise reached into her bag and pulled out a leather collar with a metal loop where someone might attach a leash. "I got you something," she said. "Something to make clear to everyone else that you're owned, that you belong to someone, that you belong to me."

She held it up. There was a metal tag hanging from the hoop. It read "Property of Annalise." You smiled and your loins tingled.

Annalise placed the collar around your neck and stepped behind you to lock it. She then pulled a leash from her bag and attached it to the metal hoop. Her fingers grasped the end of the leash tightly and she tugged on it. You lurched forward and a smile of pure joy spread across her face.

"Above all else, you must remember that you belong to me," she said softly. "You're my property when you're with me. You do as you're told and you trust in me to look out for your well-being as I push your submissive boundaries."

"I do trust you," you replied.

Annalise rewarded you with a kiss while she kept a tight grip on the leash. You felt the warmth of the leather collar against your neck. You felt the kinky thrill of being on a leash, of being caged, of being plugged, of being owned by a woman for the night.

"Your wife texted me right before we arrived," she said. "She sent a selfie of her in the lingerie she's wearing for her boyfriend."

Your wife now referred to him as her boyfriend instead of her lover. It spoke to the deepening of their relationship, though they still spent a great deal of time fucking when they were together.

"She sent it to me so that I could let you see it as a reward," Annalise explained. "You would like to see your wife in the lingerie she bought for another man, wouldn't you?"

You nodded and Annalise moved to your side and ran her fingers between your ass cheeks. She gripped the plug inside you and pulled it out just a little, stretching your asshole and eliciting a groan.

"She sent that picture ten minutes ago. His cock is almost certainly inside her already. Do you think she's giving him a blowjob? Do you think your beautiful wife is on her knees in front of the man that satisfies her? Do you think her head is bobbing up and down in his lap as she pleasures him in a manner she no longer pleasures you?"

"Yes," you admitted. "She loves sucking his cock. She loves pleasuring him like that."

Annalise pulled the butt plug all the way out and slowly pushed it back inside you, penetrating and stretching your asshole and drawing your thoughts to what was almost certainly going to unfold that night in the club.

"Why does she love pleasuring him like that?" she asked.

"Because he fucks her better than I do, than I ever have. He fucks her better than any man ever has."

Annalise moaned. "So she gives him anything he wants. She pleasures him in the manner he craves. She tends to his needs in a manner she's never done for her cuck husband."

"Yes, and it's what he deserves."

Annalise pushed the toy deep in your ass, stepped in front of you, and smiled. "Your wife knows what I intend on doing with you tonight. She approves. She thinks it will be good for you. She struggles to dominate you at home, but she said that you're a better husband since I met you, since I started dominating you. I think she might find her way towards taking a more dominant attitude at home if you continue to play the part of a submissive husband. Doing chores. Tending to her needs. Making sure her life is as easy and joyful as it can be."

"You really think so?"

Annalise nodded. "I can't say for sure, of course, but I think she'd coming around to the notion that there's a way to blend fetish and real life and have it benefit all parties involved. She won't be strapon fucking you over the kitchen table, but she might be willing to treat you more like a submissive on a day-to-day basis and give you something of what you crave more regularly."

"I'd love that."

She stepped closer and kissed you on the cheek. "Then keep being the kind of husband she needs. Keep offering your submission in small ways. Keep supporting her. Keep doing as much of the housework as you can handle. Show her the kind of husband you'd be if she dominated you and she might be willing to take charge in a manner you would find enthralling."

"I will. I will."

Annalise stepped back, grabbed the leash, pulled it tight, and walked you out of the locker room and into the club, kicking off a night of boundary-pushing pleasure for the both of you.

---

Annalise led you through the club by the leash and you drew countless stares, though you were hardly the only leashed submissive. You might have felt self-conscious on your first visit to the club, but that sensation had disappeared over numerous visits. Now you enjoyed being a good submissive for Annalise. You enjoyed the lusty looks that were occasionally directed your way. It made you feel like you were a good submissive, like other people wanted to possess you.

"We're going to the top floor tonight," Annalise said as you stepped into the elevator.

The top floor was reserved - somewhat informally - for the kinkiest members or those engaging in extended penetrative sex acts like the ones you expected you'd be subjected to that night.

The elevators doors opened and you stepped into a dimly lit hallway behind Annalise. She stopped, jerked the leash until you stepped closer, and then pointed to the floor.

"On your knees. Lick my boots."

You fell to your knees and leaned forward. You kissed and licked her boots. The leather felt warm and a bit rough against your tongue.

"Look at him," someone said. "You've trained your pet well."

"I have," Annalise purred. "In more ways than one."

A delighted laugh rang out and you heard high heels clicking as someone walked down the hallway. Annalise pulled on the leash and you sat back on your knees and looked up at her.

"You will crawl next to me like a good pet," she instructed.

You nodded and she walked slowly down the hallway. You crawled next to her. It hurt your knees, but you'd long since learned that a submissive must sometimes surrender to pain for the benefit of his domme.

Annalise stopped in front of an open door and you sat back on your knees next to her and peered inside. A woman in lingerie was on her hands and knees in a twin bed with shiny black latex sheets covering it. She had a cock in her mouth and another in her pussy. She was moaning loudly as the two men fucked her in rhythm, the one taking her from behind delivering hard swats to her ass, which was already reddened.

"She's tight," the man in her pussy said.

"She is. Don't worry, though. We'll stretch her out before the night is over. We'll stretch her ass, too."

The woman moaned. The man in her mouth pulled out and rubbed his spit-soaked cock all over her face. The he moved back, bent over, and shoved three fingers in her mouth, pushing them deep enough that she spit up and drooled onto the bed.

"You're giving us all three holes tonight, aren't you?" he asked.

"Yes, sir. My body is yours."

She moaned as he slipped his fingers back into her mouth. More drool fell to the bed. He pulled his fingers free and pushed her head to the mattress.

"Clean up your mess."

She licked up her saliva as the man in her pussy fucked her harder and spanked her ass.

"Can I cum, sir?" she asked.

You marveled at her arousal, at her eagerness to be pushed so far into submission that she could climax - or get close - from the sheer pleasure of being treated like a fuck toy.

"No, you may not," he replied. "If you do, we'll take turns belting your ass until it's bruised."

She moaned and her thighs began to tremble. It seemed that she was going to cum, that the threat of being belted was going to put her over the top. You smiled as the sheer kinky pleasure of the scene washed over you.

"Come," Annalise said.

She tugged the leash and you fell to your hands and knees once more and crawled next to her. You heard the woman cry out in pleasure. She was cumming. She would be belted. She would suffer. That was part of the plan, though. Of course it was. She had her pleasure. She would suffer for theirs. That was their dynamic and you suspected it would play out all night long until exhaustion overtook them.

Annalise stopped and you looked up to see Lindsay standing just a few yards away. She stared at your domme, her eyes wandering over Annalise's lithe, lingerie-clad body.

Lindsay then looked at you, smiled, and said, "You look good on a leash."

"Thank you."

She gestured to her left and stepped into the room. Annalise led you inside and Lindsay pulled her close for a kiss. You looked up to see their tongues entwined as Lindsay’s hands grasped two handfuls of your domme's ass and squeezed hard.

It wasn’t until the kiss was over that you noticed two men in the room.

"Jake, Dallas," Annalise said. "It's good to see you."

You'd met them months at during your first visit to the club. Jake was a dom and Dallas his sub. It was Jake that had introduced Annalise to the idea of chastity, so you had him to thank for your cock's locked up status.

Jake was dressed in a pair of tight latex shorts that outlined the bulge of his cock and balls. Dallas was naked, though like you he wore a chastity cage.

"Thank you for your willingness to join us, Jake," Annalise said before they shared a brief embrace.

"Oh, believe me, it's my pleasure."

They both looked at you and your pulse quickened as the nerves you'd felt in the locker room returned.

"He looks scared," Jake said.

"I think he is. He's known this was coming, but despite his submissive nature, this is not something that comes naturally to him," your domme replied.

Jake moved towards you. He stopped a foot away and grasped his bulge through the latex shorts, which appeared to be rather thin and flexible now that you were close enough to study them.

"It's okay to be scared, to be nervous, to be downright terrified. You're about to do something that most straight, married men would never do. You're not like most straight, married men though, are you?"

You shook your head as Annalise appeared next to Jake. She held up her phone - she'd tucked it into what must have been a pocket in her basque - and you heard the distinct sounds of sex emanating from the speaker.

"That's his wife," she said. "And that's very obviously not him."

Jake smiled as you listened to your wife getting fucked.

"She just sent this. She wanted him to know what she's doing while he's here sucking cock for my pleasure," Annalise continued. "As you can see, she's having a damn good time."

Jake put a hand on the back of your head and stepped closer until the bulge of his cock was pressed against your lips. The latex felt warm and smooth and the smell was surprisingly alluring.

"Suck on it," Annalise instructed. "Mouth it through his shorts. Show affection for the cock that's going to fill your throat."

You opened your mouth and showed affection, as Annalise had put it. You licked. You sucked. You mouthed his cock through the smooth, slippery, shiny latex shorts. You felt him grow inside them and experienced a wave of angst and another of excitement at the idea that your mouth had provided him with pleasure.

All the while, Jake, Annalise, and Lindsay watched your wife get fucked in what sounded like doggystyle, at least paced on the pace and the sounds of flesh meeting flesh.

"She takes cock better than most," Lindsay noted.

"His cock makes her feel things that her husband has never made her feel," Annalise replied. "That's why she's with that gorgeous man. That's why she's on her hands and knees for him. That's why she'd moaning so loudly. She's reached a place with him where merely pleasuring his cock brings her close to orgasm, and a good hard fucking is more than enough to put her over the top."

Jake looked down at you, grabbed a handful of your hair, and rubbed his latex-clad cock over your face, spreading saliva over your cheeks, forehead, and chin and smiling as he did so.

"You'd like to watch that video, wouldn't you cuck?" he asked.

"Yes," you replied.

"He's not allowed to watch until he pleases me," Annalise chimed in. "And he's going to have to please you - and perhaps Dallas, if you allow it - before I'll even consider letting him watch the video of his wife cumming with someone else's cock inside her."

Annalise tucked her phone away and lowered Jake's latex shorts. His cock popped free and slapped your chin before brushing against your lips, which remained closed.

"Dallas, darling, come here," Jake said.

The caged submissive approached and Jake pulled off the necklace holding the key. He handed it to Dallas and nodded for the young submissive to unlock his caged cock.

"Has he sucked cock before?" Jake asked.

"No," Annalise answered. "Strapons. Fingers. Dildos. He's practiced plenty so he should be ready to pleasure you, but yours will be his first real cock."

Lindsay kissed your domme's neck, eliciting a soft moan as Jake rubbed his cock over your lips.

"Your domme wants to watch us use you," Jake said. "In fact, I'm certain that she's going to have multiple orgasms watching you get used by two gay men."

"I know," you replied. "I want to make her cum like that. I want to serve her like that."

"Then open your fucking mouth."

You opened your mouth and Jake's cock passed your lips. Annalise moaned as Lindsay rubbed her pussy and kissed her neck.

"Suck his cock," Annalise said. "Suck both their cocks. Let them fuck you if they desire it. Let them use you to cum."

You sucked cock as Jake maintained his grip on your hair. Lust washed over his face and he began to gently thrust his hips, moving his dick in and out of your mouth at a slow pace. You sucked. You swirled your tongue around his dick. You kept your teeth out of the way, too, remembering the many lessons Annalise and Lindsay had given you while making you practice with dildos.

"Fuck his mouth," Jake said to his sub.

You turned your head and Dallas's cock - which was actually bigger than Jake's - entered your mouth. He fucked your face more aggressively than his dom, perhaps owing to the fact that he'd been locked up for quite some time. You drooled. Your jaw ached. Your eyes watered. You gagged a little. Dallas was lost in his pleasure, though, and you heard Annalise moaning wildly, which was the thing that made your dick throb in its cage.

You blew them both from your knees, pleasuring one man and then the other. Jake had hold of your leash, Annalise having given it to him so she could sit and watch while occasionally kissing Lindsay, who also seemed quite enthralled with the sight of a straight man sucking two cocks.

You sucked balls, too, because that's what a good cocksucker does and you wanted nothing more than to be a good cocksucker in the moment.

"Eat his ass," Jake instructed right before Dallas turned around, bent over, and spread his cheeks.

You hesitated. You looked towards Annalise.

"Don't disappoint me," she said. "Your job is to pleasure them. You know that. Do your job. Eat his ass so I can get off to your willingness to do anything to please me."

You turned back to Dallas's ass. You leaned in. You licked his asshole. You bathed in the utter humiliation of pleasuring a man in that way. Jake put a hand on the back of your head and pushed, smothering you in his sub's ass. Your tongue went wild and Dallas moaned.

"Oh, fuck, I'm cumming!" Annalise cried out. Her moans went on for quite some time. You were fairly certain you heard her wet pussy being played with, too. You felt joy at her orgasm, for on that night it was akin to a climax of your own.

Dallas stood up and turned around. He guided his cock between your lips and fucked your face as Jake kissed him. You took the dick in your throat over and over. You suffered for the pleasure of the other people in the room. More masturbation sounds came from Annalise's side of the room and you wondered if it was her or Lindsay playing.

Dallas pulled out and Jake yanked on the leash, signaling for you to stand. You did so and he led you to the spanking bench on the right side of the room. He directed you to lie on your stomach and you did so.

Dallas slid into your mouth. Jake tore open a condom and moved behind you. His fingers - which were wet with lubricant - slid into your asshole. Annalise moaned.

Your asshole clamped down around his finger as your nerves got the better of you. You'd been fucked before, but only by a strapon. This was different. This was so much different.

"Relax," Jake said. "It's going to hurt like hell if you don't."

He fingered your ass while Dallas fucked your mouth. Annalise had another climax and it sounded like Lindsay did too. Your throat burned from the cock moving in and out of it with great force. Your chin was coated in drool. You felt every bit like the fuck toy you were.

"Hey, baby," Lindsay said.

"Hey there," a deep voice replied.

"Who's this?" Annalise asked.

Dallas pulled out of your mouth and you turned your head to see Lindsay kissing a tall, handsome, naked man. Her fingers encircled his cock and she stroked him, luring him to an erect state in no time.

"This is the girl I mentioned," Lindsay said. "Annalise, this is Andrew. He's going to fuck you tonight. I know you enjoy my strapon and I will absolutely fuck you with it before the night is over, but I think we both know that you like a real man's cock, too, and Andrew is going to give you his cock while your pathetic cuck watches and gets fucked up the ass."

Annalise stood and smiled. "It's very nice to meet you, Andrew."

He smiled. "You too."

Jake's cock slid into your ass as you watched Annalise fall to her knees in front of Andrew. She took him in her mouth and you winced from the pain of being taken anally. You felt Jake's hand crash down on your ass. Your anus tightened up at the pain and Jake moaned.

"Fuck your ass feels good," he said.

Annalise sucked dick on the other side of the room and a wave of jealousy washed over you. You'd never get to experience her mouth in that way. You'd never get to experience her pussy in the way Andrew was going to experience it. You were a sub. A cuck. You didn't fuck. You got fucked. That had been made perfectly clear.

"Fuck his mouth," Jake instructed.

Dallas's cock filled your mouth and your view of Annalise's blowjob went away as you became a fuck toy, taking cock in both holes. They filled you in rhythm with Jake thrusting as Dallas pulled out. Your job was to remain on the bench, to open your holes to them, to let them use you for pleasure.

Annalise moaned like she was getting fucked. Your beautiful domme had a cock inside her but you couldn't see it because you were too busy being filled with dick. You listened, though, and pleasure washed over you like it would for any cuckold who was witness - even aurally - to his domme's pleasure via another man's cock.

"Fuck her harder," Lindsay said. "Make her cum on your cock, Andrew. Make her cum hard while she watches her bitch of a sub take it up the ass and in the mouth."

Jake and Dallas fucked you from both ends. Your jaw ached. Your asshole hurt. Your ass had been reddened from the intermittent spanking Jake delivered. You'd never been subjected to so much stimulation in such a short period of time and your brain had descended into the deepest version of subspace you'd ever entered, leaving you awash in a kind of satisfaction you'd never felt before.

Jake buried his cock in your ass and came. Dallas's cock expanded in your mouth and cum flowed soon after, bathing your tongue in the bitter, salty taste of his seed and triggering a wave of humiliation, though you found it pleasurable.

Annalise came moments later. She came loudly, too. Her screams of pleasure were all you heard in those moments and you felt the purest happiness, for your humiliation had been worth it. It had given pleasure to your domme. It had been partly why she experienced such a potent climax.

Dallas pulled out and you swallowed. Jake pulled out and directed you off the spanking bench and onto your knees. He then emptied his used condom in your mouth and you swallowed your second load of the night.

Annalise approached and dropped to her knees in front of you. She took your head in her hands and smiled before leaning in to kiss you softly.

"I Just had the best orgasm of my life," she said. "Because of you. Because of Andrew's glorious cock, too, but because of you."

"Thank you for letting me submit to you, Annalise. Thank you from the bottom of my heart."

Another kiss followed. "Don't thank me yet. The night is still young and I find myself in a greedy mood. I want more pleasure. More orgasms. More submission on your part."

"I'll do anything to make you happy, Annalise."

She pulled out her phone and held it up. She tapped the screen and you watched your wife get fucked from behind. Her boyfriend grabbed a handful of her hair and spanked her ass. She arched her back and her lips parted. She let out a moan that grew louder. Soon enough she was having an orgasm while another man fucked her doggystyle and spanked her ass. She was cumming in a manner you'd never seen before. She was cumming because someone better than you was fucking her.

Annalise stopped the video and put her phone away.

"That was so fucking hot," you said.

"I know, and if you're good for me tonight I'll release you from your cage and jerk you off while you watch that video and the others she's sent me. I'll make you feel good even if it only lasts a minute or two before you blow your load."

"I'll be good for you," you said as you imagined how pleasurable that orgasm would be. "I promise. I'll be good for you. I'll do anything you want."

She kissed you again and stood. You looked around the room and saw all five people looking at you. The fun was just getting started and you couldn't wait to see how they'd all use you for their pleasure.