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To me, the best thing about cuckolding is that it offers variety. It means I don’t have to resign myself to the slow decline of a sex life that happens in a long term relationship. Desire tends to dry up, especially that wild kind of desire that you experience early in a relationship. There’s no better cure for that than a little bit of cuckolding.

Henry was not a natural cuckold. It wasn’t something he fantasized about. He is, however, a natural submissive, which meant it didn’t take that much work to transition him to being a willing cuckold for me. It began with a simple conversation that took place a few weeks after the bathroom sex I described in the last installment.

With the exception of Henry’s chastity cage, we were both naked in bed. He was on his back and my head was on his chest as I ran my fingers over his thighs and his locked up genitals. I was teasing him, but only in the mildest way.

“Henry, my love,” I began, “Would you agree that you rarely make me cum when we have sex?”

It was a question with only one answer, which Henry offered. “Yes,” he said. I could hear the hesitation in his voice. It was not the kind of thing any man wants to admit to, so of course he was a little hesitant.

“And can you see where that might be a little bit of a problem for me?” I asked.

To be honest, it wasn’t as much of a problem as you might think. I like having good sex, but I actually find a great deal more pleasure in a good domination session. I like cumming while I’m riding Henry’s face more than I like cumming while I’m riding his cock, especially if he’s locked in his cage and desperate for an orgasm while I’m riding his face. Still, I wanted to make him a cuckold and as a submissive man Henry is dedicated to my happiness above everything else.

“I can see that, yes,” he answered.

I could hear his heart beating faster and it brought a smile to my face. Henry knew what was coming.

“Do you know the solution to that problem?” I asked.

Henry knew. It wasn’t the first time I’d brought up the notion of fucking someone else. We’d never had a protracted conversation about it, but Henry was aware of the concept of cuckolding and the idea that if he was going to be with me there was no chance I was going to be exclusive to him forever.

“I think I do,” he said.

I found his reticence to give voice to the notion of cuckolding adorable. It was like Henry thought he could stop it from happening by refusing to acknowledge it was even a possibility.

“What do you think the solution is?” I asked as I teased his balls with my fingers.

“You having sex with another guy,” he said.

“I like to think of it as me cuckolding you,” I replied, “But yes, that’s the solution.”

His heart was pounding harder. I could feel a little bit of tension in his body. Like I said, Henry wasn’t a natural cuckold. It wasn’t something he fantasized about. It was something that made him nervous. I’m sure it’s something that makes most men nervous if it isn’t their fantasy.

I sat up and smiled as Henry glanced at my breasts. Men are so predictable, but there’s something comforting about that. I feel like it’s a real problem when your man stops looking at your breasts, because that means he’s not really interested anymore.

“I know it makes you nervous,” I said as I ran my fingers through his sparse chest hair. “That’s okay. It’s a perfectly natural reaction. I need you to know that I have no intention of leaving you. I’m not going to fall in love with another man. I’m not going to suddenly decide that I’m not in love with you or that you’re not the man I want to marry. You are.”

Henry took my hand in his and brought it to his lips to offer soft kisses. He looked impossibly vulnerable, which I took as a good sign. He was letting his emotions rise to the surface.

“You know I’m different than most women,” I continued. “You know my desires fall pretty far outside what most people would consider normal. I think that’s part of what you like about me, though, and I promise I’ll make it pleasurable for you.”

I straddled Henry and let my pussy settle over his locked up cock.

“Can you feel that?” I asked.

He nodded as my pussy lips opened around his cage. I was certain he felt the wetness between my legs.

I leaned down, kissed his neck, and whispered, “I want another man to feel that. I want my warm, wet, tight pussy to be filled with someone else’s big cock.”

Henry moaned. I don’t know if it was because he found my words particularly appealing or if it was the way I was grinding my pussy on his locked cock or if it was that I was kissing his neck between every few words. It didn’t matter, though. He was turned on and I was associating his arousal with the idea of another man fucking me.

I sat up and played with my tits as I rubbed my pussy on his cock cage. It was actually a little bit stimulating because I could get some good friction on my clit, so when I moaned it was from a genuine sense of pleasure.

“I’m going to cuckold you, Henry,” I said. “It’s inevitable, and it’s going to happen soon. I need to know that you can handle it before we get engaged. It’s very important to me that my future husband be a good cuckold as I want the freedom to pursue my pleasure as I see fit.”

Henry seemed enraptured with me. I’m sure it was partly because he’d been caged for a week at that point. I’m sure it was partly because I was basically masturbating while using his chastised cock. I hoped it was partly because he was turned on at the notion of being a cuckold.

I slid my pussy up his stomach and chest and hovered over his face. “I will make cuckolding pleasurable for you, Henry. I promise. I will be a good cuckoldress. I will take care of both our needs.”

“I know,” he said. “And I’ll be a good cuckold. I will. I promise.”

I believed him. I knew it would be difficult for Henry, but I believed him. Plus, I was confident in my abilities as a domme. I knew that even if Henry found it painful to be my cuckold that I would get him to a place where it was thrilling for him.

“You’ll get a chance to prove it this weekend,” I said. “I’ve setup a date. I’m going to cuckold you.”

I sat on Henry’s face before he had a chance to say anything. I smothered him with my pussy and he groaned before putting his tongue to work. He ate me out like a good submissive should and it wasn’t long before I climaxed.

I kept my pussy on his face afterwards. I covered his mouth with my wetness as I ran my fingers through his hair and smiled.

“Are you going to be a good cuckold this weekend?” I asked when I finally relented and pulled my pussy from his face.

Henry nodded.

“Open up,” I said.

Henry opened his mouth and I smiled before moving back a little and letting the saliva slide out of my mouth and into his. My fingers followed and he sealed his lips around them. He sucked without prompting. There was something so thrilling about it. I pushed my fingers deeper. His eyes went wide. He gagged just a little and again it thrilled me.

“I want you to make me cum again,” I said.

I pulled my fingers from his mouth, sat on his face, and rode it until I had another orgasm thanks to my submissive’s skilled tongue. Henry remained locked in his cage, which is where he would stay until I cuckolded him.


Thinking it was unwise for Henry’s first cuckolding to be with someone I’d never met, I called a guy I’d had a fuck buddy type relationship with a few years back. He was excellent at providing me with the release that comes from good sex and he possessed a big cock, which I thought would be helpful in Henry’s cuckold training. Size doesn’t matter all that much to me, but I thought it would make a difference for Henry to see someone much bigger making me cum hard.

“Tonight will almost certainly be challenging for you,” I explained as Henry watched me changed into a lingerie set I’d bought the day before. “I’m going to give myself to Derek. You’re going to watch him fuck me. You’re going to watch him offer me a kind of pleasure that you’re not capable of offering me. You’re almost certainly going to experience certain uncomfortable feelings.”

I stepped into a pair of black lace panties and slowly pulled them up as Henry stood there and watched. He was naked except for his chastity cage and he had his hands behind his back, as I’d instructed.

“I want you to know that it’s okay to have those feelings. It’s okay to feel anxious and annoyed and maybe even a little bit angry. It’s also okay to feel pleasure. It’s okay to be aroused as you watch someone else fuck me. That might not happen tonight, but it will eventually. You’ll come to find cuckolding hugely thrilling, I promise.”

I put on a matching black lace bra and grabbed the new stockings I’d bought and sat on the edge of the bed.

“Derek knows you’ll be watching. He’s okay with it. You’re not the first man he’s cuckolded, in fact. He has some experience with it and I’ve told him that he can help with your training, so you can expect him to interact with you a little.”

“Okay,” Henry said as he watched me pull one of the stockings up my leg before moving to the other.

“I expect you to do as you’re told tonight,” I said. “You know I’m not crazy about punishments, but I will not hesitate to punish you in front of Derek if you misbehave. I expect you to watch even if you’re not enjoying yourself, though I think you might find it quite enjoyable. Like I said, I’m going to take care of your needs.”

I stood up, stepped into a pair of three inch heels, and asked, “How do I look?”

“You’re perfect,” Henry said. “As always.”

I stepped closer and took his hand in mind. I placed it on my breast and leaned in to kiss him. Henry’s fingers played with my soft flesh and I moaned into his mouth.

“I’m in love with you, Henry” I said.

“I’m in love with you too,” he replied.

I took his hand and moved it between my legs. I pulled the panties aside and Henry’s fingers slipped inside me.

“The idea of cuckolding you turns me on, Henry. It makes me wet. I’m soaked at the mere thought of you watching while Derek fucks me,” I said.

Henry worked my pussy and I moaned for him. I moaned because it felt good. I moaned because I wanted him thinking about sex. I wanted him wishing that he was the one that got to fuck me that night.

I stepped back and Henry’s fingers slipped out of my pussy. I took his hand and led him to the chair I’d placed by the side of the bed.

“Sit,” I said.

Henry sat and I retrieved a pair of handcuffs from the nightstand. “Put your hands behind the chair.”

He did as instructed and a few moments later Henry was cuffed to the chair. I retrieved his chastity key and fell to my knees in front of him. I looked up at my submissive, smiled, and unlocked his cock.

I think he was genuinely surprised when I took him in my mouth. I sucked until he was rock hard and I’m pretty sure I got him close to cumming. I didn’t let him lose his load, of course. I just wanted an unbridled kind of desire coursing through him.

I timed things perfectly, as Derek showed up just a few minutes later. I gave Henry’s cock one last stroke and let the man that would be fucking me that night into the apartment.

“Welcome,” I said.

Derek took a moment to admire me in the lingerie before stepping into the apartment, taking me into his arms, and kissing me with the vigor of a truly confident man. He had good reason to be confident. He knew he was getting laid.

“You look even better than I remember,” he said.

“Thank you,” I replied before leading him into the bedroom.

Derek smiled at the sight of my naked, erect boyfriend cuffed to a chair.

“This is Henry,” I said. “The man you’ll be cuckolding tonight.”

“It’s nice to meet you, Henry,” Derek said. “What’s with the cuffs?”

I smiled and moved towards Henry. I bent over and kissed him as my fingers danced over his still-erect shaft.

“I control Henry’s orgasms,” I explained. “I want him to be able to concentrate on his cuckolding tonight, not on resisting the urge to play with his cock while you fuck me.”

I stood and spun around before sitting in Henry’s lap. His cock slid between my thighs and pressed against my panties as I leaned back. He moaned like I was hoping he would.

“I want to suck your cock,” I said to Derek.

He smiled, as every man does when a woman utters those particular words. He stripped with surprising speed and stepped in front of me with his cock already standing at attention.

I leaned forward and took Derek’s big, beautiful cock in my mouth as I ground my hips over Henry’s crotch. I made a little bit of a show out of the blowjob, too. It was wet and sloppy and loud and I had two men groaning, one because I was giving him all the pleasure I could manage and the other because I was teasing him like a cuckoldress tends to do with her man.

As I offered Derek pleasure I reached down and took Henry’s cock in my hand. I used his copious precum for lube and stroked him slowly, teasing expertly and ensuring that he didn’t cum too quickly. I wanted Henry to associate intense pleasure with me sucking another man’s cock. I wanted to form a new groove in his brain, to ensure that he wanted to see me give head in the future and that instead of producing anxiety it would produce desire.

I let Derek’s cock fall from my lips and leaned against Henry. I turned my head and pressed my lips against his. My tongue slipped into his mouth and he kissed me. I’d just had another man’s cock in my mouth and he kissed me, which was remarkably hot. It really was. He moaned, though that could have been because I was still jerking him off.

I stood up, turned around, and bent over. “Do you want him to fuck me?” I asked as my fingers once again wrapped around Henry’s cock. “Do you want Derek to fuck your girlfriend’s pussy? Do you want him to slide his big cock into my pussy and fill me?”

At that point it seemed like Henry’s desire had overwhelmed everything. He was hard for the first time in 10 days, he’d received a blowjob, and I’d been teasing his cock with my hand for the duration of Derek’s blowjob.

“Yes, I want him to fuck you,” Henry said. “Please.”

He correctly associated his pleasure with Derek’s. I hadn’t explicitly said it, but Henry must have deduced that there was no way he was having an orgasm that night if I didn’t cuckold him.

I looked back at Derek, smiled, and said, “Put on a condom.”

He pulled a condom from the box on the nightstand, tore it open, and slid it onto his cock as I looked at Henry and rubbed my thumb over his cock head. He moaned and writhed in the chair and I felt an intense kind of power, like I had total control over my boyfriend.

“Tell him to fuck me, Henry. Tell him to fuck your girlfriend,” I said.

“Please, fuck her,” Henry said. “Fuck my girlfriend. Cuckold me.”

The last bit made me smile. Henry was getting into it. He knew what I wanted and like a good submissive he was doing his best to make me happy.

Derek slid his cock inside me and I groaned. He was actually a lot bigger than Henry and there is something really nice about the feeling of fullness that comes with being with a man wielding a big cock.

“He’s so thick,” I said as I looked into Henry’s eyes. “It feels so good.”

Derek fucked me slowly and with skill. He took his time so I could get used to his size. I moaned with every thrust and I got to a point where I really wanted him to pound me. I smiled at his skill. He was using his cock very well.

“Harder,” I said. “Fuck me harder.”

I looked at Henry throughout. I wanted him to see my face. I wanted him to see the lust that another man produced. I wanted him to see the satisfaction I felt as I took Derek’s cock. I wanted him to watch Derek fuck me in a position Henry had never been permitted to have me in.

Derek delivered the hard fucking I wanted. He pounded me and I stroked Henry’s cock. The sounds of sex and sensual pleasure filled the room as Derek and I got what we needed while Henry got what I decided he deserved.

Doggystyle penetration doesn’t make me cum. I need a little extra to get off that way, so I reached back to play with my clit. It’s not my preferred way to orgasm during sex, but I wanted Henry to watch me cumming with someone else taking me from behind. I wanted him to see the sex result in an orgasm.

I rubbed my clit while Derek fucked me from behind. I teased the head of Henry’s cock with a thumb just to keep him crazed with the desire to cum. I closed my eyes and the moment I climaxed Derek buried his cock inside me and wrapped his arms around my waist to hold me up as my knees buckled.

I’m not sure why it was such a good orgasm. I think it was because of the circumstance, though. I think that cuckolding Henry – and the domination that went along with it – really turned me on. I think that’s why I felt a huge rush of arousal as I climaxed.

After my orgasm I stood up and had Derek get in the bed. I turned Henry’s chair so he was facing the bed, straddled Derek’s big cock, and sat down on it.

My goal was to make him cum while Henry watched. I wanted him to see my pussy opening for another man’s dick. I wanted him to have an entirely different experience from the doggystyle sex. It was more distant. He was cuffed to a chair while I was facing away from him and indulging in my desire for another man.

I heard Henry groan as I leaned down to kiss Derek. I embraced the pleasures of being with another man while my boyfriend watched. I made him feel good with my pussy and in the process I got to feel fucking great.

Derek and I came together. He grabbed my ass and fucked his cock up into me at a blistering pace. Every thrust was like a little explosion of pleasure on my clit as Henry sat there and watched while cuffed to the chair.

I made sure to orgasm loudly as I timed my climax to Derek’s. I wanted Henry to know how much I enjoyed having someone else’s cock inside me.

We made out a little after the sex. I whispered about how good it felt and how much I enjoyed fucking him. I wanted Henry to know I was saying something but I didn’t want him to be able to hear it. I wanted to tease him a little bit more.

I lifted my pussy from Derek’s cock and worked the condom off of it. A naughty idea struck me. Henry was cuffed so I was free to do as I desired. I pushed my fingers into the condom and coated them in Derek’s cum. I stepped in front of Henry and wrapped my fingers around his cock. I stroked him. I gave him a cum-soaked handjob.

There was a moment where it seemed like he wanted me to stop. It was right at the beginning when his brain seemed to register that another man’s cum was coating his cock. Henry didn’t ask me to stop, though. Instead he closed his eyes and enjoyed the handjob. He let me make him cum.

His orgasm was explosive. His cum flew into the air as I stroked him furiously. It made a spectacular mess, which I found delightful. The sounds Henry made confirmed just how much he enjoyed himself. It was everything I wanted his first cuckolding to be.

Afterwards I thanked Derek with a long kiss and ushered him out of the apartment before releasing Henry from his handcuffs.

“Did you enjoy yourself?” I asked.

“I did,” he answered.

“Good. Clean up the mess you made and then we can shower together,” I said as I stood and walked towards the bathroom.

Henry grabbed a paper towel and got on his knees to clean the floor as I got the shower started. 

All told, his first cuckolding went very well. Better than I expected it would, in fact. That’s why I did it again not long after.

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Comments

MLPESK

that was amazing! so very hot!