The Cuckold Training Diaries - Part 6

Click here to read the previous parts of the story.

Avery

I'll be honest with you. Before our trip to the bar I still wasn't entirely sure that I was going to cuckold Milo. I found the idea intriguing - and at times exciting - but I had my doubts. All of those doubts washed away the moment I kissed Carter, though. It was instantaneous, too. The moment his lips touched mine I knew I'd end up cuckolding Milo. I had no idea who I'd do it with, but I knew I'd cuckold him because the kiss was that good.

There was still training to be done before that happened, though. Thankfully, Milo was so turned on by watching me in the bar that he became far more pliant afterwards. I'm certain the chastity had a lot to do with that, of course. It's remarkable what a game changer that was, to be honest. It's such a simple thing, and yet keeping him in chastity seemed to change the way Milo thought and acted. I imagine that's because I was truly in control and that he had no choice but to do as I desired to have a chance at being released from the prison that held his cock.

Let's start with the morning after our night at the bar. I slept exceptionally well - two orgasms from my husband's tongue certainly helped with that - but Milo struggled. Of course he did, though. His cock was locked in a chastity device and he woke up countless times from the pain of his imprisoned dick trying to get hard.

He wasn't cranky, though. Instead, he was desperate. His cock's desire to get hard had been defeated all night, but that only seemed to increase his desire. That, and the fact that he'd watched me share a handful of remarkably hot kisses - not to mention a lovely dance - with another man had contributed to a massive increase in desire for my would-be cuckold husband.

"Good morning," Milo said as he cuddled up next to me, ran his fingers under my shirt and over my bare stomach, and kissed me on the neck.

I smiled as I came out of my sleepy state and turned to see an eager look in his eyes. I knew he was desperately horny the moment I looked at him. I also knew that gave me an opportunity to have a little fun with him, and to try and further his cuckold training in the process.

"How was your first night in chastity?" I asked.

"Hard," he answered, though I heard no anger in his voice. "I woke up a bunch of times, and each time it was from the pain of trying to get hard."

His fingers continued to move over my stomach and I offered up a gentle moan when they moved towards my panties. Milo took it as a sign to run his hand over them and between my legs. I felt a lovely little electric charge of pleasure when he rubbed my clit through the soft lace and I moaned again.

"Do you wish you weren't locked in chastity?" I asked.

"Yes," he answered. "But I understand why I am."

"Tell me why," I said.

"Because I masturbated, which was the one thing you asked me not to do," he said. "Because I showed weakness when I should have been strong. I should have gotten you to twenty orgasms and I failed."

I pushed the covers back and rolled onto my side. I reached into Milo's boxers and took hold of his locked cock. I smiled and ran my fingers over the open part at the tip of the chastity device, teasing him in the only way I could. "Yes, you did, and if you want me to cuckold you, you'll need to be focused on my pleasure, not yours. That's how this has to work. It's okay that you failed, that you couldn't focus on me. That's what the training is for. I'm going to shape you into a good cuckold, Milo. I'm going to train you to be everything I need you to be, and then I'll fuck someone else."

He closed his eyes and moaned in a manner that told me that I had him right where I wanted him. He was turned on and eager to be trained. His mind was ready to be filled with the potential pleasures of cuckolding.

"Do you remember how wet my pussy was when we got to the car last night?" I asked as I lowered Milo's boxers and took his balls in my hand.

He nodded. "You were soaked."

"And why was I soaked?" I asked.

"Be...because you kissed someone else," he said. His voice kind of quivered as he said it, too, like he was utterly overwhelmed by the sensations working their way through his body, which is precisely what I wanted. I wanted his desire to be associated entirely with cuckolding. I wanted every bit of pleasure he felt - even while locked in chastity - to be about cuckolding, for that was the best way to train him to be a good cuck.

"And did you enjoy watching me kiss Carter?" I asked. He nodded. "Did you enjoy watching me welcome his tongue in my mouth?"

He closed his eyes and moaned. I looked down to see that his cock had grown as big as it could - which is to say, not much at all - in the cage and that little bits of his soft flesh were pushing out through the small handful of openings the cage offered. He was suffering just a little bit for his arousal.

"Do you want me to stop?" I asked.

"No," he answered. "Please, don't."

I smiled. It's fun to have a man in that desperate state of mind, when he wants nothing more than to be teased into a deeper state of arousal, even though he finds that arousal painful.

"Did you enjoy seeing Carter's hand on my thigh, Milo? Did you enjoy seeing the way he caressed my leg as he leaned in to tell me how beautiful I was?" I asked.

Milo nodded. "I...I wish he could have gone further. I wish he could have played with your pussy."

"Yeah? Would you have liked that? Would you have enjoyed it if I let another man play with my pussy in the bar? Would you have enjoyed it if I let him slide his fingers into my tight, wet, married cunt while you were watching?" I asked. Before he could even answer I leaned in and kissed his neck. I moaned like I was getting fucked and then I nibbled on his ear lobe, biting down just hard enough to cause a touch of pain, which Milo seemed to enjoy.

"Avery..." he said, but that was all that came out of his mouth. He was every bit as worked up as I wanted him to be, and it was honestly a beautiful thing to witness.

"Have you thought about him fucking me, Milo?" I asked.

"Yes," he admitted.

"Me too," I said, which happened to be true. It was kind of impossible not to think about it, honestly, given how turned on I was at the bar. I thought about it while Milo was going down on me in the car and I thought about it again when he went down on me later that night. Like I said, it was a really good kiss, and Carter's a really good looking guy who clearly knows a thing or two about making a woman feel good.

"Really?" Milo asked with hope both in his voice and his eyes.

"Of course," I replied. "When a man kisses a woman like Carter kissed me, when he makes a woman feel the things he made me feel with nothing more than a kiss and a little bit of touching, of course sex is on her mind, just like sex was on my mind last night."

Milo looked so hopeful, like his cuckolding was right around the corner. He wasn't ready for that, though. After all, he couldn't control himself long enough not to break my rule and masturbate.

"Not sex with you, though," I said. "In case you were wondering. I was thinking about Carter. I was thinking about what it would be like to fuck him. I was thinking about what it would be like to see him naked, to feel his body on top of mine, or to feel him sitting beneath me as I rode his cock. I was thinking about what it would feel like to have him inside me, and how much better it would be than when you fuck me."

Milo groaned and from the look on his face it was a potent mixture of pleasure and pain he felt. That was a good thing, at least in my mind. The pain was a reminder of the fact that he'd broken my trust and was being punished, and the pleasure was a reminder of just how badly he wanted to be cuckolded, which was more obvious than ever in that moment.

"Would you have enjoyed if it I'd taken Carter to our car last night instead of you?" I asked softly.

"Yes," he admitted.

There was never a chance I was going to do that, but I did think about it while Milo was going down on me. There's no harm in thinking about it, after all, and I was curious to see if I'd find the idea pleasurable. I did, of course, and I wasn't kidding about a kiss like the one I shared with Carter being the kind of thing that makes a woman think about sex. We're not that different from men. We get turned on. We get horny. We feel that same kind of desperate desire, and I felt it when Carter kissed me. I felt something awaken inside me. I guess you could call it my inner cuckoldress. You know this already, but that kiss - and the touching and the dancing that went along with it - was good enough to solidify my desire to have sex with someone else.

Of course, there was still training to be done. "How many orgasms have you given me since you selfishly masturbated?"

"Two," Milo answered.

"That's a long way from twenty, isn't it?" I asked.

"Yes," he said.

"I could make it a very, very long way from twenty if I wanted, Milo. I could make it take months. Is that what you want me to do?" I asked.

"No, please, don't," he said.

Now, I suspect there are women out there that would be put off by the desperation I saw in Milo's eyes. I was not one of those women. I liked it, I think because I knew I would need that desperation to train him properly, for that desperation would serve as motivation for him. It would help him be what I needed him to be, which was a willing, pliant cuckold.

"Get my toy," I said. "I want to be fucked by a nice big cock."

The toy was in the nightstand on my side of the bed, so Milo had to crawl over me to get it. I knew he'd have to, but the point was to make him do everything required for me to get fucked by a big cock, and that toy was the only big cock in the house.

"Spit on it," I said as he pulled it from the drawer. "Get it wet for me."

Milo spit on the toy and ran his hand up and down the shaft to spread his saliva around. There was something rather alluring about watching him do it, something that made me tingle in all the right places.

I stripped and spread my legs. Milo got between them without having to be told. He looked up at me and rubbed the tip of the dildo around my pussy, getting it even wetter with the juices that had already begun to flow out of me.

"Do you know why I'm wet?" I asked.

"Because you're thinking about Carter?" he replied.

I smiled. "That's right, Milo. I'm thinking about Carter, about his hand on my leg at the bar, about his lips against mine on the dance floor, about his tongue in my mouth." I was thinking about him. It was all so fresh in my mind that it didn't take much to conjure that beautiful sense of desire I'd felt the night before. It wasn't that big a leap to actually think about Carter fucking me, and why wouldn't I, given that my husband wanted me to cuckold him.

"Can I fuck you?" he asked.

"You can," I replied. "Be gentle at first, though. My pussy hasn't been fucked much recently, as you know. Isn't that a fun part of your cuckold training? You fuck me less and I get a little more desperate for a real dick inside me, making me all the more likely to fuck another man to get what I need."

I could actually feel myself getting worked up as I talked to him. I was getting turned on at the mere notion of training my husband to be a cuckold, and of course at the idea of actually cuckolding him.

It felt good when he slid the toy inside me. He went slow at first, just as I'd requested, and it stretched my pussy in the most wonderful manner. I arched my back a little and moaned when Milo used his thumb to play with my clit. It was the best possible way to start the day, and the fact that his cock was locked seemed to inspire Milo to pay even closer attention to me, for there was no chance for him to do anything else, given the imprisoned state of his genitals.

"Are you...are you thinking about him?" Milo asked, though I could hear the hesitation in his voice, like he was a little nervous to hear that I was fantasizing about someone else.

"Yes," I said. "I'm thinking about him, Milo, and it's so much clearer than it was with the guy from the gym. I actually kissed Carter. I felt his hands on me. I actually felt that he got hard for me when we kissed. I felt that he wanted me. I felt that I could have had him, that I could have gone home with him, that I could have dragged him to our car and fucked him in the backseat, that I could have cum all over his big cock if I wanted."

Milo moaned and I looked down to see that same mixture of pleasure and pain on his face. His dick must have been aching in its cage thanks to an exceptional level of arousal, which I knew was key to his cuckold training.

"Now fuck me harder, Milo," I instructed. "Fuck me harder while I think about Carter."

Milo fucked me harder and I closed my eyes and let my imagination run wild. I thought about cuckolding Milo. I played out a version of the night before where I'd actually accepted Carter's invitation and gone home with him. I played out the great sex we almost certainly would have had. I played out being in his bed with him between my legs and his cock inside me. It felt spectacularly good.

"Fuck me, Carter," I said as I felt my orgasm nearing. "Fuck my married pussy!" That last part was for Milo, of course, and I heard him moan after I said it. That was the idea, and I loved that it worked.

I came hard with the toy buried inside me and Milo's thumb working my clit. I had Carter on my mind - I pictured myself riding his cock while I was cumming, actually - and it felt spectacularly good, just as I wanted it to.

"Thank you," I said as Milo pulled the toy from my pussy. "That's three orgasms. Only seventeen more to go before I let you out of chastity. I'll think of ways you can earn more chances to make me cum, though. I don't want you to lose your mind, after all. I just want to ensure that you're going to be a good cuckold for me."

"I will be," Milo said.

I was confident of that too, but only because I knew I could train him to be the cuckold I needed him to be.