The Cuckold Training Diaries - Part 9

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Milo

After my last orgasm - the one where I came inside Avery after listening to her have phone sex with Alonso - cuckolding was on my mind all the time. Every time I saw Avery in something even remotely skimpy - or naked - I thought of her fucking someone else. Every time she kissed me, or even sometimes when she just touched me, I thought of her fucking someone else. I couldn't help it.

You know why? Because that orgasm was the best I'd ever had. It really was. It was far and away the greatest pleasure I'd ever experienced and I was hooked. I wanted more. I craved it.

Avery didn't lock me back up after the orgasm. She said I'd earned the right not to wear the chastity cage, that she trusted me. She was right to trust me - I didn't cheat - but it was actually more difficult being out of the cage than in it.

You see, when I was in the cage I didn't really have to put in any effort to resist masturbating. I didn't have a choice in the matter. When I was out of the cage, I had to exercise discipline constantly, because I was constantly horny. It was an unyielding thing for me. It didn't take much to get me excited, and once I was excited it didn't take much to get me hard.

For example, I was at work one day. It was four days after the phone sex. Avery messaged me. "I've been texting with Alonso. I couldn't help myself. My pussy is soaking wet. He keeps telling me how he wants to fuck me like he used to, how he wants me to be that slutty girl I used to be. I'm not that girl anymore, but it makes my pussy so wet to think about being her for a night."

That version of my wife - the younger version, I guess - is not one I've ever really met. I've gotten glimpses - that's why the phone sex was so hot for me - but that's the version of her that would make the best cuckoldress. That's the one that would get what she needed - what I couldn't give her - from another guy, which would ensure that she'd actually really enjoy cuckolding me, which is how this whole thing should work.

"What did you say to him?" I texted back.

"I told him I've been thinking about him every day since we had phone sex," she messaged. "That I keep fantasizing about being that girl again, about being slutty for him, about sucking his cock and letting him have my pussy however he wants it."

When you're a cuckold - or a would be cuckold, as I was at that point - to read that that kind of message from your wife is insanely hot. That's why I was hard. I was sitting at my desk and I was hard as a fucking rock. I mean, how could I not be hard? I was so excited that I was leaking precum, which left a stain in the front of my pants. I took a picture and sent it to Avery to let her know she was doing a damn good job turning me on.

She responded with a picture of her pussy, which looked about as wet as I'd ever seen it. I stared at my phone and I thought about masturbating. Her pussy was wet because she was thinking about fucking someone else. She was thinking about cuckolding me and she was turned on, which I took to mean that I'd eventually be cuckolded. I had no idea when or how it would happen - if it would be with a guy like Alonso or a guy like Carter, from the bar - but that wasn't particularly important at that stage. What mattered is that I was certain I'd be cuckolded, which was insanely hot.

"I don't know how I'm going to get any work done," I messaged. "I can't stop thinking about you cuckolding me."

"You're not going to masturbate, are you?" she asked. "You're going to be good for me, right?"

"Yes, I will," I replied.

"Maybe today's just a day where you don't get much work done," she messaged. "Should I send that picture of my pussy to Alonso? Should I let him see how wet he makes me?"

"Yes," I answered. Her face wasn't in the picture. It could have been anyone's pussy, so it seemed harmless.

I stared at my phone. Minutes passed without a reply. I stared at the picture of her pussy. I imagined someone else's cock - Alonso's cock, perhaps - sliding in and out of her. I imagined her getting fucked and my erection continued to rage at my desk. I continued to drip precum, making an even bigger wet spot in the front of my pants.

Then a picture arrived. It wasn't of Avery, though. It was a cock. A remarkably large, fully erect cock. "Alonso liked my picture," Avery texted. "He sent one of his own."

He was bigger than me. A lot bigger than me. He was really thick, too, with a really plump looking head.

"I'm thinking about taking that big cock inside me as I play with my pussy," she texted. "I can't help it, Milo. I can't stop thinking about how good it felt to have that big cock inside me, how good it felt to let go of everything and just be a slut like Alonso wanted me to be."

I set my phone on my desk, closed my eyes, and took a deep breath. I did so because I was struggling with my desire. Memories of the pleasure I'd experienced during and after the phone sex came flooding back. Plus, there was something so kinky and hot about the fact that Avery had once been so slutty. I know people use that word in a bad way a lot of the time, but I don't think of it that way. I love that my wife used to be the sort of woman that was so into a guy and his dick that she'd do just about anything for him. That's really fucking hot to me. Like, really fucking hot, and in that moment at my desk I was having trouble resisting the urge to run to the bathroom and quickly masturbate.

Eventually, an idea popped into my head and I picked up my phone and texted, "You should send him another picture. One with the toy inside you. Tell him that you wish it was his cock inside you. Tell him that you wish he was with you and fucking you while your husband was hard at work."

"Is that what you wish I was doing, Milo?" Avery asked. "Do you wish I was cuckolding you right now? Do you wish I was being another man's slut right now?"

I honestly couldn't help but marvel at the idea that Avery seemed so turned on by the fact that she'd completely surrendered to her sexual desires when she was younger. Because that's all it was. She hadn't been abused by Alonso. He'd given her the kind of sexual pleasure she wanted and she offered herself to him because of that. She'd liked being used. She'd liked feeling slutty, and that was so fucking hot to me. Even hotter was the fact that she clearly still found the idea a massive turn on.

"Yes," I answered. "I wish you were cuckolding me right now. I wish Alonso's cock was inside you. I wish he was fucking you in our house while I'm hard at work."

A few minutes passed without another message. Then Avery sent a picture. The sex toy was inside her. She had it halfway in her pussy. The whole thing was covered in her juices, though. She'd been fucking herself with it.

"That was a good idea, Milo," she texted. "Alonso loved the picture. He loved the idea of fucking me - of fucking your wife - in our home. He loved the idea of fucking my cheating married pussy, which is exactly what he called it."

That part was hot too. The fact that Alonso thought she was cheating and that it turned him on so much. It was a small thing and I'm not really sure why it turned me on so much, but it definitely did.

She sent another picture. It was of the dildo. The tip was covered in some kind of thick white cream that must have come out of her pussy. "It's like he came inside me," she texted. "Would that turn you on, Milo? Would you like it if your wife let another man cum in her pussy while you were at work?"

As I read that text I got as close to cumming without any kind of stimulation as I'd ever been. I really did. It was incredible. Because that's absolutely what I wanted. It's what I'd fantasized about so many times. What cuckold doesn't want another man to cum in his wife's pussy? What cuckold doesn't think that's the hottest thing in the world?

"Yes, I'd love that, Avery," I replied. "I'd fucking love that."

Ten minutes passed before another picture came through. It was a close up of Avery's pussy. She looked even wetter. Her clit was engorged, too. "I just came," she messaged. "Or, really, Alonso just made me cum. We had phone sex again. I couldn't help myself. I wanted to hear his voice. I wanted to hear him describe how he'd fuck me. I needed to hear it."

"You're amazing," I texted.

"Enjoy the rest of your day at work," Avery replied. "And don't you dare masturbate or I'll put you back in the cage and I'll keep you there for months."

"I won't," I replied, though I honestly wouldn't have been against the idea of being locked up again. In some ways, it was a lot easier to be caged than it was to be free.

Avery

It's probably a good thing that Alonso doesn't live nearby, that he's a flight or a very long road trip away. If he wasn't, there's a chance I would have lost control.

If I'm being honest, I honestly wasn't expecting that my plan to train Milo to be a good cuckold would take me down a path that led to Alonso. All I wanted was to talk about an ex-boyfriend in a manner that would arouse Milo. I wanted to give him a taste of what it was like to be cuckolded without taking him all the way there.

I ended up excavating a part of myself that I thought was just a phase. Lots of women go through a bad boy phase, and they do it because it's hot. I'm sure there are lots of smaller, more specific reasons, but really, it's because it's exceptionally hot to get fucked by a guy like that. It's just that most women grow out of it.

Maybe, though, what happens is that most women know it's not sustainable. After all, some women actually marry the bad boy and they end up utterly miserable. Guys like that make terrible husbands.

What about a woman who's not looking for a husband, though? What if that woman has a husband and what if her husband is being trained to be a good cuckold because it's long been his fantasy for his wife to fuck other people? Well then, that woman might find her interest in the 'bad boy' type rekindled.

I'm pretty sure that's what happened to me. I was freed from having to think of Alonso - or guys like him - as a potential life partner and able to fantasize about him as nothing more than a sexual partner. As I've detailed, that was clearly something that appealed to me. I honestly couldn't help but get turned on every single time I thought about him after that night we had phone sex for the first time.

It was a week after that first phone sex session - and a few days after I'd been texting Milo while he was at work - that I had another naughty phone session with Alonso. It began with him sending a simple text: "I want to fuck you. Call me."

Milo was working in the yard. My first instinct was to call him in, but I hesitated. It seemed really hot to me to have fun with Alonso without Milo knowing. I'd call him in afterwards and tell him about it, but I kind of wanted to cuckold him - in a manner of speaking - without him knowing it. So I called Alonso.

"Hey there," he said. "I knew you'd call."

I couldn't help but smile. "Oh yeah? Why is that?"

I could hear the confidence in his voice as he said, "Because you can't resist me." It would have been annoying if he wasn't right. He was, though. I honestly didn't even think about not calling him. "You've been thinking about me, haven't you?"

"Yes," I admitted. "I can't help it."

I heard him unzip his pants. "And why is that? Why can't you help but think about me?"

"Because my body wants what you used to give me," I said.

"Are you naked?" he asked.

"No, not yet," I replied.

"Get naked for me, baby," Alonso instructed. "Get in the bed you share with your husband."

I did as he asked. I stripped of every article of clothing and climbed into bed. Milo's side of the bed, actually. Just for fun. "I'm naked," I said. "And in bed. On my husband's side of the bed, in fact."

"That's a good girl," Alonso said. "Now tell me, Avery, is your pussy wet?"

I reached down and slipped two fingers into my pussy with ease. I closed my eyes, arched my back a little, and moaned. "Yes, my pussy is wet. It's wet for you, Alonso. It's soaking wet for you."

I heard him masturbating. He moaned, too. He liked hearing those words from a married woman. "I want to see it, Avery. I want to see your wet pussy. I want to see the pussy that you're so desperate for me to fuck."

I felt a delightful tingling between my legs. I was turned on enough for my pussy to tingle in that astonishingly sexy way, and it was amazing. "I'll take a picture," I said.

"No," Alonso replied. "I want to see your pussy live, Avery. I want you to use Facetime. Talking and taking pictures is fun, but why bother with that when we can do it live. Let me see that wet married cunt of yours, Avery. Let me see the cunt that I used to fuck so good, that used to make my dick feel so fucking good."

I couldn't resist. I tapped the button. I pointed the camera at my pussy. I saw Alonso's face. I saw him smile. I saw his joy as he stared at the cunt that he used to fuck so good.

"You were right," Alonso said. "You're wet for me, Avery. Is it my dick that you crave? Do you wish I was there to give that pussy of yours a hard pounding? Do you wish I was there to give you what your husband clearly can't?"

I reached down to rub my clit. "Yes, Alonso, I wish you were here to pound my tight little cunt. I wish you were to pound me like my husband can't." In the moment, every bit of that was true. I really did wish Alonso was there to cuckold Milo.

"Show me those pretty tits of yours, Avery," Alonso instructed.

I moved the phone into place and captured a shot of my tits for him as I continued to play with my clit.

"Do you remember that time I fucked those perfect tits of yours in your roommate's bed?" he asked. "You were on your back. You wrapped them around my dick. You told me to fuck them. You begged me to cum on them, too. Do you remember begging me to cum on your pretty tits, Avery?"

I moaned. I remembered it. There was something so naughty about doing it in my roommate's bed. I remembered enjoying the sight of Alonso straddling me and looking down at me with that wild sense of lust in his eyes, like he was in a kind of sexual heaven while fucking my breasts.

"Do you remember where I came, Avery?" he asked.

"Yes," I said. "You came on my face."

Alonso pointed his phone at his cock and I watched his hand move up and down the long, thick, spit-soaked shaft. I remembered him doing that same thing while straddling me. I remembered knowing - for just a few seconds - that he was going to cum on my face. I remembered feeling some level of excitement in those few seconds, though the actual facial was less pleasant. I mean, of course it was. That's not the point of a facial, though. That's purely for a man's pleasure.

The crazy thing was that I was actually kind of turned on by the idea in that moment, probably because I knew there was no chance of actually receiving a facial. It was pure fantasy, and there's something really hot about the way you can just let go when you're dealing with pure fantasy.

"I want you to cum on my face, Alonso," I said. "But I want you to make my husband watch while you do it. I want you to make him stand there and watch while you cum on his wife's pretty face."

I have no idea where that came from. I really don't. It just came out. It felt so fucking good, though. So fucking good that I came. Alonso did too. He came hard, at least based on the way he moaned while the cum erupted from the tip of his cock.

"Holy shit," he said afterwards. I was thinking the same thing. Holy shit. What a great orgasm. "Avery, that was fucking hot."

"Yeah, it was," I replied. "Thank you for asking me to call you."

Alonso chuckled. "Believe me. It was my pleasure."

"I'll talk to you soon, I'm sure," I said.

"I can't wait," he replied.

The call ended. I sent Milo a text. I told him I'd just had phone sex with Alonso and that I wanted him to cum inside so I could tell him all about it. It didn't take long for him to show up in the bedroom doorway.

I shared the details of the call. I told him everything, including how Alonso had cum on my face in college. I saw how much that turned him on. I was in a generous mood, so I let him fuck me while I told him how much I'd enjoyed letting Alonso cum on my face, even if it wasn't entirely true. It didn't take long for Milo to cum inside me. Less than a minute, in fact, which, as it turned out, was a perfect piece of cuckold training, as cumming so quickly isn't a way to satisfy a woman, and it’s good when a cuckold feels like he can’t satisfy his wife.

There's more training to come, and some actual cuckolding, too, so stick around.