The Cuckold Training Diaries - Part 8

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Avery

Remember how I told you about Alonso last time? The 'bad boy' type that I briefly dated in college? The one I was basically addicted to, that I was more than happy to be a slut for?

Well, it wasn't an accident that I brought him up when training Milo. I hadn't forgotten about him, of course, but he hadn't really entered my mind, either. Not until he got in touch, that is. He sent a message on Instagram. He wanted me to know that I still looked good - I'd recently posted a bikini pic and I really did look good in it - and it seemed to me that he was being pretty obvious about his desire to rekindle a little of that excitement we'd experienced together in our college years.

You know what I learned? Alonso hasn't really changed. Most guys grow out of the bad boy thing, mostly because women are a lot less interested in it when they hit their 30s. Alonso didn't grow out of it, though. He wasn't interested in hearing about how things have been for me since college. He was just probing to see if there was a chance I was interested in having the kind of fun we used to have in college, even if it was only over messages on Instagram.

Under normal circumstances, I wouldn't have responded to his message. But, as you know, I'm no longer operating under normal circumstances. I'm training my husband to be a good cuckold because I've decided that I want to fulfill his fantasy, that I want to make it my own, and that we're going to have a damn good time doing it.

You know what works for that? A guy like Alonso. He's perfect for that. He doesn't give a damn about anyone other than himself, which was exactly what I needed in that moment. Now, before you go getting too excited, I didn't fuck Alonso. Who knows where his dick has been in the years since college? I did, however, use him to have some fun, and to indulge in some fun for Milo.

It was a Saturday night. Milo was one orgasm away from getting his release from chastity. I told him I'd planned something special, so he spent the entire day in a state of excitement, and with good reason. He didn't know it, but I'd planned a phone call with Alonso.

I'll admit, I was being selfish. Before I'd started training Milo, I would never have initiated phone sex with Alonso. The idea would have seemed utterly insane to me, in part because the things I did with Alonso used to be kind of embarrassing to me. I was, honestly, a little bit ashamed of just how slutty I'd been with him. It felt like a version of myself that I wanted to leave behind.

Then Milo's cuckold fantasy became a part of my life. In an effort to train him, I started to think about past sexual experiences I could share with him. Suddenly, any sense of embarrassment departed, and in its place was lust. I started to think about what I'd done with Alonso and I got turned on. I thought about the other guys I'd been kind of slutty with when I was a lot younger and I got turned on, because all of a sudden those experiences had become assets in helping me to train my husband.

Plus, Alonso still looks really good. I mean, really good. Better than he looked in college. He's far more muscular now and he's not shy about posting proof of that on Instagram. I'm willing to admit that there were a few instances where I indulged in a bit of self-pleasure as I looked at his pictures and a few of his videos and thought of the things we'd done together, of the sex we'd had. I never let myself cum while doing that, but I got close a few times. I guess I was teasing myself, kind of like how I tease Milo. It worked, too, because I managed to build up a fair amount of desire that I then unleashed during the phone sex.

"Are you ready?" I asked Milo a few hours after dinner.

"Yes," he answered, though obviously he had no idea what he was ready for.

"I've arranged for us to have a little fun tonight," I explained. "You're going to stay in your cage until you've made me cum, but that's going to happen while I have phone sex with someone."

Milo's eyes went wide. "What?" he asked, in that way someone does when they're so dumbfounded that they can't quite process what they just heard.

"Do you remember when I told you about Alonso? The guy I fucked in college? The guy that I couldn't help but be slutty with?" I asked. Milo nodded. "He got in touch on Instagram. We've been doing a little flirting. Reliving a few memories from our college years. Dirty memories. The kind of memories that I shared with you."

Milo's mouth hung open as he stared at me like I was talking in a different language. It was actually pretty amusing. "Wait...really? You've been...you've been talking about sex stuff with an ex-boyfriend?"

I grabbed my phone, opened Instagram, and pulled up my DMs with Alonso. I handed the phone to Milo and watched him scroll as he read. I watched a mixture of pleasure and angst wash over his face. I'd read about the angst in particular, that every cuckold feels it at some point, that he can't help but worry that his fantasy is going to get away from him. I'm not sure why Milo felt it in that moment and didn't seem to mind that I'd actually kissed someone in the bar that night, but he certainly seemed to feel it.

"This...this is incredible," he said, demonstrating that he wasn't waylaid by the angst. "Did you really do all of this stuff you’ve been texting him about?"

I nodded. "I did, and he's going to call soon and we're going to talk about the things I did for him, and while we do you're going to eat my pussy. You're going to give me that final orgasm and earn your release, and you're going to do so while I fantasize about fucking someone else. How does that sound?"

"Like the hottest thing I've ever heard," Milo answered.

I took the phone from my husband, sent Alonso a message letting him know I was ready to talk, and sat on the couch. "Alonso doesn't know you're going to be eating my pussy, so you need to be quiet. And no moaning. He thinks I'm stepping outside my marriage to do this, that I'm eager to cheat on you. He wanted to Facetime but I'm not taking the risk of him recording everything and putting it online. I might send him a picture or two, though. Who knows? It depends on how naughty I'm feeling."

"I'll be quiet," Milo said.

The phone rang. I saw Alonso's name on the screen. I tapped the button to answer it and put him on speakerphone. "Hey there," I said.

Milo

The messages they'd sent each other were astoundingly lurid. They hadn't started that way - they'd been feeling each other out when they first started messaging - but I couldn't believe it was my wife saying some of those things, like the message she sent where she detailed how much she'd enjoyed sucking his cock while he drove them to a concert, or how much she'd enjoyed the way he fingered her to an orgasm while they were riding the bus. There were countless others, too, and as I read them it felt like I'd been given a chance to meet an entirely different version of my wife, a version of her that seemed to be emerging once more.

Then he called. The look on her face changed the moment the phone rang. Maybe it was just the younger version of her - the one that couldn't help but do whatever Alonso wanted - coming out to play. I liked it, though. I loved it, in fact, because that version of Avery seemed like the one that would have no problem cuckolding me.

"Hey there," she said.

"Hey," Alonso replied. "It's good to hear your voice again. You sound just as sexy as I remember."

Avery smiled. "Oh yeah? Well, you look even better than I remember in those pictures you post, Alonso. It seems like you've worked hard to keep that body of yours in shape."

"I like to look good," Alonso said. "It pays dividends to look good. After all, would we be having this call if I didn't?"

"Mmm, maybe not," Avery replied softly. "I'll admit that I did get turned on looking at your pictures and watching those videos you post. It made me think of the fun we had in college."

I gently moved between her legs on the couch and reached up to pull off her panties. Avery smiled at me as I leaned in and softly kissed her thighs. I didn't want to reveal that she wasn't alone, so I made sure to keep as quiet as possible.

"We did have fun, didn't we?" Alonso asked. "What kind of fun were you thinking about, specifically?"

"Do you remember that night we went to that club that was open to anyone over 18?" Avery asked.

"Damn right I do," Alonso replied. "I might be wrong, but I'm pretty sure you put on a tiny little dress at my request. You weren't wearing a bra or panties, either."

"I'd never dressed like that before," Avery admitted. "I felt like I was naked. I wanted to make you happy, though, to turn you on. I wanted to be the only girl you paid any attention to that night."

"You did a damn good job of that," Alonso said. "The way you danced that night...the way you moved, you had my attention, Avery. You had every bit of my attention."

I kissed my way to Avery's pussy and gently moved my tongue back and forth over her clit. I watched the pleasure wash over her face and she moaned softly.

"Does thinking about that night turn you on?" he asked.

"It does," Avery replied before moaning again. "One part of that night in particular."

"Oh yeah?" Alonso asked. "What part is that?"

"The part where you took me to the bathroom," Avery answered. "The part where you took me into the bathroom, pushed me up against the door, and kissed my neck as you fingered my pussy." She moaned again and I moved to put my tongue inside her so I could taste some of the wetness that was almost literally dripping out of her.

"Mmm, I remember that," Alonso said. "You were so wet for me. Are you wet for me right now, Avery?"

"Yes, I am," she answered.

"What happened after I fingered you, Avery? What happened after I made your wet pussy feel good?" he asked.

"I took out your cock," Avery said. "I took out that big, beautiful cock of yours and I stroked it while we kissed." She moaned as I returned to licking her clit. "Someone banged on the door, but you locked it. You didn't give a shit about what anyone else needed. You only cared about what you wanted."

"Damn right," Alonso said. "I wanted your pussy. I wanted to fuck that wet pussy, Avery."

"But you wanted my mouth first, didn't you?" she asked.

It was getting difficult not to groan at that point, almost entirely because my dick was trying desperately to get hard in its cage. It throbbed relentlessly as I got caught up in the pleasure of listening to Avery and Alonso relive a memory from their wild college years.

"I did," Alonso said. "You were always so good at sucking my dick, Avery. I wish you were here right now. I wish I could push you down to your knees and watch you suck my dick right now."

Avery arched her back and moaned in a manner that seemed entirely genuine. I guess she could have been putting on a show, but it seemed like she actually wished she was with Alonso too.

"Mmm, baby, I wish I was there with you too," she replied. "I wish I had your dick in my mouth right now. I wish I could feel your hand on the back of my head like I did that night in the club bathroom. I wish I could feel your big cock stretching my lips."

I heard the sound of Alonso masturbating. It sounded like he'd applied some lube to his cock. Either that or he was using his precum.

"Are you stroking your big cock?" Avery asked.

"I am," Alonso answered. "I can't help it. You've got me so turned on, Avery. You're just as hot as I remember, just as needy for my cock as you were in college."

Avery moaned. "I am. I've been thinking about you constantly since we started messaging, Alonso. I can't help it. I'm so fucking wet right now, so turned on."

"Do you remember how you sucked my balls that night? How I stroked my cock and told you to suck on them and how you didn't hesitate?" he asked.

"I do," Avery said. "I never could say no to you, Alonso. When you got me turned on, all I ever wanted was to make you feel good. I didn't care that I was sucking your balls in a dirty bathroom. I just wanted to do it. I just wanted them in my mouth. I wanted to hear you moan."

I actually had to bite my lip to prevent a moan at that point. That might have been the hottest thing I'd ever heard my wife say, and it was made hotter because it seemed entirely genuine. I mean, I could feel how wet she was. I knew she was turned on. I knew she was utterly soaked with desire.

"Would you suck my balls if you were with me right now, Avery?" Alonso asked. "Would you be a good girl and suck my balls as you looked up with me with those pretty eyes of yours?"

"Yes...fuck yes, Alonso," Avery replied. Her eyes were closed and she'd lifted her shirt over her bra and was lustily grasping her breasts and kneading the soft flesh. "I'd be a good girl for you. I'd suck your balls. I'd lick them. I'd swirl my tongue around them. I'd make you feel so good."

I've never been so turned on. It was like I was being cuckolded, like Avery was making my fantasy come true, only it was just the two of us. I know now that it was the safe approach on her part, and I know now how smart that was of her, as I got a dose of being cuckolded without having to deal with the anxieties of actually watching someone else fuck her.

"What did I do that night in the club bathroom after you gave me head and sucked my balls like a good girl?" Alonso asked.

"You stood me up, spun me around, and lifted the back of the dress. You slipped into my pussy from behind and filled me with one deep thrust," Avery answered. "You pulled down the top of the dress, grabbed my tits, and fucked me hard."

"That's right," Alonso said. "I fucked you good that night, didn't I? I gave your pussy what it needed, didn't I?"

Avery smiled and closed her eyes as I licked her clit a little faster. "You did. Would you fuck me like that if I was with you right now, Alonso? Would you give my tight cunt what it needed?"

"You know I would," he said as the sound of his masturbation intensified. "I'd bend you over, grab a tight handful of your hair, and pound you hard. I'd use that tight, married pussy of yours like it needs to be used. I'd fuck you until you were begging me to cum inside you, Avery."

"Oh, fuck, Alonso, fuck my married pussy," Avery replied as I picked up the pace of my tongue on her clit. Her eyes were shut and she seemed completely lost in what had become a full-blown fantasy. I couldn't help but wonder if the phone sex had become more than she'd planned - in a good way, of course - and that she was on the verge of a massively pleasurable orgasm.

"You like that cock in your married pussy?" Alonso asked. "Does it feel better than when your husband fucks you?"

Avery opened her eyes and looked at me as I licked her clit. "Yes. Fuck, yes, you fuck me so much better than he does, Alonso. You fuck my married cunt so much better than my husband does!"

I can say, without reservation, that there's almost nothing hotter than hearing my wife utter those words. My dick hurt in the chastity cage like I could barely believe, but that didn't matter. Not in the slightest.

"Avery, I'm close," Alonso said.

"Cum inside me!" she cried out. "Cum in my married cunt!"

They came together. Alonso's grunts and groans filled the air as Avery legs trembled on either side of my head while I massaged her clit right through her orgasm. I watched her chest heave and saw her cheeks turn a rosy red color from the intensity of her release. I was riding high on my own form of pleasure, too.

"Thank you for that, Alonso," Avery said. "That was exciting enough that we might have to do that again sometime."

"It would be my pleasure," he replied. "And if I'm ever in your neck of the woods, I'll make sure to let you know."

Avery smiled at me. "You do that," she said softly.

She ended the call and grabbed the chastity key from the coffee table. I stripped and Avery set my cock free. She pushed me onto the couch, straddled me, and we kissed before she lifted her shirt over her head and removed her bra.

"Did you enjoy that?" she asked before leaning forward and brushing her nipples against my lips. "Did you enjoy your little dose of cuckolding?"

"That was the hottest thing I've ever experienced," I answered.

Avery reached down and took me into her pussy. I moaned like it was the most pleasurable thing I'd ever experienced, because it might have been. "I really have been fantasizing about him," she said while riding me. "It's like I can't help myself. My mind just wanders to him, to the things we used to do together, to the sexual freedom I felt when I was with him, like he had a way of making my inhibitions disappear so the purest version of my sexuality could emerge."

"That story about the night club, the bathroom, that was so hot," I said.

"What part did you like best?" she asked.

"The part where you sucked his balls," I answered. "It was just so...so dirty, I guess."

"So slutty?" she asked.

I nodded. It really was, and not in a bad way. Not even remotely bad. It just was spectacularly naughty that Avery had so gleefully offered her mouth for Alonso's pleasure, and that she'd apparently found it hot enough to think about that she got all turned on.

"Would you like it if I sucked the balls of the man I eventually cuckold you with, Milo?" Avery asked as she leaned closer before kissing me softly. "Would you like it if your wife's soft, sexy lips gave pleasure to a man's big, hairy balls before he fucked me?"

"Fuck...yes," I answered as I felt my orgasm approaching. "Avery, I'm close."

"Then cum inside me, Milo," she said. "Cum inside me while you think about your wife being a slut for Alonso. Think about him taking me from behind like he described. Think about him fucking my married cunt until I'm begging him to cum inside me."

"Do you think he'd really fuck you better than I do?" I asked.

Avery smiled and bounced hard on my cock. "There's no question he'd be better than you, Milo. There's no comparison."

That was so fucking hot. Hot enough that I came inside her. She ground her hips into me, ensuring that I had a breathtaking orgasm. It was the kind of climax that left my body truly shaking. It was utterly spectacular, and there were still so many cuckold-fueled climaxes to come.