The Cuckold Training Diaries - Part 16

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Avery

When this all started, my sex life was fairly typical. On a good week, Milo and I fucked a few times. On a bad week, we didn't fuck at all. For the most part, we were both happy enough with it, just like any couple that's been married as long as we have.

I knew things would change when I agreed to train Milo to be a cuckold, but I honestly had no sense of just how different things would be. Because it hasn't been a small change. I've become an entirely different person. Or, I suppose, it might be more accurate to say that I've unleashed the slut that's always been inside me and that I'd merely shoved deep down because it's not really appropriate for a married woman to be a slut.

It's appropriate for me now, though. It's what my husband wants me to be. It's what he gets off on. And, as it turns out, it's what I get off on when I'm with the right man.

For instance, on Alonso's last night in town he took me out to dinner and he invited Milo along. Alonso insisted on a booth and he and I sat next to each other while Milo sat across from us. He was locked in chastity - that was my choice - and I was wearing a tight top and a short, pleated skirt. It was a decidedly slutty outfit, but on that night it turned me on to dress that way because I was doing it for Alonso.

After the waitress took our drink orders, Alonso turned to me, smiled, and slipped his hand into my top. I wasn't wearing a bra, so he grasped one of my breasts with ease. The old me would have freaked out if Milo had done something like that in a fairly nice restaurant. The new me looked at Alonso with worshipful eyes and leaned back to give him easier access so he could play with my tits however he pleased.

I'm pretty sure that turned him on, as he leaned in to kiss me. He pushed his tongue into my mouth and I sucked on it like he was offering his cock. His fingers found my nipple and he pinched it hard. I moaned into his mouth from the mixture of pain and pleasure that emanated from my nipple and I felt my pussy tingling with the same kind of overwhelming need I'd experienced the moment I'd met Alonso at the airport.

He pulled his hand from my shirt, turned to face Milo, and said, "So, is it everything you'd hoped it would be?"

Milo stared at him for a few moments and asked, "Sorry, what do you mean?"

"Being a cuck," Alonso said. "Being locked in a chastity cage while your wife gets fucked by someone else. Is it everything you wanted it to be?"

"Yes," Milo admitted. "It's actually been better than I thought it would be. Avery's...well, it's like I've met an entirely different version of my wife. One I didn't really know even existed. I love that she exists, though. I really do, and I feel like she's actually happier now that she's in touch with this part of herself again."

Alonso looked at me and moved his hand to my thigh. The waitress came over with our drinks and set them on the table as Alonso's fingers neared my pussy. She asked if we were ready to order and Milo asked for a few more minutes as Alonso held my gaze. I'm not sure I would have been able to think about food with his fingers moving over my inner thigh, so I was grateful for Milo's intervention.

"Are you happier?" Alonso asked.

"Yes," I admitted.

"So you like having a cuck husband?" he asked.

"I do," I said.

"I guess I like you having a cuck husband, too," Alonso said with a smile. "After all, this weekend wouldn't have happened without that."

I leaned closer and kissed him softly. "I wouldn't have been able to suck your beautiful dick so many times. I wouldn't have given you my pussy so many times. I wouldn't have made you cum so many times. You wouldn't have made me cum so hard so many times. None of that would have happened without Milo's need to be a cuckold."

Alonso turned to Milo and his fingers pressed against my panties and rubbed in slow circles. I closed my eyes and bit my lip to suppress the moan that desperately wanted to escape.

"Did you enjoy licking my cum out of her pussy, cuckold?" Alonso asked.

There was something about the confidence in his voice - and the delight he took in asking my husband that question - that I found so fucking hot. The pleasure his fingers offered my pussy was suddenly more potent and I was actually quite close to cumming right there at the table from what amounted to a fairly light bit of foreplay.

"Yes, I enjoyed it," Milo answered.

I opened my eyes to see him looking down at the table like he was too embarrassed to meet Alonso's gaze. "Look at him when you answer his questions, Milo," I instructed. It felt like an opportunity to further Milo's training and I didn't want to pass it up. "Show him the respect he deserves. After all, the orgasms he's given me this weekend are far superior to the ones your cock provides me."

Milo lifted his head and stared at Alonso. I could see that it was difficult for him and it pleased me that he was willing to do so at my instruction.

"I enjoyed licking your cum out of her pussy," Milo said.

Alonso pulled my panties aside and I spread my legs a little wider for him. His fingers rubbed over my swollen, slippery labia and then he invaded my pussy. I couldn't close my mouth fast enough and a moan escaped, though the restaurant was loud enough that it was likely no one heard it.

"Did you enjoy it, Avery?" Alonso asked. "Did it turn you on to watch your husband lick my cum from the pussy I've owned this weekend?"

"Yes, it did," I answered. It was true, in part because I've come to enjoy watching Milo indulge in his fantasy and in part because watching him clean Alonso's cum out of me felt like Milo offering his overwhelming approval of me letting my slutty side take over for a weekend. Plus, he'd made me cum with that talented tongue of his, capping off a day of intense pleasure with a beautiful orgasm.

"I think you should thank me, cuckold," Alonso said.

Milo didn't want to. I could see it in his face. He didn't want to suffer the relatively small - at least to my thinking - humiliation Alonso wanted to extract from him. It felt like yet another opportunity to further Milo's training.

"Do you have a problem with that, Milo?" I asked as Alonso continued to slowly finger me under the table.

He looked at me and I saw his hesitance. I saw the lack of desire. I saw just a hint of agony, like asking him to thank Alonso was truly painful.

"I want you to thank him, Milo," I said. "I think he deserves to be thanked for the pleasure he's given me this weekend." Alonso rubbed my clit and I grabbed the edge of the table as I fought off the urge to orgasm. I closed my eyes for a few moments and then looked at Milo once more and said, "A cuckold should be willing to thank to the man that satisfies his wife. You should be willing to express your gratitude, for your fantasy wouldn't come true without a man like Alonso to fuck me, Milo."

Milo looked at me, looked down at his hands, and finally looked at Alonso. "Thank you," he said. "Thank you, Alonso, for fucking my wife."

It pained him to say it. That much was obvious. But, I'm also certain there was at least a bit of pleasure in it for Milo. The sort of pleasure a cuckold feels when he's made to do something a little bit humiliating, especially when his wife is being fingered by another man while he's enduring that bit of humiliation.

The waitress returned to take our orders and Alonso pulled his fingers from my pussy as she reached out table. He placed his hand on the table and I saw her look at his fingers, no doubt seeing that they were shiny.

I placed my order first and then the waitress looked at Milo. As she did, Alonso turned to me, lifted his fingers, and held them in front of my mouth. He didn't say a word, but it was clear what he wanted me to do. I surprised myself by doing it. I took his fingers in my mouth and sucked my juices off of them and I did while my husband was ordering his dinner. I fellated Alonso's fingers like a slut would do and I found it massively arousing.

"And...and you sir?" the waitress asked as she turned to Alonso. "What can I get you for dinner?"

I closed my eyes and kept sucking on his fingers. I had no idea what the waitress was thinking, but I imagine she would have walked away if she found my behavior unsettling. I thought I heard a little excitement in her voice, but that was probably me just hoping she was excited.

Alonso placed his order, the waitress walked away, and he pulled his fingers from my mouth. They disappeared under the table a moment later and slipped inside me. He pushed them deep - and filled me without difficulty, given how wet I was - and leaned over to kiss me as his other hand once more reached into my top to play with my tits.

My legs trembled from the intensity of the pleasure I felt and I happily took Alonso's tongue between my lips and sucked on it like I had his cock in my mouth. There was a part of me that wished that's exactly what I was doing in that moment, as I wasn't really myself. I was the slutty version of myself I'd been in college, the version of me that only existed around Alonso, the version of me that had awoken once Milo had asked me to cuckold him.

"I want to fuck you," Alonso whispered. "Now."

I smiled. I would have fucked him right there at the booth. "I'm yours," I replied. I heard Milo moan, which was so fucking hot, not to mention that it was absolute proof he was every bit the cuckold I'd trained him to be. He loved that I was so enamored with the way Alonso made me feel that I was willing to give myself to him in any way he desired.

"Good," Alonso said. "Follow me."

He took my hand and slid out of the booth. I followed and we strode through the restaurant and towards the bathrooms. The waitress caught my eye and smiled - it struck me as a knowing smile - as we walked past her. Alonso knocked on the door to the ladies room, waited a moment for an answer, and then pushed inside. He locked the door, pushed me up against it, and kissed me with a fervent passion as he reached under my skirt and fingered me so vigorously that my legs trembled as juices dripped out of me.

As we kissed, I managed to get Alonso's pants around his ankles and the moment he pulled away I sank to my knees, yanked his underwear down, and took his big cock in my mouth. Alonso's hands found their way into my hair and he started fucking my face. He used my mouth as I knelt on the bathroom floor and my pussy gushed. I thought of Milo sitting in the booth while I sucked another man's cock. I thought of his cock throbbing in its little cage. It made me even wetter.

After a vigorous face fucking, Alonso pulled out of my mouth, helped me to my feet, and led me to the sink. He stepped behind me, bent me over, lifted my skirt, and slid into me from behind. He buried his cock in me with one deep thrust, grabbed a handful of my hair, and pulled back until I was looking at myself in the mirror.

"Your pussy is soaked," he said before pulling out and thrusting so hard my legs shook.

"It's you," I replied. "I don't know what it is, Alonso, but you make me wet. The way you treat me...the way you fuck me...there's something about it...something I crave...something that turns me on like nothing ever has."

He smiled, pulled out, and slammed his cock into me again. I moaned and looked at him in the mirror. I saw a hint of aggression in his eyes, as if he felt a complete sense of ownership over me, like he could do whatever he pleased with me and I wouldn't stop him. That was probably true. I probably would have let him do just about anything to me in that bathroom, mostly because it had always turned me on to let Alonso do as he pleased with me.

He chose to fuck me hard. He kept me bent over the sink with his hand in my hair and he fucked me as hard as I've ever been fucked. It hurt a little, but in that way that feels so good when it's delivered by the right kind of man. In fact, it felt good enough that I came before he did. I came so fucking hard I couldn't even keep my eyes open. That was the moment I felt most like a slut, and I mean that in a good way. I was getting absolutely railed by a man that I'm fairly certain saw me as little more than a sex toy and I was cumming so hard that I felt like I might actually fall over. That was the sluttiest I've ever been, and it felt so fucking good.

Alonso didn't slow down a bit. He kept on pounding me until he came. He buried his cock inside me and unloaded in my pussy, grunting and groaning and playing with my tits as he did. I looked at him in the mirror and smiled, for I felt an uncommon kind of bliss at having given him such pleasure.

Eventually, he pulled out, put his cock back into his pants, and said, "Stay right there. I'm going to send in your cuckold."

He smacked me on the ass and walked out.

Milo

I watched them go, knowing full well that Alonso was going to fuck my wife. I knew he'd fuck her hard and fast. I knew he'd use her in the way she clearly loved being used when she was with him. I was tempted to follow, but I hadn't been asked and more than anything I wanted to be a good cuckold, so I stayed at the table.

I sat there and waited while I imagined what they were doing. I imagined Alonso fucking Avery in the bathroom, as I was fairly certain I'd seen them head that way before they were out of sight. It seemed so...dirty...but in the best way possible. A woman had to be truly consumed with lust to fuck a man in a public bathroom, and I loved that my wife felt that way about Alonso. I loved that she was so horny for a man that she was willing to let him have her in that way.

When Alonso returned to the table without Avery, I was cautiously hopeful. "She's waiting for you in the ladies room. Make sure you clean her," he said, validating my hope.

I slid out of the booth to head for the bathroom but Alonso grabbed my arm hard enough for it to hurt.

"What do you say, cuckold?" he asked.

"Thank you," I said. "Thank you for fucking my wife. Thank you for...thank you for cumming inside her, for letting me clean her."

He smiled, took a few moments to soak in my willingness to give him what he wanted, and then let me go. It was undeniably humiliating to utter those words - to thank him for fucking her and cumming inside her - and yet I felt excited as I did so. Of course, even feeling that excitement was humiliating, but none of that stopped me from rushing towards the ladies room.

I pushed open the door and found Avery bent over the sink with her skirt up around her waist and her panties pulled to the side. She looked at me and said, "Lock the door." I did so and then rushed to her. I ran my fingers over her ass and Avery looked over her shoulder and asked, "What did he say?"

"To come and clean you," I replied.

"Are you going to do as you were told?" Avery asked.

"Yes," I answered.

Her smile confirmed that I'd given the answer she was looking for. It made it hotter to drop to my knees behind her, spread her ass cheeks, and lean in. Knowing that Avery wanted me to lick Alonso's cum out of her in that bathroom made it so much fucking hotter to do so.

I did it with vigor. I pushed my tongue as deep in her pussy as it could go and I lapped up his load. It was different than the first time I'd done it. His cum was fresher, and thicker, and there was more of it. The taste was a little overwhelming at first, to be honest, but I was so turned on that nothing would have stopped me.

I used my thumb to play with Avery's clit while I cleaned her and she rewarded me with a low, beautiful moan. The more turned on she got, the more of Alonso's cum leaked out of her. I lapped it all up, soaking my tongue in the salty flavor of his load and swallowing every drop.

I managed to give Avery an orgasm, and I like to think that my willingness to be a good cuckold - to show off that her training had been effective - was at least part of the reason she had what seemed like an excellent climax.

When we'd both finished, Avery stood and helped me to my feet. She reached up, caressed my face, and leaned in to kiss me. We shared in the taste of Alonso's cum - it wasn't the first time that weekend that she'd tasted his cum - and I felt the most intense surge of desire between my legs, leading to a beautifully painful throbbing in the cage.

"You're a very good cuckold, Milo," she said.

I smiled. "Well, I've had a very good trainer."

She kissed me again and whispered, "We're just getting started, baby. I have plans for you. Such wonderful plans."

I knew she wasn't going to share what those plans were - maybe she didn't even know - but I sure loved hearing the lust in her voice as she said it, as it meant there was lots more naughty fun in my future.