The Cuckold Training Diaries - Part 17

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Avery

I shouldn't have been surprised, and yet I was. I think it's because I just didn't think about it. I didn't consider that sex with Milo would change considerably after I'd trained him to be my cuckold.

It did, though. In fact, it changed so significantly that I was no longer able to find the same pleasure in it. In hindsight, that makes perfect sense. After all, I'd fucked several men that were far better than Milo over the course of his training, so no wonder it was underwhelming to have him inside me.

Because of that, sex between us changed, though I think it changed for the better. I don't think Milo would argue with that, either, as he's stated numerous times that he finds such intense pleasure in being a cuckold that he's willing to do just about anything to ensure that he gets to keep being one.

Let me take a step back, though, to the day it became obvious that sex had changed. It was three months after Alonso's visit. I'd been with three guys since that glorious weekend. The relationships were all ongoing - it was kind of like having three bulls at the same time, though I hadn't fully committed to that kind of relationship with any of them - and I was getting fucked at least twice a week and sometimes four or five times. It was glorious.

The day in question was a Sunday. I'd been with one of my bulls the night before and he'd satisfied me in a rather glorious manner, as they always do. Milo was in chastity - he'd been locked for a little less than a week at that point - and I decided he deserved to come out on Sunday.

It wasn't, however, a day of kink. We were a couple like any other. We went to the park, then saw a movie, then had a dinner out. I was in a bit of a romantic mood when we got home, so I took Milo to the bedroom with the intention of having non-kink sex with my husband.

I was turned on. Not as turned on as I get when cuckolding Milo, but I was turned on. I was wet when he slid into me. It felt good, too, but not nearly as good as when I'm cuckolding him. It didn't feel nearly good enough to make me cum. In fact, I didn't get close to an orgasm.

Milo came, of course. He'd been denied an orgasm for a week, so he had no trouble getting off. He could sense that I hadn't really enjoyed myself, though.

"That wasn't good for you, was it?" he asked afterwards.

"No," I answered bluntly.

"I'm sorry," he replied.

I rolled onto my side and caressed his face. "It's not your fault, Milo. Not really, at least. We probably should have expected this."

"We should have?"

He looked like he desperately wanted to deny what seemed to be such an obvious fact, but of course he did. One of the harsh realities of becoming a cuckold is that your wife is welcoming better men into your bed and into her pussy. If she wasn't, she wouldn't bother cuckolding you, and that's absolutely what happened with Milo and me. Every man that fucked me was better than him. Every man had a bigger cock and used it better than Milo used his.

"Of course we should have, Milo," I explained. "My body - my pussy - now expects something more than you're capable of giving me. It expects something better because it's gotten something better so many times since I first cuckolded you."

He looked a little heartbroken, though the question that followed explained the look. "So...are you saying I won't be able to have sex with you anymore?"

To be honest, the thought had crossed my mind. I quickly dismissed it, though, as sex is an important part of a marriage. "No," I said while caressing my husband's face. "Sex between us just has to change a little." I smiled as a thought occurred to me. "My pussy will become a reward for you, a reward for being a good cuckold and a good husband. A reward that you'll have to earn."

His eyes filled with hope. "I can do that. I can be a good cuckold and husband. I can earn that reward."

"You'll also have to clean your mess out of my pussy each and every time," I explained. "And you'll have to make me cum while you do it."

I could see that he felt a little hesitant about that part. Of course he did, though. No man wants to eat his cum after he's blown his load.

"That means you need to start cleaning right now," I continued. "Get to work, Milo."

He did as I instructed. He moved between my legs. He put his tongue inside me. He licked his cum out of me like a good boy, and he did so while gently rubbing my clit with his thumb. He understood his place, even if he didn't entirely enjoy the act of licking his sticky spunk out of my freshly-fucked hole.

"That's a good cuckold," I said. "I like that you understand your place, Milo. I like that you know your role, that you no longer question me when I tell you to do something. I like that you're such a well-trained cuck."

He didn't say a word. He just pushed his tongue deeper into my pussy. He rubbed his nose against my clit, doing so as his lips curled into a smile. I moaned because it felt fucking great and I was honestly getting off on the power I felt in that moment as my husband offered his obedience without question.

"Show me your tongue," I said. "Show me the cum."

He lifted his head, opened his mouth, and stuck his tongue out. I saw the strings of thick cum. I saw what he was devouring out of me and there was something so spectacularly filthy about it that I got even more turned on.

"Fuck, suck on my clit, Milo," I instructed.

He went back to work, focusing all his efforts on my clit like a good boy. It wasn't long before he had me shuddering with pleasure. It wasn't as good an orgasm as the other men in my life provided me, but it was good.

That night set the template. Sex with Milo was no longer as it used to be. It was no longer a husband and wife making love. It was a hotwife granting her cuckold the pleasure of enjoying her pussy because he'd earned it by being a good boy.

It was also a way to further Milo's training, as immediately being made to clean his cum out of me was a perfect way of restoring the headspace I needed him to exist in, a headspace in which he embraced the idea that he was sexually inferior to the other men in my life, that he should have to do things like lick his cum out of my pussy despite his total lack of desire to embrace such a thing.

It was a beautiful evolution in his training that started us down the road to a more advanced version of this lifestyle that both of us had grown to love so deeply.

Milo

Lorenzo came along almost nine months after Avery cuckolded me for the first time and he was the first guy she'd fucked that wanted to occupy the position of her bull.

He fit the bill, too, at least as far as I could see. He had the sort of dominant attitude that Avery liked and that a good bull seems to have. He had a big cock that he used exceptionally well, of course, but that goes without saying since Avery wasn't about to let a lesser cock inside her.

Lorenzo also happened to find great pleasure - more than any other guy Avery had fucked - in the fact that she was married to a cuckold. The other guys enjoyed that she was a married woman, but Lorenzo was different in that he took great interest in the hotwife/cuckold dynamic and the fact that Avery was training me to embrace my position in every imaginable way.

It probably won't surprise you to learn that Lorenzo's cock was the first to pass my lips. It was two months into his relationship with Avery when it happened the first time.

By that point I was in a chastity cage the vast majority of the time, barring occasions where it was too complicated to wear it, like going through an airport or an important event where we didn't want to take the risk of anyone noticing. Otherwise, I was locked all the time and released only when I'd earned an orgasm or for a cleaning. I'm not sure if Lorenzo was responsible for my excess of time in the cage or if Avery was so satisfied with him that she saw little reason to give me any freedom, but whatever the reason, I was locked up most of the time.

On this particular night I'd been locked for nearly two weeks. Avery and Lorenzo had fucked half a dozen times in that span and I'd witnessed four of those occasions.

It's worth mentioning that - in my opinion, at least - Lorenzo fucked her better than anyone she'd ever been with, including Alonso. He certainly had a bigger cock and he offered a kind of dominance that seemed like a mixture of how Alonso fucked - where he was really just using Avery's body - with a greater sense of connection that seemed to help my wife experience a deeper kind of satisfaction. The end result was that she wanted Lorenzo all the time and that when they fucked he almost always had her more than once.

That meant I got to witness a lot of great sex. I got to see my wife take another man's cock in every position imaginable. I got to see her cum over, and over, and over again with Lorenzo's dick buried deep inside her. In other words, I got to live out a cuckold's ultimate fantasy, since nothing turns me on more than Avery having a great orgasm with someone else's dick in her pussy.

A week before the night in question - the night where I sucked dick for the first time - Avery and Lorenzo had dispensed with using condoms. He'd already barebacked her twice, once at his place and once in our bed. I'd cleaned his cum out of her when they fucked in our bed and Lorenzo had enjoyed it - and gotten so turned on at witnessing it - that he'd fucked Avery again mere minutes after I'd finished cleaning her messy pussy.

It was all a prelude to the night where I took what felt like a massive step in my cuckold training, the night where I willingly took another man's cock in my mouth for the first time.

It began with Avery and Lorenzo going on a date. I dressed her for that date, which was, as always, hugely pleasurable. I did everything. I put her in the bra and panty set she'd picked out for her bull. I put her in the stockings and I attached the garters. I put her in the low cut red dress she wore. I zipped her up. I even slipped the high heels onto her feet. If I had any skill at doing makeup I would have done that, too.

I remained at the house while they were out. I prepared the bedroom for their arrival - which really just meant cleaning up, pulling the covers back, and making sure towels were easily accessible - and cleaned the house. They were gone for three hours and I was naked, chastised, and waiting when they got home. They walked hand-in-hand to the door - there's something about seeing Avery hold hands with another man that I love - and I opened it for them and greeted my wife and her bull while locked in my cage.

They stepped into the house and I served them both a drink. A glass of wine for Avery and a cocktail for Lorenzo. They sat on the couch to enjoy their after dinner drink. They talked, they flirted, they touched, they did a little kissing. I had been ordered to my knees just a few feet from the couch and I remained there and watched without either of them acknowledging me.

Once Avery had finished her glass of wine she couldn't contain her desire for Lorenzo. She started kissing his neck and stroking his cock through his pants. He smiled, sipped the drink I'd made for him, and let Avery work to get him turned on. I imagine he was more than ready to fuck her - they typically fooled around in the car and in the restaurant when on a date, so I'm sure he was ready to go - but he liked to make her work for it a little as a way of showing off a touch of dominance.

Eventually, he let Avery unzip his pants and pull out his cock. She was genuinely delighted when he gave her permission - offering no more than a nod to do so - and seemed like she her submissive side had been well-stoked at that point.

I remained on my knees with my gaze fixed on both of them as this all unfolded and I can remember how astoundingly hot it was when Lorenzo put a hand on the back of Avery's head and pulled her mouth to his cock. He didn't say a word and she offered no resistance. He demanded a blowjob and my wife offered her mouth.

It was both his sense of control and her willingness to surrender to it that turned me on so much. It felt like he was demonstrating his superiority to me, as there was no chance Avery would ever let me direct her mouth to my cock like that. Not in a million years.

As she sucked his cock, Lorenzo gestured for me to come closer. I crawled towards them as he worked Avery's dress up around her waist, exposing her pussy. I wasn't sure where her panties had gone, but she was no longer wearing them, a notion I found quite thrilling.

"Eat her pussy," Lorenzo instructed. "Get her nice and wet like a good cuck."

It wasn't the first time he'd instructed me to prepare Avery's pussy and I did so without hesitation. She didn't need to be any wetter, but I knew that getting her wet wasn't really the point. My submission was the point. Eating her pussy because Lorenzo had told me to was the point and I happily accepted and embraced that.

Avery moaned around her bull's cock as I licked her pussy and when he put a hand on the back of her neck and pushed down she made every effort to deepthroat him. She moaned while doing so, too, which was a remarkably sexy thing to witness.

"Kiss him," Lorenzo said as he released his grip on the back of her neck.

Avery's head popped up and she leaned down to kiss me without bothering to wipe the saliva from her lips. Her tongue pushed into my mouth and she offered me the pleasure of reaching down to play with my locked cock while sharing a wealth of saliva with me.

As we kissed, Lorenzo stood and stripped. He stepped closer and the moment the kiss ended he grabbed a handful of Avery's hair and guided his cock into her mouth. I watched him fuck her face from six inches away. I watched her lips stretch around his fat cock. I saw her throat expand as she took everything she could. I saw her eyes water and heard her gag. I saw her hand move between her legs to play with her pussy because the mere act of taking a face fucking from her bull was a turn on.

Lorenzo pulled out and Avery gasped for air. I stared at the head of his glistening cock for a moment before my wife kissed me again. I closed my eyes and she pushed her tongue into my mouth. I felt something soft and wet against my cheek. It was Lorenzo's cock. It had to have been. My heart pounded as I felt genuinely nervous about what would come next.

Avery pulled back and Lorenzo's cock rubbed over my lips. I kept them closed, though. I looked up at him as Avery stroked his shaft and played with his balls. For a few seconds, neither of them said a word and I kept my mouth shut.

"Open up, cuck," Lorenzo said. His voice was calm and controlled, and yet he looked both serious and utterly determined to make me do as he desired.

I kept my lips closed. It wasn't even something I thought about. It was pure instinct to prevent another man's cock from entering my mouth.

"Do as you're told, cuckold," Avery instructed. "Show me that I've trained you well. Show me that you understand what it means to be a good cuckold, Milo."

I pushed aside my instinct and opened my mouth. Lorenzo grabbed a handful of my hair and pushed his cock between my lips. I had a dick in my mouth. The head was surprisingly soft and the underside exceptionally stiff. I tried my best to keep my teeth away from it, though his thickness made that more difficult than I expected.

"Suck my cock," Lorenzo said.

It was a simple but hugely humiliating command, and one that I obeyed. I sucked his cock. I sucked the cock of the man that had become my wife's bull, that had fucked her better than I - or anyone else - had ever fucked her.

I had some help, too, as Lorenzo used his grip on my hair to fuck my face. He was fairly gentle - nothing like when he fucked Avery's face - but it was still a messy affair as I gagged, drooled, and spit up around his dick while my eyes watered.

Right as it began to feel like it was all just too much, Lorenzo pulled out and stuffed his dick into Avery's mouth. I wiped the mess of saliva from my face and watched my wife suck the dick that had just been in my mouth. A deep sense of humiliation coursed through me. It wasn't the first time I'd felt that - licking someone else's cum from your wife's pussy is humiliating, even if you're turned on by it - but I was surprised to feel my dick throbbing in my cage. I was turned on. I'd lost sight of that in the moment - in part because a face fucking is pretty miserable the first time you receive one - but I was actually turned on.

Lorenzo pulled out of Avery's mouth and remained still with the glistening head equidistant between the two of us. "Worship it together," he said.

This time, I didn't hesitate. I gave in immediately because I knew it's what Avery would have wanted and because I was turned on. I'd crossed another milestone in my cuckolding. I'd sucked cock. I'd crossed that bisexual boundary and I'd done so in a sloppy, exhausting, beautiful manner.

We licked and sucked Lorenzo's cock together. We took turns pleasuring the head and licking the shaft. We sucked his balls. We kissed over the plump head. We surrendered ourselves to doing what it took to make him feel good.

When he was satisfied, Lorenzo stepped back, helped Avery to her feet, grabbed her ass, and picked her up. "Put me inside her, cuck," he instructed.

I guided his cock into my wife's pussy and watched from below as Lorenzo fucked her in midair. She wrapped her legs around him with two hands on her ass he worked his cock in and out of her cunt.

The view from my knees was remarkable. It was unlike anything I'd witnessed as her cuckold. Her pussy was soaked with desire and his cock reached such incredible depths inside her with every thrust.

"Suck my balls," Lorenzo ordered.

I did so without hesitation. I'd surrendered to it at that point. I'd crossed the barrier into bisexual cuckold play and there was no point in hesitating anymore. I sucked his balls with wild abandon while Avery's ass dropped down onto my head over and over as Lorenzo used her pussy.

I sucked his balls right until he came inside her. I felt them jump in my mouth as his groans filled our living room. It was incredible. The whole thing was just incredible from start to finish.

Lorenzo lifted Avery off his cock and set her on the couch. He grabbed my hair and stuffed his dick into my mouth, using me to clean his shaft of any juices.

"Clean her pussy," he said when he was finished using me.

I turned to my wife, crawled between her legs, and cleaned her pussy. As I did, Lorenzo sat on the couch. He kissed her. He played with her tits in the dress. He reached between her legs and rubbed her clit while my tongue dove deep inside her to search for cum.

I swallowed everything he'd left inside her while Lorenzo gave her an orgasm, the first of four she'd experience that night. I was privileged to witness all of them, and as you might imagine, I did a fair bit of cocksucking that night. Once he'd pushed me past that barrier and into a full embrace of bisexual play, Lorenzo was determined to make sure I was comfortable staying there.

It was a big step for me, and one that Avery found quite enthralling, as she made clear in the days after my first encounter. I'm sure she'll talk about that, though.