The Cuckold Training Diaries - Part 10

Click here to read the previous parts of the story.

Avery

"The groomsmen are awfully good-looking, aren't they?" I asked Milo as we waited for the bride and her father to walk down the aisle.

"What?" Milo replied, seemingly out of a sense of confusion more than anything else. He'd heard what I said.

"I mean, the suits certainly help - they're all exceptionally well-tailored - but it's not just the suits," I continued. "Chad's friends are all quite good-looking, aren't they? If any of them are single they're not going to have any trouble getting laid tonight."

I was whispering, of course - it wasn't the sort of conversation you typically had in a church - but I was in the mood to have a little fun, and perhaps to plant the seeds for having that same kind of fun at the reception. A wedding struck me as the perfect place to do a little cuckold training, as long as I could be a little bit discreet while doing it.

"Yeah, I guess you're right," Milo said.

I put a hand on his leg and let my fingers dance over his thigh as I leaned in and whispered, "If you had to pick one of the groomsmen for me to fuck, which would it be?"

I heard him suck in his breath in that way that sometimes happens when you're excited. I felt his thigh tense up a little, too, though I'm not sure if that was from arousal or a sense of panic because we were in a church and I was talking about fucking another guy.

"Avery, what are you doing?" he asked.

"A good cuckold should always be on the lookout for men for his wife to fuck, Milo," I said. "He should put her desires - and her pleasure - above his own at all times, and he should have a good sense of what kind of man she wants to fuck, what kind of man can satisfy her. There are six handsome men up there - not counting the groom - and I want you to tell me which you think would be best at fucking your wife."

I moved my hand towards his crotch and felt him tense up even more. It would have been fun to grope his cock in the middle of a church, but I didn't. I pulled my hand away before I even got halfway up his thigh and then I gave him a soft kiss on the cheek.

"Answer me, Milo," I said softly. "If I was going to cuckold you tonight, there's one man up there I'd pick over the others. There's one man up there that I'd absolutely love to have inside me by the end of the night. Let's see if you know my tastes well enough to pick the right man."

He was excited. He was even a little bit hard, at least based on the bulge in his pants. He liked the idea of me cuckolding him at the wedding. Of course he did, though.

I'd already picked out the guy I was most attracted to, though to be honest, they were all good-looking and I'm sure they all would have provided the kind of pleasure a woman would enjoy if she was on a mission to get fucked after a wedding. I wasn't on that mission - I didn't intend on cuckolding Milo that night - but it was a fun way to train him.

"The third from the left," Milo said.

I smiled. He was right. That was the guy I'd picked out too. He was a tall, handsome brunette with just a little bit of stubble - in that sexy, purposeful kind of way - and these really gorgeous blue eyes.

"Excellent choice," I whispered. "He's the one I would have picked, too."

Milo turned and looked at me with this wonderful sense of lust in his eyes. It's a look I'd really only seen since I informed him that I would be training him to be a perfect cuckold. It's the look that always lets me know that he's more turned on by cuckolding than literally anything else, and thus it's a look that I've come to love.

"You'd enjoy it if I fucked him tonight, wouldn't you?" I said softly.

"Yes," Milo admitted.

I smiled, and then I considered if I actually wanted to cuckold my husband at a friend's wedding. The reception was going to be held at a hotel. Assuming the groomsman was actually interested in me, it would have been as simple as going up to his room for a good fucking. And, since I was fairly certain that particular groomsman had come from out of town, it seemed like the least complicated way to cuckold Milo for the first time.

"Are you certain you'd enjoy that, Milo? Are you certain you'd actually enjoy it if that man standing up there fucked me tonight? If his cock filled my pussy over and over? If I came all over his cock? If he came while his cock was buried inside my pussy?" I asked as I got increasingly turned on at the idea of fucking the handsome brunette guy standing with the other groomsmen.

"Yes," Milo answered.

Our conversation would have continued, but the string quartet played the bride's song of choice and everyone stood up. We all turned to watch as Ella walked down the aisle with her father. As she walked by us I turned to glance between Milo's legs and saw a little bit of a bulge. He was still turned on. Of course, I was turned on too. It's not like Milo was the only one to benefit from his fantasy, after all. I'd benefit too if I actually decided to cuckold him.

I managed to stay quiet during the ceremony. I wanted to keep teasing Milo, but it seemed incredibly rude to do so. I thought about it, though. I really did. I kept checking the groomsman out, and there were a few instances where he looked my way. I didn't look away on either occasion. In fact, I smiled at him both times and he smiled back. I got the distinct feeling that he'd be up for it if I wanted to let him take me to his room after - or during, I suppose - the reception.

After the vows and the couple sharing a surprisingly long kiss, the bridal party made their way down the aisle and out of the church as we all stood. Much to my delight, the groomsman I'd been staring at turned and smiled at me - and smiled in a flirty manner - as he walked by.

"Did you see that?" I asked Milo. "Did you see him smile at me?"

"I did," Milo answered.

"He saw me smiling at him during the ceremony," I said as I took my husband's hand. "I think he got the message."

"What...what message?" Milo asked.

The bridal party was out of the church by that point so I turned to Milo, smiled, and leaned in to kiss him on the cheek before I whispered, "That I want to fuck him."

Milo moaned. It was a quiet moan, but he absolutely moaned.

"I could cuckold you tonight, Milo," I said. "I could cuckold you for the first time. I could cuckold you as soon as we get to the hotel, in fact. I'm sure that handsome groomsman wouldn't mind being a little late to the reception. Is that what you want?"

"Yes," Milo said.

"And are you sure you could actually handle it, Milo? Or would you go out of your mind with jealousy? Would you be overwhelmed with angst as you sat in the ballroom and wondered about what your wife was doing in another man's hotel room? Would you wonder if it was going terribly, or if it was going so well that I'd come down and decide that I no longer had any interest in being married to a cuckold?" I asked.

"Is that possible?" Milo replied.

I caressed his face and kissed him softly on the lips. "It's not likely, but anything is possible, Milo." That's the truth, too. Anything is possible when you introduce another man to your marriage, and to pretend otherwise is irresponsible. I had no intention of that happening, of course, and there was really no chance of a one night fuck breaking up my marriage. I mean, I love Milo dearly.

My question seemed to unmoor him a little, though, to the point that he actually took some time to think about it. "I don't want to lose you, Avery. That's the last thing I want. But...but..."

"But you want me to cuckold you," I said. We were nearly alone in the church at that point and it was time to get going.

"Yes," he admitted.

"Well, let's go to the reception and let's see what kind of trouble I can get into," I said.

I hadn't decided what I was going to do at that point, in part because I had no idea what the handsome groomsman was actually like. I only knew that I was physically attracted to him and that the idea of cuckolding Milo with him made my pussy wet. Either way, though, I was fairly certain I was going to have a damn good time at the reception.

Milo

I thought that Avery was just teasing me when she talked about fucking the groomsman. She'd spent months doing that very thing, after all. Even the messaging and phone calls with Alonso were forms of teasing, as they drove me absolutely wild with desire and Avery wasn't actually fucking someone else.

Before the reception - while the bridal party was busy with the photographer - we had cocktails and chatted with our friends. Avery seemed to get a little flirtier as she finished her cocktail and started to feel the effects of the alcohol. Of course, I love the flirty version of my wife, and given that I was the one she was doing most of the flirting with I was really quite excited. Plus, she looked really good in her dress.

Once the photos were finished we all went into the ballroom and found our tables. We chatted a little with the people we were seated with and then Avery excused herself. I figured she was going to the bathroom, but she headed right for the bride and groom. She spent a few minutes talking to them and then I figured she'd come back to the table. She didn't, though. Instead, she introduced herself to the groomsman she'd been smiling at during the ceremony. The one she was apparently considering fucking that night.

They talked for a few minutes and while it was hard to tell, I'm pretty sure she was flirting with him. There was laughter and a little bit of touching and there were two instances where she bent over - she was standing and he was sitting at the table - and absolutely showed off her cleavage, and he absolutely looked, which is what Avery wanted. Of course it's what she wanted.

I watched him as she headed back to our table, and he didn't take his eyes off of her the entire way. He was enamored, and with good reason. Avery was beautiful and had just showed considerable interest in him, and what guy isn't enamored with a beautiful girl that seems to want him?

"Were you flirting?" I asked as she sat down and leaned into me.

"I was," Avery replied. "Heavily, in fact." She scooted her chair a little closer to mine and quietly asked, "You don't mind, do you? I mean, you want me to fuck another man, don't you? You want to be my cuckold, right?"

Honestly, I was a little bit on the fence. Before she asked those questions, that is. All she had to do was utter those words in that particular order and I was on board, mostly because I felt this intense surge of lust, and when I feel that kind of desire I can't resist it. I'm sure all you cuckolds out there know what I'm talking about.

"Yes, I want to be your cuckold," I said.

Avery put her and on my leg, kissed me on the cheek, and then smiled softly. "His name is Asher, by the way. So if he ends up taking me up to his room tonight, that's the name I'll be screaming while his cock is buried deep in my wet pussy."

That line got me hard. Rock hard, in fact. But of course it did. I don't think I've mentioned yet that I'd gone nearly two weeks without an orgasm by that point, so I was feeling desperately horny.

"You're a goddess," I said. "You really are."

"I know," she replied softly before her lips found mine for a gentle kiss.

I'm not sure what our table mates thought as Avery and I basically made out with each other, but I didn't really care. Thankfully, we were talking too softly for them to hear us, so they probably just thought we were being a little too open with our affections, but I was in a place where I did not give a damn about anything other than Avery potentially cuckolding me that night.

For the most part the reception unfolded like most wedding receptions tend to unfold. There was the first dance between the couple, the toasts from the best man and the maid of honor, the cutting of the cake, the dinner being served, etc. Throughout all of that, though, there was Avery silently flirting with Asher. Mostly it was the two of them looking at each other and exchanging smiles and the occasional lusty stare, but that was more than enough to keep me in a place of near constant excitement.

The moment the party opened up to everyone getting on the dance floor - after dinner and cake - Asher made a beeline for our table. His eyes were fixed on Avery the entire time, too, making it perfectly clear to anyone paying attention that he was interested in her.

"Would you like to dance?" he asked while offering his hand.

Avery smiled, took his hand, and walked away with the handsome groomsman. Now, you have to keep in mind that we were at a friend's wedding and we knew quite a few people there, so the dancing wasn't anywhere near as intimate as it could have been. It was still pretty intimate, though. It's not like they were dancing in the manner that a pair of friends would dance.

As you might imagine, they had my full attention. I watched as if we were the only three people in the ballroom. I noticed the way his hand moved down her back and to her waist. I noticed how it moved just a little further south so he was touching her ass just a little bit. I noticed how that seemed to put a smile on Avery's face, and how she looked up at him with just a touch of lust in her eyes.

The longer the song went on - it was the kind you slow dance to - the closer they got and the more intimate they seemed. The dance floor was pretty crowded so it was likely not many people even noticed them, but I noticed every bit of it, of course. I noticed the way he held her waist with both hands to pull her closer. I noticed the way she put her arms up around the back of his neck. I noticed the way their bodies were suddenly pressed quite close together. I could have been imagining things, but I'm fairly certain Avery wanted to kiss him by the time the song came to a close.

They danced together for three more songs - all of which were upbeat - and as I watched it felt a lot like Avery had gone to the wedding with an entirely different man as her date, like I was just the third wheel. Of course, I found that rather pleasurable, so I had no objection to the notion.

Eventually he leaned in, said something to Avery, and took her hand as they walked off the dance floor and towards the bar. I wasn't sure what to do, but it would have been awkward to join them as a genuine third wheel, so I sat at the table and watched from afar as another man got my wife a drink and chatted her up.

There was a point in the conversation where they both looked over at me. It was impossible to know why, but I assumed that they'd broached the subject of Avery being a married woman, which I also assumed meant they'd broached the subject of having sex.

Another slow song came on right as they were finishing their drink and Asher took Avery's hand so they could join all the other couples. This time they were exceptionally close from the start. Avery looked up into his eyes as his hands moved to her lower back and then gently grasped the top of her ass to pull her close. She smiled as their lips came exceptionally close together. It would have been obvious to anyone watching that Avery was being inappropriately intimate with another man, and yet I honestly couldn't bring myself to give a damn about that. I was rock hard watching them dance, and rock hard as I thought about what might happen as a result of the obvious intimacy between them.

They parted ways after the dance and Avery came towards our table. She bent over and whispered, "Follow me," and I got up and did as my wife desired. She led me out of the ballroom, down the hallway, and into a remarkably luxurious bathroom. Once we were inside Avery locked the door and gently pushed me up against it.

She didn't say a word as her hand moved down my chest and between my legs. She grasped my cock and stroked me slowly while holding my gaze. Her lips slowly neared mine and she offered a remarkably soft, seductive kiss.

"Do you want me to cuckold you?" she asked softly.

"Yes, please," I replied.

"Tonight?" she asked.

"Yes, Avery, I want you to cuckold me," I said.

Avery released my cock, stepped back, and leaned against the wall. She reached down to lift the bottom of her dress, pulled her panties aside, and said, "A cuckold should prepare his wife's pussy for another man's cock, so if you want me to cuckold you, you should get on your knees and eat my pussy."

I dropped to my knees immediately. I crawled closer. I looked up at my beautiful wife and then leaned in and devoured her pussy.

"Don't lick my clit," she corrected me. "You're not trying to make me cum. Your job is to get me wet for his cock, to make it easy for him to slide into your wife's pussy. It's his job to make me cum. It's his name I'll be screaming as I orgasm on his big dick. Now put your tongue inside me and make sure I'm soaked when I cuckold you."

I moaned as I did what she desired. I was so turned on I felt like I was going a little bit out of my mind. It was so hot. Avery put a hand on the back of my head as I continued to tongue fuck her pussy to leave her completely soaked.

I honestly wasn't sure if she was going to cuckold me. After all, she'd done quite a lot of teasing. This might have been more of that, or just a training exercise of some kind. I didn't really care, though. I was immersed in pleasure and I was more than happy to stay in that place for as long as possible.

Eventually, though, Avery pushed my head out from between her legs, pulled her panties over her pussy, and let the bottom of her dress fall. "Thank you," she said before bending over and kissing me softly. She smiled, licked her lips, and added. "Mmm, I taste good."

"Yes, you do," I answered.

"Stay in here for a few minutes," Avery said as she stepped around me and reached for the door.

"Are you going to cuckold me?" I asked.

Avery unlocked the door and left without saying a word. I stood and pulled out my phone to set a timer for three minutes. I paced around the bathroom as I wondered if she was going to cuckold me. I wanted her to, and yet the idea made me anxious.

The timer went off and I slipped my phone into my pocket and left the bathroom. I made my way back towards the ballroom and I was about to step inside when I noticed a woman in a dress that looked a lot like Avery's standing near the elevators all the way across the lobby. She was holding hands with a man. I rushed to get a closer look as the elevator doors opened. The woman and the guy stepped inside, turned to each other, and shared a shockingly passionate kiss. It was Avery and Asher. She was going up to his room. She was going to cuckold me. She was going to fuck another man. It was happening.

The elevator doors closed and I stood there and listened to the sound of my heart pounding. My knees felt weak and I experienced a breathtaking array of emotions that shifted from one second to the next. It was happening. There was nothing I could do to stop it. I didn't know what room he was staying in. I didn't have a way to get in. I was about to be cuckolded. My wife was about to fuck another man.