The Cuckold Training Diaries - Part 5

Click here to read the previous parts of the story.

Avery

It was all going so well. Milo seemed to be taking to his cuckold training - at least the part before I actually thought about bringing another guy into our life - but I think I pushed a little too hard. I think I made him wait a little too long between orgasms, because he broke down and jerked off. He took his orgasm. He just couldn't hold off.

I know this because I walked in on it. I was supposed to be going out with a friend for lunch. In fact, I had gone out. But, I'd forgotten a gift I was going to give my friend so I had to come back home after getting halfway to the restaurant.

Milo didn't hear me come in. Want to know why? Because he was watching porn in the office and he had his headphones on. He was, in fact, just finishing up as I came home. I walked by the office and saw him literally cumming into a sock. He had that unmistakable orgasmic look on his face. Of course, it was quickly followed by a look of panic as he saw me standing in the doorway.

"I'm sorry," he said immediately. "I'm so sorry, Avery."

It's a cliché, but I wasn't angry. I was just crushingly disappointed. Milo had done the one thing I'd asked him not to do, and in doing so he'd shown weakness. It was deeply unattractive. "You should be sorry," I said. "But I have a lunch to get to, so we'll deal with this later."

I grabbed the gift and headed out of the house. Milo tried his best to clean up and catch up to me, but he didn't make it. He sent a handful of apologetic texts while I drove, but I didn't bother answering, even after getting to the restaurant. To be honest, I wanted him to stew in his sorrow a little. I wanted him to spend some time wondering whether or not I was furious and if I intended on punishing him.

I was frosty towards him for the next couple of days. It was, in a way, a form of punishment. I wanted him to be uncomfortable, to be remorseful, to understand that I was deeply disappointed, a fact that I reiterated countless times.

Then, after three days of frostiness towards Milo, my solution arrived in a nondescript cardboard box. I took it inside with a smile on my face, set it on the kitchen counter, and cut open the box. Inside was a black velvet bag that was cinched at the top with a delicate little rope. I untied that little rope and dumped the contents of the bag on the counter.

The sound of the pieces hitting the counter lured Milo into the kitchen and he stood there and stared for a few moments before saying, "What's that?"

I held up one of the pieces - the one shaped like a small cock - and said, "I think you know what it is, Milo." My voice was a little bit icy, as I was still in punishment mode.

Milo stepped into the kitchen and approached the counter. He didn't say a word as he stared at the clear plastic pieces of the chastity device I'd ordered for him. He knew what it was. Of course he knew what it was. He knew why I'd ordered it, too.

"Strip," I instructed.

That's when Milo snapped out of whatever trance he'd gotten lost in. That's when a panicked look came over his face. "Avery, I said I was sorry. I meant it. I won't do it again."

That's when I felt angry for the first time. It was a momentary feeling - there one moment and gone the next - but it was potent, and it was because he was lying. Not purposefully, but he was lying. He would absolutely cave to his desires again, even if he insisted he wouldn't. Of course he would.

"Yes, you will," I said after the anger had passed. "You can't help yourself, Milo. I don't even blame you. This is just how men are. I know I asked too much of you to go that long without having an orgasm, so now I'm going to remove the need for you to display willpower. It won't be permanent. You just need to wear it while I train you to be a good cuckold for me."

I saw excitement in his eyes, I presume at the mention of him being trained to be a good cuckold. I was tempted to push, to arouse him further, but I wanted him in the chastity device, and you can't put a hard cock in chastity.

"Now strip," I instructed. He hesitated again, so I added, "Milo, either you strip and let me put you in this chastity device or this whole thing ends right here and we never talk about your fantasy again."

He stripped. Of course he stripped. As I've learned, when a man has a sexual fantasy, he'll do just about anything if he thinks you're going to make that fantasy come true.

It took a little doing - he got half hard a few times as I handled his cock - but eventually I got Milo in the chastity device. I locked it up, I slipped the key into my pocket, and I smiled at how cute his cock looked in it.

"We're going out tonight," I said once he was locked up. "You're going to watch me flirt with another man."

"What?" he asked, though not because he couldn't hear me. Based on the look on his face, I think he was just sort of stunned at the idea.

"That's right," I said. "I'm going to get dressed up and we're going to go to a bar. You're going to watch guys try and buy me drinks. You're going to watch me let one or two of them do so. You're going to watch me flirt. You might even get to watch someone else touch me. What would you think of that, Milo?"

I'd read about chastity before buying the device, but I was still surprised at the look on Milo's face when he first felt the pain of getting turned on while locked up. Pleasure and discomfort seemed to be competing with each other for supremacy and there was something utterly delightful about watching that competition unfold.

Now that he was locked, there was no reason not to arouse him, so I pushed it. I leaned in, kissed his neck, and whispered, "Do you want to watch another man touch your wife, Milo? Do you want to see his hand on my knee, his fingers rubbing my inner thigh as he leans in to tell me how beautiful I look? Do you want to witness another man's desire to fuck your wife?"

Milo responded with a groan, probably because his cock was trying with all its might to get hard in the device that now encased it. There would be no erection for him, though. He'd failed to do the one thing I'd made clear he had to do. He'd surrendered to his lust and masturbated, and I knew that after he'd done it once he would do it again, for the allure of a great orgasm is something most men can't resist.

"I need to get ready," I said. "I need to make sure I look like someone worth trying to take home and fuck tonight. I want you to see lots of guys flirting with me, and I want a chance to flirt with someone I'd actually want to fuck."

With that, I walked away, leaving Milo naked and chastised in our kitchen.

Milo

Avery said we were going to a bar, but I would have called it a lounge. There were booths, tables with comfortable chairs, a small-ish area for dancing, and a long, elegant-looking bar. Most people there were around our age - she must have done her research to find the right place - and she was very clear that I was to find a booth where I could watch without it seeming like I was stalking her.

I entered first. I found a booth away from the bar - that's where Avery said she'd end up - and I ordered a strong drink the moment the waitress came over. Then I sat and waited. Ten minutes passed before Avery entered and she looked just as radiant as when I'd left her. Her hair looked long and wavy and it seemed to bounce a little with each step. She wore a simple-but-sexy little black dress that showed off enough cleavage to be intoxicating and ended just above her knee, letting her show off a good amount of thigh when she sat at the bar. The three inch heels were a nice touch, too, as they likely communicated to every man in the place that she'd put in a great deal of effort to look good.

I was turned on before Avery even sat down. She looked so hot, but it was more than that. This was the first time she'd worked to look good for another man. It wasn't a specific man in this case, but it was absolutely for another man. It was the first time I'd gotten a real taste of cuckolding, and even though it was a very mild taste, it was intoxicating.

There was something about the chastity device that made the arousal more potent. I'm not really sure why - perhaps knowing that I couldn't get hard was somehow arousing to me - but it felt more significant. It was strange and kind of wonderful at the same time, and it definitely had me in a crazily horny headspace.

Avery was at the bar for no more than a minute when a guy came up. He was overweight and dressed in a sloppy-looking suit - almost like he'd gotten pushed down a hill before coming to the bar - but he seemed to think he had a shot. I couldn't hear what she said, but he didn't look pissed after Avery rejected whatever pick up line he'd offered. I actually got a little worried, though, because there was no way Avery was going to enjoy her night if it was a steady stream of guys like that coming up to her.

Thankfully, the next guy was a lot better looking. I could tell his energy was all wrong for Avery, though. Even from afar it was clear he was the kind of guy that compensated for his insecurity with cockiness, acting as if Avery should feel lucky that he deigned to talk to her. She was the hottest woman at the bar, though, so there was no way she was falling for that, and of course she didn't. He looked a little bit annoyed as he walked away and back to his table of friends, most of whom seemed to be laughing at him.

It took a few more guys being rejected before one seemed to stick. This guy came up and sat next to her without saying a word. Avery looked his way and he smiled before signaling the bartender. He didn't seem to say a word to her, and yet he absolutely ordered two drinks, as the bartender quickly prepared them and set one in front of Avery and one in front of the guy.

Avery picked up the drink, turned towards him - giving me a great view of her legs, which she'd crossed, which exposed more of her thigh - and held up the glass. She took a sip, smiled at him, and he returned that smile with one of his own.

The rest of the bar - the world, really - disappeared as I watched my wife flirt with another man. I saw her do the things a woman does when she's into a guy. I saw her brush her hair behind her ear a few times. I saw her lean in to laugh at a joke and put a hand on his arm. I saw her run her finger over the rim of her glass as she flashed a flirty, slightly naughty smile at him.

At some point I felt my very first dose of cuckold angst. I didn't know that's what it was at the time, but it was powerful. I started paying more attention to the guy. I wondered if he was better looking than me, or if he was in better shape than I was. Then I wondered if he was a better kisser than me or if he had a bigger cock (he probably did). Each of those thoughts increased my sense of angst, though they were also accompanied by desire, which I now know is quite common for a cuckold, or would-be cuckold.

Then the guy touched her leg. The bar had gotten a little more crowded and there were people sitting on either side of them. It was louder and it seemed like they kept on leaning in to talk to each other. At one point he leaned in to say something and he put his hand on Avery's knee. When he leaned back, his hand stayed there. His thumb moved in small circles over her skin. She stared into his eyes and smiled before sipping her drink through the tiny little straw bartenders almost always give you. Then she offered a bright, beautiful smile, like she'd never been so happy.

The angst fell away for me. In its place was a stunning level of arousal. Not the kind that makes your dick hard as a rock, though. The kind that seems to rocket through your entire body. Head to toe. Like, every single part of you is somehow turned on in that way that leaves you tingling and almost instantly doubles your heart rate. It was the first time I'd ever felt that kind of arousal and it was intoxicating in every imaginable way. That, I think, was the moment where I truly knew that cuckolding was something I needed - truly needed - in my life.

Avery

His name was Carter. He was good-looking, confident, smart, and sexy. He was well-versed in how to charm a woman and he had no trouble charming me. The moment he put his hand on my leg is when I melted, though. He leaned in, told me I was astoundingly beautiful, and gently rested his hand on my knee. His thumb moved in small, slow circles over my skin and it was like he'd found a direct line to my pussy, as I could literally feel the wetness building between my legs.

His hand remained there as we continued talking. I wasn't going to move it - it felt so good - and he clearly had no intention of pulling it away. He did, however, find a way to move it just a little bit further up my leg every chance he got. He'd lean in to say something or I'd lean towards him to reply and he'd claim another sliver of real estate on my leg. Every time he did, I got a little more turned on.

Then he asked me to dance. A rare slow song - they seemed to play one every ten songs - came on. I didn't recognize it, but that didn't matter. I wanted to dance too. He took my hand and led me away from the bar and towards the other couples that were dancing. He put his hands on my waist and I put my arms up around his neck. I looked up into his eyes. Neither of us said a word. We just danced.

As we did, he pulled me closer, little by little until our bodies were pressed together. I felt an intense level of desire. My pussy was soaked. Truly soaked. I hadn't planned on going too far that night - I really did just want to flirt - but then he leaned down to kiss me.

I could have pulled away. I could have told him I wasn't ready for that. I was, though. I was more than ready. I wanted it. I was borderline desperate for it. So we kissed. We shared an electric kiss. His lips felt utterly perfect against mine. Our mouths were open, but there was no tongue, which felt right for kissing a relative stranger.

It was an astoundingly good kiss. So good that I actually moaned a little. So good that I felt him get hard. He smiled as he pulled back from the kiss and I couldn't help but smile back.

I initiated the second kiss. I moved my hand to the back of his head and applied just a little pressure to urge his lips towards mine. This time there was tongue, and it was hotter. Much hotter. His hands moved to the top of my ass and ventured south. He lightly squeezed the flesh and I moaned into his mouth again.

We danced and kissed for the rest of the song and then went back to our seats at the bar. We finished our drinks and chatted for another half hour. He asked for my number and I happily gave it to him. I was surprised he didn't ask me to go home with him - I would have turned him down, of course - but I was more than happy to let him text or call me. After all, I was planning on cuckolding Milo eventually, so there seemed to be no harm in having a potential man picked out for the occasion.

He kissed me again before leaving - it was yet another exceptionally good kiss - and I watched him walk out of the bar before heading towards Milo. He had a dumbfounded look on his face as I sat next to him. I put my hand on his leg and slid my fingers towards his crotch.

"You kissed him," he said.

I smiled and nodded as my fingers approached his locked cock.

"Was it...was it good?" he asked.

I nodded again before leaning in and kissing Milo's neck. I moaned as I grasped his locked cock through his pants. He moaned too - we were probably being a little too explicit for a bar - but I didn't really care. I'd accomplished what I wanted to do for the evening.

"I'm wet for him, Milo," I whispered. "I'm wet for him and I need to cum. I need you to eat my pussy. Will you do that for me?"

"Yes, yes, I'll do that for you," Milo answered.

I released his cock and slid out of the booth. "Let's go to the car," I said. "You can do it there."

That's exactly what he did, too. We left the bar, climbed in the backseat of the car, and I leaned against the door with my dress up around my waist as Milo ate my pussy until I had a huge, noisy orgasm while thinking about Carter.

We drove home afterwards and I had Milo eat my pussy again when we got back to the house. I didn't touch his locked cock. There was no point. It wasn't about his pleasure or even teasing him. It was about me and my pleasure. I think Milo enjoyed himself, though, at least based on the feverish manner with which he wet down on me.

It was an excellent night that felt like a preview of pleasures to come. It also cured my disappointment with Milo's weakness as I came away feeling like any future disappointments could be easily corrected. Plus, the pleasure to be had from cuckolding Milo felt like it would far outweigh any potential downsides, at least as far as I could see.