The Cuckold Training Diaries - Part 2

Click here to read the first part of the story.

Avery

The orgasm control was intended to do two things. First, I wanted to keep Milo in a state of arousal, because everything I'd read said that when a man is in that state of arousal he's a lot easier to train. When he cums, every bit of interest he had in his fantasy goes away and it can take a few days for him to get back to that place of arousal. Second, I truly wanted him to shift his focus to my pleasure, because at its core that's what cuckolding is about. It should be a mutually pleasurable thing, but it starts with my pleasure - as Milo said, if I'm not enjoying the sex, then he's not going to enjoy his cuckolding - and so I wanted him to actually focus on that, and orgasm control is a great way to get him to focus on that.

Milo actually gave me two orgasms that first day on the couch. After twenty minutes of foot rubbing I took my leggings off and let him crawl between my legs. He went down on me with great vigor, but I actually had him slow down. I told him I wanted it to feel like he was worshiping my pussy, a notion that he really seemed to enjoy. He really did worship me, too, and really put his tongue to work. He even used his fingers to great effect.

After my first orgasm I told him to stay between my legs and kiss my thighs and labia. I told him to put his tongue inside me for a little, to taste my juices. Then, when I'd recovered, I told him he could worship my pussy once more and give me a second orgasm. He went for it, of course. It took longer the second time - I think his jaw was actually sore by the time we were done - but he put in a great effort. He was between my legs for nearly 45 minutes, and I'm pretty sure he was hard the whole time, which was amazing.

The next morning, I woke Milo up with a handjob. I slipped my fingers into his underwear, took his cock in my hand, and stroked him until he was hard as a rock. He woke up about halfway through and he had this giddy smile on his face. I could tell he'd forgotten all about the little rule I'd established, because he absolutely expected that I was going to make him cum.

"Did you forget about your task?" I asked as I pulled my hand from his underwear. "You need to make me cum ten times before you're allowed to have an orgasm, Milo." He looked a little frustrated, which I actually kind of liked. I wanted him a little frustrated. I wanted to see if he'd follow my rule despite his frustration. "I never said your training would be all pleasure, but if you want me to fuck another man, Milo, you're going to have to make it through your cuckold training."

That seemed to wipe away some of his frustration as I saw a smile cross his face. I took note. If a small reminder of the ultimate goal here - of Milo getting to be a cuckold - was all it took to bring him back to a happy, centered place, that was certainly something I could do with ease.

Milo then took the initiative. He rolled towards me and kissed my neck as he ran his fingers under my shirt. I don't wear a bra at night, so he found my breasts and gently played with my nipples in the way he knows I love.

"I can't stop thinking about you cuckolding me," he said before pressing his crotch into me and rubbing his stiff dick over my leg, likely generating a bit of pleasure via friction.

I moaned, mostly because he'd lifted my shirt and was now gently sucking on my nipple, but also because moaning while he talked about his fantasy seemed like a good way to turn him on just a little bit more. "It's okay if you think about it," I said softly. "Just don't masturbate while you think about it. Remember, I control your orgasms now and I won't be happy if you break the rule and decide to jerk off on your own."

"I won't," Milo said before kissing his way down my stomach and pulling off the boyshort panties I'd slept in. "I promise, Avery, I won't."

I reached down, put a hand on his head, and applied gentle pressure to guide him to my pussy. His tongue found my clit and I arched my back a little as he began to gently massage it, just like he'd done the day before. I loved that he'd remembered my instructions to act as if he was worshiping my pussy, and it even felt like his technique had improved a little, like he was genuinely focused on my pleasure without any consideration for his own.

"If I can train you to be a good cuckold, Milo, I will fuck another man," I said. It felt good to indulge in a little bit of dirty talk related to his fantasy, and to actually give voice to the potential future we were working towards. In truth, I was actually kind of excited about the idea of getting to have sex with someone else. I was nervous about it too, but I'm not a prude. I was with a decent number of guys before Milo - and I love sex - so the idea of getting to meet someone new, and to pick someone solely for their ability to fuck me well, was actually really exciting.

After my comment, Milo looked up as he rubbed my clit with his thumb. "Really?" he asked.

The hope in his eyes was actually kind of adorable. "Yes, Milo. If you let me train you to be a good cuckold - to be the kind of man that can emotionally handle his wife fucking someone else and loving the pleasure that other man gives her - then I will absolutely welcome someone else into my pussy."

He loved the dirty talk. It wasn't heavy or particularly explicit, but it was just dirty enough to get him overwhelmingly excited. Again, I took note, for it seemed that Milo's cuckold fantasy was the quickest way to excite him, and I expected that his training would involve lots of difficult moments where he would need to be brought back to a place of focus, and if I could do that with a little bit of dirty talk, that would be exceptionally helpful.

I then put a hand on his head and pulled his mouth back between my legs. He moaned before putting his tongue to work once more and it wasn't long before Milo had given me an orgasm. When I'd finished cumming I urged him to crawl forward and lie on top of me. I kissed him - with lots of sensual tongue play - and grabbed his ass. I moved my hips - kind of like I was dry humping him despite being on my back - and I felt his stiff cock pressing into my pelvis.

I wondered if he could feel my wetness, if it was enough to turn him on and make him think about how good it would feel to fuck me. I was absolutely trying to drive him a little bit crazy with desire, for I'd decided that getting him wildly turned on as often as possible was going to be the best way to train him.

"Do you want me?" I asked.

"Desperately," he answered.

"Seven more orgasms and you can have me," I replied with a smile. I released his ass and gently pushed him off of me. Milo rolled onto his back and I looked his way and smiled. I acted like I was going to roll over and continue fooling around with him, only to get out of bed and head for the bathroom. "We should get up," I said as I looked back to see his stiff dick pointing towards the ceiling. "We can't spend the whole day in bed, after all."

Milo groaned and I smiled. As it turned out, I liked being in control of his orgasms and I liked teasing him. It had me excited to try more of it.

Milo

I made Avery cum three times in the first 12 hours, so I figured the rest of the orgasms would come pretty quickly. She had other plans, though. Instead of letting me make her cum whenever I felt like it - which was basically all the time - Avery ended up refusing me more often than not. She would, however, make an effort to turn me on pretty much every time I asked to get her off or tried to turn her on so she'd let me go down on her or use my fingers. If she said no she'd inevitably give me the kind of kiss that would bring my cock to life, or she'd whisper something dirty about cuckolding me into my ear, then suck on my earlobe a little. It was almost never enough to get me fully hard and crazed with lust, but it was always enough to keep me in a low level state of arousal.

That was the point, of course. At least, now I know that. She wanted to drive me crazy. She wanted me in that mental place where even the slightest thought of cuckolding was enough to get me all kinds of worked up. She certainly succeeded at that, as I was very quickly in a mental space where I couldn't stop thinking about it.

Sixteen days passed between me giving Avery the first and the ninth orgasm. I'd gone more than two weeks without cumming, which was probably the longest I'd gone in my life (since I started cumming, that is) up to that point. I was desperate, as you might imagine, especially since Avery put a fair amount of effort into keeping me desperate by turning me on with great frequency. She started doing so even more often as the days went by, in a successful attempt to increase my desperation.

Then, she offered a proposition. I was in bed and Avery was in the bathroom finishing getting ready for sleep. It was a little after 11 p.m. I was thinking about my chances of giving her that tenth orgasm and strategizing how I wanted to approach it. Should I start with soft kisses and gentle touches? Should I just try and kiss my way down her body to get between her legs?

The bathroom door opened and she stepped into the bedroom in a stunningly sexy lingerie set consisting of a red lace bra and panties, a garter belt, a pair of fishnet stockings, and high heels that made her legs look impossibly long. I sat up and stared as Avery approached the bed with a naughty smile on her face and an irresistible sway in her hips.

"I had an idea," she said before pulling back the covers and crawling into the bed. She stopped between my legs and ran her fingers up my thighs before grasping my cock through my underwear. "You've made me cum nine times. You're one more away from getting to have your orgasm."

I was already hard. She looked so good and her touch felt spectacular. I couldn't help but get hard.

"I was thinking that you could fuck me to the tenth orgasm," she said.

"Yes," I replied. "Please. Yes. I want that."

She pulled my underwear off and tossed them across the room as a devilish smile crossed her lips. "You didn't hear the rest of my proposition." She stroked my cock and then leaned down, wrapped her lips around the tip, and swirled her tongue over the head as she soaked up the precum that had leaked out of me. "If you cum before I do, you'll have failed to complete the task I gave you, and failure will have to be punished. If I cum before you, then you'll have completed your task, and I'll reward you by letting you fuck me again tomorrow."

"What...what's the punishment?" I asked. "If I fail, I mean."

Avery smiled again and she looked truly delighted with whatever idea she'd come up with. "You'll have to give me 20 orgasms before you get your next one. And, I'll be teasing you even more. It turns out that I really, really like teasing you. It turns me on, and I like feeling turned on."

"If we don't have sex...if I just make you cum some other way, how long will I have to wait for my orgasm?" I asked.

Avery took my cock in her mouth again. This time she swallowed me and it was like arousal enveloped the entirety of my body, making it impossible for me to think straight. She held me in her mouth for a few seconds and then looked up and said, "I don't know. After all, I'd really like to fuck my husband tonight, so if you choose not to fuck me and to make me cum with your tongue instead, I might be disappointed enough that you'll have to wait quite a while."

I couldn't wait. I just couldn't. I couldn't go another day. "Let's have sex. I can last long enough to make you cum."

Avery smiled and kissed her way up my chest. She straddled me with my cock resting against her panties and reached up to play with her breasts in the lace bra. "Do you like my lingerie?" she asked.

I nodded. "It's so sexy."

"I bought it just for you," she said before reaching down and grabbed my cock. She rubbed the tip against her panties and I felt the warmth and wetness emanating from her pussy. "I did a little flirting at the store, though."

My eyes shot open as excitement rushed through my body. "Really?"

Avery bit her lower lip, nodded, pulled aside her panties, and rubbed the head of my stiff cock over her pussy lips. "There was a guy shopping for his girlfriend. He was tall, good-looking, muscular. The sort of man that has no trouble attracting women. I had this lovely little lingerie set in my hand and I held it up against my body to try and get a feel for how it would look. He told me I'd look incredible in it, that my husband was a lucky man."

"What...what did you do?" I asked.

Avery took my cock inside her, moaned, and put her hands on my chest as a smile crossed her face once more. She dragged her hips forward, bathing my cock in the slick heat of her pussy and offering me an astonishing level of pleasure. "I told him that his girlfriend was a lucky woman, for she had a gorgeous, generous man that was buying her lingerie because he wanted her to feel sexy."

The thought of Avery openly flirting with another man - and telling a guy he's good-looking is unquestionably flirting - it made my cock tingle with pleasure. It was just so exciting.

"He said he'd be willing to help me find the right lingerie set for you," Avery continued as she looked into my eyes and then leaned down and kissed my neck while slowly moving her pussy over my cock. She moaned and then softly said, "I asked him if he'd be willing to let me model this naughty little red lace bra and panty set for him."

I actually felt my cock get stiffer inside her. I didn't think I could get any harder than I was, but it turns out I could, and with that excess stiffness came an increased sense of pleasure. Suddenly, Avery's pussy felt even better around my cock. Every movement of her hips brought with it just a little more pleasure.

"Did you...did you model it for him?" I asked.

Avery started to ride me a little faster. Her breathing was heavier. It seemed like she was getting closer to her orgasm. I just had to hold out a little longer.

"I did," she said. "I strutted down the fitting area hallway like I was a lingerie model on the catwalk. His eyes devoured me, Milo. He had a girlfriend, but I could see that he wanted me. I could see that he wanted me badly. He didn't have to say a word. I knew the lingerie looked good."

That moment, when she confirmed that she'd modeled her lingerie for another man, was the hottest of my life, up to that point, at least. The fact that I was inside her certainly helped with that, but I'm honestly not sure I've ever felt so turned on.

"You know what else?" Avery asked softly.

I groaned as she began to bounce her pussy up and down on my cock, filling the bedroom with the sounds of her incredible wetness. "What?" I replied.

"I could see that his cock had grown, Milo," she said. "He'd gotten just a little bit hard for me, for your wife. And you know what? He was bigger than you. I could see it even through his pants. He was much bigger than you."

She sat up, put her hands on my chest, and smiled as she continued to ride me vigorously with her pussy. She wore a look of utter joy on her face, as if she was having the time of her life talking about this guy from the lingerie store.

"You know what else?" Avery asked before smiling seductively and leaning a little closer. "I wish it was his big cock inside me right now."

I came instantly. I came hard. Really hard. I felt my whole body shudder. My toes curled. I saw stars for a few moments and I felt a little lightheaded. It was the best orgasm of my life. Hands down.

Avery's pussy remained wrapped around my cock as she lowered her lips to mine and we shared a kiss. "It's a shame you couldn't hold out a little longer," she said. "I was close. Now you're going to have to make me cum 20 times before I let you cum again. That could take a month, Milo."

"It was worth it," I said. In hindsight, that probably wasn't true, but in the moment it absolutely felt like it was worth it.

Avery smiled and kissed me again, this time offering a hint of tongue that felt thrilling.

In the aftermath of my orgasm, I couldn't help but wonder if she'd perhaps made up a story to try and coax me into an orgasm before she climaxed, so I asked. "Did any of that actually happen? With the lingerie shopping, I mean?"

Avery sat up and smiled. "There was a hot guy there. He was probably shopping for a girlfriend because he wasn't wearing a wedding ring. He smiled at me a few times and he definitely checked me out. We didn't flirt, though, and I didn't model the lingerie for him. Thinking about it was a turn on, though, and I'm absolutely certain that someone as tall as he was had a big cock, and when - or if, I should say - I do cuckold you, I'll definitely be doing it with someone with a big cock, so I only lied a little bit.

"I love you," I said. How could I not have loved her in that moment? I mean, she came up with a dirty little story that made sure I had a world class orgasm. What's not to love about that?

"I was, in fact, thinking about him while you were inside me," she said. "And I'd like to cum. Would you like to tick off the first orgasm on your new list, or should I do it myself?"

"I'll do it," I said as I marveled at the idea that she’d actually indulged in a little fantasy about another guy.

Avery lifted her pussy off my cock, rolled onto the bed, and spread her legs. She unhooked her bra to free her breasts and I rolled over and took a nipple into my mouth as I reached into her panties to rub her clit. It was a little messy down there, but I didn't mind. I was still riding high in the aftermath of my orgasm and I was happy to do whatever it took to make Avery feel anywhere near as good as she made me feel.