The Cuckold Training Diaries - Part 3

Click here to read the previous parts of the story.

Avery

I don't know how often you cum, but twenty orgasms is a lot for me. Life is busy, after all, and I'm not always in the mood to have sex, or have Milo go down on me, or even to masturbate. Of course, I don't always have a husband that's not allowed to cum until he gives me twenty orgasms, which certainly changes the equation a bit.

Milo changed after he came inside me, but of course he did. That desperate energy that had built up over the course of a few weeks while he'd been denied orgasm was completely gone. The change did serve to reinforce what I'd assumed, that it would be far easier to train him if he was in a constant state of desire. That's why I didn't bother teasing him or trying to fool around with him for the first few days. He needed to build up that desire again before we could have fun.

On the third day I didn't bother putting on anything other than a t-shirt when I got out of bed. I strode into the kitchen in the panties I'd worn to bed - a nice thong - and that t-shirt, which happened to be short enough to show off my belly button, which was the first thing Milo looked at when he saw me.

"Good morning," I said before approaching him at the kitchen table and leaning over to offer a soft kiss.

"Good morning," he replied after my lips lingered against his for a few seconds.

I poured myself a cup of coffee, stirred in just a splash of half and half, and then lifted myself onto the kitchen counter. Milo turned his chair to face me and I sipped my coffee and stared at him over the rim of the mug for a few seconds before asking, "When you say you want me to have great sex with someone else, what do you mean?"

Milo seemed a little surprised by the question - or perhaps the introduction of his fantasy so early in the morning - but eventually he found his way to offering an answer. "I mean the kind of sex that leaves you a little lightheaded when it's done. It lingers in your memory. You find yourself thinking about it constantly. You want more of it just a few minutes after it's over because it made such an impression on you. You want to tell your friends about it because it was so good that you can't help but want to let the world know about it."

It was a good answer, since that's largely what great sex is to me. It's not the kind of thing a person has all that often, either. I'm not sure it's the kind of sex you can have with someone you've been with for years, though perhaps that's not true and I've just been with a man who's not really capable of offering great sex all that often.

"And you want me to have that kind of sex with another man?" I asked. "You want me to have the kind of sex that I can't stop thinking about, that I want more of, that my body craves."

I saw the arousal on Milo's face. It was unmistakable, and yet another indicator of just how potent his fantasy was. At that point I knew that I still didn't understand the depths of his desire, but I learned a little more every time I witnessed his arousal, especially at something as simple as a question.

"Yes, Avery, I want you to have that kind of sex with another man," he answered. "It's just...I don't know, it's just so hot to me."

"You don't worry?" I asked, in no small part because I couldn't help but worry a little about how having that great sex with someone else might impact our marriage.

"About what?" he replied.

I sipped my coffee, smiled, and said, "About how our marriage might change if someone else fucks me better than you do. What if he fucks me so good that you just don't compare, Milo? What if I find a man that's capable of leaving me lightheaded, and making my toes curl, and making me scream his name because the pleasure of his cock inside me is just so overwhelming?"

Miles got up and came towards me with a bulge in his shorts. I sipped my coffee - preventing him from leaning in for a kiss - and he smiled and reached out to run his fingers down my back before grasping my ass and pulling me towards the edge of the counter. He then dropped to his knees, looked up at me, and asked, "Can I make you cum?"

"You may," I replied. It was a small thing, but I actually got turned on when he asked permission. He didn't answer my question, but in truth, I wasn't asking the question hoping for a real answer. I was asking because I wanted to see how Milo would react. After all, if I'm going to go to the effort of cuckolding my husband, I'm not going to do it with a man that's worse than him in bed. I'm going to do it with someone that's better. What would be the point of doing it any other way? Milo's reaction made it seem like he was turned on at the idea, and the fervent nature of his pussy eating only deepened my conviction that he was aroused, which was a very good thing.

I was in no rush to cum, so I let Milo work for a while. I liked seeing him on his knees. I liked the way he'd look up at me with eyes so full of desire, with his eagerness to do get me off. I liked feeling that pleasure, too, as Milo is very good with his tongue.

Eventually, I set my coffee cup down, put a hand on the back of his head, and had a particularly loud orgasm. "Thank you," I said afterwards. "And that's one. Only nineteen more to go before you get to cum again."

When he stood up, Milo had a full on erection, a sight that put a smile on my face. I reached up and stroked it through his shorts and he smiled. When I sped up my strokes, Milo grabbed the counter to steady his balance and he moaned, as it seemed to feel quite good.

"It's already been three days, and you've only made me cum once," I said. "At this rate, it will be two months before you're allowed to cum again, Milo. Can you last that long?"

"No," he replied. "I'll have to make you cum more often."

I kissed him. He moaned as I unzipped his shorts, pulled out his cock, and stroked him while our tongues mingled just a little. It had taken three days, but I was confident that Milo was back to that place of desire where he could be trained. Now I had the time it took for him to give me nineteen orgasms to probe his desires to be a cuckold and to see how far he was willing to go to make those desires a reality.

Milo

After two weeks, I'd only provided Avery with six orgasms. I was fourteen away from getting to cum again and I was already in that desperate place that guys sometimes arrive at when they're pent up. Then Avery figured out a way to make it a little bit worse.

It began after dinner. I cooked - steaks on the grill - and we shared a bottle of wine both during and after dinner. We ate on the deck and watched the sun go down while sipping our wine and enjoying each other's company.

After finishing her second glass of wine, Avery set it aside, stood, and straddled me. I put my hands on her waist and looked up to see a smile on her face. A moment later she began to move her hips back and forth over my crotch. Her movements were slow and deliberate, but they succeeded in getting me hard, as two weeks without an orgasm had left me in a near constant state of desire. My hands wandered under her shirt and up her torso until I had her breasts - through a lovely lace bra - in my grasp.

"Wine always makes me so horny," Avery said softly.

She was right about that. Wine and champagne tended to do that for her, more so than any other alcohol. She'd easily transferred her desire to me, as I was rapidly approaching a state of all-out, desperate lust.

Avery smile, leaned down, and kissed me. I slipped my fingers into one of her bra cups to play with her nipple and she moaned into my mouth while moving her hips rapidly over my crotch, generating heat and desire along with a painfully throbbing erection and more than a little precum.

"Let's go to the bedroom," Avery said as she stood up and took my hand.

She pulled me into the house and to our bedroom. We kissed and stripped each other naked. I slipped two fingers into her pussy as she took hold of my cock and stroked me slowly while sucking on my tongue in a manner I found irresistible. It was the kind of foreplay we usually enjoyed before having sex, which is why I was suddenly quite convinced that Avery was going to forget all about my need to make her cum twenty times before I got to orgasm again. I figured the wine had left her brain a little bit foggy and that she was going to abandon that and let me fuck her.

I was wrong, of course.

"It's a shame you can't fuck me," she said softly. "I'd enjoy feeling your cock inside me, but I think we both know that after two weeks you wouldn't be able to last very long, would you?"

"I could last," I said. I wasn't really thinking, though. Looking back, I'm certain that I would have cum inside her if she'd let me fuck her. Of course I would have. Once I'd felt her pussy I wouldn't have been able to stop.

She chuckled softly at my declaration. "No, you couldn't," she said. "It's cute that you think you could, though. It shows how desperate you are, and I like it when you're desperate."

With that, Avery turned and crawled into the bed. While on her hands and knees she looked over her shoulder, smiled, and wiggled her ass. All I could think about was climbing into the bed and fucking her from behind - that would have felt spectacularly good - but I restrained myself. After a little teasing, Avery rolled onto her back, spread her legs, and reached down to play with her pussy as I watched.

"Mmm, I'm so wet," she said. "And I'm so horny, baby."

She closed her eyes, moaned, and arched her back. She took one of her breasts in her hand while fingering her pussy and I stood and watched with my mouth hanging open like I'd never seen anything so beautiful. It took work to keep my hands at my sides instead of wrapped around my cock, but I did it. I restrained myself. I contained my intense desire.

"Come here, baby," Avery said as she opened her eyes again. "Come lick my pussy. Come make me feel good."

I crawled into the bed without a moment's hesitation and Avery moved her hand away so I could lick her pussy. I pushed my tongue inside her, soaked up those sweet juices, and then turned my attention to her clit. I licked slowly at first, keeping a steady rhythm and watching as Avery took both her breasts in her hands and squeezed the soft flesh before gently pulling on her nipples. She arched her back again and her moans filled the bedroom.

I expected Avery to cum quickly, but she didn't. Instead, she seemed to stay in that same place of arousal, like I was doing something wrong and therefore she couldn't quite get to the place she needed to be to have a great orgasm.

"Is everything okay?" I asked as I felt a sudden wave of insecurity over my ability to make Avery feel good.

She sat up on her elbows, looked down at me with a soft smile on her face, and said, "I need something more tonight. I don't know why. Your tongue is usually more than enough to make me feel good, but tonight it just isn't getting the job done."

"What can I do?" I asked.

Avery smiled and said, "Nothing." Then she scooted backwards and rolled over to open her nightstand. She reached inside and pulled out a toy I'd never seen before. It was a long, fairly thick, smooth dildo with a tapered tip. It was very much like a cock, though far more elegant looking. She moved a little closer - though not as close as before - spread her legs, and said, "This lovely new toy of mine, though, can give me exactly what I need."

She reached between her legs and rubbed the tip of the toy over her pussy lips, which were soaked in her juices and my saliva. It slipped inside her without much resistance and I watched her pussy lips cling to the thick rubber shaft as it slowly filled her.

"Oh, fuck," Avery said as she reached down and rubbed her clit. "That feels so good."

Avery fucked herself slowly, taking a little more of the toy with each thrust into her pussy. Eventually, though, she was taking every inch with ease. Over and over I watched the dildo disappear inside my wife, and it was astoundingly hot, as I'm sure you can imagine. It was a preview of being cuckolded. That was the point, of course. In the moment I was too caught up in the beauty of what I was watching to think about anything other than the toy fucking her, but Avery had set everything up. She'd bought the toy. She'd gotten me turned on. She'd told me that I couldn't make her cum, that she needed something else. She was training me.

"Does it look good, baby?" she asked. "Do you like watching this big toy fuck my pussy?"

"Yes," I answered immediately. I felt my stiff cock pressing into the bed. It was actually a little painful, but that was only because I was as hard as I'd ever been. That's how turned on I was.

Avery fucked herself a little faster and I couldn't help but sink deeper into the sense of astonished lust at felt at watching her masturbate. I got a little closer for a better view of her wet flesh opening up for the toy. I saw her pussy lips cling to it when she pulled it out. Then my imagination kicked in and suddenly I was watching her have sex with another man. I was watching someone else's big cock - bigger than mine, by the way - slide in and out of her pussy. I ascended to an entirely different place of pleasure as a result.

"Does it feel good?" I asked. "Does that...does that big cock feel good inside you?"

"Mmm," Avery moaned as she arched her back and pushed the toy deep into her pussy. She held it there and looked down at me with a smile on her face. "This big cock feels so fucking good inside me, baby. It's exactly what I needed today. It's exactly what my pussy craved. It's exactly what you couldn't give me."

She resumed fucking herself and, without thinking, I began to gently thrust my hips into the bed, like I was desperately searching for even the slightest hint of stimulation. It felt good, too. Looking back, it was kind of pathetic, but I wasn't thinking about that as I was doing it.

Avery pulled the toy from her pussy and said, "Taste me."

I moved forward and plunged my tongue into her pussy. I tasted her juices, and in my mind I was tasting the sex she'd had with another man. I know it wasn't that, but the fantasy was alive and well and it felt spectacularly good to let my brain go there for a few seconds.

"That's enough," Avery said. I pulled away from her pussy and she pushed the toy inside her once more. "I'm going to cum all over this big cock. And it's not going to count towards your total."

I hadn't thought of that, and it was agonizing, at least for a few moments. She'd gotten me worked up. She'd had me get her close. Then she'd substituted the toy and left me just as far from my next orgasm as I was when the evening began.

Then I watched her fuck her pussy with the thick dildo. I watched it move in and out of her. I heard how wet she was. The fantasy took over again. I was watching her fuck another man. I was watching someone else's cock slide in and out of my wife's pussy. I no longer cared that I'd have to wait a little longer for my next orgasm.

"Fuck, fuck, I'm close," Avery said. "Baby, I'm close to cumming. I'm close to cumming all over this big cock!"

I saw her pussy spasm as Avery pounded herself with the dildo and rubbed her clit. I saw her have a hugely pleasurable orgasm as she filled our bedroom with wild moans. I saw her cum while my cock pressed into the bed without any chance of an orgasm. I felt a certain kind of madness that only comes when you're overwhelmingly aroused and unable to cum. It was both wonderful and painful, which is a strange place to exist in, though I'd come to spend a great deal more time in that place as my training continued.

When she'd finished cumming, Avery pulled the toy from her pussy and set it aside. She sat up and said, "Kiss me."

I got up on my knees and kissed my wife as her fingers danced over the head of my cock. It was a soft, sensual kiss at first, but eventually it turned a great deal more passionate. For just a moment I thought she might make me cum - either by taking me inside her or giving me a handjob - but that was merely my desire speaking. She had no intention of letting me cum. I still had to give her fourteen more orgasms before I got to have one.

"Did you enjoy watching?" she asked softly.

"I loved it," I replied.

"That's good," Avery said. "It will be different when you watch a real cock filling my pussy, but tonight was a good start. Next time, I'll let you use the toy on me, and then it will count towards your total."

"Thank you," I said.

Avery looked down at my cock, smiled, and suggested, "Maybe you should take a cold shower. I don't want you suffering too much just because you haven't earned an orgasm yet."

"I'll be okay," I said.

Avery kissed me softly and then laid in the bed. "Why don't we cuddle, then?"

I happily cuddled up next to my naked wife. She rolled onto her side and we spooned. My stiff cock pressed into her thighs. It stayed stiff as we cuddled and talked for the next hour. My arousal refused to dim even a little, but that was the point. Avery wanted me turned on. She wanted me desperate. She wanted me in a perfect headspace to be trained.