The Cuckold Training Diaries - Part 7

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Milo

"Did I ever tell you about Alonso?" Avery asked me as we were crawling into bed one night. It wasn't until that moment - until she posed the question - that I noticed she'd changed into a rather sexy camisole and a pair of lace panties. The look on her face made it clear that she was in the mood to have a little fun, that her question was likely the prelude to some kind of cuckold training.

"No," I answered. At that point I'd given her 10 of the 20 orgasms required before my release from chastity. Only ten days had passed since she'd locked me up, which meant that I was on the verge of feeling desperate, which also meant that even the hint of some cuckold-fueled fun was enough to generate a bit of excitement between my legs.

Avery pulled back the covers and crawled into the bed. "Strip for me," she said.

I stripped as instructed and crawled into bed. Avery then opened her nightstand drawer and pulled out the key to my cock cage. I was stunned as I didn't expect to even sniff at freedom until I'd given her another 10 orgasms. She unlocked me, though. She set my cock free and leaned over my body to set the pieces of the cage on my nightstand. As she did, her beautiful breasts pressed into my chest through the thin, soft material of her camisole and the scent of a delicate perfume filled my nose. They were both small things, but they had what I imagine was the desired effect as my cock came to life.

"I dated Alonso for a few months when I was in college," she said. "It was my senior year, so I was living in an off-campus apartment with two of my best friends."

Avery laid next to me and I felt the soft material of her camisole and the perky flesh of her breasts press into my chest. She put her leg over mine and pressed her pelvis against my hip. Our bodies were as close as they could be without her lying right on top of me and it was exquisite.

"Alonso was the classic bad boy," Avery continued. "He was almost a cliché, to be honest. It's the kind of relationship that I'm a little bit embarrassed of when I look back on it. He wasn't a good boyfriend. Not by any means. He wasn't abusive, or anything like that, but he was the sort of guy that paid attention to me when he saw fit and didn't really seem to care what I thought."

I was still turned on - Avery was pressed up against me, after all - but I was confused as to why she was telling me about a bad relationship from her past.

"Do you know why girls like to date the bad boy?" Avery asked.

"No," I answered. As you might have already guessed, I was not the bad boy type.

Her fingers moved over my chest, gently teasing my skin and providing far more pleasure than you might think possible from such a simple bit of touching. "There's this notion - spread by women, I'm sure - that it's about this desire to tame the bad boy, that there's something endlessly alluring about being able to charm someone like that into turning into a good guy, into the kind of guy that will settle down." Her fingers moved over my stomach and between my legs and she took my half-hard cock in her hand. "That's not what it's about, though."

"No?" I asked.

Avery smiled and leaned closer to kiss my neck. "No," she said softly. "It's about the sex. It's always about the sex. Some girls don't want to admit that, which I get. Though don't want to feel like they're being slutty. They don't want to be accused of being slutty. They don't want to admit that they're willing to let a guy act like an asshole just because he fucks them so good. But that's always what it's about. The bad boy always fucks better. Always."

My dick was hard. I was thinking about Avery being the kind of woman who'd be with a guy just for the sex, which she seemed to be implying. That was not the version of Avery that I knew, and yet it was absolutely the version of her that I hoped to know someday soon. "Did Alonso fuck you like that? Was he that good?"

"Oh, baby, Alonso was better than good," Avery answered. "Alonso fucked me better than anyone had at that point in my life. He showed me pleasures no man ever had. He showed me that sex could be so good that it's the only thing on your mind. All day, every day. Honestly, the only reason I broke up with him was because my grades were suffering."

I thought of Avery kissing Carter, the guy at the bar. I couldn't help but wonder if that kiss had awakened the version of my wife that had gotten so lost in the pleasures of sex that she'd nearly blown her GPA. Was there a part of her that loved sex so much she could fully embrace being a hotwife so we could explore my fantasy together?

"Would you like to hear about it?" Avery asked. "About the sex I had with Alonso?"

"Yes, absolutely," I answered, betraying my overwhelming sense of excitement.

Avery released my cock and for a moment I was disappointed. Then she got up on her knees and straddled my thighs. She moved forward until my cock rested against her pelvis. Her panties felt soft and delicate against my stiff flesh and I couldn't help but stare, in part because I was thinking that it was a perfect display of how deep I'd reach inside her if we were to fuck. It wasn't all that deep, but of course I'm not all that big, so that makes sense.

"You don't mind hearing about how an ex-boyfriend fucked me?" Avery asked.

I saw the playfulness on her face and the light of desire in her eyes. It made me smile. "You know I don't. You know it turns me on."

Avery leaned forward and the head of my cock rubbed against her body. Her lips found mine for a soft kiss before she whispered, "I do know that. The question is, do you have the will not to cum as I tell you about the fun I had with Alonso? Because you know I'll be very upset if you cum."

"I won't cum," I said, though I had no idea if that was true. Avery was really the one in control of my orgasms. She knew that, though. She was playing with me. She was teasing and tempting and she was doing it to train me. I didn't want to cum, though. I wanted to hold off. I wanted to make her happy. I just wasn't sure I could do it.

Avery

His cock was so hard. The look in his eyes was incredible, too. He was so turned on. To the point that he looked a little nervous about cumming, and about disappointing me if he did. I had no intention of making him cum, but I did have every intention of edging him, of teasing him, and of denying him the pleasure he'd end up quite desperate to experience.

"Once, I was getting out of calculus and Alonso happened to be walking by. I hadn't seen him in a few days and I felt this instant rush of desire for him. He was talking with a few of his friends and I walked over to him. He glanced at me, smiled, and turned back to his friends. He didn't say a word. He didn't even say hi. He was ignoring me. It was embarrassing, but I stayed. I wanted him so badly that I stood there until he was finished talking with his friends. He said goodbye to them and then turned to me. He looked me up and down, smiled, and then slipped a finger through one of the belt loops on my jeans and pulled me close for a kiss. He hadn't bothered to say a word to me and I was more than happy to let his tongue in my mouth," I explained.

I could see Milo's mind working as I played with his cock. I wasn't entirely sure what he was thinking, but I'm fairly certain he loved the idea that I could be so caught up in lust with a guy that I'd be genuinely desperate for him, that I'd let him treat me like that. I did, too. Alonso fucked me so good that I was willing to suffer through the indignities he sometimes required of me. I wouldn't do that now, but I was 22 and I knew I wasn't going to marry him. I just wanted to fuck him.

"He put his hand in my pants right there in the hallway. He fingered me right there with people walking by. If I wasn't so caught up in how good it felt when he fucked me, I would have stopped him. I would have walked away. I didn't, though. Do you want to know what I did?" I asked.

Milo nodded. By that point he looked like I'd felt with Alonso, like he was so completely caught up in his lust that he couldn't even think straight.

"At first, I just sucked on his tongue. I moaned for him, too. It was a quiet moan, but it felt fucking great when he fingered me in the hallway. My pussy was soaked for him, Milo. Soaked for him in a way I hadn't been soaked for anyone before that," I explained. "I probably would have let him make me cum right there, if I'm being honest. I was young and horny and I wasn't thinking straight. Alonso had other plans, though."

"What...what did he do?" Milo asked.

I slid back a little and reached down to take Milo's balls in one hand while I stroked his cock with the other. I kept it nice and slow as I didn't want him cumming, and it was fairly obvious he was in a highly aroused state and might pop off at a moment's notice.

"He took my hand and led me to the stairwell at the far end of the building. It was almost always empty because there were so few classrooms at that end. He took me all the way to the top floor and he uttered three words: Suck my dick," I said. The moment was so clear in my mind. Alonso had gotten me worked up with almost no effort and I'd happily followed as he led me through the building and to his preferred spot. I remember how turned on I felt, too, like the whole thing was so exciting.

"What did you do?" Milo asked.

I smiled at my desperately horny husband. "I did what girls do for bad boys, Milo. I got on my knees and I sucked his dick." That's absolutely what I did. I did it without hesitation, too.

Milo's cock felt exceptionally hard as I stroked him. Hard in the way a man only gets when he's hugely aroused, or when he's hugely aroused and he hasn't had an orgasm in a week and a half.

"You know what's crazy about girls with guys like that?" I asked. Milo shook his head. "I would have sucked him off. I wouldn't have gotten the pleasure I wanted. I wouldn't have had an orgasm. But I would have let him cum in my mouth. I would have swallowed for him. That's what happens when a girl is fucking a guy like that, though. He fucks her so good that she's more than happy to suck his cock and swallow for him because she knows it will ensure that he wants her again. Even if he's an asshole, she'll do it, and Alonso was often an asshole. I would have sucked him off, though."

"Did you?" Milo asked.

"No," I replied. "He didn't want to cum in my mouth. He wanted to fuck me. So he stood me up, unbuttoned my pants and pushed them down to my knees. He turned me around, bent me over the railing, and then pulled a condom from his back pocket and put it on. He slipped inside me from behind and he fucked me so hard. I gripped the railing with both hands and I took it, Milo. I took his cock. I let him use my pussy."

Milo was on the verge of cumming, so I wrapped my fingers around the base of his cock and I squeezed hard. I watched him fight to prevent the orgasm from overtaking him. He looked like he was experiencing a very particular kind of agony, and it was so much more of a turn on than I expected. It was yet another strong piece of evidence that Milo really was meant to be a cuckold, or at least that he was more aroused by cuckolding than anything else.

"Shit, I got really close there," he said.

"Because you were thinking about me letting Alonso use my pussy?" I asked. "Does it turn you on to think of your wife as that kind of woman, Milo? Do you like the idea of me being so fucking turned on by a guy that I'd let him use me like that?"

"Yes," Milo admitted.

Now, some women would have found that offensive, as some women really hate the idea of feeling used or feeling slutty in any way. I, obviously, am not one of those women. I wouldn't have stayed with Alonso beyond our first date (which ended with me giving him a blowjob) if I was that kind of woman. That too was another piece of evidence in favor of cuckolding Milo, though in this case it was more about my suitability for being the woman that cuckolded him.

I released his cock and crawled forward, bypassing it entirely until I was sitting on Milo's chest. "And would it turn you on to know that I had an orgasm as Alonso fucked me doggystyle in the stairwell? That he fucked me so good with that big dick of his that I came all over it before he buried it inside me and had an orgasm of his own?"

"Yes," Milo said. "Avery, fuck, yes, that's so hot."

I crawled forward, pinning Milo's arms under my knees and resting my pussy over his face. I pulled my panties aside, smiled, and said, "Eat my pussy, Milo. Make me cum. Thinking of Alonso has me all wet and I could really use a good orgasm. So use that tongue of yours. Make me cum while I think about Alonso."

Milo did just that, and I absolutely thought about Alonso. I thought about the time we went to the movies and I sucked his cock - and swallowed - twice (he fingered me once). I thought about the time that he fucked me in the park. He had me up against a tree. It was a quickie. Less than a minute. It was so fucking hot, though. It was just so wild. I thought about the time he fucked me in my roommate's bed just because he wanted to. I remember getting off on that little bit of naughtiness. I even thought about the time that he very nearly convinced me to let him share me with a friend of his. It never came to pass, but for some reason, as I was riding Milo's face, the idea was suddenly quite the turn on.

I came hard as all those thoughts danced through my head one after the other. In fact, I came hard enough that I leaked a little bit of juice onto Milo's face, making quite a mess of him.

All told, it was a successful training session. Milo didn't even struggle to free his arms so he could play with his cock while eating me out. For that reason, I let him make me cum a second time, taking his count to 12. I had something special planned for the 20th orgasm and I didn’t mind getting there a little quicker than I’d previously planned.

I’ll tell you about that special something next time.