The Cuckold Training Diaries - Part 4

Click here to read the previous parts of the story.

Milo

"Do you think guys can sense when a married woman is considering stepping outside her marriage?" Avery asked. It was a Saturday afternoon. She'd just gotten back from the gym and she looked good in a pair of leggings and one of those long-sleeved athletic jackets. Her hair was in a ponytail, too, which it almost never is, and I do love a ponytail on my wife.

The question, though, caught me a bit off guard, so I didn't have an answer. Instead, I asked a question of my own. "Why is that on your mind?"

Avery took a sip from her water bottle, put her hands on her hips, and smiled. "Well, I feel like guys are flirting with me more, and I can't help but wonder why."

So, you know that I want Avery to cuckold me. You know that I fantasize about it, that I've long fantasized about it, as do most guys that ask their wives to cuckold them. It's also worth mentioning that I'd gone three weeks without an orgasm when this conversation took place. As a result, the idea of a guy even flirting with Avery was enough to turn me on. Like, legitimately turn me on. "Wait, guys are flirting with you?" I asked as I sat up a little straighter on the couch, making it perfectly obvious I was delighted with Avery's little reveal.

"Yeah," she said. "There were two guys at the gym today. At separate times, but yeah, they were both definitely flirting. One even asked for my number."

"Wait, really?" I asked. I was beyond excited. I mean, it was such a small thing, but it also felt like a big thing.

She nodded and sipped her water again and I couldn't help but stare. She looked so good - fit women always look good in modern athletic wear - and I was so fucking horny that I just wanted to run across the room, pick her up, run to the bedroom, and fuck her. Throw in the extra excitement about someone flirting with her - the tiniest little taste of cuckolding - and I was all kinds of worked up.

"It's happened at the grocery store a few times. It happened when I went shopping to get that dress for Ella's wedding. I feel like guys check me out a lot more often, too," she noted.

I tried my very best to calm down and see if I could answer Avery's original question, which was if guys could sense that a woman was considering stepping outside her marriage. "Well, I mean, if more guys are flirting with you and checking you out, then something must be different. I don't know if they can sense that you're considering fucking other people, but they can probably sense that something is different. Maybe it's you, though."

Avery dropped into the armchair across from the couch and crossed her legs. "Me? What do you mean?"

"Well, I don't know, but maybe you're checking out guys more than you think," I suggested. "Like at the gym. Maybe you're looking to see if any of the guys appeal to you. I mean, that wouldn't be crazy. You said if you were going to do it than you'd want to find someone that could fuck you really good, right? So, I assume a guy in really great shape would have a better chance of giving you that, so maybe you're just staring a little more and guys interpret that as an invitation to do a little flirting."

Avery stared at me for a few seconds and then her lips curled into a slight smile. "You know, I think you might be right. I think there's a chance that I'm checking guys out and not really even noticing it."

I know that's such a small thing, but I couldn't help but find it exciting. After three weeks of orgasm denial I was really kind of desperate and the idea of Avery checking guys out was so hot. Of course, in my mind the fantasy quickly became that she went from checking one of them out to fucking one of them in his car in the parking lot, or in the locker room. The specifics didn't really matter. It was just that I so desperately wanted my wife to cuckold me.

"Are you turned on, Milo?" Avery asked me.

That's when I snapped back to attention and realized that I'd basically spaced out for a handful of seconds as I fantasized. "Yes," I answered. "I know that's probably kind of weird, but I'm turned on. I just really like the idea of guys flirting with you. It just seems so exciting, you know? Like, maybe flirting leads to you actually giving someone your number. Maybe that leads to a date. Maybe that leads to..."

"To me cuckolding you?" she asked. I nodded and Avery smiled and stood up. She crossed the living room, spun around, and lowered her ass to my lap. My hands moved to her waist and I kissed her neck as she gently moved her utterly perfect ass over my crotch, quickly making my dick hard as a rock. "Are you sure that's what you really want, Milo?"

"Yes. Of course," I answered. It struck me as an insane question. Of course that's what I really wanted. I couldn't stop thinking about it.

"Do you really think you'd enjoy it if another man fucked me, Milo?" she asked. Her voice was so laced with lust that I couldn't help but think she was actually trying to tease me, to turn me on. I mean, when she said it the only thing I could think about was someone else fucking her.

"Yes, Avery, I'd enjoy that more than anything," I said.

Avery leaned into my body and turned her head to kiss my neck. She moaned and her voice was soft and seductive as she said, "Even if he fucked me better than you, Milo? Even if he made me cum harder than you do? Would you still like it? Would it still turn you on if I came home and told you that I'd found someone who's better than you in bed?"

"Avery...fuck..." That was all I could manage. Truly. It actually felt like I was pretty close to cumming from what amounted to a lap dance.

It must have been obvious that I was getting close, because she stopped grinding in my lap and stood up. She had a smile on her face, though, and she launched into a striptease. It was so fucking hot. I'm sure part of it was that I was out of my mind with lust, but Avery looked so good as she took off her jacket, stripped out of the sports bra she wore underneath it, and then slowly peeled off those leggings, under which she wore nothing at all. Just like that she was naked in front me and holy fuck did she look good.

"How many more orgasms do you have to give me before you get to cum, Milo?" she asked.

"Eleven," I answered, which was agonizing.

"How about I let you make me cum right now?" she suggested.

"Yes, please, I would love that," I said. "I just want to make you cum, Avery. I just want to make you feel good."

"Even if I want to fantasize about another man?" she asked.

I was astounded. I could actually feel my eyes open wider and my jaw drop. Avery had teased a little about another guy - the guy that smiled at her in the Victoria's Secret, for instance - but she hadn't fully committed to fantasizing about someone else, at least not that she'd told me about. "Do you really want to do that?"

Avery reached between her legs and rubbed her pussy as she took one of her breasts in her hand. My eyes darted from her crotch to her chest and back again as she bit her lower lip for a moment and moaned. "The guy who asked for my number...he was hot, Milo. And you're probably right that he came over to flirt with me because I was staring at him a little. I don't know...I just felt attracted to him. Not in that way where you think someone is good looking, but in that way where there's something about a guy that just draws you to him. I felt that today. I didn't think I was being obvious about it, but I guess I was. I guess he could tell that I thought he was hot, that I couldn't help but feel desire for him."

I can't say for sure if Avery was being honest or if she was just trying to turn me on, but I really do believe she was being honest. Mostly that's because she was full-on masturbating right there in front of me and she really seemed into it. Also, she was wet. Like, wet enough that I could hear it as she rubbed her fingers over her pussy lips.

That's why I slid off the couch, pulled her hand aside, and went to work eating her pussy. Avery moaned and put her hand on my head. She moved her hips a little, too, almost like she was kinda sorta fucking my mouth. It was exceedingly hot.

"I flirted with him," Avery said. "I know I said he flirted with me, but I flirted back. He told me I looked better than most women that come to the gym. I told him he looked better than most guys. He looked right at my ring when I said it, Milo. He looked right at the ring you gave me, smiled, and then told me I was beautiful."

You know you're all in on cuckolding when a story about a little bit of flirting is a huge turn on. Part of my arousal - a big part of it, honestly - was that I was playing out a fantasy in my head. I was imagining Avery flirting, then giving him her number, then dating him, then fucking him. I was imagining all of my cuckold desires playing out, and it was so fucking hot.

"He asked for my number after that," she said. "He didn't waste any time, Milo. He wanted me. He wanted your wife. He wanted to fuck me."

Now she was trying to turn me on. She was trying to get me in that crazed headspace where all I can think about is cuckolding. It worked, too. It worked like a charm. I didn't stop licking her clit, though. I was focused on trying to make her cum, on giving her what I knew she wanted.

"Oh...fuck...Milo, I'm cumming," she said.

Avery leaned forward and grabbed the back of the couch as her legs trembled while I kept my tongue working her clit. I did so right up until she pulled it away from my mouth and rolled onto the couch with a look of utter joy on her face as the pleasures of her climax continued to work their way through her body.

"Ten more to go," she said before laughing, seemingly from the joy of such a good orgasm. "You know what, I want you to get naked and then go get my toy."

I stood, I stripped as quickly as possible, and then I practically ran to the bedroom to grab her toy. There was something oddly pleasurable about doing it naked, too, like it somehow got me closer to an orgasm, which it absolutely did not, as I was looking at having to make Avery cum ten more times before I'd get to climax.

I returned with the toy and Avery spread her legs. I crawled between them with a smile on my face because it seemed like I was going to get a chance to make her cum again.

"Put your cock inside me," Avery said.

"What? Really?" I asked.

"You don't get to fuck me, but you can put your cock inside me," she clarified.

I paused for a moment, only because I was honestly a little worried that I'd have trouble just putting my cock inside her. I figured I might just try and fuck her once I felt that pleasure. I wasn't going to pass up on the opportunity to enjoy her pussy, though, so I set the toy aside and crawled between her legs. Avery spread them a little wider and I guided my cock inside her and enveloped it in a sense of the most perfect bliss. I swear, after three weeks of total denial there is nothing better than being inside your wife's pussy.

"Does that feel good?" she asked.

"It feels so much better than good," I answered.

Avery reached up and pulled my head to hers so we could kiss. She ran her hands down my back and grabbed my ass, squeezing it tight. Her tongue swirled in my mouth and it took every ounce of self control I had not to try and fuck her.

"I wonder if the guy that flirted with me - Andrew was his name - I wonder if he had a big cock." Avery said. "I wonder if he was bigger than you, Milo. I wonder if he was as big as my toy. I wonder if he would feel better inside me than you do."

There is nothing quite like your wife openly wondering if someone else's cock would feel better while you're inside her. It's even more difficult to deal with when you're not allowed to fuck her, when she's taken you in her pussy but has denied you the actual pleasure of her pussy.

"Do you want me to fuck someone with a bigger cock, Milo?" she asked.

"Yes," I answered.

"Is that because you think I'll enjoy a bigger cock more?" she asked.

I actually had to grit my teeth for a moment to resist the urge to fuck her. "Yes. I do. Or, at least, I hope you will."

Avery smiled and kissed me. Her lips then moved to my neck and she gently sucked on my flesh before whispering, "Oh, I will. A bigger cock is almost always better, Milo. That's why I bought that big toy. Now I want you to pull out my pussy and fuck me with that toy. I want you to fuck me hard, too. I want you to fuck me while I fantasize about my flirty friend from the gym."

I pulled out so fast I nearly fell off the couch. I grabbed the toy, moved back a little, and then gently inserted it into Avery's pussy. A few days prior I'd tried to push it inside her a little too quickly and it had caused a bit of pain because it wasn't lubed. This time, I avoided that mistake and I slowly filled my wife with the long, thick dildo she'd bought.

Avery closed her eyes and took both of her breasts in her hands. She arched her back just a little and rolled her head towards the ceiling. She looked insanely hot and the moan she unleashed was astonishing.

"Andrew," she said softly. "Fuck me. Give me your big cock. Fuck me with that big, beautiful cock of yours."

It's so hot to hear your wife say another man's name. Just so fucking hot. My dick was so hard it hurt, and once the toy was lubed I gave Avery a good fucking. I pounded her hard and deep and I reached up to use my thumb to play with her clit, offering that extra bit of pleasure that quickly had her in a place where she was quivering from the pleasure.

"Fuck me, Andrew! Fuck me while my husband watches! Stretch out my tight pussy with your big cock while my cuckold husband watches!" Avery cried out.

She came soon after. It was loud and beautiful and some juice actually leaked out of her pussy around the toy, which I held deep inside her because it looked so beautiful.

"Wow," she said as her eyes opened and she looked down at me. "Two orgasms in one day."

"Thank you for letting me fuck you with the toy," I replied.

Avery sat up as I pulled the toy from her pussy and we shared a kiss. "You're welcome. Would you like to make me cum a third time?"

"Absolutely," I answered.

"Good. Let's go to the bedroom. I want to tease you a little more," she replied. "You're being so good, though. You're making me so happy, Milo."

"It's my pleasure, believe me," I said.

Avery stood and took my hand. She led me to the bedroom and soon enough she was on top of me with my cock inside her, setting off yet another round of teasing that would end with the toy inside her once again and yet another orgasm pouring fourth from her body.

That left me with only eight more to go. Sadly, I didn't make it. In a moment of weakness I surrendered to my lust and broke the rules. I paid for it, too, but that's for next time.