The Cuckold Training Diaries - Part 12

Click here to read the previous parts of the story.

Milo

For years, cuckolding has been the only sexual fantasy I've entertained, mostly because nothing else could hold a candle to it when it came to my arousal. I'd try and fantasize about other things, but my mind would always wander back to cuckolding because the feelings were just so intense.

Then it happened. Avery cuckolded me. She fucked Asher at the wedding. She fucked him multiple times, in fact. My wife cuckolded me. I thought the feelings associated with my fantasies were intense, but they were nothing compared to the real thing.

I'd like to say that it was all pleasure. It wasn't, though. There was pleasure, of course. In fact, there was a greater level of pleasure than I've ever experienced before. There were unpleasant feelings too, though. There was anxiety. There was a certain level of shame for finding such pleasure in the idea of another man fucking my wife. There was a great deal of worry that Avery would suddenly decide she was no longer interested in being married to me.

There were times when all of those feelings collided over and over, generating explosive mixtures of pleasure and pain that mingled in my brain and coursed through my body, pulling me in multiple directions at the same time.

Those feelings weren't limited to the night of my first cuckolding, either. They were potent for a few weeks, though Avery seemed to understand that I was feeling a little raw and nervous about the whole thing, as she put me in chastity the day after the wedding, and after giving me a world class orgasm.

It might seem counterintuitive to lock a man in chastity after his first cuckolding, but as Avery described it, she wanted my lust to rebuild as quickly as possible and she didn't want me to feel tempted to masturbate, which I almost certainly would have done.

You see, my feelings came in waves. First I'd have this wave of overwhelming arousal and it would stick with me for a while as I let my mind fantasize about Avery getting fucked by Asher and cumming all over his cock. If I wasn't locked up, I would have been sorely tempted to masturbate despite Avery's ongoing insistence that she be in control of my orgasms. Because I was locked up I couldn't masturbate, and thus that desire continued to grow.

It was almost always tempered by the angst, but with the chastity device on my cock, that part never got overwhelming, and I can imagine it would have if I'd been left entirely to my own devices. In truth, I'm grateful that Avery has been so intent on training me to be a good cuckold, for I'm fairly certain I would have wandered off the path of goodness and become rather unpleasant if she hadn't been so determined to ensure my continued excellent behavior.

I went two weeks in the chastity cage, and during that time I offered Avery some sort of pleasure almost every single day. Sometimes it was as simple as a massage with a quick happy ending - often provided by my tongue or fingers - and sometimes it was a great deal more involved, like when Avery had me spend nearly an hour worshiping her body with my lips and tongue. I made her cum four times on that particular night and my cock throbbed in its cage the entire time.

The night she released me, though, was especially thrilling because it was the first time since my cuckolding that the subject of another man came up. She'd purposefully pulled back on any talk of fucking other men, which was an act of kindness, for she understood that I was feeling angst and she didn't want to fan those flames.

She must have judged two weeks as long enough, though, because she was on the phone with Alonso - the college boyfriend she'd been spectacularly slutty with - when I got home from a trip to the grocery store. It was a little before 5 p.m. and Avery was on the couch with her earbuds in and a smile on her face as I walked past with the bags of food in my hand.

"He just got home," she said.

I stopped at the edge of the living room as Avery's lips curled into a smile before she giggled in a decidedly flirtatious manner.

"Yes, he's still locked in the chastity cage," she said.

Now, I wasn't sure who she was talking to at the time, but I hoped it was either Alonso or Asher, for I wasn't keen on her sharing the fact that she'd locked up my cock with anyone else.

"It's been two weeks," Avery said. She stared at me for a few seconds and added, "Yes, it's been two weeks since I've been fucked, though Milo's been very good about tending to my needs with his tongue, his fingers, and a nice big dildo that stretches my tight little cunt so good."

I still wasn't sure who she was talking to, but I was turned on. My dick tried to get hard in the cage and I felt that beautiful pain almost immediately. I rushed into the kitchen, set the bags on the counter, and headed back to the living room.

"No, the toy doesn't compare to you, Alonso," Avery said as she beckoned me to come closer.

I approached and Avery mouthed the word 'strip.' I took my clothes off and tossed them aside, revealing my swollen, caged cock and the precum dripping from the tip. She reached out and I stepped close enough that my wife could take my chastised dick in her hand and rub her fingers over the small bits of flesh that were pushing out from between the steel bars.

"I'm holding his caged cock right now," Avery said softly. "But I wish I was holding your cock, Alonso. I wish you were the one standing next to me in my living room. I wish I could lean forward and take you in my mouth. I wish I could suck your cock like a good girl and make you hard for me."

If you're a cuckold - or a would-be cuckold - and you've never heard your wife utter those words to another man, you're missing out. It's an astonishingly arousing experience and I nearly doubled over from the ache between my legs.

"He likes that, Alonso," Avery said. "My husband likes that I wish I was sucking your cock. He likes that I wish another man was in our living room, that another man's big, beautiful cock was filling my mouth."

Avery looked up at me with a wild, lusty look in her eyes. I wasn't sure what Alonso was saying to her, but it must have been exactly what she wanted to hear because she closed her eyes and moaned as she released my cock and reached between her legs to rub her pussy through the thin material of her leggings.

"Mmm, fuck, Alonso, yes, I'd get on my knees for you," she said. "Yes, I'd let you fuck my face. Fuck, I'd even beg you to fuck my face. I'd beg you to pound my pretty mouth until your dick was so hard that you just had to bend me over and take me from behind."

She was in that place she only seemed to go to with Alonso, the place where she surrendered to her wildest, sluttiest desires. I always assumed it was because it was safe to go to that place with a guy that lived so far away, but the motivation didn't matter. I just loved how dirty she was willing to get with him.

"Hold on," Avery said before she pulled out her earbuds, set them on the coffee table, and put her phone on speaker. "Can you hear me?"

"I can," Alonso answered.

Avery pulled her leggings off and tossed them aside. She spread her legs, grabbed her phone, and slipped three fingers into her pussy. She fucked her exceedingly slippery hole with vigor and asked, "Can you hear that? Can you hear how wet I am for you, Alonso?"

I could almost hear the delight in his voice as he said, "Damn right I can. You sound as wet as I remember you getting back in college, Avery. That's how I always knew you wanted me, by the way. You were always fucking soaked. In fact, you got wetter than any girl I've ever fucked. I guess that means you wanted what I gave you more than any girl ever has."

Avery moaned and buried her fingers in her pussy as she looked up at me with a smile on her face. "I always felt bad about that," she admitted. "I felt like I wasn't supposed to want what you gave me, that I wasn't supposed to be turned on by the way I acted with you. I was, though. I was always so fucking turned on, Alonso. That's why I kept coming back to you. That's why I always let you do whatever you wanted with my body."

I've talked about this before, but I find it so fucking hot when Avery gets in touch with the part of her that seems to want to be a wanton slut. It's a version of her I've never truly met - I certainly never inspired her to tap into that side of her - so I've only ever experienced it while she's on the phone with Alonso.

When it happens, I can actually see the change in her. I can see it in her eyes, on her face, and in her body language. I can hear it in her voice, too. It takes on a different tone, almost as if an alternate personality has taken over.

"Did you enjoy fucking the guy at the wedding?" Alonso asked, indicating that Avery had shared at least some of the details of the night she cuckolded me.

Avery placed the phone on her chest, smiled, and fingered her pussy as she said, "It was exquisite. He took me to his room and he fucked me while my husband waited in the ballroom. He filled me with his big cock until my body was quivering. I even screamed his name in pleasure."

"I'm jealous of him," Alonso said. "And I don't get jealous all that often, Avery."

I watched Avery smile again, though this time it was a decidedly naughty look on her face, as if she enjoyed inspiring that jealousy in her ex-boyfriend. "Is that right?" she asked. "Is that because you want to fuck me, Alonso? Do you want to enjoy the pussy you used to fuck in college?"

"Yes, I do," Alonso said.

"You wish you were the man that got to cuckold my husband?" Avery asked.

"Damn right I do," he replied. "And while I love that you had a good time at the wedding, I'm certain I'd fuck you better than he did, Avery. I'm certain I'd make you wetter than he did, that I'd satisfy you in a way no man has since the last time I fucked you in college."

Avery closed her eyes and arched her back as she moaned. She pulled her fingers out of her pussy, looked at me, and lifted her hand. I bent over and took her fingers in my mouth. I sucked them clean, savoring the taste of her exceptionally sweet juices on my tongue in the process.

Avery sat up, set her phone on the couch, and put a hand on the top of my head to push me to my knees. Her fingers remained in my mouth and I looked up at her to see a seductive smile on her face. "Do you remember the last time you fucked me, Alonso?" she asked as her eyes remained locked on mine.

He paused for a moment and answered, "I do."

Avery pulled her fingers from my mouth, added a third, and slowly pushed them back in. I was utterly mesmerized by her stare and I didn't dare look away, particularly since she seemed to take such pleasure in gently fucking my mouth.

"That was the night I shared you with Josh," Alonso continued.

My eyes went wide, in part because Avery had never mentioned a word of being shared by an ex-boyfriend and in part because of the look of intense lust that passed over her face the moment Alonso mentioned it.

"That's right," Avery said as she pulled her fingers back until they rested at my lips. "You invited me to your dorm room. We had a few drinks and got wonderfully buzzed. I remember being desperate for you, desperate to have you inside me. I got naked and got on my knees in front of you. I pawed at your cock. I played with it through your jeans until you were hard. You wouldn't let me take it out, though."

"No, I wouldn't," Alonso replied in a voice dripping with lust. He took a heavy breath before adding, "I had other plans."

Avery smiled. She was turned on. She was hugely turned on thinking about the night that seemingly ended her relationship with Alonso. "There was a knock on the door," she said.

"I told you to answer it. You moved to get dressed but I told you to answer it naked," Alonso continued.

Avery pushed her fingers into my mouth and I closed my lips around them. I sucked and swirled my tongue around them as she moaned quietly. "I did what you wanted. I did what you told me to do. I was so desperate for you that I answered the door naked. Josh was standing there with a dumb smile on his face. He knew what you had planned. He knew what he was showing up at your room for."

"I told you to let him inside," Alonso said. "I told you to take his hand and guide him to my bed. I told you to get on your knees in front of him. I told you to be a good girl and suck his cock." I could hear Alonso stroking his cock and the smile on Avery's face made it obvious she could hear it too. "And what did you do?" he asked.

With her fingers still in my mouth, Avery grabbed my hand and pulled it between her legs. My fingers slipped inside her with ease and I rubbed her clit as she moaned. She wanted me to know how wet she was. She wanted to make it obvious that she was turned on by the story she and Alonso were telling.

"I was a good girl," Avery said. "I got on my knees in front of Josh. I took his pants off. I sucked his cock."

"And what did I do?" Alonso asked.

"You fingered me," Avery answered. "You fingered my pussy and played with my tits while I blew your friend."

Avery's pussy had completely soaked my fingers and I could hear the sounds of wet stroking coming through the phone, which I took to mean that Alonso was dripping precum.

"He put his hands in my hair and pulled me down on his cock," Avery continued. "He made me take him in my throat, though he wasn't anywhere near as big as you were, so it wasn't that hard."

I honestly couldn't believe how turned on Avery looked. I could see it all over her face, like every moment of reliving this memory got her a little more worked up. I don't know if it's because she'd actually cuckolded me and unlocked some previously hidden part of her or if Alonso had simply awoken this side of her, but it was incredible.

"And after you made him hard, what did I tell you to do?" Alonso asked.

"You told me to get on my hands and knees in your bed," Avery answered. She bit her lip and let out a long, low moan. It was almost as if she'd been saving it up, or trying to stave it off and it just flowed out of her like an uncontrollable river. She closed her eyes and I rubbed her clit a little faster while she continued to fuck my mouth with her fingers.

"And what did I tell Josh to do?" Alonso asked.

"You told him to fuck me," Avery answered. "You told him to fuck me from behind. He got naked, got in the bed behind me, and put his cock inside me. He fucked me hard. Really hard. He used me. He used my pussy just like he'd used my mouth."

"And what did I do?" Alonso asked.

Avery pulled her fingers from my mouth, wiped the saliva on the side of my face, and leaned in. Her lips were achingly close to mine as she said, "You watched your friend use me. You sat there with a smile on your face and you watched him fuck me." She kissed me. Her tongue pushed into my mouth as I fingered her hard. She moaned loudly and I moaned right along with her. I was completely caught up in her arousal. My dick hurt like hell as it tried to get hard in the cage but I honestly loved that overwhelming sensation of desire.

"Where did Josh cum?" Alonso asked.

Avery sat back, pulled my fingers from her pussy, and took them in her mouth. She sucked hard and swirled her tongue around them, just as I'd done. "He came in my mouth," she said. "You told him to cum in my mouth and I didn't hesitate to spin around so he could do so. I wrapped my lips around his cock and let him fuck my face until he came."

"And then I told you to swallow," Alonso said.

Avery smiled at me. "And I did. I swallowed Josh's cum. I swallowed his cum and then you told him to get dressed and leave. I stared at you the entire time he was getting dressed. I stared as you stood up and unzipped your pants. I stared at your cock as you pulled it out. I stared and I felt the most intense need I'd ever experienced."

"You needed me to fuck you," Alonso said. "You were desperate for it. That's why you let me share you with Josh. That's why you did exactly as I told you and why you did it without hesitation. That's why you let him fuck you doggystyle. That's why you let him cum in your mouth. That's why you swallowed his cum."

Avery looked desperately horny, but she was holding off on cumming. She must have been, for it wouldn't have taken much to give her an orgasm. "I was desperate for you. I was. I was...I was such a slut for you, Alonso. I was such a slut for you...and I loved it. I came so fucking hard every time you used me. I don't know why...I don't know why I'm so fucking wet right now...I don't know why I wish you were here right now, why I wish you would use me again."

"Who cares about why?" Alonso asked. "All that matters is that you know what you want, Avery. You know what you crave. You know what would make you feel better than anything else."

Avery smiled at me, grabbed a handful of my hair, and pulled me between her legs. She was kind of rough about it, but I honestly enjoyed that. I moaned as she rubbed her pussy over my face, soaking me in her juices and generating pleasure for her clit. When she loosened her grip I put my tongue to work on her clit as I figured that's precisely what she wanted.

"I want to be fucked like you fucked me that night, Alonso," Avery said. "I want to feel like I felt that night."

"How did I fuck you, Avery?" he asked.

I looked up at my wife as she smiled and unleashed a moan. "It was...animalistic. You fucked my throat to get your cock wet and then spun me around in your bed. You pushed my face down, slid your cock into my pussy, and dug your fingers into my hips. You fucked me with such power I thought you were going to break the bed. You bruised my pussy. You didn't give a damn about anything other than pursuing your pleasure, and you made me cum so fucking hard. I can still remember my fingers and toes tingling as I walked home. I can still remember how sore my pussy felt. I can remember how sore my asshole felt from you shoving your thumb inside me as you pounded me."

"Is that how you got fucked at the wedding, Avery?" Alonso asked.

"No," she said. "The sex was great, and he made me cum hard, but that's not how he fucked me, Alonso. He didn't fuck me like you used to. He didn't fuck me like I truly want and need to be fucked."

"Do you want me to come visit, Avery?" Alonso asked.

She grabbed a handful of my hair and moaned.

"Do you want me to come and see you? Do you want me to invite you to my hotel? Do you want me to fuck you like you need to be fucked? Do you want me to make your husband watch as I fuck you like that?" he asked.

Avery's thighs closed around my head and I felt her tremble. I licked her clit feverishly and looked up to see her eyes were shut tight and she had a look of pure pleasure on her face.

"Yes!" she screamed. "Yes, fuck, Alonso! I want you to visit! I want you to give me what I need! I can't stop thinking about you! I can't! I fucking can't!"

She came just a few moments later. It was a long, loud, screaming orgasm. Her legs kicked open and wetness leaked from her pussy as I gently licked her clit, doing my best to lure a deeply pleasurable orgasm out of her.

Alonso came too, if all the grunts and groans were any indicator. Avery's feet sank to the ground and she smiled while listening to her ex have an orgasm and ran her fingers through my hair in a gentle, loving manner.

"Thank you, Alonso," she said softly.

"No, thank you," he replied.

"I've got to go," Avery said. "My husband deserves an orgasm."

"I'll talk to you soon," Alonso said.

Avery hung up, leaned forward to kiss me, and grabbed the key to my cage from the coffee table drawer. She unlocked my cock, had me sit on the couch, and rode me slowly as we kissed. She didn't say a word about her conversation with Alonso or her seeming desire to have him come visit. Instead, she offered me the pleasure of her pussy and I experienced a blissful orgasm inside my wife.

It was quick. Really quick. Of course it was quick. It was wonderful, though. It was truly wonderful, and made all the more arousing by the conversation I'd listened to and the imagery of my wife being so desperate for another man's cock that she happily let him share her in the manner Alonso had done.

I could only hope that I'd get to meet that version of Avery in the near future.