The Cuckold Training Diaries - Part 11

Click here to read the previous parts of the story.

Avery

I didn't decide to cuckold Milo until I walked into the ballroom after having him lick my pussy in the bathroom. I was considering it, but it wasn't until I saw Asher and felt an overwhelming sense of desire that I decided I was going fuck him. In a way, I didn't even make the decision. My body made it for me. It told me that I needed to fuck Asher, that I needed to cuckold my husband.

So that's what I did. I went up to Asher and told him to take me to his room. He didn't hesitate. We left the ballroom - though we tried to be somewhat discreet about it - and then he took my hand and we walked across the lobby and towards the elevators. My pussy was even wetter than after I'd stepped out of the bathroom. My whole body was tingling with desire for Asher.

We kissed the moment we stepped onto the elevator. His hands moved down my back and he grabbed my ass and I moaned into his mouth. Our tongues danced and I felt the bulge of his cock press into my stomach as I slowly backed up until I was leaning against the elevator wall. The doors closed but our lips didn't part. We kept kissing. One of his hands moved up my body and he grasped my breast through the rather thin material of my dress. I let my hand wander, too, and I found his cock. I played with it through his pants and he moaned into my mouth. I was so turned on I even considered getting on my knees for him right there in the elevator.

We rushed down the hallway - and past an older couple that clearly noticed Asher's erection - and into his room. We kissed again the moment we stepped inside and slowly made our way towards the bed. I sat down and unzipped his pants while he leaned over and kissed me again. I pulled out his cock and stroked him while our tongues entwined, making Asher moan into my mouth.

He stood up and I leaned forward and took him in my mouth. I gave another man a blowjob while my husband was downstairs at the wedding. There was something kind of magical about the moment Asher's cock passed between my lips. Kissing Carter in the bar and having phone sex with Alonso were little more than appetizers compared to giving a blowjob, in particular because that blowjob was going to lead to me getting fucked, to actually cuckolding Milo. Needless to say, it turned me on. Massively so, in fact. I could actually feel the wetness in my panties as I sucked Asher's cock, which was gorgeous, by the way. Long and thick with a nice plump head that felt wondrous to suck on.

"Holy shit," Asher said as I gave him a blowjob. "Avery, you're so fucking hot...and I can’t believe how good that feels."

I like it when a man thinks he's lucky because he gets to fuck me. There's something so flattering about that. I kept on sucking him - I actually got really into it - as I sat on the edge of the bed, but I had no intention of making him cum in my mouth. I wanted him in my pussy when he had his orgasm, so eventually I released him from the tight grasp of my lips, moved back into bed, and pulled my panties off.

"Do you have condoms?" I asked.

Asher nodded, rushed towards his suitcase, and pulled out a box of condoms. He tore one open and took his pants off as I laid back and played with my wet pussy. I wanted him to both see and hear how turned on I was, and given that he couldn't keep his eyes off of the sight of my slippery cunt while he put the condom over his cock, I'm pretty sure I accomplished my goal.

"Do you want me?" I asked as Asher took his jacket off and crawled into the bed.

"Like you wouldn't believe," he answered.

I spread my legs a little wider and he moved between them. I'm not sure why, but the whole thing felt hotter because I hadn't taken my dress off. I liked that. I loved that, even. I liked that I was going to go back down to the reception and dance with Milo in a dress that someone else had fucked me in.

"Then fuck me," I said as the head of Asher's cock moved over my pussy lips. "Fuck me hard."

Asher slipped inside my soaking wet pussy and filled me slowly. I reached up and pulled his lips to mine so we could share a deep kiss. I wrapped my legs around him and held him close once he bottomed out inside me.

"You feel so good," I said breathlessly. "Your cock feels so good inside me."

He pulled out slowly, remained still for a few moments with just the tip of his beautiful cock inside me, and then filled me. I closed my eyes, arched my back, and moaned. It felt so much better than I thought it would. It felt better than when Milo fucked me, partly because Asher was bigger than my husband and partly because it turned out that fucking another man while my husband waited downstairs was so much hotter than I expected.

That's why I came so quickly. It couldn't have been more than a few minutes before I had a loud, body-shaking orgasm. My toes were actually tingling and I was a little bit lightheaded for a few seconds as the pleasure of it washed over me.

"Wow," I said afterwards as I felt a huge smile break across my face. "That was...Asher...I haven't cum like that in a long time."

Asher smiled too, though I could tell he was a little worried he wasn't going to get to cum. There was no chance that was happening, though.

"Don't worry," I said. "You're going to cum. It's the least I can do given how hard you just made me cum. Get on your back."

He pulled out and rolled onto his back. I straddled him and my dress billowed out around us on the bed. I reached under it and took him inside me. He was still hard as a rock - harder than Milo's cock gets, in fact - and he filled me with ease once more. I was even wetter than before, though, so that made perfect sense.

I put my hands on his chest - which felt wonderfully muscular - and smiled as I rode him. I'd already cum and I felt no need to aggressively pursue another orgasm, so I focused entirely on making Asher feel good. I bounced my pussy on his cock. I rode him fast and hard. I moaned for him. I told him how good his big cock felt in my pussy. I told him how I wanted to make him cum.

Eventually, he did, and by the look on his face, it seemed as though he came particularly hard, as if his orgasm was just as enjoyable as mine. I was surprised at how happy it made me to give him such a good orgasm. It felt like yet another piece of evidence that cuckolding was actually the right choice for my marriage.

"God damn," Asher said after he'd come down from his climax. "That was unbelievable, Avery."

I smiled and leaned down to kiss him while his cock remained inside me. Our tongues gently entwined and I thought of Milo and wondered if he'd enjoy the notion that his wife's pussy had just provided another man with an orgasm that was described as 'unbelievable.'

"Do you think you'd be interested in fucking me again before the night is over? Perhaps after the reception has ended?" I asked. I'll admit that I was already feeling a desire for more of the pleasure I'd just experienced and I saw no reason not to pursue it.

Asher's smile provided the answer I wanted. "Absolutely," he said. "I'm all yours."

I moved my pussy a little - just to give him a hint of pleasure - and asked, "I have just one more favor to ask."

"Anything," he replied.

"I'd like to stay in the room while you go back to the reception. I'd like you to find my husband and tell him to come up and see me," I explained. "I'd like to give him a little treat."

Asher smiled. I'd already told him of Milo's desire to be a cuckold, so he was fully on board with the idea that my husband loved that another man had just fucked his wife. In fact, I'm pretty sure that contributed to Asher's enjoyment of the sex we'd had. "I'd be happy to send him up here."

I offered a smile in return and then leaned down to kiss him with a renewed, fervent kind of passion, in part because I was thinking of Milo and in part because Asher's cock still felt so fucking good inside me.

"Good," I said. "And remember, I want you again before the night is over, maybe even multiple times." I'd already cuckolded my husband, so I saw no reason not to cuckold him as many times as possible that night.

"Oh, I'm not going to forget that," Asher replied.

It was going to be a very, very good night for me. The only thing left to do was make sure that Milo was a good cuckold, which meant I was going to do a little bit of training once Asher sent him up to me.

Milo

I saw Asher walk into the ballroom with a big smile on his face. He looked right at me and made a beeline for the table. I wasn't sure why Avery hadn't accompanied him, but the look on his face told me that I'd been cuckolded. The man walking towards me had fucked my wife and he felt damn good about it.

Asher pulled out Avery's chair and sat next to me. He leaned in with that smile on his face and said, "She was spectacular, man. A goddess. And she's going to let me have her again before the night is over. Can you believe that?"

I wasn't sure what to say, so I said nothing. I hadn't expected to talk to the man that had cuckolded me and I truly couldn't find the words. Asher didn't seem to mind, though.

"She wants to see you," he continued. "You'll find her in room 829." He got up, clapped me on the shoulder, and added, "Have fun. I know I did."

Asher walked away with that smile still painted on his face and I grabbed my drink, threw back the rest of it, and left the ballroom. My heart pounded as I headed for the elevators and my hand shook as I reached out to press the button. The shaking was worse as I stepped onto the elevator and hit the button for the eighth floor. I had difficulty stepping into the hallway when I reached Asher’s floor. My fantasy had become reality. Avery had actually fucked someone else and she was waiting in the room where she'd gotten fucked. It was incredible.

I made my way to room 829 and knocked on the door. I waited...and waited...and waited...until I was quite certain Asher was playing a prank on me and Avery wasn't in the room at all. Then the door opened and I saw my wife. Her hair was a little messier than it had been when she'd left the ballroom, but otherwise she didn't look any different. She was still in her dress. Her makeup still looked lovely. It was actually hard to tell that she'd been fucked.

Avery took my hand and led me into the room. The sheets looked rumpled, but that didn't necessarily mean that she'd actually been fucked. It could have been that Asher just didn't bother to make the bed.

Then I saw the condom. It was resting on the nightstand. It was full of cum. It was the condom Asher had used. It was the condom he'd worn while fucking my wife. That condom had been inside Avery and it had been wrapped around another man's cock. That condom had been wrapped around another man's cock while that man had cum while inside my wife's pussy.

I stood there and I stared at the condom. I couldn't take my eyes off of it. It was absolute proof of my cuckolding. It was the hottest thing I'd ever seen. "You did it," I said.

"I did," Avery replied softly. "I cuckolded you. I fucked Asher. Right here in this bed. I wanted him so badly that I didn't even take my dress off."

I turned and stepped back to look at Avery in her dress. It was suddenly so much hotter. I moved closer and reached out to run my fingers over the soft material. Avery looked up at me and smiled. I matched her smile with one of my own and leaned down to kiss her.

"Wait," she said. "I went down on him. I had him in my mouth. My lips...the ones you're about to kiss...they were wrapped around another man's cock, Milo."

I kissed her. Of course I kissed her. What cuckold doesn't want to hear his wife say that her lips were wrapped around another man's cock. Avery seemed to like the kiss as she moaned and immediately reached between my legs to play with my cock. She had me hard in no time and I joined her in moaning.

"You're hard for me," Avery said.

"Yes, I am," I replied. "You cuckolded me. I love that you cuckolded me."

"Do you want me to make you cum?" she asked.

"More than anything," I answered.

Avery unzipped my pants, pulled out my cock, and stroked me slowly. Her fingers were soft and warm and they felt utterly perfect on my exceedingly stiff shaft. "I came so hard...and so quickly, Milo. The moment he slid his big cock inside me I knew I'd cum so fucking hard. It felt so good."

"He was big?" I asked.

Avery nodded.

"Bigger?" I asked.

She nodded again. "He was bigger than you." She looked down at my cock, smiled, and looked up at me once more. "Much bigger than you, in fact."

I didn't really know how much I'd enjoy that particular fact until Avery uttered those words. I loved hearing that, though, and I very nearly came when she said it. Avery must have sensed my orgasm was approaching, though, as she released my cock, stepped back, and sat on the edge of the bed.

"On your knees," she said.

I moved in front of her and dropped to my knees. Avery spread her legs and slowly pulled up her dress, revealing the smooth skin of her thighs. I reached up and ran my fingers over her legs as her panties came into view.

"You may take my panties off," she said.

I slipped my fingers into the waistband of her delicate panties and pulled them off. Her pussy was pink, puffy, and exceptionally wet. I felt like I could barely breathe. I was looking at the pussy another man had just fucked. I was staring at absolute proof that someone else's cock had been inside her. I was astounded.

"You did a good job getting me wet in the bathroom," Avery said. "I took his cock with ease because you were such a good cuckold. Does that make you happy, Milo?"

"Yes," I said as my gaze remained fixed between her legs. "I love that, Avery. I love that you let me prepare you, that I made it a little easier for you to get fucked. I love you, Avery, for cuckolding me, for being such an incredible wife."

She put her fingers under my chin and directed my gaze to her face. I saw a sweet, warm smile as she said, "I love you too, Milo. I'm going to cuckold you again before the night is over. I'm going to let Asher take me to his room after the reception. I'm going to let him have me as many times as he wants. I'm going to cum on his cock over and over. Then, when I'm done, I'll come home to you. I'll tell you all about it. I'll let you taste my freshly-fucked pussy. I'll let you kiss the lips that pleasured his cock. I might even make you cum."

"Can I taste your pussy now?" I asked.

Avery shook her head. "No, you can't. I know you want to. I know you're desperate for it. That's why I'm not going to let you. That's why I'm going to make you wait. I want you desperate for the rest of the night. I want you to prove that you can handle that desperation, for that's part of being a good cuckold. And if you can't be a good cuckold, tonight will be the last night I fuck another man."

I felt a genuine sense of panic at the idea that she might not cuckold me again. As desperate as I was to taste her pussy and to orgasm, I was far more interested in my cuckolding continuing after the first time.

"I'll be a good cuckold, Avery. I will," I said. "I promise."

"Good," she replied. "I'm going to go back to the reception. You can follow, but first I need you to do a few things. I want you to make the bed so it looks nice when Asher and I return. I want you to take his used condom and throw it in the trash. I want you to fill the ice bucket, too, as I think we might get a bottle of champagne. After you've done that, you can return to the reception."

Avery leaned over, gave me a soft kiss on the lips, and turned to leave.

"What about your panties?" I asked as I picked them up.

"You keep them," she replied. "I like the idea of being without them. Maybe I'll let Asher know I'm not wearing them and he can find a way to finger me at the reception. That sounds like fun, doesn't it?"

I nodded, but Avery had already turned to leave. I watched her go and then looked down at her panties and noted how utterly soaked they were. I'm not sure why, but I lifted them to my nose and inhaled. They smelled spectacularly good and my dick throbbed.

I needed to be a good cuckold, though, so I set about accomplishing the tasks Avery had laid out for me. I was going to make sure the room looked perfect for when they returned. I was even going to go ahead and order the champagne for them. I was going to be a good cuckold because I wanted it to happen over, and over, and over. I wanted to be my wife's cuckold, so I was determined to be everything she'd trained me to be.