The Cuckold Training Diaries - Part 13

Click here to read the previous parts of the story.

Avery

I suppose it's possible that not all cuckolds want to watch their wives have sex with another man. I'm pretty sure that type of cuckold is fairly rare, though, and Milo certainly isn't of that variety. He's been clear from the start that he wants to watch, and I can't blame him.

It seems like it would be an entirely different experience to see another man's cock in my pussy. And, given how turned on he got when I told him about fucking Asher at the wedding or when he listens to Alonso and I have phone sex, I figured that Milo would find watching even more arousing.

There is, though, some concern about it being too much for a cuckold to handle. I've read tales of cuckold husbands freaking out when they witness their wives fucking other men and I've chatted with a few women who've warned me that the first time can be overwhelming.

So, in the spirit of training Milo to be a good cuckold for me, I came up with a plan for his first time watching me with another man. First, I decided that Carter - the guy I'd fooled around with in the bar - would be the man to fuck me. I talked to him first, of course, and we ended up going out on a few more dates to ensure that the chemistry was still there. It definitely was, and I actually gave him a blowjob on one of those dates, mostly because he was so good-looking and so charming that I couldn't resist. I would have fucked him, but I wanted Milo there to watch the first time we fucked so I held off.

I'd seen numerous recommendations that the first time be at a hotel, so I booked an exceptionally nice room - I wanted it to be an elegant evening - and let Carter know when and where to show up. I should also mention that Carter was well-aware of his role for the evening. He was more than happy to cuckold my husband and felt perfectly comfortable having sex with another man watching.

I made sure everything was in place before informing Milo of his impending in-person cuckolding. As you might imagine, he was thrilled when I told him. We were in bed. He was naked and I was playing with his chastised cock. I had on this exceptionally soft, delicate pink satin nightie with lace trim and I was cuddled up with him as I teased his locked dick and balls.

"I'm going to cuckold you this weekend," I said.

"Really?" he asked with every bit of excitement you'd expect.

I nodded and kissed his neck. "I've arranged an evening with Carter. After that date where I gave him a blowjob I've had a hard time thinking about anyone else and I can't see any reason to deny myself the pleasure of cuckolding you and enjoying that big cock that I so happily sucked off."

Milo groaned in the way he almost always does when he feels the ache of his cock trying to get hard in its cage. I made sure to kiss him in the hope that he'd think of my lips wrapped around Carter's cock. He groaned again and I like to think that I'd succeeded in directing his mind in that direction.

"There's something else," I said softly. "You're going to watch."

"What?" he asked as his eyes went wide. "Really? I get to watch?"

I smiled and nodded. He was just as excited as I hoped he'd be. "It will be this Saturday. I've booked a room for the night. You're going to join us and you're going to witness your cuckolding for the first time."

"Thank you," Milo said. "Thank you so much, Avery. I can't tell you how excited I am."

I caressed his balls and gently rubbed my fingers over his taint, eliciting a gentle moan from my cuckold husband as I studied his face and the intense pleasure he seemed to feel at the idea of watching another man fuck me. I had a brief moment where I thought of how much things had changed, how the version of my husband lying next to me was so different from the man I thought I'd married. That was a good thing, though, for Milo's eagerness to be cuckolded had helped me embrace what is the most honest version of myself, or at least the most honest version of my sexuality.

"You'll remain in chastity for the rest of the week and on the day of your cuckolding," I explained. "I want you desperately horny when you watch another man fuck me. If you're good - and only if you're good - I'll let you out afterwards and give you an orgasm. If you misbehave in any way, though, you'll remain in chastity for a long, long time. Do you understand?"

"Yes, of course," Milo said. "I'll be good, Avery. I will."

"I expect you to be a good cuckold and help me prepare for my evening, Milo," I explained. "You'll wash my hair and body. You'll shave my pussy to my exact specifications. You'll rub lotion into my legs to make sure they're soft for when he caresses them. You'll dress me in my chosen lingerie. You'll worship my pussy to ensure I'm exceedingly wet for when he enters me. Oh, and you'll purchase condoms beforehand."

Every word I uttered excited him. I could see it in his eyes and I couldn't help but smile, for it was quite clear I'd have no trouble keeping Milo in an excited state leading up to his first in-person cuckolding.

"You are not to play with this cute little chastised cock of yours while you watch," I continued. "You'll be tempted to do so, but I want you to concentrate all your energy on witnessing and appreciating my pleasure and the pleasure of the man fucking me in your stead."

"Of course," Milo replied. "I promise, I'll be good, Avery. I will."

I believed him, though I also knew that he couldn't actually know how he'd feel when he witnessed his cuckolding for the first time. How could any man know how he'd feel until he actually experienced it? After all, it's a unique experience, and one that goes against society's rules about marriage and notions of manhood. That's part of the fun though, isn't it?

"Just remember that it's okay to experience something other than pure pleasure when you witness my joy at having another man's cock inside me, Milo," I said. "That is to be expected. Also remember that it's your duty to deal with those feelings without spoiling my pleasure, and that if you fail to deal with your feelings I will punish you, and I will make that punishment quite severe if you manage to ruin my night with Carter. Do you understand?"

"I do," Milo said. "I won't disappoint you, Avery. I promise."

I certainly hoped he was right, though I was absolutely prepared to punish him if Milo failed to live up to his promises.

Milo

It's really something to step into a hotel shower with your wife and know that you're washing her hair and soaping up her body because she's a few hours away from fucking another man.

I've showered with Avery before, of course, but it was an entirely different experience when we were both thinking about Carter. Soaping up her naked body was unquestionably erotic - just as it always is - but this time she wasn't entirely connected with me. This time she was thinking about the fact that Carter's hands would be on her body before the night was over, that perhaps she and Carter would end up in the shower together at some point.

It's not that she was distracted; it's just that the shower had a different purpose. It was about deepening the cuckolding side of our relationship, and about training me to be a better cuckold, of course.

"Make sure my pussy is nice and clean for him," she said as I rubbed the soap in my hands and reached between her legs. "I want to make a good impression, after all. If the sex is good, I'll certainly want him again, and again, and again, and making sure my pussy is clean and beautiful for Carter is a cuckold's duty."

I washed her pussy thoroughly and then Avery handed me a razor and a bottle of shaving cream and told me to get on my knees and remove all the hair except for a thin landing strip. Honestly, shaving my wife's pussy for another man is one of the hottest things I've ever done. Every second of it was an erotic thrill as I couldn't stop thinking about the fact that I was acting in service of Avery's desire for Carter, the man that would be cuckolding me that night.

After the shower I dried her off, rubbed lotion into her legs to ensure her skin felt impossibly soft, and then she had me go buy condoms while she did her hair and makeup. While it wasn't quite as hot as shaving her pussy for another man, there's something so intoxicating about buying the condoms that I knew another man would be using to fuck my wife. I was thankful for the chastity device, actually, because I absolutely would have sported at least a partial erection while walking through the store, like a teenager about to get laid for the first time.

Avery was nearly done with her hair and makeup when I returned to the hotel room and she looked astonishingly hot. She'd gone for a decidedly sexy look with her makeup and I felt a wonderful ache between my legs as I thought about how she'd done that to impress another man. She almost never did her makeup like that for me, but she'd happily done so for Carter because she wanted to turn him on, to inspire an intense desire in him to fuck her, which would almost certainly make the sex they were going to have even more pleasurable.

I dressed Avery in a simple-but-sexy black lace bodysuit and a pair of high heels and then she had me strip naked, which was how I'd remain for the duration of the evening. I was a little nervous about being naked when Carter walked into the room - it was a hell of a way to meet someone for the first time - but I did as Avery desired.

"Are you ready to watch another man fuck me?" she asked.

I looked up at my wife - who was astoundingly beautiful - and nodded. "I'm ready."

Avery smiled and reached down to pull aside the lace covering her pussy. She was already enflamed with desire and I'm sure she was wet, but that didn't stop her from pulling my lips between her legs. "Be a good cuckold and get me wet for him."

I did my duty. I licked my wife's pussy so it would be wet when she spread her legs for Carter. She tasted remarkably sweet and my cock ached in its cage as I couldn't stop thinking about the fact that someone else was going to fuck her while I watched.

"Mmm, I like that you're moaning," she said. "Does that mean you're turned on?"

"Yes," I replied before quickly returning to her pussy.

"That's good. A cuckold should be excited when his wife is about to fuck another man. He should be eager to witness her pleasure. He should resolve to find almost as much joy in her orgasm as he would in his own," she explained.

I wasn't sure if I'd enjoy her orgasm quite that much, but I was looking forward to seeing Avery cum with Carter's cock inside her. That felt as though it would be the pinnacle of my cuckold fantasy, especially if it seemed like a good orgasm.

"Carter has a beautiful cock, you know," she said. "I found it so pleasurable to give him a blowjob. The head is big and plump and it felt so good to wrap my lips around it and to stroke his long, thick shaft while he was in my mouth. I've spent the whole week thinking about how good it's going to feel to have him inside me, Milo. I've even masturbated to it a few times."

I wasn't aware that she'd cum without me and I honestly felt a little jealous that I hadn't been there to witness it or to provide her with that orgasm while she thought about the man she wanted to fuck. Still, it wasn't my place to be present for all of Avery's orgasms. It was my place to do as I was told, at least as far as our sex life was concerned.

Just before Carter's scheduled arrival time, Avery stepped away, pulled the lace back over her pussy, and said, "Once he arrives, I expect you to stay on your knees and to keep your mouth closed unless you're spoken to. Your only task tonight is to be a good cuckold, and when I'm getting fucked by another man, your role is to watch and wait to be called upon for service. I don't expect I'll need you for anything tonight until we're done fucking, but you never know. You can watch from the foot or either side of the bed, but you will not get in the bed unless invited to. Do you understand?"

I was enthralled with how dominant she was being and I nodded as I said, "Yes, I understand. I'll be a good cuckold. I'll be quiet. I'll watch and wait to be called upon for service if you require it."

Carter knocked on the door a moment later and Avery bent over, gave me a soft kiss, and turned to greet the man that would soon be fucking her. She confidently opened the door and struck a seductive pose in her lingerie, putting a smile on Carter's face. What man wouldn't have a giddy smile on his face in that moment? He was being greeted by a beautiful married woman that wanted his cock more than her husband's.

Avery held out her hand and pulled Carter into the room. The door shut and he pulled her close. They stared into each other's eyes for a few moments and then indulged in a heated kiss as his hands slowly moved down her back and grasped her perfect ass. Avery moaned into his mouth as he kneaded her soft flesh and I could see her mouth open to welcome his tongue. The kissing was way hotter than it had been in the bar the night they met. There was such passion, such desire in the kisses they shared and I felt an intense, almost overwhelming kind of arousal that made my cock ache painfully in the cage.

I felt the first bit of angst when Carter picked Avery up. She let out this delighted sound - it was a mix between a laugh and a squeal - and there was something about Avery feeling something besides lust - in this case, the delight that made her laugh - that triggered a mixture of jealousy and anxiety. It wasn't overpowering, of course, but it was there and it was because Avery had experienced something that fell outside the realm of my fantasy.

He set her in the bed and they kissed as he played with her breasts through the delicate lace of her bodysuit, eliciting a series of wondrous moans from Avery, all of which helped me center in on my fantasy once more.

Then Carter kissed his way down her body and ended up between Avery's legs. She smiled at him as he pulled aside the lace covering her pussy and went to town. I felt the angst again, this time because Avery seemed to love the way Carter ate her pussy. It shouldn't have surprised me that he'd want to go down on her - lots of guys want to go down on a girl to make her feel good - but it still caught me off guard, mostly because I thought of that as the cuckold's job.

Eventually, Carter backed off and stripped. Avery watched as she masturbated - which was exceptionally hot - but once Carter took his shirt off she sat up and scooted to the end of the bed. She reached up and ran her hands over his chest - which was rather muscular - while Carter took his pants off, freeing his big cock.

At first I watched Avery and I witnessed the obvious lust all over her face. Eventually I looked at Carter and I saw that he was, in so many ways, a superior version of a man. Physically speaking, at least. He was taller, stronger, a little better looking, and he had a bigger cock. Of course my wife was excited, and so I felt that angst again, though this time it was fairly potent.

Then Avery slid off the bed and got on her knees in front of Carter. She looked up at him, smiled, and took his cock in her mouth without hesitation. He groaned, closed his eyes, and rolled his head towards the ceiling in the way a man does when he's receiving an exceptionally good blowjob. It was so fucking hot to watch and my cock absolutely ached in its cage.

Then Carter looked at me. It was the first time he'd done so since stepping into the room. He didn't say a word. He simply smiled and put a hand on the back of Avery's head. He didn't seem to be applying any pressure, but she moaned, indicating that she enjoyed that subtle act of control on his part.

I liked it too. In fact, I nearly doubled over from the pain of my dick trying to get hard in the cage. I was embarrassed that I liked it so much, but no one needed to know that. I'm fairly certain Carter liked it too, because it wasn't long until he announced his need to fuck Avery.

She got up, gave him a kiss, and grabbed a condom from the box I'd bought. She rolled it down his cock and they kissed while Avery backed into the bed, spread her legs, and welcomed Carter between them.

I was on my knees at the side of the bed at that point and that's where I remained. I wanted to see Avery's face as Carter filled her for the first time. It was exquisite, too. It was a look of the purest pleasure, like Avery had never experienced something so satisfying, like Carter had made all of her dreams come true by simply sliding his cock into her exceptionally wet pussy.

Witnessing my first cuckolding - the part with the fucking, at least - proved to be an experience unlike any other. I felt the angst. Of course I did. My wife was moaning and groaning like she was having the best sex of her life and it wasn't my cock inside her. I felt the pleasure, though. In fact, the pleasure was far stronger than the angst. I desperately wished my cock was free from its cage so I could masturbate, though of course that's why I was in the cage in the first place. I was meant to focus on Avery and her pleasure, not on my desire.

So that's what I did. I witnessed my wife's pleasure. I listened to her moans. I saw the way she caressed and kissed Carter as they fucked. I saw how she wrapped her legs around him at one point. I heard the naughty things she said to him about how good his cock felt inside her, how good he fucked her, how good he made her feel.

They came together after a fairly long fuck in the missionary position, and their orgasms were far and away the most pleasurable part for me. Hearing Avery's screams of pleasure - which were different than when I make her cum - and seeing the look on her face was incredible. I was more aroused than I thought I'd be at the notion that my wife had made another man cum, too, and I loved the fact that Carter's cock was inside her when he'd climaxed. The idea that her pussy - the pussy that had previously been exclusively mine - had gotten him off was beyond arousing.

Afterwards, Carter remained inside her for a few minutes as they kissed and indulged in a bit of pillow talk about how good the sex had been. Then, finally, he pulled out, rolled onto his side next to her, and Avery looked at me for the first time since Carter had arrived.

"Did you enjoy watching?" she asked.

"Yes, I did," I answered.

She smiled. "Good. That makes me so happy. Did it seem like I had a good orgasm?"

"It seemed like you had a great orgasm," I answered.

Avery turned to Carter, kissed him softly, and said, "I had a perfect orgasm. The kind of orgasm every hotwife wants to have. The kind of orgasm that makes me want more."

"I can give you more," Carter said.

Avery slowly turned back to me, smiled, and said, "This might be a long night, Milo. Can you handle that? It might be hours before I let you out of chastity."

"I can handle that," I answered.

Avery sat up and gently pulled the used condom from Carter's cock before turning to me once more. "I need you to throw this away," she instructed. "While you're in the bathroom, please get us a towel to wipe up some of this sweat, and then I'd like you to fill the ice bucket. And you know what? Call room service and ask for a bottle of champagne. I suddenly feel like celebrating."

As you might imagine, it was rather humiliating to be given orders by my wife in front of the man that had just fucked her, but my job was to be a good cuckold, so I got up, took the used condom, and threw it out. I retrieved a towel and handed it to them and then grabbed the ice bucket.

"May I...may I put on clothes to get the ice?" I asked.

Carter smiled as Avery wiped the sweat off his chest. He was clearly amused that I'd seen fit to ask permission to get dressed.

"The hotel provides bathrobes. You'll find them in the closet. Wear one of those," Avery instructed. "And be quick about it."

I put on a bathrobe, rushed out of the room, and headed for the ice machine as my body vibrated with the pleasures, angst, and humiliation of being a cuckold. I could feel precum dripping from the tip of my locked cock and my legs trembled a little. I was a very happy man, though, and I suspected my pleasure would only continue as the night wore on.