I left Melissa at Tayshaun’s place not sure when she’d call to have me come and pick her up. When I got home, I did everything that I could to not think about what was happening but it wasn’t possible. Every time I looked at my watch I’d think, 'Oh, an hour in, they’re probably in his bedroom now, maybe she’s blowing him?'

Fifteen minutes later, 'he’s probably returning the favour and going down on her now.' Once Melissa had been there for a couple of hours, I knew that he was fucking her and I couldn’t help but think of what position they were in. Maybe he was on top of her? Maybe she was on top of him? Maybe he had her bent over?

My thoughts were driving me crazy, and the emotions that I was feeling were too. I went through a rotating series of feeling jealous, then angry, then hurt, then aroused, then happy for her… then back to jealous.

All of these thoughts running through my head weren’t good for my locked up penis. Even the worst of what I was feeling inside couldn’t stop the blood rushing to my penis. All of the pain, anger and jealousy couldn’t suppress how turned on I was by everything that was happening. The chastity device was driving me insane. I was desperate to masturbate, and distracting myself was an impossible struggle.

I’d sat in front of the TV and watched a movie from start to finish and for the life of me I couldn’t remember a single thing about it. I was zoned out completely, lost in thoughts that I didn’t want to be thinking. My mind was elsewhere and no TV movie of the week was going to get my mind off things.

Melissa had been gone for more than four hours and it was after 1 am at this point. I was tired but didn’t want to fall asleep. Around 2 am, I moved the phone beside our bed and laid down for a bit, pretty confident that the phone would wake me up if she called. I slept right through to the morning.

That morning, I went through all of the thoughts and feelings that I’d gone through the night before, but they were even more intense. Perhaps from emotional overload, all of my feelings just collapsed into one feeling – I missed Melissa and I wanted her to come home. Which made me worry, did I miss her call?

I was certain that a ringing phone beside my bed would have woken me up, so I had to guess that she fell asleep at Tayshaun’s house. It was approaching noon though and I still hadn’t heard from her, so maybe something else was up? Then right on cue, the phone rang. It was Melissa asking me to come pick her up.

I was nervous on the car ride over to Tayshaun’s house. I had an anxiety deep in the pit of my stomach. I wanted to see Melissa and hold her. I needed to know that nothing had changed between us while also wondering how it would be possible for things to not be different. Melissa was my girlfriend now, we’d said “I love you” to each other… and yet she just spent the night fucking another man, one who clearly didn’t think much of me and might try to steal Melissa away from me.

When I pulled up to Tayshaun’s building, he was standing outside with Melissa. He had his arm around her shoulder and she had both of her arms wrapped around his waist. Anyone who saw them would assume that they were a couple. That hurt.

Seeing my car pull up, Melissa leaned up to kiss Tayshaun and he bent down to kiss her back. I couldn’t tell from where I was, but I got the distinct feeling that Tayshaun was looking at me when he kissed her. Satisfied with one last kiss, Melissa began walking towards my car. This would have been a ‘walk of shame’ for anyone else, but Melissa had a thrilled look on her face.

She was barefoot, carrying her heels, her hair was tied up in a morning-after bun, her makeup look slept in and she had the tipsy walk of someone who might have had a little of last night’s booze still in her system. Despite all of that, Melissa was glowing, as happy as I’d ever seen her.

She said hello as she got into the car she leaned in for a kiss. I hesitated.

“Don’t you fucking dare.” The look in her eye was a warning.

I kissed her, wondering what of Tayshaun’s might have still been on her lips.

“Drive,” she said as she rolled down the window and waved to Tayshaun.

“So…” I began, not sure where to go from there.

Melissa cut in, “I don’t know if you want to know or don’t want to know what happened, but either way I don’t want to talk about it right now. I only got a few hours of sleep. I want to get home, get washed up and have a nap before we talk about anything at all.”

To emphasize that she didn’t want to talk, Melissa reached for the car radio and put it on at a loud enough volume to discourage conversation.

When we got home, Melissa went straight to the shower and asked me to make her some lunch. By the time lunch was ready, she was already out of the shower and I presumed getting dressed in her room, but when I went to check on her she’d fallen asleep – still naked from her shower.

I put her lunch in the fridge and decided to let her sleep. I was worried about how things were going to go when we started talking so I wasn’t too upset that she’d passed out and delayed things for a bit.

A few hours later, the phone rang. I jumped to answer it before it woke Melissa, but the phone was still beside our bed from the night before. It turned out to be Kassandra, calling Melissa to find out how her night went. Not satisfied to talk on the phone, Kassandra invited herself over to our place to get all of the details. I wasn’t happy about that at all.

Melissa and I still hadn’t spoken and the last time I saw Kassandra she was selling me a chastity device – and knew that I needed the small one. Now Kassandra was coming over to my house to listen to my girlfriend tell her about the guy that she fucked last night – a guy that Kassandra hooked Melissa up with.

Melissa said, “Kassandra is going to be here in a bit. We have some time to talk if you want to?”

“I don’t know if I want to know what happened, I just want to know that we’re still good?”

“Of course we are! Don’t be silly! Last night was just sex, that’s it. Tayshaun doesn’t mean anything to me and you mean everything to me. Is that what you’ve been worried about?”

“Yeah, I mean… you were so into all of his ‘alpha’ stuff, and he was a bit of a jerk to me and that didn’t seem to bother you. You seemed to love it actually - and then seeing you holding each other this morning… yeah, I was worried.”

“Aww Grey,” she leaned in for a hug, “you have nothing to worry about. You’re my boyfriend, you’re who I care about. Tayshaun or whoever else is just sex, that’s all they’ll ever be. And if I got carried away with his big alpha moves last night, it’s just because it turned me on so much… I don’t always think straight when that happens, so maybe just ignore me when I get like that, okay?”

I wanted to ask her why it was up to me to ignore her and not up to her to mind what she said, but I was happy and relieved with everything else that she said so I let it be.

“Okay.”

“You thought Tayshaun was a jerk?”

“Yeah, kinda. I had an idea of what to expect when I spoke to him on the phone, but maybe I thought that he was playing things up… he said he was trying to lay down some ground rules…. but the way he looked at me and the way he spoke to me last night…. it just felt like taking you from me wasn’t enough, he wanted to rub it in too.”

She continued, “Well, first off he didn’t take me from you. You prepared me for him and gave me to him, and you did it because that’s what I wanted – I’m in control of this situation, not you or him. As far as how he treated you, I didn’t really notice but I’ll have a talk with him because I’m definitely going to see him again. This was our first time stepping into this world and we both have a lot to learn. I’m sure there are different ways of doing this, and if this one wasn’t right we can find one that is.”

I felt somewhat reassured that Melissa seemed willing to compromise a little, but I wasn’t thrilled with her insisting on seeing Tayshaun again. He humiliated me and really seemed to like doing it. I wasn’t convinced that was something that could change.

“And don’t worry, I haven’t forgotten about the special reward that I promised you if you were good – and you’ve been very good about all of this. Once Kassandra is gone, you’ve got something very special to look forward to!”

My penis twitched in its cage at the look in her eyes when she said that.

“Are you going to stick around when Kassandra is here? It looks like we’re going to be friends so you can’t avoid her forever, but I understand if you don’t want to hear about last night.” She paused for a second, then continued “or… it might make later on a little more special. You used to stroke your little guy while you listened to me getting fucked, maybe now listening to two girls gab about it will prime you for later?”

She was giving me a choice, but it felt like I didn’t really have a choice. “I’ll be here.”

Melissa ate the lunch that I’d made for her and started to get dressed while I tidied up for our guest. Not long afterwards, Kassandra showed up at our place. My heart raced a little when she knocked on our door. It was going to be weird to be in the same room as someone who knew that I was in chastity and knew that Melissa slept with other guys. Melissa was still getting ready and yelled for me to answer the door.

“Hi, umm… ” my words lost me.

Kassandra said, “hello,” with a mischievous smile on her face and stepped inside.

“Melissa is still getting ready. She’ll be out in a few minutes. Come on in, I’ll take you through to our living room.”

Kassandra didn’t speak, instead, she just smiled her knowing smile as she looked at me, apparently loving my discomfort.

I thought Kassandra was beautiful the first time that I saw her, but she was even more beautiful the second time seeing her. Even though she worked in a sex shop, she apparently toned things down and dressed semi-professionally for work. Now on her own time, she was far less modest – dressed in a plaid skirt, knee-high socks, high-heels and a flimsy blouse tied up so it barely covered her breasts and left her midriff totally exposed. She carried a purse that was more of a carrying case that gave her school-girl look an approximation of a lunch box to top it all off.

I led her to our living room and asked her if I could get her anything.

“I’m ok thanks, I have a bottle of water with me. That will do for now.” She hadn’t stopped smiling and was staring me down with a Cheshire cat grin.

I knew that it was going to be awkward, but I didn’t realize how awkward. She dove right in.

“So, buying the small-sized chastity turned out to be the right decision then, eh?”

“It’s tight,” I said trying to regain some ground, “but I guess it’s supposed to be, right?”

“The normal size one is usually tight too, for most guys anyway.”

She was toying with me like a cat does a mouse. I got the distinct feeling that she’d been down this road many, many times before and I wasn’t going to win this battle.

“I guess this one suits me fine.” It was easier to resign than to escalate things.

“And you’ve adjusted to being locked up? That couldn’t have been easy could it?”

“It took some getting used to, but it’s okay now.” I was lying to myself as much as I was lying to her.

“As I understand, you weren’t using it much anyway. I’ve never put a virgin in chastity before. Maybe not knowing what you’re missing makes it a little easier. Still, though, you’ve been beating off non-stop for the last, eight or nine years? And now you have to get a woman’s permission to jerk it, that can’t be easy for you?”

'What else had Melissa told her?' I was trying to hide my anger and embarrassment, but I must have been blushing by this point.

“Melissa has been good to me… ” I began before Kassandra cut me off with “… but she’s been even better to Tayshaun.” The devilish smile on her face made it clear how much she was enjoying this.

If I wasn’t before, I was definitely blushing now. I didn’t know how to respond to her. I wanted to leave but didn’t want to give her the satisfaction of feeling like she’d beat me.

“I’m just playing with you, Grey. I trained my cuck years ago, so I know what you’re going through. I’ve seen my guy go through it all. Mind you, he wasn’t a virgin and he has a nice sized dick so it was different for him.”

I sensed a slight change in her demeanour, maybe pleased that she’d put me in my place.

“Hang in there, the cuckolding lifestyle can be really rewarding if you’re open to the experience.”

There were those words again, cuck and cuckold. When Melissa and I first met Kassandra in the sex shop, she referred to her partner as her ‘cuckold subby’ and last night Tayshaun called me ‘cucky-boy’. I was starting to piece it together, but still wasn’t sure exactly what it meant.

Already feeling a little bit like a fool, I didn’t want to ask Kassandra any questions.

“Hey Kassandra, thanks for dropping by! What are you two talking about?”

“I think Grey was about to ask me something?”

“Umm… no, I don’t think so.”

“Okay… well then, why don’t you tell me what I came here for? Give me all the dirt about last night!”

Melissa came over and joined Kassandra and me on the couch, we had been facing each other and Melissa sat between us with her back to me.

“Oh my God! He was SO good!”

“Did he make Grey prepare you?”

“Yes! How hot is that?!”

“That’s one of his moves, the women love it but the cucks usually get butt hurt over it”

Melissa turned to me “Sound familiar Grey?”

Kassandra laughed. “Aww did someone get a little pouty last night?”

“So anyway, Grey got me ready and brought me over to his place. I went inside and I tried to play it casual but it was strange because we both knew that I was there to fuck. He had a bottle of Champagne waiting for us…”

“That’s SO Tayshaun, Mr. Smooth!”

“Yeah, totally smooth. The lights in his place were dimmed and the whole condo was candle-lit. Everything was perfect. So we had some Champagne and I really just wanted to jump him but I wasn’t really sure how these types of dates were supposed to go. We were defining vibing each other though, the chemistry was SO there. Then more or less out of the blue in the middle of some small talk, he just cut me off, took my Champagne from my hand and told me to suck his dick.”

“You didn’t have to be asked twice did you?”

“No of course not! If any other guy did that I’d be creeped out, but for Tayshaun, I just got down on my knees in front of him.”

“Tell me honestly, what did you think when you pulled his cock out?”

Again Melissa turned to include me in the conversation, “Grey, Tayshaun’s cock is massive. Not just big or whatever, it’s massive. He’s got a monster cock. It’s the size of my forearm.” She held her arm up to help me visualize something that I didn’t really want to.

“I’ve measured it, it’s ten inches”

“I believe it, and so thick too!”

“I told you!”

“Anyway, so I sucked him off in his living room for a bit. It was really hard to fit in my mouth but I couldn’t get enough of it. It was less of a blowjob and more of cock-worshipping session, I just grabbed it with both hands and put the head in my mouth and took as much of it as I could.”

“He’s told me that a lot of women have had problems blowing him.”

“Yeah, I can see why – but not me! I sucked his cock for a bit and he reached down and grabbed my arm, lifting me back up to my feet, then picked me right up and threw me over his shoulder and carried me off to his bedroom.”

“Like a caveman claiming his prize!”

“Exactly! It was so hot! I took my skirt and top off and climbed into his bed waiting for him to finish getting undressed. He’s got the most perfect body I’ve ever seen! Sculpted muscle from head to toe, with a giant cock between his legs.”

“I told you! I know a lot of bulls, but as soon as we started talking I knew that Tayshaun was the right one for you!”

“He tore my panties off, like, literally tore them off. Foreplay wasn’t really needed, I was soaked and so desperate for his cock, but he buried his face between my legs and went to work on me with his tongue anyway. It was the best ever!”

Hearing all of this was really hard. It hurt me to think of my girlfriend doing all of these things with another man that she wouldn’t do with me, and also painful because, as much as I didn’t want to be turned on by what she was saying I was. Kassandra wasn’t helping either.

With Melissa’s back to me, Kassandra was facing both of us but constantly making eye contact with me. When Melissa said something particularly graphic, Kassandra would look at me for my reaction. Again I wanted to leave, but I left like Kassandra was judging me and for some reason, I wanted her approval. Lost in my own thoughts, I’d missed part of Melissa’s account of the night before.

“… and then he got me on my knees and just pounded me from behind. He’s so big and so strong. I had this scary feeling of not being in control at all but also loving it and not wanting it to stop. Good thing he didn’t stop! He used his cock to stake his claim on my pussy and he made it his own. He did me like that for a nice long time and then without notice, he picked me up, spun me around and onto my back and absolutely sprayed me with his cum. I was covered in it.”

“Sounds like you had a great night!”

“That was only round one! We went at it all night! There was so much fucking I only got about two hours of sleep.”

“Wow! I’ve sent a few girls Tayshaun’s way and as much as they love it a lot of them can’t keep up with him. It sounds like you’re the perfect match.”

“Definitely. It was the best sex I’ve ever had, like for real. I’ve been with a lot of guys who knew what they were doing, but Tayshaun was better than all of them. That feeling he gave me… he stretched me out so much and made me feel so full too. I’ve never been so satisfied before.”

“Well, I’ll get his side of the story but I’m sure he liked you as much as you liked him. I’m glad that I was the match-maker here!”

“I can’t thank you enough!”

“How about you cucky? Are you happy that I introduced Melissa to Tayshaun?”

Apparently, my battle of wills with Kassandra wasn’t over yet.

“Yes, thank you. Melissa had a great time and I’m happy for her.”

Melissa turned to face me. I think she wanted to see my face because she couldn’t quite believe what I was saying. I must have been selling it well.

Melissa gave me a kiss on the cheek and said, “Tayshaun isn’t the only perfect match in my life.”

It felt good to hear that, but of course, Kassandra had to pour salt on it.

“Yeah, finding a boy who will let you find a man is definitely something special.”

Kassandra stayed for another couple of hours or so, but luckily about a half hour into to her visit the phone rang and it gave me a reason to leave the room without letting Kassandra feel like she got the better of me. When she finally left, I pretended to still be on the phone and shouted “goodbye” to her through our closed bedroom door.

Once Kassandra was gone, Melissa joined me in our bedroom.

“Wait,” she said, “before you get upset I want you to know that unlike last night with Tayshaun I wasn’t oblivious to that tension between you and Kassandra.”

“I’m glad you noticed. I don’t know why she took that attitude with me though – it was right from when she walked in the door, I didn’t do anything to her.”

“I know, and like I’ve told you she and I have done a lot of talking and she’s taught me a lot of things. She’s just a little more extreme with her cuck than I am with you.”

“Before we go any further, these words keep getting thrown around and I want you to explain them to me.”

“What words?”

“Cuckold, cuck, cucky, cucky-boy…you’ve talked about this ‘lifestyle’ and this ‘world’… what exactly are we mixed up in?”

“Oh wow, I guess I’ve taken for granted that you had all of this figured out. I didn’t know everything from the start either, but I was able to figure it out from context – and from talking to Kassandra, she really helped a lot too.”

'Yeah, great help she’s been.' I thought it, but didn’t say it.

“Where to start? Okay, well you’re a cuckold, especially after last night. I guess that made it official in some way.”

I’d managed to piece that together on my own. “Right, but what exactly does it all mean?”

“A cuckold is someone who’s with a woman who prefers other men for sex. You know what swingers are, right?”

I nodded “Yes.”

“It’s like we’re swingers, but only I swing. In the cuckolding lifestyle, I’m what’s usually called a ‘Hot Wife’. Since we’re not married, I don’t know if that’s the best word for me or not. And I mentioned yesterday that guys like Tayshaun are called ‘Bulls’. That’s the basics really.”

“That’s kind of what I thought, but I’m glad it’s all clear now.”

“Well, the basics are anyway. There’s a lot of variations in the cuckolding lifestyle. We’ll have some fun and experiment with it and find out what’s right for us.”

I wasn’t sure if that was exciting or ominous, but it was enough for now.

“You were about to tell me that Kassandra was a little more ‘extreme’ with her boyfriend?”

“Her cuckold, yes. I think you should get used to that. Embrace it, you’re my cuck.”

I was trying to understand all of this, and realized now wasn’t the time for an argument. “Okay.”

“So, the reason Kassandra was a little mean to you is because she has a different sort of relationship with her cuck. In addition to having a cuckolding relationship, they’re also heavily involved in the BDSM lifestyle too.”

Again, I had some understanding of what that meant but didn’t truly have a full grasp of it. Melissa could see my confusion and launched into an explanation without me having to ask.

“We have our thing right? And that’s it. Things are different with her and her cuck. She doesn’t respect submissive men. They’re like pets to her, so she talks down to them. She started off in a normal relationship with her cuck, but she tested him and he kept backing down. Now she doesn’t just walk all over him, she does some downright bizarre things to him… I guess with him, he seems to like it.”

I was curious, but also afraid to ask. Curiosity got the better of me. “Like what?”

“Well, for starters she makes him call her Mistress, all the time – even in public. He’s not allowed to say her name. I went over to their place a few days ago – Kassandra had a picture of Tayshaun that she wanted to show me. When I was there her cuck, was all like, “Yes Mistress,” “Of course Mistress,” “Anything you say, Mistress,” – that sort of thing.”

“That’s odd.”

“That’s nothing. He doesn’t sit on the furniture and he sleeps in a cage.”

“No way.” I couldn’t believe what I was hearing and was half wondering if Melissa was putting me on. “He sleeps in a cage? What kind of cage?”

“I dunno, I guess it’s made for big dogs or something. It’s in their bedroom.”

“That’s fucked up.”

“Yeah! There’s more, a lot more – all kinds of crazy shit!”

“Whoa, that’s messed up.”

“Right? That’s why she took that attitude with you. I think her relationship with her cuck has clouded her view of all submissive men. She thinks that I’m too easy on you.”

“You think I’m submissive?” It hadn’t occurred to me before.

“Grey, you’re wearing chastity and you let me control your orgasms while I fuck other guys on the side.”

I’d never thought of myself as being submissive, so hearing her put it like that came as a bit of a surprise. I thought of submissive guys as being weak and wimpy, maybe nerd types, but that wasn’t me at all really. However, it did explain why I always gave into Melissa, why she always got her way, why when I had opportunities to stand up for myself I didn’t. A lot of things were starting to make sense.

“Don’t worry, I’m not going to make you sleep in a cage at night. There will always be a place in my bed for you. Unless another man is fucking me, of course,” she said with a smile, then added, “but she does have some good ideas.”

That had me worried. “I can deal with what we have going on now but I’m not going to do any of that crazy stuff, Melissa.”

“And I don’t want you to either, I’m not like Kassandra. But she gave me some ideas that I want to try out… we’ll see how they go.”

Again hearing that made me nervous, and it probably showed.

“This is a lot for you to take in, isn’t it?”

“Yeah, but I want to be with you, it’s just that last night was rough for me. Mostly because I was worried that you might leave me for Tayshaun.”

“That’s not going to happen Grey! I’m with you because I want to be with you. Obviously, I have my choice of men, but I chose you. You know who I am and how I want to live, you’ve got to figure out if you’re the right man for me.”

“I am Melissa, I swear. It’s just that…”

“Spit it out!”

“We’re going to be together for a long time right? I least I hope so.”

“Yes, of course! Stop worrying about some bull sweeping me off my feet – I want to be with you, those other guys are just sex.”

“That’s the thing though. I’m a virgin, and we’re going to be together for a long time… and you don’t want to have sex with me. I mean, how long…”

Melissa clued into what was bothering me.

“Ah, I see where you’re going. Well, Kassandra gave me an idea, and it’s one that I think that you’re going to like.”

This sounded really hopeful, but knowing that Kassandra was involved had me worried.

“You haven’t forgotten about your special reward have you?”

I couldn’t believe it, but with everything on my mind, I had. Hearing Melissa bring it up instantly made me aware of how frustrated and how desperate I was to masturbate.

“I had something planned, but when you were in our room hiding from Kassandra, she managed to convince me to do something else. I’m trusting her on this because it’s not something that I ever would have done without her talking me into it.”

“Are you going to tell me?”

“No, I’m going to show you.”