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Becoming Melissa's Cuckold Pt. 04

Tags: cuckold,

My relationship with Melissa moves to the next level...

The next morning I woke up feeling hopeful. I'd suffered a terrible humiliation but I think that I managed to talk myself out of it, and I was pretty sure that I could trust both Melissa and Victoria to not tell anyone else about what happened.

I was also happy to learn that it seemed like Melissa was pretty open-minded about my panty fetish. Initially she was furious with me, but Melissa became pretty accepting once she'd spoken to Victoria. Whatever Victoria said, it worked and I'd forever be in her debt for it.

I woke up before Melissa and decided to do something special for her. I made her breakfast in bed. Once I heard her stirring in her bedroom, I told Melissa that I had a surprise for her if she stayed in her room. The smell of bacon cooking probably gave it away, but Melissa appreciated my effort. After making her eggs and bacon, I loaded the dish onto a serving tray with some orange juice and brought it to her room.

While she ate, we laughed and joked like old times. We didn't talk about anything that had happened the night before. We just chilled like best friends. When she was done, I gathered everything together to bring back to the kitchen. Before I left her room, Melissa did something really unexpected. She stood up out of bed -- dressed only in a t-shirt and her panties -- gave me a hug and kissed me on the cheek to thank me. It was the first kind of affection of that nature that she'd ever shown me.

"Clean up, and I'm going to take Victoria's advice and call Diane. We'll talk afterwards."

There was that name again, Diane. I really wanted to know who she was.

"Who is she?"

"We'll talk later, okay?"

I was really curious, but it seemed like if I let things be for now I'd find out soon enough. "Okay"

An hour or so later, we found ourselves sitting in our living room facing each other.

"Last night" Melissa started, "after - you know...Victoria and I had a long talk, about everything and she made me think about some things."


"I feel like things are complicated right now, but Victoria reminded me about someone who might be able to help. You know Philip, right?"

Philip was a guy who occasionally hung around with us. He wasn't exactly a part of our circle of friends, but he was around often enough for me to know who he was. Philip was a big black guy, he was nice to those who knew him but probably intimidated anyone who didn't. I was pretty sure that he was also one of Victoria's fuck-buddies before she settled down with her current boyfriend.

"Yeah, I know him -- why?"

"Have you ever seen him bring an older woman around, she's in her forties but still a really hot milf type? She's always wearing short skirts, has blond hair and big fake boobs?"

I knew exactly who she meant. I'd never spoken to that woman before, but she'd caught my eye more than once when I'd seen her out. She had a bit of an older porn-star look to her and definitely dressed to be noticed.

"That's Diane. Know what she does?"

"No, what?"

"She's a relationship and sex expert - of sorts."

"Really? What do you mean by 'of sorts'?"

"She specializes in counselling couples who live a little differently than other couples do -- 'alternative lifestyles' is what she calls it."

"Um, okay."

"What we have between us, it's a relationship, isn't it? We care about each other, right? You jerk off for me, you perv-out with my panties and who knows what else you get up to. Plus, we live together, we're around each other all the time, we go out together, we eat together, we have all of the same friends - that's a relationship, isn't it?"

"Yeah, I guess so....sort of."

"At first I didn't really think of it as a relationship either. Last night though, Victoria made me realize that I wasn't bothered by what you were doing with my panties. Don't get me wrong, it's weird, but I'm ok with weird. What upset me was that it made me feel like you cheated on me, and if I didn't think that we were in a relationship I wouldn't have felt betrayed like I did."

"I get what you're saying, but this is nothing like a normal relationship."

"I didn't say that it was a normal relationship, just that it is a relationship. I knew a little bit about Diane and what she does but talking to her this morning made realize that maybe what we have is an 'alternative' type of relationship."

"Wait, what did you tell her?"


"What do you mean by everything?"

"I mean everything. She knows about everything that's ever happened between us and she's interested in helping us."

"You told her about..."

Melissa was growing frustrated with and lashed out at me "EVERYTHING! Your little dicklet, your masturbating, your panty sniffing, your cheating, every-fucking-thing!"

"You want me to go to this woman, who knows our friends and talk about all this embarrassing stuff with her? No way Melissa, I'm not going to do that."

"She's a professional! And besides, she already knows everything now." I could sense that Melissa's frustration was turning into anger.

"I don't know..."

"Our appointment with her is this afternoon, I booked it this morning. You're going. Get your ass ready, we're leaving in an hour." And that was that.


Diane had a bungalow out in the suburbs which served as both her family home and office for her counselling sessions. It felt both welcoming and professional at the same time. When Diane met us at the door, she looked totally different than we'd ever seen her before -- dressed conservatively, hair gathered into a bun and for the first time that we'd seen she was wearing glasses.

"Ah, okay -- it's you two!" was her greeting. "I knew who you were when you called me, Melissa, but I wasn't quite sure who Grey was but now that I see you of course I've seen you around. Come on in!"

Diane led us into a room that was right off the entryway to her house. It was a white room with a desk for Diane, a couple of comfy chairs for Melissa and I and a couch that looked like it belonged in a psychiatrist's office. There were some medical looking devices in the room, along with some charts and posters on the wall depicting things like different sexual positions. It more or less felt like being in a cross between medical doctor and shrink's office.

Once we were seated inside, Diane told us about the confidential nature of our visit, that nothing that we would discuss would leave that room and stressed how important it was that we were totally honest with her.

"I got the basics from Melissa over the phone this morning, but it's best that we go over everything together so I can get your input too, Grey."

We gave Diane a complete run down, starting with how we met in high school right up until the night before when Victoria and Melissa caught me masturbating in her bed.

"Okay, so based on everything that you've said to me I have a first little bit of advice for you."

Melissa and I were both eager to hear what she had to say.

"Grey, you need to stop using and taking advantage of Melissa."

I was not expecting that at all.


"You're using Melissa for your sexual gratification and you're taking advantage of your friendship with her to do it."

While I was trying to wrap my head around that, Diane turned to Melissa and said, "And you've got to stop being a doormat for Grey. Be stronger."

I was floored. "Wait, I don't think that you understand...."

"I understand perfectly well," she said cutting me off. "Melissa has given you everything. Your new life, your new friends, your new status and you've done nothing in return for her. On top of that, she makes herself available to you for your sexual gratification, allows herself to be the object of your sexual desire, even gives you her panties so that you can get off and what does she get in return?"

"It's not like that..."

"It's exactly like that Grey. What do you think Melissa?"

Melissa looked as surprised as I was. "I hadn't thought about it like that, but I see where you're coming from."

"Grey, can you think of one thing that you do for Melissa that she doesn't also do for you? I get it, you're friends and you're there for her and you support her and all of that stuff, but she does all of that for you too, right?"

"Yes," I had to admit that it was true.

"So what do you do for Melissa that she doesn't also do for you? We know what Melissa does for you -- she lets you listen to her have sex so that you can get off, she tells you about her encounters and watches you masturbate so that you can get off, you take Melissa's panties from her so that you can get off -- what do you do for her?"

I didn't like how this was going at all. I didn't feel like our relationship was being described fairly, but I was also having a hard time denying or explaining it any other way. More troubling was that I could see that Melissa was warming up to Diane's point of view.

"She likes what we do together, don't you Melissa?"

Before Melissa could answer, Diane jumped in. "Whatever amusement that Melissa gets from watching you do your thing, it doesn't come close to what you get from her, does it?"

"No, I suppose not."

Melissa tried to come to my rescue, "I like the control that I have over his masturbating. I like that when Grey masturbates it's for me -- like a tribute or something. That's kind of thrilling in a way."

"I'm glad that you realize that Melissa, because that's at the heart of your feelings of betrayal. When you caught him masturbating behind your back with your panties it made three things undeniably clear: First, it showed that the control -- the one single thing that you got from Grey - was a lie; second, it showed that Grey was willing to violate your privacy by going through your things and using your panties to get himself off; and third, it showed how everything is about Grey, it's all about him and his masturbation -- you're just there to facilitate his desires. You might not have understood all of that consciously, but your subconscious did and that's why you feel cheated on."

"Diane, you're amazing! I never would have thought about it this way but you're absolutely right!"

I had to try to defend myself, "I don't think that this is entirely fair," I started but wasn't sure how to finish. "You're...I don't know..."

"Grey, if you can offer another explanation I'd love to hear it. The truth is, I've been doing this sort of counseling for a long time now and men are mostly the same and very predictable."

There was a long pause and an awkward silence until Melissa spoke up, "So what do you think we should do?"

"Well, if you guys want to be together it's pretty simple. You've got to start by being stronger. If you're comfortable being objectified by Grey for his masturbation habit, you've got to get something concrete out of the relationship too, something equitable that validates you."

"You mean like take control back?"

"Yes, at a minimum -- that should be a first step."

"You hear that Grey, from now on we go back to how things were -- no more masturbating behind my back, okay? And no stealing my panties either, if you want them you ask for them."

I could tell that Melissa was proud of the stand that she was taking. And all things considered and how badly I thought that this might turn out, I was okay with this resolution. Then Diane stepped in.

"How can you trust him Melissa? Actually, that's a better question for you Grey, how can Melissa trust you?"

"I know that I messed up and I feel bad about that, I won't do it again."

"Right, so the next time Melissa is away for a few days and you're left all alone in your apartment and you know that Melissa's panties are just waiting there in her room for you, you're just going to suppress those feelings and wait for Melissa to get back?"

"Yes" I said, unconvincingly.

"Come on now Grey, we both know that's not true, right?"

I couldn't answer her. I didn't want to agree with her, but also knew that I couldn't argue with her without lying, which she'd call me on. Diane let me stew in the uncomfortable silence. I looked at Melissa hoping for a life-line but it was clear that she was with Diane on this one.

"Can I offer a suggestion?" Diane finally broke the silence.

"Please do!" perked Melissa.

"Have you heard of male chastity?"

I wasn't exactly sure what she meant, but I had an idea and I didn't like the sound of it.

"No, what's that?" Melissa asked.

"There's a whole line of products that are designed to stop men from touching themselves , they're sometimes called 'cock-cages'. It's a device that fits over the male penis, it prevents erections and locks shut so it can't be tampered with."

"That sounds so hot!" Melissa was excited.

"No way Melissa, there's no way I'm going to wear something like that."

"Grey, it's about trust," Diane said. "If you were to get a chastity device and give Melissa the key, she could have the control back that you stole from her when you cheated on her, plus she'd have the reassurance and peace of mind in knowing that you wouldn't -- couldn't -- cheat again."

"Grey, this is fucking hot!" Melissa was lit up. "Nothing would really change, I'd still let you jerk off whenever you wanted to -- you'd just have to ask me first. I'd love that so much!"

"Grey, remember when I asked you what you did for Melissa and you couldn't think of anything? This is something that you could do for her. Think of how excited you get when you masturbate for her, or how excited you get when you get your hands on Melissa's panties. Have you ever done anything for her that's gotten her as excited as she is right now?"

I hadn't, nothing even close to this. Melissa was glowing at the idea of it.

"We should try this Grey, even if it's just for a bit! I need this Grey, you need to do this for me!"

I wanted to prove to Melissa that I could be faithful to her, but I was really worried about having my penis locked up.

"Let me offer my opinion." Great, more of Diane's advice I thought, "I can give you the address of a shop that sells chastity devices. Go and have a look at them, see what's available and see what you think once you have an idea of what they are. Right now, I bet the idea is scarier than they actually are. If you decide to get one, great. If not, well we can explore other options in the future. For now though, I think it's something that you should look into. Treat it like some sexy fun, it should be exciting -- for both of you!"

I somehow didn't think it would be fun for me at all, but I was feeling guilty and did want to prove myself to Melissa. Also, I have to admit that I was a little bit curious -- what were these strange cock cages?

"Ok Melissa, I'll agree to this -- we'll go and have a look. I'm not promising anything else, we'll have a look and see what they're about."

"OMG! This is amazing Grey, honestly this is the best!" Melissa reached across, wrapped her arms around me and gave me a kiss.

We left Diane's place shortly after. She'd given us the address of a sex shop where we could check out chastity devices. I was hoping to head home and give the idea a sober second thought, but Melissa was way too excited and insisted that we went right to the store, so off we went.

The shop was over a half hour away which made for a weird car ride. I was lost in my own thoughts, terrified of what I might be getting myself into while Melissa was beaming the whole time. I'd literally never seen her this happy before. I didn't want to ruin her mood, but I also had to temper her expectations.

"We're just going to look Melissa, don't get too excited"

"Nah, you're going to buy one," she said with a confidence that was beginning to worry me.

"We're just going to have a look."

"Grey, no man with a little penis has ever made me as excited as I am right now. This is the hottest thing ever, and you owe me. You're getting one."

"I don't want you to get too into this idea, Melissa, we're just going to have a look, that's it."

"Nope, you're buying one, you're going to wear it and I'm going to hang on to the key."

She was determined, but I figured that she was still riding a bit of a high from the excitement so I left it there for the rest of the ride.

The shop was in a part of town that I wasn't overly familiar with, but when we spotted the store there was no denying what it was. Out front it had a giant sign that simple read "SEX". It was a small store, but absolutely jam-packed with all sorts of sex toys, pornography, and other kinky things. When we walked in there was only one employee working. She was a beautiful woman, slightly older than us but still young -- maybe twenty-five years old. She was tall and slender with smaller breasts but perfectly proportioned to her frame. She had a bit of a punk look to her with a few noticeable tattoos and piercings visible and super stylish haircut, a brunette with bright red highlights. We'd arrived just a few minutes before the store was set to close for the night.

"Hey guys, just to let you know we're closing in about ten minutes -- if you know what you're looking for, I can help you find it."

"It's okay..."I began to say, but Melissa spoke over me.

"We're here to pick up a male chastity device, a cock-cage?" I was mortified.

"Back corner, left hand side, we have a good selection of them."

Melissa couldn't contain herself and nearly ran to the back of the store while I followed slowly behind her. By the time I caught up with her she'd already had a few picked out and lined them up on the display shelf.

"What do you think, Grey?"

"I think that we came to look and the store is closing soon and this isn't a decision that we should rush into."

"The decision has been made, it's just a matter of which one. Which of these do you like?"

She had a metal one that literally looked like a bird cage, a hard plastic one that was moulded to resemble a penis and a softer silicone one that also looked like a penis. There were a few others on the shelf that she was examining as well.

"Melissa, this really isn't something that I think we should do right now."

From behind us, I heard the shop clerk's voice, "I have a lot of experience with chastity devices if you need some help?"

"That would be great!" Melissa's enthusiasm continued, "what can you tell us about these, which do you recommend?"

"Well, the silicone one is more for play. Most guys can wiggle their way out of that one, so it's more of a toy for casual use really. The metal one is great because when the penis is locked inside there's still enough access to it for teasing purposes, but it's a bit heavy for long term use and it can be hard to hide under some pants. That's why I prefer this one," she said, reaching for the hard plastic one, "my partner wears this, so I have a lot of experience with it. It's great. It's light enough to wear every day, it's got a low profile so it can be worn under most pants without being noticed and it locks shut like a vault -- there's no getting out of it!"
"You said your partner wears one?" Melissa asked.

"Yeah, he's my little cuckold subby I've kept him locked up for over a year now."

That was the first time that I'd ever heard the word cuckold, and I had no idea what it meant.

"Get the fuck out, he's been locked up for a year?"

As she spoke she pulled a necklace out from under her shirt that had a small key on it, "Yup -- a year and...4 months. I let him out pretty often, I just make him earn it!"

"Holy fuck Grey, this is so amazing!" Melissa was enthralled.

"I take it you guys are new to this? My name is Kassandra by the way"

"Nice to meet you, I'm Melissa and this is my...boyfriend? Grey -- and yeah, we're new to this."

"Well, for first timers I'd probably go with the hard plastic shell. Like I said, it's light, it's pretty low maintenance and durable. When you're first getting used to it you can pop it on and off and when you're more comfortable with chastity you can kind of set it and forget it for long term wear."

I didn't like the sound of 'set it and forget it'.

"Thanks Kassandra, you've been an awesome help -- and what a great idea to wear the key around your neck, I think I'll do that too!"

"No problem, I'm going to start closing up but take a few minutes to make the right choice. No hurry."

And with that Kassandra made her way back to the front desk and began tidying up for the night.

"What do you think Grey, I guess we go with the one she recommended?"

"Melissa, I don't even know if I want to go through with this. Remember we just came here to look."

"Stop it. We're getting one, that's final. I like the look of the plastic one, but you have to wear it so you should pick which one you want."

"Fine, get that one -- but don't think I'm going to wear that thing all the time."

"This is really amazing Grey, I'm so excited by this!"

As Melissa was reaching for the package, she stopped when she noticed that there were a few slightly different ones. They all looked more or less the same but some packages had a "S" on them, some had an "L" but most didn't have anything on them at all.

Melissa shouted over to Kassandra, "What do the different letters mean on the package?"

"Oh, those are the sizes. For almost all guys, the one without a letter will fit fine. They're all adjustable so that one fits like ninety percent of all guys. If you're exceptionally big, get the "L" model or if you're exceptionally small get the "S" model. Really though, the regular one should be good. Just go with the L or S if you're really big or really small".

Great, I knew what was coming and tried to prevent further embarrassment. "Mel, let's just get the regular one, ok?"

"But what if it's too big for you?"

"She said that they're adjustable and fit 90% of all men, it will be fine"

"I don't know..."

"Having a problem over there?" Kassandra called out.

"We're good, thanks," I said.

Then Melissa called back, "How small is small?"

Kassandra held up her pinky finger, "Like really small."

"I think we should get the small one babe," Melissa said, looking up at me.

Kassandra sensed our uncertainty and came back over to us. "If you have a look on the back of the package there's a size chart if you know your measurements."

The three of us stood there looking at the size chart and I realized that I did indeed need the smaller size one. I was humiliated, but wanted to get out of there. Melissa knew that I was small and I was never going to see this Kassandra woman again so I just reached for the "S" model without saying a word and walked to the register. I was sure that I heard the girls giggle behind me, but I didn't turn around to look.

After Kassandra rung us up, she gave me a small lock, "That's for you," and gave Melissa the keys, "and those are for you. You're all set now, have fun!"

"Pull the car around Grey, I'll wait here for a minute."

The girls were exchanging odd glances and mischievous smiles, and I figured that was because of the "S" model thing. At that point I didn't care and just wanted to be out of there.

I got the car and pulled up in front of the store. I could see Melissa and Kassandra chatting away inside, and could see that Melissa had bought something else. She came out carrying a bag and was careful to keep its contents hidden from me. "Just a few things for myself, maybe for us -- we'll see," she said when I asked her about it.

During the ride home I had a real sense of how excited Melissa was. She seemed lost in her thoughts, probably playing out various scenarios in her head. I was still full of apprehension. I didn't like what I'd gotten myself into with this chastity device and I was still mentally going over some of the things that Diane had said. I thought of a lot of things that I'd wish that I'd said to Diane -- like how it was Melissa who made me masturbate for her, how it was Melissa's idea for me to do it in front of her, how she decided to involve herself in how and where I masturbated. Had I really been taking advantage of Melissa? The more that I thought about it the more I realized that almost everything was done by Melissa's decision, not mine. I didn't want to do most of the stuff that we did, Melissa just took control of the situation and I gave in like I always do. She took control of my masturbation habit - I didn't force that on her. I didn't want to go to see Diane, but Melissa did, so I went. I didn't want to buy this stupid chastity device but Melissa did and here I was looking at it on the seat beside me on my drive home.

I was thinking of all of these things when I looked over at Melissa, and all of my independent thoughts melted away. I was looking at one of the most beautiful women in the world and I knew how lucky I was to be with her, and knew exactly how grateful I should be for everything that she'd done for me -- Diane was right about that. I loved how happy she was in that moment, and knowing that I was the one who made her that happy was an amazing feeling that filled me with pride. If actually wearing a stupid chastity device for a bit excites her as much as the idea of it does, then so be it. I realized that I loved making Melissa happy and knew that I was lucky to have the opportunity to be in the position that I was in. It also hit me that when we were in the store and Melissa was talking to Kassandra that she called me her "boyfriend", even if she hesitated for a second when saying it. In the stress of the moment, I'd let that slip by, but thinking about things here in the car she clearly said it, did she really mean it? Earlier that day we'd gone to a relationship expert, and now she was publicly referring to me as her boyfriend. Was I really Melissa's boyfriend, was she my first real girlfriend?

All of these thoughts were running through my head and I kept looking at Melissa, she was still glowing, and happy and excited and...."I love you," I said out loud, the words just slipped out of my mouth.


I instantly regretted saying it. "I just mean that, you know... I'm doing this because I can see how happy it makes you and I want to make you happy." I was back peddling a bit.

I could tell that Melissa was having a hard time processing what I'd just said, she was some combination of shocked, surprised, and completely caught off guard.

"Whoa," Melissa said looking stunned but smiling - maybe in disbelief, "where'd that come from?"

"I dunno. Some of the things Diane said bothered me. I need you to know that I care about you."

"You understand that we can't like be together for real, right? I need to have sex with guys who know how to fuck me and that's never going to be you."

It was crushing to hear, but I knew it was true -- Melissa was way out of my league, I'd always known that. "I know, but we can still do what we do." I could tell that her mood was changing and that I might have ruined the high that she was on. Wanting to get her back to what was exciting her I added, "But it will be even better now because we have this," I said pointing to the chastity device.

She perked up again, I think choosing to ignore the 'I love you' that I'd just caught her off guard with. "I really can't wait, this is going to be so amazing!"



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