Becoming Melissa's Cuckold Pt. 04

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 and "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 90% 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 cash. 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 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.

"What?"

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!"