Maybe Day

All posts tagged Maybe Day

Cagedmonkey wrote the other day about “Maybe Day” and his thoughts on it. He asked me how I felt about his post since it wasn’t something we had talked about with each other. I figured I’d respond here. Honestly… I don’t know how I feel about it. I have known my hubby for 16 years now and he’s never been ok with the unknown. In a way it makes me feel good that he’s grown and in a place now where he trusts me so much that he would be ok with doing away with Maybe Day. I love that he’s gotten here with us and our relationship that he would be ok with me just deciding when, where, how, and if he ever came again without giving him the whole “it’s supposed to happen this day” thing. I could always change my mind and make it happen before or push him longer. It is ALWAYS my decision when but we always had that goal or that “finish line” if you will. I feel like maybe it gave him something to look forward to so he worked to get there. I started to worry a bit that if he didn’t have that date to look forward to he would just eventually give up on trying or even wanting an orgasm. I do LOVE the desperate need to have one when he’s denied and teased and aching. Then again I guess it would sort of be the same as always because ANY day could be maybe day.


So really this post probably accomplished nothing as I honestly don’t know how I feel – I guess I’m a little worried and a lot happy, like I said, it feels good to know that his trust has grown that I would not just NEVER give him one again or that I would ever lock him up and leave him. It feels good knowing that he knows that would never happen. That I need him just as much as he needs me. That I love our intimacy just as much as he does and I crave feeling him. I actually do enjoy making him orgasm and giving him that pleasure but I enjoy teasing the fuck out of him and denying him just a wee bit more – that’s why he is locked up, teased and denied a whole lot more than he is given orgasms!! 🙂

The other day I wrote about how I was taking a break from setting a “Maybe Day” for cagedmonkey. I got quite a few comments on the post, all of them kind of referring to the same thing, so I thought I should clarify a few things. I don’t want there to be any mistake about who is in control at any point in our relationship. However, a relationship is about two people and you need to do the things that work for each person so that emotionally and physically there is fulfillment.

Let’s back up some and get a little more personal. Cagedmonkey has allowed me to explain a few things about his childhood so you all understand him a little more. When hubby was a child his mom was very much a “don’t rock the boat” type person and he was more on the high strung side. As a way to avoid confrontation (or hubby having a temper tantrum lol) his mother would say things like “maybe later” or “we’ll see” never really giving him a straight answer. She didn’t want to be the one to tell him “No,” because he might get upset. It was sort of drilled into him that those “maybe’s” and “we’ll see’s” always meant no. Cagedmonkey is also the type of guy that needs to know that SOMETHING is definitely going to happen or not happen and SOME kind of time frame that it is going to happen or not happen in. Even if that time frame is “Yes, you WILL cum 3 more times in 2015” that gives him something to depend on. Whether or not he cums 9 times or only the 3 he has something to hold on to. He was pushed off by his mother and it felt like he was lied to so much as a child as a way to appease him that now as an adult he really does need to have something he can count on to ease his anxiety.

So, as I said, I got a few comments on my last post, like this one from one of my favorite ladies…

Mistress Marie said:

I love that you are changing this as this is how it really should be, you in full control with CM being clueless to know what your thoughts are on when he will cum. I think this is great because any day can be maybe day this way and he will never know.

I wanted to make sure that I addressed these comments because they make it seem like giving Cagedmonkey a “maybe day” is somehow taking away my control. This is entirely not true. I am in full control of his orgasms and sexual pleasure and I can give him and orgasm or not whenever and however I please. He is always clueless as to when I may make him cum. Heck, sometimes I’m clueless because it might creep up on me that I want him to! 🙂 Just because he has a maybe day does not mean I am stuck denying him until a certain date. I could give him a maybe date of July 4th and make him cum 5 mins later. The maybe day is a comforting thing for his anxiety and can be a challenge for me and him at times too.  Our last maybe date was set out at 6 months from his last orgasm. I wanted to try to push him (and myself) to 6 months of denial. I obviously didnt make it but that was MY choice because, after all, I am in control and I made the decision to allow him to cum – which was more for my pleasure than his. I didnt do it for him, I did it because I missed feeling him explode inside me. I missed feeling his body as he was cumming. I missed seeing his face and watching him enjoy that orgasm.

Since I told Cagedmonkey about needing the break he’s been very anxious, asking a lot of questions, making sure I’m not just pushing him off. He really was having trouble with the way things were up in the air. He really needs something solid to hold on to to function properly. I love that I know this about my hubby and while I did the up in the air thing on purpose to test out if he could handle it, I found a way to help him emotionally while leaving me to not deal with a maybe date. In other words, I found a loop hole of sorts to ease his anxiety. lol

I have decided instead of a maybe day where I’m trying to deny him until a certain date or time frame that I would simply give him an idea of what to expect for the time being. I explained to him that he could expect to be locked everyday, especially on his work days. He could expect to be denied but likely not more than a week or two and if I was enjoying myself and felt it would go longer I would tell him. He could also expect to be teased and tormented daily. I certainly do enjoy the build up of horny and I love that week to ten day point where it is at a high. That’s why at the moment his denial probably wouldn’t be much past that. I also told him he could fully expect that I could unlock him, use him and make him cum at any time during any of this. This seemed to go over very well and he seems to be much more calm about things and had stopped obsessing over when and how long, etc. Of course, this really is how it is EVERY day but it seemed to REALLY help to have me actually say the words and explain it out right to him. All of those things have been understood since we started all this but I think hearing them and seeing them written helped to give him that thing he needs to depend on and hold on to. He knows that I wont just tell him “we’ll see” and then not having something happen one way or the other. Cagedmonkey is just not that guy when we’re having sex and he asks “please may I cum, ma’am?” who can be told “maybe, baby.” He really needs a “yes, but not right now” or a “No, not tonight” answer.

I hope this helps clarify why we need to have a maybe day. Even if it kind of has no meaning (unless we are using it as a challenge for both of us) because, I control everything about his sexual pleasure anyway, it helps him mentally to know I’m not going to flake out on him like his mom would often do.



My Lady and I don’t use a specific “release date” like some people do, because we feel it takes some control away from her. What if, for example, my release date comes and ML wants to keep me in chastity juuuuuuust a little bit longer? Is she obligated to give me an orgasm? Or, what if it’s not release day yet, and she just REALLY needs to have her cock?

Such was the situation last night. 🙂

My Lady and I had semi-date night at home – it was one of the rare nights I was actually at home and we had nothing to do. So we laid down with each other on the couch, had a few drinks, and got a bit touchy-feely with each other. I pleased her with my oral skills for quite a while, but she still needed more. Describing her pussy, in her own words, “she [was] frisky!”

After ten full days of constant lock up, My Lady needed to feel her cock inside her. So she unlocked me and allowed me to enter her. I’m pretty sure she enjoyed it very much.  🙂   I held off as long as I could until she gave me permission to cum inside her… and I wasted no time in doing that!!! It was so wonderful and intense. I nearly collapsed on top of her afterwards. We both seemed spent, although shortly after we were right back at it again!

I’m locked back up this morning, in the Birdcage this time – we will be sending the JB back for a size adjustment. Although every day is a possible release day in this house apparently, my next official “Maybe Day” is Christmas. I’ll certainly be dreaming of a white Christmas for the next 25 days!