One of the most important rules that My Lady and I follow is the concept of “Maybe Day.” We usually set a target date for my next orgasm, but ML is under no obligation to allow my next orgasm to occur on that day. She can make me wait longer if she desires, or have me cum earlier if she wishes. Basically, every day is a Maybe Day. What’s important is that ML is in charge and she gets what she wants.

This weekend, My Lady wanted to give me an orgasm. After 105 days of being teased, made to wait while my wife enjoyed orgasm after orgasm, it was finally my turn on Saturday night.

I had the feeling that this moment was sneaking closer and closer. My Lady had been making comments for about two weeks about how good it would feel for me to cum and how badly she wanted to feel it. With three months of denial in the rearview mirror, I was in no condition to argue with her. Then, last week she mentioned how she might let me cum over the weekend. I was excited (of course!!!), but I did my best to not get my hopes up too much. After all, ML truly an expert in mindfuckery, and this could have been a ploy to make me that much more crazy horny.

Contrary to what you would have expected, there was not a big deal made out of it. There wasn’t a hot scene prepared with bondage and teasing and all that, we were both craving the simple closeness of being with each other. ML instructed me to remove my cage and we began having sex. Just like the many times before, I was close to orgasm before even a minute passed. Slowing my pace, I held on for a little while, thrusting my hard cock into tight wetness. I looked into her eyes and I told her that I needed to stop.

“Wait,” she told me, and patted the bed next to her. “Lay behind me, I wanna spoon with you for a little.”

I laid beside her on the bed and cuddled up behind her as I felt her hand guiding my cock into her pussy again. It’s such a different feeling, entering her from behind. It gets to me so much quicker. I only had enough time to slide my hand up from her hip to cup her tit before I felt my orgasm rushing towards me.

“Please can I cum?” I whispered in her ear. She paused for just a moment, then let out a soft moan.

“Yes,” she answered, “do it.”

I didn’t expect it to happen so fast; I thought maybe I would have another few thrusts before I came. But almost exactly when she said yes, I felt my entire body shudder as I had my first orgasm in over one hundred days.

My body shook and I squeezed her titty hard as my hand clenched involuntarily, but my hips kept thrusting my cock into her pussy, filling her with long stored load of cum. After a few moments, I could feel my cock get really sensitive, especially the head as it parted her pussy lips and drove deeper inside her. The sensitivity was almost too much to handle, but I couldn’t stop thrusting, nor did I want to. It felt just too damn good to stop.

Instead of stopping, I started to laugh. It felt like the most natural thing to do; everything just felt so good at that moment, that was the only thing I could do. Even when I was finished with my orgasm, I was laughing softly as noticed my body was as tight against ML’s body as it could be. Afterwards, I found out that she too had an orgasm, triggered mostly from the intensity of the situation and feeling my reaction to what was happening. I was happy to hear that, only because I couldn’t really control much of what I was doing once I started cumming.

We made love once again in the early morning, before the kids woke up, and ML allowed me to have an orgasm once again. This time I was a little more under control, and was able to enjoy the feeling of her pussy squeezing me as she came herself. We haven’t had sex since, because of events with the children or due to me being caged – the steel tends to be quite the deterrent when it comes to PIV sex, but sometimes the children can be even more effective!

So now the big question that is probably on your mind – and is CERTAINLY on my mind – is how long am I going to be waiting this time around? Well, it’s probably not going to be anywhere near as long as my last few stints: My Lady has already mentioned that we may take a break from the denial portion of our play for a bit.

Now don’t get worried like I did when I first heard this! I thought she meant she wanted a break from everything we have been doing. Not so, she explained. She just wants a break from doing things long term. She may tease me from day to day, and make me wait a few days here or there, but she misses being able to have me whenever she wants and not be holding off for a certain amount of time. And she DEFINITELY wants to keep up the chastity! I completely understand what she is feeling, and I agree. I miss not having to stop less than a minute into sex day after day. I have a feeling I’m still going to be kept extremely horny by ML’s sexiness and nonstop teasing. I’ll just be getting my pleasure a little earlier than I’ve grown accustomed to. And when we are ready for another long term go at it, we will know it. We are having waaaaaaaaay too much fun to stop what we’re doing now!

So don’t get TOO jealous when you read about me having orgasm after orgasm. After 105 days of denial, I’ve think I’ve earned a little bragging rights!!!  😉