ML and I have always been curious about whether or not I was able to have an orgasm while wearing my chastity cage. We know it’s possible in the general sense – we’ve heard about it from many sources, and there are plenty of femdom videos where it happens. We just didn’t know if I was actually physically able to do it. We tried using the hitachi wand as well as other ways of stimulation, all with no success. Until last week, that is.

I’m now able to confirm that I can, in fact, have an orgasm in my cage. And, honestly, it might be even more frustrating than a ruined orgasm.

But I’m getting ahead of myself. Let me start again…

My “leaving for work” ritual has changed quite a bit after our moves from NY -> WV -> IN. I used to kneel for ML and give her some body worship before I left, and ML would almost always flash me her titties as I drove away (seriously, don’t I have the best fucking wife in the world?). Recently, our kids have been getting up earlier than they have in the past, and they are usually awake by the time I am leaving. This makes it tough to do our routine on a normal basis, but we make time for it when we can.

Last Wednesday morning, ML and I snuck off to the bedroom to get a little privacy. ML laid back on the bed and spread her legs, offering me her delicious horny pussy. I knelt at the side of the bed and began licking her. As always, she tasted AMAZING. As I licked her clit and kissed her pussy lips, she began to moan quietly (trying not to alert the kids in the next room). It was so sexy and it was turning me on like crazy!

ML had kept me locked in the cage all the way from the previous weekend; I was really craving the feeling of being inside her, and her moans of pleasure were only making that craving worse. I may have gently suggested to ML that she unlock me, but my full on “rooty” would have made getting out of the Jailbird almost impossible. But I didn’t care – for some reason, I felt like I NEEDED to be inside her at that moment. So I climbed up on the bed, kneeling in between ML’s legs, and began gently sliding my caged cock into her slippery wet pussy.

My Lady has been very impressive with her ability to handle my chastity cage inside her. When we first tried it, I was barely able to move without causing her discomfort. Now, I still have to be careful, but I am able to thrust into her a little bit (as long as I get the curve of the cage at the correct angle).

The feeling of fucking ML with the cage on is really difficult to describe. On one hand, any time I get to feel ML’s pussy wrapped around my cock is absolutely wonderful. But when I’m wearing the cage, I can only feel her pussy with the parts of my cock that bulge out past the bars. The result is a strange combination of great pleasure and immense frustration.

As I continued to thrust into ML, these conflicting feelings must have been showing on my face, because I saw a flash of excitement in her eyes. She was getting off on my frustration. I could feel her excitement flowing from her as I watched her drink in my suffering. Her excitement increased my arousal so much and so quickly, all of a sudden I realized something.

I looked into ML’s eyes and said, “I think I could cum.”

“Really?” she asked.

“I think so.”

“Do it,” she answered. “Cum for me.”

I had been waiting SEVEN MONTHS to hear My lady say those words.

It didn’t take me long to fulfill her request. I had to control my thrusts in order not to hurt ML with the steel chastity cage, but I was able to push myself to orgasm.

It was, in a word… terrible.

First off, getting myself to orgasm was nowhere near the way I wanted to do it. After seven months of denial, I really just wanted to pound ML’s pussy and cum deep inside her. I couldn’t do that here; I had to thrust very slowly, which ended up making the climb to orgasm a horrible tease of an ordeal. It was like instead of diving into a pool, I was slowly dragged across the cement and unceremoniously dumped in.

Then came the orgasm itself. It wasn’t quite a ruined orgasm because my cock was being stimulated throughout the whole thing, but it was very much like one in the fact that it was absolutely not pleasurable. It was more like a “blocked” orgasm: my cock surged in its cage, eager to release seven months worth of pent up orgasmic pressure. However, each time my cock pulsed, it met with the unyielding steel of the cage. Still desperate for a deep, intense, cum-pumping orgasm, my cock tried even harder, but with no success. All that happened was an even bigger buildup of pressure, only now I could feel it all throughout my cock. At least with a ruined orgasm, there was some sense of release; I wasn’t even gifted that here.

I could tell My Lady could feel my bulging cock twitching inside her because her eyes had an intense look in them. The look on my face was probably equal parts surprise, confusion, desperation, and frustration, and she was loving every single second of it. As my cock continued its strangled orgasm, I couldn’t help but whimper as I suffered through the torture. In the end, I wasn’t able to fill ML’s pussy with my cum; it ended up dribbling out later once my cock had given up and gotten soft.

So yes, it was absolutely horrible, in such a good way. I was teased and taunted by an “orgasm” that ended up being more frustrating than I could have imagined. Now knowing how this effected me, I wouldn’t be surprised if ML were to try this again, only next time using her wand to give herself a ruined orgasm while I suffer through mine. I’m not sure if I could think of anything more soul crushing than that.