Real Life Story Regarding Male Chastity


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My Mistress has placed me in chastity lately and asked me to record me feelings on it. Here's the latest update from my chastity journal:
Last night was the first night of teasing in our new chastity regimen. It leads to strange sensations that remind me of unhappier times in my life. The teasing fills me with an intense but unrequited desire for release. Ordinary things about my lover seem to take on new meaning- the fall of her breasts, the shape of her hips, the line of her jaw- all seem somehow more erotic and (particularly) powerful. I often murmur to her that, “I want you.â€

Last night she replied with, “I’m right here.†Which, of course, doesn’t really help me because my desire is more specific.

Really what I’m saying is that “I desire to use you to achieve a form or release that will bring us closeness and a sense of fulfillment.†And what she’s telling me, often specifically, is that she’s available to hold me, but has no desire to bring a premature end to our experiment in chastity.

It reminds me of getting my heart broken. When I was younger and experiencing young love, it felt like a well of feelings had sprung up inside me. I was given to feelings of intense infatuation, longing for fulfillment, and the desire to be recognized and appreciated. In those days, it didn’t seem like the sun would rise for me without the approving consent of my beloved. But young love being what young love is, those days would end for one reason or another. And I would be left along feeling empty and abandoned.

I tried to separate myself from my feelings. To intellectualize them away, because all of my feelings would be of her- the object of my desire and meaning. Sometimes an ex would express some sympathy and seek to get together for coffee or something so that I would feel less alone. Those breaks would be a tremendous respite from the feelings of emptiness, but also a cruel trick upon the re-blossoming feelings of desire. We were “just friends†now, and friends didn’t desire each other. At least, they we’re supposed to.

I felt so pathetic in those days. Depressed. Wanting my life to be over. Numb. If I really stopped to think about it, I knew I’d start crying. If I put aside the desire for death, telling myself that things would eventually get better, but those sentiments seemed so hollow in those days. But, eventually, I grew up. Young love passed into the more pragmatic coupling of the late 20s and 30s. I no longer looked to my partners for fulfillment beyond the evening, and no longer burdened them with the messiness of my life. Life became simpler: predictable; scheduled; stable; livable. And that’s the life I chose to settle in and shape my identity around.

I don’t even like to really reflect on the horrible heart breaks of young love. I feel a period of deep shame come across me when I even admit to myself how pathetic everything was back them. Far from the predictable everyday, I only knew a chaotic mess of unfulfilled emotions and a life that felt like it was spiraling out of control. But chastity play seems to be bringing me back to those younger days- an outcome I somehow knew but would not have predicted.

Chastity and teasing fills me with a similar intense longing. I feel flooded by intense, demanding emotions that find no release except for quiet dissipation over time. It’s strange to take feelings of intense longing or, if I’m honest enough to admit it, rage and be told that “It’s OK,†and to just let them pass without acting on them. My mistress is there to hold me through these emotional storms, but that feels as empty as coffee with my ex-girlfriends used to feel. It’s nice and it helps with the feelings of being in it all along, but it only ignites other emotions (often amazingly negative) that then have to be allowed to pass.

I almost feel as though chastity play is an intense experience that can only be truly allowed to dissipate in the same somber aloneness that I used to fall into to try to put some order into an otherwise chaotic life. That when the session is over, the more rational and structured side of myself will once again step in, tell me it’s no big deal and to take a sleeping pill and go to sleep. Until we do it all over again the next day.

I was particularly worried last night when she told me what it was she had planned for this evening. She said that when I got home from poker, that she was going to restrain me, tease me, and then brutally fuck me with her strap-on until she was able to achieve orgasm. All in all, she expected to scene to be a couple of hours and to feature more of the darker and less loving sides of herself. This fills me with considerable consternation.

As I outlined in an earlier post, the ever popular “Getting Bound and Fucked by Your Lady,†I am used to my mistress pushing me to new limits in our strap-on play. But past episodes had featured an orgasm, followed by holding and aftercare. It was during those times when the world would all return to feeling normal and sane. I was able to marvel how intensely out of control I’d felt only just a moment ago as I was able to bond with her over the intensity of our shared experiences. But tonight’s session will be different; I will be brutally violated until she achieves orgasm. Then forced to slowly dissipate the intense feelings that such a unfair violation force upon me. I feel as though the intensity of my emotions will overcome me.

When we’ve experimented with it in the past, the unfairness or her bitchy and uncaring demeanor would match with the rising well of negative emotions I would be overcome by. When asked how I was feelings, I remember cursing her repeatedly. I hated her right then, just as I’d hated me ex-girlfriends back when they were the ones bringing me pain. In the particular session where we experienced these things, my mistress took this negative energy as an opportunity to ramp up the intensity of her violation. She slammed the full nine inches of the dildo deeper and more vigorously into me as she screamed an me what a emasculated slut I had been rendered to. In that particular episode, I eventually folded to feeling of unbelievable need. My cursing eventually gave way to soft whimpers as I begged her to please touch me. The massiveness of her hard, massive phallus seemed to comparatively powerful to my flacid penis, I couldn’t even understand how anyone could bring themselves to pay it any attention.

But then the scene changed, as it often tends to with Roulette. She suddenly took pity on the cowering useless man she was fucking, and allowed me to touch myself. I was so grateful in that moment as she allowed me to bring myself to orgasm. I knew that soon I would be back in the realm of the sane, and able to look what I had just experienced as a strange type of experiment which had now run its course.

But, that was then, and this is now. Putting our play along a timeline, it seems Mistress Roulette has been continually pushing me towards this end. First pushing me to larger dildos, then playing with the idea of unrequited and unloving violation. In our last such scene, she pulled me back from the brink. Tonight, I am not sure I’ll be so lucky, and that has me feeling very weary indeed.

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