Chastity and orgasm denial discussion

member_29f66e96ba · 2026-09-02T06:48:12.000Z · 0 replies

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2026-09-02T06:48:12.000Z #1

Greetings everyone.

I hope I have posted this in the right section; if not, please forgive me. Many of us who regularly live under lock and key eventually experience those occasional sobering “mental thunderclaps” as our journeys evolve. Last night, while browsing several chastity websites for a hot picture or short erotic video to send to my Wife/Mistress/Keyholder, I had an epiphany. I usually do this a few times a week, selecting still images and writing brief fantasy dialogues to accompany them. Sometimes I choose videos that are mostly self-explanatory but include a short thought.

ANYWAY…I found a video just under 20 minutes long featuring a muscular, athletic Caucasian guy with no hair from head to toe (roughly in his thirties or forties) and one of the most convincing she-males I have ever seen. I was expecting some form of chastity involvement, but there wasn’t any. The video followed this man performing what must be the tenderest, sexiest, hottest anal intercourse on a she-male I’ve witnessed in a clip. There was no verbal degradation and no wincing from pain or crying…just sheer rapture for both participants.

Now HERE is the part that hit me like a cold, wet fish across the face. As I watched mesmerized, this guy’s erect penis slowly sawed back and forth inside his “girl“‘s willing ass… The smaller veins on his shaft and the large vein along the bottom looked incredibly prominent and defined. His skin was shiny and taut, clearly showing he wasn’t faking his enjoyment. He did it for nearly 20 minutes until he finally climaxed.

I remembered fucking a woman like that for 20 minutes with full control. I recalled my erection feeling as though it might split the skin of my penis. I remembered the sensation of my PC muscles tightening behind my scrotum and my anal sphincter clenching so tightly nothing could slip inside me. I remembered the amazing sensations of a warm, wet vagina or a smooth, clenching anal sphincter enveloping my hard, throbbing member for 20 minutes or more, before finally letting go voluntarily to fill my lover with semen.

So there I was watching this video three times, utterly astounded, with my penis locked away and unable to swell into an erection within its confines. I cannot recall the last time I felt “that guy”. My Wife/Mistress/Keyholder has been interested in seeing how quickly she can make me climax for about two years now, ever since I introduced a chastity device into our dynamic. Before that, my usage was intermittent and quite light.

Things shifted after our most recent “restart” when I promised to stop “topping from the bottom.” Hence, just shy of 2 orgasms in nearly 2 years, with expectations for me to wear the device unless I have a doctor’s appointment or engage in athletic activity. Enough about the arrangement though; I keep seeing that guy’s hard cock sawing away in my mind, and I am pining for those feelings and sensations.

I mentioned this to my Wife/Mistress/Keyholder, and she cheerfully told me I should have considered it before starting down our current path. She says I need to let the past go and be happy with where we are now because she has no desire at this time for anything to revert to our old footing.

I am more like the she-male in the video now, receiving pleasure anally from a plug instead of a cock (like “her”), having my nipples sucked without orgasms. I felt sorry for “her” as she stroked her tiny, hormone-shriveled penis into a pseudo-erection but fell short of being able to achieve release.

So what is it? Regret? Jealousy? Has anybody else had a similar moment? I would love to hear thoughts from both sides. allaboutHer

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