First Prostate Orgasm

We are heading into “Locktober” and my third month of chastity – which has been my limit in the past before I need a break. There are days the cage wears on me but for the most part I am still enjoying it.
Part of the arrangement this time around was to explore cuckolding because I was curious. Turns out…I really enjoy it.

I have always loved watching but being locked under strict instruction as well? Sign me up. I have not had the fortune of watching a scene in my new role but I have heard plenty. I recall vividly sitting on the couch downstairs listening to what I can only describe as a hard, mind blowing fuck session going on upstairs. The bed springs, the moans, the skin on skin slapping…even the ceiling fan right under was rocking uncontrollably (that turned out to be a maintenance issue – not anything to do with what was going on above it but still) it was HOT.

All the while my poor cock strained against constraints and its a wonder it didnt come popping off and through the wall the pressure was so tight. When they finished my cuckoldress made a point to tell me she considered letting me out to edge at the end but she was on cloud nine. I could tell by looking at her and her partner. They were in a good place. Me? Frustrated and locked.

This is where the idea of me being under strict rules while others are not was planted. Her partner…he could cum freely – in manners I never will be able to – while my own orgasm was up to my cuckoldress. I imagined him cumming with her while at best I got to cum in my hand and it turned me on. I imagined dating a woman and being forced to use condoms but her bull? Bareback. The ideas are endless. The vast divide in treatment – it added to the fire.

I will admit I am a bit disappointed in my own performance as a cuck. I came twice unintentionally. The first was using a toy that I was not overly familiar with and trying to get off in a tight 10 second window. I missed it but it was too late. I was balls deep in a fleshlight and so close that just the throbbing sitting in that position trying to come down pushed me over. So rather then whimper to a finish I pumped it a few more times and came. I was punished for it.

The second was while listening to another epic session. I had just had an incredible sense deprivation session and was allowed to go to bed unlocked. Then the moans started and I couldnt pass up the opportunity to edge could I? Not after that first day. So I did…but I didnt realize how overloaded my pleasure centre was. I literally came in under 15 seconds. It was sad and embarassing. I left that part out when I told her the next morning – she opted to not punish me.

There was one intentional orgasm as well that blew me away. Literally off the bed at least. I have been toying with prostate massaging/toys for probably 6-8 months? Maybe more. I never got to the summit. I tried and tried. Gradually with different methods and practice it started to feel better and better. But still. No result.

Until two days ago – I was told to put in one of my vibrating plugs and see if I could cum unassisted. It took a LOT of willpower to not reach between my legs but I did as I was told. So there I was on all fours at the edge of my matress slowly working through different patterns and building to what I hoped would be an orgasm.

It started to feel more and more intense – like my skin sensitivity was at an 11. My nipples hard as glass. I couldnt help but moan and let myself into it – that urge to pee building (but from what I read that was normal – worst case I wash my sheets right?) so I didnt fight it.

Then it hit. I came everywhere and for what felt like minutes. my body was racked with pleasure – my cock felt utterly empty and spent. I felt a bit shaky but decided to lean back to take a commemerative photo of the huge mess but realized my mistake quickly. My matress had shifted a bit so the boxspring was no longer supporting me fully and I slid off the bed to crash on the floor. My legs too wobbly to catch me.
I laid there on the floor for a good 15 minutes putting myself back together before hopping in the shower and locking back up. I really was overwhelmed with it all. Could I do it again? Would it be easier? Would it always feel that way? Would I be allowed to cum conventionally anymore? Would being pent up make it even easier/better?

I relayed my success to my cuckoldress who was pleased and has “plans” now that we know I can do it. Two days later it seems my libido is returning to nomal.

I woke up thinking about sex. Wondering if my cuckoldress got fucked and would she tell me? Then the cage reminded me not my place to ask – it would just torment me. Though…thats half the fun.

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