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I never had a relationship with a woman, nor engaged in anything sexual with them. During the time I searched for these things I was regularly told I was too nice or lacked manly traits. It only flourished the emasculation inside me and made go deeper into sissification and degredation. I remembered those failed encounters last night, how I years ago thought I could date women, that I could be the special man to a woman and a father to her children. But it never happened, and will likely never happen. This feeling of degredation came to me stronger than ever the same night when another woman - an intelligent lady who knows her surroundings and desires, told me how girls my age rather sought manly figures for marriage and as fathers for their children. I had nothing to say…She knew I had nothing to say.
Later that night, the night before the 19th of locktober, I slipped into a pair of my silky white stockings, my most girlie pink suspenders, and a silky cherry bra. My clitty was still locked and already dripping precum against my white smooth legs. I took a one last look in the mirror, a look at myself. No traits of what a woman would want to spend her life on, or grow a family with. Then I looked away, letting the shame sink in down to every vein of my body as I prepared my boy-pussy for my remote controlled plug. I wasn’t allowed to stroke myself due to locktober, my clitty was locked tightly, but I was allowed to enjoy my toys and perchance have a relief in a most unmanly way. I knew the price, and I knew the risk. Even when it entered me without the vibrations, I could feel my sissy fluids coming forth eagerly.
Once I had a few saved cuckold captions ready on my phone to scroll, I started the vibrations - the lowest level. I could feel the pleasure of it like I haven’t had done before, or maybe it was the denial and frustrtion I suffered for 19 days of no masturbation. Or maybe, the sign of my mind, body and pleasures being further sissified and emasculated… It only took me less than a minute to release a big chunky load of my sissy fluids out into the open and squeezing down inside my cage and dripping out of the tip. Then another load comes out like crystals…Then another….Another! This was my first true sissygasm so far as it was so satisfying, so much more mentally stimulating! Making my body and mind acknowledge what I am in that very state! On each release inside my cage, when my clitty wasn’t even fully hard as it once used to be, I made my statement: I was truly a sissy now that could feel relief and pleasure through my boy-pussy. But it also meant that whatever little manhood I had left in me, was now gone.
Locktober was something much more to me this year. Not just a challenge, and not just a month of discipline and training. But also a last struggle of what maleness there was left in me, a statement of being a failed man, and the further acknowledgement of the pathetic sissy I was.
/@prissylegs
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