Disclaimer: The following piece of fictional writing contains adult themes and explicit content, including sexual acts and language. It is intended for mature readers only and may not be suitable for all audiences. Reader discretion is advised.
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Chapter 4: Training Continues
"I think your great performance so far should be rewarded," said Mistress as she got off the bed, leaving me still tied eagle-spread with my face and hair covered in her pussy juices and piss. Mistress came back with a glove and a bottle of lube.
"To reward you for being an expert pussy licker, I'm going to let you cum," she continued gleefully as she saw the hopeful expression on my face. "Well, I'm certainly not going to jerk you off, if that's what you're thinking. Your clitty doesn't get unlocked unless it's for a good reason, like hygiene. Otherwise, it stays in its cage until it has been fully trained to remain soft. Now, back to sissy masturbation. The only way for a sissy to masturbate is with her sissy pussy, and I'm going to show you how you can cum as a sissy."
I realised what was about to happen but was in no position to do anything about it. Mistress pulled on her gloves and squirted a generous amount of lube between my crack. The touch of her finger running over my sore rosebud made me resume begging Mistress. "Aaahh, please Mistress, please don't do this. Please, I'll give you anything if you just let me go, I beg you, please!" I thinned, starting to sob, but Mistress wasn't planning on showing any compassion.
I felt a jolt of electricity shoot through my body and I spasmed in pain, letting out a yelp. At the same time, Mistress shoved her middle finger straight into my butt, all the way up to the knuckle. I let out a second yelp in response, more in surprise than actual pain as Mistress' finger was slender, well-lubricated, and most importantly, significantly smaller than then dildos she had already forced up my ass.
"Relax sissy," said Mistress in a satisfied tone and a grin. "Just enjoy the ride and you'll be cumming in no time. That much, I know for certain. Now don't spoil your reward by making me shock you again."
Having being shocked, I just stayed in position, too afraid to move. Mistress slowly started to slide her finger in and out my sissy pussy, establishing a rhythm. Then Mistress inserted a second finger before curling her finger ever slightly upwards. It was just enough for her fingertips to brush against my prostate and with each successive stroke, she increased the pressure.
The sensation was very odd, and it simultaneously felt like I needed to pee and butterflies in my stomach. As Mistress kept stroking, to my horror and to Mistress' delight, I let out an involuntary moan. I hated what was happening but the feeling was growing increasingly intense and sort of felt nice. Despite my best efforts to suppress my moans, it wasn't long before Mistress had me whimpering and twitching between suppressed moans.
Suddenly, the intensity of the sensations peaked and, even though my clitty was locked in a cage, I felt myself spasm and the sensations seemed to flow out of my clitty. The sensations felt like a raging storm inside me and wave after wave of orgasm rolled throughout my body, originating from inside my sissy pussy, and it felt like it would go on forever as Mistress continued to finger me.
The feeling of release was nothing like the explosive orgasms that I was used to and despite the lack of an 'explosion', this orgasm was the most intense one I've ever had. So much so that I passed out momentarily and regain consciousness to Mistress slapping my face and squeezing my mouth open.
With her other hand, Mistress had caught my sissy ejaculate and was pouring my own load of cum into my mouth, feeding it back to me. I was too dazed to resist and involuntarily swallowed. Mistress made me lick her glove clean of all my juices.
"Well, clearly you enjoyed that sissy," Mistress casually stated as she put away the bottle of lube and stripped off her gloves as I continued to come down from my orgasmic high. "Now you know you can still masturbate and have a sissygasm even in your cage. But you will always have to swallow your girly juices if you do and this will be the way you will ever cum from now onwards."
Mistress inserted a buttplug into my sissy pussy. It felt rather large compared to her fingers. "This will be a new addition to your training," Mistress continued as she released me from my bonds. "When your sissy pussy is not being filled by cock or your dildos, you will be wearing a butt plug. This will ensure that your hole is always ready for use and help you get accustomed to the feeling of being filled all the time. Get your ass over to your feeding dildos and start sucking."
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A second round with the feeding dildos left me throughly humiliated at having to swallow the horrible tasting fluids for the second time in a span of several hours. The residue of Mistress' pee and pussy juices had dried off on my face and hair. I felt rather gross and disgusted and wished Mistress would allow me to go wash up, but that didn't seem to be coming anytime soon.