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.
While I was feeding from the dildos, Mistress had left and brought back in a tablet, a fluffy pink notebook and matching pink pen, and a chain with clamps at either end. Putting down all the stuff on the bed, Mistress pulled aside my bra and clipped the chain onto both my nipples, with the chain hanging between them. Tears started to form in my eyes as the nipple clamps hurt even more as Mistress tugged the chain with her fingers.
"Good progress today, Bambi. You're one of the best sluts I've trained in a while. Now, you may have realised that I'm a professional and have been paid a lot of money to transform you into a top notch, pleasure inducing, submissive shemale bimbo. I understand you are here against your will, so to speak, since you legally belong to Mistress Charlotte and she has put you here to be trained. You've only experienced a little bit of punishment so far, but that's all that you're going to face if you continue to be as good as you are. If you don't, well, let's just say that you don't want to find out. But if you are good and complete your training, then you will be released into the recognisance of Mistress Charlotte once your training and transformation is completed. Do you understand me?"
My head spun as Mistress spoke, but she quickly brought me to my senses with a shock and I nodded in an affirmative.
"Good. We will work on your manners and demeanour as we go along, but for now, I want you to watch the instructional videos of how to give an amazing blowjob and 3 more pornographic films. During all of these videos, you are to take detailed notes. I will test you on them when I return and I want you to be able to tell me what you should do to perform an amazing blowjob. I will also ask you questions on the films, focusing on how the female moves as she is being fucked, what she does or says to heighten her partners' pleasure and how she seduces him prior to her getting fucked. Now turn on your tablet and start. I'll see you in a bit."
Turning on the tablet, I sat on the bed, opened the fluffy pink notebook and was apparently ready to start learning how to suck cock and get fucked like a pro. I hated every second of it. I clicked play and on the screen of the tablet, the title "Blowjob 101: Pleasing your man" was flashing on the screen. As the video began, an attractive blonde woman appeared on screen to give an introduction about how this instructional video would be all a girl would ever need to learn how to please cock at any time. Images of women in various stages of sucking a man off flashed on screen.
The blonde woman continued by saying that she and some of her friends would give detailed descriptions and demonstrations of their various techniques, and there would be opportunities for the viewer to participate with their own dildos. The video paused right after the blonde lady waved her dildo on screen and said that she would give the viewer a moment to get her dildo. She continuously used the female pronoun as this video was obviously intended for a female to watch, not a male being transformed into one.
Hesitantly, I looked around the room, hoping that the video would just continue but it was clear I was being observed and the video would not continue if I did not get a dildo. My first thought was to rip out my feeding dildos but I suspected that I would be subjected to a lot of pain if I did so. So I reached over and opened the drawers of my nightstand and, surprise, surprise, a pink dildo was there, one that looked identical to the one the woman on the screen was holding. Once I retrieved the dildo, the video immediately continued on.
Over the next two hours, I learnt more about giving a blowjob than anything else I had learnt in my entire life. The video would routinely pause, either for the participation segments or if something important was said that I needed to write down in my notebook. By the time the instructional video was over, my pink dildo was slick with my saliva, and I had written nearly 5 pages of notes, all on how to suck cock like a pro.
Glancing through my notes, I flushed in shame and humiliation at what I had written down. I had notes on how some men loved having a tongue swirled on the head of their cock before taking it into the mouth, while others got off on hearing sucking and slurping noises. Some men enjoyed having the woman stimulate them only with their mouth while they took complete control, and others enjoyed laying back and letting the cocksucker do all the work.