The next day, the bitch called Me again, after having dropped another $1000.00
tribute into My account, and surprised Me with how quickly he had already
purchased some of the items on the list. I had him dress up in the classic
French maid’s outfit, complete with white apron and stockings and some black
Mary Jane high heels and he even had this cute blonde wig already on his head. I
could tell he was drunk, but not as badly this time, because he wanted Me to
make him drink for like the next five hours while we talked. I got him into full
makeup, including foundation, blush, mascara, eyeshadow, lipstick, and
everything, and then I humiliated the shit out of him by making him try to
practice talking like a woman and making him repeat over and over again, “i’m a
little sissy with a tiny little clit that gets all stiffy”! LOL!

I wanted him to go to bed all dressed and made up like that and then he is going
to call Me tomorrow after he wakes up from his drunken night of pathetic
worship. At that time, I am going to make sure he gets all of his makeup removed
before he goes into work. I don’t want him to lose his job because the bitch has
to have some sort of income to keep paying Me the big bucks that I am worth.
What he doesn’t yet know is that I am going to make him wear the white
stockings, some frilly pink panties, and a training bra to work underneath his
suit and then I am going to make him call Me everytime he takes a smoke break
and during his lunch break too. I have no doubt that this piggie is going to be
one of My favorite money machines. I can’t wait for his chastity belts to get
shipped so that I can totally control both his cock and his wallet even more
than I already do. I am so cruel to be so kind! LOL!

So the man girl kept me on the phone so long I needed to break this up because he kept me up too late LOL

While we were on the phone, I had him order a few different chastity devices
with keys and then, later, when he had sobered up enough, I made him strip and
put on every stitch of feminine clothing that he already had in his possession
so that he could go to sleep in it and then take photos when he woke up in the
morning completely sober. I also had him apply some slut red lipstick and paint
his toenails the same color while we were on the line and then I started having
him hit My tribute buttons, once for each item discussed or purchased, both from
the email and while we were on the phone. I was totally raking it in from this
stupid sissy loser.
I wonder if he knows he is heading for a cock sucking lesson

My new dickless money pig called Me again tonight and, again, he was so trashed,
but at least more coherent this time. I made sure he paid a $500.00 pay-to-view
email that entailed how he was to begin his transition into My fully sissified
and chastised cash slave and he was very excited, even in his stupor, to call
and talk to Me for hours about being controlled and transformed. I instructed
him, in great detail, to start the process by shaving all of his body hair,
buying makeup, lingerie, and cute fetish wear, but first, I wanted him to go out
and buy a closet full of pink sweats and other cute things for him to work out
in, especially when he was out jogging or hitting the gym. I found this place
online for him to buy “Girl Power” T-shirts and funny stuff like that. OMG, he
was so excited to be humiliated with these simple little things. I just know it
is going to be a blast taking him through the whole process.

It turns out he had gotten drunk, stared at My NiteFlirt pages and photos, tried
to resist calling Me by going for a nice long jog, and then, upon returning
home, took a few more shots of gin and called Me anyway. This bitch is addicted
to alcohol, exercise, and now Me, Hah! I had no problem sinking My claws into
his willing flesh. That is just the way it is. Now he is on the path that I am
ruthlessly creating for him. I have demanded weekly tributes and so far he has
sent me a cool grand. Soon, I will extend his sissy fetish into a full-blown
forced fem lifestyle and become the keyholder for his chastity belt. With each
level I take him to, he will sink deeper and deeper and there will be no turning
back. I know he wants to be My victim and I am perfectly suited to prey upon his
powerless mind and flesh. Princess Caitlyn takes prisoners. Line up suckers!

Another day, another new piggie, another thousand dollars. What a wretched little worm boy My new human ATM is. Get this: the piglet calls Me, out of breath, clearly drunk, and incoherently stuttering with fear and self-loathing. I told him to calm the fuck down and listen to Me, carefully, and that I expected him to do his damndest to concentrate on answering My questions directly and honestly concerning his fetishes and deepest submissive tendencies. I proceed to quietly interrogate the bitch, alternately making him feel comfortable via My sensual voice and sharp intellect and sinking him deeper into his subconscious need to serve a truly superior Princess. I found out that he was a lonely divorcee who had not had sex for fifteen years, had developed a fondness for wearing silk negliges and stockings, was obsessed with being placed in chastity, and had a fat wallet just aching to be plundered.