When Ms. Robin
accepted me into her home it was with the understanding that I would be
submissive to her. I already possessed a strong chastity fetish which
after seeing the size of my cock (hereby referred to as my "sissy clit")
at full erection just barely reach 5 inches Ms. Robin didn't seem to
mind fulfilling my chastity fantasies. I was told to purchase a CB-2000
to get us started down the path of my total submission to Ms. Robin.
When the CB-2000
arrived Ms. Robin ordered that I start shaving my pubic area. She also
immediately started to cut back on the frequency of my being released
from chastity and allowed to make love to her. Ms. Robin stated that I
would soon be rationed to one orgasm per week for the first month of
training.
I just went 7 days
without an orgasm and yet Ms. Robin was teasing me to the brink 4 and 5
times or more each day. When I was finally allowed to release it felt
like the most intense orgasm that I had ever experienced. After having
the experience of this release Ms. Robin locked me right back up and
said that was it for a week.
I came home one day
this week to find that I no longer had any male underwear as it had all
been thrown out and replaced with panties. Ms. Robin informed me that
she was beginning my feminization and that soon I would not even want to
be without the lacy panties that I was now expected to wear 24/7/365. I
find it uncomfortable to wear the panties to bed but during the day I
find the silky feel of the fabric rubbing against my balls to be quite
erotic. Of course I can never let it go too far as an erection reminds
me that my caged cock is under the control of Ms. Robin.
After 9 days I was
allowed to have an orgasm. It was even more intense than the one before
which I didn’t think would be possible. After it was over Ms. Robin
straddled my face and had me clean up after myself while she replaced
the CB-2000 on my totally limp equipment. Ms. Robin took this
opportunity to advise me that chastity would soon be a permanent part of
my life because I did not possess anything like the equipment of a real
man. She told me that my little (just barely 5 inches when fully erect)
cock would hereafter be referred to as my “sissy clit.” Also, I was
informed that Ms. Robin would occasionally enjoy the services of a real
man. I advised Ms. Robin that I was familiar with “cuckolding” and would
not object. I, of course, would be jealous and scared but I would try my
best to honor her wishes.
The
entire week went by and no orgasm was allowed for me by Ms. Robin. She
continues to tease me several times a day and is always amused at my
sissy clit when it tries to get erect inside of its cage. I have noticed
though that my erections are getting less intense as I adjust to the
CB-2000. My sissy clit seems to know that it is in a cage and that a
full erection is quite painful. I find that I am quite used to the
panties that I wear always–so much so that I rarely even notice that I
have them on, let alone get aroused by wearing them, like I used to just
a few short weeks ago.
I am
now expected to keep my pubic area free from hair. Ms. Robin informed me
that since I cannot use my cock in a manly way that I will not be
allowed to have any manly hair around my sissy clit. I have noticed
initially that this was enhancing the erotic feeling that I was getting
from the panties that I am made to wear always. But that feeling was
gone by the third day after shaving my pubic region.
On my
12th day in chastity, Ms. Robin finally allowed me to have an
orgasm. But this time she had nothing to do with it. Rather, she had me
stand at the foot of the bed and gave me the key to unlock my CB-2000. She then instructed me to remove the cage portion of the device but to
leave on the A-ring as the cage would not be off long. I was then
instructed to put a condom on my sissy clit so I wouldn’t make a “mess”
as she put it. Fortunately I was starting to get erect so there was
enough there to be able to slide the condom on. Ms. Robin then
instructed me to begin jerking off. She then set a timer for 5 minutes
and advised me that if I had not yet cum by the time the timer went off
that I would have to wait another 11 days before I would be allowed to
try again. She also instructed me that I was only allowed to use my
thumb, forefinger, and middle finger to jerk off with. This was so she
could still see a little bit of my sissy clit as it is so tiny that if I
use my whole hand it often disappears from view. After the first minute
Ms. Robin asked if I was at full erection. I said that I was and she
handed me a measuring tape. I measured my length at full erection and
advised her that it was 4.75 inches in length. This announcement brought
forth much laughter from Ms. Robin. I came in minute 4. Ms. Robin
ordered me to remove the condom carefully and set it aside for my
consumption later. Then she ordered me to re-attach the cage of the
CB-2000 to the A-ring. I ended up being free of the cage for less than 7
minutes total. Ms. Robin then had me recycle the contents of the condom
I was then required to service her orally to half a dozen orgasms before
it was time for bed.
There
was no orgasm granted me this week. Ms. Robin also added something new
to the list of things that I must do in order to please her with my
service. Ms. Robin was giving me a discipline spanking with her wooden
hair brush when she advised me that it was very distasteful having all
this hair on my ass. So she advised me that the new rule that would be
in place was no more hair from the waist down. Leg shaving would have to
be learned. Ms. Robin advised me that by obeying her without question I
would have the opportunity to cum again this week. She explained to me
that I looked rather silly with hairy legs when I had my pubic area
shaved. But that didn’t matter to me–I just wanted to cum again. So I
shaved my legs and ass when doing my pubic hair that could be reached
around the CB-2000 which was not removed and true to her word I got to
cum just 7 days removed from my last orgasm. It was done exactly the
same way as the last one except that this time I only lasted about 2
minutes.
In the members pages, you
will see the pictures of Rachael's new chastity belt, makeup
applications, and milkings. Rachael will continue the training
diary. Rachael will share experiences, videos, and pictures of
punishment spankings, Pleasurable Electrical Stimulation (PES)
milking, heel training, and other wonderful things a sissy must learn in
order to serve his Mistress properly.