Chrissie The Saga of a Lovestruck Sissy Maid
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Becoming A Career Sissy Maid free porn video
I have been submissive for as long as I can remember. Growing up I
adored my mother and would watch everything she did around the house.
Eventually I would help her with more and of the cleaning, cooking and
laundry. She playfully called me her maid when I was helping her and I
began to refer to her as Ma'am.
When I was 13, we decided that I should go to a friend's Halloween party
as a French Maid. For some reason this really excited me! My first
masturbation fantasy was imagining myself as a real maid. My mother
ordered the maid costume and related accessories well before the party.
In the meantime she suggested that we role play so I would be more
realistic in my pretend role.
The role play started with learning appropriate mannerisms, then
progressed to training to make the role second nature. My mother
insisted, and I agreed, to stay in the role full time in the month before
the party. I learned to curtesy, to cheerfully follow her orders, speak
only when spoken to, and to be constantly ready to serve her. We both
had a lot of fun doing this and I would occasionally break character to
laugh and hug her. Things progressed further after the costume arrived.
I had to become comfortable in the uniform with the apron, cap, corset,
stockings and high heel shoes. She also restyled my hair and taught me
to apply makeup. Anytime I was in my uniform, nearly full time, my
mother called me Maid and used female terms such as girl or her.
Things got a bit more serious when my Mother decided that I needed a
trail run serving her and several friends at a formal tea. It was a very
good idea because I was nervous and embarrassed at first, but got
comfortable with my role by the end of the tea.
The Halloween party went very well, my friends were shocked, then amazed
at the convincing Maid I had become for the party and how I managed to
stay in character for the whole time. I properly referred to everyone as
Sir or Miss and did a lot of curtsying. My closer friends took turns
being my Master or Mistress by ordering me to refresh drinks or run other
errands. It was interesting to see that the girls were a lot more
comfortable bossing a Maid around than the guys were.
Through high school I was my mother's maid every weekend and whenever she
had a party. Several of her friends "borrowed" me to serve as the Maid
at their parties. Many of my friends made extra spending money mowing
lawns or babysitting. I made some modest money serving at these parties.
During summer vacations, my Mother scheduled me to clean her friends'
houses. Some of these women had been to my Mother's parties and insisted
that I clean while properly uniformed. Having a uniformed house cleaner
became quite the status symbol in our town. These were very happy times
for me.
Through college and early adulthood, I tried to suppress my submissive
urges. I tended to date strong women, but never dared to dress as the
maid. Like a lot of submissives and cross dressers, I worked hard to be
normal. I also had relapses and began to occasionally see a professional
dominatrix.
I had been to see this woman several times and we became comfortable
enough with each other, that we would often have a good laugh and cuddle
after a particularly intense session. After one session, she told me
that she was seeing someone new after me. She offered to extend my
session by leaving me in an unlocked cage while she had the introductory
hour with her new client. She explained that where she got her training
they always had a second person monitoring a session for security. She
would feel more secure if I stayed.
I was naked, with a ball gage, cock cage, wrist and ankle shackles,
seemingly looked in a steel cell during the second session. Sure enough,
things started out fine with the new client, but at some point he got
aggressive with my friend, refused to obey her, and then tried to rape
her. I came out of my cell, caught him by surprise, and got a pair of
hand cuffs on him before anyone got hurt. Yes even submissive cross
dressers have served with the military police.
Mistress was very shaken. After we played back the security tape for the
would be rapist and convinced him that it would be in his self interest
if we never saw him again, we let him go free.
She cancelled all of her appointments and didn't see any clients for
weeks. We started to meet every couple of days for coffee. I think that
she avoided friends and family for fear of having to tell anyone else
about her experience. She was burning through her savings and to cut
costs let her cleaning woman go. I realized how serious things were
because finding a good cleaner for a house with a dungeon can be
difficult.
Mistress gradually began to reconnect with her oldest clients.
Apparently both she and her clients recognized that things had changed
with her. One day over coffee, she asked me if I would come over during
a couple of sessions to see if my being there would help restore her
sense of security and confidence. It worked wonders, but a couple of
clients expressed discomfort with another guy hanging around. One even
asked if I was her creepy voyeuristic husband.
I suggested that if I was busy doing something, everyone would be more
comfortable. I shared with mistress a little of my childhood and
described my cleaning skills. I made the point that her place obviously
needed a serious cleaning since she gave up her cleaning woman. This is
when I also shared that I had lost my job and was having trouble finding
another.
I could see the gears turning. She spelled out how she saw all the
pieces fit. She needed to get back to work and rebuild her business.
She needed security she could trust. Her dungeon needs regular cleaning
and maintenance. I needed a job and I seriously missed our Mistress and
slave sessions. Her business instincts then kicked in. She said that
she would hire me, but she didn't want the hassles of a payroll. I would
work for the domestic agency she used for her previous cleaners. The
agency would contract with Mistress to provide my services. A close
friend of hers owns the agency.
The prospect of working for a domestic agency stirred deep memories and
strong feelings from my youth when I served my mother and her friends as
a maid. At this point I felt very close to Mistress and obligated to
disclose this additional part of my makeup. I told her about my first
Halloween dressed as a maid, my weekend service to my mother, serving at
the parties, and being rented out as a house cleaner. Mistress' smile
got bigger and bigger as I told her about my experience working as a
cross dressed maid and how it excited me.
Mistress exclaimed PERFECT. While she needed security and cleaning, her
business would suffer if her clients were at all uncomfortable. No one
pays any attention to the help, especially a maid. I would work in her
house and place of business as her Maid. Knowing my submissive needs and
now my experience as a domestic servant, she said that we could make this
interesting for me too.
I would change careers to domestic servant, or more specifically a maid.
I would sign a long term contract with her friend's agency, renewable at
the agency's option. They would have the right to assign me to work for
any of their clients including of course Mistress. The agency would
contract with Mistress and potentially others defining my service,
behavior, training and corrective measures, uniforms, etc. Where
appropriate, the contracts will dictate how the maid will address the
Mistress and her associates. Mistress then paused while I took all this
in. When she continued, she promised to make my experience one never-
ending session complete with enforced chastity, routine bondage and
torture whether I deserved it or not.
After an awkward silence, I asked if I could kiss her one last time as
her friend and a free man before entering her service and moving into the
Maid's quarters.
Trish
- 05.09.2020
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