Assistant and housekeeper for My Mistress

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My Mistress, through Her vetting process, decided to own me as Her assistant and housekeeper. I trained for this kind of service ever since I can remember. Mistress told me that I had a lot to learn but that She chose me for my loyalty, honesty, and reliability. Also, She liked my close attention to detail. This gave me quite a boost and I said I would do anything to be Her servant.

A contract and a lot of tasks to fulfill from My Mistress!

She sent me the contract and waiver which I signed without pause. She knows me so well already, I thought, as I looked it over. Also, she included instructions to be carried out before my first day. She made a medical appointment which I needed to attend but gave no further details except the address. She enumerated all of the things I needed to look presentable on my first day.

My Mistress


These included all sorts of things like outfits, makeup, and jewelry. I was also ordered to have a spa day and have my hair styled. She instructed me to find a steel chastity cage that fits and that I like. That made me feel empowered. She then related that most of these things had already been picked for me and paid for and where I was to go. The main stipulation was that I had to document all of it. I had to try on and wear everything, and that meant everything! Even if I was used to wearing Feminine clothes and chastity cages in private Mistress insists this step be carried out to the letter.

I thought, this is a dream for me, why do I feel so afraid to do this? I was so nervous I had butterflies in my stomach.

It was hard to dwell on that though, and Mistress knew this because I was highly motivated and on a schedule.

The medical appointment

First on the list was the medical appointment. On my way to the appointment, Mistress sent me a text explaining that I should expect some surprises.

When I got there, the place appeared to be a normal medical office. I walked through the door and was immediately greeted by name and gently shepherded to an exam room by a friendly Woman in scrubs, who said Her name was Sherry. Sherry gave me forms to fill out and left.

The forms seemed standard and I signed them all. Sherry came back, promptly took the forms, and shuffled out the door again. A few minutes later Sherry brought in a gurney and had me disrobe and lie on it.

She brought me to a large operating room. She kindly explained I was to be sedated and given cosmetic and medical feminization. I was terrified they were going to cut off my testicles. Sherry reassured me that this procedure was safe, non-invasive, and did not involve an orchiectomy. It mostly involved laser hair removal, hormone administration, and prostate massage.

The prostate massage was to be done before and after the sedation. Sherry left after calming me and in came three Women. They were fully suited for surgery and looked imposing. Two of the Women spread my legs and applied restraints. They then put restraints on my arms as they sat me up slightly. the Third Woman put a thick helping of lubricant on her gloved hand and gently inserted it into my anus. She found the prostate immediately and proceeded to massage it.

A very good patient!

At this point, my mind was reeling. One of the Women came over to my side, caressed my head, and told me to relax and ride with it the best I could. I felt like a Queen with all this attention. I started to relax. Before long I felt warmth bubbling up under my strangely limp penis. A dribble of clear liquid started to ooze out. As the Doctor squeezed and rubbed it turned into a stream. I groaned and shook as I leaked and streamed alternatively, straining on the doctor’s hand. She said I wasn’t done yet as She continued to jiggle. I whimpered and gushed all over my quivering stomach. The Woman left the room after undoing the restraints and comforting me.

I was still shaking twenty minutes later, I felt empty, exhausted, and weak. Thankfully, the three Women came back in after some time and the sedative was administered. They were setting up for what looked like surgery when one of the women pricked my arm and I was out.

When I awoke, I felt refreshed. Sherry came in, asked how I was, and listened to me intently. I told Her about all the things I had noticed about my body.

My body hair was gone, except for a tiny line of hair above my penis. My lips were fuller, even my breasts seemed bigger, and my nipples were so tender, Sherry said that I was a very good patient and that my prostate massage would be in 15 minutes. I was very excited.

A general sense of rebirth and excitement

I grabbed my penis but nothing was happening. Then I felt a tingling underneath and an urge to rub my perineum instead. I tingled again as I neared my anus. my limp penis started to move a little. I felt empowered again. The three Women entered immediately and I peered up as they approached. All three smiled silently and I straightened up. They gave me knowing looks as they began the same routine as before.

After the session, I was worn out but with a general sense of rebirth and excitement. I did not know my body was capable of such things. Sherry came in again and explained that I was free to go, my clothes were pressed and hung in the bathroom. I went to the bathroom and found a beautiful blouse and skirt.

There were also some underthings, stockings, and high heels. I looked in the mirror. it appeared makeup had been applied to my face. I thought it looked so good, I put on the underthings. It was a cute corset top that perfectly framed my swollen breasts and a pair of satin panties that matched. These looked sexy under a loose white blouse and a short black skirt with a slit on the side. I put on the stockings and heels and felt a charge of adrenalin. Then I noticed some hoop earrings and a necklace that said “owned” on the counter and put them on.

I was ready! I smacked my ass and turned to see a small purse on the bed. It contained my car keys, some makeup, a panty liner, a new phone, and a small butt plug. There was a small note from Mistress as well. There was an address and nothing more.

To Be Continued.




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