Pro Domme Assignment Pt. 01

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My report to my Key Holder.
1.3k words
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Part 1 of the 2 part series

Updated 06/09/2023
Created 05/03/2019
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I once served a daddy dom for quite a while and he set up a meeting with a Pro Domme for me. The following is part 1 of the email report that I sent to him.

You had scheduled me to meet Head Mistress S at 5pm so at 3:45 I showered thoroughly, re-shaving my entire diaper area as you directed. I tried hard to scrub around the base ring of my chastity and spray water into the tube until it was very clean and shiny. As you know, I had been wearing my plug all day to prepare so I removed that and thoroughly washed it. I dressed in casual clothes and a Blue DC Idyl diaper with 1 booster insert, lots of powder in my diaper and baby lotion rubbed all over my body.

I nervously drove the 20 minutes to the location and waddled into the nondescript building having flooded my diaper while sitting at a red light. As I walked in I was immediately confronted by the Head Mistress S sitting at a desk in the lobby, she was beautiful. It felt like many of the luxury city clubs I have been to for dinner in the past. I was invited to sit and Mistress R brought me a bottle of water while the Head Mistress and I went over paper work and tribute.

Once the formalities were complete I was then lead to another room by Mistress R and told to kneel and wait for the Head Mistress with my hands behind my head. I was shaking from nerves but knelt quietly as my diaper got a little more wet. Everything looked surprisingly elegant and comfortable. When Mistress S came in she sat in a chair and had me crawl over and kneel in front of her. We discussed the nuts and bolts of the scene I (you) wanted to create. She said you told her that I was to receive a strap on, tease and denial, diapers (of course), spanking, and bondage all in a situation where she would play the role of my unsatisfied girlfriend. She was so enthusiastic and sounded very into the scene we were creating and said she had an amazing conversation with you Sir. It was then she said that anal play would be more fun if I was cleaned out with an enema...so I said that yes I would consent to that. She stood and said that you had told her if I was allowed "release" at the end I would have my key with me. I blushed hard and stuttered as I said, "I'm not allowed release ma'am and was not given my keys." She smiled and asked me to explain. I told her that you were my owner and that you controlled my orgasms. I explained that I had been in chastity for almost 6 weeks under your control and that you said I wasn't allowed to orgasm tonight.

Now she seemed even more interested. She said since you and I had similar voices she just thought the phone conversation setting this up had just been me playing a role. As she walked around behind me while I remained kneeling she told me that as a real lifestyle submissive that she would be expecting more from me and said that it was a good thing I wanted to play with diapers too since I must leak like a faucet from my chastity. I admitted that I did and that diapers were necessary anyway because you require them on me at all times except work. She looked surprised and asked if I was already wearing diapers then, to which I replied, Yes ma'am. She immediately instructed me to "stand, arms remain behind head, legs slightly spread." As I quickly tried to stand Mistress S giggled a bit from behind me and said that now she noticed the crinkle. She came around in front of me and with a finger under my chin moved my head to look her in the eye. She put a hand to my crotch and squeezed the saturated padding between my legs. In a low voice she asked if I had "pee peed" my diapers.

Made even more embarrassing by having to look her in the eye, I replied "yes ma'am I have wet my diaper twice."

She patted my diapered crotch and said, "of course you have haha. Now back on your knees and wait for Mistress R to come collect you."

I was back on my knees when Mistress R returned and lead me to the room we would be using. We went up a few flights of stairs and entered a room decorated a lot like a highschool girls room. She stood about 5 feet from me and told me to strip. She looked right at me as I undressed, never looking away. I was thoroughly embarrassed and could feel her eyes on me. I slowly started to remove my jacket and sweater and was told to move faster..."yes ma'am." I got to my pants and unbuttoned and unzipped them. She continues to look at me and says "well, continue, all the way to just your diapers boy", "yes ma'am." I let my pants fall to the floor and stepped out of them and folded them. Every movement seemed to make my diaper crinkle louder. Mistress R directed me to lay on the bed on top of a towel on my left side while she prepared my enema.

I felt so exposed laying there and without warning felt my diaper being pulled to my knees. I could feel her gloved finger covered in lube going in and out of my bottom. As the tube was slid into my bottom I could feel a large bead of precum leak out of my chastity device. Apparently Mistress R noticed it as well and while the warm water filled me up she wiped the drop from my leg with her finger and brought it to my mouth. I instinctively opened my mouth and sucked her finger. Though I couldn't see her, I could tell by the way she said, "good boy" that she was pleased with me not having to be told to open my mouth. Mistress R commented on how well I was taking the enema and when the bag was empty she pulled my diaper back up and had me hold for 5 minutes. While I was holding it she asked me to tell her about my owner. She was quite interested to know why a straight man would serve a male dominant and I did my best to explain that as a lifestyle submissive I am attracted to control and strong personalities no matter the gender. She was so good at administering my enema and holding the entire bag for that long was easier than I have ever experienced.

I was abruptly cut off from telling her about my owner by a slap on my diaper butt and a command to stand. I was walked to the bathroom and told to kneel and expel the enema then knock on the door when I was done. As she closed the door I asked if I could use the toilet. She just laughed and said "no you will use your diaper" and closed the door. I was in there a while, almost 10 minutes but finally my belly felt empty and my diaper felt very very full. I can honestly say, Sir, that at that time I had never been more humiliated. I knocked on the door and Mistress R opened it, commented on how bad I smelled and how ridiculous I looked kneeling in my messy diaper. I was then lead back into the bed room and told to wait on my knees hands behind my head for Mistress S. I was nervous, I could feel my diaper and how full it was. I was acutely aware of how I smelled and I was acutely aware of my penis pushing very hard against the steel chastity device. I almost lost my nerve and started to stand up when Mistress Scarlet comes in and is dressed in an incredibly sexy professional manner and says, "you were told to remain on your knees diaper boy, after the conversation I had with your owner I really expected more from you."

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