Title: Decision time
Background/update
Even if you've been following the last couple of stories about my subject, Muffin, you might want to read this background as there are a few new points of note.
Muffin is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professes to be most interested in being gradually transformed into a sissy maid and forced to serve in various ways.
He has a girlfriend named Tammy and they have now been dating for nearly six months, the last three of which have been 'somewhat serious.' I have contemplated ending my relationship with Muffin as a result of this as I have no desire to deal with an angry girlfriend. I'm happy to be a dominant mistress, I'm not that interested in interfering with a relationship
My experience as a dominant mistress has definitely grown through my personal interactions with Muffin. That said, I realize that I have allowed the Tammy situation to go on too long and must force a conclusion even if it means the end of my control over Muffin.
The session I am about to describe comes about five months after the one in my last story. Some of the intervening sessions might be the source of future stories, but for the most part had a common pattern – a review of assignments, a new test or task that resulted in some humiliation and then either relief granted to him via some type of demeaning masturbation or having his release denied.
In the course of these exercises, Muffin has become much more practiced as a serving maid and willingly accepts feminization in my presence to the point where this is only a very modest source of incremental embarrassment to him. Said differently he's more turned on by being dressed as a maid than embarrassed by it, forcing me to find other means of securing his compliance and submission.
His self control has also improved and he keeps a journal of his masturbation sessions, which are now limited to once per week. He is also not allowed a release unless he is dressed in his maid attire, reinforcing a link between his submission and pleasure.
I also receive detailed accounts of his dates with Tammy and their now occasional light sexual activities. This journal is a serious point of control for me as I have kept copies of every entry. He remains very afraid of the idea that I will contact Tammy. This is undoubtedly his greatest fear and I regularly use this to deepen his submission.
For the last couple of sessions and in all of our interactions since our last meeting I have advised him that this session will test him and that he'll be "pushed to the next level or left behind." He has expressed some uncertainty, but has said he remains willing. We shall see.
Session plan
I have obtained a room at a designated downtown hotel. Muffin is to arrive promptly at 5pm. He is allowed to wear male clothes on the outside, but underneath he is to wear a pink satin bra and panty set that has loads of ruffles and lace and is very sissy. He is also to be wearing a garter belt with seamed pink stockings which I provided him at a prior session. He will be admitted to the room and ordered to change into an outfit awaiting him in the bathroom. Our session will begin when I summon him.
I am dressed to show some dominance. I'm wearing a black short suit jacket and very short black skirt. My ruffled high neck white silk blouse clings to my breasts which are being pushed up and out by a white satin bustier. My hair is tightly pulled back and my face is made up in the classic dominatrix theme of crimson red lipstick and black smoky eyes.
I've treated myself to my first piece of fetish gear – thigh high shiny black leather boots with several shiny silver buckles up the back, and four inch stiletto heels. My sheer black stockings are attached to the garter straps on my bustier. My skirt is so short that the stocking welts can be seen when I sit.
* * * * *Session transcript * * * * *
At my summons, Muffin enters and completes his transformation in the bathroom. When finished, he crawls to me and kneels before me as I sit in a comfortable chair with my bag of tricks on the floor next to me. Apart from the pink bra, panties, stockings and garter he arrived in he has added a pink dance leotard, a frilly pink apron, pink lipstick and lip gloss, dangly earrings, a bit of eye make-up, ruffled pink ankle socks and pink high heeled shoes. He would not pass as a female by any means, but his outfit screams sissy maid and has been added to piece by piece to reach this level.
After about two minutes, without a word, I slide my left foot forward.
(Subject kisses the toe of the left boot I have extended) "Thank you mistress for allowing me to serve you.' (Subject kisses the toe of the right boot) 'It is my honor to serve you and all women.'
Removing a cloth from the pocket of his apron, he quickly buffs away the lipstick he has left behind on the toe of each of my shiny boots.
"Since we met you have begged for the chance to serve as my feminised maid. Tonight you will have that opportunity and will be tested. Please remind me of your safe word."
"My safe word is pancake, Mistress."
"Good Muffin. Tonight I am only to be referred to as Mistress. You will only speak when spoken to. You will give short clear answers. No casual talk, no ums and uhs. If you are ever to become my sissy maid I expect you to be compliant, professional and seen, not heard. Clear?"
"Yes Mistress."
"Give me your journal."
He produces it from a pouch in his apron and wordlessly hands it to me. I spend a minute or two looking at the entries which describe several dates with Tammy and two masturbation sessions.
"So it sounds like you had a very nice date with Tammy last weekend. Was the best part going home and dressing up like my sissy and jerking off?"
"Yes Mistress. It was most enjoyable. Thank you for allowing me that priveldge."
"You and Tammy are pretty serious now aren't you?"
"I guess you could say that Mistress."
"Yet here you are sneaking out on her to spend time with me. You must really feel the need to submit."
"Yes Mistress. I love submitting to you. Thank you."
"Where does she think you are tonight?"
"At a friend's house playing video games, Mistress."
"Why don't you go stand in front of the mirror and call her. Tell her you are thinking about her. I bet you'd enjoy talking to her while you're all dolled up."
"Yes Mistress. If you want me to."
"Of course I want you to. I want you to stare at your sissy image in the mirror and talk to your girlfriend. I want you to pay her a compliment or two as well. I'm going to be listening and making sure you are just as submissive and sweet to her on the phone as you try to be when serving me. I want to see if you're learning your lesson about serving women. I realize at this point that I'm preparing you for her. She is a woman and so you must serve her. "
"Yes Mistress."
He crawls off to retrieve his phone from the bathroom where he has left it and the proceeds to stand in front of the mirror and dials. His side of the call went like this.
"Hi. I was just thinking about you and how good you looked the other night so I wanted to give you a call.
We're taking a break. He had to go to the bathroom
No. It's cool.
