Mistress Chronicles Ch. 03


Title: Decision time

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 ankara türbanlı escort 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.

I don’t mind when they give me a hard time. I like being with you.”

At this point I stood and walked over to him and motioned for him to kneel. As he did so, I stood close to him so my shiny black boots were just inches away from him and I towered over him.

His call continued “You have fun tonight. I won’t be too late.

Maybe midnight.

Ok. I’ll call.

Yes I’d like that too.

I’ll take you for some ice cream maybe.

Good night Tammy.”

“Very cute muffin. It must be nice talking to a girlfriend while kneeling for a mistress. Do you like being dominated by two women. Does Tammy own you the same way I do?”

“No Mistress. Tammy doesn’t own me. Only you do.”

“Why not? Why haven’t you given yourself to her. Do you serve her? Do you get her drinks? Do you rub her back and her feet like you’ve been trained?”

“Yes Mistress. Sometimes.”

“Good. The next time you see her, you need to tell her how much you enjoy doing things for her. You need to keep going deeper under her control. It may not be as sexual as what you get from me, but you will be submissive to her, do you understand?”

“Yes Mistress.”

“Good. Now let us see how you have progressed on serving. I would like a drink.”

“May I stand Mistress?”

I retreat back to my comfortable chair and once I’m seated comfortably I nod and give him permission.

Subject stands and does a deep curtsey. “May I get you something to drink Mistress.”

“Yes you may Muffin. I’ll have a Grey Goose on the rocks.”

Subject heads to the mini bar and removes a miniature bottle of Grey Goose, then returns to stand in front of Mistress silently waiting to be recognized.

After a minute. “Is there a problem Muffin? It’s quite a simple drink.”

“I’m sorry Mistress. I don’t have any ice Mistress. Should I leave to get some, or may I get you something different (deep curtsey).”

“I see no reason for you not to get some ice for my drink. There is a key card on the desk over there, take it so you can get back in.”

(Curtsey) “Ummm please Mistress. This is a nice hotel, I mean, it wouldn’t be appropriate, like this I mean….”

I hold up my phone and take a picture of him. “Are you getting ice or will I need to send this picture to Tammy’s Facebook page? She friended me you know.”

(A look of surprise) “Sorry Misstress. I’ll get the ice. May I ask a question?”

“You want to know how I was friended don’t you? It was pretty easy really. I’ll tell you after you bring the ice. Don’t try my patience.”

“Yes Mistress. I’ll be right back Mistress (Curtsey)”

Muffin walks across the room, picks up the ice bucket and tuzla escort goes to the door. Peers out and quickly slips outside. The ice maker is located in a room which is directly across the hall so the risk of being caught is extremely low. About one minute later, he returns with the ice bucket and proceeds to make a Grey Goose on the rocks.

(Curtsies and holds drink out). “Your drink Mistress. May I get you anything else?”

I take the drink from him and he curtsies again. After one minute he kneels in place, head bowed.

“I believe I have you to thank for my new friend Tammy. You see you once told me about her arts and crafts hobby and how she posts on certain craft websites. What you may not know is that she posts under her own name, which probably isn’t that bright but then again she doesn’t have anything to hid like you do.

I went on one of the sites you mentioned and pretended I was interested in the same crafts as her. I made up a name and posted ideas and told her how great her ideas were and things like that. She flatters quite easily it seems and she started posting replies to me and giving me more ideas.

After awhile I offered her to friend me at my made up page and she friended me back. Pretty clever wasn’t it Muffin? I’m Country Courtney_xoxo on her friends list by the way and I love cross-stitch and smocking. You can check me out, I have lots of pictures of cats and smocked sissy dresses and frilly girly stuff…You’d like some of the dresses, if they were your size that is.”

“Yes Mistress. I will Mistress. Check it out I mean. Please be nice to her. She’s a nice girl and she wouldn’t understand all of this. Why I do it I mean.”

“She seems like a very sweet girl. Too sweet for a guy like you who spends his time dressing up like a sissy maid and begging permission to cum. She needs a man that will protect her and keep her safe, not a sissy boy.

I’m really not sure what she sees in you. A sweet girl like that has one goal – a nice hard cock to make her pregnant so she can focus her attention on her babies. I’m not sure where a sissy boy like you fits in. I’m not sure your little sissy dick will even be up to the task. You would need to hire a stud to mate her.

Anyway, she’s my friend now so now I can contact her by phone, email and web posting if I have anything I think she would be interested to know about. Do I have anything like that Muffie? Do I have any interesting things to share?

“Please Mistress. I’m begging. You know I’d do anything to not hurt her. Please.”

“Yes, I know. But you’re begging doesn’t arouse me as much as it used to. I think a little bit of actual suffering might be more to my liking. You want to protect her and yet you still come to see me. Can you explain that Muffie? Can you explain why you can hurt Tammy and I cannot?

“No Mistress. I can’t explain that. I’m sorry.”

“I think it will soon be time to make a choice Muffie. You can be my sissy or you can be Tammie’s sissy, but I’m not sure it will work much longer for you to be both. You said you would do anything not to hurt her. I think I have an idea about that. What would you say to being put into chastity with me as the keyholder? First reaction, speak freely.”

“I don’t think I’d like it Mistress. She would probably find out and then I’d have to explain.”

“You could do it Muffie. You told me she said no intercourse before marriage. You could tell her you got it for her. To show your commitment. How about that? She’d like that wouldn’t she little Muffin?”

“I don’t think so Mistress. She doesn’t know about these kinds of things. She probably doesn’t even know there are chastity devices and would be surprised to find out I had one.”

“So even though you said you’d do anything, that’s not something you would do? Are you lying to me or will you accept chastity? I’ll give you one minute to decide. Admit to lying or accept a cage.”

Subject kneels head bowed for nearly a minute. “I’m sorry Mistress. I must have lied. I will accept punishment. I cannot accept chastity.”

“Very well. I certainly am not going to leave you the impression that lying is acceptable. I’ll not take away the release you’ve earned, but any more disobedience and that will be the next step. What do you think would be a good punishment?”

“Its not for me to say Mistress.”

“Maybe you should go stand in the hallway for five minutes with your head bowed against the door. That would make a nice punishment?”

“Mistress, please. Someone might see me.”

“Aren’t you proud of being a sissy. A sissy that dresses up and admires himself in the mirror and serves drinks. A sissy that has a very nice curtsey and clean shaven legs so his pretty pink stockings look nice. You’re not proud of that?”

“No Ma’am. I mean, Mistress.”

“I think what I need from you now is to profess your loyalty to me. Nice and loud. I want to hear how you do that and what you say. I’m going to record it here on my phone. Prostrate yourself before me and profess you submission.”

“Yes Mistress. avrupa yakası ucuz escort Thank you Mistress.

I adore you Mistress. I thank you every day for taking the time to train me and teach me how to please you. I worship your feet. I love to serve you. Serving you is the most important thing to me. Your happiness is my happiness. I love being a maid for you and accept your punishments. I adore you Mistress. You mean everything to me. I love serving you and giving you pleasure…..

After a minute or two of this, which was becoming very repetitious as he struggled to think of things to say, I called a halt.

“Enough. The thing I’m not hearing is that I am your first priority. That I’m more important than Tammy. I’m not going to make you stand in the hall. But you can go stand in front of the window. Pull back the curtain and go stand in front of the window.”


“You heard me, go stand in front of the window and show the world what you are. I don’t’ want you in my sight right now. Oh, and hold up your apron so everyone can see your frilly panties and stockings. You need to think about Tammy and me and decide what you are willing to do to keep us both happy.”

(Hesitantly) “Yes Mistress”

We were many stories up and it was already dark outside. Unless someone was specifically looking at our window its not likely they would be able to see in anyway particularly with the lights low. He didn’t really know all that however, so I enjoyed his obedience and felt at least a small stir inside.

I let him stew there for about ten minutes and got myself ready for the next part of the session as it was going to be very critical. I called him back and had him kneel in front of me.

“So did you think about what I said? I told you we needed to push our relationship to the next level. I invited you to accept chastity with me as your key holder. Did you think about that and maybe change your mind?”

“Please Mistress. I don’t think I can do that. Please let me do something different.”

“You said you’d do anything to keep your secret from Tammy. Would you serve a man to keep your secret from Tammy? If I can’t own your cock, then maybe you should learn to serve a man with a real cock. Would you suck a cock for me Muffie?”

“I don’t know Mistress. This is all new to me. I’ve never done it.”

“You’re dressed as a sissy maid and you want me to believe you’ve never thought about sucking cock before?”

I lean down and retrieve an eight inch realistic looking dildo from my bag. Holding it by the base I extend it towards Muffie

“I think you want this Muffie and haven’t admitted it to yourself. Try this. It’s not the real thing, but it’s a good training cock. Ask me to suck my cock and then show me how you give head?”

Uncertain and head still bowed, he quietly says, “Please Mistress may I suck your cock? I want to learn how to do it so I can be a good sissy.”

“That wasn’t very convincing Muffie. A real cocksucking sissy would be begging with much more enthusiasm. Try again please.”

(More enthusiasm, but not much. Still fear in his voice.) “Please Mistress, please may I suck your cock. I want to be a cocksucking sissy. Please let me put your nice hard cock into my virgin mouth. I want to be a cocksucker.”

“Better. You may begin.”

Somewhat tentatively subject stretches his mouth over the top of the phallus and begins bobbing up and down a bit.

“That’s its sweetie, get a good taste of it before you try to take it all the way. Be careful around the top of that shaft. That’s the most sensitive spot and if you spend all your time up there you’re going to be eating some cum.

You probably like the taste of cum though don’t you Muffie. You’ve eaten enough of your cum by now.

Real man cum is much different though. It’s much thicker and there is a lot more of it. We’ll get you some practice in cum eating too. I want you to be prepared if you are choosing to become my cock-sucking sissy instead of my chastity sissy.”

(Subject continues about five more minutes.) “That’s enough for now, let’s see how you did.”

Examining the dildo which is smeared with pink lipstick “I guess that’s ok for a first time. This is an eight inch dildo and it looks like the lipstick prints run down to about five inches or so. This one isn’t that thick but it looks like you are at least getting the taste of cock. How about you thank me? A cock-sucking sissy always thanks a man for giving them cock.”

“Thank you Mistress for letting me suck your cock. I know I have a lot to learn. Thank you.”

“Yes, you do. You’ll need to learn how to take the whole thing and you’ll need to learn how to make them squirt and then how to clean-up. Let’s practice a little on that. I had told you last session that you had earned an orgasm for this session, so now you will get your chance. How do you like my boots muffin?”

“I love your boots Mistress. They are so dominant and shiny. They are perfect for you.”

“So here is the deal for you. You may worship my boots and pull on your little sissy stick while you recite the mantra you learned for your little jack off sessions. So you will kiss my boot, and say ‘Muffin only cums for mistress’ and then kiss my boot again and say ‘Muffin lives to serve all women.’ You will keep doing that until you cum. You may cum in your hand. Don’t forget you must ask permission to clean-up. Are you clear?”

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