Mistress Chronicles Ch 01

Subject and background.

This is a recap of my first in-person session with a submissive. The subject passed the various pre-session requirements described in my second story "A few good subs" and after an extensive interview and evaluation process I offered him the opportunity to do an in-person session.

I'll admit upfront that I was a novice at this point, as was my subject. Still, despite out inexperience we had shared several sessions which I think most true submissives would find fascinating and pleasurable. The transcript which follows is edited, but comes from the video recording which captures the session.

My subject is slightly heavyset, 36 years old, about 5' 7" and 180 pounds. He has an administrative role for a large company. He is turned on by a number of fetishes, but seems to thrive on the idea of being gradually transformed into a sissy maid and forced to serve me in various ways. When we first started corresponding he did not have a girlfriend, although recently he indicated he has started casually dating.

Prior to our first session we met for coffee where the subject was provided a copy of my contract and I explained in detail what he could expect from me and what I demanded of him. After some discussion and consideration, we agreed on the parameters of our arrangement and the contract was signed.

First session plan

Subject will obtain a room at a designated motel. He has been instructed to check in at 4pm and our session is to begin at 5pm. When he checks in he will be given an envelope containing a blind fold, a pair of cheap clip on earnings and a note which reads as follows:

"Up the street from this hotel is a large discount retail store. Go to that store and buy yourself at least a three pack of panties in your size. Styles and color are up to you. I will arrive at 5pm sharp. When I enter I will find you kneeling in the middle of your hotel room wearing nothing but the earrings, the blindfold and a pair of your new panties with the other two pairs laid out nearby. I won't have a key to your room so be sure to either stop the lock or leave the door slightly ajar.

* * * * *Session transcript * * * * *

In a Spanish accented voice "Housekeeping, Hello?!"

Laughter....in my own voice "Well well, look what we have here. It's a good thing I'm not housekeeping or you'd be quite embarrassed. Don't get up, I'm just setting up my video camera to record our session. It looks like you've done a good job of following my instructions. The mint green panties are very cute."

I pull a couple of items out of an oversized bag, adjust the camera a bit and turn on some lights. Laying my suit jacket over a desk chair I approach the subject and stand in front of him and quite close so that I'm towering over him as he kneels. I'm wearing a tan business skirt, light blue silk blouse with several buttons undone -- a lacy navy blue bra can be seen at just the right angle. I'm wearing nude colored stockings and 4 inch caramel sling-back heels.

"Seeing you kneeling there in your panties is arousing and pleases me. I enjoy watching men like you submit. Are you ready to begin your training with me? I'll remind you that this first session is introductory for both of us. Are you ready to begin?"

"Yes Ma'am"

"Good. As you've learned you may call me Ma'am or Mistress. You're not to speak unless spoken to and I expect you to follow my orders completely and promptly. You're here to serve me, I'm not here to serve you. Clear?"

"Yes Ma'am"

"I see you are quite hard inside those panties, does it arouse you to submit to me?"

"Yes Ma'am"

"Are you nervous or is that all you have down there? It doesn't look like much from this angle."

"I guess that's all I have Ma'am. I think it's about average."

"Average. Yes. Well, I'm sure you'd like to think that. Don't fool yourself, it's nothing special. It's a good thing you've come to me for training because I don't see many women being satisfied with that. If you become a good maid and toy boy maybe your girlfriends will at least let you give them some oral."

"Yes Ma'am. I hope you will train me. I want to learn to serve you."

"Nice, but just words. We'll see what you're capable of.

Before we begin we'll need to give you a name to be used during these sessions. I've come up with two choices let me tell you about them. My first choice I'm increasingly confident about especially after seeing you kneeling down there. My first choice would be to call you Tiny since you're kinda short for a guy and clearly don't have too much equipment down there. What do you think of that?"

"As you wish Ma'am. I am short."

"My second choice would be to call you Muffin. You are small and sweet and carrying a little extra weight just like a muffin. I think I've made up my mind, but I'll ask you what you think. Just remember that anytime I give you a choice it has consequences, so which do you want to be my Tiny or my Muffin."

"I'd like to be called Muffin Ma'am."

"Really? I'd pretty much made up my mind to go with Tiny, but I'll hear you out. Why would you like to be called Muffin?"

"It's not really that I like Muffin....err, well, they are both good names, but I've been called Tiny and Small Fry and stuff like that all my life because of my size. There's not much I can do about that so I don't really like Tiny that much, but it's your choice of course Ma'am. You asked what I liked and that's why I picked Muffin."

"That's a reasonable answer and I'm not a mean mistress. You want to be called Muffin so Muffin it shall be. Maybe Muffie some times too. That has a nice ring to it. You're my little muffin. Muffie the sissy maid. Why don't you try it. Who are you?"

"I'm Muffin Ma'am. Thank you Ma'am."

"Good, so that's settled. I'll remind you later, but your first homework assignment will be to set up an e-mail address that includes your new name. From now on that is how I will communicate with you.

Now, on to business. The first thing you must learn is how to greet me. Let me remove your blindfold, but keep your gaze turned down at my feet.

So when you have been invited to be in my presence I will expect you to promptly kneel before me at about this distance or where specified. When I'm ready to acknowledge your presence I will slide my left foot slightly forward.

You will kiss the toe of my left shoe and then say 'Thank you mistress for allowing me to serve you.' You will then kiss the toe of my right shoe and say, 'It is my honor to serve you and all women.' Go ahead and try it.

"Thank you mistress for letting me serve you.'

"It is my uhh, honor to serve you."

"Close, but not good enough. The phases are 'Thank you mistress for allowing me to serve you.' And 'It is my honor to serve you and all women.' You must say it correctly, clearly and with sincerity. No umms or uhhs. Again.

"Thank you mistress for allowing me to serve you.'

"Umm its my honor to serve you and to serve all women."

"Better, but still not correct. Once more. 'Thank you mistress for allowing me to serve you.' And 'It is my honor to serve you and all women.' Go ahead."

"Thank you mistress for allowing me to serve you.'

'It is my honor to serve you and all women.'

"Louder"

"Thank you mistress for allowing me to serve you.'

'It is my honor to serve you and all women.'

"Once more, very loud. If we have neighbors I want them to be able to hear you."

"Thank you mistress for allowing me to serve you.'

'It is my honor to serve you and all women.'

"That will be enough for now. Be sure to practice this. You must be perfect on this or you will be punished, it is just the least of the things I will teach you.

I think we need to talk about your girlfriend for a minute. What did you say her name was?"

"I don't think I said Ma'am. It's Tammy Ma'am. We've gone out just three times."

"(Sternly) Keep your head down and focused on my feet. I'll let you know if you may look at me. It was good that you mentioned her. It's normally my rule I won't do sessions if you have any attachments. I made an exception in your case because I doubt it will last. So tell me about Tammy, is she pretty? Is she a good cook? Why did you ask her out when I was training you on-line?"

"No Ma'am. I'm sorry Ma'am. She's, someone I've known awhile and she's like a friend so I thought...well."

"Is she pretty? Let's say I'm and eight out of ten, what's Tammy?"

"You're not an eight Ma'am. You'd be a ten. She's maybe a six."

"Yes, so she's four points less than me is what you're saying. So if I'm an eight Tammy is a four. So tell me about Tammy the four. Does she have big breasts? Does she dominate you too? What's the story? What's her best feature?"

"I guess......I don't know, she's just nice. I guess, I'don't know, she has a cute butt, Ma'am."

"A cute butt. Tammy the four has a cute butt and I bet you've already dreamed about kissing it. You'd make a good ass licker. Have you kissed her butt yet? How far have you gotten with her? Does Tammy the four put out for you?"

"No Ma'am. I've only kissed her good night."

"Just as well then. I'm sure she'll be disappointed when she sees what you're packing. I expect even Tammy the four has seen better than that. It would be Muffin's four for Tammy the four...ha, ha..

"So you said she's nice. Don't you think I'm nice?"

"You're nice too Ma'am. She's just, you know, a friend. I didn't know if I'd ever get to see you. She's just, someone to go out with. When I'm not serving you. I want to serve you."

"So I asked you to get rid of all of your body hair before this session. What will Tammy the four have to say about that. Does she know you keep shaved? I wouldn't want Tammy the four with the sweet butt to be angry at me. What's the story?"

"I don't know Ma'am. She won't know for awhile probably."

"So what will you tell her when she asks? Will you tell her the truth, that your Mistress made you get rid of the hair so you could get sissy training? Will you tell her that?"

"No. I mean...I'd have to come up with something...uhh Ma'am."

"Yes well, I guess it's good to know you're in the habit of lying to your girlfriends. I'm sure you know that if you lie to me there will be consequences.

Please stand for inspection and thank me for making you get rid of your nasty body hair."

"Yes Ma'am, thank you Ma'am. Thank you for asking me to get rid of all of my body hair. I want to be a proper clean shaven sissy for you."

I spend a few minutes generally inspecting the shaving job, which as far as I can tell is pretty thorough.

"It looks like you've done a pretty good job. I expect you to maintain at least this level whenever you are in my presence."

"Yes Ma'am"

(Removing a razor from my purse) "Please go to the bathroom and double check the area around your tiny dick. I'm not going to remove your panties to check right now, but if I do, I want that cock which is about the size of an eight year olds to look just as bald -- got it?"

"Yes Ma'am"

Subject heads to the bathroom as ordered. I check the contents of the mini bar, pull a few items from my bag and then make myself comfortable in an easy chair in the corner of the room picking up a magazine and that I begin thumbing through.

Subject emerges from bathroom, looking puzzled as to what he should do.

Excuse me, Ma'am? I've checked my shave. Should I kneel?

I ignore him and continue to look at my magazine for about five minutes. Subject stands nervously awaiting a response.

"Did I ask you to speak to me? Could you not see I was reading?"

"No Ma'am. Sorry Ma'am. I should have waited for you to address me."

"Do you think you should be standing?"

(Kneels) "No Ma'am. Sorry Ma'am."

"Why are still wearing panties? Do you think I can inspect whether you've done a good job with panties on?"

(Blushes, head down) "No Ma'am, sorry Ma'am. This is all new to me. I didn't know what to do? Sorry Ma'am."

"Your apology is noted. Lose the panties and come stand before me, hands above your head."

Subject leaves panties and walks naked to stand in front of Mistress, his nakedness a contrast to mistress in her professional dress.

Mistress leans forward to inspect his legs, then indicates with a small hand gesture for subject to turn around. "Hmmmm, good enough, I suppose. Its hard to believe, but that cock looks even smaller with no hair around it. You look like an eight year old. Go put your panties back on and come back here."

Subject retreats to where he left the panties, returns a few seconds later wearing the plain mint green nylon panties he wore at the beginning of the session. His hard cock tenting the front.

"Submission really makes you hard doesn't it boy? You'll be whacking off for days over this won't you?"

"Yes Ma'am. Probably."

"Well, we have a solution for that. It will be part of your homework. For now though you still need some maid training. Let's start with a nice apron. I'm sure a mama's boy like you knows how to tie on a nice frilly apron. Can you do that?"

Mistress hands over a full ruffled pinafore/apron. Subject puts the top part over his head and then ties the strings behind his back.

"Not bad. You have some practice with aprons don't you? How about a nice curtsey now. No, maybe not. You'll need training on that. Lets finish the dressing. My goodness look how hard you are? If you get any more excited you might become Muffin the five.

Lean forward, I think a good maid needs a bit of lipstick don't you?"

"Uhhhmmm, yes Ma'am. Thank you Ma'am."

"Ask for it."

"May I please have some lipstick Ma'am. I want to be a good maid for you and a sissy maid should have lipstick."

"Yes I think you're right. From now on, when you are in my presence I expect you to be wearing panties and lipstick. Understood?"

"Yes Ma'am. Panties and lipstick."

I apply an exaggerated swath of bright carmine red lipstick all around his puckered lips.

"There you are. One very adorable hairless sissy maid in panties, pinny, lippy and earrings. You forgot about the earrings didn't you. Maybe a thank you would be in order?"

"Thank you Ma'am. Thank you letting me be your maid."

"Ohhh, you're far from my maid. My maid wouldn't look like a man in an apron. My maid would be fully feminized from head to toe. No. You're just a sissy-boy not even a sissy girl. A sissy with a small pitiful cock that enjoys serving women. You have a long way to go to be my maid.

Why don't you go look at yourself at the mirror for a few minutes. See how very pretty you look. Get a good image of your humiliating appearance in your mind."

Subject goes to a mirror and stands looking at himself in the full length reflection

"Go ahead get a full eyeful. Raise your apron and look at your hard little dickie in the pretty panties. Let's see some nice lipstick pouts as well. This is what you wanted. You wanted to be a sissy maid. I don't want you to think I didn't give you a chance to really enjoy the experience."

Red faced subject raises his apron and makes some kissy faces at the mirror while looking at himself. He remains there for about 10 minutes while mistress periodically taunts him.

"I see you've added some blush to your look, very pretty."

"Don't stain those panties now, a maid must be neat and clean"

"Dance a little while you watch yourself, practice being graceful in your ruffles"

"Put your hands on your hips and give me a pretty little pouty face now"

"Show some dimples while you smile at yourself"

"Enough for now, come back in front of me and show me how you curtsey."

Subject crosses the room and stands about three feet in front of mistress. He curtsies by bending slightly and crossing his left leg slightly behind his right.

"My goodness Muffy, you already know how to curtsey quite well. Did Tammy teach you that? Do you curtsey for her? Or was it your Mom or aunty that taught you to be such a good girl?"

"Thank you Ma'am. I just practiced myself."

"A sissy even when no one is around. You must be very proud of yourself, spending your time perfecting your sissy skills on your own. Once more please, but dip a little lower and I'd like to see you point your toe a bit as it slides behind. Also please say 'My pleasure Ma'am' as you do it."

(Subject curtsies as instructed) "My pleasure Ma'am."

"Let's see your maid skills. I could use a drink."

"May I get you something to drink Ma'am"

"A curtsey please as you take my order. Again"

(A deep curtsey as instructed) "May I get you something to drink Ma'am."

"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 Ma'am. I don't have any ice Ma'am. May I get you something different?"

"Perhaps a curtsey would be in order when you tell me you are sorry that you are not able to meet my needs. A little deference goes a long way for a maid. Perhaps there is a good reason why you can't go down the hall and get me some ice for my drink?"

(Curtsey) "Ummm please Ma'am. I can't, I mean, it wouldn't be appropriate, like this I mean...."

I leave him hanging for a few minutes glaring at him with as hard of a glare I can muster. While I don't want him walking the halls as he is, I want him to think that is what I'm considering.

"Yes well. I can see you're not quite ready for that. I'd be embarrassed for anyone to even know you were training with me. Perhaps a scotch and water then. Just tap water will be fine. Not too much."

(Curtsey) "Yes Ma'am, right away Ma'am. Thank you Ma'am"

Subject prepares drink as requested and returns. Curtsies and places drink beside Mistress on the nearby table. He stands awkwardly for about 30 seconds, being ignored, then kneels.

(Mistress takes a sip of the drink) "Not bad muffie. There is hope for you yet. Put the blindfold on and remain in position, hands at your side while I finish my drink. So you will have something to do, when you hear me place my glass back on the table, I want you to rub your little sissy boobies for one full minute. Make your little nipples nice and aroused.

Please be sure you're not leaking into your panties as well. I know I said you'd have an opportunity for release this first session and I will give you that when I'm finished."

I pulled a small vibrator out of my bag and rubbed it against my clit, through my stockings and panties. As I had hoped, it was quite arousing bossing him around and his sissy blushes had made me quite wet. The hum of the vibe could be plainly heard and it was clear Muffin was very hard at the thought of me bringing myself off right in front of him. Several times his arms twitched from his side as he fought the urge to touch himself.

For the next thirty minutes I teased myself periodically emitting moans of pleasure. I also took regular sips from my drink and occasionally set the glass down without sipping it just to make him tease himself.

While watching him kneel before me was arousing, I wasn't quite able to bring myself off although I was definitely highly aroused and soupy wet. Deciding to leave myself unfulfilled, I repositioned myself, put away my toy and continued the session.