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Mistress Chronicles Ch. 01

By: MistressMtoyou



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.


Mistress Chronicles Ch. 01



(I gulp down the last sip.) "You've performed well for a first time, you may remove your blindfold. We didn't do too much this session, but you followed orders well and showed a willingness to learn. I'm sure Tammy, the four, will be quite impressed with your new skills. Do you want to have another session?"

"Yes Ma'am. Please Ma'am. I would. I have much to learn"

"Very well, it will be arranged. Would you like to cum now?"

"Yes Ma'am. If it pleases you."

"I told you for this session it will be so and so it shall. You may go kneel in front of the mirror. Take off your panties and jerk yourself off with them while you stare at the pretty lipsticked sissy in front of you. Go ahead and get busy, if you take too long I'll tell you to stop until after I leave."

Subject moves over to the mirror and does as ordered. In less than five minutes he cums with a groan.

(Putting on my suit jacket and repacking my bag) "Go ahead and put those soiled panties in your mouth until I leave. I don't wish to see them drip cum while I am speaking to you."

Hesitatingly, subject begins to do as asked. There is quite a bit of cum in the gusset and front panel of the panties.

"Quickly. Do it. Sissies eat cum, it's to be expected. You are no exception. When you produce that nasty sauce you should fully expect to eat it."

Not happy, and clearly not used to tasting his own cum Muffin complies.

"Now listen carefully. After I leave I expect you to put on another one of the pairs of panties you bought and remain in them for 24 hours. No exceptions. That's assignment one.

Assignment two, as I said, is create an e-mail address including your new name, Muffin and forward that to me so I can communicate with you. Your old address is dead to me.

Number three you will buy an appropriate journal. In it, you will record every time you or anyone else handles that little dick of yours. If you pee write it down. If you touch it, write it down. If you jack off with it I want a detailed description of how you did it, how long it took and what you were thinking about while you did it. I will place no limits on your use of that little thing, but do not try to fool me. Your shame will give you away if that journal is not 100% accurate. Nod if you understand me.

(Muffin nods)

Number four you will get a small metal keychain which I want you to have engraved with your new name, Muffin. You will bring this to your next session.

Last, number five, and most important. In the next 72 hours you are to purchase an intimate gift for Tammy and give it to her. It will be your choice what it is -- lingerie, stockings, whatever, you choose. You will e-mail me a scan of the receipt, a photo of the item and a couple of paragraphs describing her reaction and why you chose that gift. 

I will only schedule your next session after I've received this from you. If I don't get it, that will be my indication you don't wish to continue. Nod if you understand me.

(Subject nods)

Mistress puts the blindfold back over his eyes. Puts the third pair of panties over his head and blindfold

"Don't move until you hear your room phone ring one time. You can't see, so don't assume that just because the door closes I have left. By the way, don't forget your earrings when you leave, even though they do look very nice on you.

Bye-bye Muffie.

Mistress gathers the video recorder and exits. Recording ends.



Mistress Chronicles Ch. 02



2 – Hurry

Background/update

In my last story, my new subject Muffin and I had our first live session. He 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. 

When we first started corresponding he did not have a girlfriend, although recently he indicated he has started casually dating a woman named Tammy.

The session I am about to describe comes two sessions after the one in my last story. The intervening session was fairly similar to the first one and included additional obedience drills. I've decided to omit describing them as somewhat repetitive.

By way of closing some open ends, Muffin completed all of the homework assigned at the end of his first session. He arranged a new e-mail address and bought me a nice keychain with Muffin engraved on it.

His journal of times touching his cock seemed a little incomplete and I rebuked him for this. He pledged to do better before the session I will shortly describe.

His gift to his girlfriend Tammy was a pair of back-seamed stay-up stockings. He asked her to go out for dinner and dancing and encouraged her to wear the stockings telling her he thought she'd look great in them. She apparently gave Muffin a hard time about his motives suggesting he thought she was easy. 

She did wear them however and they had a nice time. Muffin reported that they "kissed a little" at the end of the date, but she broke it off before things went any farther.

One of his homework items for the session described below was to ask his girlfriend's permission to make a further move with her during a following date.

Session plan

I have obtained a room at a designated hotel. Muffin is to arrive promptly at 5pm. I am wearing a tight, red knit, above the knee, cowl neck sweater dress, black leggings and shiny black stiletto knee boots. It is a very form fitting and sexy outfit. We will review prior assignments and will play a game to test self control. 

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

Knock, knock

"Greetings Muffin. Come in, strip, and stick your wallet, keys, personal items and shoes in the safe in the closet next to you. Fold the rest of your clothes neatly, then crawl to kneel before me with your journal."

I seat myself on the corner of the bed. Muffin crawls naked to a spot two feet in front of me. 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.' 

"Very good Muffin, it appears you are trainable after all. Please stand."

Muffin stands, in place, head down.

I slip a blindfold over his head and adjust it.

"Can you see anything?"

"No Ma'am."

"Good, hands above your head, close together."

I stand and fasten him into padded leather hand-cuffs with limited play between the cuffs.

"Very nice Muffin, you may lower your hands. I see you have a hard little dickie for me. You must like being restrained in addition to all of your other weaknesses. The only good thing about this is it will be easier to lock this cock and ball ring on you."

Mistress clicks a ring in place at the base of the subject's cock and fastens it closed with a small padlock. A short length of leather with a small bell on the end of it has been knotted onto the ring and dangles between the subject's legs. The bell gently tinkles when the subject moves.

"Kneel before me while I tell you a bit about our plans for today. I hope you got a good look at me in my very sexy outfit because it might be the last you see of me today depending on how you do. A friend will be meeting me here at 7pm and you have some tasks you need to perform before then.

As you may have figured out, in order to leave this room in any type of presentable manner, you'll need to earn the key to the lock on your cuffs and the lock on your balls. You'll also probably want the combination to the safe to get your belongings.

I'm sure my friend will be quite prompt and will probably get a good laugh at seeing you in whatever state you might be in, unless of course you earn your way out first. I've set the alarm clock for 7 pm so you'll know when your time is up.

Lets start by reviewing your little penis journal shall we? I had some questions about the accuracy of it last time, so perhaps before I look you can tell me how you did. Can you tell me how many times you jacked off since our last session....hmmmm must have been just less than two weeks ago."

"I have only jacked off twice Ma'am."

"Twice? Really, in two weeks? A sissy like you I would have expected a number more like 20 times or maybe more. Why only twice? Were you sick? In a coma? Why?"

"Last session you seemed to be angry at my lack of control. You said I came too quickly, so I practiced controlling my orgasms Ma'am."

"Admirable, but I'm still not sure I understand."

"I edged myself a number of times, but I only actually came twice. Once last Saturday after my date and then once yesterday, so I would be able to last for you today, Ma'am."

(Opening journal) "Hmmmm. I see what you've done. This isn't really what I had in mind. You seemed to have created a bit of a loop hole between edging and actually working yourself off to completion.....let's see here, how many edges did you record....I count thirty one times does that seem right?"

"I guess so Ma'am. I'm sure you're right."

"Hmmm this really won't do at all. If more control is what you want, more control is what you'll get. You have brought this on yourself. Not cheating really, but I think a breach of my intent.

I think its time for a new rule related to your journal and handling of that tiny little cock of yours. Starting now you will only be allowed to jack yourself off three times in a week and no more than five times in two weeks. Never two days in a row either. Starting now there is no distinction between edging or cumming. If you touch it to make it hard, it goes in the journal and is subject to these limits. Clear?"

"Yes Ma'am, sorry Ma'am. I wasn't trying to cheat. I thought I was doing something good, limiting myself and all."

"Well there's the mistake isn't it. Thinking. Thinking with your little head too, no doubt. Let's also change this journal. You don't need to record anything other than your little wank sessions. It will be a jack-off journal I suppose. 

When you record it I want lots of details– how you did it, what made you want to do it, what you thought about when doing it, how long it took, how you cleaned up, every detail of your little session. It will no longer be a private pleasure, you will share every bit of it with me. 

Don't even think of cheating, I will know if you don't record every session and every detail. I can crack a sissy like you in a second. Your face and the lie detector between your legs would give you away. You've failed with this journal twice already. There won't be a third time."

"Yes Ma'am. I understand."

"Well my plan was for you to worship my boots for one minute per orgasm, but clearly that won't do. I'm not sure how to judge thirty-one edges if those should count more or less. I'm going to say you have seventeen minutes of boot worship, fifteen minutes for the edges and two for the actual times you came. You may start now, I'm sitting right in front of you. You may kiss and lick my boots, but do not slobber. Begin."

Muffin begins actively kissing the toe, top and sides of mistress' boot. His bell tinkles occasionally as he adjusts position. I flip though the journal for a minute or two then hike up my dress and begin gently rubbing myself through my panties and leggings – his mistake has given me a delightful idea, which I am sure will prove quite entertaining and I am aroused thinking about how he will respond.

After the allotted 17 minutes: 

"That will be quite enough, you may stop. It's time for you to answer a few questions. I've been looking at your journal and I think you need to provide me a little more detail about your two actual jack-off session. Maybe you can begin with the one last night where it says you were thinking about me. Why don't you describe your fantasy in detail hmmmmm?"

(Blushing beneath the blindfold) "Yes Ma'am. I was just thinking of you and our last session. How pretty you looked at our last session, your sexy black stockings and the heels and I imagined that you had forced me to be your maid and to serve you and I kept thinking of what that would be like and eventually I couldn't control myself and just came in my hand."

"Do you think I like the fact you masturbated while thinking about me? Do you think that pleases me Muffin?"

"I'm, I don't, I mean, I guess I'm sorry Ma'am."

"You're not sorry Muffin, don't lie to me. I know pretty sissies like you get little submissive thoughts in your head and can't control themselves. I know that. That's why you're all hard right now aren't you. You're hard from kissing my boot and hard because I'm making you kneel before me. I'm sure if I ordered you to cum on my boot you would beg for the chance to do it and then beg me to lick it up afterward. I know you are weak and have no control.

Maybe you should tell me about this little session after your date. With Tammy I suppose. Tammy "the four", with the cute butt. Tell me about that session."

"Um, well, yes Mistress, of course Ma'am. It was Tammy. We had gone out and it was nice and we went back to her place"

"You whacked off at her place? Really?"

"No its, well, Ma'am you....my homework was....you know, to ask for permission. So after the date we went to her place and we were kissing and I asked her if it would be ok if I rubbed her breasts and well, she didn't want to at first but then she said O.K. So I did and....."

"What about her, did she take care of you? Did she give you a few strokes on the old sissy stick."

(Red faced) "She did, she rubbed me there a little, but then just when it seemed like things might go a little farther she broke off and said that was enough. She said it was her period."

"Hmmm. The old "on my period" excuse. I'll bet. More likely she got a feel of your little thing and decided it wasn't worth it. Could that be it?"

"I don't know Ma'am. I hope not. Anyway she had me worked up, so I went home and rubbed one out."

"Rubbed one out thinking about pretty Tammy. Tammy the four. I'm sure she'd have been very proud of that. She probably doesn't get guys rubbing one out thinking about her very often. Maybe you should tell her? Tell her how hot she made you. I'm sure she'd help you out next time. What do you think?"

"I doubt it Ma'am. Tammy's not like that too much."

"She seems like she'd be a good tease and denial mistress for you. Would you like that Muffin? Would you like Tammy to control your orgasms? Make you beg for them?"

"I don't think so Ma'am....she....I don't think."

"Do you know her phone number Muffin? Have you learned it?"

"Umm yes, yes Ma'am."

"Good. Maybe I should give her a call and tell her what kind of boy you are. Tell her how much you like to serve women? How you whack off thinking about her. How about that..."

(Very nervous) "No, no please. Please don't Ma'am."

"I think maybe you should trade one of your locks for her phone number. What do you think of that?"

"Please Ma'am. Don't do that."

"Yes, I think that's quite a fair trade. You give me the number and I'll release your cuffs. That's the deal. Stay in the cuffs or give me the number. You have a lot to do still and the clock is ticking. The number for a lock or you can decline and see what other opportunities present themselves. Which is it?"

(Head bowed submissively) "I'm sure I shouldn't but her number is 555-1234, Ma'am. Please go easy on me, please."

Bending down I unlock the hand cuffs.

"You need to trust me Muffie. I've always been fair and discrete. I might not even call her right away. I might save it for when you displease me and I'm sure you will sometime.

I bet she would like to know how you've been training to be a sissy maid though. As a budding T&D mistress she might like to know that. Maybe she'd like a little advice from me about how to control you, too. We could meet for lunch sometime....that would be a nice girls lunch. Me and Tammy the four talking about training our Muffin.

Look at you. Its making you drip isn't it? The idea of your girlfriend and mistress ganging up on you? Dominated by two women."

"Please, Ma'am. Please. It's....I'm sorry."

"Ohhh lookie at all that pre cum. You are so into this...."

(More emphatically) "Please, Ma'am, I'm begging. She wouldn't. She's..."

"Shhhh, shhhh, there, there muffie. I'm not interested in calling her right now. But it's nice to know how much that worries you. It's hard to believe but Tammy is another one of your weak spots. I'm going to need to think of another homework assignment involving her.

My goodness, look at the time. We still have a lot to do this session. Today I have a little game you need to play. Are you ready? Are you ready for a game?"

"Yes. I'm ready. Thank you Ma'am, about Tammy."

"I wouldn't thank me yet Muffin. I've made no decisions on that and I will call her when I please. Please pick a number between one and ten."

"I'll pick five Ma'am."

"Good. So this is how this game is going to work. We're going to get you dressed up in your sissy maid clothes and we're going to practice some control with a little edging. It's interesting that you had been practicing already isn't it?

So you picked five, so that will be five times you will need to edge. After each edge, I'll let you beg me for a piece of pretty sissy maid clothing. Here's the thing though. Your total time edging must total 20 minutes over the five edges. Each minute you are short of that total you will need to spend five minutes standing in the corner like a bad sissy. Understand?"

"Yes Ma'am. Ok, begin when I say go. I want to see nice firm strokes. Say 'edge' when you are close, but don't stop until I say stop. Go."

Subject begins firmly stroking his shaft up and down as ordered. The little bell between his legs beats out an embarrassing steady jingling, tinkling noise as he does so.

"Edge"

"Ok Stop. Not bad, that was four minutes and twenty-five seconds. You have a choice now. You can take a two minute break and then beg me for a pair of frilly ankle sox or you can start begging now, and then rest until five minutes are up. In any case, you will begin your edge again in five minutes. Your choice?"

"I'll rest first, Ma'am"

"Fine. Lean forward keep your nose pressed to the toe of my boot. I'll let you know when the begging should begin."

Two minutes pass in that position. I rub myself again at the sight of my naked submissive with his nose pressed into my boot. There was something very arousing about hearing the bell tinkle as he masturbated himself. I hadn't thought how delightfully humiliating that would be for him. I love the sexual power I am developing, it's very fulfilling. I can feel my juices start to flow.

"Beg me"

For a minute or so he begs along these lines. "Please mistress, please may I have a pretty frilly pair of sissy sox? I want them so much Ma'am. Please may I have them, Please?"

Mistress takes the frilly sox from a bag beside her and dangles them up to his lips, just brushing them. "Kiss them, thank me, and put them on. Then back to resting position with your nose on my toe until I say begin again."

Kissing the sock as he takes it from my hand. "Thank you Ma'am. Thank you for the pretty ankle sox." 

Muffin commences putting them on, which is difficult with the blindfold still on and then resumes position as ordered.

"Begin your edge again."

Subject sits up and begins firmly stroking his shaft up and down as ordered. Again the bell tinkles steadily in response to his submission. "Edge"

"OK. That was four minutes. You are up to eight minutes and twenty five seconds. Rest."

Subject resumes resting position. I stick my hand down into my panties and begin fingering myself in my now very moist slot. I continued for almost three minutes. Towards the end I'm sure subject could hear a few moist squishy sounds as I pulled my fingers in and out of my very wet hole.

"Begin begging for earrings now."

"Please mistress, may I have a pretty pair of earrings. It's important for this sissy maid to look nice and I would really like to wear a pair of pretty earrings. It would make my face look very girly and soft. Please."

"Enough. Sit up so I can clip them on you and then resume your resting position for about one minute."

Earrings are clipped on, subject resumes his position. I roll down the top of my leggings a bit to improve my access. The faint scent of my arousal begins to float in the air.

"Begin"

Subject begins firmly stroking his shaft up and down as ordered. The sound of the bell is incredibly arousing to me as a symbol of his submission. I rub myself steadily and it feels amazing.

"Edge"

"Mmmm not so good that time. You're getting behind. That's only three minutes and 15 seconds, so you have eleven minutes and forty seconds with two more to go. You'll need to average almost five minutes each to avoid the corner. Rest now. Try not to notice what I'm doing up here. Your submission is very arousing. I love a little sissy maid on her knees before me."

I resume fingering myself making no effort to hide the pleasure I feel or be discrete. I moan several times and the squelching sound of my fingers is very obvious. As subject sits back up I can see that his hard on didn't go down much at all.

"You may beg me for a bra this time."

"Please mistress, please let me try a pretty bra. I've never had a bra before and I would be so proud to have one from you. Please Ma'am, I'd really like to wear a bra over my sensitive sissy nipples..."

"Put your arms out." I fasten the bra around him. 

"Resume your resting position."

Seeing him with his nose pressed to my boot wearing a bra and sissy ankle socks is making my clit buzz. Its such a servile pose for him and his obedience and begging is effecting me much more that I had expected. I give myself a few more gentle rubs before telling him to continue.

"Begin."

Muffin begins firmly stroking his shaft up and down the bell jingling at every stroke. I begin firmly rubbing myself as soon as he begins. He can't help but notice the noise of my juices and gasps of pleasure. 

"Edge"

"That didn't take long. Two minutes and fifteen seconds. You are at thirteen minutes and fifty five seconds. I doubt you're going to make it to the end. Go ahead and beg for your panties right now."

His voice was a little breathy since he had clearly been holding his breath and straining to make it even as long as he did.

"Please mistress, please. Please can I have a pair of panties. You know how much I love panties. If it pleases you this sissy would like to wear panties for you. Please, pretty please..."

I let him keep it up for well over two minutes rubbing circles around my clit and occasionally laughing at him as he begs. Finally I rub the panties across his chest before placing them in his hand. 

He's dripping pre-cum and was evidently very close to cumming from his last edge. I help him a bit as he puts them on, still blindfolded 

"Resting position. I'll generously give you an extra minute or two."

"Thank you Ma'am"

It may have seemed generous, but after he spends five minutes listening to me rub myself he may think otherwise. I lie back on the bed and briskly insert my middle finger and then another and another.




Mistress Chronicles Ch. 03



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.

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 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. 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."

"Mistress?"

"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?"




Mistress Chronicles Ch. 03



"Yes Mistress. Thank you Mistress."

"You may begin"

(Kiss) "Muffin only cums for mistress"

(Kiss) "Muffin lives to serve all women"

(Kiss) "Muffin only cums for mistress"

(Kiss) "Muffin lives to serve all women"

(Kiss) "Muffin only cums for mistress"

(Kiss) "Muffin lives to serve all women"

(Kiss) "Muffin only cums for mistress"

(Kiss) "Muffin lives to serve all women"

This continues, but in less than five minutes subject releases a large load into his cupped hand, catching nearly all of it. As he has been trained, he waits to be acknowledged before speaking. I make him wait almost 10 minutes with cum drying on his hand, his cock shrinking and his libido fading.

"You have a question Muffin?"

"Yes Mistress. May I please clean up my mess now Mistress?"

"Yes you may. Please do it enthusiastically. A sissy needs to learn to eat cum and doesn't always get to do it when they want to."

"Yes Mistress, thank you Mistress"

Subject begins diligently licking his cum from his hands and between his fingers. His expression and limp dick suggest he's not enjoying eating 'cold' cum all that much. After several minutes he finishes the task, bows his head and awaits further instructions.

"So how did you enjoy your first lesson as a cum-eating cocksucker? All we need to do is put the pieces together and you'll be ready to try it out on a real man. Would you like that sissy?"

"Thank you for the training Ma'am...I mean Mistress."

"You didn't answer my question Muffin. I asked if you are ready to try a real man."

"I don't know Mistress. This is all new."

"I've got an idea. How about a little game of 'Would you rather' I'll ask you a question and you will tell me what you like better. It's a good game because there really aren't any right or wrong answers. Just say which one you'd rather OK?"

"Yes Mistress"

"Ok, lets start with an easy one. Would you rather have a week of chastity, or go down to the front desk dressed as my sissy maid?

"I would rather have a week of chastity, Mistress"

"Would you rather have a week of chastity or have me post your picture on my Country Courtney facebook page?"

"I would rather have a week of chastity, Mistress"

"See chastity doesn't sound so bad sometimes does it Muffin? Would you rather suck a dildo, or be fucked by one?"

"I would rather suck a dildo, Mistress."

"Would you rather suck a dildo or post you to my Courtney page?"

"I would rather suck a dildo, Mistress."

"Would you rather suck a dildo or have a week of chastity?"

"I would rather suck a dildo, Mistress."

"Would you rather suck a man or have him fuck you?"

(A little uncomfortable) "I would rather suck a man, Mistress

"Would you rather suck a man or have your picture posted?"

(A little more uncomfortable) "I would rather suck a man, Mistress."

"Would you rather eat a man's cum or be locked into chastity?"

(Starting to get agitated) "I don't think I would want to do either Mistress."

"You must choose. I think you've already made your choice. Just tell me. Would you rather eat a man's cum or be locked into chastity. It's not that hard."

(Uncertain) "If I had to choose, I would eat a man's cum."

"Are you sure? You would rather eat a man's cum than be locked into chastity and let me be your keyholder?"

(Quietly and with doubt) "Yes Mistress."

"Tell me loudly so I can hear your choice."

"I would rather eat a man's cum than be locked into chastity."

I reach into my bag and remove a stainless steel cock tube, the related locking plates and a small padlock which I hold up in front of Muffin and then silently place next to my left boot.

I then return to my bag and remove a condom, knotted at the top and apparently filled with cum. (It is not actually cum, but a theatrical recipe based on egg whites, flour and a few other ingredients that looks a lot like the real thing). I hold the condom up where Muffin can see it, un-knot the top and then squeeze a large blob of the contents onto the tip of my shiny right boot.

As I did all this, I was becoming fiercely aroused. This was the most bossy or aggressive I had ever been in these sessions. I had always been more focused on humiliation or small sexual games. This session was much more intense and much more real. 

It felt like it had consequences and there was a tremendous amount of dominant/ submissive sexuality passing between us. I could feel my power growing step by step. I was boxing him in and now I was going in for the kill. I could tell he knew it and I could sense his fear. Not just nerves, real fear. I hoped I would be rewarded with a moment of deep submission.

"I have told you for several weeks Muffin that this session would be a crossroads for you. I will now lay out all of your choices and you will decide how we are to proceed. Although you are clearly the submissive in our relationship, the choice will be yours alone. I will not coerce the decision.

Choice number one would be to accept chastity. If this is your choice you will reach for the device I've placed by my feet, kiss it and ask for it to be placed on you.

Choice number two will be to eat a man's cum. If this is your choice, you will clean the cum from my boot with your tongue, thank me and offer to do this for me anytime I choose.

Choice number three, as always, will be to use your safeword which you stated at the beginning of the session.

My phone timer is set for five minutes. If it goes off without you making a choice I will send the photo I took of you earlier to my Courtney Facebook page. 

Your time starts now."

The dejected look on his face was priceless. He was realizing, as I had, that today's session was no longer simple teasing and humiliation games, it was a real life decision and one which I showed every sign of pushing forward. He was coming to realize that he was about to cross a threshold from which there would be no easy steps back.

His body posture showed his defeat. His shoulders were slumped and his head was bowed staring at the cum laden boot and the chastity tube clearly in his line of vision. Sitting above him I couldn't see his face very well, but I could see the corners of his lipstick smeared mouth were turned down in a frown. His deep breathing told me he was trying to gather himself to make a hard choice.

The tension of the moment was very erotic. I didn't know which way he would go. I hoped he wouldn't safe word but was aroused at the possibilities of either of the two paths before him. Although he didn't know it, I had no real intention of posting his photo to a website, I was perfectly happy to let the tension build. 

I could feel the juices of my arousal leaking into my panties. No matter what happened, I knew I was going to need at least one good hard orgasm before the night was out.

It had been nearly five minutes when he looked up at me. Through the eye makeup and smeared lipstick I could see the dejection and his eyes had a glassy watery look like he was trying to hold back tears. I knew before he said it what he would do.

Softly he said, "Pancake, Mistress. Pancake."

I was disappointed in his choice, but remained aroused at how I had pushed him to it. I stared into his eyes with the strongest glare I could muster until he looked away in shame.

"Very well, you may leave then. Get your shirt and pants back on, you have less than 2 minutes to leave this room or I send the photo. 

I'll contact you with homework if we are to continue or a dismissal if we are not. You might keep an eye on my postings on Tammy's page to get a sense of where I am thinking. I will wait seven days before I make a commitment either way. Maintain your journal as normal until then.

Goodbye Muffin."

***********

Watching him leave, which he did without a word, was sad but also strangely empowering. I had put a lot of time into this relationship and I had learned a lot from it but in my heart I knew that it was best for both of us to move on. It was without a doubt the most unusual way I had ever dumped someone.

That night I ended up with my old friend Jeremy (the lawyer in story three). I told him about everything that happened and he helped me work out my sexual frustrations. He's such a sweetheart.

Seven days later I told Muffin it was done. He sent me a nice e-mail note and thanked me for the times we had and said he understood. I wished him good luck with Tammy and we parted on good terms. I never posted anything on Tammy's wall, but she never un-friended me either. About two years later I learned she was engaged to the person I knew as Muffin.



Mistress Chronicles Ch. 04



Background:  The next three stories involve my only long-term on-line subject who I have named Nancy.  This subject passed all of the tests I described in story two ("A Few Good Subs"), but before we were able to arrange an in-person session, he was offered a job in a town a great distance away, precluding any in-person meets.

We agreed to continue training via on-line sessions with the stipulation that they might be somewhat infrequent but that he would be required to maintain a high degree of diligence in meeting requests and maintaining a daily submission regimen.  After working out some details we agreed to try it out and the relationship continued for over a year.

Nancy is a computer nerd.  Brilliant at working with machines of all kinds, but hopeless with humans. He's not terribly self-confident unless he's writing software code, where he feels he's 'among the best.' He's early-thirties, slender, but not really physically fit.  Scrawny is the word one might use.  He admits to having little experience with women and that he has only had actual intercourse one time.  

He told me in high school the good-looking 'cheerleader' types used to taunt him and tease him about being a sissy and he secretly loved their humiliation.  He admitted to numerous jack-off sessions imagining various degradations at their hands and that their abuse, and the sexual thrill he took from it, is still essentially the basis of his sexuality.  

Apart from female domination, his fetish is lingerie and forced feminization.  Through our interactions he has gradually built up a sizeable collection of lingerie which he routinely wears to work under his outer clothes.

It's interesting to note that in the course of our sessions Nancy has never actually seen me.  I have sent him pictures that I have told him look similar to me, but never an actual face-shot photo.  He has a photo of a vagina that I have told him he may assume is mine which he is sometimes asked to stare at and say devotionals to, but its not mine, just a photo I ripped from the net.

The on-line session 
There are a number of different ways we do remote sessions.  In this one, I have recorded my commands in a sound file which the subject has downloaded to his iPod.  My commands total about thirty minutes with gaps between them.  He will respond to my commands during those gaps.

To insure compliance, Nancy will record the session on video and e-mail me the compressed file which I can view at my leisure. 

For this session Nancy is kneeling in front of a mirror dressed in sissy attire.  His iPod is in a docking station off camera turned up loud enough that my commands can be heard on the video recording.  The video is taken from behind him aimed at the mirror such that most of the view is of the reflection of what he is doing.

Session

"Hello Nancy.  Please begin by reciting my rules for being a good submissive"

Yes Mistress.  The first rule is to listen carefully and obey all instructions to the best of my ability.  Inattention to details or laxness in executing instructions will never be tolerated.  A good submissive knows that failure will be punished and understands when he has failed.

The second rule is to always be respectful to Mistress and focus all attention on serving her.  A submissive who is respectful and focused has the best chance to be rewarded.

The third rule it that a good submissive always knows his place.  They only speak when spoken to, do not question or talk back and accept that mistress knows what is best.

The fourth rule is that Mistress and only Mistress controls the submissive's sexual pleasure.  My cock belongs to Mistress and she will decide when, if, and how I am allowed to achieve pleasure with it and release if I have earned it.  A good submissive should expect violations to be punished.

The fifth rule is absolute honesty at all times.  A Mistress – submissive relationship is based upon mutual trust which takes time to earn but can be destroyed quickly.  The good submissive understands this rule is to be absolute and is one which will be given the least tolerance if it is broken.

The sixth is a good submissive will at all times wear at least one outward sign of his service and submission.  I always wear a pink and red woven bracelet around my ankle as a sign of my service.  I never take it off except to shower.

The seventh rule is that a good submissive will think about serving his Mistress even when she is not present.  He will think 'What would Mistress have me do?' and "How does this action help me serve my Mistress better?'  At least once each day a good submissive will pay his respects to his Mistress without being prompted, even when she is not present.

This morning I kneeled next to my bed, head bowed and silently thanked my mistress for taking the time to teach me how to serve her and for allowing me to serve her and to become a better person.

Thank you Mistress for allowing me to recite these rules.  They are a good reminder of what is important and what I must do to serve you well and earn your favor.

"You should know that your performance on your last remote session was satisfactory and has caused me to at least consider the possibility of granting you a release during this session.  I hope that will motivate you to be appropriately enthusiastic during this session.  Should I grant a release and this session prove slack, there will be consequences.  Please think about this."

Yes Mistress.  Thank you Mistress.

"If you are carefully following my instructions you should be dressed in a selection of sissy attire and kneeling in front of a mirror looking at yourself and just how submissive and pathetic you look.  While I can see what you are wearing, please describe each of your selections and why you have made them"

Yes Mistress.  I understand that I am meant to present as a sissy.  I have chosen my frilliest pink panties with lace around all openings and lots of frilly ruffles on the bottom.  I've also chosen matching pink ankle sox with lace on them and patent black Mary Jane shoes with a three inch heel.  I am wearing a pretty baby doll top with flowers and lace at the sleeves.  Underneath I am wearing a plain white training bra.  
I have chosen these items to show that I am still just a sissy in training and I need your instruction to be a proper sissy.  I hope you will find them submissive enough.  

"Take a good long look at yourself Nancy.  Do you like the person you see there?  Does it make you happy to be a sissy for your Mistress?"

Yes Ma'am.  I like to be a sissy for you.  It makes me happy to serve you.

"Its rather pathetic isn't it?   A grown man dressed up in little girl clothes?  Getting hard from dressing up like a little sissy boy?  Is this what you like?  Do you like to look all sweet and girly?"

Yes Ma'am.  I like to look sweet and girly.  It makes me feel good to dress this way.  It makes me feel submissive to dress like this for you and be all sweet and girly.  I'm not worthy to be a real girl.  I can only be a sissy boy.  Thank you for letting me dress like this for you.  Thank you for training me to be your sissy.

"What would your boss say if he saw you like this?  What about that girl that sits near you?  The one you think is pretty.  Do you think she would like you as a sissy boy?  Would she make you her pet?  Look at yourself in the mirror and think about her laughing at you.  Laughing at her sissy co-worker.  Just sit and look at yourself all dressed in your frillies and think about that."

There is a 3 minute pause while Nancy looks at himself

"It made you hard didn't it.  Being humiliated in front of a pretty, intelligent, dominant woman makes you hard doesn't it?"

Yes Ma'am.  I admit.  It makes me hard to think about being humiliated like that.  Sherri is very pretty, and smart.  She is like you.  I get hard thinking about submitting to her just like when I submit to you.  I just want to serve you so much and I feel so small and submissive dressed like this.

I know my place is at the service of an intelligent dominant woman but I know I'm not worthy as a man.  I can only hope I will be worthy as a sissy.

"What would you do for her if she was there?  How would you submit to your co-worker?"

I'd kneel before her and offer to kiss her feet.  I'd beg to be allowed to give her a foot massage or be allowed to clean her shoes with my tongue.  She has beautiful long red hair that she keeps in a pony tail, I'd offer to brush her hair or serve her any way she wanted me to.  

"See if you can think of a way to serve her this week.  Do something nice for her.  Maybe get her coffee or something.  Let me know what you come up with.  Go ahead and look at yourself a little longer sweetie.  I know you can't resist it.  I know it makes you feel good."

There is 2 minute pause while Nancy looks at himself, his face is slightly red.

"I believe you had some homework to complete for this session.  Please present your work."

You asked me to read the book Lady Chatterley's lover and dress like the female character.  Each time I read the book I wore a long nightgown, although I'm sure its wasn't as pretty as the one Connie (the main character, Lady Chatterley) wore.  I didn't think I deserved to dress as a proper English lady.  Although some of the language was difficult, I liked the book.  

I couldn't quite imagine you as Lady Chatterley.  She didn't realize that since she was a woman she had the power to do what she wanted to do.  She was smart and beautiful like you, but you know that you are in charge and can make men do what you want.   She wasn't like that and didn't really know the power she had over a man.

I think of women as being dominant and intellectual and superior to men.  She didn't know she had those advantages so she actually felt guilty about taking an average working man as her lover.  She didn't realize how thrilled a guy like that would be to be able to serve a mistress like Lady Chatterley.  

She made him do lots of things, but she could have made him do a lot more.  He was in thrall of his Lady and would have done anything for her.  Just like I would do anything for you.

I guess I related to Mellor (the lover) the most.  He enjoyed being with her and making her happy.  In the end he had more backbone than I would have though.  He's not as submissive as I am.

My favorite scene was the first time they made love in the woods.  I've never done anything like that.  It would be exciting – the chance of discovery.  I've always liked it when you made me do things in public for that same reason.  The chance to be caught adds an extra excitement.

I liked the book.  Thank you for asking me to read it.  I doubt I would have ever read it on my own.

There is a pause of about 1 minute...subject looks uncomfortable because he doesn't know if he should keep going or not since he doesn't know how much time he has.

"Thank you.  I will consider what you have said.  For your next homework assignment I have something special for you to do.  I have considered your previous request to get a tattoo in my honor and I have decided that I don't find that acceptable.  

I am not obliged to give you a reason, but I will simply say that I cannot promise you that I will always remain your Mistress.  As much as it might give me joy to see you mark yourself as a sign of your enduring submission to me, I will not allow you to do this.  

You also suggested that you would get a piercing for me.  This I have chosen to accept.  For your homework, you will get your ears pierced, a single piercing in each ear for now.  I trust this will not be a problem with your employer, if it is please let me know immediately and I will provide you an alternative.

You will have one week to complete your assignment and send visual evidence of your completion to me.  Do you have anything to say?"

Thank you Mistress.  I look forward to completing this assignment.  Thank you for letting me mark myself as yours.  Every time I see my earrings it will remind me of my submission to you and that it is my duty to serve you and to serve all women.

"Very well.  As I said earlier, your successful completion of prior assignments has earned you the right to remove your chastity device and request permission for an orgasm.  I'm sure you are familiar with the instructions for this, please begin."

Please Mistress, may I have your permission to remove my device?

"Permission is granted to remove your device."

Thank you Mistress for allowing me this freedom. 

Subject remains kneeling, but bows deeply and holds his deep bow for thirty seconds.  Subject then reaches for a key which is off screen and can be seen to remove a small padlock followed by pieces of a chastity device which include locking plates and a plastic tube (the device is CB3000). 

Thank you Mistress my task is complete  (subject returns to a deep bow with hands on top of his head awaiting Mistresses' further instruction which comes about one minute later).

"You may begin your mantra requesting permission to achieve orgasm."

Thank you Mistress.  (Subject adjusts the stance of his kneeling so that he can press his face into the floor with hands extended forward in a position of supplication).

In a loud voice he says: 

You are my Mistress, I am your servant
You are the owner, I am the owned
You are the provider, I am the needy
Your humble servant begs for release

I am weak and unworthy
I do not deserve your attention
I submit to your pleasure
Your humble servant begs for release

I await your permission

This is repeated a total of 9 times.

"I grant you permission to achieve release.  I will stipulate that for this session you may not touch my property with your hand.  You must achieve your orgasm by rubbing against something.  Tell me how you plan to achieve your release."

Mistress, with your permission, I will cum by rubbing my cock against my pretty Mary Jane heels.  May I please cum that way?

"I'm not sure about that idea.  What is your second choice?"

(A little flustered).  Yes Mistress.  Sorry Mistress.  Ummmm, I could remove my panties and bring myself off into them without touching your property - only the panties would touch.  Is that O.K. Mistress?

After a short pause, Nancy looks uneasy.

"The first idea was better.  Please do that.  You may begin at my command and will have no more than five minutes to complete your task."

A pause of 45 seconds

"You may begin."

Subject reaches behind him and pulls off his shoe.  He immediately thrusts his hard cock into the toe of the shiny patent leather Mary Janes and begins thrusting his hips into the shoe, rubbing his cock along the soft leather instep.  From the camera angle it appears that he is fucking the shoe.

After a number of thrusts he pulls his cock out of the shoe and begins furiously sliding the shiny rounded toe of the shoe back and forth across the sensitive underside of his cock, right below the head. 

This lasts for a little more than a minute when he lets out a low moan and cum begins to shoot from his cock.  He collects the first large spurt on the toe of the shoe and then turns to aim his remaining blasts at the inside of the shoe towards the heel.

Subject returns himself to his original kneeling position, head bowed with the shoe placed on the floor in front of him.  His cum is very runny and lends an additional shiny tint to the leather where it has slid down the sides on the front and slid down the instep on the inside to pool in the toe.  

He has cum quite quickly, so he waits silently for over two minutes before mistress speaks again.

"I hope that was satisfying and you didn't cum too quickly.  Its no fun cleaning up after you've had a chance for your libido to cool down and your cum gets all cold and runny.  You know what to do.  Begin."

Yes Mistress.  Thank you mistress for allowing me to cum.  I'm always happy to clean up when you give me permission.  Thank you.

Subject picks up the shoe and begins licking his cum off the toe and side of the shoe.  Where some has slid off onto the floor, he scoops it up with his finger and licks it off.  Once he has the floor and the outside of the shoe completely clean he then tips the shoe backward so that all of the cum that has pooled in the toe again slides back into the heel where he can press his face into the shoe and reach out with his tongue to slurp up every last remaining drop.

When he has finished, he puts the shoe back on his foot and returns to his original kneeling position, hands on his head.

"You may now perform your chastity device cleaning ritual."

(Note, for hygiene reasons this is performed frequently, so subject was fully expecting to be asked to clean his device even if he had not been invited to have a release)

Subject reaches off camera and pulls over a medium sized bowl with soapy water, a washcloth and towel.  He puts all of the pieces of his device into the bowl and then thoroughly washes them and dries them.

He then uses the soapy water and washcloth to thoroughly clean all around his genital area.

He then picks up the pieces of his device and raises them up on the palm of his hand so they are clearly visible on the camera.

"Mistress, it is my honor to return myself to chastity as you have commanded me.  I know that I am weak and that by locking myself in this device I remove temptation to pleasure myself.  Thank you for putting me in your control.  Without this temptation I can focus my energy on how to serve you best.  Thank you Mistress."

He then proceeds to fasten the cuff around the base of his cock and slide the locking plate over top of it.  His member is about half hard as a result of the submission but he is still able to secure the tube over his shaft, join all the pieces together and re-lock the padlock.

With his device securely in place, he returns to his kneeling position, hands at his side.

About two minutes pass with subject in the resting position.

"I hope you have performed your duties diligently and enjoyed the little treat I have allowed you.  I expect you to send your recording in the usual manner.  Please end your session by reciting your "thankfuls".   

Good night Nancy, try not to get too hard thinking about serving me.  It might be a long time before your next release.  You may now use your phone to open the attachment on the e-mail I sent you.  Please look at the photo as you give thanks."

Subject reaches for his phone and quickly finds Mistress' e-mail and attachment.  The photo shows a male who is naked except for a black studded collar, his cock clearly in a chastity cage, kissing the foot of a tall blonde Mistress standing above him dressed completely in black leather from stiletto boots to bustier.  

[The following were written by Nancy and submitted as part of an assignment several months ago.  I liked them so well I incorporated them in subject's daily rituals.]

"Thank you Mistress for allowing me to serve you today."
"Thank you for finding me worthy of your attention"
"Thank you for taking the time to train me to serve you and all women properly"
"Thank you for punishing my weaknesses"
"Thank you for allowing me to wear girly clothes"
"Thank you for keeping me in chastity."
"Thank you for bringing discipline and order to my life"

End recording.



Mistress Chronicles Ch. 05



Background: This story involves my on-line subject Nancy, who I introduced in Mistress Chronicles 4. We've had no in-person relationship. In fact, in all of our sessions Nancy has never actually seen me. I have sent him pictures that I have told him look similar to me, but never an actual photo.  

*

By way of background, Nancy is a computer nerd. Brilliant at working with machines of all kinds, but hopeless with humans. He's early-thirties, slender, but not really physically fit. Scrawny is the word one might use. He admits to having little experience with women and that he has only had actual intercourse one time. 

Apart from female domination, his fetish is lingerie and forced feminization. Through our interactions he has gradually built up a sizeable collection of lingerie which he routinely wears to work under his outer clothes. At his core, he is very submissive and he's been gradually conditioned to accept my increasing authority. 

A subject's orgasm diary

Early on in our on-line relationship Nancy submitted to wearing a chastity device and letting me serve as his key-mistress. As described to some extent in the last story (Mistress Chronicles 4), we have established a ritual he uses when removing and cleaning the device for hygiene purposes. 

Once he was put into the device, his orgasms were only by my permission with the particular terms stipulated by me. This became an element of both reward and control which we both found quite satisfying. Sometimes an orgasm was granted as part of an audio session as described in MC4. Other times I provided him instructions he was to carry out in order to achieve his release. Whatever the case, he had no free choice in his own intimate pleasure.

One of my rules was that he maintained a detailed journal of all of his orgasms which included all the details related to the event. He was required to make a video as well (unless I told him otherwise). The time stamped videos gave me the ability to verify the accuracy of his account and to insure he spent no extra time out of chastity. 

I ordered him to send me the videos on most occasions. Sometimes I asked for them because I wanted to witness his submission and sometimes just as a means of exercising control. Most of my thrill came from being able to make him do whatever I wanted him to, whenever I wanted him to, and knowing he'd obey. 

Very often his descriptions were sufficient. Picturing the scene is frankly often better than the more awkward reality. The control and submission was my buzz, any extra humiliation in the act itself was just a bonus for me.

His journal for his first year in chastity which began on February 1, 2010 follows. I've edited out some of the repetition (such as descriptions of taking his device on and off) but it's mostly his original words, which by requirement were written within 30 minutes of doing what was described. 

Just to be clear, I fully appreciate the fact that keeping a person in chastity 24/7/365 is much more complicated and considerably less, lets say glamorous, than its made to sound. I don't wish to imply that my subject spent every minute of every day inside of his device, although you may chose to read this that way if that's your fetish. The point of the story is the power exchange and my subject's willing surrender of control of his orgasms.

As a reminder, he's performing all of these acts for a person he's never met in person. He's only heard my voice and built a vision in his mind of who he is submitting to.

#1 Friday February 12, 2010. 

It is 12 days since being put in my device. This was my first orgasm since you allowed me to wear a CB3000 so that I would be able to better focus my thoughts on serving you. You allowed me this orgasm as a "Valentines Day gift" for which I am thankful. 

At your command I did my release by jacking myself off with my hand while I looked into the video camera. I was kneeling as I did this and set the camera above me so I had to look up at it, just like I would do if the camera was you. 

While I stroked I thought of what it would be like to be kneeling before you. I imagined that I begged to be allowed to cum. I imagined you dressed in black leather and standing over me. I could hear you telling me to go faster to show how much my submission arouses me. You tell me to prove my devotion by showing I can't hold back when I think of you. 

I was able to bring myself to release in five minutes and twenty five seconds based on the video clock. Thank you mistress for allowing me to cum. I caught all of my cum in my hand and cleaned my hand with a tissue.

#2 Monday February 22, 2010. 

It has been 10 days since I was last allowed to cum. Mistress granted me permission to cum while I had my device off to clean it. My instructions were to remove one of the sissy girl ankle socks I was wearing and put it over my cock so that my balls were in the ankle of the sock and my head was at the toe. 

I stroked myself with the sock on my penis. It felt good and was much smoother than my hand. I thought about what it meant to be a good sissy for my mistress. I imagined that she was right in front of me looking down on me with disgust and laughing at me. It took me 9 minutes and 30 seconds to produce.

I came into the toe of the sock. A little bit seeped out and I wiped that up with my washcloth. I put the sock, still sticky with my cum, back on my foot as ordered. I then finished putting my chastity device back on as I had been taught. It was a little difficult because I could feel my cum on my toes and it was making me hard even though I had just been allowed a release. Thank you mistress for my release.

#3 Thursday, March 4, 2010. 

It has been 10 days since my last release. My instructions were to go to the mall and buy a new pair of panties at a department store. This was very embarrassing since I could tell the lady knew I was buying them for myself. They are yellow nylon granny style briefs, very shiny and very smooth. There is a small bow in the center of the waistband on the front. There is yellow lace all around the leg openings as well. I couldn't resist choosing them. 

As ordered, I put them on in the mall bathroom and threw out my boy briefs. I went to the car and set up my video camera so mistress could see me remove my device. I then used my hand to jerk off my sissy dick into the pretty yellow panties. 

I thought about the lady at the check out stand. She was a little older, but pretty. I thought about her watching me and laughing at me. I spurted in 4 minutes and 10 seconds. Walking around the mall in panties and being embarrassed by the department story lady had made me really aroused. I made sure the video showed the big spot of my cum on the smooth front panel.

Since I know it is important mistress can trust me, I immediately put my device back on and locked it. Thank you for making me buy new panties. I love them. They feel very girly on me especially with my wetspot rubbing against my chastised cock. I feel like a girl with dirty thoughts and a wet spot in my panties. Thank you mistress for my release.

#4 Friday March 26, 2010. 

It has been 22 days since my last release, the longest I have ever been since being in my CB3000. I know I could have been allowed to release 7 days ago, but I failed in a homework assignment. I have edged one time each day, reciting my punishment mantra, during my device cleaning sessions. I am very thankful that I am allowed to cum this time.

I inserted the new butt plug you asked me to buy and wore my favorite sissy bra, panties and ankle sox. As ordered, I wore these while I called my Mom to tell her happy birthday Afterwards, I went to my bedroom and videoed the removal of my device.

While it was off I was allowed to pull my panties up and hump a pillow on my bed. I was in doggie style position with my ass up and my pantied butt facing the camera. While I humped the pillow I wished out loud that I could have been a girl and begged to be allowed to be a sissy and said other things like that until I came into my panties, with the plug still wedged into my butt. Based on the video, I took about seven minutes to cum.

I made sure I said all these things loud so they would be clear on the video. I showed the wet spot on my panties then put my CB3000 back on after cleaning up. Thank you mistress for letting me cum and I'm sorry I failed my prior homework assignment.

#5 Saturday night, April 3. 

It has been 8 days since my last release. I have earned a release 6 days early be agreeing to learn how to eat my cum. I understand that I will be required to do this most of the time from now on. I've read stories about cum eating and it makes me hard inside my tube to think about this.

This session was like my first session. I got my release by jacking myself off with my hand while I looked into the video camera. I was on my knees and set the camera above me so I had to look up at it, just like I would do if mistress was standing over me. 

While I did this I imagined I was kneeling before you. I had been thinking about submitting and getting a release all day and I knew I would shame myself by coming quickly. I begged while I stroked myself. I pictured you all stern and beautiful in a business suit and me naked and small. I went as fast as I could. I couldn't control myself from thinking about you all day and thinking about eating my cum. I came in 3 minutes and 45 seconds.

When I came in my hand, I made sure I licked my fingers and palm clean in full view of the camera. There was a lot of it to suck up, but I took my time to get it all. The taste was ok. I know I need to get used to it. Thank you mistress for my release. Thank you for allowing me to eat my cum.

#6 Sunday April 18. 

It has been 15 days since my last release. I am dressed in a floral dress and have been wearing my butt plug all day like a good girl. I positioned myself on my knees on the bed in front of my camera. I jacked myself into the crotch of my frilliest pink panties. As you had ordered, I imagined that I was a sissy boy getting fucked by my boyfriend. I begged him to fuck me hard and to make me his sissy slut. 

After I came I licked my "boyfriends" cum from the ass of my panties. I then put them back on so I could feel the wet spot on my ass. Thank you mistress for letting me get a release.

#7 Thursday May 6, 2010 

It has been 18 days since my last release. Today is my birthday. Your present to me was to get a release dressed in my frilliest most sissy girl clothes. I dressed in my favorite pink lace bra and panty set. I then put on my frilly white baby doll nightie and white lace sissy ankle sox. I wore these things all night from when I came home from work until I was ready for my present from mistress. 

I positioned the camera and kneeled on the floor in front of it and then took off my CB 3000 like I've been taught. I then used a pair of pink satin panties and started stroking myself. I was so excited, but I tried to go as slow as I could. I wanted to make my special present last. I controlled my strokes and was able to last for 18 minutes and 40 seconds. 

While I stroked I thought about how lucky I was to have a special mistress to control me. How happy I was to be dressed like a sissy and how I wish I could dress like this all the time and how I wished that my mistress could be there to see me all dressed up. Thank you for my Birthday Present mistress. It was my favorite gift.

#8 Tuesday May 18th

It has been 12 days since my last release. This release was like the one I did on April 3rd. I had my bigger plug in my ass and was doggie style on the bed facing the camera. I humped a pillow and pretended it was a man who was doing my ass. I moaned and asked him to do it hard and fill me up and stuff like that.

When I came from rubbing on the pillow I took my small plug and wiped it in my cum. I then licked it all up off the small plug and the pillow and pretended I was sucking the man's cock and he came. I know that good sissies like to eat cum so I was glad you let me get a release this way and let me pretend to serve a man. It made it easier when I imagined the man was your boyfriend and you were making me service him for you.

#9 Thursday May 20th. 

It has only been two days since my last release so I was surprised to get this order on my e-mail first thing when I woke up this morning. I was dressing for work as usual and selected light blue microfiber high-cut briefs to wear under my clothes. As you ordered I took off my device and humped against the side of my bed until I came into my panties. 

I came looking at the picture you sent with my instructions. You said the picture was a girl that looks like you. I love her beautiful blond hair and dominant blue eyes. Her business suit is powerful and confident. I know I would serve this woman anywhere. I came in eight minutes and thirty seconds.

I then put my device back on and went to work with my cum drying in my panties during my commute. I have just got to work and I'm typing this on my phone. My panties are still a little wet and you can see a small wet spot on my pants. I know I'll be chained to my desk while they dry and while I sit here I will be thinking about you and remembering that picture.

#10 Sat June 12

It has been 23 days since my last release. My longest wait ever and so hard because of the picture you sent me. Having a picture in my mind to focus on when I serve you makes it even more of a pleasure, but makes me very frustrated too.

I was listening to your instructions on my iPod and cleaning my device like you had trained me. I was so excited to hear you give me permission to cum before I put it back on. I pictured the girl in the picture as I heard your voice.

As you ordered, I removed the pink lycra ballerina tights I had been wearing. Looking into the camera, I used the tights to jerk myself off. I came in about four minutes into the gusset of the tights. I then begged you on camera for permission to consume my cum from my tights. When I heard your order to do so I did it. 

I then promptly put my device and tights back on. Thank you for letting me cum mistress.

#11 Sun June 27, 2010 

It has been 15 days since my last release. Friday night you sent me a picture of your beautiful vagina. It is an amazingly good picture and I looked at it constantly waiting for today hoping you would let me get a release while looking at it. It is the most wonderful gift you have ever given me. 

I have the picture up on my laptop and have scaled it so it would be life size and I've maximized the resolution. I am staring right at the pink lips spread wide for me. I can see the blond hairs above your clit and you are moist and ready. 

I jerked myself while staring at the screen wishing you were there so I could worship you and give you pleasure. I didn't last long, three minutes and fourty-five seconds. I cum on my hand and the floor. I have to look away from the screen to clean up my mess with my tongue which is what I know you would want.

As I put my device back on I'm sad because I know I will be so frustrated between now and when I'm next allowed a release. I have already imagined a hundred fantasies now that I have two pictures for my imagination. Thank you for this orgasm. I hope I'm worthy for another one soon. Thank you again for the picture. I will write you a separate story, as you requested about worshiping at the altar of your womanhood.

#12 Thursday July 15th. 

It has been 18 days since I've been allowed to cum. (The full story related to this orgasm is in Mistress Chronicles #4). 

I was doing an on-line session with you and you granted me a reward for doing a good job on my homework. I was so happy because the homework was about three ways I would worship your vagina if you were with me. 

You allowed me to masturbate myself using my Mary Janes after repeating a number of begging rituals I have been working on with you. I came in about three minutes and 30 seconds. I was so horny and have been so hard since my last orgasm. Thank you for this release mistress.

MistressM's note -- his begging ritual is as follows:

You are my Mistress, I am your servant

You are the owner, I am the owned

You are the provider, I am the needy

Your humble servant begs for release

I am weak and unworthy

I do not deserve your attention

I submit to your pleasure

Your humble servant begs for release

I await your permission

#13 Thusday August 5, 2010. 

It has been 21 days since my last release. Mistress did a cam session with me and had told me to buy a cupcake to celebrate my six month anniversary of being locked in chastity. 

I was of course kneeling while on cam. Near the end of the session, after I repeated my begging mantra I have memorized, Mistress allowed me to masturbate to release by stroking my cock with my hand. I was directed to aim my cum at my anniversary cupcake and then I was ordered to eat my cupcake along with the extra 'frosting' I had put on it. Thank you mistress for allowing me to cum and thank you for putting me in chastity it has been a great six months serving you.

#14 Saturday August 14, 2010 

It has been 11 days since I had my last release. I bought a bikini as Mistress ordered and spent my day tanning wearing it. At the end of my tanning session, my instructions were to video myself in the mirror showing my tan lines. If I had managed to get tan lines I was allowed to get a release by rubbing myself with the panties part of the bikini while still wearing the bra. If not, I was to be allowed to try again.

Fortunately, I tan pretty quickly and I believe I showed reasonably good tan lines for one day's effort, so I took my reward after reciting my release mantra. As I rubbed myself I thought of how embarrassed I'd be if anyone saw the outline of my bra on my skin or the thin bikini lines on my thigh. It was 8 minutes and 20 seconds before I came into my bikini panties. I consumed my release as I have been taught. Thank you mistress for allowing me a release, I hope you agree about my tan lines.

#15 Monday August 30, 2010. 

It has been 16 days since I was last permitted to cum. I was getting ready for work and for the first time ever I was going to wear a pair women's khaki pants to work instead of my men's pants (as you had assigned me for homework). I was very excited and nervous about doing this although I knew they looked just like my normal chino pants. 

As I was getting ready I received a text from you telling me to get a clean pair of dark black women's trouser socks. As you instructed I removed my device and rolled the sock over my hard cock. I then pulled myself off as quickly as I could until I came into the toe of the sock. It took me five minutes and fifteen seconds. I then put on the cum filled sock and wore it to work that day, as required.

I was afraid to wear both the trouser socks and the pants on the same day so I chickened out on the pants and just wore the socks. I'll do the pants tomorrow. 

I could feel the gooey cum on my toes and the top of my foot. It was slippery between my toes and I almost thought I could hear it squish as I walked. It was very hard to put my CB back on after that since I was already worked up about wearing the pants and now I will be going to work in trouser socks full of cum instead. I couldn't believe I was doing this. I've become so hooked on submitting to you Mistress, you know I'd do anything for you. Thank you for letting me cum. 

#16 Monday September 20th, 2001. 

It has been 21 days since I was allowed to cum. Mistress advised me that I had a seven penalty days added for not wearing the pants to work when I had planned to (see last diary entry). This morning I wore the pants and the socks to work. I came in early and stayed at my desk all day. 




Mistress Chronicles Ch. 06



Background

This story involves my on-line subject Nancy, who I introduced in Mistress Chronicles #4. This subject passed all of the tests I described in "A few good subs", but before we were able to arrange an in-person session, he was offered a job in a town a great distance away, precluding in-person meets.

Nancy is a computer nerd. Brilliant at working with machines of all kinds, but hopeless with humans. He's not terribly self-confident unless he's writing software code, where he feels he's 'among the best.' He's early-thirties, slender, but not really physically fit. Scrawny is the word one might use. He admits to having little experience with women and that he has only had actual intercourse one time. 

Apart from female domination, his fetish is lingerie and forced feminization. Through our interactions he has gradually built up a sizeable collection of lingerie which he routinely wears to work under his outer clothes.

It's interesting to note that in all of our sessions Nancy has never actually seen me. I have sent him pictures that I have told him look similar to me, but never an actual photo. He has a photo of a vagina that I have told him he may assume is mine which he is sometimes asked to stare at and say devotionals to, but it's not mine, just a photo I ripped from the net.

Scenario

By chance, Nancy is scheduled to attend a seminar related to his job which is to be held in the town where I live. Taking advantage of the opportunity, I offered to meet him for his first in person session. I advised him that some of his limits would be tested both before and during the session. He chose to accept the challenge.

He booked us adjoining rooms at the hotel he would be staying at for his conference and provided me the details. Our session would begin at the end of his first day in town. I would contact him at approximately 5pm on that day. Beforehand, he was assigned a number of tasks, which I have asked him to write about.

Nancy's journal

Thank you Mistress for giving me the opportunity to have a session with you, I will never forget it. My story begins about three weeks in advance when I told Mistress of my travel plans and she made me her gracious offer, which I received on Christmas Eve. Her first order was for me to maintain strict chastity for the following 23 days. I would not be allowed to cum for the entire time.

This by itself was a challenge as Mistress continued to demand that I edge myself each night while conducting my chastity device cleaning ritual. Needless to say I began counting the days right from the start. Not only would I have a chance to see my Mistress for the first time, it would be my first chance to earn release.

The second order for me was my personal grooming. I was required to maintain myself completely clean shaven from the neck down at all times under warning that she could demand 'spot check' photos from me at any time. This was a lot of additional effort as the only area I had previously shaved was my legs. I kept this up every day and I welcomed the chance to make myself nice for Mistress.

The third challenge was during the week before my departure, three times I was ordered to wear women's pants to work. I had done so a couple of times before, but never so many times so close together. I was also wearing panties full time and sometimes was ordered to wear quite frilly ones. I was very worried about co-workers seeing my panty lines. 

I did as ordered, being sure to arrive early each day and stay in my cube as much as possible. The third time I wore them, I also wore black women's trouser socks as well. It was so exciting to be completely feminine from the waist down (except shoes) especially with my shaved legs. I could hardly sleep that night. I wanted to cum so badly.

My last challenge related to my flight. Mistress required that I wear panties and black tights under my pants and that my toes were painted hot pink. The clear plastic bag that I sent through the x-ray machine included two lipsticks and the hot pink nail polish in addition to my regular stuff. 

Fortunately mistress had allowed me to remove my chastity tube and send it inside my checked luggage (along with a number of other specified items). Instead she sent me a leather pouch which she made me lace on tightly using rawhide cords with orders not to remove anything until I had checked into my hotel room and received instructions.

I had hoped that she might supervise the removal in person, but didn't think that was too likely as I arrived at nearly 11pm. Instead, when I arrived I had an envelope waiting for me. Inside it was three numbered envelopes, a blindfold and a small padlock. 

The first envelope included my instructions for that night. I was to remove my pouch and re-secure my tube using my normal lock. I was to keep the other padlock open and with me at all times. I was ordered to wear the baby doll nighty I was told to pack when I went to sleep and to open the second envelope the following morning before dressing for my seminar. Naturally I didn't dare touch her property improperly. I had been saving myself for Mistress and didn't want to make any mistakes.

The second envelope specified that I was to wear the white lacy camisole, panties, garterbelt and sheer white hose that I was instructed to buy and bring. This set was part of a 'bridal' collection and was very expensive and frilly. It looked adorable and I couldn't wait to wear it from the moment I bought it. 

I was a little disappointed that my first time wearing it I would have to cover it up. Mistress allowed me to wear socks over my hose. Underneath my regular pants, shirt and sport coat I didn't think it was too noticeable, but I was very afraid of being discovered, you could see the garter tabs through the pants if you were looking for them. I didn't really know anyone, but there were a lot of people at the conference and anything could happen. 

The final envelope I was to open at 4pm. It specified that when I returned to my room I was to strip off only my male clothes. I was to set up my laptop and log into a private chat promptly at 5pm and she provided me the information. She had told me to pack several pairs of earrings and that I should put on the "sissiest" ones that I felt willing to wear in public. I chose my white pearl (not really) earrings.

I'm supposed to stop there, but must add my thanks to my Mistress for making this the greatest experience ever. I'll never, ever forget it.

On-line session

(Nancy has entered the chat)

MistressM (abbreviated as M, following): Hello Nancy. I hope you had a nice day today. I saw you walking around the hotel. I could tell you were enjoying your sexy secret lingerie. Don't worry, I don't think anyone would have noticed the garter tabs and panty lines unless they were really looking.

Nancy (abbreviated as S for Sissy, following): Good evening Mistress. I'm so happy to be here. I can't believe it's finally here. Thank you for doing this. It's hard to believe you are just in the next room.

M: Yes, it is kind of exciting to finally meet. It's been more than a year since we started corresponding.

S: Yes Mistress, the best year ever.

M: You'll probably be pretty disappointed if it turns out that I'm really a 55-year old fat bald guy who gets off on sissy boys.

S: I'm sure that's not true Mistress. I trust the pictures you sent me and I've heard your voice.

M: I guess you'll find out soon enough. First I think we need to make sure you are good and ready. How long since your last release?

S: It has been 23 days Ma'am. Christmas Eve. I haven't had a release yet this year.

M: Maybe you'll be able to earn one tonight. We shall see.

S: Thank you Mistress.

M: We are going to play a game. You may remove your device. Let me know when this is complete.

Pause. S: I've removed my device. Thank you Mistress.

M: So this is the game. Please take your small plug and put it in your mouth. You are not to speak. You will respond only via chat. I'm going to call your room in a minute. Pick up the phone and put it on speaker where you can hear me.

Phone rings, Nancy silently picks up phone and puts it on speaker.

"Good, now you can hear me but not see me. On my command, you will begin stroking yourself to an edge. When you are at the edge, you may type edge, into the chat. When you hear my permission you may stop. If you cum, the session will end. Understand? 

S: Yes Mistress. 

"Begin, Let's see if you can make four minutes" 

(every 30 or 40 seconds I made a comment)

"You look very pretty down there on your knees"

"Isn't the silk of that camisole just wonderful. Caressing your little sissy nipples"

"The stockings are so silky too on your hairless girly legs"

S: Edge

"You may stop. That was about two minutes and thirty seconds. You'll need to do better. Go put on your white training bra. It doesn't really go with your outfit, but a sissy should be wearing a bra and I gave you a break not wearing one all day. Let me know when its on"

Pause, sounds of looking in suitcase. S: I have my bra on and I'm back in position Mistress. I'm sorry for last time. I'll do better.

"Begin."

"Such a little sissy. Sucking cock"

"You'd do anything for your mistress wouldn't you?"

"You'd suck a real cock if I told you to."

"Don't cum sweetie. Don't cum all over your pretty panties. Your're so ready."

S: Edge

"You may stop. You did do better. You made it a little more than three minutes that time. Not too bad. But I'll be surprised if you keep it up. Go ahead and put on your lacy sissy ankle sox and your Mary Janes. I bet your feet have been missing heels today. Let me know when you're ready."

Pause. S: I'm ready Ma'am. Thank you Ma'am.

"Ok. Begin"

"Did they laugh at you at the airport?"

"Did they inspect your makeup bag and ask to see your toes?"

"Did all the pretty business women see your painted toes through your stockings"

S: Edge

"My goodness that was quick. You may stop. I guess Nancy likes all the powerful business women looking at his pretty toes. Did you compare your stockings to theirs and ask them what brands they like? 

Don't get all red faced. That's just what you need is a little makeup. Go put some lipstick on. Do a good job. Pink I think. Tell me when you're done."

Pause, sound of heels on tile as Nancy heads to bathroom. S: "I'm done Ma'am. Thank you."

"Very good. Begin again."

"I bet you look adorable in your lipstick and stockings"

"Maybe we should take you down to the bar and show you around"

"Would you like that? All those geeks and intelligent dominant women, looking at you"

"All frilly in your Mary Janes and bridal lingerie"

S: Edge

"Its not fair me taunting you while you edge is it? You may stop. I know it's been a long time. I think my sissy needs one more thing and I bet you know what it is. Go put on your wig. Make sure its perfect and come back when your're done.

Note: Nancy's wig is a bright pink chin length page-boy cut synthetic wig. Along with her pink lippy, lingerie, ankle sox and Mary Janes it's a very, very sissy look.

S: I'm ready Ma'am. Sorry to keep you waiting.

"Ok then. Once more. Begin."

"What a pretty sissy you are"

"I know you want to cum don't you? You want to cum hearing your Mistress' voice?"

"Such a pretty girl with pink lipstick and pretty hair"

S: Edge

"You can stop. I'm sure you are very hard and very close. Please take the plug out of your mouth and give me your thankfuls."

"Thank you Mistress for allowing me to serve you today."

"Thank you for finding me worthy of your attention"

"Thank you for taking the time to train me to serve you and all women properly"

"Thank you for punishing my weaknesses"

"Thank you for allowing me to wear girly clothes"

"Thank you for keeping me in chastity."

"Thank you for bringing discipline and order to my life"

"Very good Nancy. Now listen carefully because I'm going to hang up the phone after I give these instructions. You're to go over to the connecting door and open your side of it. I want you to kneel just beyond the doorway. I may need to get around you into your room. Stay dressed just as you are in your pretty sissy clothes. I want to take some pictures, so have your knees wide apart and your head up. Oh, and put the blindfold on. Make sure it is quite secure. If I think you can see out, the session will end. Got it?

"Yes Ma'am"

Mistress hangs up the phone.

Transcript of in-person session, from my video camera

I made him wait in that position for about 20 minutes while I got myself ready. I'm sure he was getting nervous that I had stood him up.

Although he couldn't see me I was wearing a satin black bra, a matching garter belt and smoke black seamed nylons along with four inch stiletto heeled shiny black leather boots. My make-up was normal evening make up with slightly smoky eyes and dark red lipstick. I wore my just beyond shoulder length blonde hair down.

Opening the door I began by taking a couple of pictures of him as I wordlessly walked all the way around him and then back into my room. He was there on his knees, just as he was ordered in his pink wig and lipstick, pretty satin and lace lingerie and his innocent Mary Janes and ankle sox. He shuddered a bit as I went by. So close, yet still so far.

Setting down my camera I walked right up to him so that my bare already moist slot was just about six inches from his nose. 

"So Nancy. Do you feel my presence? Can you smell my arousal and feel my dominance wash over you?"

"Yes Ma'am. I can't believe we're together"

"You're just as pathetic in person as you are on video cam. You are truly a sissy. No real man would dress like that. No real man would obey orders from a woman he's never even seen. You jerked off to a picture of my pussy. Would you like to smell the real thing? Go ahead its just inches away. Take a deep breath and let my scent into you.

Deep breath. "Thank you Mistress. You smell amazing"

"It's nice of you to say so Nancy. Do you think that's just my scent? Do you think maybe I let a real man satisfy me first and maybe some of his spunk is in there too? 

Why don't you lean forward and kiss my boots while you think about that. Very gently, I don't want pink lippy stains on them."

Nancy leans forward and I position the toe of my boot beneath him as he plants a light kiss on the toe. "Thank you Ma'am."

"Look how hard you are from smelling me and kissing my boot. Why you must be a whole five inches. I'm sure that's as hard as you get isn't it sissy? Here let me rub the toe of my boot against that little sissy clit I see in those pretty shiny panties.....careful now, I'm going to rub up and down and you don't want that cock to spurt."

"Pllleease Mistress. Please. I, I, please stop. I'm so close."

"You want to cum don't you? You want to cum right now? Without even seeing me?"

"Yes, I mean no. I want to cum Ma'am, but I want to see you too."

"Well why don't you go ahead and ask permission and we'll see what happens"

"You are my Mistress, I am your servant

You are the owner, I am the owned

You are the provider, I am the needy

Your humble servant begs for release

I am weak and unworthy

I do not deserve your attention

I submit to your pleasure

Your humble servant begs for release

I await your permission"

"Say it again sweetie. I love hearing you beg. Begging it's what you do best."

(He repeats it as above)

"Very nice Nancy. Your weakness is really arousing to me. I think I'm going to lie down here on the floor in front of you and give myself a little relief while you slowly beg permission from me again. I love watching you beg. It makes me so hot when you give all your power to me."

Pulling out a vibrator I begin working on my sodden pussy. I rub my nipples through my bra and slide them in and out alternating with the vibe while I hear him repeat his chant. As I attended to myself his begging mixed with the sound of my own pleasure.

"You are my Mistress, I am your servant"

"Mmmm ohhh yesss"

"You are the owner, I am the owned"

"Ohhh that's it ohhh, ohhhh"

"You are the provider, I am the needy"

"Ohhh, yess, you're such as sissy, so submissive"

"Your humble servant begs for release"

"Mmmm, this feels so good"

"I am weak and unworthy"

"Smell my arousal, breathe my scent"

"I do not deserve your attention"

"Beg for it, beg for me"

"I submit to your pleasure"

"Mmmm so close, so close"

Your humble servant begs for release

"Unh, unh, unh"

"I await your permission"

"YES, YES Ohhh Yes I'm cumming, ohh yes so good"

I laid panting on the floor in front of him as he continued. I could see some pre-cum had leaked into his panties, which was entirely understandable. When I recovered I stood back up and again stood near so he could feel the heat from my body along with my musky, moist, post orgasmic aroma.

"That was so good. Here, smell."

I take a finger full of my juices and wipe them between his nose and lips. 

"You'll be able to smell that all night. You beg so nice. You deserve some type of reward and I'm going to let you make a choice about that. Are you ready for a choice Nancy?"

"Yes Ma'am. Thank you Ma'am. I couldn't see it, but it was very erotic to be near you while you did that -- got off I mean"

"Yes. Well. Here's your chance to get an orgasm for yourself. You may have one right now, with your blindfold on. I'll rub you with my boot some more and you can cum right into your panties. How does that sound?"

"It sounds ok Mistress. Thank you."

"Or. Or. I told you there was a choice. The other choice is you can beg me to put your device back on and then I'll let you take your blindfold off and you may see me. I'll give you one minute to decide."

"I don't need a minute Ma'am. I want to see you so bad. I'll choose the second one. Please put my CB back on me Ma'am. The parts are on the desk. Please put it on me and let me see you."

"As you wish Nancy. I thought that it would be a more difficult choice for you. But I'm rather pleased with your decision. Hands on your head please."

I go into his room and get his device. Ordering him to stand and lower his panties, I give his balls a hard squeeze and with some help from some ice from my ice bucket I make his cock shrink and in a minute or two have him locked back into his cage. 

I could feel his body tremble several times as I handled him - trapped between his natural arousal and physical need and his desire to fulfill his orders.

"So this is how it will be. You stay kneeling right there. I'm going to go back into my room and close the door. You will stay there until you hear your room phone ring. When you do, look at your e-mail and follow the instructions. Clear?"

"Ye-yes Ma'am"

"Don't worry Nancy. I can hear the fear in your voice. You must trust me. I won't cheat you. You've done a good job"

"Thank you Ma'am"

I close the door and back in my room throw on a little black dress and some dry panties. I clean myself up a bit and then exit my room and go down to the lobby of the hotel. From the lobby phone I dial his room, let it ring one time and then press send on an e-mail I had prepared.

The e-mail Nancy received said "Your mistress is the one in the bar with these boots. You have 10 minutes to find her." Attached was a photo of just my boots.

About five minutes later I saw him come into the bar of the hotel, which was really a massive sprawling lounge with several little areas divided by partial walls. I was sitting up at the bar, but on the far side of it such that the only way he could really see my boots was to come all the way around the bar and wander into what was both a dead space and the place where the waitresses came to place bar orders.




Mistress Chronicles Ch. 06



I could tell that he had really just thrown a shirt and pants over his whole outfit and had barely taken the time to wipe the lipstick off his mouth. He was still wearing his pearl earrings. Since I knew to look for it, I could see where his bra and camisole puffed up against his shirt.

It was rather comical watching him wander through the lounge with his head down looking under tables to try to spot a woman with boots. At one point a waitress asked if he needed a table and he nervously mumbled something at her and kept up his somewhat flustered pursuit.

After circling most of the room, which had a fair mix of men in women in it as there were a number of events going on in the hotel that evening, he finally spotted me. He must have sensed that I was possibly the right one because he only made cursory glances at other women's footwear as he made his way towards me.

When he finally arrived and saw that I sported the correct footwear he asked, "Miss M?"

"Yes, Nancy I am your Mistress"

"I can't believe it. You're so beautiful. You're the best looking woman in the place. Thank you Ma'am. Thank you for seeing me, for everything. I can't believe it...."

"Relax, have a seat. Let me get you a drink. A glass of wine maybe?"

"Yes, that would be fine, thank you. Thank you Ma'am."

I arranged for his drink and we chatted quietly. 

I teased him a little about not changing his earrings and that I could see his bra through his shirt. While my comments caused him to get a little red faced, the fact was he remained in awed silence of the fact that he was at long last sitting in the presence of his Mistress. It was like a little kid meeting Santa for the first time -- fear, excitement, wonder, hope all rolled into one.

As I described in the introduction, Nancy isn't all that comfortable around people. It would be generous to say that we had a conversation. More accurately I asked him some questions and he tried to assemble short coherent sentences in response. We continued like this until our glasses were nearly empty and by now the bar area was getting a little crowded.

"So Nancy, you've done a good job and it seems only fair for you to get a reward. Would you like to go back to your room now?"

"Yes Ma'am. Thank you."

Leaning in close to him so only he could hear, "So here is what you will do. I'm going to drop my napkin on the floor. You will get off your bar stool and pick-up my napkin. While you are down there you will kiss the heel and toe of my right boot. You will stand, bow to me and head up to your room where I will find you in the exact position I left you. I mean exact, every detail the same. Nod if you understand me?"

He nodded his understanding and then did as I ordered. I stayed for another drink and was getting moist imagining him kneeling there, blindfolded in his room awaiting my return. I knew he'd wait all night if I wanted to do that. His level of submission was the farthest I had ever taken anyone and it frankly excited me, although I did have some doubts about how much farther I was interested in going.

Heading back to my room I took off my dress and changed my bra for a black bustier. I pulled my hair back and refreshed my makeup to give myself the classic dominatrix look. I was still wearing my black panties, garter belt, black seamed nylons, and 4 inch stiletto heeled boots.

When I was ready, I quietly opened the pass door and found him just as I had left him. He had put his pink wig and pink lipstick back on and was kneeling right where he had been before. His chastised cock was bulging out his white satin panties which matched his camisole and bra. He had put his Mary Janes back on along with lacy ankle sox and the white stockings and garters he had been wearing all day.

Even though he was blindfolded, I knew he could sense my presence. His back was straight and head bowed in perfect submissive position.

Wordlessly I moved close to him and ran the toe of my boot over his trapped member. He was as hard as he could be inside his device and I knew it was probably a bit painful for him.

"Very good little one, you follow instructions well. I'm sure all of the lovely ladies at the bar are giggling among themselves at the guy who was roaming around the lounge checking out women's shoes and wearing a bra. Did you like that Nancy? Could you feel all the pretty women looking at you?"

"Yes Ma'am. It was worth it. It was worth it to see you."

"That's very nice of you to say. Did you like kissing my boots at the bar? I'm pretty sure that red-head in the strapless dress noticed. She smiled at me when you stood up."

"Yes Ma'am. I liked that too. I'd kiss them again now if you'd let me."

"That's fine Nancy you may kiss them. Worship them with your mouth and tongue. Just lean forward and put your face near the floor and I'll make sure my boots are right there for you to adore."

With that Nancy began planting kisses all over my shiny black leather boots, leaving traces of her cheap pink lipstick in the process. Pointing this out, he quickly switched to kissing and then licking my boots, cleaning up most of his mess in the process. 

I let him continue for several minutes as his unbridled submissiveness continued to stir my juices. Soon he was kissing and licking my heels. As he started working his way up my boot I stopped him and asked him to get back into his kneeling position.

"That was very nice. You did a pretty good job being blindfolded and all. While I'm sure you would have continued all night, I expect you'd like to achieve release. Am I right?"

"Yes Ma'am, if it pleases you I would enjoy a release. My cock is aching inside its tube. Every time I think of you it just throbs."

"So here's another choice. You may take your blindfold off and I'll allow you to masturbate yourself and cum in your panties or you can leave your blindfold on and I'll give you a hand job myself. Which would you prefer for your release."

"Ohhh definitely blindfold off Mistress. I want to be able to see my beautiful mistress. I know I will cum so fast."

I step forward and remove his blindfold my panty covered crotch is just inches away from his face which remained downturned. "You may begin stroking yourself on my command. You will meet my eyes and not look at my panties or crotch while you do so. Beg me when you get close to cumming. You may not cum without my command."

"Yes Ma'am."

I told him to stand and quickly removed his CB-3000 setting it aside. His cock immediately sprung to its full length and looked quite angry and purple from its confinement. I made little eye contact as I did this but could tell by the way his body relaxed that he must have been enduring more than a mild bit of discomfort. 

There was no doubt in my mind he'd cum quickly, but I'd see what I could do to draw it out at least a little. I returned him to his kneeling position and resumed my position inches away from him so he'd need to crane his neck back to meet my eye.

"Begin."

He did a fairly good job of holding my gaze which must have been difficult as I teased my tongue across my lips and did my best to look as wanton and sexual as possible. The fact was, our scene was arousing and though I had a nice orgasm earlier I could feel another one building. 

I could see him trying to hold back although his hand moved at a reasonable pace up and down the smooth satin front of his panties. I could see the lust in his eyes, but also some fear. He wanted to cum badly but feared cumming too quickly wanting to prolong his moment as long as he could.

"Please mistress. Please may I cum."

"No. Stop right now"

The surprised and then frustrated look he gave me was priceless. Only his good training enabled him remove his hand and not squirt into his panties anyway -- he was that close. As it was there were some streaks of precum that I chose to ignore.

"That was close wasn't it Nancy. You almost came without permission didn't you?"

"Yyy-eess Ma'am. I was very close. Ummm sorry Ma'am."

"No, don't be sorry. You may stare at the floor until your sorry little unit goes soft. I thought it would be nice to prolong the moment a bit. Just to make it special you know. You've worked quite hard to get here and who knows when we might get together again."

"Thank you Ma'am. I do want it to be special."

It took several minutes for him to finally get at least a little limp and I took a seat out of his line of sight for a few minutes to help him. Getting back up I gingerly removed my panties allowing him, once again, the sight of my bare and moist slot.

"Look up and stare at my pussy Nancy. This is what controls you. This is what you submit to. I bet you'd like to kiss it wouldn't you?"

"Ohh yes Ma'am. I'd love to. I've dreamed about it."

He was already back at full hardness by the time I was close to him. I pulled the waistband of my tiny panties down over his head and positioned the moist gusset over his nose.

"Well you won't be able to kiss the actual thing, but you may kiss the crotch of my panties. Panties which have been rubbing against me all evening, absorbing my scent and juices all night.

Go ahead and kiss the crotch of my panties and jack yourself again. Don't forget to ask permission before you cum. Begin."

"Yes Ma'am. Thank you, thank you"

He immediately began wanking his cock, inhaling my scent and kissing my panties. 

In less than a minute he was begging, "Ohhh nooo, please Mistress, Please ohh god, I'm, please may I....."

I knew he was beyond control so I said "Yes. Cum my little sissy. Fill your pretty panties with your sissy seed. Cum as hard as you can while sniffing my panties."

He jerked and twitched several times as he pumped out load after load into his panties. His panting breath and assorted guttural noises made it clear that this was a release of epic proportions and he was holding his breath and doing every thing he could to ride his orgasm as long as possible.

I rubbed my breasts as I watched his display and felt some sparks of my own at his submission. I resisted the urge to touch myself right then as I wanted to finish the scene. 

He was limp as a rag doll in front of me as his breathing came back under control. Taking advantage of his weakness I continued, "You know what you need to do. Remove those panties and clean up your release. Sissies love eating their cum and I'm sure you want to show your mistress how much you like yours."

"Yes Ma'am. Thank you Ma'am. I've never cum so hard or so much. Thank you."

It took him a second or two to figure out how to get his panties off while kneeling, but he managed it. Turning the panties inside out so he could get at the cum, he stuck the dripping front panel into his mouth through the leg hole of my panties which were still on his head with the gusset at his nose. He began sucking the cum out of his panties while alternately taking in deep lungfuls of my panty's moist aroma.

Watching this act of submission was all I needed. Leaning against the doorframe I stuck three fingers into my steaming slot and quickly began fingering my clit. 

Nancy couldn't figure out where to focus on me, on the panties in his mouth or the panties at his nose. Despite having just released, he was hard again.

In no time at all I had found my spot and was nearing an orgasm of my own. I started moaning and then swearing, "Oh fuck, ohhh fuck yes, mmm so fucking good. Ohh, ohhh, ohhhh"

Once again the waves crashed over me and I went down to my knees to maintain my balance and ride out each jolt. I knew he was watching the whole thing and the intimacy of our shared releases was remarkably satisfying. 

We had both given each other what we wanted and were very satisfied by our respective roles. It was a new high point for my career as a dominant mistress.

Regaining my composure I stood back up and moved myself back to my spot directly in front of him.

"Well I hope you enjoyed that. You've quite pleased me this evening. You may stop sucking on your panties for the time being. You may clean them up the rest of the way after I leave."

"Yes Ma'am. Thank you. I'm glad this evening gave you pleasure. I'm so happy to have pleased you."

"You did Nancy. Thank you. Now go ahead and get your device back on. I have some ice in this bucket if you need it."

"Yes Ma'am. I wish you could stay."

"I'm sure you would like that Nancy, but it's probably best for us to stop right here. It's been a beautiful evening, don't ruin it by making me punish you."

"Sorry Mistress. I'll put my device on now."

He struggled a bit to get it on, but didn't ask for any ice. When he was finished, I continued.

"You may remove your device before you pass through security for your flight home, but you will put it in your carry-on bag. I will trust you to not touch my property during that time. After you pass through security, find a men's room and put it back on using the new lock I provided you. I shall mail you the key when I think you need it. You can keep my panties as a souvenir. I expect you'll keep them in a place of honor and treat them royally."

"Yes Mistress, thank you Mistress."

"I'll contact you as normal for assignments. Good bye Nancy, it was nice to have finally seen you in person."

"Thank you Mistress. This was so special for me, I'll never forget it. May I please kiss your boots one last time to say good bye."

"You may"

He leaned forward and reverently kissed each boot and as he sat back up I could see his eyes clouding up as though he was about to cry. I gave him a smile and then closed the pass door, quickly gathered my things and quietly left the room and the building. His desperate look and willing submission lingered with me however and was the source of several good orgasms that night and for weeks beyond.

Post script:

As it happened that was the one and only time I ever saw Nancy. We continued our on-line interactions for a couple of more months before he asked if we could stop. He said that the sessions had lost some of their edge for him once he had finally met me and he couldn't imagine that memory would ever be exceeded. I had to admit that there was some indefinable edge that had come out of our interactions and I was a little uncertain myself as to how to get it back.

We parted with a final live webcam session where I let him see me one final time and he was allowed to release into the panties I had given him. I've not heard from him since. If he reads this and recognizes himself (as he no doubt would) hopefully he will get back in touch with me and tell me how he is doing.