Mistress Chronicles Ch. 06



This story involves my on-line subject Nancy, who I introduced in Mistress Chronicles . 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.


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 Escort Bayan 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.


“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 Bayan Escort 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 Escort 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.

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