Mistress Chronicles Ch. 05

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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.

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.

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 antalya escort 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.

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.

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.

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.

Sunday April 18.

It has been 15 days since my last release. I am dressed in a floral dress and have been wearing serik escort 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.

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.

0 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.

1 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 side escort 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.

2 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 ).

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

3 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.

4 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.

5 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.

6 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.

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