Mistress Chronicles Ch. 05

I was so afraid to be wearing both women's socks and pants. I just knew one of the admin girls would notice it and then everyone in the company would know. The one girl, Stephanie, looks at me like she knows what I'm up to. She's young but not very pretty, and sorta overweight. But I'll admit I had a fantasy all day long thinking about her confronting me over my pants and socks. I imagined that I begged to eat her out and be her pussy slave if she wouldn't tell.

Mistress said if I wore both things I would be allowed to get a release and I did. I took pictures of myself every hour to prove it. I jerked myself off with my hand into a pair of panties and thought about mistress and my Stephanie fantasy from earlier. It took six minutes even. Thank you Mistress for letting me earn my release. I'm sorry that I chickened out last time and I've learned my lesson.

#17 Friday Oct 1, 2010.

It has been 12 days since I had my last orgasm. Mistress told me to buy a pair of long dangly earrings to wear in my recently pierced ears. She also told be to buy a bunch of cheap metal bracelets from the dollar store.

For my release I was to stand in front of the camera wearing nothing but my garter and stockings and my high heel Mary Janes the earrings and the bracelets on my right hand. I was to repeat my orgasm permission mantra and then stroke myself for one minute without cumming. After I repeated my mantra the ninth time I was required to cum in the following minute. If I didn't cum, the chance was over.

I did as I was instructed. Each time the jangle of my bracelets and the swaying of my long dangly earrings became more arousing as I pulled on my poor cock and tried not to cum. For some reason it was very humiliating to be see my earrings dangle and hear my bracelets clatter as I did my task. After the ninth repeat I came in about thirty seconds. I was just barely hanging on by the time I got that far. Thank you Mistress (again) for letting me get a piercing for you and thank you for my release.

#18 Wednesday October 20, 2010.

It has been 18 days since my last release. This release is part of a homework assignment. My assignment is to wear at least five items of women's clothing and to find a place where I can safely give myself a release in a public place.

I chose to wear a white training bra and a camisole under my shirt. I also wore panties, black opaque tights and my women's khaki pants. Those are my five items.

I drove to a small park where there were recreation fields. It was late at night, about 11 o'clock so there was no one around. I was really nervous, but I had been getting hard all day thinking about how humiliated I'd be if I was caught and how exciting it was to submit to my mistress that I was already very aroused when I got there.

I removed my device in the car and filmed that, as usual. Mistress said I didn't have to film the public part. I got out of the car and went behind the concession stand towards the woods. I then whispered my orgasm mantra and pulled on my cock. I had brought an extra pair of panties to cum into, which I did. I couldn't really see the time, but I think it was less than five minutes.

After I came I hurried back to the car and filmed myself sucking the cum off the panties and putting my device back on. I then came home and posted this entry to my diary. Thank you mistress for allowing me to earn an orgasm for my homework.

#19 Sunday October 31 at midnight.

It has been 12 days since my last release. My instructions were to be dressed up as a girl of some kind from the time I got home until I went to work the next day and that included while I was giving out tricks and treats at my house. For tricks and treats I dressed like a witch. I wore a floor length black witch's dress and a pointy hat and used green face paint and wore a scraggly black wig. Underneath I had on black panties, black stockings and a black camisole, but no one could see that.

After the children stopped coming to the door. I added a black bra that I stuffed to give myself breasts and put on bright red lipstick. I also put on my black Mary Jane heels. I turned out all the lights in my house and carried a candle as I prepared myself.

You said I could have a release at the stroke of midnight. I downloaded a bunch of transvestite porn stories about magical transformations and read these thinking about being changed into a girl while I waited for midnight to be close.

I then went into the bedroom and set up my camera and tested some lighting so I could film my midnight release. At 13 minutes before midnight I removed my chastity device and repeated my begging for release mantra. I then stroked myself. I imagined a story that an evil spell had turned me into an ugly witch and that the only way I could be changed into something else was to cum at the stroke of midnight. If I came right on time, I'd become a beautiful girl. If I was early, I'd remain a witch. If I was late I'd be just be a sissy man again.

While I stroked I repeated the magic spell "Please transform me, make me a girl." I timed it so I came into my hand right at midnight, but I must have been a little off since I didn't transform into a girl. I'm still your sissy boy. Thank you for my Halloween release Mistress. I hope you enjoyed the scene I created.

#20 Wednesday, December 1, at 12:01 am.

It has been 30 days since my last release. You challenged me to make it a whole month without release and though it has been extremely difficult, I have made it. Thank you for putting me to this test.

You said I could come in a way that pleased me if I was able to do it, so here is what I did. I took the picture of you vagina that you sent me and I printed off a paper copy of it. I did it at work late at night when no one was around using the very high resolution color printer in the graphics room (I hid the picture in the middle of a power point deck so no one would be suspicious at the filename).

I started early and made myself ready like the best sissy I could be. I wore pink bra and panties, ankle sox and my Mary Janes. I also put on pink lipstick I bought special for the night and a pretty while lace cami top. I stuck my big plug in my butt since good sissies love to be filled.

When it got close to midnight I started repeating my begging to cum mantra. I put the picture that you said looked like you next to the camera so I could look into "your" eyes when I was saying my mantra. After I did 10 times I started stroking myself lightly and kept saying it. When it was midnight and my month was up, I kept saying it as best as I could and stroked as hard as I could and came in about one minute after midnight.

I shot my cum all over the picture of your vagina I had made and imagined you had let me cum on your pussy as a reward for one months chastity. I then licked up my cum from the picture wishing it was for real. Thank you for my orgasm Mistress.

#21 Friday December 10, 2010

It has been only 9 days since my last release. I did a good job on my last homework assignment and Mistress allowed me an early release during my video-camera session (a session like the one in Mistress Chronicles #7).

I did the various tasks required of me during the session and then recited my orgasm permission mantra. I love to repeat my mantra, it reminds me of my place as Mistress' servant. After that I removed my white sissy ankle socks with the ruffled edges on them and slipped them over my hands like mittens. I then put on the pink lipstick.

I then stroked myself slowly as you ordered. I was required to make it last for ten minutes since it was December 10th (glad I was allowed an early release!). I had a small plastic cup I was required to shoot my release into and I did just a few seconds past the ten minute mark. Mistress ordered me to cover the cup with plastic wrap and put the contents into the freezer to be used at some future time, which I did. Thank you Mistress for allowing me an early release. It was very satisfying and was also very satisfying to know that I have been serving you well.

#22 Friday December 24, 2010.

It is Christmas eve and it has been 14 days since my last release. I was supposed to travel to visit my family on Christmas day so Mistress said I could open my present from her on Christmas eve. I was out with friends earlier and after getting myself done-up, I've been listening to Christmas music and opening cards and gifts that some relatives have sent me.

I'm wearing my favorite pink panties and bra. I also have on white cotton ribbed tights. I'm wearing a long fleecy night gown with lace all down the front and at the sleeves. I feel warm and comfortable even though I am alone.

I saved Mistress' gift for last it was a small square box with a pretty red ribbon on top. The tag said To: Sissy Nancy From: Mistress. This alone made me stir inside my chastity.

Opening the box there were three things inside two small wrapped items and a card. The order was marked so I followed the instructions. The first wrapped item was a key chain that had Nancy spelled out in gold letters. The second was an ankle bracelet with a metallic heart charm on it that said "Property of Mistress M."

The best gift was the card which said in Mistress' own handwriting "The key chain is for the lock on your device. While I am your key Mistress, you can at least have a key chain. The ankle bracelet will be worn daily subject to my orders. You will wear it on Christmas day under your regular socks."

The best gift of all was the last three sentences. "Yes, I am free to meet you when you are in town on January 17th and 18th. You may give yourself a release by hand and then return to chastity until we meet. Merry Christmas.

I was so excited that I'd finally get to see my mistress I immediately got my camera set up and then right there in front of the tree, put on my ankle bracelet, put my lock key on my key chain, repeated my permission mantra and then jerked my self by hand saying "Thank you Mistress" over and over again until I came, which happened in four minutes and fifteen seconds. Thank you Mistress. Seeing you will be my best gift ever.

#23 Monday -- January 17, 2011. The story that goes with this release will be presented in Mistress Chronicles #6.