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October 2018
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Governess Spanking Roleplay

Governess Spanking Not To Be Forgotten

A great week it was for Governess spanking, Governess sissy trainer, Governess phone fantasy roleplay. Now the phrase coming out of the woodwork may be appropriate. The most fun was “Larry” who read my bio from Spankedbyphone. What resonated was within the writing of giving him the spanking of his life . Certain phrases resonate with many such as “I’ll give you something to cry about”. These are triggers which spark that kink fuse.

Governess Spanking Roleplay: Mistress Cassandra 1-800-730-7164

Governess Roleplay

I’ve written a great deal about my favorite role play which is Governess spanking, and caning of course. Why do I like it? Not only is it corporal discipline, but often clothes make the Mistress. For me anyways. Wearing the white high buttoned shirt excites me more than low cut cleavage. I do not have large breasts and I never cared if I did. If I thought they were important, I would have had big tits built. The brain makes the girl, not the breasts. For me, Governess play is a high form of intelligent role play.

Tight Black Pencil Skirts And Black Boots

A true Governess does not wear kinky clothes. She is mostly in conservative attire, keeping a tight ship. Gone are the days of knickers and grab your ankles for the cane. The Governess has her place in the BDSM world of tight fitting pencil skirts and boots to the knee. In her toybox are crops, canes, and of course opera length leather gloves made for Governess spanking.

Over My Knee For The Spanking Of Your Life

Needless to say, more like Larry must reach my listing and phone domination. More must get over my knee for the spanking of their lives. More must kiss my boots and taste the crop. More must be on there knees uttering the words “yes Governess”

Mistress Cassandra 1-800-730-7164
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Sissy Loves Halloween Erotic Audio

A Halloween erotic audio was suggested by a little sissy slut who fancies the thought of being a little brothel slut. She does not have to try very hard.


Hello sissy sluts. You have been looking forward to this all year, but tell me why are the same costumes showcased? Brothel sluts? Certainly you have this on your mind. What type of clientele will you have on a night like this? This old west saloon hotel was rented for you in mind. Don’t be surprised if you find skeletons in the closets and ghosts under the bed. What sissy looks forward to tonight could be an outlaw packing a ten inch dick. Maybe several of them taking a sissy or two hostage, abducted, thrown in the trunk and swept away to a haunted castle.

Imagine that little captivity gurl all dressed as a saloon girl ready for her next appointment. Instead she is swept away with sissy friends and made into a real slave used for one thing only. A little cocksucker but happy about being the damsel in distress. A spooky castle in the dungeon with straw beds all ready. Consider yourselves fortunate. You could be sitting at home eating candy and bored. Dick is the candy you crave.

You are surprised to be put on stage and auctioned off while tied up to a pole. Get down to your knees, it’s actually a contest of who does the best sissy slut , the best blow job, and the best spit roast queen. Relieved you are that this is what it is and not full on real captivity with a muscular outlaw with a ten inch dick. Are you disappointed sissy petunia? Was that the prize you wanted. Of course you are not. Imagine if we changed the theme and you were that damsel in distress with a knight in shining armor! Right, I thought so. You want to be the Princess.

Mistress Cassandra 1-800-730-7164



Mind Fucked Got His Wish

Mind Fucked Winner

That’s his name. Mind fucked. MFA for short. He’s a real winner. I know just about everything about this boy. He is always looking to go a step further. To get this humiliation slut on Skype was a huge endeavor. I did mention MFA a few blog posts back. I mentioned how Skype has a camera function that has an audible click. There is a photo gallery included and if you do some right clicking the pix can be saved to your hard drive. Imagine what a mind fuck and a surprise to check your email to find pictures of you sucking a big dildo with a wig on, a cum jar labeled as such, and a fish net body stocking. Ohhhhh I am soooooo wanting to post these photos right here, right now, on this blog. Too bad I cannot! Then he would be absolutely mind fucked.

Mind Fucked Got His Wish: Mistress Cassandra 1-800-730-7164

Slap That Face!

Making him slap his face with his dipped in cum dildo is a sight to behold. On Skype it’s one big blur. Several times he did not wear a mask. One was a baldy view and another was a long blond platinum wig in my honor. Sorry MFA, but emulating me, trying to look like me will not work. You are a unique piece of work. With that, as you read this, slap that face with that dildo and accept orgasm denial as your daily cup o’ tea.

The Humiliation Wish List

The other night, he finally got his other Mistress on the call. This was on his to do list and he finally got his wish. We put all of our information together on MFA and pieced it together. There will be more calls with Mistress X, pictures exchanged and info of the mind fucked importance. Three way Skyping with much laughter and humiliation. Get ready for the next MFA, you have more coming your way!

Mistress Cassandra 1-800-730-7164
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Intermediate Chastity Erotic Audio 4

Intermediate chastity discussion is up next in this erotic audio series. Once you get to this program you have advanced to my liking, and I expect you to succeed. Give a listen to this intermediate chastity audio and comment.


Now that you have gotten your feet wet with chastity lite, you’re all puffed up with pride knowing you made it past the third day. Your cock got swollen in the cage and you had no other assignment except to stay in chastity. Your pictures were sent daily with the lock intact and there was no cheating. Not even an eraser head touched that cock because you were determined to please me. I unwrapped you like a present and there it is, the triumphant cock. You did it. You started with a week of tease and denial and the last edge ended in lockup. The reward comes now of blasting an orgasm after ten long days. It was frustrating but you did it.

Now it’s time for intermediate training, and you can do it. I don’t care if you play the sissy card. Plenty of sissies have endured, and so will you. In intermediate chastity training, there will be no whining, no begging, and hopefully no disappearing. If you fail and disappear you are allowed back, but many do not due to the frail male ego. Drop it, lose it, and man up! This is chastity intermediate and it’s boot camp.

So what I do is start you right away. No vacation for good behavior. By now you should have a variety of cock cages or some on the way. You are writing affirmations of your place in my chastity world, you may have started a blog which is expected to be creative and descriptive. You may be technically talented and have made a website such as the playground. You may be a sissy doing the assignment rounds as all sissies do except your cage is pink and you are locked.

At this point you will also do research on cages I have interest in. Even though you have not worn a particular cage, you can research it for your future cage. After all, before a woman or sissy buys a dress, she will read reviews, knows the fabric, how the size runs. If you have no interest in that, I will begin to wonder if you belong in a chastity program at all. I will begin to wonder if you are easily bored which means you will be a whole lot of work. You should be always willing to please at this point. All things are communicated, and passive aggressive behavior is not tolerated.

You will have a new sentence. I like three weeks for the next challenge. We discuss lock boxes and online key holder backup plans. The plastic numbered locks are efficient. I laugh when I hear crazy glue the lock. Absolutely not. With affirmations, you now should have a chastity mindset, the mindset to desire being a locked slave.

In between the sentence there will be several tease and denial sessions which may include a pass the penis program with several tease Mistresses. This program keeps you in chastity, it must be planned that you will be locked for the whole three weeks. These are the basics, and so much more will be included depending who you are and what you need.

The next recording and post will be the advanced chastity training, extended times and maybe a permanent device requiring a piercing. See you next time!

Mistress Cassandra 1-800-730-7164


Under Sissie’s Dress Erotic Audio

What should be under sissie’s dress? Panties, slips, bras, corsets, garters, etc… But what SHOULD be under that dress most importantly to make her curvy and feminine? Sissy must think man bait, she must think expert cocksucker. Like a real woman she will invest in her beauty and not ever be a silly little purger. Thank you Marie for inspiring this audio.

Under Sissie's Dress Erotic Audio: Ms Cassandra 1-800-730-7164

The foundation makes the girl. It also makes the sissy, the crossdresser, the gurl. I’m going far deeper than panties, bras, and corsets. I’m talking about breast forms and hip pads that sculpt and create the perfect hour glass figure.

Last week Marie, a transgender gurl who does Skype calls with me , sent me information on the best silicone hip pads and silicone breast forms on the market. Pricey yes, but of great quality by DressTech. Both hip pads and breast forms should be in every gurl’s closet. Now that you know where to go, let’s talk about how these items empower a gurl.

Transgenders love the curves without the telltale lines and bumps. Spandex dresses on a sissy require the perfect hour glass figure, especially in a pretty light pink. Slut wear in tight red do as well, and nothing says slut more than a red and black tight mini dress. I advise a black lace cover on top of the scoop neck dress to hide the lines of breast forms depending on the type of forms you have. Listen to the audio…


Mistress Cassandra 1-800-730-7164


Humiliation Fun With Inflatables

Inflatables With Skype

Fun with inflatables started a few days ago as I was watching the mind fuck addict on cam. He had his lovely face covered with a black mask as he pumped up his big black anal plug, growing in his ass with my demand. That in turn spawned my post written . . . → Read More: Humiliation Fun With Inflatables

Sissy Prom Queen Erotic Audio

A sissy prom queen is what you aspire to be. Finally you have made it. It took a lot of hard work to reach the status. How did you get there? How did you do it? This erotic audio should give you a clue. Before you get off of your knees, make sure you . . . → Read More: Sissy Prom Queen Erotic Audio

Milking Time For A Sissy Fag In Chastity

It’s Milking Time

Yes it’s about that time. It’s been 237 days after all, so milking is in order. I ordered La Fag to purchase a most elegant milking device: the Njoy Pure G Spot metal wand. La fag has tried the Aneros in the past and it did not quite do the trick . . . → Read More: Milking Time For A Sissy Fag In Chastity

Chastity Lite Part 3 Erotic Audio

Chastity lite is the next step after your tease and denial period has ended. You have developed enough skill to understand denial and sexual frustration because you chose the path of chastity training for Mistress. Listen to part 3.


This recording focuses on “Chastity Lite” for the apprehensive . . . → Read More: Chastity Lite Part 3 Erotic Audio

SPH You Know What It Means!

SPH Is Fun To Write About

SPH is yes! Small penis humiliation. So many posts I have written of this but not lately. I was rolling on the floor laughing with my last call. Imagining his cock was a pimple, and squeezing it caused a little eruption of cum. Of course I would never . . . → Read More: SPH You Know What It Means!