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October 2016
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How To Stay Active In Chastity Audio


There is locked slave rob on the left. one of his assignments is a picture a day in panties with cage on, and a humiliating affirmation written out on the board with the picture. Now give a listen on how to stay amused and stop thinking about your imprisoned cock…ahem…Mistresses cock that is!


Staying active in chastity. Hmmmmmmm…. Well since you do have a series of cages, your beloved metal chastity cage, and a soft silicon one for working out at the gym, you are all set!

But what about when the assignments have been accomplished and there has been no tease and denial for awhile? I suppose you can take up basket weaving to calm your stroker boy nerves. Sissies in the pink cage can knit pretty pink sweaters, porn addicts can be tied to a chair and tortured into watching the porn of choice. Things like that. Eventually when Mistress takes you out of the cage, and you reach the final day of your sentence, she may put you in orgasm marathon mode, demanding, if you do not do the allotted number, the next chastity sentence will be doubled!

You would be luckier with a ruined orgasm. Whatever she decides, just a s slave rob does in the picture posted:

“Mistress can do whatever she wants. I wait at home on my knees because I am pussy whipped in chastity. Day 72”

Now then, locked slave rob is scheduled to cum on day 80. Hmmmm we will see about that!

Mistress Cassandra 1-800-730-7164


Small Cock: What More Can I Say

Mistress Cassandra 1-800-730-7164

Little Dickie Danny! Your “Cock” Shrunk!

Little dickie danny! After so long! Just the time, not the dick. I seems to me that little dickie danny’s small penis has gotten even smaller. To top it off, it doesn’t want to get hard and cum. Well, we will see about that. I remember the fag that he is, and often the fantasies run to big black cock, but danny is a grab bag of lots of things. From cuckolding, thick bodied women, to body builders. I remember this particular phone fantasy of watching a big muscled black man in Venice Beach wearing only a cod piece sweating and grunting in the sun. then there was jeffie! Didn’t think I remembered jeffie o danny boy? They all led to blow jobs of course.Thank you for the small penis pictures. I love seeing progress!

Mistress Cassandra Says

The Chaste Camp

Some chastity news here. Today marks day 130 for sissy donna, scheduled to get the Xmas blast and out of chastity for a vacation then. Her breasts have taken on a new dimension too. She has been using a new product called “Natureday” available on line. It is 100% natural and organic which I approve of. Of course it will work slower for a sissy. Patience.

Locked slave rob is at day 67. He has to reach 74 for his/her personal best. I love getting the daily frustrating “I’m so horny” emails all ending in another day of orgasm denial in chastity! A picture a day, and always surprise panties. I love that as they are never ordinary.

Chastity Trainer Mistress Cassandra 1-800-730-7164


Sissy Show At Ms Violet’s House


Wine, Cheese, and Sissy

Ms Violet and I had a fun filled evening at her house around the block. I brought over a bottle of wine and she had some cheese and pears for snacks. The entertainment was a call from sissy lacy on phone and on cam. What a delightful surprise when she gave us a private concert on her baby grand piano. She played everything from Stevie Nicks to Leonard Cohen, and she played so well, presenting a composition she was working on, and giving us some great jazz piano ala Kieth Jerrett. Ms Violet told me lacy gave her a four hour concert one night! Lacy needed to warm up first for her “doctor’s appointment”.

Dr Cassandra and Dr Violet

Outrageous sissy lacy came to her appointment with Dr. Cassandra Jones promptly and very meekly. Dr Cass always looks forward to seeing lacy because lacy has come out and wears the most impeccable sexy lace panties. Dr Cass is not alone. Dr. Violet Avery is in the next room curious to see the well lingeried sissy.

Open Wide, Gurl

Dr Cass does her routine exam, and has sissy lacy bend over the table for her prostate exam. Lacy is wearing a pretty pink bra and teddy with black lace panties. She is ordered to keep it on. Dr Cass wants a second opinion and invites her colleague in. In walks the beautiful Dr Violet for more anal action.

We Need A Sperm Sample

Sissy lacy at this point is ordered on her back and we see the sexy lingerie she has chosen for this session. Of course she knows she will be submitting a sperm sample. After much tease and denial, some strap on sex action was in order so as to produce the most amount of sperm for the sample. As Dr. Violet used her vibrator on lacy’s little ovaries to produce a sizable load, the goal was achieved. Sissy lacy had cream filled panties. What a great phone fantasy this was.

Mistress Cassandra 1-800-730-7164


Poor Sissy Audio



So if you are going to go full on sissy, go full on girl. Study study study, walk, talk. Read Allure and Cosmo! Religiously.


The email:

Mistress, I really don’t know what more I can do to be more femme, since I have been managed by you. I have grown to be very sissified, very submissive, I harbor deep fantasies about sucking cock. I have a huge wardrobe of female lingerie and clothes, I get excited about going out to bars wearing a short skirt and sheer pantyhose, I have large tits and nipples that are constantly tingling, my housekeeper is always shocked because I wear tight leggings and a bra around the house when she is here. Apart from getting a vagina, I don’t know what else I can do, I am about as femme as I can possibly be or am i? I am going to get a permanent sign that will forever mark me as a beta male and cocksucker of BBC. I like this tattoo, which I will have on my pubes and both of my ankles.

My reply to this:

A perfect tat for you although it is the mark of a cuckold beta male who fluffs big black dick. Get that tat in bright pink. You are not a male remember.

Well now, you have not fulfilled your cocksucking assignment. Gurls like you do suck cock after all. Do what real girls do. Suck cock, have periods, and flirt with men. Besides getting a tit job and dick removal, reflect on what excites real girls.

Mistress Cassandra 1-800-730-7164

The Stroker Boy Worship Shrine


A New Stroke Pet

Matty stroker made this shrine after days of stroking and edging. The assignment proved to be very grueling, so he needed a break. Stroking less and to the shrine, added variety to his instructions. Today he is on a whole week of zero stroke unless he sees his girlfriend.

Training The Dominant Male

Since I never mentioned this boy before, I will now. His girlfriend is the submissive, he is the dominant. He came to me to learn cock control so he can better serve her sexually. I will train all kinds of boys, even dominant ones as long as they know their place with me, and this boy knows his place. He is well read in BDSM, and is a very good Master to his submissive. He is not abusive and he holds her in high regard. He also holds me in high regard which is essential. I’m not sure if I will ever get to talk to her, eventually when the timing is right.

A Kinky Switch

Today mat stroker was of course denied orgasm. We used clover clamps on his nipples and a dildo in his ass. As you can see, this boy is a bit of a switch. I love the job he did with this shrine or altar. The red works best, and the presentation is very sexy. This boy is a precum and cum eater, loves to be a sissy with panties and nighties, and has toys. Now the cum eating we save for a later time, when he is allowed to cum.


Mistress Cassandra 1-800-730-7164


The Cuckold Vows Audio

I love it when a boy writes a script that’s wonderful and creative. Here is one by little donnie dickless aka LDD. All words are LDD and what a very bad boy he is.


Carol is dressed in her original wedding gown which has been modified for the cuckold ceremony. . . . → Read More: The Cuckold Vows Audio

Sissy Maid On Loan Report

A Sissy Maid’s Duties

Now I have a spotless house, sparkling stainless steel cookware, rugs vacuumed and shampooed, a spit shined toilet (lol), counters polished, glasses without water drops, drawers organized, shoes perfectly cleaned, and a hearty buffalo stew made with red wine and fresh root vegetables. All of this done in a . . . → Read More: Sissy Maid On Loan Report

Domestic Slave On Loan

Chores Will Be Done

I have a Mistress Friend with 2 slaves in town. Tomorrow my house gets scrubbed from top to toe. She is loaning me her sissy domestic slave for the day and I have some work for her, absolutely. It just so happens that my boy Matt is in town . . . → Read More: Domestic Slave On Loan

SPH Made Easy Audio

What came first the “cluckold” or the small cajones….. give a listen small penis cuckolds.


Small penis humiliation is effectively done with exaggerated variety. The lineup of slaves to determine who the winner is. Meaning the smallest or the largest? Since self esteem is mostly low with little . . . → Read More: SPH Made Easy Audio

How To Discipline Your Unsupervised Cock

Hands Off!

I could easily say do not touch it! Do not stroke it, don’t even think about it. Often no matter how owned and dedicated to a Mistress a boy is, sometimes they simply slip up. For example: locked slave rob is locked in a metal chastity device with his key in . . . → Read More: How To Discipline Your Unsupervised Cock