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June 2017
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Sissy Swim Suit Modeling

Welcome to Cassandraville 1-800-730-7164

Sissy Swim Suit Contest?

It’s summer and it’s time for a sissy fantasy swim suit post. I want to see an itsy bitsy teenie weenie pink polka dot bikini, as the song goes, but not yellow. An itsy bitsy teenie weenie is mandatory, sissies do not have big cocks and should not pretend they do. Sissies do well on small penis humiliation.

Mistress Is The Judge

So I am fantasizing about a dozen sissies or more, all lined up by a pool. Mistresses sit at a table and are prepared to judge who is the winner, what the prize will be, and how much talent each sissy has. What is the prize? The big prize is sissies biggest unfulfilled fantasy made real. One sissy may like a delicious bi-cocksucking experience with a really hot man. Another may want to be sissy maid for a week at the home of a Mistress, one may want an all expenses paid shopping humiliation trip at a mall.

The Rules For Sissy Or You Are Disqualified

Right now I can tell you the rules, no thongs because no one likes the site of balls, little cocks taped back, breast forms of any size a must, must have tan lines going, pageant makeup, nails done, 5″ mules, wig or hair styled, absolutely no body hair, and of course pink rules.

What Will You Do With Your Prize?

Sit back and fantasize winning this contest and post under comments what your prize will be. Imagine the most outrageous that makes your little dick hard. You are parading in your ultimate girlie demeanor to win this modeling contest whether it be sucking a big cock or shopping at the mall. Get to work sissies and tell me your prize!

Mistress Cassandra 1-800-730-7164


Human Lampshade Humiliation Revisited

Human Lampshade Humiliation Objectification

Lampshade humiliation is for boys into being objectified in an odd and different manner. The versatile part of this human object genre is a Mistress can “fit the fetish”. She may dress the object as a sissy, harnessed, in CBT gear, or anything that pertains to the slave. Of course, I would add a chastity device always.

Chastity Slut Krista

This subject resurfaced with “krista”, a part role play, part reality chastity slut who called last week for a specific request. The slut is in a metal cage from the koala fag site, koalaswimwear. I was just on the chastity cage link and the names for these cages made me crack up…names like…”never been kissed cock cage, peanut, pea pod, OMG micro cock cage, things like that. You know, humiliation with your chastity training? Yes please.

Krista’s Humiliation

Krista’s humiliation is cum eating, in chastity forever, and the scene is, I am her probation officer, all decked out in uniform. The session ends in more time added to her sentence of orgasm denial. She must fulfill assignments. Her first failed assignment was wearing a speedo bottom and an “I swallow” t-shirt to the beach. Failed. More days added to sentence.

The Lampshade Assignment

I think a floor lamp must be purchased at a thrift store, preferably old with a large lampshade to stand in a corner with krista as part of the lamp wearing panties and her cock cage for party time. Mistresses can turn the lamp on and off,  pull on krista’s cage, snap her panties at the waist, give a little nipple play demo, and give butt plug training. Krista will provide me with a photo of her hidden beneath the lampshade standing military straight. This may be in her future humiliation assignments.

Mistress Cassandra 1-800-730-7164

Ball Busting With A Bang!

How Do You Like Your Ball Busting?

What is ball busting with a bang? Well now, while searching for ping pong paddles I came across some very fancy leather ones unlike the wooden ones of the past. Why search for ping pong paddles? Because they are pervertible with a broad surface for the maximum pleasure of ball busting. If you love CBT that is.

Ball Busting Can Be Rough

This practice is not for all. It’s a bit rough, rowdy, and most likely to be seen in the gay leather crowd. A more tame version is with the use of a ruler. Ball busting is the extreme form of CBT where the balls receive corporal discipline. Ball slapping with leather gloves is very sexy, using a small cock whip is hot, an uppercut punch using restraint, and of course squeezing the balls with a cold cruel stare is always affective.

BDSM Play + Ball Busting

This genre fits in well with any form of BDSM play as long as the slave agrees to submit to the discomfort involved. A well rounded, thorough variety of dungeon play would include this dramatic fun. Where does the bang come in.

Enter The Ping Pong Gun

A dominant could tie the submissive to a bondage table with legs spread, pulled and tied where the wrists are. Target practice with one of those ping pong guns, or even better, a paint gun, can be a fun diversion for Mistress. A whole contest can be arranged to see who can hit the target as many times as possible. In this position, just about any CBT toy can be applied. Ideas and comments appreciated. What are your ideas for ball busting with a bang. No comments with real firearms please. A worried submissive would want to keep those balls intact!

Mistress Cassandra 1-800-730-7164

The Cuckoldress And Her Brave New Bull

The Cuckoldress Knows What She Wants

The cuckoldress knows that a big black cock is the only cock to shop for. She belongs to cuckold fetish clubs that host parties and events. Her husband is her hapless little cuckold slave with a little penis tucked into his sissy panties. He has been trained efficiently since the beginning of their relationship to be her little groveler.

The Sissy Cuckold

Since the cuckoldress loves to be entertained, she takes him shopping frequently and announces in the lingerie store that the panties are not for her, but her husband who is a femmy sissy. A panty a day keeps the corporeal discipline away, but often times he craves it for his punishment being a beta male.

The Cuckold Hamper Slut

After long walks to an all black male frat house, she returns home with cum filled panties which the cuckoldress either puts over the cuckold’s head or simply puts them in the hamper for the cuckold’s discovery and hamper diving the next day. This gives the little dicked wonder something to do as the cuckoldress seeks out more big black bulls for her satisfaction.

Cuckoldress Has Sex Toys

Other projects she gives beta sissy, is sucking on large black dildos for practice, and training with various size butt plugs to prepare for the huge strap ons. Of course Mistress prepares sissy beta for the bull who will humiliate sissy with his huge cock. Sissy will often fluff the bull, and submit to anal sex when Mistress is just too tired.

The Happy Threesome

What’s next for the cuckold couple is a threesome in front of the sissy husband so he can finally see what a real dick looks like, how is efficiently performs, and how it makes his cock hungry wife mistress happy. His only enjoyment is cuckold and small penis humiliation and being a cream pie boy.

The Cuckoldress Mistress Cassandra 1-800-730-7164


The Ruined Orgasm Marathon Boy

Ruined Orgasm Marathon Fun

The ruined orgasm marathon boy does not like to be mentioned, nor does he comment. He is low key, so he says. Boy did not do so well in orgasm denial. He would end up teasing his cock in the shower and then blasting. With tease and denial phone sex calls he was just as bad. He would start edging his cock and lose control. Bad! At least he would tell me.

The Ruined Orgasm Marathon Defined

What is a ruined orgasm marathon you ask? It is simply ordering ruined orgasms with each call. Marathon orgasm is different. This requires masturbation endurance and the ability to cum at least three times in one session. With a ruined orgasm, a marathon ruined orgasm is close to impossible because of the blah or painful sensation after. So for the sake of simplicity, this type of cumming is achieved with multiple calls.

What would be interesting is a ruined orgasm marathon could be achieved with a pass the penis session with one hour breaks in between each phone sex call. This still requires dedication, stamina, and a passion for masturbation games.

Preparing For The Ruined Orgasm Marathon

The best way to prepare? A whole week of orgasm denial with absolutely no stroking while watching the porn of choice. Some vitamin v taken every other day and then, finally, on the day of the pass the penis, six Mistresses providing masturbation management. Vitamin v , porn, Mistresses, set the stage for six ruined orgasms with the one hour break in between.

Ruined Orgasm And True Submissives

Are you up for the ruined orgasm marathon game? Prove to your Mistress that you are a true submissive boy with tons of control. Take time to prepare for this adventure, and I don’t want to hear that you are too old, tired, or overworked. The only thing that will be overworked in this game is that cock!

The Ruined Orgasm Mistress Cassandra 1-800-730-7164


Truck Stop BJ Boys

Sissies, Trannies, and Truckers

Top of the list fun callers: trucker sissies picking up trannies at truck stops. They don’t have to be trannies either. They can be real men truckers having pancakes and coffee just wanting a blow job. Trannies are top shelf because they are the ones waiting outside the restroom . . . → Read More: Truck Stop BJ Boys

Ruined Orgasm With CBT

Cock Multitasking

Would you like some CBT with that ruined orgasm? Ending a CBT session with a little “thwacking” if done just right will lead to a spectacular ruined orgasm. How to attain it? Communication of course, and very good timing.

Sexy CBT Toys

Starting off with real CBT toys sets the mood, . . . → Read More: Ruined Orgasm With CBT

Ruined Orgasms 101

Let’s Ruin An Orgasm!

Today is a good day to ruin an orgasm. Tomorrow is better as I will be on to take your calls early around 9 Pacific/Az time. It is phone sex so your cooperation is necessary. If I were there with you, I would see the facial expression, the rising . . . → Read More: Ruined Orgasms 101

A Classy Sissy Calls

Super Sissy Brandy

I had the best time this morning with brandy bree, sissy extraordinaire. It’s about time we hooked up too, being from the bay area like I am. We discussed the same tranny clubs, glory holes, strip clubs, adult book stores that were once there and gone. She found it quite . . . → Read More: A Classy Sissy Calls

Cock Training Communication

Don’t Be An Orgasm Denial Failure

Cock control training is no joke and not taken with a grain of salt. The agreement of the beginning of the orgasm denial program is taken very seriously by me. So in other words, if it is requested for such a program and the next call proves . . . → Read More: Cock Training Communication