Sissy Finishing School

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Sissy Maid Training

I’m a firm believer that every dominant woman should have a sissy maid. After all, someone has to take care of things when I entertain my friends, and who better to do it than you, the sissy maid? Not only do I get the amusement of seeing you strut around in a French maid’s uniform, but there is also the practical aspect of making you responsible for all shopping, preparation, serving, and clean up while I relax and enjoy myself.

Sissy Maids Should Be Seen and Not Heard

I really love this image that I found. It perfectly illustrates the true role of the sissy maid. The ball gag ensures silence…not that you will need *any* accessory to do as I say…and the serving tray is a nice touch. Though we can’t see what is going on with this particular sissy maid, or what she has been trained to do, I’ll let you in on how this all plays out in Ms Lily Land.

Your starched white apron conceals a chastity device and a hormone-weakened clitty. I like to lift that apron up, and show everyone what lies underneath. I’ll look you in the eyes, and ask you if that girlcock works anymore. Everyone in hearing range will listen for your answer. Just imagine the mortification you’ll feel as you have to shake your head, and confirm what we already know.

I Enjoy Humiliating You

The back of your uniform will have been altered to leave your ass exposed so that everyone can see that you are wearing a butt plug. Now and then someone will come up behind you, put the palm of their hand against the base of the plug, and give it a good shove. You bat back tears, and try not to droll around your ball gag. You know to do such a thing will bring a swift reprimand from me.

If I decide that I want to really have some fun, I may put you in ballet boots or heels that I know are too high for you to walk in. I can then make a game of it, and every time you stumble means that you have to worship someone’s ass with your servant mouth. Of course, I could just make you do those things anyway, but I enjoy the sport of it.

I enjoy fucking with you and training you to be the perfect sissy maid.

May 12, 2013
Strap-On Fun

Experienced Strap-On Mistress

Assume The Position For Some Strap-On Fun

As an experienced and knowledgeable sissy phone sex Mistress, I understand the utmost importance of thorough and routine strap-on training! If you are the type of sissy that desires to undergo this type of strap-on phone sex training then you have definitely come to the right place and I see you and I having a very bright future together.

The initial part of strap-on phone sex will include a special unit on cocksucking since your spit will often be used as your lube for anal training during strap-on phone sex. You will learn exactly how to please a cock through your strap-on training and you will, most importantly, become an expert on deep throating phone sex also!

Gagging On My Strap-On

As you are gagging on a nice fat strap-on from your sissy phone sex Mistress, you will find that your mentality will truly begin to transform into a much more slutty and feminine mindset.

After you have learned all the basics of cocksucking phone sex, you will then move on to anal training. I have much experience in teaching sissy phone sex lovers to adore anal sex, even though at first they may be apprehensive. I adore turning a sissy phone sex girl into the perfect strap-on slut.

We will start with a small strap on at first to help you adjust to the feeling of your ass being penetrated and used by a strap-on phone sex Mistress such as myself.

Pushing Your Limits With Strap-On Phone Sex Training

As you start to relax and enjoy the feeling, we will step up a size pushing your limits just a bit. You will feel a mixture of a slight pain and extreme joy. If you are an especially good sissy, I will reach around and play with your clitty as I fuck your ass pussy with my strap-on.

This will be just the beginning of your strap-on phone sex training and strap-on fun. Are you ready to be opened and penetrated? Then you know what to do sissy. Send me an email and tell me why I should accept you into my sissy strap-on training program. Until then…..

Ms Isabel

May 10, 2013
Night Time Crossdressing and Feminization

The Secret Crossdresser

Are You A Night Time Crossdresser?

I especially like men that are top level executives that maintain a very macho image during the day, but you have a very well kept secret behind your locked bedroom doors. You are a night time crossdresser.

You adore and fantasize about crossdressing. You even find yourself longing to be dressed as a woman during the day, but know that you must wait till you get home. You work hard, watching the clock ticking away, longing and waiting for that time when you get to be truly free to be yourself, donned in the garbs of a gorgeous and sexy woman.

Crossdressing and Feminization

As a crossdressing phone sex Mistress, I understand exactly what it is that you need during distant feminization phone sex. You need a feminine and fashionable crossdressing phone sex Mistress that can teach and guide you to become the best woman possible each and every night.

We will work together to keep you up to date on the latest trends in make-up, lingerie, clothing and shoes. You will stay waxed at all times and over time you will start to wear you lingerie underneath your executive business suit.

Distant Feminization Crossdressing Mistress

I know that you desire to be the best woman possible each and every time that you dress up, donning only the finest of clothing and constantly lusting to learn more about how to portray yourself as a proper, seductive and sexy lady.

As your crossdressing Mistress, I will be your teacher. The sound of my voice guiding you to move deeper into your desires and embrace the crossdresser within you. You will, under my guidance and care, become the best woman you could ever imagine.

Embrace Your Crossdressing Desires

If you want to learn more about how to become the woman that you have always desired to be then you should contact me. I am an experienced, knowledgeable and fashionable crossdressing phone sex Mistress and I would love to join you on your crossdressing journey.

Until then……

Ms Isabelle

May 6, 2013
Are You A Sissy Cocksucker

It’s So Easy To Pick Out A Sissy Cocksucker!

I Can Spot A Sissy Cocksucker Anywhere

I know that many of you worry that people may know your dirty secret of being a naughty sissy cocksucker. Maybe you even worry that some will know just by looking at you. The truth is that to the naked and untrained eye, you probably seem like a drab, boring individual.

It is likely that more often than not that people will just glance over you, taking very little time to figure you out. Then there are people such as me, a trained and experienced sissy phone sex Mistress and we know what signs to look for. We are able to spot the sissy cocksucker within just a few moments of meeting his acquaintance.

Subtle Signs Of A Sissy Cocksucker

Sometimes the first signs that give away a sissy cocksucker are subtle and likely to be missed by most. It could be something as simple as the slightly feminine way that you cross your legs, the way you raise your glass gently to your lips, or the way your hands move and gesture.

I can see past your macho mask that you are nothing more than a sissy cocksucker. You lust for a strong sissy phone sex Mistress to control you, guide you and teach you how to be the best sissy cocksucker possible.

Are You Ready To Be My Sissy Cocksucker

The longer that you and I interact, the more feminine each of your movements will become, your voice will soften into that of a more womanly tone, and you will find yourself even beginning to feel much more like the sissy cocksucker that you have dreamed of being.

The seductive purr of my voice and the knowing look in my eyes will drive you wild as we play an intimate game of tease and denial, pushing you to become my sissy cocksucking phone sex slave. The more I deny your cocksucking needs, the more you will want to do anything I ask, just to please your Mistress.

Now be a good little sissy cocksucker and come over here and kneel on that lovely velvet pillow on the floor. I have a nice, big surprise for you and I think you will love it!

Until later my little sissy cocksuckers,

Ms. Isabelle

May 3, 2013
Sissy Shopping Spree

Shop until you drop, sissies!

After years of doing feminization phone sex sessions and combined with face-to-face experience, I feel very safe in saying that as a whole, sissies love to shop. What exactly they like to shop for differs, of course, but if ever there was a demographic that defines conspicuous consumption, it is sissies. They love to wallow in all the accessories that go along with their fetishes and desires. And who can blame them? Shopping is fun!

The Panty Boy

Cross my heart, I have met panty boys that have far more panties that I do, and I am a lingerie lover. Whether it’s thongs, bikinis, boy shorts, high cut, rumba, tanga, shaper, crotchless, French cut, or any other variety…including dirty for some…panty boys L-O-V-E their panties. They have them in every hue and fabric, and are obsessed with getting more. One simply cannot have too many pairs is their motto.

The Cocksucker

This group really has no choice in the matter as to their sissy shopping. They will get whatever they are damned well told to get, and they will like it. Purchases often include slutty clothing, and realistic cock sex toys. Both of which serve to please Mistress when I make them open up their holes to serve. The feminzation slut may also be in financial servitude to me

The Cross Dresser

The CD may well bring home the gold when it comes to sissy shopping sprees. I have spent countless hours on the phone, shopping online with sissies, shopping at the mall with sissies, etc. Their sissy plumage varies. Some wish to blend in, and some want to proclaim to the world that they are indeed Ms Thang. Whatever their bent, they are a world-class triathalon when it comes to sissy shopping.

Transgendered Girls

Tgirls love to shop as well, and embrace all the femininity that they have been denied. They are often more careful with their clothing selections, and tend to value quality over quantity. These are not clothes that are going to be waded up and stuffed in a bin until they get the opportunity to dress again. Tgirls are building a true feminine wardrobe, and are prone to select things that they love that will last for years.

I love shopping with sissies. It’s such fun to pick out the perfect something for them, and then get to watch later on cam as they show me what we bought!

May 1, 2013
Have You Been Craving Sissy Phone Sex?

It’s time to call Sissy Finishing School!

Most of you have waited very patiently, though some of you have been a bit petulant in your emails. As a side note, I have special, special plans for those of you that fall in that group. The rest of you will be happy to know that at long last, your wait is over, and we are now accepting your sissy phone sex calls!

If you’ve been good…and I’m sure that you have…you’ve read plenty by now, and you know that Ms Isabelle and I do not offer a cookie-cutter site, nor do we offer cookie-cutter phone sex. There are multiple sissy schools online, but after spending time with us, you’ll never need to find another. This, dearlings, is your sissy school home, and we are going to have lots and lots of fun together!

So slip into your panties and grab your lip gloss. Prepare to divulge your deepest sissy secrets. You know that you’ve been searching for so long to find just the *right* woman to share your true self with.

We know it too.

April 28, 2013
Sissy and Transgendered Lesbians

Girl Power!

Before I get started, I wanted to tell all you anxious pets that the moment you have been waiting for is soon to arrive. In short, my darling Ms Isabelle and I will soon be taking your calls. So stay tuned for more info.

Now…on to the topic at hand. And one that I think really gets very little press. That, ladies, is the plight of the sissy or transgendered lesbian. When most people think of feminized girlmen or transgendered ladies, they imagine that they are all fantasizing about dropping to their knees and rolling their tongue around the head of a well-formed cock.

While that is true in the *majority* of instances, it is not at all true in all of them. Not in the least.

Appearances Can Be Deceiving

As we all know by now…or should know by now….if you don’t, you are forbidden from using your lip gloss for a week…appearances can be and often are deceiving. Just because someone looks one way doesn’t mean anything. Take me for example. I look rather friendly and approachable, I think. I can be those things, but I can also flog some sissy ass when the mood strikes me.

In that same vein, not all cross dressers, sissies, or transgendered girls want to give blowjobs. The very notion of doing it makes some of them queasy, and that group is what I refer to as sissy lesbians.

They’ve Got a Yen for Pussy Paradise

Though they are certainly not as commonplace as the sissy cocksucker, I’ve encountered more than a few sissy lesbians in my time. They are *especially* fun to feminize, because I know that each moment…each touch of my fingers…each time my perfume teases them…each time my breast brushes against them….well…each moment is sweet agony. They long to be my female lover, and have our soft bodies entwined.

Sometimes if a sissy lesbian has been particularly good, and I feel that she is deserving, I will allow her to glide her tongue over my clit, sucking at it, and licking my pussy until she brings me to orgasm. Of course, just because I let her lap up my kitty cream doesn’t mean that she gets to make any herself. Then I prefer to just let my nails trail over the front of her panties, and chide her for being such a messy sissy lesbian.

April 25, 2013
Sissy Sluts Have a Dildo Battle

Sissy Tug of War!

I went to a fabulous kink party tonight, and really got some good laughs. The laughs were courtesy of two sissy sluts, both attention whores, both catty as can be, and both determined to be the favorite sissy slut of the evening. In the heat of battle, I’m sure that they both thought that they were fierce. To me, and the other assembled ladies…real ladies…they provided comedic entertainment.

Their owners and I had talked prior to the festivities, and we decided that it would be a lot of fun to pit them against each other. There were going to be a few less competitive sissy sluts there, but we knew that those weak contenders would be blown out of the water by Miss Thang 1 and Miss Thang 2.

From Mild to Mortifying

The first few rounds were devoted to service and style. It was amusing to see the claws come out and the preening start. If you think that there are mean girls in high school, you haven’t see anything until you’ve seen a double handful of cut-throat sissies trying to out-do each other.

There were roughly 15 genetic women there, and we voted to see who was eliminated from Round 1. We then moved on to Round 2, where all sissy sluts had to perform on a stripper pole. We had laughingly told them that the best two performers on this pole would get to entertain us with another pole.

Some of the ladies really picked up the verbal humiliation during this Round, and it was easy to see the effect that it had on the sissies. As soon as we saw the slightest droplet of moisture on their panties, out they went. Soon we were down to just two contestants…the two we had anticipated.

Greedy Sissy Slut Holes Gobble Up Dildo

The shared Grand Prize for the evening was a doubled headed dildo. We had marked it at exactly the midway point. We gave the sissy sluts a few minute to lube up, then the whistle blew. It was up to each of these greedy sissy whores to prove who was the greediest. We had their hands bound behind them, so they couldn’t use them in any matter.

I laughed so hard that my side ached to see these wanton sissy sluts trying to keep their balance in a precarious situation, all the while trying to shove more of that dildo up their worthless cunt holes. It was like a bizarre tug of war and each time one would almost get to the point where it appeared that she would claim more than half the cock, the other would work her hips, grip that pole, taking it back for herself, and then ride it like crazy.

We ultimately decided that there was no clear winner, which made the sissy venom they were mentally spewing at each other become almost a palpable, breathing thing. We then made them return to service mode, fetching and carrying and try to regain their dignity after having wallowed on the floor like a serpent it heat.

But we weren’t about to let that happen! So the degradation rained down on them, while we showed them videos we had taken of their Battle Royale. They were shamed and we were amused.

Which, of course, means that all was right with the world.

April 20, 2013
Panty Boy Phone Sex Mistress

Are You A Panty Boy Seeking A Phone Sex Mistress ?

Are You Seeking A Panty Boy Phone Sex Mistress?

I know you are sitting there, already wearing your favorite satin and lace panties daydreaming about finding the perfect panty boy phone sex Mistress.

Perhaps you were lackadaisically browsing through the profiles of other, sub-par or mediocre, panty boy phonesex Mistresses when you stumbled across mine. At first you are stunned by the beauty that is before you. Not only am I gorgeous and experienced, but I wear clothing that perfectly accentuates my femininity.

You are frozen in time, not even able to stroke your cock through the soft material of your panties for fear of premature ejaculation. No… You must…wait. You know that you want to save this orgasm for me, your perfect panty boy phone sex Mistress.

You know in your very core that you would do anything to sniff my sexy panties and, oh, to wear the panties that have adorned the perfect body of your panty boy phone sex Mistress.

Panty Boy Will Do Anything For His Phone Sex Mistress

The moment that you hear my seductive and sensual voice you will feel something stirring deep within you. Your arousal will sky rocket as I whisper sexy nothings into your alert and attentive ear. The purrr of my voice will have you not only ready, but willing to do whatever kinky phone sex ideas that I come up with.

You are happy to play any of my naughty games as you earn the most desired sniff of my damp and musky panties. I will allow you to wear my dirty panties across your face as I guide you to the most explosive orgasm of your life.

I will take you on the panty boy phone sex adventure that you have always dreamed of! You will let go of all of your inhibitions with me. My guided masturbation phone sex will have you teetering on the edge of orgasm over and over again.

I will tease and deny you until you can no longer take anymore of my kinky panty boy phone sex. You will beg me to cum! As a reward for being the perfect panty boy today I will allow you to erupt into a flood of relief and intense pleasure.

Panty Boy Must Clean Up His Mess

Just remember panty boy, when I allow you to cum you must always clean up your mess. Now be a good little panty boy for your phone sex Mistress and lick up all those stringy bits and sticky goodness. Until next time my devoted panty boy phone sex lovers……

Ciao,

Ms Isabelle

April 17, 2013
Sissies in Chastity

No cummies for you!

Now, we all know that there are all types of feminization fans at Sissy Finishing School. But today, I want to talk about a particular sub-set of sissy that is near and dear to my heart. That is the sissy in chastity.

I am particularly fond of sissies in chastity for a number of reasons. The most important one is that said sissies and femgirls have accepted the fact that doing what pleases me is far, far more important than the fleeting pleasure that they might derive from an orgasm. While I do enjoy calls of all types, I do admit a fondness for what we’ll call the ‘service sissy’. The service itself can encompass a variety of things, ranging from, but not limited to, sissy maids, sissy financial domination and sissies in chastity. What’s one got to do with the other, you may ask?

The Common Denominator is My Pleasure Comes First

Some sissies are really very selfish, truth be told. I don’t really blame them for it. Their little heads get so rattled at the idea of getting to dress for me, service a cock for me, or whatever else may be their kink de jour. In all that excitement, they are focused on *their* excitement, and seeing that I am cared for, entertained, and amused fall to the wayside. While I can have a fun time in a session with those types of sissies, it is unlikely that I will form a substantial bond with them, simply because the proper relationship dynamic is that I come first. No pun intended.

Chastity is deprivation. It’s giving up for me. It’s making the sacrifice. It’s remembering that while rubbing your clitty without restrictions feels good, that it is a poor imitation of the pleasure you get by making me happy.

In the coming weeks and months…and yes, there is *that* word again…I am sure that I’ll be locking a few of you up. Each situation is different, and therefore, calls for a different approach. But all good sissys can find a way to devote at least some periods of chastity to me.

I know that the idea probably sounds hideous to some of you, but I assure you, though chastity is an acquired taste, I’ve turned more than one femgirl sissy slut into a chastity addict. You will be no different.

April 14, 2013