Sissy Finishing School

Category: Feminization

Sissy Humiliation

I will give you sissy humiliation!

While I really love and respect transgirls that are serious about feminization, the sadist in me loves sissy humiliation too. There is just something about taking the fact of someone’s sissy status and rubbing it in their faces that pleases me. I have seen things in person and on cam that make me grin just thinking about them!

Sissy Humiliation and BDSM

Sissy humiliation is just another form of BDSM, and one that I thoroughly enjoy. It’s just like being a pain slut, though the pain is mental. It also has to have context to make it enjoyable for me. For example, I have tons of gay friends, and am an active supporter of LGBT rights. I would never in a million years do anything to hurt the feelings of my friends. But in the right context, I love telling someone what a cocksucking little faggot they are. As with all things BDSM, it is the consensual nature that causes something that would otherwise be unacceptable to be a great deal of fun.

Types of Sissy Humiliation

Humiliation play is intensely personal. What is a trigger for one person might be heart wrenching for another. So a good understanding of where the play is going is important. Once that basic foundation is in place, there are a vast array of ways to play that involve sissy humiliation. They range from sissy puppy play to being a sissy money slave, with a world of fun packed in between those two.

Erotic Humiliation Addicts Know Themselves

Some people might recoil in horror, thinking that it is awful that I derive pleasure from telling some sissy that her only worth in life is to be a cum dumpster for bukkake parties. What is important to understand is that fans of erotic humiliation know their own triggers. They’ve lived them out in their mind time and time again. They know exactly what words or acts take them to the edge, where they are shivering in anticipation of the explosive orgasm that is about to rock their core.

It’s just so much better when they get to share those fantasies with me.

August 16, 2013
Sissy Schoolgirls

Ring in for your assignments!

Even though it is still August, the signs are everywhere…it’s back to school time. That not only means traditional schools, but it’s time for you sissy sluts, fabulous fembois, cute crossdressers, and tantalizing transgirls to get your acts together. You’ve had all summer to flit aimlessly about, doing your work now and then, but never really buckling down.

You’ve not yet committed to being the best sissy schoolgirl that you can be.

There Are Different Kinds of Sissy Schoolgirls

Some of you already know what type of sissy schoolgirls that you are. You will automatically know that you are the class harlot and are a cocksucking sissy slut, or that you are one of those sissy schoolgirls who cannot get enough of rumba panties. If you know, that is terrific! We’ll have fun putting you through your paces, and testing you to improve your skills along the way.

But you may be a lost sissy schoolgirl, unsure of which curriculum is best suited for you. Have no fear, that is one of the reasons that Ms Isabelle and I are here. We will be very happy to guide you in your explorations, and to give you the benefit of our wisdom in feminizing sissy schoolgirls. Besides, it is fun to explore, and try things that are challenging. Especially when you are doing them under our tutelage.

Some Sissy Schoolgirls Need Sissy Assignments

There is a portion of the feminized population that will get along just fine without any activity between calls. They are able to weave being sissy schoolgirls in and out of their lives, and compartmentalize their time. Other sissy schoolgirls *need* assignments and homework. It helps keep them on track and disciplined when we are not available.

Assignments can be a great deal of fun, but I personally enjoy giving them most when they are tailored to the individual, and are not one-size-fits all. Not all sissy schoolgirls will want to try out for the cheerleading squad, and not all assignments fit all sissies. For best results, and to get the most out of assignments, call us to design a training program just for you.

August 8, 2013
Sissy Maid Duties

Responsibilities Of A Sissy Maid

Duties Of A Sissy Maid

I have trained and been host to many different sissy maid fetish role plays. This experience has led me to realize that a sissy maid has many responsibilities to the master or mistress that he is to serve.

A sissy maid is a domesticated male that dresses up like a sissy maid, complete with the french maid outfit (often in bright pink to emasculate him further). A sissy maid often finds sexual pleasure in even the most simple of domestic of tasks, which is good since a large portion of her responsibilities will be domesticated tasks.

A sissy maid will be in charge of keeping the entire house cleaned and will happily do the laundry of her master or mistress. In the kitchen, the sissy maid will be in charge of making meals and snacks.

Finding Pleasure In Sissy Maid Duties

The sissy maid is also responsible for keeping an inventory on any and all items that need to be replaced over time; this includes but is not limited to grocery list, bathroom supplies, dungeon supplies, and resupply of the finest wines.

As a proper sissy maid, you will be responsible for light secretarial work as it is needed to assist your master or mistress. You will take phone calls and record messages as well as do any research that dominant requires. You will learn to find pleasure in even the most mundane of tasks such as data entry when it is being completed for your dominant.

Transition To A Sissy Maid

Whenever the master or mistress has guests over, you will not only be the sole caterer of the event, but will be in charge of keeping guest entertained in anyway possible. This could be as simple as taking coats for safekeeping, keeping the music going, serving drinks or even sexual use. That’s right little sissy, you may be put on display for some pegging events! The word “no” is not in a sissy maid’s vocabulary as she works hard to keep the guests happy.

These are just a few of the basic tasks that you would be required to carry out over time! If you want to learn more about how to make the very real transition into a sissy maid then call now to start your journey.

Until later….

Ms Isabelle

June 21, 2013
Being A Sissy Diva

Helping The Sissy Diva Get Ready For The Big Date

Let’s start off by saying that I know a thing or two about being a Diva myself, which means that I know exactly how to help a sissy Diva get ready for her big cocksucking date.

Being the Diva’s that we are, we started out the day at a spa where we had pedicures, manicures, waxing, and massages. We then hit the tanning bed for a few minutes before we picked up smoothies and headed home to really start getting ready for the big date that night!

We gossiped and chatted excitedly as we went about putting on only the hottest and trendiest make-up that had us looking like Goddess’s. I then helped her with her GORGEOUS long tresses that makes her look like a real sissy Diva even before getting dressed.

I know that anyone would be jealous of this sissy Diva’s luxurious head of hair! She was looking so hot already, especially with those pouty bright red cocksucking lips and all of her dazzeling jeweled accessories.

A True Sissy Diva Standing Before Me

We had both picked up a sizzling hot little mini-dress and matching strappy stilettos the day before when we were out shopping. As I zipped up her dress, the sissy Diva pulled up her matching thigh high stockings that just barely showed when she crossed her legs.

The strappy stilettos finishing off the ensemble. She spent a while staring at herself in the mirror, twirling around slowly taking in her stunningly sexy body; A true sissy Diva was standing before me.

Being a true sissy Diva means believing in yourself! Your presence and confidence filling the room as you strut around in front of the mirror, prancing and preening like a runway model. There was a distinct look in my sissy Diva’s eye that told me she believed that she was the best cocksucker around and she was about to show her lover just what she was made of!

Would you like to look as stunning as my sissy Diva? All you have to do is call and be ready for my expertise in creating the perfect sissy Diva.

Until later…….

Ms Isabelle

June 17, 2013
Feminization Makeup Lesson – Mascara Part 2

Flutter Your Sissy Lashes

Now that you’ve collected some of the necessary tools for feminization makeup, it’s time to learn to make those eyes look bigger. That not only enhances your overall beauty, but for those of you that will be cock sucking sissies, it will make you look so feminine as you look upward with a mouth full of real man meat.

If you got a lash comb, we’ll want to start off by using that. If you have a magnifying mirror…and some of you probably need that to make your little sissyclittys seem bigger…this would be a good time to use it. We want to separate your sissy lashes, so that the mascara will apply to each individual lash.

Lash Curler or Sissy Ovary Crusher?

If you’ve not practiced with feminization makeup tools like a lash curler before, be careful. If you get it too close, you can pinch the flesh of your eyelid. Off topic, but I wonder if I could squeeze one of those hard enough to properly castrate a sissy?

At any rate, carefully position the curler at the base of your lashes There are a couple of ways that you can do this One is to put the curler in place and squeeeeeeeeze! I prefer that you do that, as it gives a more anime effect. Count to 15, then release the tension, then repeat. After you’ve done the second cycle, open the curler, remove it, and repeat the process on your other lash. Transgendered girls who are going for a more natural look can make gentler squeezes, in sections up the lash

Get Girly – Mascara Application

Get your mascara, and open it. Do not get into the habit of pumping the wand furiously in and out, the way you would love to pump a real man’s cock in your manicured fingers. To do so forces air in, and the induction of extra air reduces the shelf life of the product.

If you see any clumps of mascara on the wand, slide it back into the tube, and gently rotate it to remove them. If that doesn’t do the trick, lightly wipe off the excess with a tissue.

To prevent smearing, I start with my top lashes, and so will you. Put the brush at the base of the lashes, and make a gentle ziz-zag motion with the wand as you move it upward. Use a light hand; you don’t want to mess up the curl. You may want to go for a demure look, and you may want to go for wanton sissy slut. Repeat layers according to what you hope to achieve. If you are going to do more than one layer, only wait 15 seconds or so between layers. Otherwise, you may end up all with your lashes in ugly clumps.

When you have the top lashes done, gently sweep the wand over your lower lashes. Unless your goal is to be a Sissy Goth Harlot, one coat will be sufficient on your lower lashes. If you get some on your skin, just dampen a Qtip with your eye makeup remover, and lightly go over your boo-boo until it disappears. You can skip the bottom lashes altogether, if you like. I often do.

When you have perfected the technique, send me a picture of your feminized eyes. Who knows, I may post it here for everyone to see!

June 14, 2013
Feminization Make Up Tips – Using Mascara

Feminized girlyboys and transgenders phone sex callers often speak wistfully about the experiences that they did not get to have as a female, and many of those focus on things that we tend to think of as rites of passage. Young girls in our society are typically taught or have permission to explore things that boys just aren’t. Makeup application is one of those things.

The past is gone, pets, and there is no reason that you should deny yourself the opportunity of having that learning experience now. Especially now that you have the guiding hand of Ms. Isabelle and myself. So today we shall focus on feminization make up for beginners.

If you are an advanced pupil in makeup artistry, you are to spend your time putting together your best look, then calling in for a session, and showing me in a cam show or with pictures.

Your Feminized Eyes Are The Window To Your Girly Soul

We are going to start with something very basic, and very subtle. You’re going to need some mascara to begin your feminization make up journey. To make removal really easy, and avoid the “raccoon eye” look, I highly recommend Lancome Bi-Facil Eye Makeup Remover. You will also want a standard bag of cotton balls. We don’t want to use tissue for removal, as it is harsh on the delicate skin around the eyes. Slightly advanced tools are a lash comb, and a lash curler. Go ahead and pick those up as well, if you want.

You can buy mascara anywhere that sells makeup, including drug stores and upscale department makeup counters. I have favorites in both areas, so if you want to be like me…and why wouldn’t you?…you’ll want to go with one of these:

Cover Girl Exact Eyelights Eye-Brightening Mascara is basic black, with four different versions. Each one has a slight tint of color to help you eyes really pop. Which shade you get is supposedly dependent on your own eye color. I don’t like to be beholden to rules, so just get whatever appeals to you. I have all four, so you won’t go wrong if your mission is to emulate me.

Shiseido Perfect Mascara Full Definition is also a personal favorite. I’m a fan of every Shiseido product that I’ve used, so make note of that when it comes to future purchases. I don’t care for brown mascara, so black is what I buy.

Lancome mascara in general tends to have a cult-like following, so if you want to get your hands on a real girl must have, this is it. Size queens will love the way that Lancome Hypnose Drama Instant Full Body Volume Mascara makes their lashes fuller and thicker.

Get prepared, get your recommended products, and report back for Part 2, where we will discuss application techniques.

June 9, 2013
Dancing Sissy Sluts

Shake that moneymaker, sissies!

Sissy sluts can have the best hair, makeup, clothes, etc, but one of the most challenging part of being truly feminized for most of you is learning to move your body like a girl. Over this long weekend, I got to see a *fantastic* example of that. Some friends and I went out to a mixed club for a little fun. In case you don’t know what I mean by that, it’s a place where everyone from every point on the sexual spectrum is welcome. Or legal points, that is .

I had an overall great time, but that time was made spectacular by watching a feminized sissyboi dance. This little honey knew how to dance, and she had every cock in a 10 yard radius focused on her ass as it gyrated in time with the music. It was obvious that she loved the attention, and that she would be able to milk a cock dry in no time at all with her hip control. Which is what made me think of a few of you.

Twerking 101

There is a video for nearly everything that a person can imagine, and that is true in this case as well. So let’s watch, shall we?

I want you to do whatever makes you feel the most feminine, and I want you to watch this video, and practice, practice, practice. Consider this an assignment, and once you’ve got it down pat, you are to ring in, and give me a cam show while you do it. I will be the judge of just how well you can move that body.

May 27, 2013
Sissy Assignment – Plan Your Feminized Sissy Wedding

I will feminize you & be your wedding planner!

While some of you yearn to be a true sissy slut, some of you recoil at that idea. You want to be a beautiful, feminized lady that is wooed and swept off your feet with romance. And what is more romantic than a perfectly planned sissy wedding?

As May begins to wind down, brides-to-be all across the land are waiting eagerly for June. And you are no different than them, are you, lovely? You want to be completely feminized for the fairy tale wedding of your dreams.

First, the Sissy Wedding Dress

Being a good sissy, you will have done everything that we’ve told you to do thus far, and that means that you already have a free Polyvore account. You are to go there and create a set that illustrates exactly the look that you want for your wedding. Do you favor the traditional look with a train and a veil? Or do you like the idea of standing barefoot on a beach, with flowers in your flowing hair? Express yourself! This is your special day, and we want to know how you envision it. Then you are to come back here, and leave a comment with your Polyvore user name so that we can see your creation. If you are not following us there, that means you haven’t read everything that we’ve posted, and you will receive demerits for that.

Details, Details

In addition to showing me what you want to look like, I want you to leave a comment that answers the following questions about the way that your perfect bridal day will be. Do you eagerly embrace this feminization for your sissy wedding, or do I force you to do it? Do you dream of marrying a handsome man, or do you like to think of me taking your virginity with my strapon? And finally, you are to share one detail about your wedding that is something that you really long for. It can be anything from the type of flowers, the flavor of mints, or the size of your groom’s cock.

Whip out those planners, girls. You’ve got work to do.

xoxo
~Ms Lily

May 20, 2013
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
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