Sissy Finishing School

Author: Ms Lily

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
Fluff a BBC for Me, Sissies!

Fluff that BBC for Ms Lily!

Today’s lesson will focus on how to properly fluff the highly-sought-out, thing of legend that causes sissies everywhere to shudder in pleasure in the depths of their bellies. Yes, ladies, I am talking about the BBC.

Big

Black

Cock

I have plenty of uses for them, as you might well imagine. However, there is one thing that I am not fond of, and that is cock sucking. But there is no reason to be, when I have sissy slut cocksuckers to fluff for me. In fact, there is no shortage of your kind, truth be told. Sometimes…for fun…I like to create a competitive environment, so that sissy bitches have to admit just how much that they want to be the one that gets the honor of fluffing a cock that is going to plunge into my pussy. And it is an honor. Make no mistake about that.

And you want that honor. I know that you do, even if you can’t admit it to yourself. If it is necessary, repeat a mantra of “I fluff to serve Ms Lily”. Of course, you’ll need to do that in your mind, as your mouth will be full of black man meat, and you will not be able to talk.

On Your Knees, Bitch

You are to kneel before the real man with a penis that can satisfy me in ways that yours never could, even if I were to allow you to get that dicklette anywhere near me. It doesn’t matter the size of your sissy stick…it is the fact that it *is* a sissy stick that means that it is woefully inadequate for the task of pleasing me.

Because you are trying to earn top marks, no use of the hands will be allowed. In fact, now that I think of it, you are not yet proven stock, so you are not allowed to actually fluff the big black cock either.

You can, however, fluff the big black testicles. You will suck them, lick them, and run your lips over them until the cock is fully fluffed.

And of course, I’ll comment on it all the while, adding to your humiliation.

Ready to fluff for me? Give me a ring, and let’s see what you’ve got.

June 5, 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
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
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