Sissy Finishing School

Tag: sissy assignments

Feminization Assignment – Creating the Smokey Eye Look

Some of the more popular feminization assignments at the Sissy Finishing School are those involving makeup tips. You devour them like Godiva chocolates, all in your never ending quest to be as much like a real girl as possible. To that end, today’s feminization assignment should keep you busy until I’m taking calls again. You can perfect the technique, then send me pictures or give me a cam show to demonstrate how hard you’ve tried, and how much you want to please me.

Slutty and Sophisticated Makeup for Sissies

The smokey eye is such a multi-purpose look that you simply must have it in your arsenal of tools. It allows you to not only look like a pure slut when so ordered, but does double duty and can be sophisticated as well. And how do you go about creating this feminization masterpiece? As with so many things in life, having the proper foundation is key, and we’re going to start that off by using primer. Too Faced Shadow Insurance is a good one.

You’ll also need eyeliner. If you are in the beginning stages of your feminization makeup exploration, I recommend pencil over liquid. You’ll make mistakes, and pencil is far easier to deal with. It’s also best for smudging, which is a key component to this look. For the sillier sissies amongst us, you’ll also need eye shadow. Though many associate “smokey” with black, that need not be the case. Your dark shade can be a jewel tone deep purple, forest green, or any color you want to experiment with.

You’ll also need your mascara on hand, preferably a lash curler. Having some Qtips is a good idea as well. I strongly recommend using brushes instead of those hideous little sponge applicators that come with drugstore makeup. If you are serious about your feminization makeup, you’ll eventually want to invest in a set of quality brushes. For now, make do with what you have.

Practice Makes Perfect

You may not get the look you are going for the first time or the thirtieth. What’s important is that you remember that you are making me happy by trying. The smoeky look is a great one, because it is not precise. It combining and blending until you have careless elegance. Which is something that all feminized girls should strive for!

Watch this video, and practice.

When you have it right, it will be time to pick up the phone, and tell me your favorite part of the assignment. Aside from pleasing me, of course. That’s a given.

February 27, 2014
Feminization Assignment – Sitting Down To Pee

Feminization assignments can be such fun. While I enjoy a variety of them, I must confess that the ones that have a liberal amount of humiliation in them are among my favorites. After all, sissy phone sex sluts like yourselves need to amuse me, and your humiliation amuses me a great deal.

That said, I tend to *not* like, and therefore don’t give out, assignments that overly involve another unknowing party. I believe in consensual play, and that includes phone sex feminization assignments. So don’t expect that I will be sending you out to ask the counter girl at Macy’s which color of lipstick will enhance your lips as they stretch around a cock. That’s just not going to happen. Nor will you do such things on your own. You are to be well behaved at all times, and understand that your behavior is a reflection not only on you, but on your training. Which, in turn, is a reflection on me. So it would behoove you to mind your manners.

Small Feminization Assignments with Lasting Effects

I tend to enjoy handing out feminization assignments that have a cumulative effect. The death of your manhood…or what you believed to be your manhood…by a thousand tiny cuts appeals to me. One of my favorite ways of doing that is your new assignment. This is an assignment that you are expected to adhere to permanently.

Going forward, you are not allowed to stand up and pee like a real man. You now must sit with your pussy stick pointed downward between your legs when you urinate. I don’t care if you are in the privacy of your home, or in the middle of a crowd of 100 males, that is what you will do. Standing to pee is one of the things that outwardly differentiates males from females. Removing that from you pleases me. For most people, that means that 6 -7 times a day, that you will be reminded of what a feminized tool for me that you’ve become.

It makes me smile just to think of it!

December 13, 2013
Sissy Facials

In our final installment of your assignment for getting smooth, feminine skin we will be discussing the importance of moisturizing and sissy facials. Moisturizing doesn’t have to be a complicated process, though I know that the skin care counters at your local department stores can be daunting. Lucky you, you have me to be your guide!

Getting Beautiful, Butter-Soft Skin

The skin is the largest organ on the body, and for some of you tiny dick sissies, that is not saying much. However, since it is the largest, and the one exposed to environmental elements, you need to take good care of it to be properly feminized. Your moisturizing assignment is a 4 week process.

Week 1 – This week you will go to the drugstore, and get a bottle of baby oil. I prefer that you use baby oil with aloe vera and Vitamin E. ( Note: “I prefer” is code for do as you are fucking told. ) You will keep the bottle in the shower. After you are all nice and clean, you will squirt some baby oil into your hand, and rub it all over your body. You will not put any on your face, and you will not touch your sissy stick with slick, soft hands. Be careful! It can make the tub slick. Turn off the shower, and gently blot dry.

Week 2 – Now we’ll ramp that up a bit. You are to go to the mall, Sephora, or whatever is near you. Order online, if nothing is close. No matter how you do it, you are to get a jar of Lancome Nutrix Royal Body Moisturizer. Use it according to direction for one week. Then call me to discuss the merits of both forms of body treatment.

Week 3 – Time for a sissy facial! And no, greedy wenches, I don’t mean the cum kind. You haven’t earned that yet. You are to follow any recipe for a homemade moisturizing facial mask found here. Call me, tell me which recipe you used, why you chose it, and what you liked about it.

Week 4 – In your youth, you may have sat and watched as your mother or some other woman moisturized her face. This week, you will do the same thing. You are to buy yourself a jar of Perricone MD Face Finishing Moisturizer, and you are to send me a gift card to get my own jar. You can use this type both morning and night, and as you sweep it over your face, I want you to not only focus on what it feels like, but the femininity of the gesture. Arrange to give me a cam show of you doing it. When you do so, I prefer that you have your hair up in a towel like the cute image that I picked out for this post. And don’t forget what “I prefer” means!

December 6, 2013
Silky Sissy Skin

Ms Isabelle and I love when our feminized phone sex playthings know how to take direction, and you’ll earn extra credit by following these steps to get silky sissy skin. As you’ll remember, last week we talked about ways to exfoliate your skin. Today, our focus will be on hydration. After all, you want to look your best when we have you tilt your face upward to receive a nice, warm cum facial!

Hydration Tips to Achieve Flawless Silky Sissy Skin

As some of the more astute students might have gathered, your path to silky, feminine skin is awash in plenty of water. While you are probably familiar with the adage to drink 64 ounces a day, there is really not a one-size-fits all approach. You need to consider your activity level, weight, and environment. Web MD advises to drink half an ounce to an ounce of water for every pound you weigh. You will note that I said water, not fluids. So sodas, Starbucks, RedBulls or appletinis do not count. As a matter of fact, consider yourself banned from drinking those things. You need to make sacrificies to be a good sissy, and the money is far better spent on Ms Isabelle and I. Your health and skin will benefit, and so will we.

You will also hydrate in another manner. No, I am not referring to golden showers. I am talking about your nutrition. While moisturizing from the outside is important…and that will be the topic of our final installment next week…moisturizing from the inside is more important. This method offers a dual benefit. Not only will your skin improve, but your waistline will thank you as well.

That means your diet will be built around foods like avacados, fish, spinach and other darky, leafy greens, eggs, orange and yellow veggies, extra virgin olive oil, nuts, seeds, fruit, and cucumbers. Let your water do double duty, and infuse it with lemons or limes.

I love to micro-manage, so I would be delighted to work with you one on one on your diet and all aspect of your feminization. Face it, you really need me to help pull you into a presentable, feminized package!

November 21, 2013
Crossdresser Fantasies

Indulge your crossdresser fantasies with Ms Lily!

The weekend is almost upon us, and it’s time to escape into your crossdresser fantasies. To start that off, we are going to set the mood with a mini-feminization assignment. There are many of you, and each of you have your own life story to work around. So just do the parts of the assignment that you are able to do, and don’t get caught up in getting the details perfect. We’ll let you know when that is necessary, but for today’s purposes, you are going to relax, and enjoy your crossdresser fantasies.

Femininization – Surround Yourself in Scent

Though there are tons and tons of really wonderful perfumes on the market, we are going to turn to Mother Earth, and focus on the divinely feminine scent of lavender. Not only is the scent gloriously girlie, but the tiny blossoms are exquisite, and the color is certainly not going to be confused with anything that reeks of masculinity.

Need To Keep Your Crossdresser Fantasies Discrete?

If you aren’t able to dive into this fully, you can still participate. All you need to do is make one purchase, and carve out 15 minutes of uninterrupted time. You can do it in your car on the way home from work, if necessary.

I want you to stop at your nearest drug store, dollar store, etc. You are to find a lavender candle, and buy it. It doesn’t need to be a big one, since you’ll probably want to throw it away, and a votive will do splendidly. What’s that? You don’t know what a votive candle is? Go sit in the corner. You simply must know these things! How on earth will you see to decorating and entertaining?

Alright, back on track…as I was saying, you don’t need to purchase a large candle. But it *must* be lavender scented.

If You Can Explore Your Cross Dresser Fantasies in Private

If nothing in your life prevents it, you are to also buy a lavender scented candle. But you can buy a larger size, and more than one. You can also buy lavender body lotion, and lavender spritz for your sheets. If you have a tub, buy lavender bath salts or lavender bubble bath. If you shower instead, get lavender body wash, and I do want you to get the Ivory brand, if possible. This is a mini-assignment, not an excursion to Bath & Body Works.

Now, Time to Immerse in Your Crossdresser Fantasies!

Whether you are sitting in your parked car, with your candle held up to your nose or you are shoulder deep in a bubble bath, I want you to close your eyes. Inhale. Let the cares of the day slip away, and just relax into that pleasing, feminine scent. As you inhale, visualize the feminine aura entering your body, and weaving it’s tendrils through you.

When you are feeling loose, I want you to focus on what your most treasured crossdressing fantasy is. Maybe you’ve experienced it. Maybe not. All that matters is that it lives in your mind. See the details…whatever makes it uniquely yours…and keep inhaling that feminine aroma.

Relax. Enjoy. You’ve earned it.

And you want to share it with us. So pick up the phone, and let us know what your perfect crossdressing fantasy is!

August 1, 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
It’s Time to Step Into Spring, Sissies!

It’s time to develop some sissy style!

Now, it goes without saying that for some of you, having a cock stuffed down your gullet is the true extent of your interest in being feminized. But for others, the yearning is deep to embrace all things girly, and if you find yourself feeling as if that describes you, then this sissy assignment is for you!

I often hear people from all points on the feminization spectrum talk about how they feel like they missed out during their childhood years because they did not get to play with dolls. Barbie and her wardrobe are things that continue to pop up in conversation, and I can understand why. I know that I had a carrying case full of Barbie clothes and accessories. I couldn’t wait to burn through my allowance, buying the hottest trends.

Put on Your Pink Creative Hats – It’s Sissy Assignment Time

We’re going to do an on-going sissy assignment. From time to time, I will call on you to show me your creations. But you are to not just participate when I’ve directly requested it. You can consider this a sissy journal, of sorts.

Do you have your pink gel pens ready to take notes? Good girls! Now, this is what you will do.

a) Create a free account on Polyvore. This is a mainstream site, so do not create a username like “Greedy Gurl Slut”. Be classy.

b) Follow the Sissy Finishing School account.

c) Let your creative feminized energy run free! Your first sissy assignment is to imagine that you are presenting yourself to Ms. Isabelle and me for consideration to see if you are a sissy slut worth training. What would ensemble would you wear in an attempt to convince us that you are a sissy that is worthy of our time? Put together a set that follows the assignment guidelines, then leave a comment here with your username and the name of your set. Were you paying attention? Those comments are to go on this post. Do not rely on the comment section on Polyvore.

I expect to see some stunning examples of your notion of femininity, and your ability to follow through on future sissy assignments.

April 4, 2013