Sissy Finishing School

Author: Ms Lily

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
Get Locked in Chastity

Roses are red

Violets are blue

I will take your orgasms

Away from you

**
Happy Valentine’s Day, playthings! Did you enjoy yourselves? Perhaps you had an explosive orgasm. Or two. I know I certainly did!

If you did, I hope you really savored it. If you didn’t…well…you may live to regret that. Because Spring will soon be in the air, and that generally means that as hemlines rise, so do your libidos. Which, of course, is the perfect time for you to get locked into chastity for me!

Reasons to Get Locked in Chastity

For the uninitiated, it is often difficult to understand why someone would get locked in chastity. Which is actually a pity, because chastity play is one of my favorite things. Let’s take a look at the Top 5 Reasons why it’s a good idea to get locked in chastity, shall we?

#1 – Refer back to it being one of my favorite types of play. Pleasing me should be the ultimate goal always.

#2 – When you get locked in chastity, you no longer have control. That is submission, and it’s incredibly freeing. It can also be incredibly difficult. Challenging yourself is good.

#3 – Getting locked up means that the world takes on a type of intensity that it never had before. You become acutely aware of sensation, time, and space.

#4 – Edging becomes mind blowing. You may *think* you’ve enjoyed standing on the edge of orgasmic bliss. But you haven’t experienced anything until you are doing it under my direction, when I’ve unlocked you for playtime.

#5 – When and if I allow you to release, your world will be forever altered. You may doubt my word as you read this, but trust me….you will come to crave the state of being chaste, and will hope that I will deny you longer. Why? So you can continue to please me, and because with each passing day, the power of the denied orgasm builds. When I unleash it, I will own you for all time.

I can’t think of a better reason, can you?

PS…If you’ve been trying to reach me for a session, please see my Schedule page for updates.

February 15, 2014
Project Runway – The Stylish Cross Dresser

If you aren’t already, now is the time of year when a cross dresser really must bring her game face, and transform from a mere mortal into a stylish cross dresser. Awards season is in full swing, and the New York Fashion Week (NYFW) is underway, so now is not the time to be frumpish and dowdy. Not that there is ever a time for that, but especially not now. It’s time for you to tap into your inner fashionistas! And once you have, of course, you must share with Ms Isbaelle and me.

Expressing Your Stylish Cross Dresser Self

Odds are, you don’t have an invitation to any of the shows. And if you do, you need to FedEx it to me post haste. But assuming you are not fashion royalty, and you won’t be sitting in the front row of Lincoln Center, you are going to have to be creative, and let us see what kind of panache you have. I’ve got a few ideas, and you are free to take them and embellish them, or come up with something to dazzle us.

Whatever approach you take, your assignment is to come as close to creating a red-carpet or runway experience as possible. You needn’t drop a lot of cash for this project. You can take a note from Macklemore and Lewis, and pop tags at your local “Thrift Shop“, if you are going to actually dress the part.

That won’t be possible for all of you, and that is fine. You can make a collage of what you’d wear, and send a picture of it in. You can create your favorite ensemble at Polyvore, and share it with us there. You can draw your vision, paint it, or write a story, chock-full of rich detail, describing what you have on as you strut your stuff. Whatever means that allows you to fully immerse in your stylish cross dresser self is fine. You just need to share the outcome. And you need to remember that we love swag bags, so do your part toward filling ours to the brim. In the immortal words of Madonna…”Express Yourself!”

February 8, 2014
Be My Sissy Cheerleader!

Though I appreciate the beauty of real women cheerleaders, they don’t amuse me like when someone wants to be my sissy cheerleader. That said, some sissy cheerleaders can be both beautiful and amusing. The two things are not contradictory in all cases. Perhaps they won’t be in yours when you complete this assignment.

Sissy Cheerleaders in Service

I went to a small gathering for the AFC Championship game. As some of you know, I do not currently have a live-in sissy, though I have several that I toy with when the mood strikes me. However, my dear friend in another state does. She has 3 actually, and she was the one playing hostess to the gathering. At first the sissies were demure. They gathered everyone’s coats, served food and drinks, and just generally saw to our comfort. Which, by the way, is not bad work if you can get it. I know sissies that would give their eye teeth to be in service to a handful of dominant, beautiful women.

Anyhow, this pattern continued for awhile. With roughly 5 minutes left in the first half, the sissies asked for permission to be excused. They needed to prepare themselves to entertain us for our own personal half time show. Trust me, though I like Bruno Mars, you won’t see anything like what I saw that afternoon during this year’s Super Bowl show! Their was much flouncing in pleated skirts, lots of pompom shaking, and something with a megaphone that left me wincing as I watched. That was immediately proceeded by gales of laughter.

It’s Your Turn Now

I know that some of you have been trying to reach me, and now that I’m back home for a bit, I’m ready for you to amuse me on cam. What better way for you to do so during this footballabulous time of the year than to dress up like a cheerleader and give me your best cheer? I can’t think of a better way, and as you should all know by now, what I think is what matters. I want to see some ponytailed strumpets shaking their moneymakers for me in fine cheerleader style.

So try to catch me, or mail for an appointment, and do your duty. Amuse me.

January 24, 2014
Prepare Me for a Real Man, Sissy Cuckold

It is Friday night, and that means it is time to prepare me for a real man. You didn’t think I was going to stay home with you, did you silly sissy? Not on your life! Not when I can enjoy my stud *and* turn you into a sissy cuckold. It is double the pleasure and double the fun. At least for me, and that’s what matters!

First Steps in Preparing Me for a Real Man

The first thing you need to do is thank me for the honor of being allowed to prepare me for a real man. You are very fortunate that I am giving you the opportunity to please me in a role befitting you. Let’s face it, there is only so much a sissy is good for, so you should take advantage of every single time you are afforded the privilege of pleasing me.

Next up is to slip into a bra and panty set that I will personally select for you. It goes without saying that you should be smooth before you don any lingerie. Though sending you for a waxing is a personal favorite, I’m not overly finicky when it comes to the “how” of your smoothness. I just want it done. So see to it. And don’t think that I won’t notice the damp spot on the front of your panties, as I most assuredly will. I’ll call you out on it as well. It gives me pleasure to point out how you are my emasculated bitch, and why it is necessary for you to prepare me for a real man.

Next Up – My Bath and Lingerie

Once you are properly attired, and I’ve inspected you, it will be time for you to see to my grooming…head to toe. I want you to drink in every inch of what you won’t be getting tonight, and what a real man will. Go ahead, sissy. Feast your eyes on me. Look at my body as it glistens in the bath water. Towel dry me. Rub body lotion over curves that are otherwise forbidden to you. Then fetch the white bra, panties, and stockings that I’ve laid out. As you go to get them, think about what it will look like when his hand jerks those panties downward. Think about how the moans will sound as they pour out of my throat when he first slips his finger inside me. Allow yourself to imagine the unimaginable, and think what it must feel like to be him, and have my pussy clench around his cock as it fills me.

Think about it, sissy. And let that spot in your panties grow damper and damper.

January 4, 2014
Become a Better Sissy

With the new year rapidly approaching, your thoughts should turn to resolutions, and how to become a better sissy. It’s time for you to put on your thinking caps, and determine what type of goals you have for self improvement. These goals can either be sissy feminized goals, or they can be more mundane. Either way, for increased likelihood of actually meeting those goals, you need me as your Sissy Life Coach to help you become a better you.

Tailor Made Programs to Help You Become a Better Sissy

Now though the end of January, I am taking applicants for my 2014 Build a Better You course. All applicants must have a stated goal to work toward. As mentioned above, it can be kink-related, or it can be as simple as getting you into shape. The curriculum for each student will differ, and be individualized to what each of you needs to become a better sissy.

Course length will also vary depending on the goals, with a 4 week minimum. Someone who has a stated goal of working up the courage to go real-world panty shopping will have a shorter course than someone who wants to suck a cock on cam for me. Generally speaking that is. Some of you are salivating for the opportunity to hear me give the command to suck. Those students will be on the fast track to course completion!

Course Criteria and Application Process

In order to be considered for acceptance into the program, you should prepare for, and agree to the following:

1) Know what you want to work toward. I am giving you the rare opportunity to think for yourself as opposed to me telling you what to do. That part will come during the implementation phase.

2) Contact me to schedule a 20 minute minimum call to go over your goal(s). During this call, you should not only be able to communicate your goal, but any thing that I need to know in order to craft your coursework. (eg, you are married, etc)

3) Be prepared to complete assignments outside of our sessions. The length of time necessary for these will vary depending on your goal.

4) Understand that you are committing to a program of at least 4 consecutive weeks in nature. More intensive coursework is available after the 101 level, if you desire it and if I enjoy your company.

5) Commit to a minimum of one 20 minute session per week for the duration of your program. Those sessions will be scheduled in advance.

So put on your prettiest panties, curl up on the couch with your legs tucked under you, and give some serious thought to what you want to achieve in 2014. Together we can make it happen!

December 28, 2013
Naughty and Nice Feminization Phone Sex

Since this will be the last time I post before Christmas, I thought it was time to check in and see who was on the list for naughty and nice feminization phone sex. There are a few rare sissies that can be on both lists. However, most of you will either need nice, soft, sensuous-yet-controlling feminization phone sex, or you will need naughty, strict, stern, and no fucking around feminization phone sex.

Luckily for all of you, no matter what your kink, Ms Isabelle and I have it covered. We *are* your Christmas gifts.

Nice Feminization Phone Sex

All true gurls who love having a woman gently dominate them, or provide guidance on their transformation journeys will love sensual sissy phone sex at the Sissy Finishing School. Ms. Isabelle and I are Natural Born Cock Teasers. What that means, my little strumpets, is that we know how to croon and cajole and have you quivering in your lacy panties that are ever-so-damp in front. We know how to make you beg for more, and how to become irresistible sirens that you need to return to time and time again. You’ll love the way that we wrap you around our well-manicured pinkies, and you’ll find that you become very devoted to us and our pleasure.

Naughty Feminization Phone Sex

Naughty feminization phone sex junkies have a special place in my heart. It’s not that I love you more than your sensual-loving counterparts. No, it’s not that at all. It’s just that fucking with you gives me a different type of pleasure. I love using your mind, body and soul as a canvas to paint my sadistic art on. That sadism can take many forms, ranging from simple denial to smiling down at you while the heel of my red patent leather boots sinks into your pathetic sissy sack. Ms Isabelle and I have shared more than a few of you, and that is also another thing that is fun…when you have not one, but two highly skilled, very wicked women in cahoots, tormenting you at will.

It puts a smile on my face just to think about it!

So whether you like your feminization phone sex to be naughty or nice, you’ve found what you are looking for.

Surrender to our power.

December 20, 2013
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