Sissy Finishing School

Author: Ms Lily

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
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
Sissy Strapon Training

While I do get enjoyment out of seeing sissy bitches trained to pleasure cock for my amusement, sometimes I want to take matters into my own hands…or my own hips, and just fuck you myself, which means sissy strapon training. Sometimes if you want the job done right, you just have to do it yourself. Not to mention I like to pop sissy cherries. I like doing that before I introduce them to the next level of being degraded via penetration by a real man, if that is my plan.

Sometimes they are surprisingly good fucks who take very well to their sissy strapon training. I’m not sure what I enjoy most. Part of me likes it when your whore hips lift off the bed in eager anticipation to meet my every thrust. Part of me likes it when tears roll down your cheeks as you protest that you just can’t take a cock as big as mine.

Assume the Pussy Position for Sissy Strapon Training

Your strapon training will include multiple positions, all dependent purely on my mood of the moment. I know that for some of you, being flat on your backs with your legs up in the air is the ideal I don’t care. What matters is my ideal, and I may well want you up on your hands and knees, with a mirror positioned in front of you, so you can look at yourself while I make you my bitch.

Won’t be denying the truth of what you are then, will you?

I may decide that you’ve been lazy, and that you need to show me how eager you are for your sissy strapon training. That may mean that I am the one laying flat on my back, with my cock pointing due North, and you have to climb on top, and lower yourself until your sissy pussy is desperately grinding away, hungry for what I can give you.

Sissy strapon training is one of my favorite things to do, especially when I combine it with chastity and ruined orgasms. As you read this, you may not think that you’ll beg for my cock.

But eventually…

you will.

July 25, 2013
Mouth Soaping for the Insolent Sissy

I’ll make you beg, bitch.

In an ideal world, all sissies would be demure and well behaved, and I would never need to do any sissy mouth soaping. But as we all know, the world is not an ideal place, and therefore, from time to time, a good old-fashioned mouth soaping is in order for the insubordinate sissy. My theory is that if you act like a willful child, that I will treat you like a willful child. I will demean you, and I will make you suffer. Then, when you are on your knees whimpering for forgiveness, and the honor of serving me again, I’ll either decide you’ve had enough, and send you off to wash your tear-stained face, or I will decide that you need a hearty dose of castor oil on top of your mouth soaping.

The choice is really yours. It all boils down to how well you take your medicine.

Liquid or Bar – Which is Most Effective for a Sissy Mouth Soaping?

Sometimes a bar is more appropriate. If the offense is relatively mild, a comparable soap, like Ivory may be in order. If I’m annoyed, you may be opening your mouth for a soaping of a more potent variety, a la Lifeboy. It’s almost like pairing the right wine to the correct meal, and cleansing the palate takes on an entirely different meaning.

Liquid soap can be fun too. I find it particularly effective for rubbing furiously into the taste buds. Don’t even think about retching during your sissy mouth soaping! That will call for sterner measures, and you may find that it turns into a very vicious circle.

One that I am destined to win, each and every time.

July 18, 2013
The Ultimate Sissy School

We love our sissy school sissies!

“Thank you for creating the ultimate sissy school.”

Those were the words I heard from one of my sissy school phone sex callers last week, and it truly made me beam. So with that in mind, I wanted to hit pause for a moment, and say thanks to all of you that have visited our hallways, picked up the phone, called in for assignments, etc.

When Ms Isabelle and I decide to do something, we don’t half ass it. I know that some of you that have been sent to detention will find it hard to believe, but we hold ourselves to higher standards than we do you. After all, we are dominant, beautiful, superior women, and you…well, you’re sissies. There’s an entire rainbow of things that you may be in to or ways that you may view yourself and your place in the world. If you’ve talked to us, you know that we get that. But in it’s simplest form, you are all sissies And even though we *are* dominant, beautiful, superior women, it is to you that our efforts and this sissy school are dedicated.

Why We Are the Ultimate Sissy School

It’s no secret that there are a plethora of places that a sissy can go for phone sex. But what makes us unique is that we are not characters…we are who we are. Neither of us is some woman who read a few stories on Literoitica and decided that she could try to bluff her way though sissy phone sex. We both have actual experience to back up the talk, and though we can be exceedingly sadistic at times, we can also be nurturing, caring, and empathetic.

In short, we aren’t someone’s cartoon notion of what it means to be a dominant woman. Just like you, we are complex beings, with layers and corners and sunshine and scary places. That is what helps us connect with our sissy callers on a level that other places, quite frankly, can’t hold a candle to.

That is what makes us the ultimate sissy school.

Thank each of you for your support thus far. Whether you are Gold Star VIP student, or you stop by to read the latest and vote for us, we appreciate what you give. It makes us committed to remain on top of our games, so that we can give you the time of your life.

Now put your plaid skirt on, and come write on the chalkboard 500 times…I love Sissy Finishing School!

July 15, 2013
Sissy Pain Sluts

I’ll make you beg my flogger, bitch.

I don’t have a live-in sissy, but I do have a few that I torment locally, and a couple of them more than most. In addition to being a cock-loving sissy slut like many of you, she is also a pain slut. Pain slut sissies have a special place in my heart, because they can be taught to beg so prettily. And that’s just what I had this wretched harlot doing this morning.

I have an adorable, cozy little house that is just fit for a princess. It is fair to say that I am a neat freak. It’s also fair to say that I have better things to do with my time than to clean. I see no reason to employ a housekeeping service when I can be knee-deep in sissy maids at the snap of my fingers. The only problem with that is that sissy maids like to be used, and I’ve been in a rather sadistic mood lately. Of course, that means that I’ve charged a sissy that is not inclined to serve in that manner to serve in that manner. She knows better than to grumble, but I still take pleasure in the fact of knowing that she doesn’t like what she’s doing, but that she does it anyway.

Because I said so. No other reason is necessary.

A Sissy Pain Slut Gets Her Just Rewards

I’m a sadistic bitch at times, but I tend to be fair. At least when it pleases me to be. After I did inspection this morning, I found that I was in a mood to be generous. I’d gotten a good night’s sleep, and woke up to a sparkling house. So I decided that some rewards were in order, and I sent sissy to fetch one of my suede floggers.

She scurried off eagerly, and I had to laugh when she returned. I could see the need gleaming in her eye like stars strewn across the velvet black of a night sky. I made her wait for 45 minutes while I took a sissy phone sex call. Though my focus was on my caller, I was aware of her presence…just standing there, waiting. Now and then she’d dart out a finger, and run it over one of the strands of the flogger.

When the call ended, I started off by making the sissy pain slut kiss my bare toes. She had to kneel down to do this, of course. I amused myself by letting the flogger idly dance over her exposed spine while her lips gratefully pressed up against my French tipped pedicure.

Then I sat down for awhile, and made her beg. It’s such a lovely thing when someone begs you to hurt them.

Finally, I did. I picked up my flogger, had her assume the position of the day, and I flogged her sissy back and her sissy clitty until my arm was too tired to swing it anymore. I settled back and took a couple more calls then, and made her keep her position for another hour. Alas, she got a cramp in her calves, and the end result is that she’ll be back tomorrow to clean out the garage. If she’s lucky, I’ll let Kali’s Teeth sink into her worthless sissy clitty, and we’ll dial that pain up a notch.

July 10, 2013
Sissy Phone Sex 101

Bounce on your toys, bitches

One of the things I enjoy most about being a distant dominant that engages in sissy phone sex is making you play with sex toys. I love the elements of controlling what toy you’ll play with when. I love giving assignments so that you stay connected to me when we are not in session. And I love establishing who and what you are…a sissy fuck hole that is to be used as I see fit.

Are Sex Toys Necessary for Sissy Phone Sex?

It is entirely possible for a sissy to not have sex toys, and still provide me with amusement. However, I do prefer that we have some accessories to play with. While I love fancy toys like prosthetic vaginas for sissies, I can be content doing something as mundane as watching you practice your deep throating techniques with a banana on Skype. The important thing is really what is taking place for both of us mentally. I’m getting the rush of controlling you like the cunt-for-use that you are. And you are getting a pokey place in your panties from getting to serve me. That, pets, is a win/win situation. But only one half of that equation really matters, and that’s the half where I am enjoying it.

What’s In Your Toy Chest?

What kind of toys do you have? If you’ve yet to acquire any, I would love to shop with you, and pick out exactly what I want you to have. If you’ve already got several, well…more is better. But I don’t have to tell you that, do I, greedy girl?

Get out your toys, and ring me. Let’s play.

July 3, 2013
Panty Boy Phone Sex Challenge

Are you the biggest panty boy roaming the hallways of Sissy Finishing School?

I had a really delightful time with a new-to-me panty boy phone sex caller recently. His pre-call questionnaire said that he identified as a panty boy. Once we had emailed a couple of times, then talked, I could see that he was certainly telling the truth!

Granny Panties Are His Panty Boy Fetish

We’ll call this caller Mr. PB. It’s certainly a fitting name. He has 150 pairs of panties. That’s right..150. We are not talking about your garden-variety panties either. Mr. PB has a fascinating back story, and due to it, he developed a love of granny panties. What I have seen of his collection is an exquisite assortment of custom-ordered, hand-crafted panties that would cause many a panty boy to tear at their hair in envy. In addition to their feminine prettiness, some pairs are made of a vintage fabric, that ties in with his story. At 150 pairs, I think it is safe to say that Mr. PB has moved from the realm of Panty Boy to Panty Fetishist.

What’s In Your Panty Boy Collection?

The more I thought about the sessions that I had with Mr. PB, the more I became convinced that he had the largest collection of panties of any panty boy that I had ever talked to. Since I love challenges, that my mind took the logical next-step, and wondered “who has more?” Is it you?

The challenge is on! I want to know if a panty boy exists that has more panties that Mr. PB. If so, I want to see pictures, and I want to hear your back story. I want to know how you became the man that can’t wait for his alone time, so that he can slip into the satiny delight of a perfectly fitted pair of panties, and admire himself in the mirror.

Tell me.

June 19, 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