Sissy Finishing School

Category: Special Topics

Anal Training Fun

Anal Training Toy

For this anal training assignment you will need several toys in varying sizes. If you have access to butt plugs, you will need a small, medium and large plug for this training exercise. If you do not have access to butt plugs then find some items from around your house (i.e. candlestick, hairbrush, cucumber).

If you are a regular to anal training then make sure you are using bigger plugs for each part of the anal training segment. You may also want a rubber glove if you prefer for the warm-up portion of this anal training exercise. Last but not least, you will need copious amounts of lube.

Warm-up Anal Training

First you are to get into a comfortable position where you can reach back to your tight ass. If you want to wear a rubber glove for this part, put it on now. You will then cover your fingers in lube. Then you will massage your asshole slowly, inching one fingertip into your asshole, spreading the lube around. You will then start to sink you finger deeper and deeper into your ass, probing it gently as you lube up your tight hole. Once you have gotten use to the feeling of your finger, pull it out and re-apply a generous amount of lube to TWO fingers. You will then slowly and gently press those 2 lubed fingers to your tight hole, stretching it open as you press deeper and deeper.

For at least 3-5 minutes you will alternate between fucking your asshole with two fingers and stroking your prostate by curving your fingers toward your prostate while they are inserted deeply inside yous ass.

Once you are adequately stretched out and aroused it is time to move on to the first toy.

Part 1: Smallest Toy For Anal Training

You will start by lubing up the smallest of the toys that you have collected, making sure that it is slippery wet. Then you will squat down on the tip of your toy, feeling it stretch your ass open just a bit. Now slowly lower yourself onto that toy, letting it stretch open your ass as you take more and more of it. Once you have taken as much of the toy in your ass as possible, sit back to hold it in nice and deeply before slowly stroking your cock. Focus on the feelings of arousal as they surge through you body with each stroke; Focus on the feeling of the toy deep inside of you ass, possibly even touching your prostate.

Now bounce up and down just slightly, moving the toy only a few inches in and out at first. Spend 2-3 minutes bouncing on your toy in this fashion before you bounce up and down harder and faster. You should be sliding that toy all the way in and out now, really getting lost in the feelings of being fucked by this toy and slowly stroking your hard dick. Spend another 3-5 minutes fucking yourself in this fashion to open up your ass nice and wide for your next toy.

Part 2: Medium Toy For Anal Training

For the medium toy, you will follow the same instructions as the smallest toy. The only modification is that you will spend 3-5 minutes fucking yourself slowly and gently before you move on to the faster, more thorough fucking. Once you have really started to fuck your medium toy nice and hard, you are to spend 5-8 minutes fucking yourself in this fashion to ensure that you are loose enough for the large toy.

Before you move onto the biggest toy, you will lube up several fingers on both hands and gently use your fingers the literally stretch your ass as much as possible. Remember a little pain is normal, but do not push yourself to hard.

Part 3: Largest Toy For Anal Training

Now take the largest toy and lube it up really good, making sure that it is super slippery and wet for your ass. You will position yourself over the toy and slowly lower yourself onto it, inch by inch. If the stretching becomes to much at any point, stop and wait for 1-2 minutes before proceeding to take more and more of the toy.

Once you have taken in as much of the toy as you can, you are to rest there for a full 2 minutes while you jerk and stroke your cock for me. After your resting period, you will start to slowly fuck the toy inch by inch, being careful to keep as much of the toy in you as possible for the next 5 – 8 minutes.

As your arousal peaks, you will start to fuck the toy much more aggressively. You will fuck it hard, fast and taking it in and out as much as possible for the next 5-8 minutes while you jerk your cock at the same time. You should be bouncing on your toy hungrily till you cum all over the place. Now, clean up your cum with your tongue if you are adventurous and let me know in the comment section how much fun you had with my anal training assignment.

Until later…….

Ms Isabelle

October 14, 2013
Ass Worship Phone Sex

Look at my picture, and admit to yourself how much you want to have ass worship phone sex with me. Go ahead. Slide your eyes just to the left, and look at my tantalizing ass. If I do say so myself, it looks delectable in my morning work out clothes. I think that would be a fun way to make you start your morning. You’d have to kneel in panties, holding a towel for me, and watch as I stretched and pulled my body right in front of you…

lower back arched so that my ass is so very, very close to your face.

You know I am going to torment and tease you, sissy bitch. Your panties are going to get tighter and tighter, and you’ll feel a spot of dampness on the front of them. You’ll want to lower the towel so that I won’t know the effect that my luscious backside has on you, and that I won’t be able to tell how much you want to worship my ass.

Silly sissy. Of course I know.

That’s the fun of it.

I Know Exactly How Much You Want to Have Ass Worship Phone Sex with Me

I love taking that knowledge, and using it against you. I love making you salivate, your tongue quivering with desire. What will it be today, hmmm? Will I make you stretch out on your back, while I lower myself and hover out of reach? Will I lower further, smothering you with my orbs of glory, while you leak in your panties and inhale as deeply as you can, my scent permeating your very being?

Or will I s-l-o-w-l-y pull off my clothes, and then make you beg for it? Make you beg to put your sissy tongue against my flesh, and flick your eager tongue against me?

Which will it be, sissy?

October 4, 2013
Sissy Panty Liner Training

I like enforcing sissy panty liner training for a variety of reasons. First and foremost, I like to humiliate feminized gurls like you. I also know how often some of you are making messes in your pretty panties. That simply won’t do, so it’s time to remedy that.

First things first…you all do have panties, correct? I cannot fathom that you would have read the writings of Ms. Isabelle and myself this long and not have bought panties. But if you don’t have some, get them now. Consider that an assignment. If you are resistant to wearing panties, all the better. Don’t think that you will get to slide by with some utilitarian pair. I want you to buy something nice and feminine. I particularly like these Betsy Johnson panties, so getting those and giving me a cam show with you in them will earn you extra stars. Sending Ms. Isabelle and myself Amazon gifts cards to buy our own pairs will earn you even more stars.

Feminization Shopping Assignment

Alright, now that everyone has at least one pair of panties, it’s time to begin your sissy panty liner training. You are not going to skate by and order these online. No, you are going to to your local drugstore, and you are going to buy panty liners to put in your sissy panties.

Note that you are not to just sweep down the feminine hygiene aisle, and furtively knock a box of panty liners in your cart. That wouldn’t be any fun for me at all, sissies, and when in doubt, I refer you back to the rule about this always being about my fun. No, darlings you are going to stand in the aisle and carefully, word for word, read the description and product benefits of three different brands of panty liners. Aloud. No mumbling. At some point during your sissy consumer research, you are to tilt your head to the side, visually examine the products in front of you, and bemoan the fact that you don’t know which brand is best to absorb the mess that you make in your panties.

Then you are to call in and tell me about the experience. Bonus points will be awarded to anyone that surreptitiously takes a video of themselves doing this, and posts it online for my amusement. Double bonus points for anyone who calls me while they are doing it.

September 26, 2013
I Want To Emasculate YOU

I Want To Emasculate YOU!

Time For Me To Emasculate You

I love to emasculate my submissives. Many of you may wonder what it means when a Mistress decides to emasculate one of her submissives. Here is the definition of the word emasculate for those that are not familiar with that form of control or humiliation.

Emasculate : To deprive of strength,vigor or spirit; weaken. to make (a man) feel less masculine : to deprive (a man) of his male strength, role, etc. to make (something)(someone) weaker or less effective.

There are many ways that an experienced Humiliatrix such as myself can emasculate you and I want to share a few of my favorite ways. Let me start with the most obvious ways to emasculate you.

Ways For Me To Emasculate You

First of all, you will be made aware of how little your opinions, job and money matter to me. I have no desire to make you feel good about your job or how much money you are making. I also do not think you have the ability to make good decisions, which means that your opinion is of no consequence to me. You are just a pathetic loser that is lucky to have a Mistress like me that will agree to allow you to serve me.

Secondly, I will be in charge of your every move. You clearly make such bad decisions. Only a strong and powerful woman like me could help you get back on the correct track. I will be in charge of your daily schedule, your bank account, and your free time. You will always remember to ask for permission before doing something that you want to do and that my needs ALWAYS come first.

Another obvious way to emasculate you is to make you conscious and aware of how small your cock is in comparison with some of my other lovers. This will mean that you have to start wearing ONLY girly panties to cover up your little clitty. You might even get to wear your new panties as I fuck my well endowed BBC lover in front of you!

Are You Ready For Me To Emasculate You?

I will slowly transform you into a complete bimbo sissy that will desire to be a cocksucking slave as you completely loose every ounce of your masculinity. Losing your masculinity is the ultimate way to emasculate you my little pet. You will learn to move, act and think just like a sissy. You will put the needs of your lovers far above your own and be exceptionally grateful for any pleasure that you earn.

Those are just a few ways in which I can emasculate you. If you’d like more emasculation and humiliation, give the Mistresses at Sissy Finishing School a call. I can’t think of anything I rather do on this lovely fall Monday than emasculate you!

Until then………

Ms Isabelle

September 23, 2013
Cam Shows With Your Sissy School Mistress

I Love Watching Sissies On Cam!

Bouncing Sissies On Cam

I have a special kind of love for sissy boys that love to fuck themselves on cam for me. The connection that we can share during this experience is much deeper than you could imagine. I honestly just can’t get enough of watching sissies bouncing on their dildos, and carrying out humiliating tasks on cam for me!

Why Do I Want To Watch You On Cam

Well, the obviously I get to see that you are actually doing the things that I have asked of you. I get to see you wearing that slutty lingerie as you bounce up and down on that nice hard dildo for me. There is nothing better than the confirmation that a sissy boy is doing JUST as his sissification Mistress asks.

Watching you on cam makes me feel even more powerful as you subject yourself to some of the sluttiest tasks; Including you sucking your big black dildo, bouncing up and down on your favorite dildo, and making you slurp up all your jizzy mess!

In addition to the power I feel from watching you on cam, I love the way that it emasculates you further as you bare all to me during our sissy phone sex sessions. You become completely vulnerable to me as you expose yourself to me during your cam fucking sessions.

As you are vulnerable, I am able to solidify my control on both your conscious and subconscious mind. I am able to take complete control of you and capable of shaping your desires as you give in to my instructions and commands.

Are You Ready To Perform On Cam For Your Mistress

Lastly, I love being able to watch your body and face react to the orders that I give you as you bounce up and down on your dildo. I love watching the twitches of arousal that run through your body as I purr soft, dirty things into your very alert ears. There is nothing like seeing the impact that I can have on a person while I am watching them on cam. Feeling excited now? Then you need to drop me an email and set up an appointment for me to watch you on cam.

Until then…….

Ms Isabelle

July 29, 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
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
Being Devoted To Your Sissy Phone Sex Mistress

Show Your Devotion To Your Sissy Phone Sex Mistress

Devoted To Your Sissy Phone Sex Mistress

I know that deep down that you want to become a loyal and devoted sissy phone sex slave to a gorgeous, powerful and fashionable sissy phone sex Mistress! I have many years experience in training and shaping sissy boy’s into the very best sissy that they can be.

It is of the utmost importance that when you report to me with pleas that I teach you to become a true and devoted sissy that you are 100% serious. I do not have time to waste my precious minutes with sissy boy wanna-be’s.

Your Sissy Phone Sex Mistress Deserves To Be Spoiled

A sissy phone sex Mistress such as myself deserves to be spoiled for all the time for effort that I put into my sissy slaves. I work exceptionally hard to transform men into sissies; some men that approach me are pathetic and reproachable, while others are secret sissies that own fortune 500’s in their panties.

I have become accustomed to being showered in devotion, honesty, loyalty and lavish gifts and tributes. I expect nothing less from each and every sissy phone sex slave that I train!

There are many ways that you can spoil your perfect sissy phone sex Mistress. You will learn to worship my body in various ways from giving me pedicures and massaging my perfect, sexy body to sucking on my dirty toes after a workout or doing my laundry. You are nothing more than a perfect sissy maid created by me and trained to please his sissy phone sex Mistress.

Lavishing Your Sissy Phone Sex Mistress

You will also be allowed to tribute to your sissy phone sex Mistress in the forms of gifts and lavish cash tips. This will be considered one of the greatest honors to bestowed upon you, allowing you to spoil me in every single way. You will find immense pleasure in showering me with gifts and tributes as you earn the right of passage to become my full-time sissy phone sex slave.

Are you ready to learn to be the best sissy that you can be, while enjoying spoiling your sissy phone sex Mistress?

Until later……

Ms Isabelle

June 28, 2013
SPH- Small Penis Humiliation

Discovering Small Penis Humiliation

Small Penis Humiliation

Did you recently just discover that you, in fact, do have a very small penis? Perhaps, girls were nice to you during college, but when you attempted to be with a real woman, you were laughed at and then informed that you are just another small penis humiliation loser? I know exactly how a small cock loser needs and deserves to be treated.

The first instinct you may discover is that you are having is the urge to wear woman’s underwear. A pair of pink, silky panties. Since you only possess the equipment that is the equivalent of an enlarged clit, panties will be the perfect thing to start your transition into a full-time (SPH) small penis humiliation phone sex lover! We will hide your tiny penis in the perfect pair of silky, pink panties that will make you feel much less like a man and more and more like a prissy, sissy faggot.

Little Dick Losers Like To Suck Cock

The next instinct you are going experience is the urge to suck a nice big cock. Some men have fantasies about tranny cock, while others dream of sucking a real man’s nice big fat cock. Either way you will be sucking cock like a good little panty phone sex slut. I will teach you how to suck those nice big cocks that dwarf your clit in comparison.

You will start slow, taking the cock into your mouth inch by inch, working your hands on the exposed cock and balls. Once you have become more comfortable with that you will learn to deep throat that throbbing hard cock! As a panty phone sex slut and small penis humiliation loser, it is imperative that you learn to suck cock! Then, once you master the art of cock sucking, I have something else in store for you but we will save that for later.

Small Penis Humiliation Turns You Into A Perfect Little Cocksucker

During your small penis humiliation sessions, these are just two of the main steps to teach you to become a proper panty wearing loser for your SPH Mistress. I am extremely experienced when it comes to transitioning you into a completely emasculated little dick loser and a good little sissy cocksucker.

Now hurry up and grab your panties and get to class. I have my ruler waiting to measure you at the door and you could be my “small penis humiliation loser” of the day and I have something special in store for you!

Until then………

Ms Isabelle

June 12, 2013