Sissy Training Assignment from Mistress Courtney


For a phone session with Mistress Courtney call 800-356-6169



I can hardly believe November is here.  As the year comes to a close, it’s time to get reflective.  I’m sure this has been a year of many blessings for you all. Just being a sissy is reason enough to be grateful, isn’t it?  I mean, sissies rock!  And you are among that elite group of people known as sissies.  So smile!

And, I think it would a really nice exercise for you to sit down with your computer, perhaps light some candles, some incense, settle in with a nice glass of cabernet sauvignon, and write down all of the things that you are thankful for.  Perhaps you finally got to have your day of beauty at a salon?  Maybe you got your first bra and panty set.  Or, have you found a Mistress that really gets you?

Finally got up the nerve to dress en femme and go out shopping?  Maybe you have new friends to get girlie with and go shopping?  Have you lost some weight?  Maybe gained some weight in all the right places?  Really search your mind for all of the things, people, experiences and events that have helped you to embrace your sissy-ness..  Maybe you are grateful for the community of sissies here at Sissyville and at Sissy School?  So many of you were isolated before the internet really took off.   Many of you have experienced feelings of loneliness and isolation before finding the Mistresses of LDW and the sissy fans of LDW.  You see there!  There is so much to be grateful for.

Well, well, well. Halloween is fast approaching! I know this is the quintessential holiday for all of you budding sissies, is it not? Everyone almost expects men to dress as women for Halloween. It’s the one day you can dress in drag, and hit the town and no one really seems to care. Of course, for you sissies that are into the humiliation of being a sissy, that aspect of it is kind of a bummer. But hey, you get to waltz out your front door in broad daylight for all of the world to see. I think that’s a pretty cool deal. So, what is my assignment exactly? Well, if you are planning to dress for Halloween or for a Halloween Party, I want you to really go all out. Don’t just buy an off-the-rack costume from your local superstore. Really put some thought and planning into it. Now, you are going to have to work hard and fast, since Halloween is just around the corner, but I know you sissies can do it! Go as someone really glamorous. Marie Antoinette, Pussy Galore, Emma Peale, Cat Woman, heck, even Wonder Woman! I want you to really get into it. Get your glitter and your glue and go to town making your costume if you can’t find the elements that you need at your local used clothing store. Be a butterfly or a princess; the ideas are endless! Then, I want you to…

Okay sissy boys and girls, here is your latest lesson from Empress Cassidy.  Today we are going to talk about dressing to pass, and not to look like a drag queen.  I know the drag queen over the top look seems like fun and stuffing your bra with those 38 EE falsies seems like a great idea, but trust me, no one is ever going to think you are a real girl if you are at the mall in bright blue satin hot pants and tighter-than-skin top with boobs about to topple you over.  No matter how nicely you do your make up or how much you spend on that wig, if you look like an escapee from Las Vegas you will never ever pass.

So, let’s focus on what you should be wearing. Every Mistress prefers her sissies to dress a little differently, and every sissy has things they like and don’t like, but you have to learn, just like REAL girls do, to dress for not only the occasion but the place. If you are like me and live in Southern California, then you know that we dress up to go shopping. A nice silky wrap dress and some sensible heels to go with your Chanel bag will be perfect.  Your hair should be straight and smooth, and jewelry is a must!

Now if you are in New York City, you might get to be a little funkier and more trendy, in Florida, you can wear khaki shorts and a cute bright colored blouse with leather sandals, while in Texas, jeans work wonderfully with some boots.  Even in the mid-west you need to check by the weather and what everyone else is wearing.  You do not have carte blanche to wear whatever you like no matter what. Not if you want to pass as a girl. So, sissies, head down to the mall, dressed down and check out what the other girls are wearing, then pick up some sensible pieces and get yourself dressed up.

I promise you’ll have a lot more fun skipping through the mall in something cute and making all the boys wonder than you do tottering around on those 6″ heels. Then, I want you to…

Hello sexy sissies! I have a really fun assignment for you to do today! I want you to locate a full service salon in your area. For those sissies that may be unaware as to what exactly I mean by a full service salon; let me clue you in. A full service salon is one that does everything-hair, nails, facials, body waxes, makeup, anything regarding beauty.

Now, I want you to get all dressed up, this is your dress rehearsal. Put on your finest of everything! Your finest lipstick. Your finest panties and bra. Your finest stockings and garter belt, or, if you prefer, your finest pantyhose. Your finest dress, or, your finest skirt and blouse, whatever makes you feel fine! I want you to pick out your finest jewelry and be completely bedazzled, got it girls? Then, I want you to call up that salon and pose as a masculine guy while dressed in your finest sissy wear.

Tell them that your sweetheart, whose name is ______________ (and then be sure to give them your sissy, girlie name) is having a birthday, anniversary, just got a promotion, whatever, and that you want to treat her to a day of beauty. Then, schedule an entire day to get everything done that they do. I want you to get a manicure, a pedicure, a full body wax, a facial, a makeover and makeup lessons. If you have the kind of hair that can look girlie, schedule a hair do. If you don’t, tell them that she is going to bring a wig and you want a styling appointment. Then, on your day of beauty, I want you to show up as a guy, but bring an entire girlie, sissy outfit with you to change into when your day of beauty is complete. As far as your reason for doing this, just tell them you are doing it on a dare, or you lost a bet; those two always work!


Hello sweet sissies! I know you fashionista sissies have been pouring over the fall fashion mags. Well, this is a really fun exercise for you to do. I want you to put on your snappiest outfit and sashay your sweet, sissy asses over to your nearest drugstore, convenience store, bookstore, newsstand, wherever you can find oodles of fashion magazines. I want you to get an armload of the best of the best. You know the big thick fall fashion magazines that are jam packed with all kinds of hats, dresses, skirts, blouses, shoes, boots, earrings, necklaces, scarves, make-up tips, hot looks, panties, bras, you name it! It just makes your sissy heart go pitter pat, does it not?

While you are there, pick up a glue stick and a nice, big piece of poster board. When you get home, pour over each magazine and find those images that tickle your sissy sense of style. Imagine yourself wearing those haute couture fashions. Imagine yourself sporting those high-end looks. Imagine yourself walking right out of the pages of Vogue, dressed to nines, and walking right onto the runways of the fall fashion shows in New York City.

How, you might ask? Well, I will tell you how. You are going to cut out all of the images that really speak to you. Arrange those in a pleasing fashion on your poster board, and put that poster up in a prominent place where you can see it often. (Or, if you are shy to put it up in your house, tuck it away and take it out and study it as often as you can.) Then, I want you to…


Hello sexy sissies! I have a super fun assignment for those sissies who are into humiliation. This assignment isn’t going to this assignment is pretty humiliating!be a mild form of humiliation, it’s a bit risky and involves venturing out in public. So this is not for those sissies who are faint of heart, oh no! It requires a bit of courage, okay, a lot of courage, but if you are really into humiliation,

It involves taking something somewhat phallic, preferably a butt plug with a flared base and putting it in your sissy pussy. Now, pick out something very body hugging to wear. I am thinking of a pair of short pink running shorts made of very thin material. You can wear whatever you wish on top and for shoes. But the object of this humiliating game is to have something fitted on the bottom, preferably shorts. And girlie shorts are the best. I want you to go into a store, any kind of store where there are predominantly women. I want you to carry in your arms, a stack of slippery newspapers, perhaps sale papers with a glossy sheen. Something that, when put together in a haphazard way and not bound by a string, or some such thing, will just slip and fall from your arms. When the stack of slippery, glossy papers falls to the ground, bend over at the waist and pick them up. Shift your body weight from one foot to the other while you are doing it, and, I can guarantee you….

Hello sweet sexy sissies! This is going to be a really fun assignment for all of you sissies that are not yet seasoned and are just hatching from your little sissy shells. Since you are just now coming out of the closet, so to speak, you may not have your sense of style defined just yet. That’s okay! That’s precisely how this assignment can help you. What you are going to do is to make a road map of where you want to go as a sissy.

Gather up all of your magazines, catalogues and periodicals, yes, even the naughty fetish ones, if you are willing to cut them up. Get yourself a nice big piece of poster board and a glue stick (glue sticks are better than glue, since glue wrinkles up the pictures when they dry). Now, put on some really good music that puts you in a good frame of mind. Depending on how much time you have set aside, this assignment may take you a while to accomplish, say, over a period of weeks. So find a place in your home or office where you can cut out images and come back to this little project whenever the mood strikes you. Go through each magazine, catalogue, etc., and cut out those images that really resonate with you for some reason (that reason doesn’t have to be clear, just cut out anything and everything that really speaks to you). You may find yourself gravitating to lots of pink and feminine images, that’s okay! It’s even better and more sissy of you to be drawn to those images. Once you have quite a few images, sayings, words, phrases, whatever you were drawn to from the magazine, go ahead and begin assembling them and gluing them to your poster board in a manner that is pleasing to you. Once you are all finished I want you to…

Hello pretty sissies! This assignment is a really fun one. I just finished watching the movie, The Bucket List, and I want you to write down all of your hopes and dreams as a sissy. What kind of sissy things do you want to accomplish in your life? Do you want to eventually take hormones? Get extensions? Have a professional photographer take glossies of you in all of your sissy finery? Take a vacation en femme? Have acrylic nails and keep them on for an extended period of time? Get fucked by a hot Mistress with a strap-on? Find a sissy-loving woman (or man!) and settled down? Get breast augmentation? Perform as a woman on stage? Come out to someone special in your life? You get the idea. Once you have compiled your list, I would love to see a copy if you are brave enough to share. It can be anonymous, but I am very interested in knowing what kinds of sissy dreams you have dancing in your pretty little heads! You can email them to and share them with your sissy sisters and the Mistresses of LDW! Happy dreaming


Hello sweet sissies! I have a very fun assignment for all of you girlie girls this week. Since Summer is here, I think you should go shopping, either online or to a boutique or department store, and buy yourself a sexy bikini. No groaning, girls! You celebrate your sexy, sissy body, whatever your shape or size! I want you to find a bikini that you really love, and, one that fits well. Next I want you to find a nice place to lay out in the sun (please remember to wear sunscreen), or schedule an appointment at a tanning salon. Just think how sexy and sissy your will feel when…

Well hello sweet sissies! This is a really fun assignment for you to try. I want you to get really dolled up, dress to the nines, dress to kill even. Spend a lot of time on yourself. If it takes you all day to really do it right, by that I means, shave all over, give yourself a facial (a real facial, not the cum kind, silly!), give yourself a manicure and a pedicure, do your hair in sexy do, whatever it takes to make you feel totally glamorous. Once your outfit is all picked out, from your lingerie to your dress, I want you to put on the music that makes you feel the sexiest, and strip for yourself in front of a mirror. Really take your time and enjoy…