Sissy Training Assignment from Mistress Cassandra


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Makeup shopping at the mall.

One thing I love doing with gurls is to bring them shopping at Sephora. The makeup kiosks offer try me samplers. At the end of the kiosks there are mirrors, sponges, all kinds of disposable applicators, and makeup remover. Often there are makeup artists on duty to give you a nice makeover. There is every perfume imaginable, skin care products, hair products, and fabulous tools such as brushes and hair styling tools.

Now my dear sissy, it’s time you venture in and browse the aisles. Go in on a busy Saturday for the maximum impact to nurture your girlieness. Be sure a makeup artist is available, and even better, it would be nice if she could make you over an hour after you enter.

Now go through each and every kiosk trying on the prettiest makeup you can find. Apply and remove to the next kiosk until your makeup artist is ready for you. Be sure to visit the skin care section and apply some serum and moisturizer before she goes to work on your freshly pampered skin.

Now it’s that time to sit in that tall chair and get primed, foundationed, blushed, and powdered. Relax and close your eyes as she (or he) applies creamy powdered shadow to your lids. The gentle tug of your curled lashes with sumptuous mascara, the tickle of kohl eyeliner, and the sensuous sensation of creamy lipstick gliding on your plumped lips.

Not such a hard assignment now is it? After you have done this assignment , call for a session and we will go over the experience detail by detail

It’s the mall for fall!

Halloween is upon us and you must prepare now for the festivities that sissies love most! Dressing up!This is a huge fantasy night, so think about it. Someone historical like Cleopatra, Marie Antoinette, a medieval maiden? What about Scarlett O’Hara, Little Bo Peep, a beautiful angel in white , or maybe a faerie with colorful elaborate wings. Maybe the sissy will want to try her look into the Dominatrix realm. I dare you!! If I were there I would loan you a riding crop! LOL How about you go to the maximum all dressed up in the most formal of sissy attire. The most over the top of all street walking sluts is always a favorite. Most malls provide a temporary costume outlet for the sissies favorite holiday, so guess where you are going. That’s right, to the mall. Of course little sissy will go into Clair’s accessories to top off her costume, because I simply have the feeling little sissy is going to want to be the sluttiest of sluts this holiday, right? I guess you may as well hit Victoria’s Secret then for your stockings and maybe a new corset with black sequins. I think you may also go to Sephora and buy the most glittery slutty eye shadow you can find. I suggest Urban Decay’s “Graffitti” in bright slutty green. I’m sure you can find just about any slutty glittery eye shadow. I suggest, make an appointment for a makeover for that night! And don’t forget the sluttiest of lipstick!

Often Mistresses go “transgenderspotting”.

What makes a sissy eligible for a Mistress. This assignment is about attracting the Mistress of your dreams.

It’s absurd to assume that a Mistress will want you as a gurl 100% of the time. Sometimes Mistress will need an escort to events that require a male. This is when special talent comes in. You must be a “dandy”. A crossdresser by nature is a peacock, a feminine male of “gay” taste. This assignment requires you to delve into fashion magazines and study haute couture, to piece together items that look creatively androgynous. This requires a different kind of haircut as well. Many young Hollywood males have geometric girlie cuts. One doesn’t think “sissy” here, they think “in the industry” or an artist. This is unrealistic for many parts of the country, so put your creative thinking cap on. How can you look sexy to a Mistress in Wichita? Look to a fashion magazine to stand out from other males in the area. It’s a no brainer in dress up situations private or out. You must study makeup manuals, shop in lingerie stores , order online from crossdressing shops, and most of all , observe female perfection. I don’t need to get into walking and submission as you already know that. Approaching a Mistress is eyes lowered, a curtsy, and in deep submission say “my name is sissy…”, and if She offers Her hand , then carefully kiss it leaving a tiny trace of your lipstick so She may remember the gurl that She may consider.

Are you lucky enough to have served a Mistress as a sissy maid?

Today you will learn through research. Google “sissy maid training” and see what you come up with, then send Me your links so I may study and approve.Things to keep in mind is the perfect maid’s uniform, how you present yourself to your Mistress, the perfect curtsy, and domestic skills of course. 

The best sissy maids are proficient in high tea service. Kitchen duties of tea sandwiches, canapés, spotless maintenance, cocktail talents, entertainment for the Mistresses including foot massage, pedicures, and oral service if it is so demanded. The uniform must be well maintained and the posture must be correct.

A sissy maid who does not fulfill duties should accept canings and other corporeal discipline. But this is not the case with you is it? You will be well studied and prepared. Remember the best sissy maids are paragons of perfection! Send Me your links.



I declare this week “Sissies in Rope Bondage Week” to celebrate Sandra Gibbon’s site TranniesInTrouble and also to celebrate sissy as damsel in distress.

Oh I know it’s a huge fantasy in the sissy community, so treat yourself to some rope. Twisted Monk and Rainbow Rope sell pink rope for gurls, and they provide some video lessons, in fact Twisted Monk includes a dvd with every purchase. Some great photos of sissies in bondage, dressed to the nines are on Sexy Sandy’s site.

Assignment time

Order some pink rope from the source of your choice. Experiment with knots and ties but be careful, no extreme bondage if you’re alone. Set up your camera and dress your absolute sluttiest like the pictures on Sexy Sandra’s site. You may or may not be gagged. Maybe you like lipstick more than gags. The challenge is to totally look like a damsel in distress, in need of rescue from a Dominant Mistress or Master. It would be so good if you had a bondage partner, tying you in intricate knots. After you have done your assignment, email Me the finished photos for posting. Remember, the key is PINK ROPE!



Have you gotten your bikini yet?

It’s the middle of July, dearies . . . waiting for what, hmmmmmmmmmmmm? It’s shopping time – get your sissy ass in gear and get to your nearest Macy’s or whatever you have in your town. I’m not talking looking without trying either. That’s right – you will be trying several bikinis on.

I want you to consider tan lines as well. Sexy tan lines that define a sissy in a bikini top. So let’s get to it. Let’s get the strappiest pinkest and most floral of all the bikinis now. Let’s match those shoes of yours. The pretty sexy and pink strappy sandals that make you so hot and sexy.

Now make an appointment to have a tanning session at a tanning booth. When they tell you to remove the bikini, tell them no. Tell them your Mistress requires tan lines and that you are a little girlie sissy nancy boy. Do it. I guarantee you will feel so much better!



It’s shopping again and this time it’s dildo shopping, gurls!

You will dress slutty for this one, so get out your miniskirts and thigh highs, and of course breast forms and a black lacy bra underneath a semi-sheer blouse, to show those straps . A pair of sexy strappy sandals, a blond wig, and lots of slutty makeup should complete the look. The clothes can be any color you like but not pink. Today you are a slut going to an adult toy store.

Start at the dildo counter and get the biggest and baddest black dildo they have. You also need to get a series of butt plugs to train that pussy so you can take a good pounding. Don’t forget the lube either. Next I want you to buy a pair of (preferably) pink anal beads for your little pussy too.

Most adult toy stores have a clothing section. It’s time to stock up on stockings and rhumba panties if they have them. Make sure your nails are done for this too, dear. You certainly wouldn’t want to dig into your little pink wallet with your nails not done, now would you



It’s off to the spa for sissy!

Today you will get the works: Manicure with french tips, pedicure with scrub, a full body waxing, and a spray on tan to start the summer off. You will start out with short to medium length silk wraps. Too long too soon will be too shocking for those who “had no idea”. You will then have a delux pedicure which will consist of an exfoliating sea salt scrub, a rejuvinating mint cooling masque for the feet, followed by a warm towel wrap. You may need to have calluses removed as well. Ask the attendant if they offer parrafin treatment which will further soften the sissies feet.

Next you will get the full body waxing. It will be a bit painful but well worth it. Women suffer for beauty and so shall you. And we can not start off summer as white as a ghost now, can we? An airbrush spray tanning session is in order. It will last two to three weeks, so it’s up to you to maintain it and keep it shining with luxurious bath gel and a moisturizer to follow.

It’s always a good idea to exfoliate the whole body before the spray tan, and always a great idea to add a facial while you are there, a nice 60 min aromatherapy facial.Have fun, sissy boi. This is a great assignment for boi and Girl alike!



It’s shopping time again!

This time for feminine products in Walgreens. This means dressed enfemme, with your new spring collection heels, in pink , with makeup and nails done in french manicure.

Toes and fingers!

By now you will have gotten rid of all of that grotesque hair on your bodies and pussy area. A nice painful waxing is best because you must learn what it’s like to be a girl. Girls suffer for beauty and so must you! Now I want you to bring your cell phones and call Me while you are shopping, as I will direct you to the Summer’s Eve douche, the pink Daisy razors with aloe strips, Playtex tampons in super absorbent, some Kotex mini pads, and of course some pink shaving gel in any brand.

Girls wear deodorant, so I want you to buy a girlie brand, not in silver but in pink. Let’s top the trip off with a pink cosmetic bag to carry the pink lipstick, nail polish, and Maybelline compact.

I want you to ask for help if you cannot find any of these items…in your best girlie voice, that is. Oh, and I want you to go to the condom section and ask a sales girl if they have any extra small…lol. I want the receipts scanned and sent to My email as well. Be proud as you walk to checkout. Humiliation is part of being sissified, so embrace it. Now if Ms Marcy Monroe can do this assignment , you certainly can!



I wonder how many of you have an online diary. It’s very important for a gurl to chronicle her journey of girliehood becoming, so I want you to get to work. WordPress may be a bit techie for some ditzie sissies, and also they may censor some content, so I recommend Google’s own “Blogger”. Blogger has themes you may edit and they have several “girlie templates” . A great example of a gurls work in progress is “sissy dolly anne’s training” dolly took the template and added her own colors as well as font. Be sure to specify in settings that this is an adult blog.

Blogging requires discipline even through purging times. During these times you may not want to even look at this blog but I urge and order you to do so. This is the perfect opportunity for you to post links you would like to share with other sissies, post your Mistresses link, shopping, anything relevant to becoming girlie.

I want you to get started right away and email Me your blog links so I can view , approve , and suggest anything else to your diary!