Your 21st Sissy Assignment

 Your 21st Sissy Assignment

Right, you slut, you've had it all too easy so far. You want to be forced to dress as a woman, don't you? From now on, you're going to be fully dressed as a woman all the time.

That means a MINIMUM standard of:

- fully shaved with plucked eyebrows

- perfume

- feminine hairstyle (baldies must wear a wig)

- feminine watch, ring(s), bracelet, anklet, necklace, earrings

- polished fingernails and toenails

- panties and filled bra

- pantyhose (or stockings and suspenders if you must)

- skirt and blouse/top OR a dress (I hope you've been using your initiative to expand your wardrobe, especially skirts and dresses, otherwise you will be wearing your 'office girl' suit out!)

- high heels (minimum 2.5"/6.5cm)

- carry a handbag, clutch bag or (in USA) purse containing spare pantyhose, make up bag and pantyliner

- full make up.

The MINIMUM standard for make up is:

- foundation

- powder

- blusher

- eyebrow pencil

- eyeliner

- mascara

- two shades of eyeshadow

- lipliner

- lipstick.

When asleep, the minimum standard is -

- face cream

- hair, nails, perfume, shaving as before

- anklet and ear studs

- underwear and hosiery as before (i.e. FILLED bra)

- baby doll nightie (you may go without your bra if this is underwired)

Print this page out so you have a permanent copy of your dress code.

As a generous Mistress, I will allow you 60 minutes of Drabtime for public activities. Drabtime is when you are allowed to wear male OUTER clothes (a.k.a. drab).

And that isn't 60 minutes a day, sissy girl, it's 60 minutes a WEEK.

Better spend your Drabtime wisely. Grocery shopping? The gym? Buying replacements for your snagged pantyhose? These will probably take up your entire week's allowance. Looks like you're going to have to go out as your true, feminine self a lot more. If you use more Drabtime than you are allowed, you must EMAIL the Station Mistress for your forfeit.

It won't be pleasant. I just love forfeits.

If you have to go out to work, you may (for now, at least) wear drab from when you leave your house until your return. Calculate how many hours this is each week and add it to your Drabtime allowance. It goes without saying that if you work from home, you don't get any extra allowance.

I suggest you carry a timer with you - find one that will countdown the required number of hours and has an alarm. Set it to your total Drabtime at the start of your week and start the counter the moment you are improperly dressed (as a man). It would be embarrassing to have to explain what the alarm was for if it went off in public, wouldn't it, slut?

DON'T CHEAT. You are only cheating yourself. I have a mental picture of hundreds of sissies running red lights to get home before their Drabtime allowance runs out - racing home to get into a dress and heels and put their make up on as soon as possible. Delightful! Don't disappoint me, sissy. Just don't get a ticket. The police probably wouldn't find your excuses acceptable!

Your Twentieth Sissy Assignment

 Your Twentieth Sissy Assignment

Cum-cubes.

Does the word fill you with dread now?

Did anyone notice your cum-breath?

Congratulations on reaching your twentieth assignment. As a special treat, your new task involves going to the cosmetics section of a large department store. Start masturbating now, sissygirl.

Perhaps you should read all Ms. Angela's stories on the story page to get you in the mood.

First, you need wardrobe advice, don't you sissy?

Start with your Basque and a pair of black stockings. Bind your boy-clit and sissy balls with one of your special stockings. Don't wear any panties. This way, your unsightly bulge will be more prominent and you risk a wet mark in your slacks as your boy-clit becomes slick with pre-cum. Wear your palest slacks and a sissy blouse.

Is your bound boy-clit embarrassingly visible?

Are you worried that your Basque is very obvious?

If so, you may wear the jacket from your ladies' suit over the top. Wear perfume and jewelry as usual. Wear your loafers. Wear glittery polish on your fingernails. Don't wear make up. You won't need make up...

Go to a large department store. Make a few circuits of the make up area. Establish who is offering make up demonstrations. Chose the demonstrator you think is wearing the sexiest make up. They are always heavily made up but some look better than others. If you are too afraid to ask, wait until Halloween and use that holiday as your pathetic excuse.

Compliment her on her make up.

Tell her you would like to be able to copy the way she has done her eyes (or lips, if you prefer).

Ask what products she used.

By now (particularly if she has noticed your sissy appearance), she will probably have guessed where this is going and, if she is obliging, she may offer to demonstrate on your face.

If not, suggest she could do so.

If she refuses, thank her, apologize for inconveniencing her and try another store.

Otherwise, perch your sissy ass on her stool and prepare for the thrill of being made up in public by a willing female.

Thank her profusely. Buy everything she suggests. Wear your pretty, new make up with pride as you go to the checkout to pay for your cosmetics.

Blog and report to your Mistress with all the humiliating details and you may see your report posted on this site.

Your Nineteenth Sissy Assignment

 Your Nineteenth Sissy Assignment

Was it nice to be allowed to cum so much?

Well, that's all over now. Back to chastity, for you, sissy girl.

There is a tray full of frozen cum in your freezer. What are you going to do with that?

Read on.

Every working day, just as you leave the house, you will put a cum-cube in your mouth and suck it until it has all melted down your throat. You will NOT use gum, breath freshener, toothpaste or any other subversive means to undermining the humiliation of arriving at work with the smell of cum on your breath and the taste in your mouth all morning. A shaved and perfumed sissy wearing lingerie, jewelry and nail polish, complete with the smell of fresh cum on her breath.

And not just once, but for days on end, until you have used up all your cum-cubes. Deliciously humiliating.

It should take you at least two weeks to use up your cum-cubes. If you enjoy the taste of your cum after your cock-sucking training, then you may find your first, frozen cum-cube thrilling, but two weeks later you will be wishing you never started this. But you must do it, because this is the cost of your sexual release from now on.

Your Eighteenth Sissy Assignment

 Your Eighteenth Sissy Assignment

Have you enjoyed your month in stockings? Not nearly so thrilling when you wear them every day, are they? Hopefully, you're now cured of your fascination for them and are longing for pantyhose.

You may have been wondering why you had to save a brand new pair of stockings. Get them out now. You also need a condom and two clothespins (clothes' pegs) and an (empty) ice cube tray. Strip naked. Naked except for your jewelry, perfume, nail polish and full, heavy make up, of course. And your biggest butt-plug.

Masturbate until your boy-clit is hard. You may want to suck your trusty dildo if you need inspiration. You know how horny that makes you feel. Put your condom on. Now bunch up one of the stockings and put this over your boy-clit, like a large, nylon condom. Pull it right down over your sissy balls. Twist the stocking behind your sissy balls and pass the bunched nylon back over your balls. Twist again and pass this, much tighter, pocket of nylon back over your balls. You now have your boy-clit covered in latex and nylon and three layers of nylon compressing your sissy balls.

Does it feel good? Is it tight?

Masturbate slowly. Tease yourself. Do not cum. Attach the clothespins to each of your nipples. Feel them bite into your tender flesh. Have you ever experienced a sensation like that?

Do not cum. Now put your bra on and fill the cups. The extra pressure on your nipples will heighten the sensation. Now choose your silkiest pair of panties and a pair of slippery, high-lycra pantyhose. Your boy-clit and sissy balls are very prominent, aren't they, slut? Choose a blouse and a pair of slacks and put your sandals on. You may not hide behind an overcoat or sweater.

It's time for a walk, just round the block will do. You should look quite passable, apart from that prominent bulge in your slacks. If the weather is cool, your nipples will be rock hard, making those clothespins bite even harder. When you get back home, suck your dildo while you pull on your tightly constrained sissy balls through your clothes.

Now you may cum, the release you've been dying for.

But when you have spent your disgusting sissy mess you will carefully remove your condom, collecting as much cum as possible from your boy-clit, then pour your cum into the ice cube tray and put it in the freezer.

Repeat this exact ritual every day until your cube tray is full.

You already dread your next assignment, don't you, sissy cum-slut?

Your Seventeenth Sissy Assignment

 Your Seventeenth Sissy Assignment

You have been deprived of a lingerie experience, haven't you, sissy slut?

Now you are very, very well used to pantyhose, you're going to have a change.

Stockings.

You may have worn them before you started these assignments, after all most men are fascinated by them, even though most women don't wear them. But you're not a man or a woman, so you're going to wear them 24 hours a day for the next month.

But you have to earn them.

And you have to buy them. For your shopping trip, you will wear; your largest butt-plug, your cock tucked in your tightest panties with a pantyliner, an unfilled bra, a white blouse, black pantyhose, ladies' slacks, court shoes, red nail polish, all your jewelry, no make up. Take your handbag.

You must dress like this for your trip, or you will not get to wear stockings. And you do so want to, don't you, sissy? To feel the tug of taut nylon on your suspender straps (garter straps, American sissy) as you walk and sit, the stretched strap sliding over your hips as you move, the slightly sagged stocking top rubbing your inner thigh, the teasing femininity of buckles and clips under your hands as they rest in your lap, the visible bulges of lingerie on your thighs.

To experience all of this, you must first humiliate yourself. In your pretty outfit, your new court shoes will look very feminine and make it obvious you are wearing nylons. Your bra will be obvious, as will all your sissy jewelry. But you will be rummaging through racks of stockings with painted nails. That will be deliciously embarrassing. And all with no make up to hide behind. Did you ever think you'd wish for the extra humiliation of make up? Perhaps you did, you naughty little sissy.

Go to your favorite lingerie store, where you buy your bras and panties. Treat yourself to a complete set of matching bra, panties and suspenders. A good tip is to look for metal buckles on your suspender straps, because these grip much better than cheap plastic. As ever, invest in your femininity. Also, look for a belt deeper than just a single hook and eye at the back because these can be uncomfortable and unless you have good, sissy hips, won't stay up as well. You may well learn to your cost how much of a nuisance this is.

You will also buy a Basque, or corset. Buy on bust size, but check for the quality of all the straps and fastenings. There will probably be some matching panties for you to buy, too.

Now go to your hosiery supplier and buy fifteen (yes, 15) pairs of stockings in a variety of styles and shades. You may indulge yourself with lace-tops if you wish. You may buy hold-ups (thigh highs, I believe you Americans say) but you must still wear them with suspenders. This is actually quite a sexy feeling; because the stockings are fixed in position, the suspender straps tense and relax much more when you walk. Don't buy fishnets, don't buy opaque, don't buy multipacks.

You are such a good sissy for wearing such a humiliating outfit for your lingerie shopping. You might think your purchases are their own reward, but no! You will give yourself an even greater reward. Go to a coffee bar and order a drink. Slide the plug in and out your ass with the pressure of your buttocks. Discretely, beneath the table, stroke yourself like a girl, gently, with one of your painted nails. Stroke your aching boy-clit. It probably won't take much to make you cum, will it? It's so long since you've been allowed to cum, isn't it, slut? You're going to explode in your pantyliner. Cum before your drink arrives. Feel the hot semen fill your liner and maybe leak out into your panties. Maybe your shorts will be wet, maybe your pantyhose will be wet below the hem of your shorts as your cum leaks away. Maybe there'll be a little crust on your thighs before you leave. That would be humiliating, wouldn't it?

Wear stockings every day and night for a calendar month. Wear your Basque and your three-piece set on alternate days. Remember, wear your panties over the suspender straps so you can pull your panties down when you sit to pee.

Do not cum, no matter how horny you feel. Save one pair of stockings for a special purpose in your next assignment.

Your Sixteenth Sissy Assignment

 Your Sixteenth Sissy Assignment

You're going on another long and embarrassing shopping trip. You need to expand your sissy wardrobe and you need jewelry.

You will, of course wear your regular bra, panties and pantyhose, with shaved body, painted toenails, perfume, ladies' watch and handbag. Your fingernails will be glittery. You will wear your women's slacks and a white, collared shirt, with the top three buttons open, so you risk exposing your bra when you lean forward. For now, make do with your male shoes.

Wear your best 'nude' make up look. I'm sure you are experienced enough to know this does not mean 'no make up'. You will wear foundation, powder, eyebrow pencil, eye pencil, eyeshadow, mascara, blusher and lipstick, but in subtle colors that, from a distance, make your face look unpainted. Of course, up close, any woman will notice, but that's what you want, isn't it, sissy? Besides, they will notice your nails and your bra and your perfume and the side zip on your slacks, so why be embarrassed about a little make up?

First stop is a jewelers. Jewelry stores offer great scope for sissy humiliation. They always offer such personal attention. Try to go at a quiet time so you get this attention. Ask to look at ladies' rings. You will almost certainly be offered a seat, which means you will expose your ankles in their pantyhose. Then you will have to point out your choices on a selection of trays, drawing attention to your painted nails. The ring you are looking for is a solitaire; a thin band with a single stone, possibly an engagement ring. When you have made your choice, you will be asked the size. You must tell the jeweler it is for your own ring finger. Unless your fingers are disgustingly pudgy (in which case, why aren't you trying to make yourself slimmer, you slut?), they should be able to stretch it to fit. You will then wear your ring.

You also want an ankle chain which you will put on in the shop over your pantyhose. Won't that be humiliating? Drawing attention to your shaved legs and nylons. If they offer engraving, ask for your sissy name to be added. In future, you will wear your anklet under your pantyhose, next to your skin. You will never take it off.

You also want a bracelet. Choose the most delicate chain available, something a real man would never wear.

Your next purchase is a necklace. Not gold or silver this time, but a string of fake pearls (unless you can afford the real thing). Wear them now, too. They will look lovely wth your open shirt.

Finally, a pair of ear-rings. You did do as you were told and get your ears pierced, didn't you? If not, you will do it today. Buy a pair of delicate drop pearls (fakes are permitted, unless you're wealthy) and put them on.

Now you have pretty jewelry, you can do the rest of your shopping.

Next, you're going shoe shopping. Sadly, it won't be as much fun as this...

...but you need shoes. It must be very frustrating for you to have to wear men's shoes when you go out on these assignments. You're going to buy some black loafers with a raised, block heel. The unobservant eye might see them as men's shoes, but anyone taking a second look would know. You MUST ask to try them on. Don't forget, you are dressed, perfumed, made up and now even bejewelled like a woman; the shop's staff will know the shoes are for you, so you might as well make sure they fit. After all, you're going to spend a long time in them.

Slip off your male shoes to expose your red toenails behind the reinforced toe of your pantyhose, your anklet glinting at you. Taste your lipstick as you bite your lip in shame. Slip your feet into the new shoes. Walk in them. Does it feel good to be back in heels?

You will also buy a pair of court shoes with a mid-heel of two to three inches.

Aren't they comfortable? Of course, sissy. Why do you think so many sensible women wear them?

Wear your loafers for the rest of you shopping. Apologies to those of you with enormous feet. You will have to do your shoe shopping online and miss all this humiliation.

The rest of your shopping list is:

- three pairs of ladies' slacks in light colors with side or rear zips and no elasticated waistbands. Try to choose fabrics not used for men's trousers.

- a pair of ladies' shorts (this could be tricky if you're trying this in winter). Again, side or rear zip, non-elasticated waist, pastel color.

- three white blouses, cut like shirts but with the buttons on the 'wrong' side for a man (but the right side for you, sissy girl).

- a roll-neck top in a bold color.

- a pair of opaque (60+ denier) pantyhose/tights in the same color as your new top.

Can you guess what's coming next? Not your sissy boy-clit, that's for sure!

Go to your favorite sissy changing room (aka public bathroom). Strip down to your bra and panties. Now would be a good time to put your ankle chain in it's proper place. Put on your thick tights. They give your legs a good, strong color, but they're so lifeless after sheer, aren't they? Don't worry, you won't be wearing them regularly.

Put your roll-neck top on. Now your new shorts and your loafers. This is the look you are aiming for.

shorts and opaque for you, sissy

Are you ready to go out like this? Perhaps you should refresh your make up. You did bring it with you, didn't you, sissy? Redo your eyes with some darker shadow and a black pencil. Run your favorite red lipstick over your girlish mouth. Put on lots of blusher. Now go for it, sissy.

From now on, you will wear all your new jewelry 24 hours a day, EVERY day.

You will wear your loafers to work. They are you new work shoes, sissy-girl. Wear them with pride. And a little sway in your step. I hope you look a little like Catherine: 

Your Fifteenth Sissy Assignment

 Your Fifteenth Sissy Assignment

You're going out again. It's going to be humiliating.

From the head down, you will wear:

- your hair in a masculine style

- no make up

- no jewelry

- a shirt and tie

- men's, three piece suit (if you have one, otherwise a two piece will have to do)

- black bra, panties, sandal-toe pantyhose

- red fingernails and toenails

- high-heeled sandals

Now go and do your regular grocery shopping.

You will be so humiliated as your heels click-clack up and down the aisles, reaching out for grocery items with your feminine hands. Pay by credit card, sissy, so you have to sign your male name whilst holding the pen between those pretty, feminine nails.

Blog your report.

Your Fourteenth Sissy Assignment

 Your Fourteenth Sissy Assignment

Was your aerobics class fun?

Have you made any new friends?

Did someone offer to do your make up, or say she wished her husband would do something like you?

You love to be humiliated, don't you, sissy girl?

This time, you're going to a print shop to get some slogans printed in big letters on white, skinny-rib, ladies tops. Choose two from the following:

- Is there a run in my pantyhose?

- Would you like to see my pretty, red toenails?

- I'm wearing panties.

- Please feminize me.

- Please put make up on my face.

- Yes, I am wearing a bra.

Needless to say, you are going to wear your new tops, over your bra, every time you go out of the house, except to work.

DO NOT try to cover your top with a coat, jacket or sweater. Is that clear?

Have a good time...

Blog your choices, if you have one.