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.

Your Thirteenth Sissy Assignment

Your Thirteenth Sissy Assignment

You're not superstitious, are you, sissy?

So, you are seeking forced feminization humiliation and what you've done so far isn't enough, is that it?

Was your last assignment too much? Were you not able to do it? 

There can be no other reason for you wanting more assignments. If you had done it, you would now be so obviously feminized that everyone would know. And once everyone knows you are a sissy, you can no longer be 'found out'.

You're here because you want to explore humiliation without going all the way to total feminization. Very well, sissy. I hope you have done everything else, though; shaving, painting, tanning, clothing, sucking, chastity. If not, go back and start from the beginning.

You are going to join a dance aerobics class at your local gym/health club/sports center. Obviously, you will want to fit in with all the ladies there, so you need the right outfit. Go to your nearest dancewear shop. Look it up in the phonebook if necessary.

As a special reward for your devotion to these assignments you have free reign on your outfit for this trip... but you might want to be feminine.

You will buy a pink leotard. Ask for one with a scooped neck and back and 3/4 length sleeves which is cut high on the thighs. Buy a pair of nude, fishnet pantyhose. If they have them, buy Danskin dancers' fishnets. These are very expensive but superb quality and have cotton soles for comfort.

You also need a pair of ladies' trainers in your size (if at all possible), a powder pink sweat or jogging suit and a matching pink lipstick. Lastly, some pink grips for your hair. Wouldn't want it flopping in your face as you exercise, would you, girl?

Try on your new outfit at home. Wear a pair of thong panties underneath everything to protect your balls from the grip of the fishnet. Don't wear your bra.

How do you like fishnets?

Do your red toenails look good?

Your leotard reveals lots of thigh, doesn't it?

Does the scoop neck reveal your bra tan? Check your back in the mirror. Does your tan show there?

You're going to an aerobic class like this. In front of dozens of women. Is that humiliating enough? No. What will be more humiliating is turning up in your pink sweats, showing just a hint of nude fishnet, which might go unnoticed, then stripping down to this. prepare for a lot of sniggers, sissy girl. Even this is not enough. you will apply your lipstick in front of everyone. Now, is that humiliating enough?

You wimped out of your last assignment, but you WILL do this. The idea tantalizes your sissy mind, doesn't it, girl? What are you waiting for? Email your report.

Your Twelfth Sissy Assignment

Your Twelfth Sissy Assignment

Has anyone else noticed how much of a sissy you are these days? Your work colleagues, for example?

Plugged, shaved, plucked, tanned and perfumed, you wear a bra, panties and hose all the time and your fingernails are growing longer and sport clear varnish. I bet the women you work with have noticed something, even if they haven't said anything. They will certainly be curious about what you get up to away from work.

After this assignment, they will know for sure.

By coming this far you consider yourself adept at applying make up, don't you, girl? I hope this is true, because the 'sexy office girl' is having another outing.

Get out your phone directory and check out 'beauty salons' and 'beauticians'.

Yes, that's right. You are going to get a professional makeover. You've done very well to get this far. You owe it to yourself.

Start ringing round. Ask if they would accept a male customer and if they have any objections to you arriving dressed as a woman. You're employing other people in your feminization now, so it's best to make sure they won't be offended.

When you are successful, book an appointment. Take a day off work for this. It'll be worth it. You will ask for -

hairstyling and coloring

manicure 

pedicure 

eyebrow shaping 

a make up lesson 

ear piercing, if they offer this.

This is your assignment. Are you ready? There will be no going back.

For your appointment, you will wear your 'office girl' outfit with your best attempt at make up. As it's a special occasion, you will wear your sheerest pantyhose, your largest butt plug and red polish on your fingernails, even though the nail technician will take it off again at the salon.

You will ask them for the most feminine style they can create with your hair. You will give them total free reign. They may want you to help by choosing something from a magazine. Be true to your self. Don't go for something androgynous. You must also get it colored. Obviously, this will depend on your current color, but there is little to touch a strong henna red or a soft, chili purple for outright femininity.

You will be offered a huge choice of colors for your nails. Choose the best, dark red to go with your new hair. I hope you've been letting your fingernails grow out. If they are not at least a quarter inch beyond your fingertips, you must get half-inch glass fiber extensions to punish yourself.

And can you picture yourself getting ready for your pedicure? Unfastening the dainty buckles to step out of your high-heeled sandals, hitching up your tiny skirt and rolling down those delicious nylons you wear 24 hours a day. Then having a nail technician remove your nail varnish and add a new, dark red polish? Don't forget, you must not cum.

Get a single piercing in each ear. Choose pearl studs; they're more attractive and feminine than gold or silver.

Leave the style and extent of your eyebrow shaping to the experts. Just ask for something suitable for the shape of your face and your hairstyle and more feminine that what you have done already. Maybe you'll end up with pencil thin arches, maybe not. Won't that be exciting?

For your make up lesson, tell them you want an evening make up, no matter what time of day it is. This usually translates as 'glamourous' (or tarty, depending on your viewpoint). Listen to the beautician as she describes everything she's doing in great detail. Remember: do not cum.

When you leave the salon, linger at the local stores. Go for a coffee. Show the world the glamorous sissy you have become. After all, if you can't pass now, with all this professional help, you never will.

Get out your little compact mirror and study the new you. Do you like what you see? Play with your earrings. They feel good, don't they? You paid a professional to do your face, nails and hair. Don't you look fantastic? You can remove the cosmetics but you'll never pass off your new hair as 'male'. Nor those eyebrows. Maybe you need to stop pretending and out yourself as the true sissy you really are. You'd rather be a woman, anyway. That's what you've been training for, isn't it? That's why you're so good at making up your face and sucking cock; why you have a bikini tan and wear a bra, panties and pantyhose 24/7; why you shave your legs and paint your nails; why you haven't let your pathetic boy clit spurt for so, so long. That must be so difficult when you look so gorgeous.

Undo your jacket. Look at the way your breasts stretch your top. Look down at your lap. A miniskirt barely covers your nylon-clad thighs and your professionally- painted toenails glint back at you past the delicate straps of your high-heeled sandals. Wiggle your toes. Don't you just love that sensation as they gently stretch their nylon prison? You are nothing but a feminized sissy girl. Give up your last pretenses at manhood and start living as a woman - full-time.

If that's what you decide, then good luck and farewell. These assignments have helped you find your true self. You can now graduate. EMAIL your final report.

Or is this too much for you? Do you prefer the humiliation of being a secretly feminized man, 'forced' to do things against your will? Perhaps you need some more assignments, then.

Your Eleventh Sissy Assignment

Your Eleventh Sissy Assignment

Hello, my bra-tanned sissy girl. Stand naked before a mirror and look at that indelible lingerie burnt onto your skin. What more humiliations can be in store for you, sissy?

Are you bored of cock sucking yet? Does it need spicing up a bit?

You are going to buy a new toy. You are going to a sex shop to buy yourself a butt plug. The reason you are going shopping and not buying it online is that you are going to be dressing up, but you probably guessed that, didn't you? Clever girl.

You are going to be shaved and perfumed and in bra, panties and hose, as you are every day. You need not fill your bra. You will wear your choice of male clothes and shoes. You will also wear foundation, lipstick, mascara, eyeliner and at least one shade of eyeshadow. The choice of colors is up to you.

Take your sissy, feminized self to a sex shop and buy not one but three butt plugs in different sizes. You'll also need some lubricant.

Back home, you're going to start buttfucking yourself. Pull down your pantyhose and panties. Smear some lubricant against your hole and slowly work a greased finger inside. Fuck yourself with your finger. Does it feel good, sissy butt boy?

Get the smallest plug and slowly fuck yourself with it. Once you're past the widest part it will suck itself in until it's base is nestled tight up against your hole. Do you feel full? Remember, that's the smallest one.

Start sucking your dildo and masturbate. 

Notice how your sphincter tightens around the plug as you play with yourself. Do you feel hot? What a shame you aren't allowed to cum.

Keep your plug in for at least an hour.

Increase your plugging time by an hour a day. Once you've managed six hours, move up to the next size plug and start again at one hour. Repeat until you've worn your largest plug for a full day at work before moving on.

Imagine a full working day - shaved, perfumed, bra, panties, pantyhose, nail varnish and now a butt plug. No real man would even dream of doing this. You are such a sissy.

Your Tenth Sissy Assignment

Your Tenth Sissy Assignment

Welcome, sissy girl.

This will be short and sweet. Two simple tasks with the most enduring consequences of any of your assignments so far.

One

You will hire a sunbed, one that will tan you both sides at once, like a piece of bread in a toaster. Twice a day, you will dress in a bikini or panties and a filled bra and build up a delightful, feminine tan on your sunbed. Be careful to position your bra straps in the same place every day so that the outline is crystal clear. Do not even consider returning the sunbed to the store until you have done this for a week and have very obvious, sissy tan lines, front and back.

Two

Pluck your eyebrows. Follow the advice below to get a pretty arch.

How feminine do you dare go? Delicate, pencil-thin arches will make your face much sexier. Much more room for eyeshadow, too. Do it, sissy girl.

From now on you will pluck your eyebrows every week. Don't forget to continue your make up, cock sucking, shaving, heels and underwear routines as well.

Do not cum.