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: