Sissy Station went down recently – figured I needed to store its excellent “Sissy Assignments” somewhere. Unfortunately the pictures have been lost. When I have more time, I’ll break this into pages and find appropriate pictures.

Hello, budding sissy. So, you want to be feminised, do you?

Do you fantasise about being made to dress like a woman, look like a woman, think like a woman and act like a woman? Have you imagined yourself as each of the beautiful women on the gallery pages?

Do you like the humiliation of being made to wear women’s things in public when you’re still obviously a man?

You’ve come to the right place, sissy.

On the following pages, you will be given a series of assignments which will take you on a journey through humiliating sissyness and on towards your total feminisation. Here are some examples, sent by a devoted sissy…

You want to be feminine, don’t you? To hear the clicking of your stiletto heels as you walk, feel the swish of pantyhose as your nylons rub together on your smooth thighs, beneath your tight, lined miniskirt which slides over your ass, your heavily-styled hair and heavy earrings brushing your neck, your shoulders feeling the pull of heavy breasts in your bra, tasting lipstick on your lips and smelling your perfume, make up and hairspray. You want it, more than anything, don’t you?

One day, sissy, one day.

Please don’t ask for personal training, though. Follow the assignments here. There is enough to keep you busy. Even if you are an experienced sissy with your very own, feminine wardrobe and you dress regularly, the discipline of having your femininity enforced by these assignments will still be thrilling.

You are welcome to send in reports on your progress, if you wish. Please include your sissy name in your email. The best reports may even end up on a new display at the station.

So, are you ready?

Your First Sissy Assignment

This is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.

Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a whole shop dedicated to women’s underwear – bras, panties, suspenders/garters, slips, camisoles, nighties, negligees, peignoirs, stockings, pantyhose. Every customer is after one thing; lingerie. No doubt you’ll be the only man in there. Everyone will wonder if you’re shopping for yourself. Well you are, aren’t you sissy?

Don’t buy cheap underwear. This is an investment in your femininity, so buy quality that will last. Study all the available choices of panties. Chose a pair of white, brief-style panties, but try to find a pair with a lace front panel. Make sure they are your size. Don’t forget, you are a man and you need to make room for your pathetic cock and balls, so don’t buy panties with a narrow gusset unless you want to be squirming and fiddling all the time.

Take them home and put them in your underwear drawer. Do not wear them… yet. Tonight, when you undress for bed, throw away those nasty, male undies you are wearing. You have a new pair of panties to take their place now.

Tomorrow, you will wear your panties all day. If it’s a work day, try to imagine which of your female colleagues might have prettier panties than you.

Hand wash your panties each evening and wear them every day. Discard a pair of male undies for each day you wear panties.

Do not proceed to your next assignment until you have worn panties for at least one week.

Your Second Sissy Assignment

How is my little panty-wearing sissy coming along then?

Your second assignment requires some more shopping. You will return to the same store as last time. How humiliating. Perhaps the assistants will remember you bought some panties recently. Maybe they’ll be wondering if you’re wearing them right now.

You will buy a second pair of panties; this time a thong. Try to find one in pink. You will also buy 7, yes seven, pairs of pantyhose. Don’t cheat and buy multipacks; buy seven separate packages in a variety of brands. If they aren’t ‘one size’, be sure to check they will fit. Purchase at least one pair in black and one in nude. Buy only 5, 7, 8 or 10 denier; no opaques or semi-opaques, no patterns and definitely no fishnets. Opaques are sweaty and dull and fishnets are for tarts.You are a sissy, not a tart. Sissies want to be feminine. Sissies wear sheer. You will be feminine. You will wear sheer.

When you go to the checkout, the assistant will have no doubt that you are buying pantyhose for yourself. You’re not going to buy seven different pairs for your girlfriend, are you? Don’t be embarrassed; relish the thrill of being in the presence of a woman who knows you are a sissy. Be in awe of her; you are just starting out, learning to be feminine, trying to be more like her. Even if she is plain, she is more feminine than you will ever be.

You will have guessed why you have bought seven pairs of pantyhose. You now have a different pair for every day of the week. You will always wear pantyhose from now on – at home, at work, in bed, at the grocery store, at the gym, at a nightclub – wherever you go you will always feel the caress of nylon against your legs.

Discretely, look at the legs of every woman you meet. Is she wearing pantyhose or stockings? Is she wearing the same shade as you? Is she wearing the same denier as you? After a while you will have enough experience of hosiery to be able to answer these questions. And don’t dismiss a woman just because she’s wearing trousers. Some women even wear pantyhose under their trousers; after all, you do, don’t you, sissy?

From now on, you will wear your pantyhose 24/7 except to bath or shower. In fact, you can also wear them in the bath or shower if the mood really takes you. You will be tormented by the sensation of your legs brushing against the sheets as you try to sleep. If you ladder a pair, you will buy a new pair to replace them. You will handwash each soiled pair every day.

Your new panties will be alternated with your old pair. Discard all your male undies now. You will not keep any. Even if you have to go to the doctor, you will do so in panties. There is no going back.

Do not proceed to your next assignment until you have worn pantyhose for at least two weeks.

Your Third Sissy Assignment

Are you used to wearing pantyhose? Don’t they feel great on your legs? Do you get a new thrill looking at women’s legs? Do you wonder about being discovered?

So far, all you have changed is your clothes. In the next few assignments, you will change your attitude.

What defines you as a man? Your cock does, no matter how puny and pathetic it is. A cock is not a feminine thing. From now on, you will call it your boyclit. I bet you’ve jerked off in your panties as you’ve enjoyed the silky, slinky feel of sheer pantyhose on your thighs. Not any more. From now on, you may only cum when you have permission to cum. You are free to masturbate, in fact you must masturbate regularly, but you will not cum without permission.

The other problem with your boyclit is that it enables you to pee standing up. Not any more. From now on you will sit down to pee like a proper girl. Pull down your trousers, pull down your pantyhose, pull down your panties and pee. Wipe yourself when you’ve finished. You want to be a clean, sissy girl, don’t you? Everytime you pee, you will drop your panties. No popping your boyclit out over the top, okay, sissy?

Your main task this time is to purchase four women’s magazines. One must be a glossy, fashion monthly, one dedicted to hair and beauty, one aimed at 20-somethings, with sexy, superficial questionnaires and one a trashy weekly. Buy them all from the same shop in one visit, so it’s obvious they are for you.

You will read everything in all of them, but pay particular attention to hair, make up and fashion advice. Soon you will need this advice. You will complete all the questionnaires. Find three hairstyles, three faces and three outfits that you like and masturbate over each, imagining you are the featured model.

Do NOT cum.

Which magazine had the majority of chosen pictures? You will get every issue from now on. You will subscribe to that magazine, so that it’s delivered to your door with your name on the packaging.

Do not proceed to your next assignment until you have read all your magazines and sent off your subscription.

Your Fourth Sissy Assignment

In this assignment, you will continue to change your attitude.

I hope you are still wearing panties and pantyhose, sissy. Have you cum since your last assignment? Did you find some pretty pictures to look at? If you are a good girl and doing as you are told, you will have been wanking furiously without release. Are you frustrated? Is your boyclit standing to attention?

Don’t worry, you will get to cum.

But you might not want to.

You will buy a dildo, either on-line or from a good old-fashioned sex shop. It MUST be realistically detailed and it must have a pair of balls at its base. It must also be thick.

It needs to be realistic because you are going to suck it. Yes, you’re going to put it in your mouth. And suck. The more realistic the dildo, the more realistic your experience of cocksucking. You want it to be realistic, don’t you? You are going to learn to be a good, sissy cocksucker.

First you will kiss the tip. Then you will lick the tip, then down the shaft. Get it slick with your saliva. Then you will open your mouth and slide that juicy, fat cock between your lips, gently at first, then deeper and deeper until you feel it touch your throat. You may find you gag the first few times, but you will keep going until the balls are banging against your chin and your mouth is stuffed full of cock.

Now masturbate. Imagine you are totally feminised, sucking a real man’s cock. Imagine you are the cocksucker in the picture below. Work that cock in and out of your mouth. Do NOT cum. Smear your pre-cum over the dildo, make it taste like a real cock. Keep going for 15 minutes. Do not cum.

Do this every day for three days. After your third fifteen minutes, you may cum, but collect all your cum in a small glass and smear your dildo with it, making sure there is plenty on the head. Now suck your dildo again for a further five minutes. Make sure you have licked your dildo completely clean and you have emptied the glass. Savour the taste of cum. Imagine it is a real cock; a real cock you have sucked to orgasm and licked clean. How humiliating. A real man would never do that. But you’re not a real man, are you, sissy girl?

Repeat this cycle three times before proceeding to your next assignment. Yes, that’s right, you can cum every three days until then. From now on, you will drink every last drop of your cum.

Your Fifth Sissy Assignment

You are a panty-wearing, cocksucking, cum-eating, sissy slut.

Say it.

Are you proud of yourself?

I hope you’ve been doing your homework. Do you enjoy sucking cock? One so realistic you can feel the head slide over your tongue? Do you like the taste of your cum yet? Do you find it humiliating?

Well, your cocksucking is going to be even more humiliating from now on.

Firstly, you are to increase your cocksucking practice to twice a day, morning and night.

Secondly, you are to watch yourself sucking cock in a mirror.

Thirdly, you are going to wear lipstick. Not just any lipstick. Bright, fiery red lipstick.

What could be more exciting than watching a pair of glossy, red lips swallow a thick cock? And what could be more humiliating than knowing they are your bright, red lips swallowing a large and very realistic cock. Your lipstick will be smeared over your face and down the shaft of the dildo. You will taste lipstick, intermingled with the rubbery taste of dildo and the taste of pre-cum.

As this will be very arousing for you, you must restrict your orgasms to once every five days. This means you must put on lipstick and suck cock in a mirror ten times before you spurt. Is that clear? Will you be able to stop yourself cum? You must.

But first you must buy your lipstick. Don’t forget; buy quality, you are investing in your femininity. The colour lipstick you choose must have ‘fire’, ‘blaze’ or ‘hot’ in the name, so you can’t just rush up to a display and take the first one you see. You will have to read the labels carefully.

Uncap your new lipstick. Wind up the phallic column of pure colour. Face your cocksucking mirror. Run the firm, waxy stick across your top lip.

Press your lips together and see the colour transfer to your bottom lip. Drag the lipstick across your bottom lip, backwards and forwards until the colour is thick and creamy.

Make sure both lips are fully covered, right into your mouth, but not on your teeth. Blot your lips by pressing a tissue against them, then paint them again. This will make the colour last longer. Now begin your cocksucking ritual. Kiss the tip and look at the feminine, red lipmark you have left. You are such a slut! Suck that cock for all you’re worth. Do not cum. Every five minutes, renew your lipstick. Continue cocksucking for at least 15 minutes.

You will do this twice a day, every day, including work days, so you’d better start getting up early.

You may cum three times, once every five days, so do not proceed to your next assignment for at least fifteen days.

Your Sixth Sissy Assignment

Only your sixth assignment? Yet you have already come a long way, haven’t you, sissy?

You only wear women’s panties and you wear pantyhose all the time. You handwash your delicates every night. You’ve bought and read a selection of women’s magazines, one of which you get delivered as a subscriber. You sit down to pee and you’ve become a regular, lipstick-smearing cocksucker. You may well be pleased with your progress, but you could reverse all of this if you changed your mind tomorrow.

To ensure you don’t falter, some more enduring changes are required.

You may have looked adoringly at your nyloned legs and wondered how they would look and feel if you shaved them, like a real woman. Well, my little sissy, you are about to find out, because for this assignment you are going to shave your legs.

But that’s not all. You are going to shave off your pubic hair and shave your underarms. Lastly, you are going to pluck out your chest hairs. I hope you don’t have too many.

Your legs are going to look and feel so much more realistically feminine in your sheer pantyhose. You won’t believe the new sensations without all that hair in the way. If you’ve enjoyed it so far, you’re in for a treat.

You are removing your chest and underarm hair in preparation for your first bra. Oh yes, not only are you going to shave your body like a woman, but you are going to start wearing a bra.

You are going shopping again. You will return to your lingerie store and buy a black, lacy, underwired bra and matching panties.

Make sure the bra will fit you. Don’t guess your size, ask to be measured. Don’t forget, the assistants already know you wear lingerie, so there’s no need for any new embarrassment. Buy three more pairs of panties to expand your collection.

You will also buy two nighties; one a very short, babydoll style, one at least knee length. Both must be silk, satin or a polyester mix so thay will be slippery on your skin and over your pantyhose.

Wear your new bra and panty set one working day each week.

Continue to wear panties and pantyhose every day.

Wear one of your nighties with pantyhose and panties every night.

Increase your cocksucking practice to three times a day, always wearing lipstick.

You may only cum once a week.

Shave your legs, pubic and underarm hair every two days. Pluck your chest hairs every week.

This is a lot of new work. To make sure you are well settled into your increasingly feminine regime, you may only proceed to the next assignment when you have successfully completed four weeks homework.

Your Seventh Sissy Assignment

I hope you are doing this properly.

To get this far, you have shaved your legs at least fourteen times, put lipstick on over a hundred times and sucked cock so often you are a pro. You own at least six pairs of panties and a bra, which you’ve worn to work at least four times, and you should still have seven pairs of pantyhose if you’ve been replacing all the damaged pairs.

And that happens so easily doesn’t it? Pantyhose are so delicate, especially the sheer pairs you are forced to buy. But it’s worth it isn’t it? Have you worn five denier on your shaved legs yet? Deliciously feminine, aren’t they, sissy? But so delicate. By now, you’ve almost certainly had to wear a damaged pair for hours on end. Not any more.

From now on, you will be more ladylike and always carry a brand new pair of pantyhose with you, in their packaging, no matter what you are doing. You will also start carrying your lipstick around with you, too. You never know when you might need it. Soon you will need a handbag for all the things you will be made to carry around with you, just like a real woman. (A handbag is a purse to you, Miss American sissy.)

You are going shopping again, sissy. To prepare for your trip, make sure your body is very smooth. Wear your bra and panties and your sheerest pantyhose. You can choose the colour, but make sure you are carrying spare pantyhose and your lipstick. You will also take your dildo. I guess you’ll be needing some kind of bag. See how useful a handbag is?

Wear a white shirt, a suit and tie and a pair of shoes. Don’t wear socks. Don’t wear an overcoat, even if the weather is poor. Your black, lacy bra will be visible through a white shirt won’t it, sissy? Nevertheless, you will do this.

Park well away from the shops.

The first thing you must buy is a handbag (purse in the US). Something that will never be mistaken for a man’s bag. Something quite dainty, but large enough for all the things you will soon be carrying at all times, like your spare pantyhose, a make up bag, pantyliners and your dildo. Buy a nice, little, zip up bag to keep your make up in, too.

You are going to buy nail polish, because from now on you are going to be painting your toenails. Shaved legs, painted nails and pantyhose. How erotic, how feminine. No real man does that. You must be such a sissy. Imagine how you’d feel if someone saw your feet.

You will buy three bottles of nail varnish; one clear, one clear but glittery and one bright red. Don’t forget some remover, some toe spreader sponges and little cotton wool balls.

Make sure you buy a new, red lipstick to match your nails; that old one must be nearly worn out.

You will also buy a very subtle lipstick in a colour called ‘nude’ or ‘birthday suit’ or something similar. Again, remember to buy quality, you are investing in your femininity.

You will buy a little compact mirror. Every girl has one in her handbag for checking her make up. You will so enjoy checking your make up in public.

Lastly, you will buy a pack of pantyliners, the type with wings. Make sure they are heavy duty.

You will then go to the nearest men’s room and put in your first pantyliner. Position it in the gusset of your panties and tuck your cock between your legs, against your pantyliner. Bend the wings over the edge of your panties to hold the liner in place.

Put on your new, red lipstick in your new, compact mirror. Blot and reapply three times. Make yourself pretty, because you’re going to cum, but it’s the last orgasm you’ll have for a long, long time.

You want to look your best for such a memorable occasion, don’t you?

Suck your dildo, looking at yourself in your compact. Now cum in your pantylined panties, you cocksucking, panty-wearing, feminised, sissy girl. Make it a good one, because it’s your last. Don’t clean any of it up. Pretend you’re a slut who’s just sucked her boyfriend before he fucked her in the toilets and his cum is now leaking into her panties.

Remove your red lipstick and replace it with your new, nude lip colour. Walk back to your car in your cum-soaked panties.

Do not move on to your next assignment until you have done this. If you don’t think you can do this, you certainly won’t manage the next assignments. And you do so want to be feminine, don’t you sissy? Your eighth assignment is beckoning…

EMAIL with your report.

Your Eighth Sissy Assignment

Have you REALLY completed your seventh assignment?

No cheating, please. Go back if you haven’t done exactly what you were told.

You are an eager, sissy cocksucker, aren’t you? Did you enjoy your walk in cum-soaked panties? Did you feel feminine? Did you feel warm between your legs? Did your heavy duty pantyliner hold it all, or did some of your cum run down your leg, inside your pantyhose, leaving a dry crust? Did you feel dirty?

From now on, things are going to get harder. Except for your boyclit, that is…

You bought three bottles of nail polish, didn’t you? Now you’re going to start using them. From now on, your toenails will be permanently painted. You will give them three coats of red, then one coat of clear. Every four days, after your shaving ritual, you will remove and renew your nail varnish. Your feet will look so pretty; shaved smooth, with bright red nails inside sheer pantyhose. You won’t want to hide them away for long. You’ll need some delicate, strappy, high-heeled sandals to wear so everyone can see your pretty feet. You will also have to start looking for pantyhose with a sheer, sandal toe when you next buy a pair, won’t you?

It’s about time you expanded your wardrobe.

You will need to get ready for your little shopping trip. You will make sure you body is smooth and hairless. Your toenails will be immaculate in red. You will paint your fingernails. Not red; at least, not this time. Use the glittery polish. See how girlish it makes them look. Subtle, yet obvious. This must be one of the most frightening, sissyish things you have done, don’t you agree?

You will wear your black bra and panty set and black pantyhose. You will wear a white tee-shirt, a jacket, a pair of jeans and a pair of shoes. To make sure you expose your black, nylon ankles, you will fold a 2″ turn-up into your jeans. Don’t forget your handbag, either.

Apply three coats of your nude lipstick. Don’t forget to carry it with you, along with your spare pack of pantyhose. Now you are ready. Visible hints of lipstick, nail varnish, bra, pantyhose and a handbag. Quite humiliating for you, isn’t it, girl? Every woman will know you are a sissy. Some men will probably notice, too. But teenage girls are the worst… very observant and very cruel. Let’s hope you don’t meet too many.

You should know your sizes in women’s clothes by now. You are going to buy a pair of women’s slacks. Again, remember to buy quality. You are investing in your femininity. Buy a black pair with a non-elasticated waist and a side or rear fastening.

You will also buy a blouse. Look for a delicate, floral print, short sleeves and a feminine collar. Try to get a rear, or shoulder, fastening.

Next, you will buy a pair of high-heeled sandals. These are so trendy you will find them everywhere whatever the season. Unless you are blessed with small feet, you may have to compromise on the ‘buy quality’ rule to get whatever you can. However, you should be able to squeeze into a sandal one or two sizes too small if you can’t find your size. A lot of cheap shoe stores have a good range, so you can afford to experiment…

imagine these are your feet, sissy. Soon, soon…

Look for wraparound ankle straps, so the heel is ‘open’; tall, slender heels; no platform soles. The sole should be thin and delicate, with just a few straps attached to it. The sandals in the picture above are exactly what you are looking for. Go for pink, red or black. Do not buy white. You are a sissy, not a tart.

Your feet will look like this by the end of this assignment…

Don’t forget, your appearance will scream ‘sissy’ to any women, so don’t be embarrassed to ask to try something on. The assistants will probably expect you to ask, or even suggest it to you. Just imagine taking off your shoes to expose your bright red toenails, encased in black pantyhose.

Lastly, buy a pair of nude, knee high stockings and a bag of millet or similar bird seed.

By now, you should be carrying a collection of bags from women’s stores, adding to your sissy appearance. Go to the nearest men’s room. Pour a good handful of birdseed into each stocking, twist the stocking and fold it over itself, then tie a knot. Remind you of something? You’ve just made your first pair of breasts. Fit them inside your bra, so that the knots are pointing out like erect nipples. You may need to adjust your bra straps to allow for this new weight. Does it feel good to have your first pair of breasts? Change into your new blouse and slacks. You will walk back to your car like this.

You have now completed your eighth assignment. EMAIL with your report.

You will continue to masturbate but you will not cum.

You will continue your cocksucking practice three times a day.

You will always wear panties and pantyhose, like a good sissy. You will wear an unfilled bra at least once a week.

You will continue to keep your body smooth and hairless and your toenails painted.

You will wear your new shoes around the house every waking moment.

Your Ninth Sissy Assignment

Now that you have bought yourself a nice, casual, feminine outfit, you have the perfect costume for another shopping trip.

Yes, you are going shopping again and this time it’s going to be very special.

You will be completely, freshly shaved. Your toenails will be red, your fingernails will be glittery. You will wear black bra and panties, nude pantyhose, your floral blouse and black slacks and subtle lipstick. You can wear men’s shoes, even though they will look so out of place. You will carry your compact mirror, both your lipsticks, spare pantyhose, your high-heeled sandals, your dildo and your breasts. Aren’t you glad of your handbag, sissy girl?

Copy out the following shopping list in your own handwriting –

– delicate, feminine watch (this need not be expensive)
– two piece black suit – long sleeved jacket, short skirt. Must be lined.
– skimpy, white vest top
– good quality perfume. Try a few and find one you like.
– make up kit. You want products to match your skin tones and skin type. Most – department stores will do a selection of make up in a gift set, which will make your life easier, but you must buy –

– liquid base
– powder foundation
– blusher
– a selection of eyeshadows
– black and brown mascara
– black and brown eyepencil
– eyebrow pencil
– set of applicators
– eyebrow tweezers
– eyelash curlers

You are going to look so hot.

When you have completed your shopping, find a quiet rest room, maybe in a department store. You know what’s coming next don’t you, girl? I hope your hair isn’t too masculine or this will be really humiliating.

perhaps this is how you’ll look?

Hang your new suit on the back of the door. Put your sandals on the floor. Take off your shoes, slacks, blouse and lipstick. Fit your breasts into your bra cups. Spray a little pefume on your wrists and rub them together. Spray behind your ears, between your breasts and between your legs, too. Isn’t it good to smell like a woman?

Put your vest on. Does it emphasise your cleavage? Now put your suit on. Relish the sensation of that slippery lining on your pantyhose. Let’s hope your boyclit doesn’t stick out too far, girl. Maybe you can tuck and a liner will prevent any nasty stains. Put your sandals on. You will be thankful for all the heel practice you’ve had at home.

Do you look hot or what?

Now it’s time for your make up. It’s your first time so you’re not going to use much. Less chance to make a mistake that way. Press a little of the powder all over your face, using a rolling motion with the pad. Position the eyelash curlers at the base of your upper lashes and squeeze for a few seconds, then release and gently squeeze again a little further out.

Hold the mirror at your chest so you are looking down into it. Now apply mascara to the outer two-thirds of your top lashes. Next, apply a coat of red lipstick and blot. Now a second coat of mascara, then a second coat of lipstick and blot. Now do your bottom lashes whilst looking up at the mirror. Add a third coat of lipstick, for luck.

See how long and feminine your lashes look. Don’t your eyes look sexy, sissy girl? And that’s without eyeshadow or pencil. You won’t be using them today because they take practice. Don’t worry, girl, you’re going to get lots of practice.

Put your watch on. Despite what you’re wearing, does that not make you feel even more of a sissy?

Now pack up your stuff and present your ‘smart office girl’ look to the world. How long do you think it will be before you are dressing like this for work?

You will not cum.

Go to a bookstore and buy a book on hair, make up and beauty. You are going to read this from cover to cover when you get home.

EMAIL your report. You must have a lot to tell…

From now on you will wear a bra, panties and pantyhose on your shaved body every day and sandals every moment at home.

You will maintain red toenails and will also wear clear polish on your fingernails. Always. Hopefully, you have been using your initiative and letting your fingernails grow.

You will apply your new perfume to your wrists and chest every morning.

You will continue your cocksucking, but only once a day now. Every evening you will wear one of your two female outfits and apply full make up before sucking cock. This will give you daily practice at doing your make up. Believe me, you will need it. Most real girls have been experimenting with make up since long before puberty, so you have a lot of catching up to do. Try a different look every day. Remember, you are a sissy, not a tart. This goes for make up more than anything. A girl must learn to have a light touch.

Satisfy yourself that you can make yourself up proficiently before you progress to your next assignment. This is very important.

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.


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 tanlines, front and back.


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, sissygirl.

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

Do not cum.

Your Eleventh Sissy Assignment

Hello, my bra-tanned sissygirl. 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 cocksucking 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 buttplug. 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 colours is up to you.

Take your sissy, feminised self to a sex shop and buy not one but three buttplugs 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 buttboy?

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 buttplug. No real man would even dream of doing this. You are such a sissy.

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 feminisation 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 colouring



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 buttplug 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 coloured. Obviously, this will depend on your current colour, but there is little to touch a strong henna red or a soft, chilli purple for outright femininity.

You will be offered a huge choice of colours 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 glassfibre 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 boyclit 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 feminised sissy girl. Give up your last pretences 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 feminised man, ‘forced’ to do things against your will? Perhaps you need some more assignments, then.

Your Thirteenth Sissy Assignment

You’re not superstitious, are you, sissy?

So, you are seeking forced feminisation 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 feminised 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 feminisation. 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 centre. 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 tantalises your sissy mind, doesn’t it, girl? What are you waiting for? Email your report.

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 feminise 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…

Email your choices, or a better one, if you have one.

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 jewellery

– 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.

EMAIL with your report.

Your Sixteenth Sissy Assignment

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

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 colours 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 jewellers. Jewellery 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 jeweller 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 jewellery, you can do the rest of your shopping.

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

a helpful shoe shoe assistant

…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 colours 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 colour.

– three white blouses, cut like shirts but with the buttons on the ‘wrong’ side for a man (but the right side for you, sissygirl).

– a roll-neck top in a bold colour.

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

Can you guess what’s coming next? Not your sissy boyclit, that’s for sure!

Go to your favourite 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 colour, 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 opaques 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 favourite 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 jewellery 24 hours a day, EVERY day.

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

Catherine exposes her ankles

Your Seventeenth Sissy Assignment

You have been deprived of a lingerie experience, haven’t you, sissyslut?

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


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 buttplug, 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 jewellery, 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 jewellery. 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 favourite 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. 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 opaques, 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 boyclit. 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 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 jewellery, perfume, nail polish and full, heavy make up, of course. And your biggest buttplug.

Masturbate until your boyclit 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 boyclit, like a large, nylon condom. Pull it right down over your sissyballs. Twist the stocking behind your sissyballs 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 boyclit covered in latex and nylon and three layers of nylon compressing your sissyballs.

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 boyclit and sissyballs 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 sissyballs 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 boyclit, 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 cumslut?

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, sissygirl.

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 cumcube 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, jewellery 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 cumcubes. Deliciously humiliating.

It should take you at least two weeks to use up your cumcubes. If you enjoy the taste of your cum after your cocksucking training, then you may find your first, frozen cumcube 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 Twentieth Sissy Assignment


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 boyclit and sissyballs 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 boyclit becomes slick with pre-cum. Wear your palest slacks and a sissy blouse.

Is your bound boyclit 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 jewellery 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.

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, apologise 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.

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

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, clutchbag 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)

– babydoll 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, sissygirl, 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 22nd Sissy Assignment

Drabtime. Is it joining the list of words that occupy your mind, but you can’t tell anyone about? Like cumcubes? Boyclit? Sissystation? Or even cosmetic companies, hosiery firms, lingerie brands, nail varnish colours. Have you casually mentioned something in conversation and realised you read it in one of your women’s magazines? Have you overheard a group of women talking about blowjobs and wanted to comment on your own experiences? If so, you should be congratulated on being an advanced sissy.

Are you completely dressed as a woman, as required in your last assignment? If not, I hope your drabtimer is running. That’s a good name for it – ‘drabtimer’. While you’re sitting at your computer, make a nice, printed label for your new clock of shame. Then you’ll have to explain what a ‘drabtimer’ is to anyone who sees it. What a secretive life you lead, sissygirl.

Your new assignment was suggested by a sissy reader. You’ve put yourself through some enduring changes to your body, haven’t you, sissy? You shave like a woman, paint your nails, pluck your eyebrows, got your ears pierced and even got a bra tan which lasted a long time.

This time – well, let’s get you dressed first.

This assignment will take you over your drabtime allowance, so you will have to dress as a woman – the minimum standard applies, of course. You see, you’re going to a tattoo parlour to get a pretty tattoo. A pretty, feminine, sissy tattoo to advertise to anyone that sees it ‘here is a sissy’. And you’re going to go dressed as a woman. Face it; the tattooist will see your sissy body and feminine underwear, so what does it matter?

A tattoo is for life, so choose wisely (grin); not just the design, but the artist. Make sure they meet your nation’s standards for hygiene. You can choose from three locations for your sissy tattoo – shoulder, buttock or pubic area (where you are neatly shaved). Your design should be something like a flower (but not a rose) or a butterfly or, for the particularly brave, the word ‘sissy’ or ‘slut’.

While you’re there, get your navel pierced. Very slutty. At least, it is on you.

Don’t forget – drabtime. The rules apply 365 days a year. No arguments.

Your 23rd Sissy Assignment

This is your most serious, ‘real world’ assignment yet. Are you ready for it?

Do you realise you spend more time dressed as a woman than as a man? At least, if one is generous and includes your nights. I bet you hate wearing drab to work. It seems a shame to waste all the emotion, energy, money and time that has gone into your femininity by just sitting around at home in a dress and hiding your feminised body in dull, male clothes. You must get another job in your free time.

As a woman.

Or rather, dressed as a woman; you wouldn’t want to defraud anyone, would you?

Do not read on if this idea hasn’t already crossed your mind. You’re not ready.

Buy a local paper (remember: drabtime!) and check through the ‘situations vacant’ columns. What would fit around your current work commitments?

Healthcare worker?




Maybe even Saturday assistant in a hair or beauty salon? If you have qualifications, why not try for a more skilled job? Don’t deny your fantasies about being an office girl; smart suits, heels, lots of make up and flirting with guys.

But for now, concentrate on the more menial jobs listed above. These are likely to require you to adhere to a female dress code or even wear a uniform.

Oh, yes. A uniform. Even the word has you tenting your panties and touching yourself, doesn’t it, slut. Uniform. Your uniform. It formalises your feminisation. A dress code even stricter than that to which you have been subjected in these assignments. It is the thought of wearing a genuine, women’s uniform to work that will, ultimately, drive you on to complete this assignment. You know it’s true.

You will ring up about a few potential jobs; find out about the hours and typical work if the ad isn’t clear. Be realistic with what you could commit yourself to. This is FOR REAL and other people’s livelihoods could depend on your actions. You must ask if there would be any objections to you dressing as a woman at work; after all, this is what you want. You could explain you are contemplating gender reassignment without stretching the truth too much. Perhaps it’s a second job to earn money for breast enhancement. You’ve probably thought about it, haven’t you, girl? After all, no real man would do any of the things that make up your daily routine. But you’re not a real man, are you, sissy? True, you’re not a real woman either, but you’re trying hard.

In this politically correct world, you probably won’t be surprised at how many places will consider you for work and send out an application form. You may be excited that someone is willing to consider you working for them dressed as a woman, but in reality you’re just another pair of hands. Yours just happen to have long, painted nails.

If you get an interview, go dressed appropriately. You don’t need to be told what to wear at this stage, do you sissy? Take your interview seriously. Do not waste their time. If a post is offered, accept it. Take rejection gracefully, even if your interview was clearly only for their entertainment and very humiliating. Remember you have more to loose than your employer does; they know who you really are. Besides, you like humiliation, don’t you, sissy? That’s why you’re reading this.

When you finally accept a post, DO THE JOB, at least for the minimum trial period.
EMAIL your proposed career (with details), interview date and proposed interview outfit. Truthful reports only please. I grow weary of fantasy bullshit.

Good luck and enjoy it; a nyloned, spike-heeled foot in the door of feminine employment; honest but menial work.

A word of warning. You must NEVER touch your boyclit while wearing your uniform, even in the safety of your own home. If you do it once you will be tempted to do it again, subconsciously at work. Your colleagues will think you are a pervert and your employers will not tolerate it, so be ladylike and keep your hands off. You have been warned.

Practice, practice, practice…

Your 25th and Final Sissy Assignment

Are you enjoying your new job? Do you have a uniform? Is it pretty and feminine or plain and functional? Do your new colleagues accept you? Do they treat you like a man or a woman (although you are neither)? Have you thought more about having a sex-change for real, now you’ve had to pretend you want one? Would you like to be rid of that boyclit and those nasty sissyballs and have a pussy of your very own? Maybe you’d like a pair of real breasts, too?

It’s time to stop beating about the bush. You are not a man, you never were a man and you never will be a man. You are a sissy and you yearn to be accepted as a woman. For your 25th assignment, you will stop wearing male clothes.



Not even to meet your family or any other flimsy, avoidant excuse you can come up with. Your drabtime rules still apply, but from now on ‘drabtime’ refers not to ‘male outerwear’ but to any outfit of women’s clothes that doesn’t meet the minimum, feminine standard. You remember the minimum standard, don’t you? You should have it memorised by heart. Recite it out loud now.

If you have to go to work in drabtime, you will have to dress completely in women’s clothes, but this does not have to meet the minimum standard. For example, a blouse and slacks, bra and panties, hose and loafers would be a pretty, feminine outfit which does not meet the dictated standard, but may well be suitable for work. If your ‘male’ workplace dictates you wear a uniform of some description, you will have to be creative, or face a massive tally of forfeits. Alternatively, there may be a female uniform you could wear.

You may think I am joking; I am not.

You WILL wear women’s clothes 24/7.

Now, obviously this will take some planning, so you have one week to buy a more extensive wardrobe of women’s clothes. One week from today, you will collect EVERY LAST ITEM of your remaining male clothes into bin bags and take them to a charity shop where you will donate them. Make sure you are nicely dressed, sissy. After all, you wouldn’t want to waste your drabtime on such a simple chore, would you? Perhaps you (a well-dressed woman) could explain they are the clothes of a male friend who has left your life forever. That would be true enough, wouldn’t it?

Email your experiences of life permanently dressed in women’s clothes.

58 Responses to “Sissy Assignments”

  1. Kimmy Says:

    I’d love to see this be reposted somewhere.

    I had just finally had the chance to start this program, and am now on step 2, and I want to see how far I can get along with it.

    I’d also love to see a few steps be added.
    Maybe a simple step with requiring that the smoothing the skirt motion before sitting be required EVERY time the sissy will sit, regardless of where/when or how dressed.

    With a little imagination, this list could be re-published and be a HUGE hit for your site.

    Please email me when you get it re-posted.

    PS: Some pics and formating were saved on another blog…

  2. Rita Says:

    Lately I have given serious thought to feminising my boyfriend, and what started this was when I found him dressed in one of my friends clothes and wanking into one of her stilettos boots!
    You have made up my mind for me, thar way I’m am going to do this- exactly how you have explained it in this post.
    I might even send an up date.

  3. Kimmy in RI Says:

    Way to go Rita!

    Look forward to hearing any reports or feedback.

    Too bad you didn’t see the original posting at Sissy Station, as the pink/white text & black background, and complimenting pictures added a lot to the feel of these steps and the process.

    Plus there was a thrill of having to click “Yes I’ve done this, I’m ready to go to the next step”

    And that added some psychological appeal and acceptance of what you had done, and are intending to continue doing.

    But good luck!

    • Rita Says:

      I must check that out as I think I’m really going to enjoy this, I trusted this guy and gave up a lot for him, just to let me down.
      I think it would be no harm for him to give up something, his maleness I think is a fitting sacrifice, a girl must get some bit of fun.

      My friend who’s clothes he was wearing actually works with him along with a few more of the girls, so they are going to share in the fun as well, along with making sure he completes each assignment.
      Reading some of the assignments I really do think I’m going to enjoy this, like send him in to 7 pairs of nylons, I can think of a few shops he is def going for those as I know some of the girls in their and I will make sure they will be expecting him, also when he has to buy his skirts and shoes.
      Interviews he is def wearing a skirt suit.
      And nights out I can’t wait!


    • Rita Says:

      Well these assignment have been so much fun not just for me but for the girls in the office and in the shops where he had to carry out his assignments.
      Before he did anything I told him if any one asked him a question he had to be truthful or I would make him do all assignments in the one week.
      So before he went shopping I told my friend that works there and I told her to be very helpful 😉 and that she was!
      It began suttle the first day, when he thought he was getting away unnoticed until he got to the till to pay.
      There was quiet a few in the que, he got to the till and was getting ready to pay, Ciara asked the question- are these for Rita the seem a little too big? She shook his head, she asked who are they for, he reddened up and said they are for himself, Ciara appeared surprised and said stuff like- are you getting in touch with your feminine side and dose Rita know? At this stage people in the question were getting impatient, so Ciara shouted to Susan further down the shop, if she wouldn’t mind helping Dermot, he is looking for knickers for himself and the ones he has a probably too small, she said – no problem send him down! Almost everyone in the shop was looking at this stage.
      Susan measured him up and gave him choices, he went and paid for them and headed away red from ear to ear.
      The girls said they really enjoyed it and they were looking forward to his return.

      When he went back for the pantyhose they really helped him, but not to mention when he went to buy his sheer pantyhose and bra with matching knickers, they measured him up recommended loads, through the whole thing a nice croud of inquisitive ladies gathered around, not to mention that one of them was our neighbour, she got a real kick out of the whole thing.
      Now sorry but we went through some of the assignments quickly and maybe mixed up a few.
      This is where he is at so far, we sent him to buy the dildo, now that was fun watching him use that, I have told him I’m not having sex with him anymore all all I’m going to use is his dildo, he is allowed to watch but he has to wear his lingire and pantyhose, he is not allow touch himself during this.
      I sent him back to the shop for his high heeled sandals, wearing the white tee shirt.
      Susan and Ciara again gave him endless help along with disposing if his male shoes that he went in with.
      We are actually so lucky as Dermot it an it guy in an office block with 16 employees an all 16 are female! 3 of whom are very good friends with me. Even his boss is female, Maria is her daughter and asked her did she mind if Dermot began wearing girls clothes, she was hesitant and said ok once it dose t effect work and that we don’t miss deadlines.

      So I’m sorry if we speeded up some assignments but the girls couldn’t wait.
      This past week the only male clothes he has worn is his pants and shirt.
      The girls took him to the hairdresser, his hair was always slightly long so she gave him a bob style or as we like to call it, Kim marsh style. The for a facial complete makeover, hair removal eyebrows – the lot.
      He has worn a selection of items each day always sheer pantyhose, matching lingire panty liner butt plug a slightly bigger one each day, shoes vary from heeled sandles to courts at the moment the heels are two inch and on Friday his first three inch heel.
      Here is where it gets good, it’s was Theresa’s boot I caught him wanking with and she also works there, so I have told her that the only time he is allow cum during the day is when she allows it, we’ll it is only fair as it was her new stiletto boot he violated.
      After cumming the girl in the office then vote as to what happens to sperm afterwards.
      He is well monitored each day so no chickening out.
      His boss was really impressed with the work output and said this is a good thing and that she saw the girl were actually enjoying working there, she said this can continue but only if they dress him properly and he is passable as a woman, as she didn’t want the business to appear like a circus, he is sooooo frustrated with the whole set up, but no turning back now, well especially after shopping lastnight and this morning. As you can imagine the shops are packed at the moment with Christmas shoppers.
      We are just back after buying him his first skirt suit or should I say suits, 5 a different one for every day of the week.
      He also now own 5 pairs if 4inch stiletto courts especially for work.
      Susan and Ciara were again more than helpful again.
      We spiced thing up a bit by getting him a selection of garter belt and sheer nylon stockings.
      While we were shopping Theresa Aisling and Jacqui, went to our house and gathered his male clothes and left them in the front Halway for him to take them to the charity shop. The had this done a just joined us.
      Susan gathered his male clothes and disposed of them.
      Ciara suggested crotchless knickers she help him put them on teasing and tormenting him as she did so, as she bent down her face close to his boy clit her hair glanced along the tip his body shivered, she guided his boyclit through the slit in the lace knickers give it a few intentional tugs.
      She then got an idea, she went behind him, put her hand out between his legs caught his boyclit and bent it straight back between his legs then told him to close his legs and td him to walk a few steps without allowing it to pop out I front and that if he did she would make him walk out of the dressing room and into the shop I front of everyone.
      He managed to keep it back and my god did he walk with such grace so feminine.
      So our minds were made up that was how he was going to walk to the car.
      We got him all dressed, matching black lace (crotchless) knickers, garter belt, and bra, stuffed with a nylon stocking and bird seed, sheer tanned nylon stockings, pencil skirt that stopped a few inches above his knees, and matching jacket, boy clit turned back Nd away we went.
      We stopped for a cup of coffee, as he sat down and crossed his legs (as ordered by us) you could just see his stocking tops and from the right angle underneath you could just see the the top of his boyclit.
      We headed off after that to the car as he thought but intact to do more shopping, I lagged back to have a look, and began to smirk as he walked so feminine as he had no choice to avoid give away bulge in his pencil skirt as they are definately unforgiving to bulges.
      It was then I noticed that to top of his boyclit was slightly visable at the top of the slit in his skirt, but the ting was as you know some pencil skirt ride up a little as you walk and unfortunately this was one of those so after a while the purpleish reddish head of his boyclit was getting easier to see again from take certain angle.
      With his new hair style makeover and outfit it was no problem to mistake him for a woman.
      It helped that his build is quiet small. So if a bulge appeared he was screwed.

      He turned to me and asked if he could stop walking for a while, I asked why are the shoes hurting, he blushed and said no, that he was almost at the point if cumming, I aked how, he said he didn’t know but that because he’s was walking with his legs so tight together the butt plug was causing a funny sensation, along with the side to side movement of his penis as he walked, pluss Ciara pulled back his foreskin completely, this caused another sensation at the top as it rubbed his stocking top.
      I smiled and said- you mean if you stay walking as you are you will ejaculate.

      I told Theresa she linked hands with him and said said Dermot dead your are going to experience you first public orgasim.
      He was reluctant to walk as he had told me earlier that week about the anticlimax after fuming and the was he felt guilty and ashamed.
      Theresa told him, it like this the antiimax will pass, and that she was going make him do this even if it mean exposing him so he may as well enjoy it.
      They started walking, we were close behind as i wanted to see this , he told later what Theresa was saying, well did you ever thing the day you were fucking my boot that you would be walking down the Main Street of a city dressed as a girl linking arms with me and while spilling your sissy juice over you legs and the street.
      So there I was watch two women walk down the Main Street if our local city linking arms, except one of them was my sissy boyfriend (soon to be ex) all dressed up so feminine with his cock tucked back ready to cum walking alongside one of my friends that he fantasised over.
      His walk changed slightly he wanted to stop but Theresa kept him walking, she said he whimpered slightly and his eyes rolled a little, she asked did he want her to stay talking through the sole thing and he nodded and siad he wod love her to, and so it began it was clear to see ropes of seimen shoot out from under his skirt some on his legs more on the back of his shoes and the majority left a spotted trail on the street.
      I could not believe the amount and how long it lasted it must have lasted a good 14-15 paces with a spurt for each pace, we hagan to giggle as did Theresa.
      When it was over she turned him around and we walked back over it to see it, each of us stepping on his sissy juice, including making hi also step in it.
      Oh what fun we are goin to have during Christmas not to mention the Christmas party.


  4. kyra t Says:

    i am sitting here in a jog bra and panties and i am not doing any of this gay stuff.


    • kimmyinri Says:

      Tom if you’re being pushed to do these assignments, you might want to rethink those words.

      You agree to do one step, and it seems impossible to agree, then it becomes normal. Just something you do.

      The next step seems impossible…at first.
      But in a week or so, it too will feel normal.

      After awhile, you pass the “point of no return” and accept that you’re destined for a life in skirts on your stocking covered knees.

      It’s just how it works.

  5. graham Says:

    yes it was a year now thhat i was turn into a sissy girl i have breasts like a girl frist time i put on a bra and panties i had to wear for a week then one day i strated to wear them all the time next came a blouse i wore to work one day the lady boss call me into her offcie when i went in she told me to sit i did as told she told me if i want to wear women clothes it was fine with her but there one rule i ask her what the rule was she told me to sign this paper frist i did as told i sign her paper good girl now stand up and remove your pants i did as told i was glad that i was wearing thong panties they were red that match my bra she look at me and said remove your blouse i did now i was standing only in my panties and bra yes you are one male i know that like women clothes i ask if i could get dress she said no i have some thing for you to wear but frist put this from in your bra it will help you look more like a girl for now now came a dress it was a short dress after i was dress she told me that the way i be dress all the time then she said at lunch time we willl go and get new clothes
    at lunch came we went shopping she toke me into a lady store told the lady that she need some new clothes for her the lady ok what size is she my boss said you have to mearure him the look on the lady yes him he my bitch and i want him in dress as a girl well then i be happy to make him your sissy bitch girl is any thing you want are bitch in i have a maid outfits collars butt plugs ear rings i think you should get a maid out fit for home and a shorter dress for work and a butt plug so his ass is always ready for your dido cock you have one she said i never thought of that you mean you have not made him suck a dido yet no well she went and lock the door she told me to sit down then she told my boss to open up her pant and them down she was wearing a strap-on dido she said look as my boss look she put the dido in my mouth i strated to suck she told me that it ssuck my cock see your bitch like it now put on a strap-on take over hereshe did as told it last all after noon now its been a year since then i now a full time sissy girl i must go now my master boyfriend need me to wash his back and cock maybe i just wash his cock with my mouth

  6. Kimmy in RI Says:

    Oh come on Tom!

    You can do better than that.

    What colors did you get? What cut?

    How did wearing panties that first day feel?

    Did you find yourself starting to forget that you were wearing them during the day?

    I bet you did, and that’s the start of it becoming normal.
    That’s the start of your body telling you, it’s ok to open up your fem aside a little, it’s ok to like wearing panties. The next step is when it no longer causes you to get an erection or feel sexually stimulated. By then it’s too late, and you’ll find that you’ve already started picking out and being drawn to your favorite pairs, a cut you find more comfortable for example, or a color that you feel “happier” in.

    You’ll see soon enough I’m sure, I am almost jealous of the journey ahead.
    Kick and scream now…if you must, but in the end just kick back and accept it, and enjoy the ride.

    Until then, keep up the posts/reports…oh, and…

    Welcome to the panty wearing world!

  7. Kimmy Says:

    Sounds like a lot of progress was made in just 2 weeks or so.

    But I’m glad you and your girlfriends are enjoying this.
    Would love to hear follow up reports.

    Does the clothing sexually arouse him?

    If so, do you ask him to imagine being a pretty girl at a fancy dance, and realize she is wanted by every guy, and then describe how soon she will be on that dance floor, and just as you have ensured he is in panties…you’ll ensure he isn’t a wall flower too !

    Being around men while dressed will inevitably lead to dates with men.

    Dates with men usually have the guy pay all the bills, and will leave him vulnerable and pressured to pay him back.

    And that’s is where the “final” conversion will come…full submission to a man, and acceptance of his new role in life.

    Keep it up.

  8. tom Says:

    i don’t even know why i came here to begin with…

    i think i bought bikini cuts?

    i bought two pairs of white and two pairs of pink cotton panties. i also bought one each of white, pink and red satin panties all trimmed in Black lace.

    the first two days i wore them to work under my clothes i was so sure everyone would see my stiffy. on day three i was soft by lunch knowing that i was safe and not discovered. now i don’t get hard at all wearing them. my favorite pair is the pink and Black lace satin panty.

    i can’t do assignment #2…how can i wear pantyhose at the gym? not doing that…


  9. chloe Says:

    Hi i am a very submissive sissy who like all sissies just love humiliation i would love a rg to push me on


  10. Kimmy in RI Says:

    There are lots of submissive sissies, and few willing doms that want to push/force or even blackmail the sissy into becoming all the girl she can be.

    But for those of us who hear that inner call, but have a little fear of “just doing it,” we always seek the right guy/girl that will take the choice OUT of our hands, and leave us without any escape from our future in short skirts.

  11. james Says:

    Love the thought of going to a dancewear shop for tutu and tights. Not had anyone order me to do it yet.

  12. Debbie Says:

    Wow thanks.. Going to turn my boyfriend into the sissy boy he really is. Let you know how it goes!! Hugs and Kisses!!

  13. Nikki Says:

    I’m so glad I found this! I’m an experienced tv who dresses a lot anyway but I just love following these assignments. I now only own panties, bras and tights and wear them all the time. I’ve been folowing the rules for the next couple too and am now really looking forward to the second half of #6 then #7 and 8 🙂

  14. tom Says:

    ok, so i can’t deny myself and want to start again…should i start back at the beginning?

    • KimmyinRI Says:

      Yes, at the beginning.

      But try to add a few and be more daring.
      Include one where you sit to pee.
      Include one where you watch an hour of hypnotizing cumslut TG videos per day.
      Then double it!

      Stuff like that.
      You’ll see….there isn’t any escape from this.
      It’s your life now, plain and simple.

      Or else why would you return?

  15. tom Says:

    ok. had to go buy new panties since i threw the last ones away. started wearing them today.

  16. Nikki Says:

    I just wanted to thank you soooo much again for sharing this. I’m typing this sat at work wearing my black bra (unpadded), thong and suspender set, black sheer stockings, black women’s trouser suit and cream pinstripe blouse, 3″ stiletto courts, perfume, light makeup with red lipstick and nail varnish, earrings, jewellery, hair in a feminine ponytail and my handbag under my desk thinking about how far I’ve come and how much I love this. I think i might wear a skirt to work for the first time tomorrow!

  17. sissy bun Says:

    it now two years i become my boss sissy bitch in that time she had a baby and i become the mommy i look after the baby yes i did it all and her boyfriend told her its to bad are sissy do not have breasts milk she said yes but the baby can suck her breasts after i feed her i just put the baby down when he walk into my room i just had panties on he walk up put his hand on my ass i see my bitch need some thing he turn me around and i was on my kness i pull out his cock and shove it in my mouth and suck that my bitch just then she came in well what have we here my bitch sucking my man cock that nice but i want her ass to play with

  18. Mike Says:

    Stumbled onto this awhile back but never considered doing it until yesterday. I saw my coworker’s visible panty lines (a very cheeky panty cut) and found myself not just imagining how they would look on her but jealous that she got to wear them everyday. I want to see what it’s like to have panties riding up like that but being so used to it that you don’t feel them- like how can you wear a thong or cheekster and not feel them while you’re having a conversation with me?
    So Assigment 1 has begun. I bought a pair of white hipsters (and a few others) and they’re waiting for me to wear tomorrow. Don’t think I’ll make it very far with this because I’m not really a sissy but I really need to see what it’s like to wear panties. Guess this hipster panty is where I’ll start. I think it would be really fun to have a conversation with my coworker where we both have panties riding up our asses without either one of us even feeling them.

  19. Mike Says:

    Hit a snag and won’t be able to start wearing the panties until Friday, but I will do it. Anyone want to join me? Kimmy in RI, any words of encouragement?

    • Anonymous Says:

      Yes. If you are curious, just do it.
      You only live once, and you only regret the experiences you miss out on due to fear.

      As far as practicality goes, things aren’t your friend. Not often anyway.

      For comfort you want something a little wider in the gusset. Some things are cut in a way that allow them to work. If you have one, keep it and treasure it.

      Hipsters are usually my favorite panties to wear. Try to find something Lacey with scalloped edges, they will cling better to your skin and reinforce the message of the assignment.

      The real message is to become familiar with feminine lingerie, on a personal level. Not for sexual gratification, not for a kinky game, but so that it becomes natural to you and feels normal.

      Once it does, you have achieved the purpose of the assignment.

      It doesn’t matter to me if you go all the way or not. I like honest comments and replies on this thread.

      But if you try one step, and find yourself 10 days later not noticing that you are wearing a delicate, silky panty… won’t want to go back to boxers or cotton briefs again.

      And you might look into other steps to see how comfy they can be too, and each step will at a minimum make you understand women better, if not embrace living in their wardrobes permanently.

      But do it, if you are curious, there is no reason not to try it.

    • Kimmy in RI Says:

      Entered reply but it never got posted.
      Trying again.

      What you need to do is buy pairs that feel comfortable at first. Think hipsters mainly. Most things are too thin to be comfy at work for rookies.

      Pay attention to the material, the silkier the better.

      After a week or two if you are faithful to doing this, they won’t feel odd/exciting or sexual…they’ll feel normal. They’d when your body is opening up to this, and that is when you start to feel like you are wearing nothing at all.

      Whether you go all the way it stop, you’ll gain a better appreciation for women and lingerie.

      You only live once, if curious….DO IT!

      What is the worst that will happen?
      You’ll find you like them better and never wear make underwear again.

  20. Mike Says:

    I wore the white hipsters on Friday and found that my ass is bigger than I thought when shopping. The hipsters didn’t cover much and spent more time up my ass than around. Not the most comfortable first day, especially since wedgies are hard to adjust through khakis, but I did get a rush talking to my co-worker, among some other women throughout the day. Yesterday and today I wore boyshorts and a bikini panty- much more comfortable with the bikini, stayed in place and were easier to forget about at times. Boyshorts- same deal as with the hipsters- they creep up fast, but I guess i kinda like the constant reminder for now. Gonna wear these three again the rest of the week and then go shopping for upgrades this weekends. Don’t wanna say I’m hooked, but…Any advice or suggestions?

    • Kimmyinri Says:

      If you’ve been doing this every day, then you are more than a week in, and have probably just started to get really used to them by now.

      They probably don’t feel alien on your body anymore. You probably rarely get excited merely by wearing them.

      This is your brain just STARTING a to accept this as the new normal. If you aren’t there yet, sleep in panties. When you wake up wearing them, it will also accelerate your brain’s acceptance that this IS the new normal for you.

  21. Anonymous Says:

    Thanks Kimmy! I haven’t been sleeping in panties, but I will start doing that now. And you’re right, the rush was sort of subsiding until Sunday when I went shopping again. I bought a lace bikini, string bikini, and a kind of biking/hipster with stitching in the back that makes it conform a bit. Taking it slow and not going for the cheeky panties or thongs yet- I wasn’t crazy about the ones that were riding up last week. But this is fun. I’ll keep you updated!

  22. Anonymous Says:

    Alright, I’m pretty comfortable with bikinis and boyshorts at this point I think it’s time to move on to skimpier panties. Any recommendations? How are cheekies and tangas? Are thongs or g-strings better? Thoughts?

    • B Says:

      Mike I hope you are still on your path. This is a great path and will test you for sure.
      Kimmy any encouragement on how to progress on this while having a fiancée?

      • KimmyinRI Says:

        If you have a fiancé, then you would best be served by being honest that this is a huge part of who you are. If the girl loves you m and REALLY loves you, it won’t matter.

        If it does, then her depth of feeling wasn’t worthy of a lifetime commitment.

        That’s my view.

    • Brandon Says:

      Mike and kimmi I’m ready to jump on board with you. Let me know where you are at and how fast I need to catch up.

  23. Kimmy in RI Says:

    You should be progressing.

    Why aren’t you in pantyhose yet?
    Are you shaving yet?

    Do you own a matching bra, and wear it at least 1 day a week?

    These are important steps that you need to take unless this is just a hobby/fetish.

    • Anonymous Says:

      I am new to this blog, but love it! I am masculine looking 38 year old male but crave to be a sissy. Can some one help and guide me!

    • j Says:

      I really enjoy this blog! I am a very masculine looking guy but I crave to explore my submissive side. I need guidance and direction in this please !

    • Anonymous Says:

      Mike don’t lose track and keep it up. I would do the assignments with you.
      Kimmy how can I get my fiancé to go along with this

      • Kimmy Says:

        Getting significant others to go along is hard. Basically it has to be an old fashioned kitchen table conversation, and you have to be honest and say it’s something you have to explore.

  24. Anonymous Says:

    I love…!!!oh how I LOVE!!!!

  25. sissyjilly Says:

    I just started these assignments I got a couple pair of panties both r hipsters one whit pink and black all tried with lace. And also have two pairs of pantyhose. Also am cleaned shave all over expect my face.

  26. jdmeyers5280 Says:

    I just wanna be a SLEAZY faggot cocksucker, dressing in skimpy shorts and getting fucked at Adult XXX Theaters and Arcades. I can NEVER get enough gloryhole sex, but i also like getting fucked Bareback in theaters while HORNY male’s stand around waiting for their turn, they like calling me a SICK and PERVERTED CUMDUMP! These days i try to get guys to use my camera on my cellphone to video me being a SLEAZY pussyboi. Sometimes i’ll go cruise homeless boys at the homeless shelters around Denver. My biggest vice is BIG BLACK COCKS, i’m 6’7″ tall and BIG and stocky. Men are ALWAYS SUPRISED that i’m an INSATIABLE CUM GUZZLING FAGGOT! But getting my holes by BLACK MEN who are shorter than me is what REALLY GETS ME OFF.

  27. Kimmyinri Says:

    I doubt most of what you wrote here, and if true that is just dangerous and unhealthy.

    This is much more than a fantasy to j/o to for most of us. And even for those that that is all it can be, they usually understand the desires and feelings and challenges the rest of us all have to face.

    By the way, these assignments WITH pictures was reposted on a born to darkness blog on WordPress. If I can find the link again, I’ll post it.

  28. Brandi Says:

    I agree with you on this last post. These assignments aren’t meant for that kind of response or degrading behavior.
    I am still looking to find someone who can help me push through some of the tougher assignments and join in on the journey

    • Kimmy Says:

      I’ve tried the online master bit before, and usually always got disappointed.

      But if you want to email me, maybe I can help a little. Lcolemanri@ AOL com

  29. Louise Says:

    Riana, I am a married Sissy a lot of these tasks I cannot do but dearly want to. I will start the program I will have to make some changes but will try to replace things I can’t do with things I can.
    I will update when I can.
    Xx Sissy Louise

  30. Louise Says:

    I am a married sissy I want so much to start the tasks, I have already done a lot of the things but need more. I will start the program but make some changes as I do not want to involve my wife. I will provide updates and photos if anybody wants proof I am doing this properly.
    Xx sissy louise

  31. Chris Says:

    I am on day one of assignment #1. I was sooooo nervous in the store buying panties. I bought 2 pairs. They certainly feel very different wearing them now. I hope I am not as nervous on the next assignment!!

  32. Chris Says:

    My first day wearing a thong. It feels weird!

  33. kennifer Says:

    Wow. First of all I’d like to say Rita sounds like an amazing woman. I love the way you handles your hubby. Wish there where more dominant, fun loving girls like you.
    I started off like everyone else I guess, just always turned on by girls and everything about them which grew into curiosity about girls clothes and makeup and everything else. I’ve done a lot of experimenting but also gave myself to a mistress who I asked to humiliate and expose me as much as she wanted. I gave my word that I would do anything she wanted and begged her to please keep exposing me without stopping even if I begged for mercy. Well she has kept her promise and has made every girl I know aware of my submissive ways and crossdressing fetishes. She has also made sure that ever girl I know has seen or now has my nude and sissy photos. Ive also been ordered to completely undress in front of dozens of girls and have even been sent home nude after my clothes have been given away. Very embarrassing
    I also wanted to share one of my earlier humiliations I caused myself. One night I was in the mood for some makeup and lipstick. After wearing it around the house I fell asleep like that. I was jolted awake very early the next morning when someone was at the door. I ran and answered it and was met by a female friend who I had a crush on…standing there laughing at me asking if I was wearing lipstick now. When she comes over she insists that I have makeup for her to use, in my bathroom (where anyone can see it) at all times as well as tampons, perfume, curling iron etc. Raises a lot of questions but then everyone knows now anyways. My biggest fantasy still is to wake up with big full breasts some morning, large enough that they can’t be hidden if I try. Large stiff nipples would be a start.

  34. Lynn in OK Says:

    I am sorry to see that this blog hasn’t been updated for over 5 months.

  35. Kami Klimax Says:

    Now that I have been completed with a sex change,I have to go find a man who is in to me and let him have his way with me

    Love KAMIGIRL.

  36. sub2girls Says:

    After reading this, it had made me realize that I am deeper into this then I ever planned to be. Some girls I know have been gradually feminizing me and really enjoy it. Recently, they gave me a bag that had 60 pairs of panties in it. They are all very nice and name brands only but all ones they have worn for quite a while which I find to be more exciting and so do they. I wear a different pair daily and keep them updated by sending pictures of me wearing them. The thing is, they have told a lot of their friends so I really can’t deny that I wear them but also I hate wearing my make underwear any more. In the next few days, I am supposed to gather up every pair of my underwear and give them to them. I’m actually going to do it and will make sure I give them EVERY pair. The next step they want is already under way, taking estrogen to end erections forever, grow breasts and start actually being a girl so everyone finds out. I’m giving them plenty of blackmail information and pics which they promise to make public no matter what I say. Guess I’m pretty much committed to this a lot more then I realized, like I said.

  37. justmeonlymorefeminine Says:

    One of the biggest steps I’ve taken to committing to this was to learn to shop in busy stores, often and to make sure someone tells you what to buy and where. It shows the world you’re a sissy and you can’t deny it any longer. The other thing that was a huge commitment and should be mandatory is tanning in a bra or bikini until you have definite tan lines. Every morning when you look in the mirror you are reminded what you are like. It also ends any chance of having sex without revealing your secret and therefore stops any flirting etc. to make you more committed to being an obedient sissy. The thing is, those tan lines are there for months too so it’s drilled into memory that you are a sissy. You can write things on your body or put feminine stickers or tattoos on to tan in too just as a reminder. A nice playboy bunny or tramp stamp possibly? Also makes you wonder if anyone actually saw you tanning if it’s outdoors.

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