Sissy Task

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Sissy Task
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Home 25 Assignments to make you the perfect sissy

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Do you fantasize 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. Below, you will be given a series of assignments and sissy tasks that will take you on a journey through humiliating sissyness and on towards your total feminization.
Follow the assignments and tasks here. 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. So, are you ready?
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 feminized. 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 workday, 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.
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 satin 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-opaque, 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.
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? Every time 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 dedicated 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, makeup 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.
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.
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 online 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 feminized, 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. Savor 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.
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 color 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 color. Face your cocksucking mirror. Run the firm, waxy stick across your top lip. Press your lips together and see the color transfer to your bottom lip. Drag the lipstick across your bottom lip, backward and forwards until the color 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 color last longer. Now begin your cocksucking ritual. Kiss the tip and look at the feminine, red lip marks 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.
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 they 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.
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.
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 deniers 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 color, 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.
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 makeup 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 color 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 panty lined panties, you cocksucking, panty-wearing, feminized, 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 color. 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…
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