Sissy assignments

[theboygirl]

These are assignments that I found and thought it would be good to share and for people to add pics/videos/experienes
MOD EDIT: Original can be found here:http://thunderbolt972000.xanga.com/701614156/item/ In the future, if something isn't yours you HAVE to give credit. I will not be so nice next time.
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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 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.

[theboygirl]

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.

[theboygirl]

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.

[theboygirl]

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. 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.

[theboygirl]

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.

[theboygirl]

Time to continue your attitude adjustments, sissy girl.

It may be hard to believe, but even now, when you masturbate, you wank too much like a Real Man. Even though you have a little boyclit instead of a real cock, and you may only cum once for every ten times that you practice cocksucking (and, when you do, you must eat your cum), you do have direct control of the action - you can take matters in to your own hands, quite literally.
That's about to change.

It's time to shop for another dildo, and I think that you can guess what this one will be for! Why can't you just use the one that you have been sucking on? There are many reasons: a shape that is good for sucking may not be optimal for, well, other things; there's the hygene factor (although we may address that concern in a later assignment); but, most importantly, there may be times that you will be filled at both ends! This dildo need not be realistically detailed, nor should it be as large. (Was that a sigh of relief, sissy? Or something else?) But it should have a head that's bigger than the shaft, and it should be curved, like a rampant erection, the better to find your sissy G-spot.Put the two dildos together and examine them side by side. Measure their girth by wrapping your hands around each of them in turn. Take the new one into your mouth to get a sense for how it compares to the first; as you suck on it, imagine how large it will feel in your boypussy. Start on your back, with you legs spread and your knees drawn up slightly - whatever feels comfortably relaxed. Slide a pillow under your ass to make it more accessable. Accessability - that's an important and recurring point, sissy. Put a large dollup of lube on your finger and spread it on and around your sphincter. Does that intimate contact make you a feel little apprehensive, sissy? It should.

Spread another dollup inside. Does that feel good? How did your boyclit react, hmmm? Put some lube on the head of your new friend and spread it around. Then some more - it's important to use lots of lube. Now for the moment of truth. Holding your dildo with one hand, use the other to spread your ass cheeks and guide that missile to its little puckered bulls-eye.
Your sphincter will probably resist this bulbous invader at first. Be patient, but persistent. Rub the head around your anal ring, first pushing it in a little, and then retreating. Try to relax your sphincter muscle in response to these advances. Finally, you will have pushed the head in far enough to get past the ring, and your greedly little sphincter will close tightly behind the head, thereby pulling the dildo in deeper. Did that make you gasp? That's it - your last defenses have been breached. You've been deflowered; you might as well relax and enjoy it - your boyclit appears to have! Pause a moment and get used to the feeling of that cock inside you. Move it a little, in, out, and around, experimenting. Aim that monster at your belly button and try to find your sissy G spot. Now pull it all of the way out - your sphincter is reluctant to let it go, isn't it? Relube and slide it back in. It goes in much more easily this time. You're getting used to this, you little slut!

Start to fuck yourself slowly, with long strokes in and out. All of the way in, and then almost all of the way out. Let your body move in response: thrust your hips upward to meet the instroke, and roll them back on the oustroke. When you used to wank your boyclit, it was just your hand doing the work; now your whole body should be in on the action. With your free hand, play with yourself. Stroke your skin, fondle your nipples, rake your belly with your fingernails. You may touch your boyclit, but only enough to keep it perky! Try varying the tempo, or how far in or out it goes, or where the head is aimed, and note your body's reactions.

While continuing to fuck yourself, reflect on this. There are several purposes to this exercise; the first one being to move your focus for sexual gratification from your boyclit to your boypussy. To that end, you will never again touch your boyclit to bring yourself to orgasm. You will only cum from being fucked in the ass. Oh, it's possible all right, although it may take a while for your body to learn how to do it. It will be a frustrating time, I'm sure. But, you say, real women touch themselves when they masturbate. Yes, but the feminine ideal is to be fulfilled - to achieve orgasm - through penetration alone, and your goal is to be ideally feminine, isn't it, sissy girl? The second purpose is to externalize the source of your sexual gratification. You are no longer self-contained; you will be dependent on penetration from a cock in order to achieve orgasm. You will probably start to find phallic shapes very intriguing! How humiliating! A Real Man would not swoon over the shape of, say, a banana, wondering how that would feel inside him. But you aren't a Real Man, are you, sissy girl? The third purpose is to open you up (literally), to make you feel more vulnerable, more... accessable. Real men are too controlled, too tight, too rigid. As a sissy, you must become more reactive, more pliant, more... submissive. Accepting that alien invader now burrowing deeply within you is a step in that direction. Can you imagine a Real Man fucking himself in the ass with a rubber cock? Of course not. Your boyclit is probably leaking precum all over the place by now. You must not waste any. Scoop it up off your belly with your fingers and then lick them clean. But don't touch your boyclit! Instead, tighten and release your anal muscles around that dildo, and feel how it makes your boyclit perk up! So, only touch your boyclit when you need to; otherwise, milk that dildo. It's probably time to try a new position. Keeping the dildo inside you (unless you really were looking forward to the feeling of reinsertion!) roll over and get up on your knees. We want both hands available, so you might need to put a big pillow under your breasts to be comfortable without having to hold yourself up. I bet that your ass looks really cute, waving around in the air like that. Does this position make you feel more accessible, more vulnerable? Imagine that Real Man has surprised you and wants to have his way with you. Given your... position... all he has to do is to grab your hips and plunge his charger deep inside you. But don't worry, there aren't any Real Men around here. smirk

Next time have a plate handy to catch all of that precum that is leaking down onto the sheets. You'll know what to do with it. After fucking yourself doggie-style for five minutes, try another position. It's called "Sissy Cowgirl". (This is a good time to relube that cock, if you haven't done it recently.) Take that pillow and fold it or bunch it to provide a firmer support, and drape a towel over it. Set your dildo on it and hold it upright, pointing to the sky. Your job is to impale yourself on it. This time, instead of guiding the cock to you, you're going to guide yourself to it. Kneel with the pillow between your legs, and with that cock a little behind you. Without looking, but with your free hand spreading your ass cheeks in anticipation, lower yourself toward that cock. Your free hand will have to help guide you to the right spot. It may seem awkward, but don't worry, practice will make it perfect! When you've reached the target, lower yourself onto it. There! I'll bet that made your boyclit jump! Since the pillow keeps the dildo in position for you, largely but not entirely immoble, your body movements are key to maximizing the sensations that you feel. Try rocking your hips slowly back and forth. Rotating them, first one way and then the other. Let your body tell you what feels good.

Your hands are free to do things like cup your breasts. Grab your buttocks. Support your weight as you experiment with different angles. Scoop up that never-ending supply of precum. Next time, set up your cock-sucking mirror so that you can watch yourself squirm as you ride that cock. Or had you thought of that already? If you can reach orgasm without touching your boyclit, congratulations! You've scored! (Of course, you remembered to catch your cum. You're so well trained!) But if you can't quite get there, don't worry - there's always tomorrow. Because I want you to fuck yourself daily. Do it first thing - that way, you can wonder which of the women you'll see that day also got fucked that morning. Keep up your cocksucking as well. What's that? Can you combine sucking and fucking, do them both at the same time? Sissy, you're such a slut sometimes! Well, if it adds an extra note of excitement to feel one cock up your ass while you're sucking another, or to have your mouth filled with cock while you're fucking yourself into ecstasy, then more power to you. But you should still spend time concentrating on each activity individually. You'll just have to wake up that much earlier!

Your assignment is to fuck yourself every day for a week. Three positions, at least five minutes in each. Can you dream up new ones? How about: sprawled back in a big easy chair or sofa, with one or more legs draped over the arms or back? Don't forget to put down a towel! Or, can you think of ways that you can brace your dildo against something while on your back or in doggie-position, so that you won't need to use your hands? If you are able to cum just from penetration, feel free to do so as often as you are able. (Enjoy it while you can. smile) If you can't, don't worry. Maybe your dildo just isn't big enough - although you did buy one that was as least as big as your boyclit, didn't you? (Think about that for a moment.) You'll have a chance to rectify that possibility in the next lesson. grin