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INTRODUCTION
I used to think that the desire to wear women's clothing, particularly underwear, was a sign of being a sissy. In particular, that the desire to put on women's knickers meant that you must be a sissy.
But now I see things differently. There are a whole range of people who wear women's clothes either sometimes or most of the time.
Women, of course, can wear more or less what they like and society (or at least Western society) finds this acceptable. It is the case that different occasions may require more or less flesh to be exposed, and women are expected to keep their private parts decently covered. But it is usually accepted that women may wear men's clothes. And when they do they are not usually pretending to be men. They are just asserting their right to wear what they like to in a feminine way.
Some men wear women's clothes because they feel that they are feminine but were "born in the wrong sex". Some men cross-dress because they want to feel more feminine, or to make a statement that clothing does not define gender. For some men, occasional crossdressing permits an escape from the burden of masculinity - like a holiday from what is normally expected of them. Some just wear women's clothes for sexual arousal (and there's nothing wrong with that). And of course there are drag queens and pantomime dames. These are basically entertainers, presenting as exaggerated caricatures of women.
But (in my view) a sissy is something different. And I should emphasise that what I am writing here is my own opinion. My own definition of what being a sissy is all about.
So if you think you are (or may be) a sissy, read on.
WHAT IS A SISSY?
A sissy is a biological male. He does not want to feel masculine, but knows that he cannot ever be really feminine. He is less than a man, and less than a woman.
Some are full-time sissies. For many others - secret sissies - it is a very private and part-time escape from the hard realities of life.
This guidance is mainly provided for secret sissies. Sissies who want to develop their sissiness in the privacy of their own homes.
Some of you may be already some way along the road, but this guidance starts at the beginning of the journey.
If you are very lucky you will have a female partner who can help you. Perhaps a wife or girlfriend, perhaps an aunt whose adult children have all left home (especially if she only had sons and wanted a daughter).
A helpful partner can advise on garment sizes and with obtaining items of womenswear. She will know which shops will stock what you need, and may be aware of smaller specialist shops you didn't know about.
And perhaps she will encourage you to develop your sissiness further and faster than you would on your own.
And in return she may expect something back from you. Housework, for example. Who wouldn't like to have a maid that didn't need to be paid to do the dusting and ironing while she sat back and watched? Or maybe she might need more intimate services?
But at this stage I do not recommend signing up with a professional mistress who will expect to be paid for her services. Right now you need to save your money, so that you can spent it on buying women's clothes.
WEAR A BRA
As I said at the beginning, I used to think that wearing women's knickers was a sign of being a sissy. And it can indeed be so. In fact a sissy SHOULD and WILL wear women's knickers.
But the real PROOF that you are a sissy is when you wear a bra.
A woman wears a bra to support and protect her breasts.
A man who does not have breasts does not wear a bra.
A sissy wears a bra.
A sissy who has no significant breast tissue wears a bra because it is a symbol that he is not a man (and not a woman).
Ideally a sissy's first bra should be the correct size to fit his body closely, preferably lightly padded. However, in the UK there is a limited availability of bras with a man's chest size but with AAA or AA cups. (Bras with these cup sizes are usually intended for a teenage girl whose breasts are only beginning to develop). An alternative is to look for a mastectomy bra with pockets. The pockets allow for the insertion of foam or silicone falsies to give the shape of a bust. The cups on these bras are usually elasticated so that they fit close to the chest when worn without inserts. These bras are readily available from the usual online retailer.
A sissy does not need to use fake breasts at this stage. He needs a bra to wear under his male clothes. He needs the gentle grip of bra staps to remind him that he is wearing a bra. By wearing a bra he is admitting to himself that he is a sissy.
He is also taking the risk that someone may notice that he is wearing a bra. There may be tell-tale little bumps showing under his outer clothes. Or someone may touch his back and feel the bra strap. Anyone who notices that he is wearing a bra but has no breasts will know that he is a sissy.
Women are more likely than men to notice secret bra-wearing. Usually they will not say anything.
But they will know!
If you are not ready yet to let people know that you are a sissy, don't wear a bra in public or at work.
But if you are a real sissy, the time will come when you want people to know.
Or at least want to take the risk of being noticed.
SISSY KNICKERS
As I said earlier, a sissy will also wear women's knickers. The two items go together, don't they? Bra and knickers.
But for a sissy, the choice of style of knickers is important. Forget about trying to find a matching set of bra and knickers. The most important, or I should say ESSENTIAL attribute of the sissy's knickers is that his cock and balls must be completely enclosed at all times. If he gets an erection, the knickers must be accommodating enough to ensure that none of his bits stick out anywhere.
He must understand that women's knickers are more powerful than his sissy cock.
A sissy's knickers should had elasticated leg-holes - these will ensure his balls are contained within his knickers. Many different colours are available, but the majority of a sissy's knickers should be at the pink end of the spectrum, with some white ones. Silky knickers feel much nicer that cotton ones.
I should perhaps remind you that a sissy must obtain his underwear by legitimate means. He must not steal or "borrow" underwear without the owners consent. So buy your own! Unless you are able to request an accommodating aunt or other female relative or friend to give you a pair. Although this may seem a daunting prospect, the lady concerned may help you in finding the correct size of undergarment required.
It is important to know the correct size because you are going to need many pairs. Sizes from different suppliers may vary. If you find some that fit well, get more from the same supplier.
You will need AT LEAST as many pairs of knickers as you have male underpants. Sissies may find that it is necessary to put on a clean pair more than once a day!
And when you have acquired the required number of pairs of knickers you must dispose of ALL your male underpants. You will not be needing them ever again. You will wear women's knickers every day from now on. (If your boy pants are properly laundered, you can donate them to the Salvation Army. Men's underwear is always needed for the use of homeless men.)
And if you will be wearing a bra every day, you will need more than one. All underwear needs to be washed sometimes!
Although you can put a bra in the washing machine with other clothes, your knickers should be washed by hand. Let them dry naturally, either hanging up or laid out on a towel. Never put them in a tumble dryer. They are delicate garments and need to be treated with care. And with RESPECT! They may need to be ironed. Store them in your underwear drawer in one or more neat piles.
SHOPPING
Although these days you can buy all sorts of things online, sometimes it is better to go to physical shops.
Consider having a day out to a different town, perhaps some distance from where you live. In a place where nobody knows you, it doesn't matter if shop assistants are aware you are buying women's clothes, underwear or shoes for yourself.
Shop assistants often get a bonus or percentage based on sales. They are more likely to help you than criticise or turn you away. Business is business! (Although they may not let you use a changing room if the shop is busy with women customers.)
And if you can get help from a shop assistant you are more likely to spend your money on items that fit properly.
If you find a store where the shop assistants are helpful and not critical, make a note of it. You can go back to shop there on another occasion.
If you're shopping in your home town, you can always pretend that you're going to a fancy dress party when buying a dress or shoes.
But this is not such a believable excuse when buying underwear, especially knickers.
WANK LIKE A SISSY
I mentioned erections earlier. Even a sissy can get an erection. It doesn't depend on the size of his cock. The ability to do so is part of the male anatomy. Both men and sissies can use an erection to masturbate like a man. But a sissy is not a man. There is another way.
To wank like a sissy, you must start with a limp cock. Wear your bra but no knickers. (If you have a suspender-belt and stockings and maybe some heeled shoes, you should wear these too to enhance the experience.) The other thing you need is a full-length mirror. And it may be advisable to have a towel to stand on (to avoid getting cum-stains on the carpet).
Stand in front of the mirror. Put the 3rd and 4th fingers of your wanking hand in your mouth to lubricate them with saliva. Now use these two fingers to push the end of your limp cock completely inside your body.
Now start flicking the end of your cock with your middle finger.
Looking at your reflection you will see that you are a sissy. You are wearing a bra. Your fingers are inserted into your body where a woman would have a cunt and a man would have a cock. Your reflection may have balls but you doesn't have a cock. You are fingering your sissy clitty.
You will soon find that it is not necessary to have an erection in order to climax. Now you know how to wank like a sissy.
REMOVE BODY HAIR
A sissy should let his head hair grow enough to allow it to be styled in a girly (or at least unisex) way. It doesn't necessarily have to be shoulder-length. His eyebrows should be kept trimmed neatly. All other body hair should be removed.
You will find that knickers, especially silky ones, feel much nicer on your hairless balls and hairless bottom.
Shaving is a good way to remove pubic hair, but it needs to be performed frequently. Avoid prickly panties!
Shaving is less desirable for legs, especially if you will be wearing stockings. Shaved legs may have the feel of sandpaper after a day or so. Alternatives are depilatory cream, waxing or epilation. Waxing and epilation have the advantage that they remove hair from the roots. It takes a few days for new growth to emerge from the skin, and this growth will be fine hair. A small proportion of hair pulled from roots will not grow back. As you get older, this proportion will increase, so over a period of years there will be a significant reduction in hairiness. Shaving, on the other hand, only cuts off hairs at the surface of the skin, so stubble will emerge fairly quickly and no hair roots are affected.
An epilator is a small hand-held device of a similar shape and size to an electric razor. The business end comprises a set of rotating discs that will grip hairs and pull them out. This works well on firm skin (like the front of your lower leg, but you need to stretch more fleshy parts (like the rear of your thighs) to make the skin firm enough so that the rotating blades do not grab flesh instead of hairs. Follow the instructions that come with the epilator!
Using an epilator on legs are quite hairy, will be painful because many hairs will be pulled out at the same time. It is best to remove hair by shaving before using the epilator for the first time. As soon as your legs are dry, use the epilator and then continue to use the epilator every morning and night for about a couple of weeks. Then you can reduce to once a day and perhaps less frequently, depending on how vigorous your hair regrowth is. But if you let your legs get hairy again, you will have to repeat the above procedure.
Regular use of an epilator is less painful and less messy than waxing. The epilator will catch thin wispy regrowing hair that is difficult to see. This thin regrowth is less painful to remove than established thick hairs. And the hairs that regrow more rapidly will be removed more frequently. This regrowth will be weakened after a time.
DO NOT use an epilator on your pubic hair. This could result in pain, blood and scar tissue. Not to mention blood-stained underwear.
If you want to maintain smooth, hairless legs, REGULAR use of an epilator is the recommended method. After the first few weeks, there will only be a few hairs removed each day. There will be a little plucking sensation with each hair removed. Think of each of these as a little more of your masculinity being extracted.
Depilatory cream can be used on arms, legs chest and genitals. Put the cream on your legs first and coat the more tender parts last, so that the contact time is less for delicate areas. Let the cream work for at least the time recommended on the packet. If it starts to burn, wash it off immediately. Wash under a shower, gently rubbing your skin with your finger-tips to encourage hair to detach. Ensure you wash off all the cream. Pat yourself dry with a towel, rather than rubbing vigorously.
Depilatory cream can have a strange smell. It will leave the skin (especially on your legs) as smooth as glass. A much smoother finish than with shaving, but it does nothing beneath the surface of the skin, so regrowth will occur, as with shaving.
A sissy with white skin should avoid sunbathing. The legs, especially the upper thighs. should remain as soft and pale as possible.
STOCKINGS AND SUSPENDERS
ONLY once your legs are smooth and hairless, can you consider wearing stockings. NOT BEFORE!
Of course, these days women generally wear tights (pantyhose). But you are not a woman. You are a sissy. So you should wear stockings with a suspender-belt to hold them up.
Stockings and suspenders may be thought of as rather old-fashioned. But the same could be said about the style of knickers you are probably wearing.
And rather like wearing a bra, it is is the sensation of wearing stockings and suspenders that is important. The grip of the suspender-belt around your waist. And the way that taut suspenders tug at stocking-tops as your legs move.
And that area of bare flesh between stocking-top and knicker leg, emphasising the different elements of your underwear. Not the smooth continuity of tights.
And later in your journey, when you start wearing a dress or a skirt, the thrill of wearing stockings and suspenders will be even more apparent. The risk of people seeing that you're not wearing conventional tights. That you have a more interesting upskirt area...
Being a sissy is not about wearing clothes that are convenient and practical.
Unless you have a particularly slender waist and a larger hip measurement you will struggle to find a suspender-belt (garter-belt) of the type displayed on mannequins in department stores, that is both comfortable to wear and that will stay in position once your suspenders are fastened to your stockings.
The usual online supplier offers "bra extenders". these are small strips of bra strap material with hook and eye fastenings that can be fitted to the ends of the back straps of a bra to extend the band size by 2 or 3 inches. They can also be used on suspender-belts, and will significantly increase the range of suspender-belts that will fit your waist size.
But if the shape of your waist/hip area is more male than female, the problem of the belt slipping down your body remains.
You will probably need a deeper belt, several inches from top to bottom, in order to ensure it stays in the correct position. Ideally you should obtain a lace-up belt, but these are relatively expensive. (But it is a delicious sensation to be laced in. And when you tie the laces in a bow behind your back. And when the tied laces dangle down and tickle your bare bottom...)
I constructed a DIY one piece garment by adding strips of material between one of my bras and one of my suspender-belts. it was simple to slip my arms into the bra shoulder straps, then fasten the bra behind my back, then fasten the suspender-belt behind my back. The suspender-belt was held in the correct position at my waist by my bra straps and the belt did not need to be excessively tight. A simple solution requiring only basic hand sewing skill.
(And, by the way, you will find it easier to carry out sewing tasks if you are dressed in skirt, knickers and stockings. You will feel more relaxed and have more patience.)
It is important that your suspender belt remains at the right height around your waist because you need to ensure that your suspenders are nicely taut, so that you do not suffer from wrinkled stockings.
The suspender clasps need to be metal (plastic ones unfasten themselves too easily). Three suspenders per leg will be sufficient. The suspenders should not be too short (4-6 inches at the front would be good), but the actual length will depend on the length of your stockings.
The correct way to put on stockings is as follows:
- with clean hands and smooth nails, take one stocking and place both thumbs inside the stocking top. The heel of the stocking needs to be on the underside.
- using your fingers gather the stocking over your thumbs until you reach the toe of the stocking. Ensure that you do not twist the stocking while you are gathering it.
- put your foot into the toe of the stocking, the slowly and carefully spread the stocking up your leg and then attach the stocking top to your suspender clasps
- repeat for the other stocking/leg
- adjust the length of the suspenders as necessary. The ones at the front on each side need to be taut when fastened to your stockings, the ones at the back/side needs to be a little less taut - just slack enough to enable sitting down.
Ideally, your foundation garments (bra and suspender-belt) should be white, but being realistic, size and functionality are the prime considerations.
If you are a white skinned sissy, your stockings should be dark tan. Traditional and functional. Your dark stocking-tops will contrast with your hairless pale sissy thighs. If your skin is darker, you might consider a different shade. A light tan, perhaps, so that your stocking-tops contrast with your skin colour. It needs to be obvious that you are wearing stockings. That you are wearing items that a man would not wear.
Do not buy very stretchy stockings - they are not so comfortable and don't look very nice. On the other hand, fully fashioned stockings are not for sissies either. These have to be bought to suit the foot size and are too elegant/expensive for sissies. If you buy stockings with seams, you must take care that your seams are straight as you put them on. A sissy does not need seamed stockings. A sissy is not trying to appear elegant.
Once you have found stockings that look OK and feel comfortable, buy several pairs of the same style, shade and brand so that you can mix and match if necessary. (If your pairs of stockings are all different, when one stocking gets damaged, its undamaged partner is useless too.)
Now you have a full set of underwear that can be worn under male outer clothes. Bra, knickers, suspenders, stockings.
If you wear them under your male clothes in public, remember that it's not just your bra that may be detected. The bumps of suspender clasps may show when seated. The wide gusset seam at the back of your knickers may be discernible if the seat of your trousers is stretched when you are bending forward. And your nylon-clad ankles will show when you are seated.
Your stockings, like your knickers should be hand-washed. When a washed pair is dry, fold the stockings carefully and store each pair separately in a plastic bag (the original pack may be suitable for storage).
SHOES
You are probably already thinking about wearing skirts and dresses.
But before that, you need some suitable shoes. Although in the UK, women's shoe sizes are theoretically the same as men's sizes, you will usually need a wide fitting as women's shoes are normally narrower than men's. You may need half a size larger for shoes with 3 inch heels. For US shoe sizes, you will need a women's shoe that is one and a half sizes larger than your men's size, and for EU sizes you will need a half size larger.
Once you have worked out the shoe size you need, I suggest you look around charity shops and the cheap shoe outlets. Unless, of course you have the courage to go into a high street shop and ask an assistant for a women's shoe to fit you. Remember my advice about shopping in another town. If you intend to try shoes on, you should be wearing nylon stockings or pop socks, not men's socks, which are thicker than nylons. Don't buy expensive shoes online until you are confident about the size you need.
Your first pair of women's shoes should have heels of two to two and a half inches high. Black shoes will make your feet look smaller and will be OK to wear with most dresses, so are preferred if you can get them. But in a charity shop, if heeled shoes fit buy them, whatever colour they are.
You will find that wearing these heels will change the shape of your legs and make your bottom stick out more. Providing that the shoes are the correct size for you, they will be comfortable to wear all day. You will need to take more dainty steps. A sissy wearing heels cannot walk like a man.
Get used to walking in these heels before considering shoes with higher heels.
Only buy stiletto heels if you are of fairly light build. Stiletto heels can damage floors, especially wooden parquet or vinyl flooring. This is especially important if you are living in rented accommodation with vulnerable flooring.
DRESSES
It is better to buy a few dresses before you consider purchasing separate skirts and tops. A fairly loose fitting dress will help to conceal the fact that your waist is not much slimmer than your hips.
But that is not the main reason for a sissy wearing a dress that is not fitted at the waist.
When you are wearing a loose-fitting dress, the dress does not assert its presence in the waist area. But it accentuates all the sensations you get from your undergarments and at the same time reminds you of the absence of trousers.
Wearing a dress gives you a sense of freedom. But also a sense of vulnerability - male outer clothes do not offer the possibility of your underwear being visible.
There are plenty of size charts online. Measure your chest, waist and hips. Decide what dress size this approximates to. Now assume that your chest size is 3-4 inches larger (as it would be if you had tits). Decide what dress size this would be as well.
At the moment you don't have tits. Your first dress doesn't need to allow for them. But if you are going to be looking round charity shops, you may as well look for anything that will fit. Tits or no tits.
There are a couple of other things to bear in mind. The male anatomy typically has broader shoulders than the female body. The shoulder measurement is not included in dress sizes. You need to judge this for yourself when you look at a dress on a hanger. Also look at the sleeves. Will your arms fit in them?
But especially for your first dress, it is better for it to be your true dress size or a little larger. And certainly not smaller.
So get and trawl those charity shops. Remember, buy your true dress size or larger. The colour and style of a dress don't matter as long as you are going to be able to wear it. You won't be going out in public wearing these first dresses. You will be getting used to the feel of wearing a dress around the house and becoming more confident about what size of dress you need. And imagining what style of dress suits your level of sissiness.
Later, when you go looking for new dresses, dresses for sissies should generally be:
- loose fitting
- simple
- short (or maybe even VERY short)
And remember to allow for whatever bust size you might me aiming for.
HAIR AND MAKE-UP
When you are shaving your face, completely remove your side-burns. Shave up to the level of your ears.
Go to a ladies salon to get your hair washed and styled. Tell them that you want to look less masculine. Take their advice about how long to let your hair grow.
Go to a nail-bar to get nails neatly trimmed and coated with clear (or just slightly pink) varnish.
If you are going to learn about applying make-up without the assistance of a real woman in your life, you will have to rely on advice and tutorials online.
In this case keep it very simple.
Trim your eyebrows as short as you dare and apply eyebrow pencil to shape them. Pluck any eyebrows that are wayward or not the same colour as the others.
Practise applying lipstick. It will take time to get it right. Remember that you will need plenty of tissues and/or wet wipes, especially at first.
Always use tarty red lipstick when sissily dressed.
Always remember to remove your make up before going to bed at night.
TITS
We all wish we had tits, don't we, sissies?
If you have even a small amount of breast tissue, you can get very cheap bust enhancers from the usual online outlet. These "chicken breast fillets" look just like that. Wear them at the bottom of your bra cups. If you've got a little something to start with, they are surprisingly effective at creating a bit of a cleavage with your real flesh. But they won't make mountains out of mole-hills.
So if (or should I say, when) you yearn for more bust the next stage is to get some falsies. Foam bra inserts are the cheap option. It would probably have been cheaper to buy them at the same time you bought your pocket bra. Perhaps you did? If you didn't, check what is the largest size inserts can be used in the pockets. If you want larger tits, you'll need a new bra.
Foam falsies will give you a shape, but not the weight and bounciness of silicone falsies. If you can afford silicone, don't hesitate. You'll be surprised how heavy they are, and how this changes your balance and stance. You'll understand why women with even moderate size tits wear bras to spread the load onto the shoulder straps. And to limit how much they can swing about, too.
It's very pleasant how bouncy silicone falsies are when you're just walking round the house. The next best thing to real tits. You can use adhesive to attach them to your chest if you want to, but you'll still need to wear a bra.
You can also buy "breastplates". These are like plastic vests with built in silicone boobies. I don't think you would want to keep them on very long, especially in hot weather. I think they are mainly for stage performers.
I am not going to recommend cosmetic surgery. This is not for sissies. Nor will I advise taking hormones or other fancy supplements.
Noogleberry breast pumps are designed to suck breast tissue into plastic cups using vacuum. This is supposed to encourage blood flow in this area and cause a gradual increase in breast size. Although there are videos of men being able to get the plastic cups practically full of "breasts", the swelling diminishes to almost nothing when the vacuum is released. I don't believe a man or a sissy can ever achieve a significant permanent increase in bust size with this method. I think the the chicken breast fillets are probably just as effective. And much cheaper.
CHASTITY DEVICE
My view is that a sissy does not need to wear a chastity device in the privacy of his home.
If your sissiness is being developed under the guidance of a real woman, she may have a different opinion. And she is the boss. Do as she says.
If you are going out in public and wish to avoid the risk of an embarrassing skirt-lifting erection, a chastity device is the obvious solution.
Tucking is not really a satisfactory alternative. It's quite tricky to do, especially in the limited space of a toilet cubicle after you've needed to pee.
A variety of devices are available on line. I prefer pink plastic. It is important that the device is the correct size and is properly fitted. It needs to be secure and you need to avoid the risk of painful injury.
Usually the device has two plastic parts that are locked together, trapping your ball sacs between the two parts, but allowing your balls to be outside the device. There is a back ring that fits against your body behind your balls, and a front tube that encases your cock.
It is best to purchase a device that is supplied with different sizes of back ring, so that you can select the best fit for your body parts.
The front tube needs to be just large enough to contain your cock when it is completely limp. In order to check your size, you first need to wank until you feel that your balls are drained. Let your cock shrivel, and then measure the length and the diameter at the largest point (the bulb of the cock head). The dimensions will probably be smaller than you expected.
When you order the device, its best to purchase a modest amount of lube with it. The supplier may also recommend cleaning fluid or other extras. You can decide whether you need these as well, depending on the price.
When the device arrives, and before you try to fit it onto your private parts, read the instructions. Try putting the parts together so that you understand how it works, particularly the locking mechanism. And make sure that you can unlock it!
Choose the correct back ring. It needs to be a snug fit, but not a tight fit that could restrict the flow of any bodily fluid (blood, piss, cum). it should feel comfortable. If the ring is not sufficiently snug, it is possible that it could slide out of position. This could allow your cock to escape the tube and stretch your ball sac, bruising your balls in the process.
Apply a small amount of lube to the inside of the back ring. Ensure that you are holding the ring the right way round (locking part to the front). Put one of your balls through the ring, and then the other one. Now push your cock into your body (as if your are performing a sissy wank) and let it re-emerge through the ring. Rotate the ring so that the locking part is in the correct position (at the top).
Note: if you can put your cock through the ring first, and then put your balls through afterwards, the ring is too large.
Before proceeding further, it may be necessary to ensure that your cock has the same dimension as when you measured it. I'm sure you know what I mean.
Apply a very small amount of lube to the inside of the cock tube. A small amount, evenly spread.
Slide your tiny cock into the tiny tube. Line the tube up so that the locking part can connect with the ring. Make sure there is no flesh trapped as you fit the tube and ring together. If all is OK, fit the lock.
DO NOT lose the key!
If your cock attempts an erection while the device is fitted, it will be painful. The attempt will be abandoned.
When you have a pee (sitting down as sissies do), use a folded sheet of toilet tissue to clean and dry the device as well as you can.
Although some sissies report that they remain cock-locked for considerable periods of time, I would recommend only short periods to start with, maybe a couple of hours. You can then extend the lockdown period as you wish. But I think the tube part of the device will need to be removed for cleaning on a regular basis.
I don't recommend wearing a padlock while showering or bathing. The lock may not work properly if its internal parts get rusty, or if any lubricant is washed away.
OUT AND ABOUT
Don't be seen out in full sissy mode, flashing your underwear. If you go out in public, you will need to present as a woman. Society is not yet ready for an army of sissies on the streets.
When, and only when, you are ready to be seen in public, have a friend, colleague or relative with you.
You will need a handbag to carry your phone, keys, credit card, lipstick, handkerchief, etc etc. Practice carrying it. Make sure you know where it is at all times. As you are not used to carrying and controlling your handbag, choose one with a shoulder strap that you can use with the strap on your left shoulder and the bag on the right side. Or vice versa.
It's best to only attend a more or less private function to start with. A family fancy dress party, or at Halloween in the office, for example.
And make sure that your outfit is suitable for the event. There may be children at a family event. It will be wiser go to the Halloween looking like an assistant from the HR Department, and not to turn up dressed as a French maid or a sixth-form schoolgirl from St Trinian's. Don't go over the top with your outfit for the first Halloween. You need work colleagues that are supportive and accepting, not shocked or scared of what you might do next. Maybe you can push the boat out a bit further next year.
When you are able to go out on your own with an air of confidence, just go for short journeys in daylight. Perhaps a trip to the supermarket, but not when it's very busy, otherwise you may be standing in a queue at the till for a long time.
Remember to present as a woman, not as a sissy.
Take off heeled shoes before driving a car. Make sure your discarded shoes are not in the driver's footwell, where they could get stuck under the brake pedal, for example.
Stay safe!
CONCLUSION
You can have a great deal of pleasure being a secret sissy alone at home. Even better if you can be a sissy under the guidance and gentle control of a female associate.
But, generally speaking, you cannot be a sissy in public. Especially in some jurisdictions.
In some places it can even be tricky if you are identified as a "cock in a frock" while in public.
Sorry, but for the foreseeable future you can only be your real sissy self indoors, alone or with special friends.
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