18 You are to go to a pharmacy or department store and buy yourself a bottle of nail polish. Don't buy a quick drying polish - they don't stay on long enough for your needs.
Chose the brightest red you can find. NOT the first one you find. By all means pick this one up but compare it with all the others on sale to make sure it is the very brightest red nail polish in the whole shop before you buy it. When you are happy that you have the very brightest available, buy a set of toe-spreaders and a nail file or emery board as well.
Do not buy nail polish remover. If you already have some, throw it away. That way you can't change your mind after an orgasm.
Go home and set aside at least an hour. Wash your feet thoroughly. Lightly file the ends of your toenails so they have no sharp edges and are slightly rounded.
Now fit your toe-spreaders. It feels uncomfortable at first, but your foot will soon relax. Shake the bottle of polish and unscrew the cap. Savour that smell. In time, it will become very familiar to you. Paint your toenails. Take your time; if you rush you will make a mistake. Wipe the excess varnish off the brush against the bottle rim. You are better to apply lots of thin coats than one thick one that won't dry well. Apply a single stroke down the centre of the first nail (start with your big toe, it's a big target!) from just beyond the base to the tip. If your nails are long enough, run slightly over the edge at the tip; this will reduce the chances of the polish lifting off. Apply a further stroke either side and lastly across the base if required. Don't redo a stroke you think it looks too uneven; you will only smear drying varnish and make a mess. You are going to build up the colour in layers, so uneven colour will be hidden. However, the rough texture of smeared polish will not be covered.
Repeat on your other toenails, and then let them dry. Admire the feminising effect painting your nails has. Then apply a second coat. Again, let it dry thoroughly. If the colour is still a little thin or uneven, apply a third coat and let this dry.
No matter how excited you are, don't put pantyhose or shoes on until you are certain the polish is completely dry.
Now go about your normal activities. Painted nails will look fabulous through pantyhose so they are strongly recommended. Keep your nails painted for a week before you go shopping for nail polish remover. At work, keep reminding yourself that you have painted toenails. Imagine how your colleagues would react! If any of your colleagues have painted nails on show, ask yourself if you would like to wear their colour next time. Maybe they'll lend it to you if you ask nicely...
19 This is one for sissies with a wife or girlfriend.
Offer your partner a weekend of pampering as a special treat. If she is suspicious of your sudden change in behaviour, tell her that she deserves it for putting up with you or
that you've done.
Explain that you will wait hand & foot on your partner, that you will do whatever she wants, bring breakfast in bed, take her out to dinner (better have this pre-arranged!) & she is not to lift a finger all weekend. If she wants to go shopping, go willingly, carry the bags, and buy something for her. Most of all be the most attentive lover you have ever been. Remember, her pleasure is all. Yours is incidental.
Offer to bathe her, dress her, paint her toenails. She is almost certain to let you do the latter.
So, you get to paint her nails. Let her choose the colour, of course. As you work, talk positively about how much you like painted nails, how different her feet look with them, how much you're enjoying doing it, etc. Try to sound interested and a little envious. If she doesn't offer to do yours for you, make a joke of asking if she'd like to. She'll either think this is a great idea or be glad you're only joking. Either way, you haven't lost anything.
If you do get your toenails painted, make a point of not wearing anything on your feet, so they are constantly on show. Make it clear you are happy to show off your nails. See where it leads.
Even if no crossdressing occurs, you can get your pleasure from serving your 'Mistress'. Be sure to show your subservience. Maybe call her 'Mistress' if the mood is right. Bow on receiving a request (or command), or curtsy if you dare. If the mood is right, ask if she wishes to punish you for any misdemeanours.
Remember, her pleasure is all. Yours is incidental.
20 Make up. Don't you just love it? It can make such a difference to someone's appearance, can't it? With skill and the right tools, one can make eyes appear larger, smaller, closer together, further apart, bright, sleepy, seductive, scary. Lips can appear summery, sultry, fatter, thinner, glossy.
You are to write down a detailed description of the make up of every woman you interact with each day. If you don't see many women close up, write about TV presenters or soap characters. Describe her foundation, blush, eyebrows, eye make up (liner, shadow(s), mascara) and lip make up (lipstick, pencil, gloss). A short comment on her clothing and hair may help place the make up in context for future reference.
Don't just write 'black eyeliner, black mascara'. Describe the exact location of the line, its width, whether it tapers, and so on. For mascara, describe whether this has been applied lightly or heavily, clumped or separated, to outer lashes of upper lid or all over both upper & lower lashes. Describe the colour, position, blending and effect of any eye shadow.
Practice now on this image
As your eye becomes more experienced, you will be able to describe someone's make up as well as any woman. You will take a new look at people you thought you knew well. You will start to recognise the superior make up skills of some women over others. When you find you can do this easily, think how the poor quality make up could be improved; different colours, different position, a lighter touch, maybe?
When you have 25 make up reports written down, sit in front of a mirror and look at your own face. What make up would suit you? Chose a look for day and another for evening. Write it down. Now you have a plan for your own make up. Why not buy what you need and practice?
21 For this task, you will need a lipstick and a compact mirror (one of those fold up mirrors for your handbag/purse). You can choose the colour lipstick you use. A nude colour would be more discrete, but then when were you ever discrete?
You are to go into a large shopping centre/mall at the weekend, when it will be busy. You will have your lipstick and compact with you (you should really be carrying these at all times anyway, sissy).
Take a break from your shopping for pretty clothes to sit and rest for a few minutes. Stop at a cafe for a drink. After your coffee, take out your lipstick and mirror.
You know what you have to do next, don't you sissy?
Uncap your lipstick. Wind up the creamy, phallic column of colour. Look at your lips in the mirror. Bring the lipstick to your mouth. Smell its unmistakeable scent. Stretch your lips over your teeth like an experienced make up user. Run the lipstick over your lips, taking care not to make a wobbly lipline. Blot your lips with a tissue, then repeat. Admire your handiwork. If you've used a nude lipstick, the result may be quite subtle, but everyone in the cafe will have watched you.
What a sissy! No real man would even think of doing what you've just done. That's what they'll be thinking. And they'd be right, wouldn't they? You aren't a real man, you're a sissy who is prepared to put lipstick on in public for the humiliating thrill it gives you.
Now you've done it once, it's easier the second time so next time take a lip gloss as well and finish your lips off with a sticky, wet shine. Maybe mascara and some powder, too. You know you will do this, sissy. You can picture yourself sitting there right now, can't you, girl?
22 For this task you will need pantyhose. If you don't already have some (and I can't believe you don't) buy black 10 denier that will fit you.
This is another shopping humiliation. Wear your pantyhose under your male clothes. DON'T wear socks, but wear your 'male' shoes. You will only display the merest hint of ankle when walking and no-one will notice.
But that isn't your task.
Your task is to go shopping for shoes. If you're really scared at the thought of trying on women's shoes, don't worry. For this task, you can browse men's shoes if you prefer. Your challenge is to try on at least two pairs of shoes. I hope you get help from a sales assistant. I hope it's a woman.
Just imagine; after browsing the display you ask to try on a pair of shoes. You sit and undo your brogues or trainers or whatever. You hesitate to kick off your shoes just yet. After all, you're wearing pantyhose. So, you wait for the assistant to return.
She kneels at your feet and fiddles with the laces of your chosen new shoes. She waits for you to remove yours. She's probably noticed your ankles and doesn't want to miss this. You will be the highlight of her mundane day. You slip your feet out and feel the sudden cool rush of air on your sweaty nylons. She stifles a snigger and her face is contorted to stop her bursting into a grin. She cups your heel in her hand and, despite the intense embarrassment, you feel very aroused at a stranger touching your pantyhose.
She slides your new shoes onto your feet. As always, they slide easily over nylon. "How do they feel, Sir?" If you say they feel loose, maybe she'll offer you a pair of socks. Maybe she'll offer you some women's shoes. Or some pantyhose when you checkout.
If you're feeling adventurous, shave your legs and paint your toenails, too.
You can do this. You can see it happening, can't you. Do it.
23 This task has two parts. Both are to do with your public identity as a sissy.
The first step is to get an appropriate email address, if you don't have one already. It must be clear to anyone who gets a mail from you (using that address) that you are a sissy. There are many free and (fairly) anonymous web-based services you can use. Any address at www.sissify.com will instantly signify your sissiness, for example. Otherwise, incorporate sissy, maid, girl, tv or whatever, into your name email name.
The second step is to tell someone that you are a sissy (not just the sign up page at your new mail server). This is harder. What options do you have? You could try telling your partner (if you have one, but we both know you won't do this); make a random phone call to a stranger (but likely to be viewed as a nuisance call); call a telephone helpline for people with personal problems; better still, a customer support helpline; contact a TV or radio phone in; or email someone you hope will be sympathetic.
If you choose the last and easiest option you must also include details of your level of experience, your bravest public venture and your sexiest fantasy. This is to make you think about your sissiness and stop you just casually sending the message "I'm a sissy". I will accept your confessions if you really can't think of anyone else.
24 Have you ever wondered what it would be like to have sensitive nipples like a woman? Wouldn't you like to get close to orgasm just by caressing them?
Maybe you can.
For this task, you will need two clothespins/pegs, two bulldog clips or a pair of nipple clamps if you have them.
The setting is important. Allow yourself plenty of time. Maybe line up some sexy stories from the net, a video or a selection of women's magazines. Strip naked. Make sure the room is warm enough. Attach a clamp to each nipple so that it squeezes only the nipple, not the surrounding areola. You will feel an intense pain a first but persevere and a warm rush will take over. Aim to keep the clamps on for at least 30 minutes the first time. Watch or read something sexy. Masturbate if you wish, but do not cum.
When you can bear it no longer, remove the clamps. Again, an intense surge of pain as the blood rushes back into your nipples. Now notice how sensitive they feel. This could last up to 24hrs, so make the most of it. Wear something sensual that will brush your nipples, like a silky bra, camisole, blouse or shirt. From time to time, caress your breasts through the material. Brush against your nipples. You don't need to be told to do that, do you, sissy? Do you feel aroused? Do you long for your nipples to be this sensitive all the time? Well, they could be... you just have to take female hormones to grow breasts and shrivel up your already-pathetic boyclit. Would you like that?
(If you already live in panties, this task is not for you.)
What is it about a single item of clothing that can make it so exciting for a sissy? Half the world's population wear them every day, yet some sissies would have a coronary at the thought of wearing a pair of panties. Not from fear, but from excitement.
You are a sissy, aren't you? You would dearly love to replace all your male underwear with silk, satin, mesh and lace panties, strings, thongs and knickers; to reach in your underwear drawer each morning and pull out a pair of black, silk bikinis with lace trim, slide them up your legs, snuggle the soft material around your buttocks and tuck in your boyclit and sissyballs.
So, what's stopping you?
You are to buy seven pairs of panties in your size in one trip from one store. No multipacks. No duplicates. Seven different combinations of style, colour and fabric. What will the shop assistant think when you take so many pairs of panties to the checkout? It's a very odd present for a woman. They must be for you. If she makes any comment, tell her the truth.
Go to a public toilet and change into one of the pairs of panties. Leave your male underwear behind. You won't be needing it again.
Every day, select a new pair of panties to wear and discard an item of male underwear. Enjoy the sensation of silk, satin and lace on your body. Does it make you feel feminine? Imagine, you could be the one wearing the sexiest panties at work. Fantasise about who might have naughtier underwear. You can masturbate, but do not cum.
Every evening, lovingly hand wash your worn panties so you always have a plentiful supply. Keep doing this and you will soon run out of male underclothes. But you won't miss them, will you, sissy?