Sun, Swimming and Sissy (Assignment)

Photo from Mandy-Michell.com

It's summer, sissy! (At least for the northern hemisphere, where most sissies are—sorry southern sissies). You know what that means? Going outside to enjoy the nice, warm sun. Showing a bit of skin with tight, short clothing. And outdoor swimming to tone up your butt, keep you sleek and show off your feminine curves. What's the point of shaving your legs, painting your toenails and toning your body if you're not going to show it off, sissy?

Let me stop you right now and tell you that this assignment is best done on a warm (75 °F/25 °C), sunny day. If you're an unfortunate sissy living in a rainy, overcast-laden locale, wait for a good day before reading and doing this assignment. But if you're a lucky sissy blessed with good weather, carry on!

Now, you might have worn a women's swimming suit before or you might not have one yet. Today it won't matter.

I've espoused my love of the one-piece before (sure you can show off more of your body with a bikini, but there's nothing that screams "I am girly" like a form-fitting one-piece you can't escape or hide like a bikini bottom.

Your assignment today is very simple, sissy: Go play in the water like a girl. First, don your girly swimming suit. One-piece, two-piece (even an amazing three-piece where the bikini bottom ties together!), the specific suit isn't that important. Now get in the water. Done.

(Needless to say, sissy. You shouldn't be cleaning off any nail polish or makeup you might be wearing.)

If you're one of those sissies in denial that hasn't come to terms with the fact she shouldn't be buying men's clothing and all you have is gruff, ugly male swimming trunks, you will have to "make" your own swimming suit. Grab a permanent marker and draw the outline of the suit you are supposed to be wearing. That's right sissy - the line under your breasts, the fabric patch covering your nipples, the straps to hold it in place, the strings of your bikini bottom. You will draw your suit on everywhere you can reach. Finally, as punishment for not accepting your true nature, you'll also write "I am a sissy" on your tummy in big, legible letters. That way, when you buy your one-piece to cover the writing, you can go out and no one will know what a bad girl you've been.

Backyard pool, busy beach, secluded watering hole. The location doesn't matter, as long as you're wet from head to toe. Feel the added weight of the water soaked into your suit. Cherish the gentle caress of your sopping wet suit clinging to you in all the right girly places.

Of course, for more house-bound sissies (or sissies living in deserts), it can be a bit difficult to find a bathing spot. In that case, you can use your bathtub. Fill it up, splash around, and enjoy yourself. Then quickly pull on your (white!) overshirt and shorts if necessary, throw on your sandals and head out to check the mail or walk around the block. No dillydallying, sissy—you'd better me wet in all the right ways when you get outside!

Now that you've taken your first dip into the summer, it may be time for a bit of tanning. Or just lounge around and enjoy your girly attire until it's dry and then put it away for next time. Time to start enjoying the summer, sissy!

Sissy Body Art (Assignment)

Perhaps you may be up for some more sun-baked sissy body art. Unfortunately, many sissies are still faced with sour weather. Plus, suntans have a lack of fidelity. They can also be difficult for many sissies to apply. Fair-skinned sissies often risk sunburns and dry skin; ebony sissies may have trouble getting their art to show up at all.

Luckily there's another option: drawn-on body art. (And for the sissies that have already taken the next step and gotten an actual feminine tattoo: Way to go girl! Your dedication to girliness is an inspiration!)

Find a fine-tipped permanent marker (or my favorite for that extra feminine touch for a sissy: a lipstain) and pick out a design you like. For sissies with limited artistic experience, a simple shape will work best (the shoulder star like Bianca here, a Venus symbol, a bow). In a pinch, a short word also works well. Capital letters are easier to write neatly - even if you've been practicing your girly handwriting, writing on yourself may be difficult. If you can't think of anything else, labelling yourself SISSY would be just perfect!

 But you don't want to hide your art away!

You have to show it off, sissy. If you're not quite brave enough to go with a fully bared piece of body art, you're going to go as close as you can: Your shoulder/upper arm, lower thigh or ankle (hidden, but just barely). No need to worry if you have concerns about your drawing skills - you've got plenty of places elsewhere on your body to practice where no one will see! You can try to draw or trace a pattern in pen and then fill it in with a more permanent solution later on. Or try free-hand if you're a bit more confident (short strokes will work better as you flesh out your design, the marker will naturally bleed over a bit into the surrounding skin).

Once you're done, you'll have a neat little girly reminder that's just a wrinkle or ruffle of clothing away. A raised sleeve, a lowered sock and you'll be able to show off your girly art!

Most permanent ink will wash off within a few days (depending on your marker, it may become much less visible after just one wash - feel free to touch it up as you see fit). If you have sensitive skin, test out a marker first to make sure you won't have any unfortunate rashes or uncomfortable events to ruin your artistic experience.

Most importantly - have fun and express your inner sissy!

With Love from Sissy (Assignment)

Happy Valentine's Day, Sissies!

Hopefully you've gone and handed someone you fancy a valentine signed with your girly name (if not, there's still time!). There's no better way you show your appreciation than to make your feelings known.

But Valentine's Day is about love, so it's a great time to show your love for your girly side, too.

And what better way to show your love for your sissy side and your special someone than by practicing your girly voice while singing a love song? Time to serenade the love of your life with an appropriately girly tune (or at least practice). Not much practice talking like a girl? You should really remedy that, sissy.

You're the only one that can know the perfect song to represent your feelings, but there are tons and tons to choose from. Maybe you're a bit addicted to that person you love? Or they're the fuel for your flame? Or maybe you're just hoping they'll make the first move? 

Find your girly voice and try to talk out what you love about being a girl and your special someone. Make sure you've got your voice nice and solid in your girly range (no accidental squeaking or falling back to your dull male voice). Then practice your song a few times (since some of you sissies cheat and don't follow through: that's 3 practice tries, sissy).

Then it's time to belt it out like a sissy diva. Extra bonus points for doing it properly dressed and in front of your beloved (but don't worry if you're too shy to openly profess your love of being a sissy and your love of that special someone).

Ending the Addiction (Sissy Lifestyle)

It's a sad fact that many sissies just have not embraced the comfort, variety, beauty and femininity of panties as everyday wear. Some sissies choose to go each day wearing gross tighty whiteys or unflattering boxers. You are girly and feminine and beautiful—You deserve to wear panties, sissy!

Unfortunately, switching over to panties in one fell-swoop is not feasible for most sissies. Male underwear is an addiction you have to break, girl. And just like smoking, going cold turkey usually ends with poor results. Some sissies have a fear that people will notice, some start too lavishly and can't find panties to wear every day (ironically named boyshorts are perfect if your clitty is being bothersome!). And some sissies have to contend with snooping roommates and family members—so it can be important to go slow.

Needless to say, if you don't even have any girly underwear, your first step is going to have to be buying panties (I recommend using packs of underwear to help build your wardrobe at first).

Now to get on the road to recovering from icky men's underwear. Naturally, if you're here, you should already be wearing a pair of sleek, comfortable, girly panties.

Now gather up all your inappropriate male underwear. How many pairs do you have sissy? That's how many weeks you'll be working on your assignment. Grab a permanent marker or a scissors. It's time for your weekly ritual. And remember: never touch yourself before you complete your assignment.

Start by repeating this:

I promise never to buy men's underwear ever again. 

I am a sissy that deserves to wear women's underwear.

Panties make me confident, sexy and feminine.

Good girl! Repeat as many times as necessary.

Image from Shemale Yum

Now look through your old, stale men's underwear. Find any that have holes or tears and get rid of them. Write "NOT FOR SISSIES" with your marker or simply cut them to pieces. Then throw them out. Think about it sissy, why do you have these tattered clothes? There's no good reason to keep them around.

If you carefully handle your clothes and have a suitable dainty lifestyle (or you're on your second week), you may find that all of your bland male underwear is in tip-top shape (at least in terms of fabric quality). In that case, take your most stained, dirtiest or frayed underwear and get rid of it the same way as before.

Once your old male underwear is tattered remnants or properly marked, throw it in the trash where it belongs.

This will be your weekly endeavor. Set aside a day each week and do it like a good girl. You will slowly wean yourself off the unnecessary habit of wearing men's underwear. As a bonus: more room for awesome girly panties or other clothes in your wardrobe.

(For secretive sissies: other people, like family members or a wife are still allowed to buy underwear for you. You are not allowed to ask them to do it. And you're still going to have to do all the weeks you set forth at the start.)

Moving

Your song needs to be from this year. Maybe you like retro clubs and like to be a hipster that listed to classic rock, but in order to be trendy and fluid at modern clubs you'll need to work with something more modern.

It needs to be sung by a girl. You are not some masculine, chiseled baritone - you are a sissy girl and you're going to practice singing like a girl. Girly lyrics are a definite plus; referring to yourself as a girl or queen in song will always help in the long-term.

Lastly it needs to be upbeat, with a fast tempo. Something you can move and dance to. None of that shuffling shit. Get down, swing your ass and move your arms (with the rhythm, obviously).

If you're not up on modern hits and pop music you can always try one of these:

Love on Top - Beyonce

Call me Maybe - Carly Rae Jepsen

Bad Girls - M.I.A.

 And then you're going to practice singing the song you pick at least once per day (as feminine-sounding as you can - I expect progressive improvement). You'll also dance to it, but you're also going to dance to other songs as well -- at least 15 minutes of sexy, sensual dancing in rhythm with the music you choose. You can start by watching videos (you don't need to stick with modern music for practicing dancing Britney Spears, Beyonce, Shakira and many others are good places to start, whether or not you like the music). But you will dance and practice what you see.

I expect you to work at this and become a passable dancer for cheering on your favorite athlete(s) in the last day of the Olympics, but you're going to keep practicing with new songs and new dances. Clubbing and dancing is the favorite weekend activity of many young women, so it's time you learned how much you love it too (the fact that it will help you get fit, move more sensually and maybe act a bit sluttier is just a bonus).



This is an excellent starting step to get you outside, confident enough to dance and hangout in front of other people. Now get out there and start shaking that moneymaker, sissy.

- <3 Regina

Body Art for Regina

That's right, you're going to use your art project as a stencil to create an untanned symbol expressing your femininity.

You'll still need your marker and you may want to get some paper of a heavier stock to help with your assignment. If you've printed off and cut out a symbol, you could trace it on heavier paper and get a sturdier stencil (remember sissy: losing or accidentally destroying your art project is unacceptable!).

Like neglecting to repeat your mantra proves, sissies are pathetic and forgetful. So you'll start by picking where you want your tanned-on tattoo to go. Pick a surface you can reach and keep flat while tanning. Now take your marker (a Sharpie works well) and trace your symbol. This is to help remind you to go tanning and to help you know where to put your symbol before the contrast becomes noticeable (unlike your tanned skin, a "permanent" marker will usually wash off in 2-4 days).

Now either tape or - if you're using heavier paper - glue the symbol in place before you start tanning.

Heavier paper also plays a role here. Thinner paper won't block as much UV radiation, so it'll take longer to notice. You can opt to tan outside or at a tanning salon, whichever is easier (a tanning salon will likely be easier to keep private and on time). Working on sissy tanlines with a bra and panties or two-piece swimming suit is optional, but encouraged (most girls like to avoid having lines).

Natalie would be pissed if I didn't make some disclaimer for some of you dumber bimbo sissies: don't tan every day and don't bake yourself in the sun for prolonged periods - you'll risk ruining your tan and that will not make your mistress happy.

And you had better keep your symbol intact and in perfect condition. Too bad if someone might see it or find it -  your mistress demands that you keep it safe and that you continue to use it until you have a clearly visible sissy symbol (not)-tanned onto your skin. Feel free to make a duplicate and use that for the actual tanning.


And remember sissy: on days when you have to tan you are not allowed to cum or even touch your pathetic excuse for a clit until after you've tanned. Obviously you shouldn't be touching it at all, but I'm realistic in my expectations of what horny little sissies will do.

I'll make a good sissy out of you yet.

- <3 Regina

Art for Regina

Art class - a perfect time to express your femininity and for you to stop hiding behind your pathetic, transparent attempts at being "masculine".

Obviously we'll need some art supplies. To start with, you'll need a marker or a printer, some paper and a scissors (or something else to cut paper). Heavier stock paper will work better in the long run.

Now either print the image below or draw a suitably feminine shape of your own (none of that "unisex" bullshit for you to try to veil the fact that you're a sissy). You'll only need one shape, but you'll be cutting it out, so don't do anything too fancy.

Make it about 3.5 centimeter (1.5 inches) tall. This is pretty small, but if you make a mistake start over - the shape had better be fucking spot on once you're done. Plenty of opportunity to give your nimble, feminine hands working.

Now that you have your design make sure it stays perfectly flat. You wrinkle it or fold it and you'd damn well make a new one, sissy. Carefully write your name on it so people will know whose it is. Then just leave it sit out somewhere safe and out of the way.



After it has had some suitable public appreciation we'll get started with the next part. Make sure you have some glue or you know how to make papier maché paste.


The summer is young sissy. I'm going to make sure we've gotten those misplaced ideas that you're anything but a sissy out of your head soon enough.

- <3 Regina

Girl Time (Assignment)

Many sissy blogs have an overt fixation on sex, without a focus on much else (over the last month or so this is probably true for the Sissy Spot as well). This is understandable, since many sissies are, in fact, perpetually horny and have an overt fixation on sex. Sissies often have a very high sex drive - even if they're not able to exercise it (due to chastity belts or for other reasons).

But whether you hope to become (or your mistress is transforming you into) a cock-crazed super slut or you want to be a more down-to-earth, feminine counterpart to your old male self, there's a simple truth. There's no way your life could exclusively consist of sex and sleeping. Sex is tiring work.

So today we're going to help you get in touch with your sissy side, even during down time. Being girly during daily life is far more enduring and important than just being dressed in girl's clothes for 15 minutes while you rub your clitty through your panties.

So tomorrow after you get home from work or class (or when you wake up, if you have nothing to do tomorrow), you're going to start relaxing like a girl. Of course, like many fun, feminine things this will actually take a little work at first ("Work to relax, Natalie?" I hear you cry. Yes! That's how it becomes routine, more enjoyable and easier to slip into without thinking about it).

You'll have to start with loose relaxation clothes. I recommend panties, a loose-fitting dress and some stockings. If you're a very under-stocked sissy, you could even get by with boxers (or pajama bottoms) and an over-sized T-shirt, but then you'll need to be absolutely sure you don't do any of your stressful, old masculine leisure activities. Then you'll need to put on a little make-up. Blush, lipstick and eyeshadow would be sufficient; you can go more in-depth if you want, but it really needs to be "quick jaunt to the store make-up" - a light application.

If you've gone full-on raccoon eyeliner and porn star-esque lipliner you've certainly gone too far. A good benchmark: you'll know you're wearing make up, but if someone didn't know how you looked saw you, they wouldn't notice that you're wearing any.

Now you're ready to relax until you have to go to sleep. What to do to relax? One of my favorite things is to curl up with a stuffed animal and watch a nice movie. A "chick flick", a childhood favorite or a simple drama would be best. Naturally plenty of actual girls like action or sci-fi, but you'll need something softer and more cerebral for this assignment.

Alternatively you could practice giving yourself a manicure or pedicure - they can be quite relaxing when done right (of course). An excellent option is to take a lovely, scented body lotion and give yourself a massage (you'll also have the side-benefit of smelling very femme!).L Listening to music and chatting are also good girly past times. Reading (if in doubt find a female author) or doing puzzles will work nicely as well.

Just make sure you're doing things you enjoy that you wouldn't be doing in "boy mode" (or however you want to refer to those boring things you pretend to enjoy when not being true to your sissy self).

There's only one thing you mustn't do. You are absolutely, positively not allowed to touch your clitty. No sex, no masturbation. Dressing like a girl may still excite you, but sex is only a very small portion of what you do during the day, so it's time to practice something else instead of rubbing yourself to orgasm. This also has the side benefit of keeping you a bit more focused on being girly.

So get out there and relax, sissy :D

Come Off (Assignment)

Cum is a wonderful thing. It is an adhesive, an invisible ink, a means of procreation. For some cultures (or people) it is the flavoring of choice. It's even suspected to be an anti-depressant (I think that means you know what to do the next time you're feeling a little down :D ). But for a sissy the greatest use is probably as a symbol of submission and femininity.

Macho, masculine guys are never supplicant. They never dream or hope to kneel down in front of a guy to show their ability at serving cock. They don't hope to feel the warm burst of cum splashing on their face or inside their mouth.

Remember make-off, sissy? Your assignment is very similar, with some key differences.

You've got another chance to practice your perfect, feminine make-up. You'll certainly want a minimum of lipstick (or gloss), blush, eyeshadow and something a bit more enduring like eyeliner or mascara. Be sure to give your inner sissy the time she deserves, and don't feel obligated rush to get the make-up off.

Now you're going to discover a new use for cum: as a make-up remover.

That's right, you're going to cum or (if you're a very lucky sissy) use someone else's cum to clean off your face. And to help you stay true to your assignment, you must ruin your first orgasm. That way you'll have some cum to work with and you have a better chance of controlling your bothersome other half.

(If you're not familiar with "ruining" an orgasm, this is when you stop stroking your clitty the moment before you cum. Stroke until an instant before you orgasm and then take your hand away. You'll still cum, but it will not be your usual orgasm.)

All you may use to clean off your make-up for the next 24 hours is cum. And you'll have another wonderful use for cum. It's certainly not the most healthful or efficient use of cum (and some sissies may need to ask permission if their mistress has ordered them to drink every drop), but every sissy need to experience the feeling of having dried cum all over her face (and if you might happen to need to explain why you're wearing eyeliner and why you so obviously smell like cum, that's just a side benefit).

You can always elect to not try cleaning off your make-up for the day. Cum getting in your eyes does sting, after all.

(And, as before: safety first. Even if you're cowardly male side is desperate to clean off your make-up, be very careful about rubbing your eyes. They can take the pH change from cum easily (even if it stings), but rubbing bits of powder or dust under your eyelids inadvertently when wiping your eyes can be harmful)

Bracelet (Sissy Lifestyle)

Has shaving become so second nature that you don't even remember adopting a sissy lifestyle? Then it's time to add a new accessory to your sissyness with a new sissy lifeestyle change.


Men do not accessorize very well. Most men do not happily wear jewelry and accessories. A watch or a ring may be dutifully worn for work or marriage. Some men may even wear a necklace or bracelet for remembrance or religion, but very rarely do they vary their accessories or wear anything delicate and feminine. Of course, you're different sissy. You would love to wear something girly. Something that exhibits your inner femininity.

That's why it's time to get your very own sissy bracelet.

It doesn't need to be flashy or personalized (although that doesn't hurt). It doesn't need to be fragile or difficult to handle, either. In fact, a delicate necklace made of pink or purple glass (or plastic) beads would be perfect. Something beautiful, durable and easy to put on would be perfect.

If you're into arts and crafts this is a perfect opportunity to give your inner sissy the memory of a childhood activity; you could buy the materials to make an even more personalized bracelet (nothing says "I love my inner sissy" like a bracelet that you wear every day with her name on it!).

This will be your go to accessory. Many sissies are still a bit hesitant to announce their femininity to the world, so fully dressing up as you'd like may not be an option. But your sissy bracelet will be there to make sure you're always reminded of who you truly are. You'll take it off for bed and put it on your nightstand. You'll slip it on first thing in the morning. Whenever you're alone it will be there, gracefully dangling from your wrist.

You're going to keep this bracelet on-hand at all times (although you need not wear it if others are around). You'll wear it whenever you're alone - especially if you're pretending to trounce around like a man instead of dressed up like the sissy girl you are (you need not actually wear it in the shower or swimming or the like - just have it nearby in such cases).

The rationale for your new sissy bracelet is two-fold: exhibiting your femininity and remind you of your femininity.

Unlike panties or bras or even stockings or toenail polish, a bracelet is eminently visible, flashy and very feminine. You may be sitting at your computer, but a glimpse down at your wrist will remind you of the sissy inside that you shouldn't be ignoring. In addition, bracelets and other jewelry are a basic accessory that women all over the world use to express their personality, fashion sense and to draw attention.

The most important function of the bracelet will only become apparent after you've worn it consistently for a few days. Many sissies have not advanced far enough that they're willing to dress and express their femininity in public - at work or out and about. Since you only have to wear the bracelet when you're alone, you still won't need to wear the bracelet in such situations. But because you'll be wearing it every chance you get, you'll get used to it. You'll start to notice how bare your wrist feels without it. You'll be reminded of the weight and meaning and femininity.

You may just want to keep your sissy bracelet proudly on display all the time.

Say it Sissy (Assignment)

It's true: many sissies are of few words. For some sissies it's because they're demure, good little girls; for others it's because they're face is too stuffed to give out anything but a satisfied moan. But for many sissies, it's simply because they're focused on overt things like makeup or clothes or boobs.

But how could any sissy truly hope to reach her true potential if she's too embarrassed or impatient to bring out her own natural, harmonious feminine voice?

First things first: you'll need to practice getting rid of your heavy, masculine tones. There are a few methods for doing this. And unfortunately, just talking with a high-pitched voice won't cut it. There are many videos that can help you with this and many techniques, so you'll need to find one that works. I can start you with this series start. For girls short on time there's a potentially quicker option:

• Grab a pillow (or something else to mask noise - if needed) 
• Take a deep breath 
• Cover your mouth/face with the pillow and then gargle with your voice until it's at the lowest pitch you can get to without it cracking
• Say, "The wicked witch of the west" repeatedly (30 times or more)
• Repeat it many more times while trying to sound like an old person 
• Try to maintain that adjustment while speaking normal sentences.

Of course, each sissy will learn differently, so you'll have to experiment. It may be difficult to judge what you actually sound like, so you may want to use a microphone and Windows Sound Recorder or something like Audacity to check yourself.


Then it's time to practice! For the next 6 hours after you practice try to keep in tune. If you lead a very lonely life or are still hiding your sissy nature, it may be time for a soliloquy about how much of a girl you aspire to be. Or perhaps your love of cock or of women. You may also want to practice some suitable songs.

And since sex and expression are a focal point for sissies, the most important part of your assignment: every time you masturbate you are going to moan and whimper like cock-crazed sissy every time you rub and stroke your clitty. This is surely the part that many sissies will excel at (they may not be able to speak like a girl, but many of them can certainly moan like one).

Of course, you've been practicing your voice, so you'll certainly want to throw in some exclamations about how much you love things on you and inside of you.


Try not to wake the neighbors, sissy :D

Gloss (Assignment)

Nicely shaven but nothing else coming to mind? Don't worry, sissy - there's always more for your sissy self to do!

As far as make-up goes, the lips are only second to the eyes for the amount of attention they get. But the two main options are lip gloss and lipstick. Lip gloss is a relatively new feminine fashion item (it was created in the 1930s to help the shine of lips show up better in movies, when contrast and the play of light was more important than pure color). Lipstick has also been a centerpiece of feminine beauty for thousands of years, so it's not something to be easily dismissed.

The fullness and color of lips can speak volumes about mood, health and attitude. For instance, blood flow increases to the lips when aroused or excited. Dark, full red lips were not just indicative health, but also of arousal and sexuality - no wonder many women have a variety of colors at their disposal! Just like you should, sissy.

Naturally, for an assignment related to lipstick you're going to need a tube of lipstick or lip gloss. You'll want the most neutral, natural color you have. Many sissies over-compensate for their perceived lack of femininity by using accentuated color or too much make-up. In order to be more properly feminine and natural you'll want to avoid bright, very noticeable colors (the point of make-up is, after all, to use cosmetics to enhance your features - not cover them up!). Plus, you're going to be wearing that lipstick outside, so unless you're an outgoing sissy you'll probably want something subtle.

That's right. In the morning you're going to put on a very light layer of lipstick (or lip gloss). And you're going to wear it the whole day.

If you have a color that perfectly matches your lips, great! If you have a color that slightly enhances the color of your lips - even better! Just gently apply the tube or applicator across your bottom lip; then use your upper lip to smooth it over both lips. You should have a thin, subtle layer of lip color on your lips. And now you're ready to start your day!

It's true: someone may notice your feminine affectations. But if they do you can be happy that someone is interested in you enough to notice something very subtle about you, like a slight color change in your lips. But a vast majority of people (especially men) don't pay attention to the nuance of someone else's lips, and even a significant change will usually go unnoticed if it's not garish or too pale.

So you can get the confidence of wearing make-up out and about, your sissy side will get to practice her application of true, subtle, feminine make-up. Maybe you'll find that a faint application of lipstick is an addictive addition to your morning routine as the confidence-building, emboldening activity adds a unique sissy gloss to your day. :D

Bare (Sissy Lifestyle)

Assignments are great - I have fun making them and doing them (and they seem to be a favorite for people not stopping by for a quick fap - not to knock fapping, it's necessary with an unrestrained sissy's sexual drive). But there's only so much you can do with a task that lasts one or two days that any sissy can easily complete. So today is the first Sissy Lifestyle assignment.

Sissy Lifestyle assignments are for sissies that have come to embrace their inner girl. And while you might not be ready to shout from the rooftops that you are a sissy, you're ready to invest more of your time and money into her needs (after all, if you spend $50 on clothes in a month, how fair is it that she gets nothing?).

Now you see it...

Since most sissies are diving into the depths of winter and since this is the first sissy lifestyle assignment, we'll start easy: shaving. Nothing to buy, nothing to risk. All you'll need is a little time.

Women generally have finer body hair than men. It is also thinner and grows in fewer places. For instance, women do not generally get hair on their breasts, whereas a hairy chest is often a sign of manliness (and many men have hair around their nipples). Underarm and leg shaving is all the rage throughout the world (for women - so that means for you too, sissy!) - whether for aesthetic, athletic or religious reasons.

For this sissy lifestyle assignment you are going to spend the winter keeping yourself shaved like a woman in the most inconspicuous places. The first day will certainly be the most daunting, since you'll have the most work (as you end up shaving more often and with more skill it will go faster and require less clean up). You can remove the hair any way you like, but I very much recommend against an electric razor (it's easier to get razor burn and the shave isn't close).

Now you don't...

Shaving is best done in or right after a shower or bath, when your pores are open and the hair follicles are most accessible. Since most sissies don't have the funds or courage to go for full facial hair removal you might as well start there and shave normally. For the purposes of this assignment you are going to shave your legs and your underarms - the two (and, in the winter, very clandestine) parts of your body destined for feminization first. If you're very hairy, or a more courageous sissy, you should also shave your chest and back.

(I haven't included the pubic area since that is up to you - a woman's or sissy's decision to shave down below is her own preference (but may I recommend a heart shape? :D)).

Leg shaving can be very tricky, so you may want to consult a wiki. Remember that if you have a fresh, sharp blade you really don't need any pressure, just pull the blade gently and smoothly along the skin. And if you have sensitive skin or skin prone to in-grown hairs, shave with the grain multiple times instead of shaving against the grain (for the legs, this would be downwards instead of upwards).

Making it a Lifestyle

Of course, now you'll need a normal shaving schedule, sissy!

Many women shave their legs every 3 to 5 days since leg hair stubble becomes more noticeable after about 72 hours. You'll certainly want to match their feminine routine. Every 3 (or 4 if you want to set it to specific days of the week) you are going to shave your armpits and your legs. And you're going to continue that routine until April.

Of course, by then you may be so locked in your routine that you won't have any inclination to stop. After all, you could always claim you're shaving for other reasons in addition to becoming a better sissy!

Unpolished (Assignment)

When I was in high school I once used my sister's clear nail polish . Not the most observant girl back in those days, I enjoyed putting the polish on, but completely forgot I was wearing it. That is, until I was sitting at lunch at school the next day and saw that my nails seemed to be ...quite a bit more reflective than I remembered. As far as I know, not one noticed my nuanced femininity and instilled some confidence in me to be a bit more bold with my sissydom.

Today your inner sissy will be a bit more bold, but it may be difficult. Assignments where you have to not do something can be the hardest of all. Sissies tend to be very easy to arouse sexually and many cum very easily (that is why it's never a bad idea for a mistress to invest in a chastity cage - if only to use a few hours at a time). But let's get started!

You'll need to find a pale or light-colored nail polish (although daring sissies can certainly go darker). I suggest a light pink, nude or light red.

And paint your nails - toes and fingers, left and right. You're only using one layer, so make sure it's smooth and covers the whole nail bed, but doesn't smear onto your cuticle or fingertip. This assignment will naturally be easier if you're adept with your polish and don't get it all over your cuticles (perhaps if you've given yourself a pedicure before). Let it dry. Read some Elle or take some quizzes.

Once the lacquer is dry be sure to get plenty of girl use out of your effort. Wiggle your fingers and toes. Look at how lovely they look when they're painted. How they shimmer and shine with glossy perfection. Just think - you're doing something that only girls and aspiring girls ever do!

The one thing you must not do is stroke your clitty.

Once you're done admiring vibrant femininity, get 1 (one!) nail polish remover pad. If you don't have pads take one cotton ball or paper towel. Soak it with as much remover as you like, but then cap your remover and get rid of it. Make it as inaccessible as you can to try to help dissuade your cowardly masculine side from ruining your sissy's improvement.

That is all the remover you get - so make it count. Remove as much nail polish as you can (unless you're a very pro-sandal sissy, I recommend starting with your fingers). Very anxious sissies may want to completely avoid their toes to get as much from their fingers as possible.

Naturally the pad will not be able to get all of the polish (obviously that is the point, sissy!). You'll likely be left with small flecks of nail polish around the edge of your cuticles (bold sissies that have much more on their fingers might be better off just redoing their polish and playing off their colored nails as a dare :D ). But don't worry - most people won't be observant enough to notice that you've got the remnants of a sissy lifestyle shimmering all over your nails.

This is obviously not the most classy look. As a beauty-conscious sissy you'll either want to re-paint your nails or clean them completely tomorrow.

Alternatively: sissies can try clear nail polish without any remover.

A Day Off (Assignment)

Oh, not from being a sissy. You and me both know that never happens. Even when you're not dressed in soft, pretty panties and dolled up in your best make-up you're still a sissy.

No, I mean making your male side take a day or two off from ruining your sissy development. Most sissies fap at least once per day (some very horny sissies do so much more often), but immediately after you orgasm your sissy desires immediately subside. Your inner sissy's drive to slurp and suck the cum from your hand; the desire to keep your perfect make-up on all day; the will to go out in public dressed completely as your true feminine self - all that goes away when you cum.

It's incredibly difficult for you to stay a sissy cum slut or even a good sissy maid right after you cum.


So for the next two days indulge any sissy fantasy you have. Wear your panties to work for the first time. Paint your nails. Go to sleep fully made-up. Play dress-up with everything you have (even try folding or taping some of your clothes to look more feminine if your wardrobe is a little sparse). If you're a very outgoing sissy you may even want to go outside and find something interesting to do. But however you spend your time do not cum.

You can even rub your clitty, so long as you have the restraint to keep your inner sissy in control and not making cummies.


And, as a bonus for sissy cum sluts in the audience, after two days there will be plenty more cum for you to enjoy!

Truth or Dare 3

Recovered from the last Truth or Dare, sissy?

Truth or Dare is great for all sorts of sissies, since it gives every level of girl a choice. Locked up sissies can explore their feminine drive and ambition, while outgoing sissies can try to be a bit more daring. Which one you are is up to you!

Truth: Have you ever worn a girl's swimming suit?

Swimming suits are often one of the first true girl clothes that sissies with like-aged siblings wear. Clothes are very interchangeable until puberty - except swimming suits. Girls often have onepiece swimming suits, which are a far cry from the loose boxer shorts boys get. And young sissies often end up wearing them at least once - either because they're curious, or their sisters force them.

There's something particularly feminine about a one-piece swimming suit. The form-fitting design acts as a bra and panties in one and the close design emphasizes curves. It encases the torso in a layer of femininity. Some curious girls make their boyfriends wear a bra and panties as a joke; a guy might wear a dress on Halloween, but from high school onwards only sissies and women will ever wear one-piece swimming suits. But of course, there are bikinis and other sorts of swimming suits as well.

But have you really worn one, sissy? How did you feel? Swaddled in femininity. Pretending to be a pretty beach bimbo? Or just a cute girl lounging on the beach?

Dare: I dare you to go swimming in a girl's swimming suit.

The timing of this dare may seem a bit off - most of the planet's sissies are slowly moving into winter. But this means your dream swimming suit - bikini or onepiece - will likely be discounted. Although Australian and other Southern hemisphere sissies can go out and swim right away.

Feel the wet, tightened fabric cling to your curves. Enjoy the feeling of your stiff nipples in the cups of the suit. Embrace the femininity of gracefully swimming in something that no man would ever wear. And of course, when you get out you can watch the water stream down the crotch of the suit - something that never happens in baggy, gross man shorts.

It doesn't have to be a long swim. It doesn't even have to be at a populated area (in fact, sissies out to swim on deserted beaches would probably benefit now as well). I also heartily insist that you lounge in your beautiful swimming suit, drying off in the sun. But that's not explicitly part of the dare - just something you should try, sissy.


For most sissies now would be an apt time to buy a suit, and then June will be an excellent time to test out the suit (possibly working your way into fitting into it, if you're a bit too afraid to try and buy one in person).

Rolling for More Femininity (Game)

It's time to break out your pink sissy dice and roll once again. Or if you haven't rolled yet, you can start with the first rolling game. You've got a chance at 6 simple tasks any sissy can do!

Your legs are going to be glued together tomorrow. No matter if you're standing or sitting or jumping or trying to run - your thighs must stay next to each other. You can separate them for up to 20 seconds every hour (to clean or wipe or stretch). Otherwise you'll be in the closed feminine stance of having your legs together.

You're going to put on lipstick and wear it off instead of wiping it off. My recommendation is pursing your lips and kissing a pure white sheet of paper so you can keep a record of your sissy escapade hung up on your wall. If you don't have something as simple as lipstick, you'll have to use something like a washable marker (I'll warn adventurous sissies that any non-yellow, non-red color is going to be difficult to wash off - washable or not). You can drink water (or perhaps a more alluring fluid) out of a glass, eat, lick your lips or do anything else you want - aside from wipe off your lipstick. Until you go to bed, where you can clean up the (small) trace that should be left.

It's winter now, so long-sleeve shirts and pants are the norm. There's no reason for you to worry about people seeing your feminine, hairless body after you shave. Which is what you're going to do: shave your legs, your arms, your chest, and your arm pits. Just like a dedicated girl trying to impress!

It's time to practice your handwriting for all the world to see. Everything you write tomorrow is going to be immaculate, smooth and flowing. Even if you must sign your name - you'll put in the effort to make it look neat and feminine (even if it's something official like a driver's licence or a cheque).

Today you're going to claim the bathroom for your own makeover (hopefully you don't share a bathroom with anybody, sissy!). Many sissies have fantasies about being dressed in French Maid uniforms and cleaning ...well, the outfit isn't necessary here, but first you're going to make sure the counter space and mirror are clean and unblemished. Then you're going to lay out all of the cosmetics you have as though this were going to be where you were going to put on makeup every morning. Then make yourself up. You can then put away your cosmetics...but really, you're just making more work for yourself, sissy.

The simplest task - especially for sissies that do it already. You're going to paint your toenails (in tune with the assignment before). And you're going to leave that polish on until it starts to wear off or until your fingernails extend half a centimeter (about 3/16th of an inch) out from your fingertips. And, of course, if you don't have nail polish then you'll either have to buy some or use a permanent marker.

There's no reason to give in to paranoia like "what if I get injured on my way to work and get stuck in the hospital." If you're in the hospital your loved ones' first question will not be about your pretty toenails. Don't let your cowardly male side subvert your inner sissy's joy!

Happy rolling, sissies!

Sheer Denier (Assignment)

I know, some of you sissies might still be working on my last assignment, but it's a special time of year for sissies that I want to make sure you don't pass up.

That's right, Halloween!

Many sissies choose to let their inner girl run free on Halloween. It's the one day of the year where she can be completely uninhibited. Make-up, dresses, skirts, cheerleader outfits - anything works (although dedicated sissies may get odd looks if panties are involved. But there are other sissies who completely neglect this holiday and keep their inner girl locked up tight. Well not this time. If nothing else you are going to buy a small present for her.

It doesn't matter if you're a poor college student, living with your parents, a closet sissy hiding your femininity from your wife, or a free-spirited sissy who loves to go out dressed to the nines. You need to buy pantyhose tomorrow (also called tights in some countries). You are going to go to a department store, a drugstore, a pharmacy - wherever you can find pantyhose. And you are going to splurge on your inner sissy and buy her a pair. Get pink or flesh-toned or black or white - whatever calls out to your femininity. But whichever denier/sheerness you want (smoother will feel more sensual, but is easier to damage).

And since it is Halloween pansy little sissies can claim they are buying the tights for a costume. Ask a clerk for help if you wish (or wander around until you find them, whichever will get you in those tights). Make sure they fit by reading the packaging on the back, though, sissy. There is usually sizing information on the back.

There's absolutely no reason you shouldn't be wearing a pair of pantyhose tomorrow. This is $2 (or 1£/1.50€) that your sissy deserves. If you have to miss a meal to buy them your inner girl won't mind, trust me.


Put them on by rolling them down to the footy for one leg. Stick your foot in and pull them tight by pressing your hand against the fabric and sliding it tight (don't use your fingernails, that's how you get runs in your pantyhose). Once you have one leg up high enough, follow suit with the other leg. Once they're above your knees you can grab them by the waistband and bring them up to settle on your hips (pulling them up with your palms as necessary). Then enjoy the sensual, smooth feel of your budding femininity wrapped around your legs.

Of course, they're better with smooth legs, but some sissies are too afraid to shave.

Inspired sissies may want to go all out with the "I'm dressing as a girl for Halloween" excuse and pick-up all the makeup they can carry. Of course, sissies completely comfortable with picking up their feminine articles whenever they need them will have cut out one errand from their future.

Much love and luck to you sissies! And a Happy Halloween (probably dressed as a girl :D )!

Limp (Assignment)

No, not that kind of limp, sissy.

Gestures and mannerisms are an important part of femininity. Most women are more physically expressive than men, but their gestures are also more subtle. Most men don't have the long flowing hair (or the inclination like you do, sissy) to twirl or flip their hair. Most men don't have the breadth of emotion or awareness to bite their lip when they're unsure or aroused. But many sissies are too afraid that someone will notice their womanly gesticulations so they don't practice or reinforce what may come naturally.

Keeping your legs together when possible and not "spreading eagle" when you sit down are both good examples of body language a good sissy should try to emulate, but they're also very obvious. A sissy pretending to be a man doesn't have much of disguise if she folds one leg over the other and always keeps her elbows at her sides. And although a sissy should never really hide her inner girl, it's an inevitable fact that many do.



But there is a gesture that can be very subtle and very feminine: the limp wrist.

A limp wrist shows submissiveness and docility. Female executives are taught to expunge this gesture from their repertoire since it implies defenselessness and weakness. Its use by women is so commonplace that the term "limp-wrist" is often associated with gay men striving for femininity - but that's not applicable here, sissy. You are a sissy realizing her feminine nature.


Your goal for the next week is to consciously do what subconsciously comes to many women: have limp wrists (until it becomes second nature to you too, sissy). If at all possible your wrists should be bent. Your fingers should never be aligned with your forearm; the back of your wrist should not form a line with the back of your forearm. If you're laying your hands on your lap make sure your wrists are slightly bent. Unless of course you're doing something that can only be done with straight wrists (such as typing).

After a week your muscle memory is sure to have gotten in tune with your feminine self and you should be limp whenever it's appropriate.

As a computer-savvy sissy (you are visiting this blog, after all), you can always say you're bending your wrists as physical exercise to alleviate carpal tunnel syndrome...and to reinforce your femininity.

Make-Off (Assignment)

Make-up is an important part of being a sissy. There's something extra feminine about pampering your face and your nails and even your entire body to make it the most beautiful, sexy version of yourself.

If you can do this assignment in the morning it will likely be more effective for your overall growth as a sissy.

But many sissies don't dare to wear this mask of femininity in public. Many home-bound sissies are extra meticulous in making sure that no hint of their feminine aspirations is visible to the outside world. They scrub and wipe while they stare at a mirror to remove every trace of femininity enhancing powders and creams from their faces.

Today you're not going to be that OCD, sissy. The opposite, in fact.

You are going to dress to the nines - well, dress your face, anyway. You're going to make-up your face so that it is immaculate. Use everything at your disposal. Make sure you include at least 5 cosmetics. Lipstick and eyeshadow are musts. Then go about your business as you want (keep it on for at least 15 minutes - your inner sissy deserves at least that long).

When it's time to remove your makeup - either because you're going out or expecting someone over - you can begin the true assignment.

Clean off your makeup in a normal sink without the benefit of a mirror or make-up remover pads. Use soap and water to get rid of the make-up. Scrub and pat at it until you think it's gone - you've likely removed make-up many times before, so you should be able to gauge when you've been at it long enough. Of course, you may miss some. Perhaps you'll leave a hint of shimmer on your eyelids from left-over eyeshadow. Maybe you'll have slightly racoon-ish eyeliner from no-run eyeliner. But you won't know, because you're not to look in a mirror for the rest of the day.

Others may see your sissy aspirations in the form of make-up still remaining on your faces. While your inner sissy should be emboldened. For as much as she and you know you've been outside with a clearly visible made-up face.


And as always: Safety, first sissy! When you're removing makeup from your eyes it's important not to scrub or rub very hard. You can scratch or irritate your corneas or sclera by rubbing dust, debris or make-up particulates against the eye. This is also true when you're using remover pads or even applying makeup.

They're the centerpiece of your face, sissy - make sure you keep them pristine.