Deep Undercover

A core tenet of espionage: Always have a contingency plan.

Of course, for some sissies, sucking cock is the contingency plan.


(Unrelated to this anachronistic KGB-filled cappie: thanks to all the new people for visiting and leaving comments! I probably spend more time browsing other people's pages than I really should, but often neglect to leave any comments, even if their stuff is awesome. Way to go for not being like me :D )

More and More Patience

Good things come to those who wait. Even if you might not look forward to them at first.

Maybe a bit like this caption :D

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).

Nail Polish Appreciation (Assignment)

I will admit it: I loooove nail polish.

Lots of people have foot fetishes, I have a hand fetish. A well-manicured hand with the perfect color is fantastic. It's another aspect of style that women get to tailor to their wardrobe. Some sissies have sort of mannish nails (but don't worry, some girls have short stubby nails, too). In that case, it's probably time to make sure you're growing your nails out enough that they are longer than they are wide.


Being a sissy is great, and it's time to celebrate the girly benefits for beauty. Tight pants may have become in vogue for women and men. Some men can get by with a slight bit of make-up. With the right form, they can even pass unnoticed wearing a woman's shirt. But bright, shiny, long nails? Only for girls. Men are stuck with the dregs of short, stubby nails with - if they're lucky - black or dark blue nail polish as part of some punk theme.

A lot of sissies are keen on bright red and french manicure (naked + white tips) styles. Those can be great, but I feel like they're a bit old-fashioned (and it's important that sissies keep up to date with fashionable trends). My favorites are actually blues. Maybe it's the irony, maybe it's the fact that light blue used to be a color for girls, but it's always been my favorite (and what guy would wear metallic sky blue nail polish?). Although, pink is close second.

Whatever your favorite color: It's time to show your fingers a bit of appreciation.

Time to pick out your favorite nail polish (or time to get a 'gift' for your 'sister' if you're a bit of a closet sissy).

Now you're going to give yourself an immaculate manicure. Wipe off the brush as it comes out of bottle, dab it at the back of your nail so the polish spreads to your cuticle and then swipe the brush out to the tip. Do it for every nail on both hands. A lot of nail polish looks a bit 'translucent' with just one coat, so make sure they look perfect. Make sure you have amazingly smooth nails with no residue on your cuticles or the skin around your nails. I'm sure you've done this plenty of times before, sissy. 

Now the actual assignment: You need to take a picture of your nails and post it online or share it with someone. 

There's no reason to be afraid, sissy. No one will recognize you by your hands (of course, you can include more in the picture if you want). You can share it with someone you know or anonymous people online (or even with me). If you don't have an actual camera, then it's time to be a bit more daring and use the camera on your phone or a webcam screen capture. If you don't have any of those things, then it's time to take a stroll outside wearing your nail polish; its the 21st century, sissy and you have the internet—there's no reason you shouldn't have a camera.

Show the world your beautiful, feminine nails, sissy!

(Remember sissy: By e-mailing me a picture you are giving me irrevocable consent to display it, so don't be surprised if it shows up here.)

An Early Start

Sometimes a little push in the right direction is all you need.

Even if it takes a bit encouragement, getting started on sissydom early can pay off in the end. So follow the age-old advice: Don't put off until tomorrow what you can do today.

Promoting A Sissy

I find most sissies are always looking forward to a new position.

But is it workplace discrimination if a sissy loves it so much?

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.)