Sissy Training Roulette 1

I thought it only fitting to begin with the image that convinced me to create this blog in the first place.

(First posted on NewFapChan)

For the uninitiated this is a "fap roulette." A fap roulette is basically a set of instructions for masturbation (i.e. fapping) organized according to assigned numbers. This number can be from a random number generator or - the origin of fap roulettes - a chan board's post number.

For example:
If your post number were 30012203927 (or your random number generator created 3927), your W = 3, X = 9, Y = 2 and Z = 7. Or more detailed.

• W3 - Always sit to pee. Make sure you wipe your clitty!
• X9 - Power of 3! Do (3) [that is wear a bra that matches your panties as well as a skirt, heels and pantyhose], (6) [wearing the sluttiest makeup you can manage] and a consecutive Y minutes [Y in this example is 2, so 2 minutes] of tucking your clitty before you can move on to Y.
• Y2 - Small fuck. 1 finger in ass while you fap.
• Z7 - Cum in your panties and sleep in them.

Early fap roulettes focused on the porn you were to watch and what you did before and during fapping. Soon "cum lover" fap roulettes appeared, describing what you should do with your cum. Crossdressing, BSDM, and other roulette types soon appeared. And that's how we got here.


Of course, if you don't have a RNG or a chan board handy there's always online generators like random.org. Or you could flip 14 quarters and learn binary.


Let me know how you roll and how your W works out! Or your XYZ if you're feeling adventurous.


Since so many sissies (aspiring and full-fledged) seem to stop by this roulette: there's other great fap and sissification materials spread throughout the site, but if you ended up here you'd probably like the second Sissy Training Roulette.

Read more »

Online Sissy Quizzes

Find out what sort of sissy you are. There's a wide variety to aspire to! Do you just want to be a pretty princess at home, dressing to express your femininity and innocence? Do you aspire to become a beautiful girl in both thought and body, improving yourself for yourself? Do you dream of being submissive and serving, sucking cock and drinking creamy cum? Do you see yourself as a feminized tool of others, a toy for the amusement of your betters? Or even something else!?

Or maybe you're a bit of an indecisive sissy, switching from one role to the next. That's okay too - as long as you're the girl you deserve to be. Here are a few quizzes that might help you decide.

Sissy Quizzes

Enlighten your inner sissy. Just what is your girly purpose? Of course, if you just like expressing your feminine side you might be best off with a few fashion quizzes or femininity quizzes.

What kind of sissy are you?

Decent variations in questions (at least in relation to sissydom), but the results are somewhat limited. I am a pantyslut.


Are you a Sissy Slut?

Exotic and arousing. Find out if you feel at home dressed up or going down, basically. Unfortunately it's not automated, but some of the best sissy quizzes aren't. I've got about 41.


Your Feminization Quotient

A fairly old standby for finding out how far you've gone as a sissy. I am at a lowly 49. Scoring is available on the general test page.


Fellatio Fanatic Test

Fairly in-depth with a variety of questions. OKCupid/Hello Quizzy used to have an excellent 'cocksucking slut test,' but unfortunately it disappeared.

Gender/Sex Quizzes

Looking for something a bit more mundane? Is your personality womanly without necessarily being too sissified? These quizzes honestly attempt to determine what sex you are.

The Spark Gender Quiz
(unfortunately requires a login)

Bases its analysis on pattern recognition, gender roles, perceptions, consensus and some other factors. I remember taking it years ago and getting a "0% certain you are a woman." Now I get a "24% certain you are a woman." I recommend answering honestly and seeing what you get.


BBC's Sex ID Quiz

Uses an assortment of biology and psychology to determine if your brain exhibits more masculine or feminine thought patterns. Fittingly, I guess, I ended up right in the middle with a 0. Apparently I've very good at rotating 3D shapes in my head though, so bonus!).


Should you be male or female?

Asks questions that aren't very stereotypical to guess at your sex. I am apparently either male or female.


The famed COGIATI

The COGIATI was developed as a means of helping inform people if they have transsexual tendencies. It provides an interesting view of your state of mind, but is only applicable for MTF transsexualism. I get a 65, which puts me in the middle androgynous category leaning towards feminity (Well, I did say I was a sissy and a tomboy!). But don't take the results too seriously, the test is only a "prototype" and not an accepted psychological profiling exam. There's also the longer (and attempting to be more psychologically applicable) SAGE.

Feel free to share any quizzes you really like. Like if you are a slut or even a cumslut.

Read more »

Sissy Training Roulette 2

As promised, here is another fap roulette. Hopefully the heavier focus on feminization and the design change is an improvement for most people.

(Check the first fap roulette posting if you need more information on how they work)

If you are unfamiliar with dubs, trips and quads: these are when the last numbers of your post/roll are the same (2 of the same, 3 of the same, and 4 of the same, respectively). E.g. if your post number is 102945999 then you have trips - 999.


For Easy Mode: Instead of having a W and X, if Z is even do your W for a week, if Z is odd do your X for a week.


Happy rolling, sissies! Just make sure you follow through...

Read more »

Regular Fap Roulette

So it was my birthday and I figured I'd follow the German tradition of giving out small gifts to colleagues. Of course, this isn't very sissy related (unless you roll just right). So I'll get something more sissy-appropriate to post today for you girls, too.

Since 4chan seems to be overflowing with fap roulettes that claim to be the "ultimate" fap roulette, but really only have 1 or 2 similar options. I decided to make one a bit more versatile.

Now it's actually a gamble for what you'll end up with.

Do you remember your inner girl's birthday? Maybe it's time you did; she deserves a special something, too!

Read more »

Rolling for Femininity (Game)

Alea iacta esto! Not up on your Latin (or English idioms)? "The die has been cast" - what Julius Caesar supposedly said as he crossed the Rubicon and invaded Rome to seize power. That's a bit dramatic, but today you'll get to seize a bit more femininity for yourself.

Find a six-sided die. Now you get to do some simple rolling for a task that any sissy can complete at home. Iacta cubum (roll your die, sissy!).

Put on a simple dress (or just panties if you don't have a dress). Relax on a couch or bed - laying on your side with your knees together. Watch the girliest thing you have available - this could be Oxygen or Lifetime if you have cable, a cute anime on DVD or a romantic comedy (Hulu has some stuff if you have no other ideas). Enjoy for at least one and a half hours.

Perform some simple nail care; file and buff your fingernails. You're aiming for a nice elongated oval shape. Nails don't always cooperate and you might have to content yourself with just well-rounded edges. Trim your toenails as well (make sure there's no gross dirt beneath them). If you have nail polish put on at least one coat. You don't need to keep it on, but maybe you should, sissy.

Wet down your groin area with warm water. Wash it thoroughly (take a shower if it's easier for you). Carefully shave everything beneath your clitty. If you want to keep a bush make sure you trim it properly (a simple triangle or cute heart of short 1cm long hair would be pretty). You don't need to shave your legs too, but hopefully you're already being a good girl and keeping them smooth.

Practice improving your penwomanship for 30 minutes. Look here if you need some inspiration. Sign your (female!) name until you can do it comfortably. Try writing a short autobiography (surely something in your life must have led you to sissydom!). I'm sure you can find a pretty pink pencil (well, I'm sure you can find one at home where the eraser is pink, anyway) and some paper.

Practice speaking with a female voice for 30 minutes. Try starting here if you're lost. As an alternative quick method you can try: Breathe deeply, gargle with your voice until it's as low as you can go without having it crack or skip, repeat "Wicked Witch of the West" thirty or more times while trying to speak like an old man or old lady. Hold a pillow or towel over your face if volume is a concern.

Draw a heart on your body with a sharpie. Write "SISSY" inside of it. The letters should be easily legible and at least 1cm tall. Draw the heart first and then write; if it ends up too small fill in the heart and try again. Your first try can be in red ink, but each subsequent try must be black or blue ink. Write anywhere but the soles of your feet.

Most of the visitors are from the US and use imperial standards. You don't need to run off to find a metric ruler; a half-inch will do fine, ladies.



Actually Julius Ceasar most likely said, "anerriphtho kybos" (in Greek), but understanding Latin and classical Greek are not necessary for you to become the best girl you can be. Unless you aspire to be a domina in ancient Rome.

Read more »

Truth or Dare

We certainly can't play spin the bottle or strip/dress-up poker, but we can play Truth or Dare! So which will it be, girl? Truth or dare?

Truth: Why do you love dressing like a girl?

Tell the truth - you love dressing up like a woman. You love panties and dresses and skirts. So, why?

Some sissies are 'forced,' most sissies do it voluntarily. It could be from the feel of soft, gentle fabrics like silk and lace that men's clothing just don't have. Maybe you're just indulging your own autogynephilia. You could have a master or mistress you're just eager to please who loves you in frilly pink. Only you can know for sure, and now you can tell someone else.

It wouldn't be much of a truth if you kept it to yourself; post a short explanation somewhere with a little permanence - something that will be around for at least a day. You can do it anonymously, just write it somewhere. "I love dressing like a girl because..." You can even post it here if you can't find chan board or forum or website that suits you.

Dare: Buy some tampons

Go to a convenience store or department store and purchase a box of tampons for yourself. Oh, but it's not that simple, sissy. You must wear some makeup, you cannot use a bag, and if anyone asks you must tell them that they are for you.

You don't need to wear heavy makeup. In fact, it can be barely visible if you want. But you must wear some eyeshadow and some lipstick - however nude or thin they may be applied. If you're extra daring you could try to buy them dressed completely en femme. If you're offered a bag you'll politely refuse. If the clerk asks anything about them ("Errands, huh?" or "Wife had an emergency?"), you'll tell him, "These tampons are for me."

When you get home use one of your tampons (hopefully you bought size-appropriate tampons). You can leave it in for a few hours or take it out right away. Of course, if someone comes over and asks about them you'll have to tell them that they are for you.


Boring (and potentially gross), but informative safety information: Some sissies (and girls) have concerns about toxic shock syndrome from tampons. TSS stems from the build of toxins released by bacteria where it can enter the bloodstream (not necessarily the tampon material, but more absorbent tampons means more moisture). The bacteria can grow in warm, moist areas (which is why it's better to store your tampons in a hall medicine cabinet instead of a bathroom); TSS in relation to tampons happens from the collection of menstrual fluid and the heat of the human body. You can decrease your already minimal risk by washing and drying your hands before inserting, using less absorbent tampons (although there really shouldn't be much fluid to absorb from your rectum, sissy - I told you it could be gross), and changing out your tampons frequently.

Hypochondriac sissies may substitute a buttplug for their tampon.

Read more »

Truth or Dare 2

Ready to brave the waters of another bout of Truth or Dare, sissy? Some girls may still be a bit behind and may want to check in on the first round from last month.

Truth: Have you ever gone outside fully dressed like a girl?

Many sissies dress in the safety and privacy of their own homes. There are even closet crossdressers afraid of venturing outside their bedrooms with any hint of femininity about them. But have you ever braved the great outside with makeup and feminine clothing caressing your curves? How did it feel? Wonderful, exhilirating, heart-stopping? Or maybe you've gone out all the time and it's become common for you to turn heads as people stare at your beautiful figure?

Your inner girl certainly deserves to feel the wind whipping through her hair (or rustling underneath her skirt), so hopefully you've gone outside dressed to the hilt (or garter, as the case may be). If you've never gone out is it simple fear? There's no reason to be a cowardly sissy - women are strong, proud and courageous and you should be, too. Think about how you could get out and about like a girl - even if it's slipping out through the garage ...in your car...at night.

Dare: I dare you to step outside in daylight wearing a skirt.

Skirts are quintessential feminine articles. Men may wear kilts, but only sissies and women wear skirts. And only real women and devoted girls-to-be go outside wearing skirts.

You don't need makeup. You don't need oodles of time. But the next time it's daylight and you've got free time I dare you to go outside wearing a (visible!) skirt. Not covered over with pants or a blanket. A real, honest-to-sissydom skirt. Just stay outside for at least a minute. Sit. While away some time dreaming of your future aspirations as a sissy.

The first step is always hardest, so after you've gone with a skirt it may be the perfect time to go a bit further with something else. Maybe you could go shopping with a well made-up feminine face...



Got out there and get 'em, girl!

Read more »

Girl's Day Out (Game)

Today: a game that combines two perfect activities for you ladies. Shopping has been feminine past time for years, and more recently it has even become a hobby. And of course, it wouldn't be much of a game if we didn't help feminize you and your lifestyle just a little bit.

For you closeted sissies this will be slightly more difficult, but you'll get the secret satisfaction that your room (or apartment or house) is slowly filling with girly things for your sissy side.


You're going to buy feminine objects that you'll use or wear or see every day to help remind you of how much of a sissy you are. The most feminine colors are pastels (very light colors), purple, pink, and lavender. Turquoise and white are also generally feminine colors, but they're far too easy for you to pretend they don't belong to your sissy side.

Anything smaller than a fist counts as one. Anything bigger is two. Only non-food, non-perishable items count (so no box of pink wafer cookies). Sets of things only count once. If it's feminine clothing it counts double (and white, turquoise and black are also acceptable). Make-up also counts double.

The pink-purple spectrum counts double as well.

And this is a shopping trip sissy. That means no online shopping. You're visiting actual, physical, brick-and-mortar (or poured concrete...whatever the case may be) stores. Drive, walk, skip, prance - it's up to you, so long as you're there in person. Your final haul must include items from at least 3 stores.

Your goal is 10 points of femininity.

This could be: a pack of pink mechanical pencils (2 - pink and small); a purple clothing hamper (4 - purple and large); a set of pastel barrettes (1 - pastel and small); a pair of pink panties (4 - small and feminine clothing and pink).

Or simply follow this sissies excellent outfit guide and you'll be there in no time:

Next time you need to go out for clothes, household supplies or decorations play the game and you'll be surrounded by feminine things in no time. The sissy you will love it.

Read more »

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!

Read more »

Super Deepthroat (Game)

In the days of yore when I had to get by on using makeup websites' makeover applications to satiate my desires, I did a lot of searching for games, quizzes and various sissy-related things. Based on the number of people that stumble by with roulette-related searches, it seems I'm not alone.

But today I'd like to point out one of my favorite (relatively recent) finds: SuperDeepthroat. Ostensibly one could argue that it's about objectifying women and being a deepthroating simulator. But for an imaginative sissy it's just another avenue for practicing her cocksucking. Perhaps it would be better as SissyDeepthroat.

Since you can do your sissy's make-up and pick her clothes and even her skin and outfit colors you can ostensibly build a digital version of your emerging sissy form. She just happens to start on her knees with someone's hands on the back of her head...

Read more »

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).

Read more »

Truth or Dare 4

Ready to open a freshly wrapped truth or dare?

We are approaching the core of the holiday season, and in the spirit of gift giving and receiving, it's time to explore what your sissy self has always wanted as a gift!

Truth: Which of your female friends/siblings gifts did you really want?

Many sizes would love to receive some smooth, lacy lingerie for Christmas today, but as children many sissies also yearned for the gifts that their female friends and relatives received. Either too secretive or confused to actively ask for such gifts, they had a hidden jealousy for the unwrapped gifts of their female peers.

I was occasionally "forced" to play house and Barbies with my sisters. But dressing and having imaginary everyday adventures was certainly fun, and I was never one to balk at the idea (a great, more modern analogue is the Sims - which is why it's a frequent favorite among girl gamers). As one of the youngest instances of preferring one of my sister's gifts, I remember a sleek, pink convertible being unwrapped and thinking how cool it would be to have my neatly-dressed Skipper cruising around.

So what was your most desired treasure, sissy? A Barbie or a cosmetics case? Or maybe even something a bit more tomboyish like a Mia Hamm jersey? Or just something as simple as the clothes your sister got?

Of course, you may have become a sissy a bit later, in which case you certainly have more ...adult gifts to fill your sissy wishlist.

Dare: I dare you to gift your inner sissy something she's always wanted.

How often has your inner sissy been able to unwrap a present specifically addressed to her? Have you completely embraced your feminine side and opened a package addressed to you with your sissy name?

Well if you haven't, now's the time.

What you want as a sissy can vary spectacularly. For very juvenile sissies, it may be something like a Barbie or a jewelry making kit. Most sissies - even if they were interested in their sisters' or cousins' gifts - still didn't receive much in the way of girly gifts and accessories as a kid. It may be the perfect opportunity to gift your inner sissy a childhood memory with a present she wanted as a child.

Of course, many sissies are grown up and prefer more adult gifts. Perhaps your inner sissy is a bit of a slut or nympho. She may benefit from a dildo or vibe to help curb some of that arousal (of course, knowing many sissies this may exacerbate the situation, but she'll certainly love it). Maybe she's always wanted (but could never work up the courage for) a dress or exotic outfit. Or maybe even lingerie. She's you, so only you can know what she truly wants for Christmas.

And then you'll wrap it and address it specifically to her. Feel free to put it under your tree (of course, some gifts are best in private :D ). Then on Christmas Day (or at some other point if you're ordering online or aren't Christmas-inclined), let your inner sissy dress to the nines and open the gift she's always wanted!


So a very Happy Holidays to you sissies and may all your wishes come true!
(even if it takes a little time)

Read more »