Friday, September 30, 2011

Essence (Assignment)

Many sissies get hung up on the kink and excitement of exotic feminine wear. But sometimes the common, normal, everyday pair of panties becomes too common, normal and everyday.

So today you have a special assignment to reconnect you with the garment that most often convinces sissies to embrace their feminine side and leave the woes of their masculinity behind: panties.

Go to a department store and find the women's wear section. Look for all the different kinds of underwear they have there. Make sure you look around all over. If you're not sure you've seen everything ask a store employee for assistance.

Once you've seen everything mull over which pair you would want to buy. Don't just pick the first pair you see and run off. Really think, sissy. Which pair of sensuous panties cries out to you? Are you a thong kind of gal? Basic cotton - maybe with a bow in front? Or are you really racy enough that you would want to wear silky, lacy ruffled panties all day?

Find the pair that speaks to you the most. You don't have to buy them (sissies shopping for clothes tend to be a bit short on cash), but maybe you should. They could be your bottom's next bosom buddy. And of course, there may be a matching bra to be your bosom's bosom buddy, too.

And if any clerk or employee asks, you should be a good, honest girl and tell them the truth: that you're looking for the best pair of panties for a very special person.

Thursday, September 29, 2011

No Return

Sissies come in many forms, and there are many ways to tell if they've become true and complete sissies with no hope and no desire to relapse into pretenses of masculinity. This is probably the most prominent and most fun.

You should beam with pride just like this sissy if you've ever had the exquisite experience of earning your own sissy certification.

Wednesday, September 28, 2011

Just One More.Drink

...of delicious man juice. While dressed to the garter as a beautiful sissy, of course.

A cautionary tale of being wary what you listen to, or an up-beat tale of what wonderful things can happen to you? I think your inner sissy may have the answer for you...

Tuesday, September 27, 2011

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.

Monday, September 26, 2011

Become a Princess

Practicing every day will feminize you faster - especially if you end up subconsciously feminizing yourself through daily routine.

I marvel at this sissy. She is beautiful.

(And this caption is inspired by Little Miss Squidgy - Panties)

Sunday, September 25, 2011

Trapped by a Trap

I think this is the most text heavy picture yet. And with good reason - seduction isn't easy!

And if anyone's wondering about sissification and feminization: I consider sissification more externally sexualized and feminization more personal. If you want to suck cocks you want to be a sissy. If you want to sit knees together and intonate like a woman you want to be feminine. Of course, they're not mutually exclusive, you may want to suck a cock with a beautifully made up face and perfect feminine mannerisms, with only an oversized clitty hinting at your past.

But that's how my labels work, anyway.

Friday, September 23, 2011

Explicit Lyrics

When has that ever stopped a sissy?

"Suck cock. Wear skirts and dresses. Let men fuck your mouth and ass..." It could all be pretty explicit, if she could hear it...

Thursday, September 22, 2011

Colors of Your Bow

Pink isn't necessarily the girliest color, but in all of the internet it's certainly the sissiest color. Of course, if you were forced to wear pink you wouldn't have much say in the matter, would you sissy?

I know I haven't acknowledged it lately, but every reaction helps. I know the earlier roulettes are by far the most popular feature of the site and there hasn't been a new one in a while. Don't despair with your fapping and sissification, more will come!

Wednesday, September 21, 2011

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 your 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!

Tuesday, September 20, 2011


Most sissies are more attracted to women than to men. But this doesn't mean many sissies don't have fantasies about sucking cock or taking dick in every hole they have - they just find women as a whole attractive.

(Images from the beauties at Club Crossdressera)

But you'll never be able to proove to everyone that you're not a cock-crazed sissy slut. Besides - in addition to other things - you're probably one anyway. Right, sissy?

Monday, September 19, 2011

Letter Off

Sissy names are a bit strange, since they come about in interesting ways. Many horny sissies take names from strippers and porn stars (I feel Candy falls into this group). Others take a female name that they like the sound of. And others take or are given a name that's a close analogue to their old male name.

So today we've got lucky Andrea, who only needs to change one single letter.

Sunday, September 18, 2011

Living the Joke

Well, not everyone can have a sister, but some are nicer to their sissies than others.

The only reason I include the Natalie's Cappies watermark is so aspiring sissies might be able to find the rest of the collection at this site. Hopefully that's been useful to someone.

Friday, September 16, 2011

Dude Eats Like a Lady (Assignment)

We've gone over exercise with a previous running assignment (hopefully you've taken up some sort of aerobic activity on a regular basis), but the obverse side of the fitness coin is diet.

Rather than try to influence the variety of things you could eat we'll focus on something more immediately controllable and measurable. Women take smaller bites than men (and so should sissies!). This leads to eating slower, which leads to recognizing that you're full before you overeat.

Actual food content is important too, but in this simple assignment you will do a simple task: eat daintily like a lady for a whole day. Only fill the tip of your fork and spoon with food - not the whole thing. Never have a mouthful of anything. Sips and nibbles for the whole day!

Have the complete and utter comportment of a lady when you eat. No elbows on the table, no chewing with your mouth open and all the other perfect manners you would expect from a well-behaved lady.

And since there just aren't many pictures of sissies eating, I'll leave you ladies with this picture of the figure you could work towards, instead:

Thursday, September 15, 2011

Model Sissy

I've returned with a more hectic schedule than when I left, but I'll try to keep updates consistent (but no promises!). Apparently while I was gone the roulettes exploded in popularity.

A great thanks to Regina for assisting me - how could I hold her time mix-up against her if she's doing work pro bono. Much love for you, Regina (and also for the blossoming audience - in more ways than one).

Wednesday, September 14, 2011

RSS: Self Discovery

This is, of course, Natalie's site. My time here is only fleeting (and unfortunately - for some of you sissies that are a bit undertrained - shorter than intended).

Time: 15 minutes
What you will need: your improved sissy self

Sissies interested in improving themselves (which should be all of them) should follow my last bit of advice.

I'm sure at some point in the future Natalie will be away for an extended period - I'd be only to happy to improve you sissies further. Only so much can be accomplished in a few days.

You had better keep up on your feminization and embracing your girlhood. Don't fucking throw out any of your feminine things on a whim of guilt or fear of losing your masculinity - it's already gone. You are a sissy. That ever-increasing femininity is part of you and it will always be part of you.

Until then, sissies.

- <3 Regina

Tuesday, September 13, 2011

RSS: Discovery

Sissies often only embrace their femininity in superficial ways. Wearing make-up and girly clothes without ever daring to delve deeper. Well today you're going to go a bit deeper.

Time: 30 minutes
What you will need: your lovely sissy self.

Sissies may take Sissy Acceptance if they're still not willing to accept their deeper femininity.

Concerned sissies may use lube (even petroleum jelly will work for such a simple act). But either way you are going to go as deep as you can. I know some sissies are already big anal sluts, and for you completing today's lesson should be easy.

Today you can cum, but you will follow my instructions: you will not jerk your clit. You can cum from anal stimulation or rubbing your clit - or even humping. But you will not wrap your hand or fingers around the tip of your clit or stick your clit in any toys. Things go inside of sissies; sissies do not go inside of things.

- <3 Regina

Monday, September 12, 2011

RSS: Memories

Many sissies have only a half-defined being due to missing out on precious development of their femininity when they were younger. Today we'll help you overcome that shortcoming.

Time: 1 hour (encompassing a life-time)
What you will need: your inner sissy child

This lesson is mandatory.

Sissies exceptionally proud of their work can email it to me (or post it in acomment) and I may append it to this post for other sissies to learn from.

And don't even think about asking for any sort of permission. Your mind should be flush with all sorts of new memories, and we don't want you to ruin that with something as selfish as your weak masculine side's cravings for pleasure.

- <3 Regina

Sunday, September 11, 2011

RSS: Redux

Many women do not become aroused as easily as men. Even the path to an orgasm can vary quite wildly. While most men prefer moving video and sound, women usually enjoy all manner of sensory stimulation - even including scent and taste. It can be frustrating to be a woman, because a slight loss in concentration may completely cool off your sexual appetite, but when you do cum it is a full body experience that affects you much longer than a simple male spurt.

Time: 24 hours
What you will need: your sissy clit

This lesson is mandatory...but I wouldn't think you'd skip the chance to work your clit anyway, you whore.

I want you to cum as many times as possible in the next 24 hours. If you lost your cum dumpster before then you will make a new, smaller one. There is one caveat: I don't want you to use any overt audio or visual pornography (no videos, no hypnosis audio, not even pictures with or without captions).

I'm not going to give you any material to use, either.

Most women do not get off on videos and many don't even use images. Women enjoy written erotica and their own fantasies. Lay in your bed - massage your body. Gently knead your breasts, run your fingertips down the inside of your thighs. Give yourself a little foreplay before you dive right to your clit or ass. Light candles or incense or find some other feminine scent to fill your room. Use your imagination to conjure up the fantasies you wish to see. Imagine it is you that is getting a throbbing cock driven deep inside of you. Imagine it is you getting goopy cum splashed all over your face.

If you're close to your own girlhood you might be able to rub some cum out of your clit without much effort. If you can't I'll obviously need to be tougher on you because you've still got a pathetic excuse for masculinity holding you back from being a good sissy.

And for the sake of your femininity think of yourself with a feminine name. I'm sorry "Doug," but in good faith I cannot wholly accept your apology until you embrace a feminine name like every sissy should. Being a sissy is your destiny, so perhaps you should be Destiny.

- <3 Regina

Saturday, September 10, 2011

RSS: Oral Aptitude

Your mantra includes aspects of submissiveness and service. One of your greatest accomplishments as a sissy may be sucking a cock - showcasing your passion for both of those aspects of your being at once.

Time: 30 minutes
What you will need: a dildo or dildo equivalent (or a real cock you can suck)

You may alternatively choose to undertake Physical Education or Sissy Acceptance.

If you can practice this without scraping your teeth on the shaft, and while constantly in motion sucking and bobbing and slurping then you may cum. But only as long as you promise to dip your dildo in that cum and suck it clean for another 5 minutes. Don't you fucking dare cum into a tissue or refuse to suck that cock afterwards, sissy.

Depending on how good at cocksucking you become you may make guys cum in mere minutes, but a filthy sissy like you will probably want to serve a line of cocks, so it's best to prepare your whore mouth early.

- <3 Regina

Friday, September 9, 2011

RSS: Women's Studies

Just like you picked a hero when you were a kid, today you will pick a heroine to inspire your inner sissy.

Time: 10 minutes
What you will need: your intelligent sissy self.

You may alternatively choose to undertake Physical Education or Sissy Acceptance.

You can certainly pick any other woman that appeals to you.

Of course you cannot cum. That would be incredibly disrespectful to your female betters.

- <3 Regina

Thursday, September 8, 2011

RSS: Physical Education

Hopefully you're getting more in-tune with your sissy self. Today we're going to improve your form and sissy harmony.

Time: 20-30 minutes
What you will need: a bra; panties; balloons (or durable breast forms).

If you do not have these materials you must retake Sissy Acceptance 101; otherwise this lesson is mandatory.

For you sissies unfamiliar with a star jump: it is a Jumping Jack.

You should be honored to be able to mimic moving like a woman a bit more closely. Many women also enjoy running, calisthenics and other aerobic activities; I'd hope to get you into swimming in a bikini by the end of classes, but unfortunately the training period is far too short to directly include such a lesson.

- <3 Regina

Wednesday, September 7, 2011

RSS: Culinary Arts

Cooking has been a stereotypical activity for women for years. Today you're going to enter into that foray with a twist. You're going to learn how to make fake cum that looks realistic with two simple ingredients.

Time: 15 minutes
What you will need: flour, water, a saucepan, a stove top

Sissies not interested in culinary arts may retake any of the previous lessons.

Good girls will notice that the flavor is not right. Every load of cum tastes a little different, but you may try to correct this with a few drops of lemmon juice or other flavoring, but nothing will really compete with the real thing.

I would expect sissies who lost or misused their cum dumpsters to jump at this opportunity to partially make up for their misdeeds.

If a sissy gives herself a bukkake and photographs herself she may cum before she cleans up. As a special permission, sissies that also email a picture to their mistress may cum again. Otherwise you have not done enough to warrant such a reward, sissy; do not even fucking touch your clit.

- <3 Regina

Tuesday, September 6, 2011

RSS: Gymnastics

Gymnastics has also become a popular feminine sport in the last few years. Your acrobatics will be a bit different though.

Time: 15 minutes
What you will need: your limber sissy self

Sissies not interested in Gymnastics may retake Sissy Acceptance 101.

Why did I make you wait a painful 3 days, sissy? Because your dwindling, pathetic male body will produce the largest load of cum for you after 3 days. Any more and the amount you get will stay the same.

You can only wank for 3 minutes, sissy. Not a fucking second more. Use a countdown timer if you have to. Of course, if you failed to cum it is your own fault. If you deserved to cum you would easily be able to get your clit hard after all that.

- <3 Regina

Monday, September 5, 2011

RSS: Exotic Culture

Today you will make use of your cum dumpster. And you have a choice - what a beautiful day to be a sissy.

Time: 20 minutes
What you will need: your delectable sissy self.

This lesson is mandatory. I'm already giving you a choice, which is more than many sissies deserve.

If for some reason you don't have your cum dumpster you are going to spank yourself hard until you cannot sit. And then are going to sit and write out by hand "I am a sissy. I am sorry I lost my cum dumpster." You will write it 100 times in your best handwriting, numbering each one. If you are truly sorry you will also write out a heartfelt apology and send it to reginathegoddess @

Option 1

Option 2

If I had my way I would force you sissies to gulp that cum down. I know how much sissies love being cum-guzzling seed receptacles. But Natalie asked me to be a bit lenient, so now you have a choice. Drink that cum or wear that cum.

- <3 Regina

Sunday, September 4, 2011

RSS: Sissy Acceptance 101

Hopefully you've embraced your mantra. Today we're going to help you accept that you really are a complete sissy.

Time: 10-40 minutes
What you will need: your sweet sissy self.

This lesson is mandatory.

All those pretensions that you are really a boy will be gone by the time I am finished with you, sissy.

- <3 Regina

Saturday, September 3, 2011

Regina's Sissy School: RSS Orientation

And here you are my sissies!

You may be a bit lost at first, but that's why we have orientation for you.

Time: 5 minutes
What you will need: your pretty sissy self.

This lesson is orientation and is therefore mandatory.

The sissy mantra will cycle through your mind. Memorize it, cherish it, embody it.

- <3 Regina

No Longer a Man

I had a slight scheduling mix-up with Natalie, so I'll post the first day of schooling today after this fittingly-titled post she had left. For all of you good little sissies who kept up with your cum dumpsters despite the delay I am so very proud of you!

- <3 Regina

I'm usually not a fan of chastity cages and cuckolding, but for some reason I love the look of this caged clitty between too stockinged legs. An obvious (and beautiful) sissy if one ever existed.

Speaking of cages, tomorrow Regina takes over for a few days. I'm almost certain she'd put every sissy in a cage if she met them in person.