RSS: Oral Aptitude

This summary is not available. Please click here to view the post.

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.

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.

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.

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.

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.

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.

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.




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.

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.

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.

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.

Preparing for Regina

I'll be gone for a while in the next couple weeks, but I've lined up a special surprise for you sissies for when I'm gone. Hopefully you'll give her your undivided attention.


(Regina uses beautiful Scarlett Faye as her avatar)

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.

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

Open for Regina

I hope you sissies have kept busy with your tanning. There's no reason to squander your summer, sissy - get out there and take the steps to being a better sissy.

That's obviously  long-term sissy project, but there's certainly some shorter term tasks to help you on your way.


Yes, I know, many of you sissies don't actually have petite feet - It doesn't matter what size they physically are, it's how you work them and treat them.

And don't you fucking dare tell me you don't even have clear nail polish, sissy. There are kinds that even men use to strengthen weak nails; tell the cashier you're working on an art project if you want to play up the charade that you're not a complete and utter sissy.