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Caught Crossdressing! Ms. Piper’s Assignment Goes Awry

Get your own humiliating assignment! 800-601-6975

I love to humiliate my pets by requiring them to wear women’s clothes and taunt them about what would happen if they are caught crossdressing.

I never expect them to actually get caught crossdressing, of course, but I can’t be held responsible for dumb bitches that have . . . → Read More: Caught Crossdressing! Ms. Piper’s Assignment Goes Awry

Sissy Humiliation With Ms Christine

Does my laughing make your knees weak? lol…

Let’s Start With That Sissy Clit

My goodness, should we even call it that?  That tiny nub is almost too small to be seen!  Will you even be able to rub it so you can have a squirting sissygasm?  I don’t know, maybe . . . → Read More: Sissy Humiliation With Ms Christine

Ms. Marlena is Conducting Leg Inspections!

All sissies line up for leg checks!

As a sissy, your main impetus is the replication and exaggeration of traditional girliness, femininity, and sexiness. You achieve this with your clothing, accouterments, make up, and behavior, but have you paid special attention to your body hair? I have minimal patience for half measures, so I . . . → Read More: Ms. Marlena is Conducting Leg Inspections!

Ms. Delia’s Sissy Shopping Trip

To The Adult Toy Store

Sissy Shopping Time!

Usually, I send you sissies out to the drugstore, the shoe store, or to the local lingerie store to buy yourself some pretty things.  Of course we add in a little dose of humiliation along the way, now don’t we?  Well, today, I want you . . . → Read More: Ms. Delia’s Sissy Shopping Trip

Bring Out Your Inner Femme with Ms Vivian

 

Hello there, sissy bois and assorted panty sluts. Your MILF Mistress Vivian hopes you’re doing well. I also hope you’re in the mood to get a little bit naughty today because I’ve got an assignment for you all.

What do you say? Humm?

It’s time for you to put your exhibitionist panties . . . → Read More: Bring Out Your Inner Femme with Ms Vivian

Sissy Training from Ms Lauren

When you look in the mirror, what do you see? An overly masculine face with a bit of stubble, I’m sure. In order to reach your full feminine potential, what better way than to arch your eyebrows? Framing your eyes is the perfect, sometimes subtle way to enhance your appearance. Genetic girls . . . → Read More: Sissy Training from Ms Lauren

Sissy Training from Ms Olivia: Bend and Snap!

Don’t you just love the movie Legally Blonde? WHAT? You’ve NEVER seen it? Well. We’ll just have to DO something about that, won’t we?

Today’s assignment… said, in my most serious Mistressy Voice… is to get ALL DRESSED UP… whatever is YOUR level of all dressed up.

. . . → Read More: Sissy Training from Ms Olivia: Bend and Snap!

Sissy Training from Ms Olivia: Thigh High Party!

Do you like thigh highs? Ohhhhh, I know you do! What do you like about your favorite stockings? The texture, the color, the style, lace or no lace on the tops, old fashioned nylons, reinforced heels and toes…. so MANY choices. Today’s assignment is designed to STRETCH your imagination…. and, something ELSE. . . . → Read More: Sissy Training from Ms Olivia: Thigh High Party!

Sissy Training From Ms Olivia: Pantyhose Party!

It’s a PARTY, bois and girls… and what would a party be without party favors and FLAVORS? Since this is a Pantyhose Party, your assignment is to GO SHOPPING !!

Now, there are SO MANY different kinds of pantyhose. Perhaps you already have certain favorites, so what I want you . . . → Read More: Sissy Training From Ms Olivia: Pantyhose Party!

Sissy Training from Olivia

I see you’ve decided on which panties are your favorites and I think you’re right, those will look FANTASTIC on you. Now, let’s get the matching bra… hold out your arms, I’m going to slip it on you. Good, that’s perfect. Look in the mirror.

Oh my dear, you are . . . → Read More: Sissy Training from Olivia