Category: sissy girl

Diana  1-844-332-2639 Ext. 248

I was reminiscing about my first sissy recently. There’s something undeniably seductive about exploring power dynamics in a relationship. For me, stepping into a dominant role with a partner isn’t just about control—it’s about trust, vulnerability, and the intense connection that blooms from those moments. One of the most exhilarating experiences, the first time he wore panties, often makes me smile. There’s nothing hotter than kinky twists on traditional roles.

I won’t lie, watching him surrender his masculinity to me was beyond thrilling. I picked out a silky pair of pink panties, with delicate silk flowers embroidered on the edges. He whimpered as his cock felt the soft fabric for the first time. Continue reading “My First Sissy” →

Girl Talk Confessions

Mama Felicity 1844-332-2693 Ext 270

One of my favorite types of calls is girl talk confessions! I love hearing what you naughty boys do when you’re dressed up as sexy sissies. Some of you are filthy sluts, and your stories leave my jaw dropped!

A few of my lovelies likes to call me while getting dolled up. As they roll up their stockings and clip on their padded bras, they dive into the slutty details that they can’t tell anyone else. I mean, hello, who else but me knows how much of a sissy whore they are? Just the John’s they swallow, I guess.

Continue reading “Girl Talk Confessions” →

Miqala 844-332-2639 ext 447

I need a bitch. Not any little bitch, but my special little bitch. You like the idea, don’t you? But let’s see if you qualify. I am demanding, and I expect a lot. See, a good bitch only thinks of his Mistress. A good bitch is ready to drop anything and everything for my smallest wants.

If I want my house cleaned, you will rush over to do it. You’ll accept being stripped down and put into a cute maid outfit. (I do admit I have a preference for men in cute little French maid outfits.)

Continue reading “Be a Good Little Bitch for Me” →

Babysitting Mila 1-844-332-2639 Ext. 220

One thing about being a cute teen that everyone loves, is that you get a lot of babysitting jobs. Like, a lot. So many little ones to look after, especially since I have nursery experience! And I always make sure to take as many of these little jobs as possible, because I know those little ones are going to love me! They just can’t get enough of the special games Sitter Mila loves to play with them! Even if they pretend to complain, I always know they watch me leave with that dreamy haze in their little eyes, waiting for me to come right back!

Continue reading “Babysitting With Mila” →

Body Envy

Robotic Rita 1844-332-2639 Ext 413

Oh, you have a bad case of body envy! I mean, it reeks. Most men look me over with sexual desire, but the green-eyed monster shines through your gaze. You don’t want to fuck my face or impregnate me. No, you want to be me. It’s obvious; I don’t understand how you’ve managed to hide your secrets from your wife for so long.

Is she just stupid, or does she not care about you at all? All the signs are there. Why can’t she see how badly you want to be a woman?

Continue reading “Body Envy” →

Mercedes 1844-33-CANDY Ext. 423

After a fun afternoon of hanging out with my girlfriends, I return home, finding the house still a fucking mess. I had given you the task to tidy up our apartment while I was gone for a few hours. I should have known that you weren’t capable of following orders too well.

You are sitting in our living room, eyes widened with anxiety, knowing you have failed your task of completely tidying or living space. At this point, you know what’s to come… After I complain about what you haven’t done, I send you to our bedroom to put on the lingerie I had you buy for when you disobey me. “Go to the room and get changed. Come back into the living room when you’re done, you useless scum.”

“Yes, Goddess.”

Continue reading “Punishing My Sissy Husband” →

Zesty Zoey 1-844-332-2639 Ext 403

I love shopping with my sissy.  It’s so fun to find outfits and accessories to turn you into the most perfect feminized sissy you can become.  We’ve spent hours together training you up.  You’ve learned how to be a good little cock sucker.  So, now you’ve earned a reward.  It really does pay off to suck cock like a champion.  You’ve worked really hard to emulate the behaviors of a proper sissy.  Now it’s time to make you look like one.  It’s sissy shopping spree time!  We’ll go to all the best stores and shop together for some sexy little outfits for you to complete your transformation.

Continue reading “Shopping with My Sissy Phone Sex” →

Naughty Naomi 844-332-2639 ext 216

Welcome sissy faggot, it’s time to start your training.  Do you know the best place to properly train a cock sucker like you?  My favorite place to take you to practice is the local glory hole.  Tonight is glory hole training! But first, we have to get you presentable.  Guys aren’t going to want to get their dicks sucked by that. *waving vaguely at you

So, it’s time to femme you up a bit.  Time to do your hair, make up, and to dress you like a proper slut.  I’ll transform you into something men want to stick their dicks into and get off.  Pout those lips sissy, time for that lip gloss so your lips slide smoothly up and down the cocks you suck tonight.

Continue reading “Sissy Faggot Glory Hole Training with Miss Naomi” →

Zesty Zoey 1-844-332-2639 Ext 403

Welcome to Zoey’s University of Femininity!  Things are going well with the development of my training program.  My first set of students has gotten off to a great start.    From sissies to fembois, no one is turned away.  If you’re willing to put in the time and effort to learning how to become your best feminine self, there’s a place for you here.  So many classes to reach your feminizing goals.  I know you’re going to find exactly what you need and are looking for here.  Classes are offered in fashion, deportment, and even improving any and all sexual activities.

Continue reading “Zoey’s University of Femininity” →

Mommy's New Office Secretary

Mama Felicity 1844-332-2693 Ext 270

Awe shucks! My secretary quit on me at the last minute! I have an incredibly important board meeting with the founding female committee members today, and I will need a second pair of hands to take notes and keep everyone on task! As we all know, finding good help is near impossible these days, so I’m going to have to turn you, my little submissive loser, into my new office (sissy) secretary!

I’ll dress you in the whole nine: thick, suntan nude pantyhose, a pencil skirt, heels, of course, and a button-up blouse. A blonde wig so no one knows who you are and, of course, lots of makeup to define your feminine features. Hurry and get ready. You don’t want to be the reason we’re late to the meeting and then have to explain to the other ladies, do you?

Continue reading “Mommy’s New Office Secretary” →