A surprise was supposed to be waiting for you at Mistress Michelle's house, but you certainly weren't expecting this. Who knew she loved the idea of sissification?
 
Life's too short to not do what I want, which means that my desire to see you as a sissy is coming to reality. Better still, it's happening today. Don't play games with me you little bitch. We both know you're keen to be treated like a woman so don't deny it for a second.
 
Let's get you into this lingerie. Yeah, as I suspected - you're not the cutest girl around, but I wouldn't be surprised if we went out to a bar and some dude with beer goggles would want to pick you up. As far as first time sissy boys go, you're one of the better ones around.
 
- Michelle Lacy
 

 
It has come to Ashley's attention that you want to go out bar hopping with her one night. She's decided that's only happening if you get dressed up as a woman.
 
You're a dude, you realize that, yeah? Well, you know what, I might actually be able to help you out and become the type of person I'd go out with. Here, take this cute pink bra with flowers on it and try it on. Oh my, that's quite the feminine appeal you have! I didn't realize what a sissy you were.
 
Now before we go out, I need to know that you're going to be able to do the most feminine things. How about you get your mouth around this strapon and show me how good you are at sucking dick? That's a good girl. You've got quite a mouth on you and know a thing or two about getting a dude's junk hard.
 
- Ashley Graham
 

 
Jolene is your mistress and she's about to tell you what happened today with your credit card and her little shopping spree. Go and listen up: she got you a few things.
 
Heya. So yeah, I went shopping today with your card and managed to get us a few things to spice up our bedroom experience. For instance, take a look at this black dress. It was $150 - I think it's a bargain! Oh, these heels as well. Do you think they're cute?
 
So the dinner we're going to tonight? Yeah, well I think it's in our best interests if we show everyone at your company who the real you is. That means that you're going to wear the dress and heels. Believe me, once I'm done dressing you up and making you look perfect, everyone at your company is going to fall in love with sissy you.
 
- Jolene