Lela Beryl wants to help her kinky slave get some hunks so she is going to doll him up in a pretty outfit and some very high heels. There is nothing this mistress would enjoy more than sissifying a horny dude.
 
Today I am going to teach you how to dress as a woman since clearly, makeup is not enough. By the end of this, you are going to be the prettiest princess. First and foremost you will need to go shopping because you will need to have a closet that resembles mine. And don’t forget to stock up on shoes. For today, I will choose these sparkly high heels since you need to learn how to walk in them.
 
Because you are a man, I have selected a push-up bra for you. I want to see you in these high shoes first since I think it will be very fun to see you put the rest of your clothes while wearing them. Get your balance, and don’t fall off your new heels. Let’s get your skirt on and this cute top so you can seduce men and play with their throbbing penises, just like you always wanted.
 
– Lela Beryl
 

 
Sarah Gregory finds it funny that you came to her because you thought that she would be totally accepting of your crossdressing fantasy. Little did you know, her idea of how to sissify is far beyond your wildest dreams.
 
Look at you, standing before me without a single shred of clothing on. How would anyone know that you were woman if you don’t dress the part? It’s not as if your ugly male body is going to have any shot of being mistaken for a lady’s, so do yourself a favor and put on these bra and panties.
 
Once I have you all dressed up in a perfect matching underwear set, I’m going to bend you over and start to spank your little girly ass as hard as I can, making it glow as brightly as I can make it glow. You are going to be such an obedient and understanding sissy, aren’t you? Because deep down inside, you know that to become the type of whore you want to be, following my instructions is the only way to get there.
 
– Sarah Gregory
 

 
Mistress Selena got her sissy friend a whole bunch of super cute lingerie in order to dress him up into a real girl. This hot brunette just adores playing dress up with a fellow who is going to have so much fun wearing women’s clothes.
 
Oh, do I have a treat for you today! You see my cute lingerie? I got you the same pair of panties and a bra so we would have the matching outfits when we go out tonight. I thought that these would be perfect since nothing screams sissy than pink panties with white lace. I made sure to get a smaller size for you so they would be nice and tight so you would get that cute little muffin top.
 
I also got another pair of lingerie and these panties are too cute to be true. There is even a scrunched part for your little sissy butt. I cannot make up my mind which outfit I want you to wear for our big night out. I also got you an amazing pink dress which is going to bring out your figure. You will not be wearing a lot of makeup this evening since I want people to see that basically, you are a guy dresses as a woman.
 
– Mistress Selena
 

 
Kandii Kiss wants to doll up a sissy boy into a hot blonde sex bomb so she got him some hot lingerie and a nice wig. This cute mistress is also going to treat her slave to some nasty JOI.
 
I am so ready to dress you up into a pretty little slut that I know you can be. We are going to start by dressing you into this black thong since it is a sign that you want to fuck. Then I will put this garter on you so you can get some stockings as well. I also got you a matching bra because you are not going to be a proper lady without a pair of nice tits. And I got you this pretty blonde wig since blondes have the most fun!
 
I can see a bulge in your panties so slide them to the side and grab your prick. Start stroking it up and down. I want you to masturbate as fast as you can. This should be a workout for you. You can even wave the long hair you have while you are touching yourself. I am going to give you a countdown so you can blow your load because I can see that you really desire to do so.
 
– Kandii Kiss
 

 
Samantha Grace is not happy with the way her slave has been acting so she is going to make him wear some girls’ panties as well as a nice cock cage. This mistress is not joking when it comes to punishing her submissive friend.
 
I am not too happy with you since you have been pretty bad. Now I will have to punish you and your punishment will be to wear these neon orange panties. As an addition to that, you will wear these blue high heels and this metal chastity device. I will also put some ankle cuffs on you as well as handcuffs.
 
This is all happening since you were not following the rules. You had all of these chores around the house and you have not done any of them. From now on, you are going to be cleaning in your new outfit. I know you are upset because it will take five times longer but that is what you get for not being obedient. What were you doing all week long? Were you sitting in front of the computer and masturbating? Well, I thought so. The one thing that I have noticed when I checked your internet history is that you have been watching a lot of sissy videos.
 
– Samantha Grace
 

 
Nikki Daniels wants to show a pervy boy a good time but first, this hot brunette needs to fix his appearance. Her friend is in luck since the hot babe has a whole wardrobe just for him.
 
You envy girls and their pretty little outfits that they get to wear. You would just love to be able to do your hair like we do or wear a sweet scented perfume. Well, today is your lucky day since I am going to make you into a real lady. I have all the tools ready. First, I will fix your face by putting some powder on it. I bet you feel more feminine already. Pucker up for some bright pink lipstick. Next up I am going to do your hair. I want you to be super cute and for that, I will need to take care of your hairdo. A girl cannot go out without nice earrings so I got you those as well.
 
Let me show you an outfit that I have picked up for you. There are some nice panties here for you and this matching bra. And for the grand finally, you are going to squeeze in this zebra print dress. It is backless so you are going to attract a lot of guys tonight when we go out to the club.
 
– Nikki Daniels