Hey there, back again so soon? You couldn’t wait another minute without me dressing you up like my own little sissy doll.
 
Well, lets get you all nice and pretty so why don’t you put on this dress and these panties while I get your wig ready. You are going to look so cute after I get through with you!
 
– Carissa Montgomery
 

 
Samantha Grace has a bunch of useful tips for her sissy slave on how to improve his looks. This hot mistress with amazing boobs wants to help a fellow out when it comes to make-up and some other areas.
 
Today I got you some new panties and a nice matching pink bra. Finally, you have earned yourself a slut thong! I know you have been working a lot on your make-up skills for me and it looks divine! I love the cat eyes that you have been doing. But now I think it’s time you used some false eyelashes. You need to make your eyes look big and seductive so when you flap your eyelashes all the men go crazy. You will be the best sissy boy on the block.
 
Another thing that we should add is to get you tanned because it will make your bimbo qualities even more noticeable. I will have to explain a bit about highlighting and contouring because I want your face to be perfect. I love giving you these small tips on how to improve your look. You are going to look amazing if you just follow my instructions. I am doing all of this just for you.
 
– Samantha Grace
 

 
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
 

 
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
 

 
Snow Mercy wants to show off her sissy friend but first, she needs to doll him up in some great clothes. This hot brunette is also going to take care of a fellow’s makeup and turn him into a hot chick.
 
I know that you are here because you want to be a real girl like me, but since we cannot do that we are just going to have to pretend. I am going to make you come to my house and because I am a big girl I will let you wear my clothes which are going to fit you nicely. I think some of my panties would make you look so cute. Maybe some black silky ones, what do you think?
 
You can put on one of my bras before we find a perfect dress for you. You should wear something that is going to show off your legs, but you should shave them first. Because I am going to paint your toenails you should wear some strappy shoes and I will teach you how to walk in high heels just like a real girl. I am also going to doll you up with some great makeup and everyone is going to see how pretty you are.
 
– Snow Mercy
 

 
Nikki Brooks is up for a kinky session with a fellow who really wants to experience dressing up like a chick. This hot blonde goddess will treat a hunk with a great girls’ night out as well.
 
You should be yourself around me and besides, just because you have a cock doesn’t mean you cannot look pretty. Be a good little boy and let me dress you up. You were acting like a perv the other day, and sniffing this particular piece of clothing but all of that is nonsense. You wanted to see if this orange lingerie was going to fit you. Don’t worry, it is your size. And do not be concerned about the bra area, we can find you the one that fits and stuff it.
 
Also, I am going put some makeup on you and completely change your face. Nobody is going to know it is really you. We can go out after I am done feminizing you. Just think about all those boys who are going to be drooling over you. I want to see you play with one of the boys’ cocks and see those hands go up or down his shorts.
 
– Nikki Brooks