Samantha Grace needs to punish her slave for not obeying her rules so she made a few changes in his daily routine. She will dress him up in some girly clothes just so he can be more attractive to his future fucking buddies.
 
I can see the cum stains on your panties. What did I tell you about that? Now, I have a new punishment. Obviously, you cannot be trusted with panties because you are going to cum-stain them so I think I am going to have to put you in a pair of yoga pants, like mine. You will have to wear these pants so you don't get any jizz on your panties. Would you feel nice in a tight pair of pants? In addition to this, I will put you in a nice bra as well.
 
The other aspect of your punishment for being a dirty boy will be a nightly ass pounding. You are going to be fucked up your butt every night by a different person. I will turn you into a slutty girl who is going to be drilled by horny men. It is time for you to get ready because we are starting tonight.
 
- Samantha Grace
 

 
Miss Medina is destined to make sure that you fully embrace the fact that you're a sissy. She's got an outfit for you today - go and try it on!
 
Slave boy, come over here! I got you some nice stuff today from the shops. Let's start off with this pink top - I think it looks absolutely fantastic, and I'm so looking forward to having your sissy ass in it! Oh, before you slip it on, get naked and start with the thong. That has to be the first thing that I see the feminine you wearing.
 
Wow, that's just absolutely fantastic. I never knew that you'd be such a great transvestite! All that's required now is for you to get these high heels around your feet and we're set to go. Oh, this dildo? Don't worry about that for now. I'll introduce you to this guy once we're doing with the makeup. I think you're going to like what I have planned for your feminine ass though.
 
- Chi Chi Medina
 

 
Kinky fellow craves Penny Barber's attention but in order to get it, he will have to put on a cute pair of panties and a sexy bra and do whatever his mistress tells him to. This is going to be a great sissy experience for a brunette's slave.
 
I see you but I am kind of busy so move out of the way, please. What do you want? You want me to come and play with you? When you were gaming I had to put on some slinky lingerie and parade in it just to draw your attention. Now, if you want me to pay attention to you, maybe you should go and put on something cute. Go put on that sexy set with bows all over it, see where that gets you.
 
Omg, you are actually going to do it. I did not say that I only had to put a sexy outfit. I also had to do some stuff. Remember how I had to crawl on my hands and knees, arch my back and put my butt in the air? Why don't you do that? Or you can lie on your back and spread your legs. That cock is not restrained by those panties, I can totally see it.
 
- Penny Barber
 

 
Nasty blonde Olivia Rose craves to doll up her man in a sexy attire and take him out on the town. This hot babe with tattoos wants to feast her eyes on her sissy boy choking on a handsome fellow's boner.
 
Hi honey, I know that we have been dating for a little while and I haven't gave it up yet. There is one thing that I will need you to do in order for that to happen. It is not really that big of a deal. You are going to have to dress up for me like a pretty princess. I will put you in some nice lingerie, some nice clothing and some heels before we go out.
 
We are going to go to a fancy club, just the two of us. Once we get there I am going to find the biggest cock for you. Guess what you will have to do! You will have to suck some dicks for me. I want to see you take a big fat boner down that throat of yours. Then you will be able to get with me. But first I really want to see you give a blowjob to a hot stallion while being on your knees.
 
- Olivia Rose
 

 
Jewell has everything planned out for their night out but first, she needs to sissify her slave boy who is looking forward to wearing his new dress. This experienced mistress wants to make him look very pretty.
 
I hope you like that pretty little dress I got for you. Do you want to get punished? If you don't, you better put that dress on! That is much better. Well, I think you got the idea what we are going to do tonight. I am going to dress you up and we are going to go out on the town!
 
The dress is just a begging, you have put on those nice panties I got you and those lacy top thigh-highs. You should be careful when putting those on, don't run them! My, my, you look great! Now I have set out some lovely jewelry. We are going to put some makeup on you as well. Some blush for the cheeks and some lipstick for those sexy lips. All you need is your wig and your high heels and you are ready! I will take you to this hot tranny club so we can find you a stiff tranny cock to suck on.
 
- Jewell Marceau