Hmmm, what should we dress you up like today? Why don’t we try a pretty little princess? Or maybe a sexy schoolgirl.
 
You always look so cute when we dress you up like a girl. One of these days we are going to have to take you out to the bar when you are all done up and try to find a man for you to bring back and fuck.
 
– Carissa Montgomery & Jade Indica
 

 
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
 

 
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
 

 
Star Nine has always imagined that you would make the perfect little sissy. Now that you’ve approached her as your crossdressing master, she finally has the chance to involve herself in your favorite fetish.
 
Are you ready to be my perfect, pretty little girl? I hope you can handle just how feminine I’m going to make you. It doesn’t make you a faggot to want to be a sissy slut, although I guess when you put on the floral panties I got for you using your credit card, you might feel like quite the woman.
 
Now, open your legs and show me what’s there. Ugh! Shave your legs, make them smooth for me. You know that pretty little girls do not have hair all over their bodies. Put the bra on for me and start to pad it, I want to make sure those breasts are big and juicy – just the way you want them to be in your ultimate crossdressing fantasy. Look how pretty you are with a stuffed bra! You’re well on your way to be my favorite little sissy slut.
 
– Star Nine
 

 
Whitney Morgan wants to check out her date’s kinky obsession with women’s clothes so she will ask him to strip for her. This hot blonde has a great time while teasing a sissy fellow who just loves the feel of silky lingerie.
 
While you were getting out of the pool and your swim trunks sunk down a bit I kind of caught a glimpse of some panties. I mean, maybe I am just seeing things but I wanted to ask you is there something that you want to confess to me? No? Okay. Well, this is a bit unconventional for me, but how about you strip down?
 
If you don’t want to, you know where the door is. But I can see that you will do anything for me. Come on, I don’t have all day! Take off that shirt and let me see you get out of those swim trunks. Wow! Are you wearing red silky women’s panties?! How amusing is that! Take those off as well and make sure you are still a man underneath them. You were wearing all day long. What, you want to be in touch with your feminine side? Is that it?
 
– Whitney Morgan