Sissy Roleplay – Let’s Play Dress Up Part 2 – STE – A – 0009 – 07-11-23


Hey sissy boys! Welcome back to part 2 of my blog, Let’s Play Dress Up! If you need a refresher check out part 1 here! Let’s pick up right where we left off.


Here, why don’t you sit at the foot of my bed and I’ll pull some clothes out for you to try on? Okay, perfect. Just hang out right there while I look!


You always wanted to get dressed up pretty? I could kind of tell that. Is it just because you want to look pretty for yourself? Or…do you want to dress up for someone else? Oh, it’s that one, isn’t it? Hehe. I can tell, it’s written all over your face. You have a crush on someone and you want to look cute for them, right? Is it a man? How did I know?


Well, a sissy boy like you would probably love to be caressed and touched by a big, strong, manly man, right?


Mhm, that’s what I thought. You totally want me to dress you up to go see him, don’t you? Oh, you’re too shy to let him see you like that? That’s okay, we’ll build up your confidence so you can meet up with him while looking your best! I’ll help you out, okay? So don’t even worry about it! I’m going to make you the most pretty and beautiful sissy girl just for him.


Here, try these on! Don’t be shy, you can change in front of me. Girls change in front of each other all the time. Try on this dress! It’s cute, isn’t it? Don’t you love the way the straps are ribbons that you tie into bows? It has pockets, too!


What do you think? You look super cute and pretty in it! That color suits you perfectly and it’s not too short or long on you. It was like, made for you. You have the perfect girlish frame for it. Why don’t you keep it? I think it looks really good on you! It makes you look like a little doll, so sweet and pretty. You like that one? Okay, perfect.


Now…what if I do some makeup on you?


Can I do that? I promise I’ll make you look so beautiful! …It’s okay? Yay! Okay, just come sit over here in front of my vanity. I have an extra chair, so you sit in this one. I’m just gonna do something light since you’re a natural beauty. Just a little bit of foundation will cover the uneven coloration spots. Add a little bit of blush to bring back some color to your cheeks. A dab of this lipstick will make your lips so kissable! What color eyeshadow do you want? Oh, I love that color! It’s totally you, it looks so good! Close your eyes and I’ll just apply it really quick.


And done! You look so beautiful, such a pretty sissy girl. Look at yourself in the mirror! Do you like it? Mhm, I knew you would. You just want to be dolled up like a girly girl too, don’t you? I totally get it. You look amazing, even better than a lot of girls!


You should totally call up your crush and ask him out while you’re feeling confident in yourself! I bet he’d love to take you out. Maybe he’ll even want to take you back home after your date, hehe. I bet he’ll just want to completely ravish you when he gets you alone. You know, men are like that. They see a pretty girl and they can’t help themselves. He’s gonna take one look at you and fall head over heels.


Oh, speaking of heels! Here, try these on. Wow, a perfect fit! You should keep everything, it looks too cute on you! Maybe you can wear it out when you have your date with your crush.


I’m sure he’d love to see what a cute, pretty sissy girl you are.


Doesn’t it make you feel good to be all dressed up like this? You should visit me more so I can dress you up again and again! Next time, we’ll go shopping and pick out some cute, girly outfits for you. You’d like that? Perfect, it’s a date then!


Thank you for reading part 2 of my blog! Make sure to pick up the audio here to listen to this blog in my sexy voice! I know you want to, sissy boy!


If you liked this, make sure to check out my friend Ruby’s blog, too!

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