Sissy Roleplay – Let’s Play Dress Up Part 1 – STE – A – 0009 – 07-11-23

Hey! I’m so glad you decided to come over today. I’m really excited to get to spend some time with you. I feel like it’s been so long since it was just us, you know? You look really nice today, too. I see you’re all dressed up! I love the look.


What’s that? You say it’s not really what you wanted to wear over? You had another outfit in mind? Well, now I’m curious! What else were you planning on wearing? Oh, don’t be shy! You can tell me anything. We’re friends, after all! Oh, you don’t own the kind of clothes you really wanted to wear? Well, why don’t you tell me what you had in mind? Maybe we can find something that you like better?


We could go out shopping if you want!


You’re not sure? That’s okay. Why don’t we hang out here at my place for a little while first, and then if you change your mind we can go out and shop – how about that? Would that be okay? It is? Perfect!


Come sit on the couch! I cleaned up the whole house all by myself yesterday, doesn’t it look nice? Oh, you can take your shoes off if you want! Make yourself comfortable. Oh, you like my dress? Thank you, I got it from a little thrift store down the road. It has pockets, hehe. Do you want something to drink? I’ll get us some water.


Here you go! You know, I noticed how you’re looking at me. Is there something you want to tell me? Oh, don’t be shy about it! I wouldn’t be mad or judge you at all. You know that, right? You do? Well, then tell me what’s on your mind!


You think I’m really pretty? That’s really sweet of you to say. And you really like my outfit today? Hmm… Do you want me to make you pretty, too? You think I haven’t noticed the way you look at women? I mean, you’ve never expressed any interest in women before, but you always like to talk about their clothes and accessories.


Why don’t you…let me dress you up?


It’ll be fun, I promise! You’re pretty small for a man, so I bet you could fit into some of my clothes. Wanna try it? I just know you’ll look super pretty and cute with the right outfit. Come on, let’s go raid my closet!


Thank you for reading part one of my very first sissy blog, Let’s Play Dress Up! I know all you sissy boys out there are dying to hear me actually say this kind of thing to you, so make sure to check out my audio!


If you liked this you’ll love my friend Natalie’s blog!

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