Sissy Chronicles 1.5: How I met my mistress and became a sissy. By: u/SnooChickens9965

This story was originally posted on Reddit. I compiled all the different parts on this site so more people could enjoy u/SnooChickens9965 work. Have fun!



The following fictional story was posted on Reddit by u/SnooChickens9965 all the rights to this story belong to them. I compiled all the different available parts on this post for everyone's enjoyment on this site. If you want to thank them send them a DM on Reddit. This is my 3rd time compiling everything since it always crashes, if you can leave a like and comment I would thank you so much haha.


Part 18 A:


We were in Aubree’s bedroom, as Aubree was doing my makeup. Aubree often bragged how good she was at doing makeup. She was part of the drama club at school, and would often help people in the play with there makeup.

She began by applying foundation, reshaped my eyebrows, applied some blush, and followed this by putting on eyeshadow, eyeliner, mascara, and finally lipstick. After 45 minutes she was finally done.

Aubree prevented me from looking in the mirror during those 45 minutes, she said she wanted me to be surprised when I finally saw myself. She was beaming with excitement and couldn’t wait for me to see myself. She dragged me in front of the mirror, and I stood stunned in front of the mirror for a minute.

Aubree: “so what do you think?”

Dan: “I… I look beautiful.”

I no longer looked like a man, if you just looked at my face and hair, you would think I was a girl. I still very much had a male body, but even that was about to change.

Aubree: (very excited) “oh my god I knew you’d love it!!”

Aubree squealed, as she hugged me.

Dan: “thank you mistress Aubree for making me all pretty.”

After she was done, Aubree began painting my toes and fingers. The toes she painted pink, and the finger nails she painted white, with pink french tips.

Dan: “wow Aubree you’re really good at this. They look great.” I said, marveling at the work she had done on my fingers.

Aubree: “oh yeah I know, I’ve always kinda thought about becoming a makeup artist.”

Aubree: “alright Olivia you’re up.”


Part 18 B:


Olivia: “Sarah since you’re wearing a dress tonight, we need it to fit properly, so in order to do that we got you fake tits. They’re B cup sized tits, so they’re not to big, but they’re definitely noticeable.”

Dan: “wait but didn’t I try it on in the store?”

Olivia: “well yes, but we intentionally bought it big, we told the sales lady you’d be wearing fake tits, so she got a B cup sized dress. A dress with a flat chest? Come on, it would just look stupid. Please wear them, it would make us so happy.”

I supposed she was right, it would look rather stupid. Even still, I was suddenly extremely anxious, I didn’t want to do this, but I guess I had to in order for the dress to fit properly.

Dan: “okay fine I’ll wear them, but just to make the dress look normal. I’m not doing this all the time.”

Olivia: “of course not. Let’s put them on.”

Olivia applied some type of adhesive glue to my chest, and then stuck on the breast forms. The breast forms were a rubbery type material, that felt weird, they kinda looked like plastic tits, on a life size Barbie doll.

Then it came time to put my dress on, my mistresses helped me into it. Once it was on, I looked at myself in the mirror, I was shocked at the reflection I saw. I kept running my hands over my body, and face, I couldn’t believe what I was looking at.

The girls were all applauding me, and complimenting how gorgeous I looked.

Aubree: “Sarah you look hot! The boys are gonna be all over you tonight.”

The girls are laughed, I blushed, I didn’t know whether or not I wanted that, but I certainly didn’t deny it

Brooke: “he really does look like a girl, you can’t even tell he’s a man, or used to be a man.”

Aubree: “well he certainly was never a real man!”

More roaring laughter from the three girls.

Olivia: “okay laughing at our sissy is great fun and all, but we still have to teach her how to be a girl! So next let’s teach you how to walk in heels. Sarah go in my closet and get those white heels we bought.”

I went into Sarah’s closet and got out the white heels. The heels were 6 inch, with a high 6 inch stiletto, the toes had a wide base, the resembled more of a traditional shoe. On top of the heels, they had a white strap going across the top. They were open toed shoes, kinda like sandals.

The girls instructed me how to walk, to puff out my chest when I walk, and to make sure I land on my heel, when walking. They told me to walk heel to toe, don’t walk with such a wide base. The girls laughed as I walked like this, walking like this caused me to sway my hips a lot. After 30 minutes, and lots of falling, I finally had the walking down.

Olivia: “have you ever been to a party like this?”

Dan: “uhh..”

Brooke cut me off.

Brooke: “of course he hasn’t, he’s a loser. He had to become a girl, just to get an invite.”

All the girls laughing.

Aubree: (while laughing) “now Brooke while that’s true, that’s no reason to laugh at him. Dan knew he was and wasn’t going to have success as a man, so he became a girl. He became Sarah.”

Olivia: “tonight is just another step in your feminization process sissy.”

Dan: “Yes mistress.”

Aubree: “now we’re going to teach you how to dance. There are going to be a lot of hot guys at this party and we expect you to find one to dance with.”

Dan: “yes mistress Aubree”

Aubree started playing some rap party music from her phone, and started to show me how to shake my ass, as I tried to copy her. She then walked over to Olivia and began twerking her ass on Olivia, pretending that Olivia was a guy.

Olivia: “okay now Sarah you try.”

I walked over to Olivia and began grinding, as the girls called it, on Olivia. I tried to really impress them, I was bending over at the waist, moving my ass up and down. This went on for a few minutes, as the girls laughed the entire time. After the song, I stopped dancing and suddenly thought of something.

Dan: (very nervous) “umm so when you’re dancing with a guy, can you feel, if you know, he gets a boner.”

All three girls started giggling.

Olivia: (giggle.) “Yes you can! Hopefully you get a few guys hard tonight, sissy!”

Aubree: “well, if he has a big enough dick you can feel it. You could never feel that clitty, with or without her little cage.”

Aubree said pointing at my clitty. I blushed once again.

Brooke: “getting a guy hard, just by moving your body, is such a great feeling. The power you will have over him. Get him hard and he’ll be putty in your hands, Sarah.”

I didn’t want to show it, but this all made me very horny. Thank god the girls couldn’t see my clitty, I could feel myself straining in my cage.

Olivia: “now when you’re dancing with the guy, his hands are going to wonder. So don’t be surprised when he grabs your ass, tits, or your little clitty.”

Aubree: “oh and another thing, make sure you take off your shoes when dancing. We don’t want to break those. And you’ll be a lot more comfortable.”

Olivia: “alright it’s almost time to go, let’s go!!”

We piled into Olivia’s car, as she drove us to Chase’s house for the party.

Lucy Little

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Lucy Little 3 w

Sorry for not posting the continuation, I won't allow me to here are the links for the next parts, enjoy!
PART 19:

PART 20: