Sissy Chronicles 1.3: 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 8:


I immediately got in my car, tore off what I was wearing and put my original clothes back on. This time without the bra or panties. I was so mad I raced home, easily going 20 mph over the speed limit.

It was 6 by the time I got home. I had my first normal night in weeks, I played video games, watched some Netflix. Stuff I haven’t had the time to do because of everything Olivia was having me do.

I was so mad I hadn’t looked at my phone all night, when I finally did I had about 100 missed calls face times and text messages from Olivia. I put my phone on airplane mode.

Eventually when it was time to go to bed, I decided to watch some porn for the first time in weeks. I decided to watch some lesbian porn, with Faye Reagan. The last thing I needed to watch was a dick. After a while, I had watched a number of lesbian videos, nothing was really turning me on. My dick wasn’t even hard. I started watching some guy/girl videos. As I watched I kept picturing Jack fucking Olivia. I also noticed I watching a lot more of the cock in these videos, than the girl. I finally gave in, and started watching gay porn, now I was full blown jacking off until I came.

As I laid in bed, I was having some post but clarity. What have I become, did I really just cum to gay porn? After I couldn’t even get hard from two girls fucking? What is happening to me? Worst of all, I was still horny from watching the two gorgeous cocks.

I knew what I had to do. I got out of bed, ran to my car, and grabbed the bag that has the pink maid outfit in it. I sprinted up to my room, in fear my parents would catch me, thank god they were asleep. I quickly put the maid outfit on, grabbed the custom dildo of jacks cock, that mistress Olivia gave me.

I set the dildo on the wood floor, as I quickly lowered myself onto it. I began softly moaning, “oh jack fuck me, please fuck me.” I rode jacks fake cock for about 10 minutes, before I could feel myself about to gum, I hadn’t even touched my dick. To my astonishment I came, just from riding the dildo. I just had my first sissigasm. I sat on the ground, proud and stunned at what had just happened. Then, without thinking about it, I began licking my cum up from the floor. I was a full blown sissy whether I liked it or not.

Part 9:


It was now 12:30, but I immediately called Olivia, I knew this moment couldn’t wait.

Olivia: “Dan I am so so sorry about earlier, I don’t care if you want to be my sissy or not, I just want you to be my friend again.”

Dan: “yeah yeah mistress that’s not important. I had my first sissigasm tonight, from the jack dildo you gave me!”

Olivia: “ahhhh oh my god Sarah or uh Dan that’s great!!”

Dan: “I know!! I couldn’t believe it.”

Olivia: “sooo what does this mean?”

Dan: “well I think, I officially know my place now, I’m a sissy. And I want to be your sissy, mistress Olivia.”

Olivia: “aww omg I’m crying right now, I love you so much I thought I lost you forever.”

Dan: “I love you too.”

Olivia: “if you’re really my sissy again, prove it. Put on pink panties, short jean cut booty shorts, that pink crop top I got for you, and drive over to my house.”

Dan: “right now?”

Olivia: “yes right fucking now.”

Dan: “yes mistress.”

I walked quietly downstairs, praying my parents didn’t wake up. I decided walking through the backyard would be quicker, rather than opening the garage, which would obviously cause a ton of noise. I got to my car, started it, and once again prayed that the noise of the car starting didn’t wake them up.

I began the 15 minute drive to Olivia’s house, when I got just outside her house, I saw her standing in the driveway.

I got out and she immediately hugged me and kissed me. As she reached into my waistband, checking to see I was wearing the pink panties, she requested. We stayed hugging for a good minute or so, before I stepped away.

Dan: “Before you say anything mistress, I think me having a sissigasm was a bit of an aha moment for me, you know like a life changing moment. That made me realize, that I’m ready to be a sissy. Deep down, I’ve always known I was a sissy. But I spent years trying to hide it. Now I’m ready to come out as a sissy. Like what you’ve been doing to me the past few weeks, you’ve had to force me to do everything, but deep down, I’ve loved every second.”

Olivia: “awww I’m so happy I could help you realize that. Even if it was in a way but of an archaic way.”

(We both laughed.)

Olivia: “but you know, I was going to go easy on you, until you said that. I was even going to give you the option of not wearing the chastity cage or butt plug.

Suddenly, mistress pointed at the ground at my feet, as I stood a few feet in front of her. I looked at her quizzically.

Olivia: “that means fucking kneel.”

I immediately dropped to my knees.

Olivia: “since you want to be a sissy so fucking bad, I am going to have to amp up the training That means from now on, you will submit to my every wanting action. I will be introducing you to people you know, friends of mine, strangers, friends of jacks, and you will do whatever I say or whatever THEY say. You give me permission to do that?”

Dan: “yes mistress, not only do I give you permission, I want you too. I want the world to see me as a sissy.”

Olivia: “oh we’re going to have a lot of fun then bitch.”

Olivia: “Now, since you were a good girl tonight, and wore exactly what I told you. Here is your chastity cage, and butt plug. Since I believe I can trust you now, I am going to allow you to put the cage on and the butt plug in when you get home. Absolutely no jacking off before that. Do you understand?”

Dan: “yes mistress Olivia.”

Olivia: “good.”

Olivia moved her hand an upward motion as if to summon me up, I stood up and she hugged and kissed me again.

Olivia: “I’m so happy to have my best girlfriend back. I know with all these changes it may not sound like it, but please remember that I love you no matter what, I’m just training you so that you can be the best slutty girl ever!”

Dan: “yea mistress, I know. I love you too.”

I walked away and got in my car, I started driving home with the biggest smile on my face, I couldn’t be happier.

Part 10: 


Before I start this story, let me describe some characters in this story I have yet to mention:

Brooke: Brooke was probably my biggest bully, I had known her since elementary school. She would always make fun of me for being short, skinny, for years she has said all I needed was tits and I’d have a girls body. In 7th grade, she pantsed me in front of the entire school during recess! My shorts and boxers feel to the floor, as 50 or so people roared in laughter. Thank god I wasn’t wearing panties that day.

About Brooke: She is 5’6” about 115 pounds, with bright blonde hair, amazing double D tits, and a great ass. Brooke had a boyfriend named Bobby, who was on the football team, but I didn’t really know him.

When I got home, I immediately put the cage on, followed by the butt plug. Despite the fact I was hard and horny the entire 15 minute drive home, I desperately wanted to please mistress Olivia, so I followed her instructions. I then recorded a video of my chastity cage, and the butt plug and sent it to Olivia. Olivia responded.

Olivia: “Such a good girl sissy! You know exactly how to make me happy! Since you’ve been such a good and willing sissy girl, the checks at school will no longer be required. But I will be doing random checks, and if I found out you’re not wearing your cage, you will be EXTREMELY punished!”

Dan: “thank you mistress, I really try hard to be a good sissy girl for you. And I promise I’ll wear the chastity and butt plug every day.”

2 weeks later: During those 2 weeks, I had worn the chastity cage and butt plug every day, along with my panties and bra. Olivia would invite me over to her house and fuck me with the strap on. She would talk about Jack fucking her, and how great his cock was, and she loved to talk about how much I would love his cock.

One cold December morning, I walked down the hallway towards my locker, I noticed mistress Olivia and Brooke were standing in front of my locker.

I sighed, this could get ugly quick. I didn’t even know Olivia and Brooke were friends. Olivia saw me coming, as she was standing with her back to my locker. As I walked closer, I noticed Olivia was pointing at the floor just in front of her. I immediately knew what she wanted, and began to panic. However, I knew better than to deny her.

I quickly dropped to my knees, as Olivia and Brooke continued their conversation without even acknowledging or looking at me. I began to notice all the people in the hallway. I tried to keep my head down and not look, but I couldn’t help but notice the amount of people snickering and laughing at me. God knows how many people saw me, I assumed probably close to 50. I sighed, by the end of the day everyone would know I was a sissy.

Mistress Olivia summoned me up with her hand, and I rose to my feet.

Olivia: “Sissy introduce yourself to Brooke.”

I knew what was expected of me, I curtsied and said:

Dan: “Hi Mistress Brooke, I’m Sarah.”

Olivia and Brooke immediately bursted into laughter.

Olivia: “Good girl Sarah. You remembered how to curtsy and how to address Brooke. I’m impressed.”

Brooke: “Now sissy, you are to meet both of us, in the check in bathroom at 10:30. You better not be fucking late.”

Olivia: “I hope for your sake you’ve been shaving your legs bitch.”

They walked away, talking and laughing their way down the hallway. I was now thrilled that I shaved everything below the eyebrows, this morning. But what could mistress Olivia and Brooke want?

Part 11:


Before I start this story, let me describe some characters in this story I have yet to mention.

Ben grew up as my neighbor, he was my first friend at 5 years old, and is still one of my best friends today, he is my one of two friends. We often play video games together. Like me, Ben is also not very popular. But he rarely gets made of, like I do, he kinda just gets ignored.

Reminder: Ben and mistress Aubree, grew up on my street. Aubree I’ve had a crush on since the 6th grade, but I’ve never acted on it.

About Ben: despite his neediness he’s oddly somewhat good looking. He’s 6’1” 190, with a lean build, and black square glasses. He’s one of the smartest in the class, and is pushing to be the valedictorian.

It was currently a little after 8:00, I had to meet mistress Olivia and mistress Brooke in the bathroom, in 2.5 hours. I was extremely antsy, nervous, and oddly excited about what they had in store for me. I kept asking myself why did Olivia say she hoped I shaved? I was so lost in my own thoughts, that I didn’t notice the snickers and people laughing at me. Suddenly a tapping on my shoulder got my attention, I turned around to see Ben sitting behind me.

Ben: “hey man, uh why were you kneeling in front of Olivia and that bitch Brooke this morning?”

I froze. I had no idea how to answer this question.

Dan: “oh uh uh I don’t know I’m just doing her some favors.” I said quietly, desperately trying to keep the rest of the class from not hearing.

Ben: “some favors? What the fuck kinda favors are you doing?”

Dan: “oh uh I don’t know, it’s not a big deal, just drop it. Okay?

Ben: “okay man, but just so you know there’s a million pictures of you going around.”

Ben showed me some photos of me on my knees. I looked more pathetic than one could possibly imagine. No wonder why everyone was laughing at me.

Dan: “oh uh yeah I saw those already.” I lied, desperately trying to end the conversation. I turned back around and pretended to do some schoolwork.

Finally the bell rang and I walked to my next class, followed by more snickers and laughter in the hallway. During the next hour, nothing interesting happened, physics class was extremely boring.

Finally it was almost 10:30, I practically sprinted to the bathroom, near the school theatre. Opened the door and to my surprise, nobody was there. I decided to kneel on the cold, hard, bathroom floor. Figuring that would make mistress Olivia and mistress Brook happy. 10 minutes passed, 15 minutes passed. All this time I stayed kneeling on the floor.

Finally the door opened.

Part 12:


The door swung open and mistress Olivia and mistress Brooke, and to my surprise, and bewilderment, begins them walked in mistress Aubree.

The last thing I wanted was Aubree to see me like this, in such a pathetic state. I still had hope that Aubree could one day be my girlfriend. If I remained kneeling on the floor, being ordered around, doing whatever they have planned for me, I’m sure any hope would be all but shot. But I knew better than to stand, or disobey orders, for fear I would be punished.

Olivia: (laughing) “What a good little bitch kneeling pathetically on the floor. Exactly where you belong. Now we brought you some presents, that you’re going to love.”

Dan: “Thank you mistress, I’m sure I will love them.”

I now noticed Olivia was carrying a gym bag, I began to get horny at the thought of what my presents could be.

Olivia threw the bag in front of me, I began to open it. Inside the bag was a black skirt, black leggings, a pink sweater, black shirt heeled booties, and a pink handbag. I looked up at my three mistress confused. (The outfit is linked here the outfit is that, minus the necklace, and booties instead of heels.)

Olivia: “Sarah these are for you to wear today. We were nice enough to buy these clothes for you. I hope they all fit, we tried to buy the right sizes.”

I was trying to hide back tears, did this mean what I thought it did?

Dan: (almost crying) “so so does this mean I have to wear these around school?”

Olivia: “Yes it does. But that’s no way to thank your mistresses we did a lot of hard work to put this together. Say thank you.”

Dan: “Thank you mistress Olivia, Brooke, and Aubree.”

Aubree: “Well come on sissy let’s try them on!!”

Hearing Aubree call me sissy stung a little bit. I wanted to change in the stall, but I knew mistress Olivia wanted to humiliate me by showing off my caged clitty to Aubree and Brooke.

It now struck me that Aubree has yet to see my clitty. After everything that happened a couple weeks ago, I had forgotten. In fact, nobody but Olivia, has seen my clitty.

I slowly began to take off my clothes, dreadful of the fact that I would eventually be standing in a bra, panties, and chastity cage, in front of, the girl of my dreams, and my biggest bully. I now realized all three girls were filming this.

I pulled off my shirt and shorts revealing my bra and panties, both Aubree and Brooke giggled as Aubree walked towards me, knelt down and began messaging my caged clitty.

Aubree: “I know you’ve been obsessed with me for years now. I know how big of a crush you’ve had on me forever. If you want to cum tonight, you will do exactly as we say today.”

I hadn’t cum in over two weeks. I was so desperately horny I would do just about anything.

Dan: “oh yes mistress Aubree please, please, I’ll do anything to cum.”

I quickly said, as I grabbed leggings and began to put them on. Aubree and Brooke began to help me roll them up my smith legs, as Olivia filmed.

After they were on, I put on the rest of the outfit. I looked at myself in the mirror, my body looked passable, but looking at my face, I was clearly still Dan. There was no hiding that.

Olivia: “aww Sarah you look so pretty! The boys are gonna be all over you!!”

Aubree and Brooke laughed. I blushed, realizing that a boy coming onto me might actually be a possibility. I blushed even more, as I thought to myself that I wanted that to happen.

Olivia: “Sarah now that we have you all dressed, we want you to set up social media profiles for yourself. So let’s go to the court yard and take some pictures.”

I quickly began to panic, the courtyard was a few minutes away, and just about anyone could be walking in the hallway. Realizing I had no choice, the four of us began walking.

Olivia: “hi chase!”

The three girls stopped walking to talk to this guy Chase, as I stood a few feet away.

Chase: “yeah you guys should definitely come.”

Aubree: “oh well definitely be there, we’ll see you there!”

Chase walked away, as the girls started walking towards me.

Olivia: “Sarah you need to learn some manners. That was your first time meeting a guy dressed, so I’ll cut you some slack. But next time you meet a man you are to introduce yourself.”

Dan: (embarrassed) “you mean you want me to curtsy??”

Olivia: “Yes and you’re going to apologize to Chase next time you see him.”

I knew better than to argue, but I was unbelievably humiliated at the sheer thought of having to curtsy in front of a man next time.

Dan: “Yes mistress. I will be better next time.”

Olivia: “good bitch. Now let’s take some photos.”

We went out into the courtyard, the courtyard is surrounded by classrooms and hallways, so anyone could just lookout and see me. I could only imagine the snickering and laughing going on behind closed doors and windows.

We took a million pictures in a million different posses. We recorded tik toks, we made Snapchat videos, we posted pictures on instagram.

The girls told me they wanted me to create my own bio and captions on pictures.

My bio: Sarah Peskin. SHS.  I truly wanted to make the bio as girly as possible. My first post was a collection of 5 photos of us doing ridiculous poses. I captioned it “loving life with the girlies”

Olivia: “After school today we’re taking you shopping, we need to get you some clothes. You are to wear girls clothes now everyday, anytime you are out in public.”

Dan: “okay mistress but what about my parents? My dad works from home, and my mom does all my laundry. They’ll surely find out eventually.”

Aubree: “Don’t worry sissy we have that all figured out. You are going to leave all your clothes at my house. You are going to change every morning at my house. Both my parents leave for work early, so we’ll have the house to ourselves.”

Dan: “oh okay well that sounds good then.”

Olivia: “See sissy we have this all figured out. Now after school meet us at Aubree’s car. We’ll go shopping from there.”

Dan: “yes mistress, I’ll see you there.”

I walked away, now realizing I’d have to not only survive the school day dressed as a girl, but also have survive the mall. I smiled.

Lucy Little

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