Sissy Chronicles 1.2: 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!

Disclaimer:

 

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 5 A:

 

We got in Olivia’s car, and I asked her a question that had been bothering me.

Dan: “so mistress if Jackie knows about me, who else does?”

Olivia: “don’t worry, nobody else knows about you Sarah, I promise.”

I took a sigh of relief. Mistress started rubbing the inner part of my thigh and then over my cage.

Olivia: “but, Sarah, you do have to realize that part of being a sissy is meeting other people. When you get comfortable as Sarah, I want you to meet some people, guys and girls, dressed as Sarah. I just want you to get the full sissy experience. Isn’t that what you want sissy?”

I sat there stunned for a moment, realizing that she was right. Being a true sissy meant that I couldn’t t keep this between Olivia and I. If I truly wanted to be a girl, I had to be more open about it.

Dan: “yes mistress that is what I want.”

Olivia: “perfect than we both want and expect the same thing. And plus I really hope we didn’t buy all these clothes just to keep you in hiding. Hopefully I can doll you up for some nights out on the town and other things.”

Dan: (smiling) “I’d love that mistress”

Olivia: “now I have something I want to ask you, what would you say if I asked you to be my girlfriend?”

Dan: (very confused) “what do you mean?”

Olivia: “I mean I’m asking you out. We would be dating, and be two girlfriends.”

Dan: “wait but what about jack? You’re cheating on jack?”

Olivia: (slight laughter) “no, no, I’m not cheating on Jack. We would be in what’s called a cuckold, female led relationship. Which means, I still get to date Jack, but you don’t get to date anyone, unless I say so. Basically we just continue to act how we are now, I’m still your mistress and your still a sissy. So will you be my girlfriend?”

Dan: (very excited) “YES MISTRESS YES I’LL BE YOUR GIRLFRIEND!”

Dan: “so does this mean we get to kiss and stuff?”

Olivia grabbed my face leaned in and kissed me, we sat there for a minute making out, until she pulled away and said

Olivia: “there now you’ve had your first kiss.”

I sat in horror as I suddenly realized something.

Dan: “wait so does this mean Jack knows about me?”

Olivia: “no I promise he doesn’t know about you. But remember what we talked about earlier? As a sissy you have to be comfortable with other people finding out about you, so jack will find out about you, and he will see you when your dressed as Sarah, but we’ll wait until your ready.”

I sighed as I realized she was right. I still thought it was an absolute nightmare of a situation. Jack, who, I have known since grade school, and has always been one of my biggest bullies in school. What happens when he actually has several extremely humiliating things to bully me for?

We pulled into Olivia’s driveway, it was 5:30 so we had 2.5 hours until her parents got home. We walked up to Olivia’s bedroom, and I sat on the bed.

 

Part 5 B:

 

Olivia: “alright girlfriend are you ready to get that chastity cage off?”

Dan: “oh yes mistress please, please I desperately want this off.”

Olivia: “okay but first you have to do some stuff for me. First I want you to put on the black skin tight dress you bought. You put that on, with the breast inserts, I’m going to get changed, I’ll be right back baby.”

Olivia went into her bathroom, as I striped out of my clothes and could hardly contain my excitement. I stepped into the dress, and pulled it up my shaved legs, I thought to myself, maybe I’ll finally get to see her naked, maybe she’ll suck my dick, maybe if I’m super lucky I’ll even get to fuck her. I had the dress all pulled tight, ready for whatever Olivia had in store

As I admired myself in the mirror, I began to think, if you just looked at my body, with the breast forms in place, you would think I was a girl. I must admit, I looked pretty fuckable.

Olivia walked out of the bathroom wearing a long pink robe, the robe was tied around her waist so I couldn’t see what she had on underneath.

Olivia sat down next to me and we immediately embraced and began making out. She was rubbing her hands all over my body, she took off my dress, so I was down to my bra and panties. She grabbed my hand and placed it were her pussy should have been. But instead I felt a large hard object, that was in the shape of a large cock. I sat there rubbing it for a few seconds salivating over what I knew was coming.

Olivia: “yes sissy you know what that is, why don’t you get on your knees?”

Without a word I got on my knees. I began to untie her robe, desperately wanting what was underneath. When the robe came untied, it unveiled an 8 inch, girthy strap on. I reached out for it determined to get it in my mouth. Mistress slapped my hand away.

Olivia: (laughing) “oh yes sissy, you know what you want. But first, I want to tell you that this is an exact replica of Jacks cock. So beg to suck Jack’s cock.”

I looked up at mistress and I realized she was recording me, but I didn’t care, I just wanted Jack’s fake cock.

Dan: “Please jack I need your big beautiful cock in my mouth, I need to taste it, I will choke myself on that gorgeous cock until you cum. I need to taste your cum Jack, pleeeaasssse.”

Olivia: (laughing) “you’re such a little slut! Suck Jack’s cock fucking bitch.”

I wrapped my lips around the strap-on cock as I began sucking. I bobbed my head up and down, as mistress pushed down on the back of my head. I could only get about half way down before I had to come up for air.

Olivia: “that’s okay slut, you’ll be able to deep throat no problem by the time you suck Jack’s real cock.”

I lifted the cock up and kissed the balls, then I started at the base of the cock, and licked along the length of the cock.

Olivia: (very sweetly) “you were such a good girl today, do you want to cum?”

Dan: “oh yes mistress please please I desperately do. Please make me cum.”

Olivia: “Okay then sissy, you just have to do one last thing for me. Get up on the bed, and get into doggy.”

 

Part 5 C:

 

I immediately jumped up and got into doggy position on the bed. Mistress got behind me, with her knees on the bed. We were both facing her TV on the wall. Mistress Olivia pulled down my panties, so they were on my thighs, and then pulled out my butt plug.

Olivia: “You know what to do sissy. We both know what you want and need.”

I knew mistress Olivia wasn’t talking about removing my cage. I was craving something else instead, and that something else was behind me.

Dan: “Jack please, I need your big cock inside me so bad, please fill me up. Please fuck me like the slut I am, Jack.”

As I was saying this mistress Olivia took time lubing up the strap-on and my ass. After she was done, she slowly began to insert Jack’s fake cock into my ass.

Olivia: (in a sweet voice) “does this feel good baby?”

Dan: “ugh it’s a little uncomfortable but I can manage. Go slow.”

She went very slowly, she’d go an inch, wait for me to adjust for 5 seconds, go another inch.

Olivia: “just let me know how fast you want me to go. It’s about half way in.”

Dan: “it feels so weird, it feels like my body is trying to push you out.”

After a minute or so of heavy breathing…

Olivia: “I know baby you’re such a good girl. Alright sissy that’s all the way in. Now I’m going to pull it out, and go slowly go back in.”

This went on for about 5 minutes, before I felt like I was ready.

Dan: “ohh Jack please fuck me harder Jack please.”

Mistress Olivia really started slamming into me now and I was loving it. She was pulling my hair, and slapping my ass. It’s what I managed fucking a girl would be like, only I was the girl now. As mistress Olivia continued to humiliate and degrade me I kept on getting hornier. It’s as if something had taken control over my body.

Olivia: “Do you want to cum sissy?”

Mistress Olivia reach around and rubbed my clitty through the cage.

Dan: (inbetween moans) oh yes please mistress, please mistress Olivia.”

She momentarily stopped fucking me, as reached underneath and unlocked me from my cage. Finally freedom! I reached back to jerk my clitty when mistress yelled at me. Before she began stroking me, I felt her putting a condom on me, I wondered what that could be for. I quickly lost that though, as mistress kept fucking me, I was in heaven.

Olivia: “no sissy! Sissies do not get to rub there clitty! I’m going to make you cum.”

Dan: (defeated voice) “yes mistress.”

As Olivia began stroking my clitty, she pulled my hair back, so my head would be looking at the TV, as my eyes adjusted to the tv. I saw mistress Olivia, in doggy, with Jack fucking her.

Olivia: “you like that sissy? You like watch Jack’s big cock fuck me?”

Jack wasn’t just fucking mistress Olivia, he was manhandling her. He picked her up, with ease, and threw her back on the bed, this time face up. He grabbed the camera, that was sitting on the dresser across from them.

Jack was now holding the camera so you could see his cock going in and out of mistress’s pussy.

Mistress Olivia was naked on the TV, but I couldn’t focus on that, as I was salivating over Jack’s magnificent cock.

Olivia: “you jealous of how Jack is fucking me sissy?”

Dan: “yes mistress.”

Olivia: giggle “even though I’m in a position you could only dream of, all you can think about is Jack’s cock.”

Dan: “yes mistress, I can’t take his eyes off his cock, I wish that was me right now. I want Jack’s cock inside me right now. I want to make that cock cum mistress.”

Olivia: *laughter “you’re such a fucking faggot. You will make that cock cum very soon slut. Now beg for Jack’s cock to make you cum.”

Mistress rubbed my clitty faster and faster.

Dan: (moaning) “Jack your cock feels so fucking good. Please fuck me harder Jack so I can cum.”

Mistress was still holding my head back with my hair as I watched Jack cum all over mistress’s pussy. Just as I say that I erupted into the condom. It was the best and longest orgasm of my life, it must have lasted 10 or more seconds. I immediately knew it was the most I had ever cum.

 

Part 5 D:

 

Mistress Olivia came around front, and had me get on back, she took off the condom, and without a word poured the contents into my mouth.

Olivia: “Such a good faggot slut aren’t you. I know you can’t wait to taste the real Jack’s cum. Now thank me and Jack.”

Dan: “thank you mistress Olivia and Jack for making me cum, and allowing me taste my own cum.”

Mistress Olivia took off the strap-on revealing black panties, I was so focused on the strap-on, I hadn’t even realized she was just wearing panties and a bra.

Olivia “good girl. Okay now that you have cum, it’s my turn.”

Mistress Olivia removed her panties, and then her bra. It was the first time I’ve seen anyone naked, as I stared at her naked body I was in awe. I reached out to grab her tits and she aggressively slapped my hand away.

Olivia: “No sissy! My tits are for real men. Not fucking sissies like you. Now lean back and eat my pussy.”

She said as sat on my face, with her face, facing my feet.

Mistress Olivia slowly rubbed my balls and clitty.

Olivia: “You know that video I showed you? That was made last night. Jack’s cock came right where your face is, less than 24 hours ago.

Olivia moaned and groaned as I hate her pussy.

Olivia: “you’d like it if his cum was still there wouldn’t you bitch?“

I groaned my approval in response.

Olivia: “I knew you would sissy, you’re so pathetic.”

I continued to lap at mistress Olivia’s pussy, as she continued to berate and humiliate me. Her pussy tasted sweet, and I was honestly enjoying it.

Olivia: “oh my your clitty has gotten so hard. You’re so tiny. Jack is easily triple your size.”

Mistress Olivia said as I could hear her fumbling with the chastity cage again, as I silently started to panic.

Olivia: “oh yes sissy you’re going back in your chastity cage. This time for longer as you learn to become more of a sissy.”

I tried to escape from her underneath her, I desperately kicked my legs and flapped my arms but to no avail. It got even worse as mistress tightened her thighs around my head, so much so that I became light headed. I heard the chastity cage lock, and I stopped flailing.

Suddenly mistress Olivia’s moans began to increase, she got louder and her body, began to shake, as I could tell she was orgasming. After she was done, she got up, put on her bathrobe again, and cuddled up next to me.

Olivia: “ah good job bitch, but, you need to learn to accept that you’re a sissy Sarah. Do you know why I keep you in chasity?”

Dan: “to torture me?”

Olivia: (joking laughter) “No it is not to torture you. It’s because with a cock that small, you could never please a women, your not a real man. Since your not a real man, that means your a sissy, which mean you sacrifice your own pleasure, to please someone else. The chastity, panties, and the butt plug aren’t just to feminize you, they’re to teach you obedience, sacrifice, and make you more submissive. Your cock is no longer your main pleasure organ, your boipussy (ass) now is. Does that make sense?”

Dan: “yes mistress.”

Olivia: “Are you ready to accept your fate as a sissy? That means no asking me questions about your release, listening to all my orders, and not questioning me?”

Dan: “yes mistress, I am a sissy.”

Olivia: “good girl. Now, I made a custom dildo of Jack’s cock, just like my strap-on. You are to practice sucking and fucking this dildo every day. I expect you to be able to deep throat this in a week. And I want that ass to be nice and loose for Jack, so I expect you to be able to fuck that with ease in a week.”

Dan: “yes mistress.”

Olivia: “oh and don’t forget about your butt plug or bra and panties, you still need to wear them, everyday.”

Dan: “yes mistress.”

It was 7:45 as I walked out of Olivia’s, we had made it by 15 minutes. As I drove home, I wondered if Olivia was actually going to make me suck Jack’s cock. I would never admit it to her, but I desperately wanted too.

Part 6:

 

Back at school the following week, mistress was still checking that I was wearing my bra, panties, chastity cage, and butt plug. Aside from those checks, Monday and Tuesday went by as usual.

After school on Wednesday, I was walking out of the building towards my car. On the outside dash shield window of my car, was a pink sticky note, the note read:

“Hi sissy! Be at my house at 3. Pick up 2 French vanilla iced coffees. Walk into the house wearing the outfit that’s in the bag, in the front seat. Don’t be late. Mistress Olivia ❤️ “

I immediately started panicking, praying no one else read this note. As I frantically looked around hardly anyone was around me, and I took a sigh of relief. I got in my car and figured I’d wait to see what was in the bag, since it was probably something humiliating. I shuddered at the thought of potentially being spotted, holding a sissy outfit. I sped off, stopped at Starbucks, wondered why she wanted 2 ice coffees for a moment, and then was off to her house.

I pulled up to her house at 2:58, just in time I thought for a second. Until, I looked over into the passenger seat and saw the bag. I immediately started panicking at the punishment I was going to receive from mistress Olivia.

Inside the bag was an all pink, extremely slutty, maid custom. I took off my pants and purple bikini style panties first, and put on a pink thong, that was basically a G string, with very little protection in the front. Following the g string, I put on a very short pink frilly skirt. I removed my shirt and black bra, and put on a pink and white skin tight tank top. The outfit didn’t come with a bra, even on my skinny frail body, the tank top barely covered my nipples. The maid set was complete with a pink bow that I tied around my head, and sat just on the top of my head. Finally I put on white stockings, and bright pink heels. I quickly glanced at the time on my phone, 3:12, shit.

I opened the car door, and realized her garage door was closed, which meant I had to walk half way around the house to the front door. I momentarily considered going through the door in the back yard, but I thought this would make mistress Olivia mad, so I decided against it.

As I walked I could feel the wind against my ass cheeks, in a weird way I felt proud knowing that I’m just a slut showing off. I tried to walk quickly, but it was very difficult in these 6 inch heels. When I got to the door, I went to open it and it was locked! I immediately started panicking and frantically ringing the door bell. After 30 seconds or so mistress Olivia opened the door.

Olivia: “awww Sarah you look so pretty. The outfit I picked out for you looks perfect on you.”

Dan: (blushing) “thank you mistress Olivia.”

Olivia: “why don’t you turn around so I can see that cute little ass of yours?”

I spun around and bent over slightly so should get a full view of my ass, and she playfully slapped it.

Olivia: “Such a good little sissy slut. Alright let’s run upstairs, we’re going to have a lot of fun today.” Oh if only I knew just what I was in for.

Part 7:

 

Before I start this story let me describe some people in this story I have yet to introduce:

My biggest crush, Aubree: Aubree lived right down the street from me, and is in the same grade, so I have known her since I was a very young kid. Probably since 6th grade I have had a crush on her, while I have never told her this, I feel like she knows. Aubree stands 5’3” and weighs about 120 pounds. Has brownish reddish hair, with B cup tits, and a perfect ass. She is also a terrific athlete, and is even going to play soccer in college. She has the most innocent looking face, and looks like she wouldn’t hurt a fly. Like Olivia, she is very popular in school.

I opened the door to mistress Olivia’s room, and there was Aubree, sitting in Olivia’s room! I instinctively tried to turn around and run out but mistress Olivia had me trapped. Immediately Aubree roared in laughter as a walked in. While I was almost in tears.

Olivia: “Sarah, remember I said you were eventually going to meet some people dressed as Sarah.”

Dan: (nearly crying.) “But you never said they would people I actually know.”

Olivia: “This is all part of the process sissy, just trust me, don’t you think it’s better that I introduced you to someone you actually know first?”

Dan: “yes mistress I suppose you’re right.”

Aubree began walking up close to me, and was now standing beside Olivia, still snickering.

Olivia: “Now sissy, why don’t you greet Aubree.”

Dan: “umm hi mistress Aubree.”

Aubree: “no no that’s not how a proper sissy greats someone. A proper sissy does a curtesy like this.”

Both Aubree and Olivia curtseyed in front of me.

Aubree: “now you try, remember keep your back straight and bend your knees.”

I crossed my legs, bent my knees, and grabbed the edges of my skirt, as I tried to copy their curtesy. As I was doing this, without being instructed, I said.

Dan: “Hi mistress Aubree, I’m Sarah.”

Both mistress Olivia and Aubree roared in laughter once again.

Olivia: “Very good Sarah! Now when I introduce you to someone I expect you to do that.”

Dan: “yes mistress.”

Olivia: “okay now sissy, because you were 15 minutes late, it’s time for your punishment. Bend over my knee. Aubree you’re going to love this. Don’t forget to count sissy.”

I slowly bent over mistress Olivia’s knees, as she was sitting down.

WHACK

Dan: “one”

WHACK

Dan: “two”

This continued for 15 more slaps with Olivia and aubree alternating.

(As I’m still over mistress Olivia’s knee)

Aubree: “So you said you were going to introduce her to others, does anyone else know?”

Olivia: “well yes Jackie knows, my boyfriend Jack knows, and Julia, Meghan, and Nicole all know.”

I immediately stood up, with my eyes welling in tears. I started screaming at Olivia.

Dan: “YOU LIED TO ME. You told me nobody knew just a couple days ago. YOU PROMISED ME.”

I shoved Aubree out of the way, kicked my heels off and stormed downstairs. I sat in Olivia’s living room and began crying my eyes out. I didn’t what to do or what to think, I was broken and felt like I couldn’t trust anyone.

Olivia came by my side and hugged me, I let her hug me, as I continued to softly cry.

Olivia: “I’m so sorry Dan, I went way way overboard I shouldn’t have told all this people.

Dan: “you didn’t even ask me if you could do that, I trusted you, with my deepest secret, and you just went and told everyone.”

Olivia: “I know Dan that’s so fucked up and I’m so sorry. Look the truth is, I’ve had more fun with you, than I’ve had in a long time, you’re truly my best friend, and I love you, I truly love you.”

I continued to silently cry. I’ve never had a girl say anything close to that to me before, despite what she did, it felt good.

Olivia: “I think I went so overboard, because I truly view you as just one of my girlfriends. I want you to meet all my friends, so they can see how truly amazing you are, and why I love you so much.”

I suddenly stood up and lifted up my skirt, revealing my chastity cage.

Dan: “take it the fuck off. Right fucking now.”

As I said this I took the butt plug out of my ass, and threw it on the floor.

Olivia reached into her purse, pulled out the key and unlocked me. I didn’t say a word, walked out the garage door, got in my car and left.


Lucy Little

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