Sissy Punishment Wattpad Stories

36,771 results
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Infinite Scroll

The Story Collection

by Ulape2000 on Apr 22, 2025

Hello, this is Ulape2000 from wattpad, i switched to this website because it's easier to write in than wattpad, you can read all the stories i've written here, and i will be updating and the updates will be added along the way, so when i take a break from writing i will publish what i've written even if it's not done. https://www.wattpad.com/user/Ulape2000Wh...

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So I'm Not a Vampire? Ch. 00

by sensanin on Sep 14, 2017
NonHuman

Hey Everyone, So this is the completely edited version of So, I'm Not a Vampire? I decided to post it on lit because I realized not posting my stories really solves nothing. Having them remove one of my stories was the first and only bad thing that's happened to me on lit. Am I angry? Yeah, but life goes on. And plus lit fans are way too awesome to leave....

BOMBS + BEAUTIES

by TheSpectator on Apr 29, 2025

January 1st, 1901, to December 31, 2000…Also known as the first century. A lot has happened during this time period—a couple of world wars, a lot of battles in-between those “silent” periods. No biggie, though. Welcome to the Long Peace. Luckily(?), the last two decades have allowed a side of people to come out and show what they fantasize about. The interne...

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Bitte lasst mich kommen

by Kitten_Mixed on Apr 22, 2025

Kleiner Einschub, wegen Plagiat. Ich habe diese Geschichte bereits schonmal auf Wattpad veröffentlicht. Langsam öffne ich die Augen und angel nach dem nervtötenden Ding das sich Wecker schimpft. Während ich versuche mich daran zu erinnern aus welchem schönen Traum ich gerissen wurde setze ich mich auf und reibe mir den Schlaf aus den Augen. Noch etwas versch...

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Sissy Chantel, New Reality Ch. 10

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Ten: My First Saturday and Sunday as They are Special Days For Us. "Wake up girls." as sissy Traci calls out to us. We all rise from our sleep and another day in our sissy maids, sissy sluts lives begins. Just like in the previous days starts we spend our time with a morning enema, shower, shave and makeup. We get dressed but not in any maids out...

Sissy Gets Punished

by MsMorrigan on Sep 16, 2017
BDSM

Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...

Sissy's Shopping Trip Pt. 01

by SissyFaye on Jul 13, 2020
Transgender & Crossdressers

"You finally got paid, Sissy!" my mistress says with excitement. "Yes, I did, my love," I say. "Well, I think in celebration of your first paycheck from this new job, we need to go shopping!" she says. "Oh really, shopping for what? I ask. "Clothes for me, and maybe some for you," she says. "Mmm, sounds like fun!" I say with excitement getting hard...

Becoming a Sissy Maid & Slut Vol. 08

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Fourteen: Chantel Learns a Lesson. Another bright and early morning for me. Another busy day ahead as a sissy maid and later on as a slut. What plans Master has for me as a sissy slut tonight, I don't know, but I'm sure it will be exciting, with lots of creamy cum for me to taste and swallow as well as good for hard core butt fucking. I'm already ge...

My Mistress is My Wife Ch. 02

by slavetohiswife on Sep 14, 2017
Fetish

I'd spent what seemed like forever locked away in my cock cage, looking at and downloading porn for Mistress while she slept. I felt like the slightest touch to my cock would cause me to explode. I had tried and tried to touch myself the whole time but the cage more than served it and Mistresses purposes. I was only able to get so hard and my balls ached. I...

The Session

by davemacc65 on Sep 16, 2017
Transsexuals & Crossdressers

I arrive at the door of the hotel room, at the stated time. My feelings were mixed. Nervous, meeting you for the first time and excitement knowing that I would be in control of the situation, well at least for the moment. Just before the door opens I realise I will not recognise you! The only pictures I have seen of you, you are wearing a hood! The door open...