Sissy Dicklit Stories

1,000 results
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Infinite Scroll

Robin and Jimmy Olsen - Sissies Ch. 06

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

"Miss Robin! Surely you can't be serious!" "Introduce us, Alfred! Just like any other guest arriving, we deserve to be introduced to the crowd!" demanded the lovely sissy! Robin and Jamie were dressed in very attractive summer dresses - Robin in blue and Jamie in green which accentuated his green eyes and emphasized his bright red hair! The dresses would ha...

A Roleplay Gone Awry

by ronald81 on Sep 15, 2017
BDSM

All people within this story are over the age of 18. ***** For as long as I can remember, I have always been into cross-dressing as a young boy. Yet, I would hide these feelings deep down as I grew up. The following story is partly true, as much as I can remember. It all started when I was playing a roleplaying game featuring a text based game that was su...

The Secret of the Island Pt. 04

by neoview on Oct 30, 2018
Sci-Fi & Fantasy

You thought the story had died but it was just my lazy ass refusing to continue. Also I was busy with my girlfriend so I couldn't really focus. Yes, I have a girlfriend now. Well "she" prefers to be called a girl even if she isn't. Without her I would finish this story much faster, but... she gave me some interesting ideas which were too good to ignore. ***...

Derby Line Marriage Ch. 16

by jtuf on Sep 15, 2017
Loving Wives

"TANSTAAFL" "What?" Francis asked into the phone. Despite being fluently bilingual, she had never heard of the word that Benjamin had just used. It must have been and Americanism. "Never mind. It's just an expression. So, what favor do you need?" Benjamin replied. Francis hesitated. She was not quite ready to spring her request. "It's a bit personal. I'l...

Sissy Stretching for Princess T Pt. 02

by Subboi23 on May 12, 2020
Fetish

Once I get home, I practically run to my room. Sitting in the car has pressed my plug deep into my ass and now my running causes it to wiggle around while still deep inside me. "Home Princess," I text as soon as I close and lock the door to my room. I quickly peel all my clothes off except for my panties and get on my knees. My toy is retrieved from a draw...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

Sissy Prince: Origin Ch. 01

by SatinSlip on Feb 6, 2018
Fetish

Prince Oliver skipped through the castle garden. He loved the green and the flowers. He was nineteen and yet to be married. In truth his parents had coddled him as a boy. He knew his numbers and letters. He knew how to run a castle and a kingdom. On paper anyway. But he would never be a warlord. Never be a brave leader of men on the battlefield. His gold...

A Sissy Girl Bitch, 'BEST IN SHOW'

by keptsissy on Mar 3, 2020
Fetish

** Author's note: All characters depicted in this story are fictional, well beyond age-of-consent, and are consenting adults. ********************************* He made a point of showing me off, displaying me. That was obviously his thing from the start. Many men at the clubs he'd take me to were allowed to not only look but touch me too. I never thought a...

Courtesan Ch. 16

by Goodhusband on Sep 19, 2017
Loving Wives

This is the sixteenth episode in a series entitled "Courtesan". If you have not read the previous fifteen episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alternative...

Steph's Descent Ch. 09

by 62_goo on Aug 31, 2017
Fetish

Steph woke up and looked at the sleeping form next to her. Her first thought was of her husband, Phil. But a split second after that thought entered her head she realised that it was Amanda her girlfriend sleeping next to her. She thought about how much in love with Amanda she was and also of the situation she found herself in. It had started when she was f...