Tiny Dicked Sissy Stories

99,700 results
Orientation
Length
Source
Infinite Scroll

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...

A Visit From Her Bull

by humblebumble38 on Sep 17, 2017
Loving Wives

Today is the day. I have been cleaning all day. Ma'am has been soaking in the tub humming to Herself. W/we shopped for a new outfit last week and I have it laid out for Her on the bed. I want everything to be clean and inviting for Her Bull tonight. I don't know where She met him or any details really. All I know is She wants the house to be spotless. She wa...

My Sexuality Ch. 04

by TheOriginalAnonymous on Sep 13, 2017
Reviews & Essays

A blend of what I want in a relationship, my relatively unique brand of cuckolding - and the motivation behind why I want it that way - and how I wish there were more stories in erotica and in porn like that. It seems to me as if the cuckolding genre tends to be so narrow, the elements of it terribly lacking in creativity. Now, some people like the cliched...

Twist

by Seurat on Sep 12, 2017
BDSM

Once, long ago, I got fed up with the way femdom, forced transgender, and loving wife stories with BDSM basis ended; they had grown very predictable. In fact, a few authors had posted short lists of vignettes which, unintentionally, encompassed all of the common endings which I had grown to abhor. My own list, a response to the predictability of those storie...

Dominating Sugar Daddy

by LittleDickSissy on Jul 3, 2018
Erotic Couplings

The sissy cuckold was at the ATM withdrawing cash for his Mistress. He needed cash for her nails, her new dinner attire, and makeup. As he made his withdrawal his little dick dripped precum in his purple lace panties. He always got turned on every time his Mistress provided strict instructions to him, and of course whenever she played without him. "Now tell...

Jasmine Fucks My Wife

by cuntenslaver on Sep 12, 2017
Transsexuals & Crossdressers

Hello, my name is Tim. I am a 30 year-old married man. I have been married for five years to my wife Danielle. She is an absolute beauty of a woman. I remember when we were married, I felt like I was the luckiest man in the world. Since I am no hunk myself, standing at just five foot six and extremely lanky, I felt like I didn't deserve such a nice, gorgeous...

Letter from a Colleague Pt. 01

by 1Gratiano on Jul 15, 2020
Transgender & Crossdressers

Dearest Doctor Gratiano, I had been enjoying your communications immensely, and had often wondered how I might actively profit by your insights, when a quick peek at my husband's browser history made it immediately clear that he could be made into the perfect obedient husband — or perhaps I should say wife? Things really began to develop after he was laid...

Keith's Caught in a Costume Pt. 03

by gaildaniels84 on Dec 24, 2019
Transgender & Crossdressers

Keith's alarm went off and he silently reached out a hand and silenced it. He'd hardly been able to sleep at all, tossing and turning with worries about what school would be like today. It had been less than a day since his life had turned into a nightmare - his incredible teacher had caught him rubbing himself in a cheer uniform and then he'd had to buy pan...

Transforming Brent Pt. 02

by sissymissyct on Jul 10, 2019
Loving Wives

Kept in Loving Wives to annoy the tiny dicked anonymous reviewers that love to trash everything they read (after they wank to it). *** I woke up Sunday morning with a painful erection in my chastity and the pumps still attached to my breasts. I reached down trying to find a way to ease the pain in my penis. Nothing seemed to help. Maybe Wendy will be up so...

Turning the Tables Ch. 01

by Domma on Sep 17, 2017
BDSM

For so long we had played the game – I was the dominant Master, and she was my little sub slut. She was very good at her part, and I was even better at mine. She loved being forced, being used, becoming a wet hole purely for the pleasure and use of her beloved Master. I loved the power of making her do slutty things, and even more importantly making her WANT...