Tiny Dicked Sissy Stories

99,700 results
Orientation
Length
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Infinite Scroll

Being Jenny's Summer Boyfriend Ch. 03

by Lucas96 on Jan 21, 2020
Fetish

Disclaimer: this story involves cuckolding, humiliation, cross-dressing, and gay incest. *** I have to admit, it was difficult to contain my excitement as Jenny invited my dad and brother over to show them what a little sissy slut I'd become. To prepare, Jenny let me try on the outfit she'd had on when we'd come over to Andrew's house: a pink, tight-fitt...

A Sissy Saga Ch. 02

by Snurge on Sep 15, 2017
Novels and Novellas

When Jennifer went out onto the terrace William was nervous but relieved to be with someone his own age and gender, even if that person had been sissified just like himself. The two eighteen-year-olds regarded each other and their feminine attire silently for a moment before Archie at last broke the tongue-tied awkwardness. "Better make a start," he said,...

The Good Wife Ch. 03

by tazsis1 on Sep 15, 2017
Fetish

[Part three of a series of stories about a wife who owns her husband. I get a lot of abuse from some readers who seem to think I am committing an unforgivable crime and personally insulting them by putting these stories in what they think is the wrong category. (I like a bit of abuse, but mostly from my lovely wife.) These stories have elements of fetish and...

The Chastity Trap Ch. 01

by slavemalcom on Nov 23, 2017
BDSM

Malcom trudged out of the exam hall with the other students and sighed in relief, it was finally all over. He had just completed the final exam of his degree and could do nothing about the outcome now apart from wait and hope. He walked over to a group of his 'friends' who greeted him with high fives and cheers as they all stood around and dissected the exa...

March Madness Ch. 09b

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

A Sissy's New Daddy Ch. 02

by sissyneko on Oct 8, 2019
Transgender & Crossdressers

I hope you enjoy this second installment of 'A Sissy's New Daddy'. I worked hard on it and hope that it brings all of you the same pleasure reading it that it has brought me writing it. There are some extreme moments in this chapter but also some very tender ones. There was a line in the first piece that gets expanded on at the end. I hope you enjoy what I h...

The Sexy Cuckold Couple Pt. 11

by cuckcpl4play on Sep 19, 2017
Fetish

This is part 11 of the series and it is about the fantasy we have as a cuckold couple. We have engaged in many acts of cuckoldry, but the story itself is fiction. If you are offended by this type of lifestyle than please don't read. It amazes me that we continue to get such negative comments to this series from people claiming that we are uneducated or despi...

Topped from the Bottom Ch. 06

by cutebabysadie on Sep 14, 2017
Fetish

Topped from the Bottom - Chapter 6 Summary of previous chapters: Chapter 1: Todd, college football quarterback and alpha jock make a bet with his short nerdy vocal music roommate, Mark. The bet was that Mark could fuck Samantha, Todd's girlfriend, better than Todd. To be more specific in just 10 minutes she would be orgasming and screaming Mark's name. It...

Why I’ll Never Go Sharking Again Ch. 02

by tsfan84 on Sep 13, 2017
Transsexuals & Crossdressers

Earlier today, I was raped by a shemale. It was my first sexual experience with anyone not carrying two X chromosomes. It hurt like hell, at first and to be totally honest, I'm still sore. But it also felt really good after a while. The sensation of being.....what's the word I'm looking for here..."filled," while cumming is the best. Having your ass clench d...

Mistress Treva Wins Again

by justincbenedict on May 29, 2018
BDSM

Dr. Shepherdson Grangerford milled about at the fundraiser, his adoring wife, Treva by him, the ultimate arm candy even after all these years. A balding, chubby fellow came up, grabbing Shep's hand. "Dr. Grangerford, everyone is so pleased that you made the fundraiser, and that you'll be heading up the Ophthalmological Wing. We probably couldn't have gotten...