Headmistress Stories

651 results
Orientation
Length
Source
Infinite Scroll

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 Girl or the Group? Ch. 02

by gorson on Sep 14, 2020
Group Sex

Lucky Stiff My arms held a beautiful, naked woman. She was kissing me passionately, desperately even, and rubbing her body against me. That long, lithe, voluptuous body I'd lusted after earlier. Large, firm breasts. Taut, shapely legs. Slim waist. I kissed her back, hard, responding to the challenge of her, our tongues twisting against each other. For a lon...

My Friend Sophie Ch. 02

by LeanneSinclair on Sep 17, 2017
BDSM

In the previous story I introduced you to my lovely friend Sophie and told you about an evening when she and I got very drunk and she told me, in great and explicit detail, about her submissive fantasies and desires, which were focused on her male boss. I'll pick up the story again on the morning after that, briefly, although I'll probably then gloss over so...

Long Road to Find a Heart

by Egmont0409 on Sep 19, 2017
Romance

CHAPTER 1 Three months after high school graduation Amy Wishart lost her virginity, willingly, at a party at a friend's home. Thomas Curtis, known by his buddies as Tom Cur, or simply as Mongrel when nicknames were used, performed the deed with reasonable skill and minimal discomfort to end Amy's growing fear she might suffer ignominy by becoming an adult v...

Art Deco Pt. 01

by Sputnik57 on Sep 14, 2017
BDSM

Synopsis: 'Publish and be damned!' Said the Duke of Wellington, though this was in respect to blackmail; publish the truth about how you feel and you may find yourself living out those feelings as well by those who would wish to control you! This is a tale of a man finding courage to admit his desires and being 'brought to book' by lusty females in a sunshin...

Surrogate Ch. 02

by Vandemonium1 on Sep 11, 2017
Loving Wives

byMattblackUK© and Vandemonium1 Way back in the mists of 2012 MattblackUK wrote a fine story called 'Surrogate'. Half way through reading it I thought it was going to take a different track than the one it did. Recently I approached Matt and he gave me his kind permission to change the ending. The start of the story below is Matt's work 100%. I have indicat...

Finishing School for Shemales

by Imogen_TS_2020 on Sep 25, 2017
Transsexuals & Crossdressers

Mistress K looked at the school report and smiled. She wouldn't describe herself as an evil bitch, but plenty had. She was proud of her position. Headmistress of the Finishing School for TGirls. So many beautiful shemale girls had left her careful administration and gone on to happy lives, or sometimes porn careers. Sometimes they had been bought outrigh...

Man's Best Friend Ch. 03

by RavenKrow45 on Sep 17, 2017
Erotic Couplings

"Level of passion you say William, Aye." Would that level be the same as when - with your, ballerina Hmmm?" She placed her greasy thumb in her mouth, making sure I saw it, and smirked as I looked down at her; "Fishing for another compliment huh?" Okay, you're certainly right up there." Kate glared at me; I did nothing to play down her response by adding; "...

Surrogate

by MattblackUK on Sep 15, 2017
Loving Wives

Chapter 1 He'd had that dream again, last night. He somehow knew he was near water and he could hear two people laughing at him. It was such a vague, silly dream that he had not thought to mention it to anyone, not even his wife... *** They were already a good part of the way to their destination, when Derrick's Satnav flashed up an alert. He glanced at...

Colin's Chronicle

by Macjay on Sep 17, 2017
Fetish

Clearly, Great-Uncle Colin had loved to write which was not so surprising when one considered that, when diagnosed with an inoperable brain tumor, he was the managing editor of a national newspaper on Fleet Street. The end, when it came, was quick and painless and later his will revealed that he had left all his personal papers to me. There were drafts of t...