Sissy Academy Stories

10,735 results
Orientation
Length
Source
Infinite Scroll

New Jack Ch. 03-04

by deviantradoddness on May 8, 2018
Group Sex

Feedback and constructive criticism are most welcome! 3. Monday morning dawned to find Jack already on the road, his sneakers beating a steady staccato onto the wet pavement. He had pushed on this run, still keeping the distance at a respectable three miles but working to drive his mile time down. He idly wondered why no one else around here was out joggi...

What a Mess

by Blue88 on Sep 16, 2017
Loving Wives

It was a beautiful fall evening. The sun had just started to dip below the horizon and there was a warm glow that pervaded the area...but, there seemed to be waves of angst emanating from 77 Wistful Vista Lane. Was all not right with the family that resided there? Marty Kramer sat back from the table, a smile of contentment on his puss, and patted his st...

Patty's Punishment Party

by fmcchris on Sep 14, 2017
Celebrities & Fan Fiction

"Oh, my God!" Meg Ryan uttered as she and Marisa Tomei watched in stunned disbelief while John Weston, Patricia Heaton's personal assistant for the past two years, assiduously stroked his huge cock in front of a stack of recently produced color photos of his boss, which showcased the red-headed beauty in an assortment of sexy dresses and which now lay in pel...

The Sexual Adventure Pt. 08-11

by bankshot1993 on Sep 16, 2017
Loving Wives

Once again fair warning for those about to read. This installment has act of bisexuality/homosexuality, group sex as well as humiliation and people that go outside their marriages for sexual contact. If you are uncomfortable with this subject matter please find something else to read (after all this is the loving wives section). Reading this and then protest...

From Jenny to Mei Ch. 28

by asianToy on Sep 14, 2017
Novels and Novellas

Ai watched Mei arise out of the big bed from the corners of drowsy eyes. She lay with Philip's forearm on the outside of her thigh, his fingers dangling near her groin. 'Poor girl,' she thought, envisioning Mei kneeling in front of a white-haired, lab-coated doctor, his huge penis dangling at her chin. 'Poor confused girl.' She pictured little bubbles wi...

Flowers for Jill Ch. 04

by Ginger_Martin on Sep 14, 2017
Erotic Couplings

Author's Note: I enjoyed and appreciated all the feedback sent to me, and I bow in humility to everyone that took the time to shoot me an email about my work. I take all critiques and suggestions in mind when I'm writing, and I encourage you to send me your opinions, and be as detailed as you'd like to be. I had to cut this chapter in half, for it was...

Blondie Balls My Black Boss

by raven2222 on Sep 13, 2017
Interracial Love

Two years or so after my sexy little blond wife got her first taste of the special eroticism of interracial sex, a significant new turn of events began when my boss flew down south from Chicago to spend some time working with me. I had an idea that the real purpose of his trip was to have an excuse to visit his aunt, which he pronounced ‘awnt’ in his hometow...

Reesa

by Lost_Yonder on Sep 15, 2017
Interracial Love

"'The Washintonian's' Most Eligible Bachelor in DC certainly didn't smile much as a kid, must have been because you were so accident prone. How many different bones did you break?" "Why are you looking at my photo album? Is The Post now going to do a story on my childhood?" "No, come on, let me look, we've been dating for almost two months now and I know n...

TNQF Slightly Secret Six & A Half

by pop_54 on Sep 17, 2017
Celebrities & Fan Fiction

The not quite famous slightly secret six and a half: By pop_54/2003. With acknowledgement to the marvellous Enid Blyton for the inspiration for this small attempt at an 'adult parody' of a children's story based loosely around the style of children's novels written by EB. I must add at this point that any childlike mannerisms associated with the character...

At Her Command

by creepyrj on Sep 15, 2017
Transsexuals & Crossdressers

So at last my newest creation. If you are familiar with the Becoming the Dominus series, you will recognize some people from here. I have to thank my editor Kira for being awesome. As always enjoy the story and vote and comment on it. Enjoy the show and maybe I'll have a part 2 if you enjoy it. * The paper was done and she marveled at it. The hard work an...