Sorority Sissy Stories

10,264 results
Orientation
Length
Source
Infinite Scroll

Katelyn's New Sissy Pt. 01

by bluesbirds on Dec 25, 2018
Transgender & Crossdressers

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors a...

Sissy to Military School Pt. 04

by Tranylvr on Dec 2, 2019
Transgender & Crossdressers

The continuing story of Sissy Steffi at military school. If you haven't read the previous chapters, please do for context and back story. All characters in this story are of legal age. This story depicts the explicit erotica of a transgender nature. If this material is offensive to you; or forbidden in your area, or you are a minor, please stop reading! All...

Doll House - The Salon Pt. 02

by Dani_Doll on Sep 19, 2017
Transsexuals & Crossdressers

I stepped out of the tub, feeling curiously invigorated after a thorough washing from Miss Hunter. Exploring my chest and front, I was surprised to see that the cuts she had inflicted were already partially healed up. I couldn't help but notice the silky smoothness of my own skin as I inspected the wounds... I had never felt so soft before! In fact, my skin...

House-Sitting Panty Lover Pt. 01

by sissydn on Sep 15, 2017
Transsexuals & Crossdressers

Finally Friday! The day I have been waiting for, for so long. A month ago my sweet and hot neighbours, Megan and Sophie, knocked on my door and asked if I would watch their house and feed their dog when they left for an extended weekend. I immediately replied yes and suggested I could do some house chores since I had no plans that weekend and were low on m...

From a Husband to a Dutiful Sissy Ch. 08

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Readers, I so hope you are enjoying my story here. It sort of allows me to live vicariously through my words as Chantel. This story has been outlined to allow me to write it in an encompassing and linear way. I try not to wing it but to paint a story that is life-like without being boring, well at least I hope it's not. I hope my characters are believable an...

Girl's Night Pt. 03

by DifferentBreed on Sep 14, 2017
Fetish

Fisher climbed the stairs slowly, wary of the quiet that hung over the upstairs. As he hit the landing a soft moan emanated from the bedroom and his heart raced as he entered the doorway. There, framed in the soft light of the bedroom lamps, was Sophie kissing another woman. Her crisp white shirt was unbuttoned, exposing the top of her supple breasts, and gi...

PIXIE Sissy Stripper Ch. 04

by EROTICbearscribe on Jan 20, 2020
Transgender & Crossdressers

Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS. ***** THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...

Throne of Panties Ch. 02

by scur on Sep 16, 2017
Fetish

This story continues where "Throne of Panties" left off. A man made the mistake of allowing a stewardess to see him in panties and stockings and instead of getting a blowjob he was pushed to the ground and now another passenger becomes involved. I think both stories would benefit from being read in order. ***** "Oh really." the other passenger said. "Does...

Goldenrod Prequel

by rlmmike on Sep 15, 2017
Fetish

I'm writing this for the sake of the Order, so that should a threat like the one depicted emerge again, we may have some means of recognizing and defeating it. This account is factual to the extent possible, with sensitive information changed or omitted insofar as doing so would not alter the overall meaning. I appear as a character below, so further data ab...

Chronicles of Danny Ch. 04

by bbettyblambabam on Sep 15, 2017
Exhibitionist & Voyeur

Danny and Ashley met with Natasha at lunch the next day. When Natasha saw the two of them walking together she raised an eyebrow and gave a wry grin. "Sooo...did you two have a good night?" Ashley lowered her eyes and smiled while Danny said, "Yeah I guess you could say that." The two of them sat down and started to eat. "I heard Taryn got kicked out of ch...