Shemale Surprise Stories

136,276 results
Orientation
Length
Source
Infinite Scroll

Debbie

by Excalibur_1949 on Sep 15, 2017
BDSM

Debbie wasn't the best looking girl in the office. In fact, the waste bin looked more attractive. But there was something about her that I couldn't put my finger on. She was hard working. She often stayed behind when everyone else left. Never did I have to chase her up over a project. Her dead lines were always met easily. In truth, she was about five, fiv...

Dangerous Games

by Many Feathers on Sep 16, 2017
Exhibitionist & Voyeur

At forty-two years of age, Jackie Anderson was an attractive looking brunette that looked more like a woman in her early thirties. She still wore her hair long, usually in a ponytail that helped to make her look younger as well, which probably helped to contribute to her being mistaken for a much younger woman. She worked out, though not as often as she woul...

The Meeting Ch. 02

by SoNaughty on Aug 30, 2017
Group Sex

Robin It has been a few days since Sherye and I shared that wonderful night together. I have been wanting to call her, but was not sure if I should. I have never been with a married woman before and I think that is what has been the cause of my reluctance to call her. The problem is that I can not seem to get her out of my mind. I keep thinking of the marve...

Life After Love Ch. 02

by bluedragonauthor on Sep 14, 2017
Group Sex

PART 2: Reality *** Saya and I had shared a beautiful weekend. Now the real world waited. Walking out the door, I couldn't think of anyone else I wanted at my side. My life after love had begun. But when I said that the real world waited, I meant reality would be shattering my fantasy world. From the moment we walked into the building together, our profes...

Born to Be Ch. 07

by DamienDeath20 on Jun 8, 2020
Transgender & Crossdressers

A.N. Return to the strap on! If this isn't my favorite chapter so far, it's definitely one of my favorites x))) Buuuut chapter 8 is preeeetty awesome too ;D I know I'm a whore. The Following Contains: Interracial between a tall black lady and a crossdressing femboy. Which in conclusion creates a formula of strap on penis being inserted into femboy bott...

Escalating Series of Surprises Ch. 02

by YKN4949 on Aug 24, 2020
Transgender & Crossdressers

Hello Readers! This is Part Two of a Two-Part story. Both parts are written and have been posted in order. Chapter 2: Bigger Surprises "G'damnit woman, I get home from a hard day down at the education manufactory, I missed the omnibus..." "There is no 'bus from Arnoldsville," I interrupted, stepping aside so that Sabrina could come through the door. She...

Possessing Bella Ch. 23

by xelliebabex on Sep 26, 2017
BDSM

Authors Note: Due to the timing of the completion of this series, this chapter has not, as yet, been through the careful hands of my wonderful proof-reader and friend AisieLynn. I will endeavour to replace it as she has time to work on it for me. I hope you will forgive my eagerness to bring you the conclusion to this long running series and bear with the fe...

The Party

by Many Feathers on Sep 12, 2017
Group Sex

The Party Author's note: From time to time I entertain ideas or suggestions from some of my readers and fans. A while back, I was approached by a couple who had attended a rather wild party. They asked if I couldn't put into words for them, some of the things they did and experienced. As they have also asked to remain anonymous, I will honor that request. T...

Accidental Summoning Ch. 04

by Mr_Shoggoth on Mar 27, 2018
Sci-Fi & Fantasy

Author's Notes: This story contains the following: Anal, Hermaphrodite, Demons, (Mild) Mind Control, Fantasy, Fellatio, Femdom, a little Bondage and some Romance. __________________________________________________________ Hamid Abedi's first clue that something had gone seriously wrong was the headache he felt as he clawed his way back up to consciousness....

The Book of David Ch. 05

by bluedragonauthor on Sep 12, 2017
Group Sex

*** -- CHAPTER 5: The Sisters -- *** FALL QUARTER, JUNIOR YEAR (September 2000) Friends. I could handle being friends. For some reason, having sex with E-Beth gave me closure with her. I'd subconsciously spent the entire summer with her in the back of my head, wondering how we would act around her when we met up again at school. Now I knew. And I knew...