Trans Surprise Stories

136,543 results
Orientation
Length
Source
Infinite Scroll

Ms. Greys' School Ch. 01

by Lydyia on Sep 15, 2017
Transsexuals & Crossdressers

written LJP edited another wannabe Preface:This school is for young women(18-20) and is focused on helping young trans women with their transition. Also I would like to thank my Editor for all his help. * It was already a long day and it was only 10 am. "I must discuss hiring more girls with Ms. Green tonight," Shelby exhaled. Ms. Grey's school for yo...

Trans Dork Love

by PrettyJana on Sep 16, 2017
Transsexuals & Crossdressers

He pulls my shirt down with his teeth; he’s cute like that. I smile at him as my breasts come free. “Love ya’ sexy babe,” I tell him. He winks and goes back to work. I look over at his shirt carelessly tossed to the floor and then back to him, his smooth chest, god, so sexy, I love it. His pecks stand out subtly and I feel the smooth bumps and dips that...

My Transgender Neighbor

by Lara_Longstaff on Sep 25, 2017
Transsexuals & Crossdressers

** Disclaimer! Like a lot of my stories this one features a girl with really a large endowment, and through the course of the story, she learns that she likes being "on top" best, perhaps even exclusively. Not everyone likes that kind of arrangement so I thought I'd give everyone a 'heads up'! Also, there's some discussion of politics surrounding transgender...

Delilah

by jezzaz on Mar 18, 2020
Transgender & Crossdressers

So, this was supposed to be for the 750 word project, but a) I was traveling and just didn't get time to edit and refine it and b) I couldn't get it down to 750 words anyway, no matter how I tried. So, 862 words instead. Just something that came up and I had to dash down. * What kind of author is late for his own challenge? Tsk tsk. Hi. I'm Delilah. Hope...

Welcome to the Party

by Sweetlisatv on Sep 14, 2017
Transsexuals & Crossdressers

Over the years I had dressed I had many experiences with guys, couples and dipped in and out of the Bdsm and fetish scene as I felt like but it wasn't until I was invited to a private interview I really got involved. It was a sunny Tuesday morning and as I awoke in my favourite purple satin baby doll and panties I felt the need to play so going online I sea...

Lonely in Berlin

by Alex_Lockheed on Jun 1, 2020
Transgender & Crossdressers

Note: This story is a transgender erotic romance involving a dominant male and a shy, but very dirty, submissive t-girl. It's relatively long, it's a slow burner, and it's emotionally involved. It's told from the t-girl perspective. It is not a quick jerk-off story; however, if you're willing to embark on the journey, it gets filthy towards the end. If you'...

A trans threesome Pt. 02

by mrtranstastic310 on Jul 15, 2020
Transgender & Crossdressers

Author's Note: This is a continuation of A Trans Threesome, but can be read separately. Please leave any feedback, critiques, or comments! As a reminder, this story does contain words often thought of as "feminine" to refer to a transmale's genitalia. Enjoy! --- J's single finger probed at me, hesitant, but finding my entrance slick enough to enter without...

A Night at Paris

by MegWrites on Oct 19, 2020
Transgender & Crossdressers

An Afternoon in Paris All morning I have been thinking about making the 45-minute drive to Paris Theater for some desperately needed debauchery. Sure, it is winter and will probably snow but then again maybe it will not, my need for sex wins out (like it ever loses). I leave around 2:00 in the afternoon for the Theater and 30 minutes into my drive it starts...

Buck in rut

by maxxwood69 on Jan 20, 2020
Sci-Fi & Fantasy

NOTE: This is a story about anthropomorphic characters, i.e., furries, during mating season. This story also includes a cis man having sex with a trans man and impregnation. ### No matter the season, this was Buck's favorite part of the day - he had just clocked out of his office job, and now he was walking home. It was a long walk, but Buck loved the tim...

Katherine's Choice Ch. 02

by grover10 on Sep 14, 2017
Celebrities & Fan Fiction

(Celebrity, Pornstar, Transsexual, Seduction) (Copyright) Mainstream celebrity character suggested by another Literotica member. Main characters: Katherine Heigl, Jessy Dubai * Katherine stepped out of the shower and dried herself off. She hung up the wet towel on the back of the bathroom door. Katherine opened the door and stepped out into her hotel roo...