Sissy Surgery Stories

14,633 results
Orientation
Length
Source
Infinite Scroll

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

Influential Factors! Ch. 02

by gummidurango60 on Sep 12, 2017
Transsexuals & Crossdressers

The alarm rang and I woke tired, thoughts of last night put a smile on my face. Finally, I don't have to hide my cross-dressing from Jill any longer. I jumped out of bed, took a shower, and toweled off quickly. When I reentered the bedroom I noticed Jill had laid out some clothes for me on the bed with a note. It read, "Prepare for a day of fun!" I had...

The Beach Trip

by wifestoy on Sep 13, 2017
Transsexuals & Crossdressers

We were saying good-bye to the boys and readying for our beach trip. Renee was going to explain the facts of life to Ms. Anastasia Elizabeth Messier. Good bad or indifferent the rules and life plans were going to be laid out in this chapter. We were getting ready to explore another side of our growing relationship. We will be enjoying some well-deserved time...

Cop Town Girl Ch. 01

by MicheleNylons on May 7, 2019
Transgender & Crossdressers

Chapter One - Penelope Penelope Bishop gripped the steering wheel so hard that her hands were beginning to cramp. She stared intently at the tunnel of light made by the headlights; the road was sealed but unmarked except for the reflectors nailed to the white posts spaced sporadically along the side of the road. The night was pitch-black and the road was da...

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...

TS Princess Ch. 01: Fucked by My Warden

by TSPRINCESS on Sep 16, 2017
Transsexuals & Crossdressers

It had been several weeks since I left home with my cousin brother for my breast-enhancement surgery. All our family knew was that I was going to some cram-school to get coaching for Pre-Medical Exam (AIPMT). My cousin brother had been supportive of me not only since he cared for me; it was due to his own advantage of having a full-formed girl at his disposa...

Girl with Something Extra Ch. 06

by JonThomas_ on Oct 15, 2017
Transsexuals & Crossdressers

Author's note; There is no sex in this chapter. I hope that's OK. ~ Hello readers, this is your humble omniscient narrator with another episode in the life of Daisy; The girl with something extra. When Daisy Elaine Maye was a fourteen year old boy named David, her hairless body began to develop curves and breasts. Over the next four years she developed in...

Carrigan's Kinks

by Scotsdude on Sep 15, 2017
Fetish

To those who have written to me asking to write again, I dedicate this story. It's been a while since I submitted a story to Literotica and a lot has gone on in my life since then...one divorce and one marriage. I do intend to submit some more stories over the coming months, including the long awaited sequel to Zius...I know promises, promises, but it is alm...

Danielle Works a Saturday

by CDDanielleNNJ on Sep 16, 2017
Transsexuals & Crossdressers

DISCLAIMER: This story involves sexual situations between one or more cross-dressers or adult males. If this offends you, please leave. Otherwise, please enjoy this fantasy of mine. Please post wherever you feel and share with your friends and loved ones. All I ask is that my e-mail address remain in place, as I am the sole creator/author of this work. All c...

From a Husband to a Dutiful Sissy Ch. 16

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Sixteen: Chantel's Personal Medical Journey and we see True Love and Emotions. ***** [Please note the following: My readers, I am injecting this note here as I will be writing about Chantel's events just before, during and post her vaginoplasty. I will make clear here, I am not a doctor, my writing here is not meant to be 100% accurate or clear as...