Sissy Milk Stories

38,319 results
Orientation
Length
Source
Infinite Scroll

Emery and Alice

by fantaseeboy on Jan 27, 2020
Transgender & Crossdressers

When my uncle, my only living relative, passed away in his sleep from an aneurysm, I returned to settle his estate. I hadn't been in that part of the country for nearly a decade. I had been in middle school when my mother passed and I was forced to move in with my aunt on the opposite coast. My uncle had always been the oddball of my mother's family. But he...

Sissy Dust Pt. 03

by Sissyhalo on Sep 11, 2018
Transsexuals & Crossdressers

*Before... I lose track of everything after he seeds my insides and kept going. No not everything. Three highs after the mixture entry affected me. Three times Steven came inside of me. I dimly remember the clock. And my body in some sort of perfect fuck shock after he was done and shaking with him vibrating too our hearts pounding after that and him s...

Discovering Mistress Sarah's World Pt. 04

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

Special thanks to Mistress Sarah and Miss May and Miss Mill who are my motivation for this story. Thank you for your guidance and wisdom and for the privilege of serving you and writing about you. Chapter 11 Discovering the Girl in Him For the first time since he arrived at Mistress Sarah's house, Josie was left alone in silence. His cock was still thro...

Sammi Meets Teddy

by Sissy_Sammi_ on Dec 8, 2017
Transsexuals & Crossdressers

Ever since Sammi was born Sam had been working his ass off, both in pants and panties. His grades in school improved rapidly as his outlook on life improved, and before he knew it he had sent away college applications and received acceptance letters. He knew where he was going to college, and before he knew it he was graduating. The rest of the year coasted...

His Sissy Boy

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

by a kept sissy As directed, he was waiting for me when I returned home. Seeing him in blouse, skirt, stockings and heels, makeup perfectly done, manicured and painted nails (he does them every morning after his household chores, for the evening ahead), seeing his very sexy hair style, hint of nice perfume, it's hard to tell he's not a real woman. And the b...

Daddy's Little 'Girl'

by keptsissy on Sep 16, 2017
Transsexuals & Crossdressers

The noises he makes, the sound of it all, it's my favorite part. I love the feel of him in my hand but to hear him moan, grunt, make all the 'man sounds' men make when they are being driven sexually crazy makes my little thing wet. The slippery sound of him sliding back and forth through my hand, I love all of it. Masturbating him is one of the most erotic...

Keeping My Sissy Secret

by VrijeVogel on Apr 24, 2019
Transgender & Crossdressers

YES! She really won't be home! I thought to myself as I cycled towards my house. My mother's car was missing from the driveway, meaning her plans for visiting a distant aunt hadn't been cancelled after all. Her wardrobe would be all mine for the entire weekend and I couldn't wait to try on her clothes. Aside from everyday clothes fit for a single mom, there...

Sissy Downfall Ch. 02

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Revised version. all characters are adults. Part two. All Characters are over 18. * My new life at Mistresses mansion was quite pleasant most of the time. My duties were to be maid to the two mistresses. I helped them bathe and dress; hand washed their delicate garments, cleaned their bedroom and changed the bed clothes daily. Sometimes, if I was really...

Ugly Duckling to Sissy Princess Ch. 06

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

I was terrified, yet part of me was aroused to have such beautiful girl and gurl touching my body. It felt as if they were preparing my body for a sacrifice. Vanessa and Bernice seemed to want to sync their attacks. I could feel the tip of Vanessa's cock at my back door and the tip of Bernice's strap-on cock on my lips. I looked straight into Bernice's eye...

Hot Midwest Summer Pt. 01

by OrientZion on May 22, 2018
Loving Wives

These stories are actual accounts of our adventures and all parties listed are of consenting and legal age. Names have been changed for privacy but the subject matter remains factual. We are NOT professional writers and we do not claim to be so we are also still looking for an individual to help us edit our stories if you are interested, reach out to us. We...