Black Cock Sissy Stories

312,295 results
Orientation
Length
Source
Infinite Scroll

Chrissy the Sissy

by Ide32 on Sep 14, 2017
Transsexuals & Crossdressers

Part 1 The Bank Job Chris or Chrissy as he calls himself has the job of his dreams, he works at a sperm bank for futas. His job is to dispose of samples that are non-viable, low sperm count etc. All day long he dreams about the creamy, yummy cum from futas waiting for him to dispose of it. While he is supposed to put it down the sink, he has a preferred met...

A Picture Perfect Sissy

by meeah sue on Sep 16, 2017
Transsexuals & Crossdressers

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Kare...

Sissy Chantel, New Reality Ch. 08

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving on to my life at 'The Agency' Some Interesting New Things. It's 5:00pm sharp, we all must be present and ready to enter the eating area. As we all enter a small but purposeful eating area for us sissy girls, we first get a tray and a plate and mug or glass. The sissy maids who prepared our basic dinner have the food out for us. Today i...

Sissy Life

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I kept staring at the strap-on. I couldn't understand why it was out on the dresser. I tried not to let the concern show. I stood up straight - stood to attention - and thought back to the conversation that had led me here.... I was just finishing the washing up when my Mistress came into the kitchen. This in itself was unusual. Usually if she wanted me, s...

Recruiting of a Sissy Maid Ch. 05

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Five: Chantel Settling in with Her other Sissy Girls "Congratulations Chantel." as Maid Penny tells her today is her 3rd. month anniversary at The Jade Maid Club as they are sitting at the breakfast table with the other girls. Other girls also congratulate Chantel as well. Chantel replies, "Oh thank you all." As the girls eat their breakfast befo...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

Sissy's First Day

by whispy_sub on Sep 13, 2017
Transsexuals & Crossdressers

Sissy let out a disheartened groan as he closed the classroom door. He looked down despondently at the discipline demerit clutched in his gloved hand, "It's my first day and already I screw something up; I can't believe this." It was only his fourth hour here at the Academy, and already he recieved a demerit. He wasn't quite regretting his decision to enrol...

Developing Emma Ch. 02

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

She awoke to the sickly smell of a woman's perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. "Hello again 'Emma'; that's a very pretty name you've chosen for yourself, we shall soon have you worthy of being Emma, and you'll soon know...

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...

Spellbound & Sissified

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

SISSY FOR A SPELL The Omega Psi Phi Fraternity loomed in front of him. The lights were on in almost every room. Frank's hopes, that maybe the brothers of Psi Phi were at the Halloween party across campus being thrown by their sister sorority Sigma Gamma Rho, were dashed. He took a step forward. His hand was shaking and the child's Jack O' Lantern bucket...