Sissy Milking Stories

28,345 results
Orientation
Length
Source
Infinite Scroll

The Wedding Ch. 01

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Intro) This is the continuation in the life of Dale Horn and the never ending saga of both his pleasure-- and his plight while living in this new world of sexuality and discovery brought about through the hands of his caring, supportive Mother and as well, his long lost love Patti... Where we left off -and with every ones encouragement our Dale saw himself...

Mother Dear Pt. 12

by keptsissy on Sep 14, 2017
Fetish

My white frilly lace panties delicately pulled down passed my stocking tops, so as to not crimp the lace, dangle from my ankles. The twelve inch small chain that holds my ankles and the thin steel cuffs locked to it rests on the carpeted floor, the panties rest on top of it and cover the tops of my 3" spike heel pumps. My small but erect penis exposed in fro...

The Rendezvous Ch. 03

by CassidyCaine on Sep 26, 2017
Transsexuals & Crossdressers

(Author's note: I have tried to get an editor for this story but failing that after over a week of looking I'm publishing it. Please be aware this work has some fictional coercion and other sissification elements.) The car drove through the city as the night pressed around Nick, watching the buildings flicker by as he wondered what was in store for him....

Playing the Part

by Sissysdream on Jan 20, 2020
Transgender & Crossdressers

All people in this story are above 18 or older. This is just a fast story I wrote and don't know if I will do any more on this story. *** My name is Tommy, but these days I go by Tammy. A few weeks ago, I was turned out by my high school bully during summer break and now I am a happy cum drinking sissy. I know I'm getting a bit ahead of myself here so let...

College Days – Domination 101 Ch. 03

by oneguy4fun on Sep 25, 2017
BDSM

Linda and Lori turned their attention to Pam when she walked in with Joe. They complimented her on how sexy she looked. Pam enjoyed the attention. "Joey did a nice job preparing me for my date," she said as she presented herself. Next the girls attention went to Joe and they laughed at the sight of him covered in black marker and dressed as a slut in red pan...

Panty Posers Ch. 06

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

We entered our building and bumped into our downstairs neighbor Jerry. He was taking his trashcan back to his apartment. He set it down at the landing and gave us each a good look. He wasn't at all phased by our appearances. "Little early for Halloween, isn't it...boys?" he asked. We both were fully aware Jerry knew we were sissies. It was fairly obvious...

The Dominatrix Order Pt. 04 Ch. 04

by Jwwsmith on Apr 23, 2019
Fetish

Slave boy departed the docks and stumbled back to Femininus, dazed and in despair. He had no idea what to do. He had made the arduous journey, both physical and emotional, to becoming a slave of Femininus, suffered so much heartbreak and rejection to finally find his perfect Mistress, only to get to spend such a brief time with her before she was taken so ve...

A Photo Session, My First

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

When he called and said "We're going to something special today, sissy boy." I got instantly wet in my panties. He arrived at my house and stripped out of his clothing almost before I had a chance to close the door. I feel his large hand cup my penis and balls. He covers them completely and easily. I'm small, less than 3" erect, baby-like. I feel my little...

From Her Ex-Boss to her Bitch Pt. 06

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read this story if fantasy is not your thing. This has scenes of outrageous levels of forced sissification, forced bi and gay scenes, watersports and general humiliation and degradation. It's just pure fantasy and includes some hypnosis. Some readers find these stories too full of fantasy, in which case please just don't read it. ***** It had...

Retired to a Whole New Life Ch. 02

by sissymissyct on Feb 11, 2019
BDSM

As my fate was now sealed by the lock, Mistress Michelle handed me the key and instructed me to put it on Cara's ankle bracelet. I gently undid the clasp and attached the key as instructed. I re-fit the bracelet and lovingly kissed her foot, and then Mistress Michelle's. They helped me too my feet and we went back out to the living room, Michelle locking th...