Sissy Milking Stories

28,345 results
Orientation
Length
Source
Infinite Scroll

Tommy Joe and His Pa Ch. 02

by Ed0613 on Sep 1, 2017
Humor & Satire

-----0----- Note: It order to get the full impact of this story, one must first read Chapter 1 -----0----- The scene is a few days later at a decrepit old farmhouse, the home of Tommy Joe and his Pa. In the front yard is Lester's dilapidated old pick up truck and a shiny new, operating oil well with a huge storage tank. A very attractive young woman, perh...

Stan to Stella Pt. 01

by Maximus_eros on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: All persons depicted are 18 or over. The names have been changed to protect identities as this did occur in reality to some degree. ***** Like any story, everything has a beginning and thus we have the day that Stan began his journey of self-discovery at the manly hands of Jason. He like so many was subjected to years of ridicule and shame. Th...

The Making of a White Sissy Slut

by AfroerotiK on Sep 18, 2017
Transsexuals & Crossdressers

When he replied to my ad online, Steven said he was an attractive, 30-something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I'd said something to offend him and responded by sayi...

Discovering Mistress Sarah's World Pt. 08

by oneguy4fun on Sep 14, 2017
Transsexuals & Crossdressers

Part 8 -- Complete Surrender Chapter 21 Leaving Behind Joe's Life Mistress Sarah was very pleased with Josie's training and feminization. She was anxious to have complete reign over him so she sent him home a day early to pack up his things and prepare to leave behind his life in the Philadelphia suburbs. "I'm sending May with you Josie," announced Mistr...

A Shell of A Man

by uppishcarrot on Sep 13, 2017
Transsexuals & Crossdressers

Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty women at work, but there were also plenty of hot women who li...

High School Fuck Slut

by TonyaTV69 on Sep 25, 2017
Transsexuals & Crossdressers

I grew up out in the country as a boy with my mother and 2 sisters. My dad was never around since he was always off working or as we found out some years later running around cheating. If we saw him at all it was on the weekends for a quick family outing to the mountains or park. Once in a while mom and dad would get all dressed up and go out to dinner. This...

Helen Ch. 06-07

by Philippasubmaid on Jan 2, 2018
Transsexuals & Crossdressers

This story is a graphic tale of a Dom and his very submissive transgendered male and a n other. If you are offended by tales of BDSM and sex between consenting adults then read no further ......... other wise enjoy It is best if read with previous chapters. Feel free to leave honest comments or suggestions, it really does encourage those of us who write t...

Cuckold's Descent

by syncbush on Mar 27, 2020
Cheating Spouses

Thank you to those of you who have liked or taken the time to comment/message me. I really appreciate the feedback. Feel free to add additional chapters, suggest ideas or leave comments. It is great to get ffedback and encourages writers to continue developing the stories. And special thanks to the Admins for making this story of the week! Really appreciated...

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Tales of Kirkjufell

by Alvae on Feb 23, 2019
Miscellaneous

"Hey, you are finally awake..." A strange creature speaks to you, sitting atop of pile of bones, and skulls, tapping on unbeknownst skull of what appeared to be a grey ogre, as there is only one eye "Let me bend your ear for a moment, and tell you stories about an Orcess who dared to defy the Gods, and has been exiled from their place, unright...

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A Sissy's Reward

by keptsissy on Sep 19, 2017
Transsexuals & Crossdressers

Every time he does this to me he drives me crazy, keeps me addicted to his hand. I feel my sissy-like penis strain to escape from between my legs. I'm very small, only about 3" when hard. I keep it tucked for him, hold it tight between my legs at all times...except for when he does what he's about to do to me now. He's not interested in my tiny thing. Only...