Sissy Milking Stories

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Chrissy's Night Out

by Ide32 on Sep 16, 2017
Transsexuals & Crossdressers

Part 1: A Snack Before Dinner Four days have passed since Chrissy's adventure at Futanari Palace. Since that glorious night he only goes by Chrissy, he no longer identifies with the name Chris. He has begun dressing only in women's clothes, with full makeup and a wig. His coworkers weren't all that surprised by his change in behavior, they have suspected hi...

Chrissy's Trip

by Ide32 on Sep 16, 2017
Transsexuals & Crossdressers

Part 1: Trouble in Paradise It has been seven months since Chrissy and Miriam had their memorable first date, and things are going well. Every night Miriam is in town she falls asleep with her giant futahood buried in Chrissy's cum filled ass, and most every night she is away Chrissy heads to Futanari Palace to sate his hunger for cock and hot futa juice....

The Wedding Ch. 05

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Patti Cake part 3) Chapter 5 -- Femdom, Fucking and Femininity... At the end of our time spent with Ms. Walsh, I was left with a lot of questions and I wasn't sure how to deal or cope with any of it... But one thing was for certain, I was starting to see more of the old Patti bubbling back to the surface, being direct and without compromise... The whole d...

Family Chastity Story Ch. 02

by antares34 on Jul 3, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...

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...

Sissy Driving

by MattieG on Sep 17, 2017
Loving Wives

Lindsay had been texting me for days after we met at the restaurant. I'd turned her into a little slut begging for my cock. She wasn't about to give up my dick for her husband's little sissy dick. We had been sexting nonstop since the other night so I knew she was pretty horny by now. I had been very busy with work and our schedules hadn't synced where we co...

The Bimbug

by Testytesterton on Jun 17, 2020
Science Fiction

The world changed overnight with the first cases of the Sexually Infected Subjects Spreading Infections Exponentially Syndrome, or SISSIES, became known. At first it sounded like some urban legend, men turning into hot, horny, hung shemales and spreading the infection to any man that came in them...or any man they came in. It was only after you saw video evi...

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The Femdom Milking Farm

by williewagtail on Sep 14, 2017
BDSM

1. In the yard The male human "cows" were all in the yard waiting to be milked. With the cows corralled together, the girls, Sara, Teri, Jo and Nancy liked top spend some time of a late afternoon inspecting their goods. Leaning on the rails, they ordered all the cows to line up on all fours facing away from them. Legs apart, yelled Teri, let's see what you...

Siss the Bride Ch. 03

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Every marriage has its problems, even mine, which is a huge problem considering I'm a guy who gave up every semblance of a normal life to follow hidden fantasies on a spur of whimsy induced by my hot older brother. My life during my marriage to my brother has been built upon submission, only natural when you are a sissy crossdresser and when he has the perfe...

Mistress Kate Pt. 02

by corduroysissy on Mar 7, 2018
Transsexuals & Crossdressers

When he arrived home from Regan O'Reilly's office Jordan was still in a daze. He needed a drink, no scratch that, he needed a bottle. In a matter of a couple hours he'd gone from having his life threatened, to getting a blowjob from the Leprechaun, to being ordered into sissy sexual servitude by Mistress Kate. She was actually expecting him to be her fucking...