Sissy Shemale Stories

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Orientation
Length
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Infinite Scroll

Life With Miss Ida Ch. 04

by Sheermistress on Dec 2, 2017
Transsexuals & Crossdressers

As mentioned in Part 1, all Mistress and I had been waiting on was for the lease to run out on my place, so I could sort everything out and finally move into her place for good -- I had practically been living over the past few months anyway, so it really wasn't as big a move when it all came down to it. The entry way to our home, which was on the ground f...

The Pantysissy Diaries Ch. 01

by JPantyboyVSL on Sep 2, 2017
Fetish

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. ***** Jay was on his way back to New York from a weeklong work conference in Chicago. He decided to take Amtrak back to NYC. He got on the train in Chicago and noticed a hot young blonde woman in her 20s s...

You Got the Part! Ch. 03

by Checkmate215 on Sep 26, 2017
Transsexuals & Crossdressers

I would like to thank Mr_Owlow for all his assistance with editing this story. In typical Riley fashion I was in a bit of a situation. GiGi's T.V. show was a complete success and we were picked up for a second season. America was in love with the cast especially GiGi and myself. We were making the rounds on talk shows and late night. We were doing endorse...

The Job Interview

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

I had been searching for an executive assistant for some time now and had interviewed a few really potential ladies and 'ladies' -- all very skilled and would be worthy of the position, but something was missing from them all until I interviewed Jessica. The first time I interviewed her was a general 'meet & greet' interview with about 15 other girls --...

The Double D Ranch Ch. 02

by JDBones on Sep 15, 2017
Transsexuals & Crossdressers

Jeff Malville awoke slowly, moaning softly. He almost forgot where he was in that moment where sleep and being awake clashed. However, after that split second, it all came rushing back and he moaned in delight. He was a captive on the Double D Ranch, and even though he was considered an employee, the only thing that he'd come to be good for was a sex slave...

Afro Stress Relief Ch. 10

by llts1970 on Mar 30, 2020
Transgender & Crossdressers

I woke up on the Saturday, not believing what I'd got up to in the Beer Bust and not sure what to do, now everybody knew what I was, a little white sissy bitch that worshipped black dick! How would everyone treat me on Monday at work, Elizabeth had said not to worry as 'what happens at the Beer Bust stays at the Beer Bust', however how could I tell my black...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

She has a dick!

by AdamAK on Apr 3, 2018
Transsexual

I'm John. just an 18 years old typical guy. I go work out from time to time, which keeps me fit, but I'm still no where near bulky. You can actually say that I'm skinny. I never thought about dicks. Thinking about it now is simply weird. I don't know. I just love women. Although I'm a virgin. It's kinda shameful when I think about it. Although I had a couple...

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Lesser of Two Evils

by Andi_Lembke on Sep 25, 2017
Transsexuals & Crossdressers

[So to update you all. I'm sorry I haven't completed any more chapters of NWTBYG or Porn Princess. They're in the works, but creation, and good storytelling takes time, something I have less of now. I left my receptionist job to take a writing gig, and all my writing energy is going into that, but my passion for hot stories smolders intensely under the surfa...

Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...