Sissy Crossdresser Stories

7,061 results
Orientation
Length
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Infinite Scroll

Asian Bimbo Sissy Slut Ch. 01

by melltsslut on Sep 14, 2017
Transsexuals & Crossdressers

Soo...where should I start? I'm sitting here now in liquid black leggings, a hot pink crop top, and a carefully teased wig, with D-cup breast forms glued onto my chest. Oh, as well as the special panties my girlfriend designed - for both of us! From the outside, they look like French briefs. On the inside, they're a little more special, if you get my drift....

Vacation with Aunt

by Alice Dragonslayer on Mar 19, 2018
Transsexual

Hello, you are 18, semi long black hair, feminine build, shy and submissive. You visit your Aunt Katy (looks like Katy Perry) for the summer. She may or may not have a daughter. She has a very feminine house and has a pink car. She dresses pretty hot. Her breasts are perfect and she's in her 30's. She doesn't have a husband and stays in an apartment with one...

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Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Recruiting of a Sissy Maid Ch. 11

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Eleven: People Moving into New Roles and More. Chantel has made her way back to her club dorm room, enjoying the corrective measures of being a Domme over Biff and Marty. She is certain they will be much more mature and even though they still hold powers over the sissy girls like all other male minder/staff, they will better respect what these sissy...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

What Just Happened? Ch. 04

by annie_00 on Sep 12, 2017
Transsexuals & Crossdressers

Chapter 04 -- I am no longer in control I looked at Beth and so did the pizza guy. The delivery guy started a discussion by saying, I do not want to offend you girls, but you are both very attractive and I see one of you has panties on because I can see them. So the other panties on the floor must be yours he said as he looked at me. What is Beth doing st...

Sissy Manners Classes Ch. 01

by fridaysissy on Sep 12, 2018
Transsexuals & Crossdressers

It was late night, I am 10 km away from my room waiting for sharing cab or auto service to reach my room at last I joined a sharing auto service with two members including me. The other passengers stop came early, and I remain alone in auto waiting for my stop to come. Driver said he is stopping the service and returning to his home and asked me to get down....

Trapslut

by Alexia Wright on Aug 20, 2015
Fetish

Today is the day. Your erotic crossdressing blog videos have earned you your first practical job as an escort. Being the famous online sissy slut Annie, you used to pay the bills selling your horny pictures and masturbation videos to guys on the Internet. You got out of bed, still in your pink babydoll nightie complete with a baby blue thong and head for the...

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Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...