Crossdresser First Time Stories

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Aphora's Mission Ch. 06

by ValoryG on Sep 15, 2017
Transsexuals & Crossdressers

By all accounts, we were saying a final goodbye to Earth. Even though I wasn't close to my parents (my father a doctor and my mother a marketing professional) I figured my mother would miss me. And I would miss them somewhat, especially at Thanksgiving- and Christmas-time. We six didn't see ourselves as the homesick type, and I personally hoped that Aphor...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

Sarah Helps Clean Out a Garage

by SarahCD on Mar 11, 2019
Transgender & Crossdressers

A friend of mine, Sandy, asked me if I would come over next Saturday and help her clean-out her garage. I had known her for several years and her husband had just left her and so, when she asked me for help, I could hardly refuse. In addition, she is cute and I cannot imagine why her husband would leave her. On Saturday, I went to her house. I only ever we...

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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Sex Ed

by britneyfan on Sep 13, 2017
Transsexuals & Crossdressers

My husband and I had quite an open marriage. We were both fairly sexually adventurous and this was reflected in how we both considered it to be ok for us to be going out and sleeping around provided we were completely honest about it and came home and told the other one all about it. In fact, after a while, we found that this recounting of our bedroom exploi...

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...

Gender Bent Society

by turtlerocker on Sep 26, 2017
Fetish

Welcome to GenericVill! A small town in a world that has the opposite gender norms of our society. Some changes from our society is that it is a matriarchy, Girls are considered more athletic, Boys are considered nicer and more emotional, Boys wear what our world's girls would wear, and vice versa, and most importantly, Boys are submissive while Girls are do...

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Sarah Shared the Hot Tub and Sauna

by SarahCD on Feb 26, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more detail and corrected some...

A Dream Come True - The Adult Theatre

by Lovinhose on Apr 14, 2020
Transgender & Crossdressers

The following is a work of fiction and contains crossdresser sex. Hope you enjoy. I welcome comments and feedback, but please note, I'm not a professional writer and I do it for fun and for my readers. My style may differ from others, but it's mine. ********************************************* A Dream Come True-the Adult Theater We have a local adult the...

CD Gets Fucked while House-Sitting

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story that happened recently. I also recently submitted a four-part, runaway-imagination complete fiction story, hope you enjoyed. For anyone not familiar with me or my stories, here's a brief background. I'm middle age, white, a little overweight (hidden well with the right garments), and a married bisexual crossdresser who LOVES getting scr...