Crossdresser Caught Stories Stories

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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...

Dad My First Lover Pt. 01

by sarahchica96 on Sep 16, 2017
Transsexuals & Crossdressers

Introduction I'm Sarah a 20 y/o closet Bisexual crossdresser, 5ft 6 , slender body I achieved by working out a bit. I love dressing up in short skirts, dresses, heels, typical lingerie and I have a fetish for the Naughty Secretary look. Main story starts here I had come back home from college for the winter holidays. It was just dad and me at home since...

Mistress Chantel, Tranny Dominatrix Ch. 12-13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twelve: Another Play Day Work Day at Our Studio. I arrive at my studio dressed for another day of fun and exciting dominatrix work. I park my "Plum Crazy Girl." step out in my red leather thigh high boots over my black sheer pantyhose. On my feminine looking body is a red leather form fitted mini dress with loose pleated, A-line skirt barely coverin...

Forced to Dress

by married40scouple on May 11, 2020
Transgender & Crossdressers

"Can I have two rum and cokes, please?" The sexily dressed, long-legged, thin brunette asked the bartender, speaking in a deep tone. "Lose a bet?" I asked the crossdresser who sidled up to the bar and order the drinks. "I don't want to talk about it." He replied in a husky voice. "At least you look real good." I smiled at him. "She dressed me up. I have...

Crossdresser Crosses Over for Good

by TVTrishCD on Jun 8, 2020
Transgender & Crossdressers

I certainly allowed myself be conned! So, I had a problem with my turn signals on my car back in early January. I was pretty sure it was the turn signal switch, but not sure. There is a site where sex ads are very prevalent. In the CD section it's mostly hispanic, and oh do the latino boys just LOVE us white cd's!! They are very relentless in their pursuit o...

Things That Turn Me On

by Raquels_Panties on Apr 22, 2020
Fetish

I'm a 28-year old male. I live a normal life in public. I like women and men. I'm 5'8" tall and weigh 135 pounds. One might consider my features, my face, my body shape, more on the feminine side of the spectrum, than on the masculine. I'm okay with with that. I use this to my advantage and have allowed my hair to grow out. It falls just below my shoulders....

A Wife Comes Around Ch. 02

by pinkpanteez247 on Sep 11, 2017
Transsexuals & Crossdressers

Reading Part 1 will help explain some instances in Part 2 but it's not necessary. Hope you enjoy reading it as much as I enjoy writing it. * I caught my breath after my wonderful experience, as we were all around the table now commenting on my orgasm. I sipped my drink and exclaimed that was the best orgasm I've ever had. It was getting late now and I had...

Kyle - Martini Date

by Leigh_216 on Mar 2, 2020
Transgender & Crossdressers

Hi, I am Leigh, a Crossdresser (CD), Caucasian, 68" tall, women's size 8 or 10 depending on the brand, green eyes, and shoulder length hair. I have always had soft facial features. My stories are more of a diary entry than a novel. They actually happened but I changed the places and names. Kyle, my unofficial boyfriend has invited me out to have dinner and...

Sarah had Sex in an ABS

by SarahCD on Feb 12, 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 Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...