Caught Crossdressing Stories

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Orientation
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Infinite Scroll

Shemale Trouble

by Braids on Mar 11, 2007
Fetish

You were at a bar when it happened. You were just having a drink when a hot girl started hitting on you. You had nothing else better to do and you didn’t want to pass up an easy lay so you offered to take her back to your place for a little fun. She agreed without a question, but as you were walking out of the bar, you felt something hit the back of your hea...

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Life and Time of Lady Vargos Ch. 01

by rik581 on Oct 3, 2018
Transsexuals & Crossdressers

I am in the process of reposting my stories. *** "The Life and Times of Lady Vargos" is the second book of the Martin Hastings adventures into a life of forced feminization. This story follows the feminization and marriage of a reluctant young man as he is forced to accept his fate as a male/bride, in a same sex marriage, arranged by his family. This stor...

Taken by My Wife

by BlondeKaryn on Sep 12, 2017
Transsexuals & Crossdressers

My wife had recently found out about my crossdressing. She was a little upset at first, but then seemed to be more accepting of it as time went by. I came home from a business trip a couple of weeks ago to a welcome that I could never have imagined in my wildest dreams. I had taken quite a few of my clothes with me, and spent every minute possible on my tri...

Bullied

by Testytesterton on Sep 12, 2020
BDSM

You are an 18 year old boy surrounded by bullies everywhere you turn. Your high school has apparently elected you the mascot of the losers and wimps and selected you to receive the lion's share of attention from the bully boys while simultaneously being ignored at best by the girls you lust after. At home, your family is cruel and controlling or coddling and...

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Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

Boy to Bride Pt. 01 Ch. 01

by sissyscarlet on Jun 19, 2018
Transsexuals & Crossdressers

Part 1: Adam MacDonald Chapter 1: Ms. Alice the Widow Adam carefully shifted the wooden board back in to its place. If only people knew what I kept up there, Adam thought, and smirked to himself. Before he was down from the stepping stool, he looked up at the ceiling 2'x2' entry leading to the attic—an artifact left for insulation and electrical, but Adam...

Fetish Life

by Kinkyguyohmy on Apr 20, 2020
Fetish

You wake up just as the alarm on your phone blasts a corny jingle right into your ear. You lazily stretch, pull your covers off your body and slowly rise from your bed. You meander over to the mirror that hangs on your door and look at your reflection. A teenage boy with light brown hair, glowing grey eyes and an average build stares back at you. You smile....

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A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

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Undercover Angel Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

When Mike Harris stole two point seven million dollars in cash from his employer, he knew that his life had changed forever. It's one thing to steal that amount of money from your bosses' safe; it's quiet another to steal it from a ruthless gangster who is heavily involved in narcotics, prostitution, gambling and murder. Mike was Tony Leonardo's bookkeeper,...

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...