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Transgender Sex Stories – Real Encounters & Passionate Experiences

Welcome to DoubleList’s collection for trans sex stories, where our users share their real, salacious experiences. Your secret encounters are always safe with us because your identity will be 100% anonymous. So, come on in and add your steamy trans erotic stories; we can’t wait to hear them.

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Category: TS / CD

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A Night of Unexpected Connections at a Party
I am a full time crossdresser. 24/7/365 I can be found wearing fem clothes. Dresses, mini skirts, blouses, heels, stockings, make up, wigs, the entire ensemble. I am ALL fem, a sissy, a total bottom.

Posted by a TS / CD

By sissyjamie4u

A Unique Encounter at the Coffee Shop
This was back in the days of CL and at the time I was 20 or so and I had answered an ad looking for young twink who wanted to do some sissy play with a husband and wife. I would first be meeting with

Posted by a TS / CD

By sissysamantha1

An Unexpected Encounter at the Park
The text read: meet me at ____ Park, and wear something sexy. It wasn't someone I know, as it wasn't in my contacts. He sent me a picture of his cock. Mmmmm looked delish. I texted him back

Posted by a TS / CD

By Deleted User

A Surprise Getaway to Florida with Daddy
I am a sissy bottom beotch who loves and enjoys the cumpany of older daddys. There are several criteria I look for in a daddy: handsome, financially secure, hi sex drive, financially secure, able to

Posted by a TS / CD

By Deleted User

A Mysterious Encounter at the Theater
I decided I needed to get some strange daddy dick, do I put on my cock hunting outfit-- black blouse, pink mini skirt, sheer stockings, 5 inch cfm heels, black wig, my falsies, and makeup--and drove

Posted by a TS / CD

By Deleted User

An Unexpected Triad Meeting Next Door
I am a full time crossdresser, who lives my life as a female 247. I have been hooking up with top, alpha mens for the last 7 years. I have been with my current lover for the last 4 months. But I

Posted by a TS / CD

By Deleted User

An Unexpected Family Reunion and Secrets Revealed
So there I was, on my knees, with daddys thick cock down my throat, when we heard the front door open then close. WTF, daddy. You told me you had the house to yourself the entire weekend. You told me

Posted by a TS / CD

By Deleted User

A Journey of Self-Discovery and Connection
Ok my name is Sheila, I am a crossdresser well I am a sexy adventures woman in a males body. Ok I started looking at websites that was for girls like me and I tell you it was so fun I got

Posted by a TS / CD

By sexyslitsheila

A Journey of Self-Discovery and Connection
Ok my name is Sheila, I am a crossdresser well I am a sexy adventures woman in a males body. Ok I started looking at websites that was for girls like me and I tell you it was so fun I got

Posted by a TS / CD

By sexyslitsheila

An Unexpected Encounter in a Parking Garage
So the other day I received a text from a number I didn't recognize, but the person who sent it knew my name. He said a friend of his told him about me. The text read to meet him at a parking

Posted by a TS / CD

By Deleted User

A Couple's Journey into Bisexual Exploration
So I’m bmwm have my sexy wife that loves me too much and knowing what I can do lol and enjoy we both love sucking big white cut Cox and I’ve been wearing silky panties since I was 12 and

Posted by a TS / CD

By Deleted User

A Unique Encounter Between Two Lonely Hearts
The ad read: 73 year old lonely widower seeks 1st time with a crossdresser. Me, being a bottom crossdresser who loves older men, responded to his post. After a few emails, and texts, he invited me

Posted by a TS / CD

By sissyjamie4u

A Crossdresser's Journey to Find Pleasure
What is it that men don't understand? I'm very specific in my posts. I am a crossdresser, who bottoms ONLY! I do not top. I don't want my lil pp clit licked, kissed, touched or in your

Posted by a TS / CD

By sissyjamie4u

Exploring Life with an Older Partner
I used to date a much older daddy that loved sharing me with his friends. Daddy turned me into a cock crazy cock loving sissy. Daddy was the 1st man I had ever been with. I lived with daddy for a lil

Posted by a TS / CD

By sissyjamie4u

A First-Time Encounter with a Crossdresser
Last week I was sitting around the house and looking on dl for some cock to hop on. Saw a post by a much younger man that was looking for a 1st time experience with a crossdresser. We exchanged pics,

Posted by a TS / CD

By Deleted User

An Unexpected Reunion Leads to Surprises
I love daddys, especially men that are at least 20+ years older than me. Married, straight, bi, gay, it don't matter, as long as I get their cock n cum, I'm 1 very happy bitch. I have a

Posted by a TS / CD

By Deleted User

A Journey of Self-Discovery Through Crossdressing
I was a married heterosexual male for all my life. At the age of 45 after being married for 17 years my wife left me for another man. This left me feeling inadequate and depressed. One day I was in

Posted by a TS / CD

By juliannajake

A Night Out at the Local Store
Well I'm married and like to wear my wife's clothes. It just makes me feel so feminine wearing tight leggings. I also like wearing thongs and heels. One night I went out to the local adult

Posted by a TS / CD

By bmodirty

A Night Out at the Local Store
Well I'm married and like to wear my wife's clothes. It just makes me feel so feminine wearing tight leggings. I also like wearing thongs and heels. One night I went out to the local adult

Posted by a TS / CD

By bmodirty

A Surprising Reunion with My New Boss
PART 2: We ended up in my bed, where I got between his legs and sucked his cock again. After he was hard, I rode him again. OMG, the feeling of his cock buried deep in my asspussy was incredible.

Posted by a TS / CD

By Deleted User

Top Authors

Discover the most engaging creators on Doublelist — ranked by views, listens, and upvotes, with fresh voices breaking in every week.

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derake14
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Ads on DoubleList 46.9k 523 2.9k
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Sucking appendage in the club 44.4k 456 1.9k
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Gym kiss pt.2 48.8k 605 1.7k
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First really big appendage 10.0k 357 1.2k
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An absolutely amazing 3 friends 32.5k 318 1.1k
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