Crossdresser Lover Stories

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Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

Sarah Meets a Friend

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I posted a listing on Craig's List for a "cum buddy". I explained that I am a crossdresser and that I wanted to find a regular sex buddy. No commitment, just sex. I love to get on my knees to give a blow job. I had several replies. One was local and sounded promising. I don't rush into meeting with a total stranger. First I always exchange a few emails and m...

My Journey to Heaven

by Corina84 on Sep 14, 2017
Transsexuals & Crossdressers

How did I end up here? I couldn't believe what just happened! I was in a daze from what I just did. I was neither sickened or disgusted by it, I was just surprised that I had come so far. Here I was, on my knees with cum drizzling down my face. Something that I have fantasized about for years, but was never able to gather enough bravery to step out and try...

Crossdresser Evolution Ch. 06

by pantyhigh on Aug 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's panties. Recap - Crossdresser Evolution - Ch 02 - Getting my wi...

A Day at the Beach

by Danielle987 on Sep 16, 2017
Transsexuals & Crossdressers

Bit of background to understand the context. I am Danielle, I am 18, very petite 5" 8 65kg and have long blonde hair. I have been a crossdresser since I was 12. Australia, it was the middle of summer as I was driving to my friend Kate's house. We had planned to go to the beach as I became more brave in my crossdressing adventures. Kate was the same age as...

Sarah Meets a Buddy

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I posted a listing on Craig's List for a "cum buddy". I explained that I am a crossdresser and that I wanted to find a regular sex buddy. No commitment, just sex. I love to get on my knees to give a blow job. I had several replies. One was local and sounded promising. I don't rush into meeting with a total stranger. First I always exchange a few emails and m...

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...

The Ride of a Lifetime

by CuriousJ95 on Nov 6, 2018
Transgender & Crossdressers

Hi everyone, this is my first attempt at writing. I hope you enjoy and I can't wait to get some feedback from everyone. Please be honest in what you think...I can take it. This is a true fantasy of mine. *** I'm a curious man that is married to a wonderful woman but as time has passed our sex life has diminished quite a bit. We still occasionally enjoy...

My Heels

by shoeslayer on Sep 16, 2017
Fetish

Another day, my lover is already on his way to work as a locomotive electrician for the railroad. The sun shines through the curtains of my bedroom and the birds are chirping. I am in a great frame of mind today, last night my lover told me what my heels do for him. The way he told me he, was getting me turned on! and his husky voice had a lot of feeling w...

Jack's First Time

by bi_cpl_with_crossdresser on Jul 13, 2020
Transgender & Crossdressers

There were no secrets between Jack and Marcy, hell when you have been married to the same person for almost 24 years and together for even longer there was no need. Marcy had professed to Jack well before they were even a couple that she was bi and soon after they were dating Jack confessed he was a Crossdresser, a few years later he also said he thought h...