Crossdresser Proper Lady Stories

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I Accidentally Sucked Dick! Pt. 01

by CDJulie on Aug 18, 2017
First Time

I've never given anyone head before although I thought about it for years. I'm a lifelong crossdresser but closeted. I was never brave enough to approach anyone and I shied away from any offers that were made. Mostly, because when I fantasized about sucking dick it was always as crossdresser, more specifically, in the role of a girl. So when I was 33 I vis...

Growing Up Male & Becoming a Girl

by TammyPanty on Mar 26, 2019
Transgender & Crossdressers

My sister is four years older than me, and since our father left the family when I was very young, I have really never known of a household that wasn't dominated by women. Growing up in the late 50's and early 60's, female lingerie was extremely feminine. Most every female wore a bra and full cut panties under a half or full slip every day. Garter belts and...

Was it a Dream

by Classygloves on Sep 16, 2017
Transsexuals & Crossdressers

I had been saving up to buy myself a long pair of black kid leather gloves that I had seen at Saks 5th Avenue on one of my shopping trips. .In order to make an event of it, I had taken the whole day off because I wanted to shopping femme mode this time. One of the pleasures of living the Washington, D.C. Area is that there are so many wonderful upscale stor...

What Just Happened? Ch. 02

by annie_00 on Sep 12, 2017
Transsexuals & Crossdressers

02 – Am I a pervert? When we got home it was late in the afternoon. We had been gone all day, first to the salon, then shopping, lunch, drinks and the crossdresser store. I was tired but felt very sexy under my clothes. I did not want Beth, my step sister, to know that I totally enjoyed the experience today. I thought that she would think I am perverted. A...

How I was Forced Out of the Closet

by gtanya on Apr 4, 2018
Transsexuals & Crossdressers

I was again dreaming of the night I would lose my anal virginity. It had been such a constant since last 3 weeks. I had been talking to a beautiful CD named Rachel since last 6 months and with the thought of meeting her in person, I had planned a vacation to China where she was living. The only problem that I had here was I was going to be on the vacation wi...

Cabin in the Woods

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

Finally, I get to give you another TRUE story after a WAY too long 'dry spell'. This story is completely true (and may be a little boring maybe...would love any feedback). Only the names have been changed to blah blah blah... Anyone who is familiar with my writings knows my stories are true and not made up unless I openly state at the beginning that it's a...

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...

Rest Stop Romance Ch. 01: Pilot

by Dark_Rose90 on Sep 15, 2017
Transsexuals & Crossdressers

~The following is entirely fictional and just a fantasy of mine. Any likeness to actual persons or events is unintentional and coincidental. Also, this is just a Pilot. If the story gets enough positive feedback, I'll continue it on a regular basis.~ My name is Rosalie or just Rose for short. At least it is when I'm dressed up like a 20 year old college gi...

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...

My Secret Revealed Ch. 06

by jealouscuck on Jun 19, 2018
Transsexuals & Crossdressers

I had crossed a line by myself. Here I was at Sally's apartment, not knowing who was there for sure and transformed completely into a passable woman. I had ventured out and found a crossdresser shop on my own. The sales "person", Tammy had not only helped me with shoes and clothing, she had me come back in for a complete makeover before I was to go to Sally'...