Crossdresser First Time Stories

351,031 results
Orientation
Length
Source
Infinite Scroll

My Short Daydream

by sexnkitten69 on Sep 14, 2017
Erotic Couplings

I started dreaming of seeing you, and wondering how sex would be the first time we have it again. I imagined us alone inside the door of a room, kissing gently, and then leading you to the bed, and having you sit near the head board, and climbing on to your lap with my legs kneeling on either side. We both pressed our foreheads together and gazed at each oth...

Dancing With Desire Pt. 01

by kiwikat on Sep 14, 2017
Erotic Couplings

I will never be sure exactly how he caught my eye, but somehow he did. Tall and cute with a dark colored shirt on; that could be what did it. That's kind of like tall, dark and handsome right? In either case, it was enough for me. I watched him from out of the corner of my eye and immediately determined that he was going to be my new dance partner if only...

Winter Dreams

by browndream72 on Sep 16, 2017
Sci-Fi & Fantasy

The moon gleamed upon the snow ladened trees and glacier white ground. All around, one could hear the soft sighs and murmurs of lovers embracing, caressing, caring for one another. A perfect winter evening for love, or so one lone soul thought as he sat staring out into the night sky. "Mayhap, I should send my little love a sweet dream of me." The man thoug...

Summer Camp Letters #02

by PrincessErin on Sep 16, 2017
Letters & Transcripts

Taylor, Dear fucking god your letter made me so horny! I'm sorry I didn't write before now. The boy's camp has been so busy, it's crazy. First off, I got a different job. On the very first day, I was asked to work in the office and I stupidly said yes. This means instead of being outside sun tanning and fixing things, I'm inside doing computer work. There i...

Jungle Justice

by rufriter on Sep 14, 2017
Erotic Couplings

This is something new for me. The expressions are as authentic as I could find, and the names were "borrowed" from the members of certain African men's and women's national soccer teams. If there are any inaccuracies, put them down to lack of first hand knowledge. * Ekene had become separated from the main hunting party when he stopped to remove a thorn...

I Am Jack's Life Ch. 09

by Finis on Sep 13, 2017
Novels and Novellas

Author's note and acknowledgements This story has sat on my hard drive for four years now. I wrote it, all twenty chapters and 95,000 words of it in eight days of a frenzied, near trance-like state, sitting on my couch with my wife's laptop. She would occasionally have to remind me to eat. When the dust settled, and I looked up, I realized a couple of...

Seconds

by Quikpeek on Sep 12, 2017
Loving Wives

This is a follow-up to my first story "First Creampie." It is about the exchanging of bodily fluids. If you are opposed to this sort of thing then please do us both a favor and skip to another story. Thanks to Kumani for editing help. * Since the first time my wife had brought home my first creampie our sex life had dramatically improved. It was like we w...

My Former Lovely Wife

by vietnamvet on Sep 5, 2018
First Time

This story is purely fictional and any names or places that might be familiar to anyone is only coincidental. *** My name is Dave and I once was married to the most wonderful woman I had ever known. Her name is Anna and we were a very happy couple fifteen years ago but over the years our relationship changed drastically and we are no longer together. I wil...

The Club

by onemoretime9876 on Sep 15, 2017
BDSM

Lisa went to the club as usual on Friday morning. She enjoyed her time on the elliptical trainer, chatting with her friends to make it seem shorter. Then she did the upper body circuit ending with some intense ab work before heading into the showers. The only difference this morning, was the scheduled massage. She was really looking forward to it. Her muscle...

Kathy's Pool Party Ch. 04

by MemberX on May 21, 2019
First Time

Please note that this story, while obviously part of the Kathy's Pool Party series, is also a continuation of A Week With Cathy (I strongly suggest you read that first). BERNI I was massaging my boyfriend's cum into Kelly's breasts when, of course, Kelly's girlfriend Hanna walked into the room. She took in the scene -- me making Kelly sigh, Paul lying next...