First Time Crossdressing Stories

351,059 results
Orientation
Length
Source
Infinite Scroll

When Red is Golden

by techsan on Sep 13, 2017
Romance

Author's note: the following story is purely a work of fiction and any resemblance to real people or events is purely coincidental. The author wishes to express his gratitude to Copperbutterfly for her editing to make this a better story. * Yeah, I have to admit that I grew up being pretty naïve about girls - and women, in general - when it comes to talkin...

Life Isn't All Singing Ch. 02

by Tamed Heart on Sep 1, 2017
Erotic Couplings

(Dedicated to my loving husband who continues to encourage and push me into writing) Jade was visibly upset even though she didn't consider Dannie as a friend. She was even worried that, somehow, Michael might have this her murder charged to him. They just sat in silence holding each other. The thread of fear had woven itself all through their hearts. "Le...

Aria

by GrandToffMarkin on May 16, 2018
First Time

It all started when I had returned from my first deployment to Afghanistan. Nothing bad had happened to me or anyone I knew while I was there, but knowing you could be blown up or shot dead without warning, at any moment had an effect on me, I didn't realize it until I got home. Basically, the little voice in my head that told me I shouldn't do things to al...

A Good Morning

by hafnium10 on Sep 13, 2017
Erotic Couplings

I woke up this morning with you beside me .. something I would never have imagined all of those years ago when you were imagining it for us. As you lay on your side facing away from me, I watch you sleep. Then that feeling from last night starts to awaken in me. I want to reach for you but am hesitant. Yes, last night was amazing as we totally threw ourselv...

The Razor Strop

by magic_tantra on Sep 17, 2017
BDSM

I purchased my first razor strop at a cutlery store at my wife's request. We had read a story in an adult magazine about how effective the razor strop was on bare flesh. I was actually embarrassed going into this cutlery shop not knowing what with the manager was going to say when I purchased the strop. I also decided buy a straight razor thinking that Mistr...

Letter for G. F.

by sobstory on Sep 16, 2017
Letters & Transcripts

Dearest G. F., I miss you, G. F. I miss laughing with you. I miss talking with you. I miss you making me feel so good when I feel like I should feel so bad. You make me feel beautiful when I feel so ugly. I don't have to be anyone but myself when I'm with you. I love you. Isn't that what love really is? Complete and utter acceptance? When I am with you, I c...

Lifting Weights Ch. 02

by sexyness222 on Sep 16, 2017
Transsexuals & Crossdressers

After the first time we had sex at my house, I had not seen Pat for a few days. I was worried that he was going to stop talking to me because it would be awkward, but on the weekend, we went out with a few friends and it did not seem to be too uncomfortable. I noticed that he looked at me a little different, but undoubtedly, that's because he made me his wom...

The Wood Nymph

by capshroud2000 on Sep 16, 2017
Romance

It was a warm fall day, and I took the day off to spend some time communing with nature. I wasn't sure just what was bothering me, but I felt the need to get my head together, and I thought a little time alone in the woods might do the job. I had been hiking along the mountain stream for about an hour and stopped at one of my favorite places. Deep in the woo...

Memoirs of a Dreamer Ch. 02

by DarkDreamerwithHope on Sep 15, 2017
BDSM

Chapter 2 – Lessons and Testing Begin The days passed quickly. She and her Lord would talk most days when He was not gone. Their conversations covered many topics, from family, friends, work, to sex. He always inquired about her day and what she did, how work went, and how things were going with her daughter. No one had ever taken an interest in her like t...

A Case of Self Defense

by Rehnquist on Sep 18, 2017
Loving Wives

I've never submitted a story in the Loving Wives category, and I'm doing so now with great trepidation. Frankly, the commentators in this section are brutal. Many, though, are very insightful and offer genuinely thoughtful comments about writing style, character development, and the like. My only complaint with this category is that much of the basic plot li...