Crossdresser First Time Stories

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Orientation
Length
Source
Infinite Scroll

The Only Constant is Change Ch. 09

by Minstrel_Blue on Oct 10, 2018
Novels and Novellas

Author's Note: Thank you to those who have faithfully followed the story of Jeremy's life to this point. If you are new to the series, I think you can begin from here and enjoy it just as much. But overall, I think you're better served if you go back and read the earlier chapters because the point of the series is to see how a young man changes over time b...

Fiction

by avrgblkgrl on Sep 13, 2017
BDSM

Jessica's perfect form hung just inches from the floor at the slightest of angles, facing the skylight of his loft. Her back was gracefully arched, arms drawn back and down. Her inner wrists were joined behind her, two fists kissing each other, thumb lying beside thumb, and a series of well-spaced, ornate knots linked them to her secured ankles. One set of r...

A Woman on the Weekend

by TiffyKitty93 on Nov 26, 2017
Transsexuals & Crossdressers

~So what started as a one-shot, primer story has become a trilogy! Unless I think of more to do with the story without it getting too stale, this will probably be the last part. Plus, I want to write something with a happy ending. I recommend reading "A Weekend of Firsts" and "A Halloween Weekend" if you haven't already before reading this one!~ ***** Send...

The Adventures of Andrew Ch. 01

by jklazarus on Sep 19, 2017
First Time

On his 18th birthday, Andrew has his first sexual experience My name is Andrew. In high school, I wasn't cool enough to hang out with the cool kids and I wasn't nerdy enough to hang out with the nerds. I fell right in the middle of the social hierarchy. The average guy. The ignored. It didn't help that I was painfully shy either. I found it difficult to mak...

A First Time for Everything Ch. 04

by curious_cait on Sep 13, 2017
First Time

Hi there! I'm sorry I've taken so long to get this out, but I've had a busy few months. If you're new to this story, I recommend you read the preceding chapters first, as this is the 4th installment in a series. All characters are over 18. Happy reading! * * * * * All throughout the next day, his promise ran on repeat through my thoughts: "You're going...

Penny and Beth Share It All

by Archer2050 on Sep 16, 2017
Group Sex

"Hurry up!" Beth exclaimed, peeking out her bedroom door. "They just opened the front door!" Behind her, Beth's boyfriend, Kevin, was hurriedly jerking himself as Penny sucked and licked his cock head. Penny teased his swinging balls with her fingertips and Kevin suddenly exploded. A fountain of cum splashed across Penny's face, dripping down over her expos...

Reset Ch. 03

by nushu2 on Sep 16, 2017
Sci-Fi & Fantasy

I woke up alone. Brenda was probably at college and Sarah was doing whatever she does. I took a deep breath and stretched, feeling very good about the night before. The more I thought about it, I felt very good about the past six months. I remembered when I was thawed out and my first week here. I had a lot to learn. Now, it's just common sense. One of the...

Quick Lube

by agent5150 on Aug 31, 2017
Erotic Couplings

Working at the Quick-E-Lube was miserable, tedious work, especially in my position as "lower bay technician." Basically, my part in the process of changing a car's oil was to remove the drain plug, remove the filter, replace drain plug, install filter. Not exactly an intellectually challenging job, not to mention the fact that it was dirty and, at times, dan...

New Year's Eve 2014

by kristendixon79 on Sep 26, 2017
Group Sex

Some of you knew, some of you may have suspected, but for those of you who had no inkling, I have been fighting a serious illness for the last six months. The photos that have been posted on my blog recently were taken New Year's Eve, when I dipped a toe back into my sexuality for the first time since the surgery last July. My sexuality had been dormant for...

Cum Addict Pt. 02 Ch. 02

by novella_champ on Dec 3, 2018
Novels and Novellas

Chapter two: Kat Kicks Off Her Internship This is module two, chapter two. This is a novella of sorts. The intent is to have 4 modules total covering different times in our main characters life. While it is feasible to read any of these independently, this is a carryover story, so reading them in order is beneficial. In module one, our main character, Kat...