Crossdresser First Time Stories

351,031 results
Orientation
Length
Source
Infinite Scroll

Backsliding Ch. 07

by bzzzman on Sep 26, 2017
Loving Wives

Time flies when you're having fun. Time must have been zipping by at breakneck speed for Sarah because she seemed to be having the time of her life. For me, time was beginning to slow to a crawl. I wondered if maybe my fun had run its course. Don't get me wrong, I enjoyed Sarah's latest escapade at Charades and the wild night of sex that followed. I think I...

Dear Mother - Finding Penny

by coaster2 on Sep 12, 2017
Novels and Novellas

Author's Note: Now before all you flyboys and veterans get on my case about the technical errors, just remember, this is a work of fiction. I've never served in any American military unit and I've never flown an aircraft. The idea is to tell a story without letting the technical stuff get in the way of the plot. I hope that doesn't put you off too much. Thi...

Hinn Ch. 60-62

by UsuallyPresent on Sep 21, 2020
Sci-Fi & Fantasy

Author's Note - Please read from Chapter 1 to make sense of this. This is not a quick stroke story. There will be sexy-times, but they will only happen as the story's pace dictates. All characters participating in sexual activities are 18 or older. Chapter 60 As the last of her Jann arrived, Emma told Ray, "By defending and not attacking Jann, even when J...

High Heels and Stockings Tryout Ch. 02

by neon_noodle on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 2: Bi-sexual Sluts in Stilettos Author's Note: Thanks to all who read and enjoyed my first story. I hope you like this one too, and get so excited by it you have to jerk off and blow a big, wet load. Enjoy! * After my first semen-splattering cross-dressing experience, I was hooked on dressing up like a slut, and masturbating in stockings and high...

Allure of Dreams Ch. 01

by Monmusu_Writer on Jul 17, 2018
Sci-Fi & Fantasy

AN: Sorry for the wait. I was initially planning on continuing Drawn into Passion, but I found it difficult to write due to the game setting. I therefore decided to start a new series in a more traditional setting, which is easier for me to write and therefore quicker to update. I'll still continue Drawn into Passion at some point. This series is set in the...

Performing Nude on Campus

by boknude on Sep 12, 2017
Exhibitionist & Voyeur

Last week, Jonathan Creighton created a stir by performing nude in The Dance of Darkness. While female nudity is not commonplace, it has occurred in the past. This was the first nude performance by a male actor on this campus. The campus has been abuzz since. We at the Daily asked Jonathan for an interview to explore how it felt break new ground. Daily: Yo...

My Number Ch. 15: The Final Chapter

by ReedRichards on Sep 18, 2017
Romance

Exams were finally over, and the Big Day was approaching. I'd actually gotten in a couple of days of orientation at Central Bank, so that I could start for real on the 22nd, just two days after Dave and I got married. My mom came down to Lexington to pick me up on Thursday, May 18th, and now I wouldn't see my fiancée until our wedding on the 20th. Dave heade...

My Twin Sister is a Cheerleader Ch. 02

by Callicious on Sep 25, 2017
First Time

If you have not read Chapter 1, please read it first so you understand what is happening. If you are looking for a quick jerk and a lot of sex this is probably not for you. There is no actual intercourse in this chapter, although there is sexual activity. This is an exploration of an extremely shy young man who is taken advantage of by senior cheerleaders,...

The Little Thing Pt. 01

by Leopwriter on Dec 9, 2019
First Time

*** I love feedback. If you like the story, please let me know. - This is a work of fiction, any resemblance with real people or names is purely a coincidence. - One last thing: I'm not an English native speaker. I think my English is pretty good, but I can make little mistakes here and there, so please bear with me. *** We shared the same lift two or three...

Journal of an Older Eager Lover

by Silverstag on Sep 16, 2017
Letters & Transcripts

In two days I will drive 300 miles to spend the weekend with a woman I have never met. We connected through the internet via one of those ubiquitous matching services which are so popular these days and have communicated through e-mail and telephone calls. Our communication has been playful and insightful and just slightly sexual - nowhere near cyber-sex but...