First Time Crossdressing Stories

351,059 results
Orientation
Length
Source
Infinite Scroll

Sine Equals Cosine

by elsol on Sep 2, 2017
Erotic Couplings

----- Como siempre, para mi mama. (Like always, for my mother.) ----- I did not want to be there, especially with the guitar weighing me down. The crowd made me uncomfortable as soon as I opened the door. I had made a decision though; my discomfort meant nothing. I looked around the off-campus hangout; it was surprisingly large for a non-franchise coffeeh...

Sexy Sally, My Slut Wife

by Jigs on Sep 18, 2017
Loving Wives

Authors Note: This is a story once published at another site under the name Sexy Sally & Boss Bob. For its appearance on Literotica it has been rewritten, its plot amended, and its category changed, although it does return with the original characters and parts of the original story. I have done my best to make it as fresh and interesting to those who may ha...

Shared Love

by Kojak01 on Jul 13, 2020
Romance

Author's note: This is not a typical romance between one man and one woman, but a romance none the less. If you don't want to read about a three-way-relationship (two women - one man), please stop reading now because otherwise, you'll get disappointed. With the focus of the story being on the relationships, I decided to nevertheless put in the Romance catego...

Cathouse Tuesday! Ch. 02

by MormonChicks on Sep 15, 2017
Loving Wives

What would you expect if you bought your wife a whorehouse? *********** I slept on the way home wearing that blue dress. Porter's choice! I probably should have realized with all the cum Nate had loaded into me that I'd wake up in a puddle. I had lifted my dress above my waist expecting such a surprise when I awoke. Thank goodness for leather seats. Eleven...

The Benefit of Friends

by JackNimball on Sep 13, 2017
Erotic Couplings

This is a work of fiction. The events in the following tale are figments of my imagination. All characters are REAL; however the names have been changed to protect the innocent. I encourage everyone to send comments, positive or negative, to me. Prologue: Natalie I guess it was mostly my fault. Maybe if I had not worked so much. Maybe if I had not been so...

Graduation Summer Ch. 15

by 32aa on Mar 16, 2020
Romance

The week continued. Rita and I got together at her place Wednesday night for some 'quiet' time in her basement. The three of us met up after work Friday night. It was raining so we spent the time again in Rita's basement, 'playing'. I went home with a severe case of blue balls. Chris and Rita were quietly planning on the next night's adventure. I was oblivio...

Sex and a Single Girl Ch. 16

by sue_in_surrey on Sep 13, 2017
Erotic Couplings

Tom and I had reached the end of our holiday. When I arrived at Young Island with my brother we had promised not to have sex with each other again. Instead, upon spotting our new friends and lovers-to-be having sex in the dark in an adjacent hammock, I had broken my vow to Richard and joined in the sexy fun. Soon swapping partners, Tom and I enjoyed days and...

A Bad Influence Ch. 02

by MrRobbur on Sep 16, 2017
Loving Wives

Note: It will help to please read "A Bad Influence" before you read this story. Readers have requested the wife's point of view of how it all happened. So here goes. Also please continue to send feedback (good and bad) or I'll never learn from my mistakes. (Suzie's Story) This story is being written from my prison cell. It is a cautionary tale we could...

Cottage 69 Ch. 03

by Wayne_Richardson on Sep 11, 2018
First Time

This story is entirely fictitious; enjoy. ***** On Monday morning the rumour spread like a bush-fire through the Cedar Hill high school; especially among the boys. "Have you heard? A junior boy claims to have seen up Miss Lambert's dress last Friday. He said she wasn't wearing any panty and her pussy was bald!" Frances (Fanny) Lambert and Janette (Jan) Pr...

What Happens in Spain Ch. 02

by BenLong on Nov 18, 2019
Erotic Couplings

Big Friends and Little Friends ~ "Cervesa?" Ryan asked pointing his finger at each in turn. Four Si's and yeses turned into an order for "Cinco Cervesa's." "You know a bit more Spanish than just "where is the bathroom"," Irene teased, as he set a bottle in front of her and slid into the seat beside her. He laughed. "Yeah, but not a whole lot more. I too...