Transgender & Crossdressers Stories

12,569 results
Orientation
Length
Source
Infinite Scroll

A Wife's Surprise

by Aprilsdays on Jul 3, 2019
Transgender & Crossdressers

April's Amazing Day So, my story starts like most of us crossdressers, finding moms lingerie in the clothes hamper as a pre-teen and of course putting things on while getting those first feelings of excitement, sexiness, and that surge of adrenaline. Every day I became consumed with hoping against hope that when I arrived home, no one would be around so tha...

Eloise's Journey

by karen1947 on Oct 2, 2017
Transsexuals & Crossdressers

This is a fictional story. It is written from Eloise's viewpoint in first person. ***** 1. Hello all!! This is Eloise Schmidt. I haven't always been Eloise. I was named Brian at my birth. But by age 4, I found I liked to play with my Barbie dolls and wear Wonder Women underwear. I had an older sister (Emma) who loved to have me join her at tea parties...

Erika's Story Ch. 02

by Quantarx on Jan 20, 2020
Transgender & Crossdressers

This is chapter 2 of Erika's Story my first story series, If you have not read the first part it might be a good idea to go back and check that one out first. Also I would love feedback and constructive criticism so I can get better. Finally, please rate it at the end so I can see how well it is being received. Enjoy! *** Three months had passed since the...

Autumn by Marina

by ashleyw_xoxo on May 19, 2020
Transgender & Crossdressers

1. The Setup Marina and I had developed a friendly banter for over a year at work. She was a fit 26 year old, 5'8" tall, with curly brown hair dyed red to her shoulders. Early on I had asked her out and she turned me down. A few days later she confided that she was a lesbian. After that it was a rare week that I didn't teasingly ask her out again, knowing w...

Blossoming Shemale Ch. 03

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by tawnysuede's Reluctant Shemale: http://www.literotica.com/s/reluctant-shemale If you enjoyed it, I hope you'll enjoy this series. A note on political correctness: I have come to learn just a tiny bit about the transgender community, and by that I mean that I've learned that words such as shemale, transsexual and dickgirl are offensive...

The Kingdom of Hafizar

by Samuelx on Feb 12, 2019
Transgender & Crossdressers

The Kingdom of Hafizar, which is bordered by Kuwait to the north, the Kingdom of Saudi Arabia to the South and is considered the smallest of the Gulf States, stands at the doorway of progress and peril. The Kingdom has a population of three million inhabitants, most of them centered in the three major cities, Al-Mokhtar, Behar and Thobar. Ninety percent of t...

Hotel Encounter Pt. 03

by Jay876 on Sep 24, 2019
Transgender & Crossdressers

Jay gets on a bus and prepares to head back into town. Kyle had yet to respond and Jay was feeling lonely he needed some comfort. He didn't have any friends in Derby and Kyle was the only person he could turn to. As he sat on the bus, he felt like crying in the bus on the way into the city center. Jay got off the bus and headed back to the hotel it was onl...

Hotel Encounter Pt. 02

by Jay876 on Sep 24, 2019
Transgender & Crossdressers

Jay awoke his body being spooned by his Daddy. It's 3 in the morning. Jay can feel Kyle's hard cock pressing against his ass. He needed Kyle inside of him again. So, Jay turns around and kisses Kyle on his forehead. He smiles at Jay. "How was last night?" "Fun." Jay says smiling back. "You know I've never been with an Indian before." "How was it." "Best...

Truth or Fantasy 07: Photos

by 1sfshermale on Sep 24, 2019
Transgender & Crossdressers

At the local scenic look out, I held up my new white phone "Would you mind taking a few photos of me for my collection?" I asked the handsome gentleman wearing a red Titleist golf cap. "Not at all, in fact, I was trying to figure out what to say to you." he replied eagerly. "When I saw you in your pink dress, I knew I wanted to meet you. You are gorgeous....

Don't Come

by AlinaX on Apr 3, 2019
Transgender & Crossdressers

"Don't come," she orders, and I sigh audibly with frustration. I'm all for a bit of orgasm denial - the resulting climax can be spectacular, true, but also it's exhilarating to linger on the precipice, every fibre of my being exquisitely tense with need. Her delicate, lingering, teasing kisses make me burn. Her mouth descends on my breast and I writhe in an...