Transgender & Crossdressers Stories

12,569 results
Orientation
Length
Source
Infinite Scroll

The Parking Lot

by TalesToTell on Nov 18, 2019
Transgender & Crossdressers

He sat in the semi dark of very early morning in his car. The parking lot around him held a few cars here and there, but was still mostly empty. His heart beat slightly faster than usual, part fear, part excitement. The message he had received had told him to meet here in the parking lot early, and alone. It had mentioned that they knew about the incident he...

It Had Been Far Too Long

by lynntg0444 on Nov 26, 2018
Transgender & Crossdressers

For me, the ultimate feeling of femininity happens when a man is inside me, and It had been far too long. Over the last few years, my wife had effectively shut down my indulgence in the hobby of crossdressing in public - mainly at bars frequented by the transgendered and their admirers. She only suspected how far I had taken it. My opportunity arose when she...

Letter to My Queen Ch. 02

by hyperpress on Mar 25, 2019
Transgender & Crossdressers

"Don't pretend," you said. "Tell me," you said again. "Fuck my mouth with your toe," saying it aloud to you made me dizzy. "Stroke your penis," you said. "Close your eyes and imagine a cock in your mouth." "Nod your head if you can see yourself." "As you pan the camera back, see yourself on your knees. Between a man's open legs, his feet resting on the f...

Silver Fox & Barely Legal Twink

by puzziboi on Mar 30, 2020
Transgender & Crossdressers

Jim O'Connor was straight as a board. The 60 year-old with the crew cut white hair and stubbly face voted Republican, owned several guns, drove a Dodge Ram pickup, and was a retired high school teacher & baseball coach. In fact, the married father of two adult daughters with four grandkids had amassed 19 consecutive winning seasons as head coach. His record...

Basement window uncovered

by showitall2u on Feb 3, 2020
Transgender & Crossdressers

Recently we had some work done in our basement. The basement window had been uncovered while the work was being done. We left it that way for a few days, so when I went down to work out it was still uncovered. I didn't give it much thought as I turned the lights on and set up my Bowflex for my workout. As I was alone, I slipped into panties and a bra and a...

Mail Order Bride

by JaxRhapsody on Mar 2, 2020
Transgender & Crossdressers

"You really went and got a mail order bride, are you crazy? What if she is some psycho, or is just using you to get in the country? That's a big risk you're taking," Geoff exclaimed. "No worries, I found a website where you get to talk to the ladies, it's a pretty deep vetting process. For months now I have been talking to her, I felt it was my only choice,...

CD Fun Day at the Beach Pt. 01

by candypantscreampie on Jul 30, 2019
Transgender & Crossdressers

It was a warm sunny week day morning in February this year; and i had a rostered day off, so i decided to head to the local nudist beach to catch some rays and take a skinny dip in the beautiful blue waters... I quickly gathered some essentials for the trip, like my bikini, towel, sunscreen and other assorted items... and headed for the door... The drive t...

Hotel Encounter Pt. 01

by Jay876 on Aug 20, 2019
Transgender & Crossdressers

Jay was a 5 foot 10 Indian boy, he has longish hair and he is a little chubby. And this is the story about how he lost his virginity. He was sitting at home browsing through the gay apps. His hand slowly rubbing his dick. Just enjoying the erection. When suddenly he received a message from an older white man. Jay had always fantasied about being with an old...

Destiny Fulfilled

by cannyjess on Aug 27, 2019
Transgender & Crossdressers

I had secretly cross-dressed since I was 6 or 7 years old. The compulsion never goes away and had stayed with me throughout my life. My marriage eventually broke up 5 years ago. Not because of sexual issues but because we wanted different things from life. It was not long before I started a new relationship with another beautiful woman. The sex was great how...

Being Chris's Slut... Pt. 01

by usemetoday1962 on Jun 25, 2019
Transgender & Crossdressers

Chris had now decided that when we played he wanted me to be his slut. He had inherited some money and decided to purchase a small home. He knew i could help him do work in it so the house he brought had an unfinished basement. First thing he wanted was a wall splitting it in two so one side could be a play area and the other a mancave. But instead of a door...