Free Shemale Stories

A Fetish Doll For Mommy

There is a very old saying," Be careful what you wish for because you might just get it." My fathers name had been James Bradley. He had been a CEO of a top Wall Street investment firm. My father didn't climb to the top by being a good guy. He was a total prick who would stab anyone he had... read more

shemale lover November 13, 2011 100%

First time Crossdressing

I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards that allow members profiles and posting messages. I also post to local groups in my area that allows one to post messages to a small geographical area or to a distant user g... read more

shemale lover July 17, 2013 37%

Regina’s Double threat.

Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... read more

Regina10 February 8, 2022 100%

Barbie Jo Adventures Part 2

Friday Night After work I picked up the pictures and went home to get ready. I got the call from Wanda this afternoon at work. She first apologized for kicking me out of her house last Saturday night, Halloween, without letting me clean the cum off my face. Knowing that I would have had to walk h... read more

shemale lover February 17, 2012 75%

A Certain Perception

Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... read more

shemale lover February 23, 2012 33%

My first Theesome

I'd been flirting with Clare for a while in work. I always thought she would be one of the girls that would play around in work, but never actually go through with anything. It was a slow day in work and as usual the subject came round to sex. We were having a cheeky conversation about fetishes a... read more

cdleesa June 1, 2020 90%

Emily's welcome

Since embracing the feminine me I’ve been on a bit of a shopping spree, it’s tough to be a gurl who hasn’t had anything really nice to wear for so long. In particular I love to buy pretty panties which keep my clitty nicely in place, but also rub up against my pussy as I walk – with nobody any the ... read more

EmilyTG July 4, 2019 84%

Office Policy

“Ok ladies and gentleman, please put your hands together for the beautiful and talented Erika!” the DJ’s voice rang out over the thumping alternative beat as the object of my lust strutted to the stage. Erika’s saucy red curls bounced on her head and on her soft porcelain whi... read more

shemale lover August 30, 2012 80%

Our special trip

John and I were having a nice relaxing afternoon cuddled up on the couch watching TV. Our relationship was shifting from all about great sex to enjoying the time we spent together just being ourselves, with me dressed up of course, and the sex seemed to me to be more loving. I'd still seduced him at... read more

shemale lover February 22, 2012 100%

Feminized By My Mother Chapter 2

My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed. "I ho... read more

shemale lover July 24, 2012 87%

The Girl Next Door Ch. 03 by derezzed ©

Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Alexis's arm casu... read more

StevelovesTgirls June 11, 2019 100%

College project surprise

So this story happened while I was still in college and remains without doubt, the craziest, most exciting experience of my life. So I the story begins one day when I walking to class. I went to a big university so my walk was quite long, and the first 1/3 was just through off our campus housin... read more

Jsmithsub September 16, 2020 100%

The New Nii

The bedroom door opened and the two lovers walked down the hall into the living room side by side. Deena was wearing her nightshirt that she wore a lot, and Jeffery was nude, and he picked up his clothes that I had put on the chair and began to get dressed. “Jeffery is going to go and get dinner an... read more

Setinkhan May 28, 2021 100%

Shopping plus extras!!!

Hi, so as you can probably imagine I buy a lot of underwear and have a few favourite places to shop. My favourite by far is Ann Summers. The range is great and the staff are so helpful . Anyway back to the story. So I decided to go get some new underwear to see in the new year, I got myself up and d... read more

Samantha Jewels January 6, 2023 100%

A Game within a Game Part 1

Epilogue Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter. Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fas... read more

shemale lover March 5, 2012 100%

Something For Everyone

Josh pulled slowly into the driveway and parked the car. He made as little sound as possible as he closed the car door, and took the same care as he entered the house. He was more excited than he had ever been, but didn't want to spook the people inside. His wife Penny had called him before he left ... read more

shemale lover October 20, 2011 100%

The Birthday Gift

I wasn't really looking forward to my 30th birthday. It's not that I was worried about getting old. Trust me, I'm not one of those guys who go looking for new gray hairs every week. Besides, I was plenty happy with my body at the time. I stood about 6' 2" and had a pretty muscular build. I wasn... read more

beedoubleuthree October 21, 2011 100%

Best of Both Worlds

Keith, 37, and Linda, 35, are very liberal people. Both enjoy sex although Keith had bi-sexual fantasies, he would never act on them, but also thought his wife was maybe a little shy and too submissive. Keith was a fairly attractive man, but his wife was still gorgeous at her age. With her long b... read more

shemale lover May 9, 2012 100%

TG Girlfriend moves in (part 2)

My wife Lydia and I have been married about 9 months, we have a very close TG friend, Joanne, that lives next door and every once in a while, we get together, and all go out and enjoy. We have had sex together, and when Lydia is away Joanne, and I are together at every opportunity. Joanne and I work... read more

Jon Paul January 21, 2022 80%

One experience with two black men

Hello again this is EvA…I am a 40 year old tranny. I do not consider myself a cross dresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine lady boy. I have been taking also hormones for 4 years, on and off and I already saw many changes&h... read more

shemale lover May 16, 2013 100%