Free Shemale Stories

The Big Tiddy Goth Girl

Hannah and I went to the pool in my apartment complex. This was my first time dressed as female in public and I was loving my new, feminine tan lines. To keep a long story short, while tanning we were perv'd on and approached by a guy calling himself Mark. He was desperate for our attention and fumb... read more

KaceyKlarissa February 23, 2024 100%

The Big Mature Shemale Next Door

The Big Mature Shemale Next Door SugarandSalt "Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mir... read more

Gwapo67 May 3, 2022 100%

The Girl Next Door Ch. 01 by derezzed ©

Michael was your average 21-year-old college student. He was on his way home from college for summer break after finishing his finals and looking forward to a few months of relaxation. Driving home Michael reflected on his past three years of college. It had been a great junior year. He met a lot of... read more

StevelovesTgirls May 27, 2019 86%

The Girl Next Door Ch. 01

derezzed Michael was your average 21-year-old college student. He was on his way home from college for summer break after finishing his finals and looking forward to a few months of relaxation. Driving home Michael reflected on his past three years of college. It had been a great junior year. H... read more

Gwapo67 May 13, 2022 94%

Daughter Finds Out Mum Is A Shemale

I had a free period at the end of my school day so I decided to come home a bit early. I got home and headed upstairs to my room when I heard a faint moaning coming from the study. I leant in towards the door and I couldn't hear anything. I opened the door to make sure nobody was in there and what I... read more

shemale lover July 27, 2012 72%

A Dickgirl Part 2

Ginny was mortified. For the first time in her life she hated her body. Why the fuck did she have so little self-control? Why couldn't she hold her body back? Why couldn't she be like normal girls? She cried all the way home, her tears drenching her shirt. She stopped by the time she got home, bu... read more

shemale lover February 27, 2012 100%

Tortured by the T-Girl Tutor

Duncan didn't quite know how to handle it. He'd planned on a quiet Winter Break. Sleeping til noon, watching too much television and eating tons of junk food. That kind of stuff. He had a whole two weeks off from community college. At school, he was an outcast. They say life gets better after hi... read more

shemale lover December 18, 2012 94%

Big Dick Alessia Visits Dallas

Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... read more

darrell April 20, 2022 100%

Buffy the Shemale Vampire Slayer Part 14

"Let's get this over with," Buffy suggested. "The sooner we start, the sooner I kick your demon ass." Baphomet smiled. "You will fuck the witch," he said, "while I fuck you." Buffy shook her head. "Willow's my best friend. I can't-" "Th... read more

shemale lover August 23, 2011 80%

Intense

Holding to my word, I didn't let the incident with Billy and his friends scare me away from Bailey; I kept seeing her, even after the beating I took. To be honest, I'm not sure if he was trying to lay low or what, but Billy seemed to keep his distance from me for a while...thankfully. Bailey and ... read more

Verpa October 21, 2019 100%

Roberta, Molly and Ed

Friday "Commander Cromartie?" Lt. Commander Edward Cromartie, USN, turned toward the voice that had spoken his name. He saw two female naval officers, a tall willowy light-skin Black woman, and a short Asian one. The Black one was wearing the uniform of a full commander, the Asian of... read more

shemale lover September 4, 2012 100%

Shemale Porn Photo On The Wall Of Her Room

She was a truly hot shemale that I’ve been seeing for a couple of months now, from time to time. She had some really big tits and a dick that didn’t really get in our way much. It really wasn’t all about the sex. I loved talking and even cuddling with that girl. We talked about ... read more

shemale lover June 12, 2016 68%

The Game 2

That next morning again Ada and I went down for breakfast and the table was smaller, It wasn't as grand as it had once been and to every guy at the table was now at least two girls. We had our normal breakfast and for once there seemed to be a little more chat between everyone, I think after bei... read more

chris1989r January 24, 2022 100%

Adventures of Shemale Sandra Part 2

Sandra thought about Jeff all through the next day. He had been her first, and she could still recall their experience as if it had happened only moments ago. She could feel his rough hands on her tender flesh; his sweat falling in beady drops on her soft belly; his stiffled grunts echoing in her ea... read more

shemale lover September 3, 2011 66%

Meeting Amanda

I’m a happily married man. My wife Tess and I have been together since we were teenagers. We were each other’s first real lovers and being in our mid-thirties by now, we still madly in love with each other. Tess and I always are very honest and open to each other. Both in normal life and sexual... read more

rforasht July 20, 2022 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%

The Chronicles of Drodge Mallea

Drodge awoke feeling fuzzy headed and stiff. Actually, "awoke" wasn't quite right -- "came to was more like it. She sat up in the lavishly furnished boudoir, stretching her athletic 6-foot frame as she did. Running a hand though her short, thick copper locks, she slipped out of the... read more

shemale lover October 24, 2011 50%

Melissa

I'm a Japanese in my early forties living in Japan and I met Melissa online about a year and a half ago when looking for someone to chat. She is a black, 6 feet 2 inches tall, around 160 pounds and therefore a slim and beautiful transgender girl in her mid twenties. From Brazil, she is very friendl... read more

cttyy February 24, 2020 87%

The Experience of a Lifetime

My divorce was hitting me really hard. My wife outgrew our relationship and started living her own life and I had a front row seat to everything. My heart and life was upside down. I didn’t go out anymore. Friends and family both told me it was time to get my life back on track and start living ... read more

therefill05 November 30, 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%