Free Shemale Stories

Masturbation fantasies: Amanda, queen of the peep show

A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... read more

ThatEroticWriter July 24, 2019 91%

Masturbation fantasies 2: Looking for Amanda

Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... read more

ThatEroticWriter July 24, 2019 100%

Shemale Fantasy - Suck Fest

This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behi... read more

shemale lover September 13, 2011 100%

First Time Crossdressing with a mate part 1

It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I dressed up like a slut for the first time, I couldn't stop thinking about meeting another crossdresser for some horny mutual fun. I had been faithful to my ... read more

shemale lover July 21, 2014 84%

My Girlfriend's Mother Has a Secret

A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-). Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pr... read more

shemale lover February 27, 2015 98%

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%

A New Dawn Chapter 3

Tom and Dawn had been inseparable since their first fantastic night together, barely being able to keep their hands off each other. This was difficult at work, where they had decided to keep their relationship a secret. The management frowned upon office romances. This was especially difficult for T... read more

shemale lover March 31, 2012 100%

The Poker Game

I'm 21 and i'd always considered myself totally straight until towards finishing school. I started having more fantasies about cocks. I would not find myself attracted to guys but while watching porn i would always love seeing the cock as well as the girl, sometimes wishing i was the girl sucking it... read more

shemale lover May 4, 2012 100%

The Bitch Bites Back

Pamela stood huddled in the dark doorway, halfway down the back alley. It was cold and a light drizzle had settled in, the sheets of fine rain just discernible in the dull light of the single working lamp halfway down the alley. Pamela was in her mid forties and fighting a losing battle against t... read more

shemale lover May 12, 2012 100%

Dogging tv slut

It was dark enough now I thought. It was about eight o'clock on a warm spring evening and I was ready. I had started getting ready about three hours earlier. I'd showered, cleaned all those special parts, applied my make-up heavily and dressed. I was wearing a skimpy flower print top over a black si... read more

shemale lover May 22, 2012 100%

Satin Blowjob

I was soooo horny. One of my ultimate fantasies was coming true; I was in her bedroom... she was supposed to be away for the weekend and I had found my way into her walk in wardrobe. I couldn't help but take my clothes off. I had then run my fingers across all of her outfits hanging up. From her ... read more

shemale lover September 3, 2012 90%

Flight of Fancy

Boarding the plane I take my seat and cannot help noticing the beautiful young woman sitting next to me. She introduces herself as Mary Jane and I take her hand in mine feeling the warmth and softness of her skin. We chat and get to know each other as the plane takes off for the overnight flight. So... read more

shemale lover November 10, 2012 100%

A New Dawn Chapter 5

Tom's life was going well. He had a job he enjoyed, and apartment he was comfortable in and he had Dawn. He watched her in the mirror from the bed they shared as she applied her make up and smiled. Yep, things were pretty good. Dawn saw him watching her and grinned. "What are you smiling abo... read more

shemale lover March 31, 2012 100%

Biker Boys Replacement Chapter 2

It's now Friday afternoon and I am in the shower. The hot water is running over my naked body as I soap myself thoroughly. I pause for a moment as I soap between my cheeks before pushing a couple of soapy fingers inside my tight hole. I gasp, it's the first time anything has entered me this way and ... read more

shemale lover June 12, 2012 50%

A Ski Bunny is Born Chapter 2

My first real man. Hugs and kisses to everyone who contacted Kim and I expressing how much you enjoyed our first episode. This is the second part of our life story so far, and is the first follow up to 'A New Ski Bunny is born'. It recalls the first time that Kim and I included guys in our ... read more

shemale lover June 21, 2012 100%

Tranny gang bang

It was pretty dingy in here, the sunlight came through a old dirty high window and a single fluorescent tube did little to lift the overall gloom. An oppressive smell of stale piss also hung over the whole place. What was I doing in here? In truth I did not know but I was 16, horny and wanted to ... read more

shemale lover February 27, 2015 83%

Mongoose Hunting and the Dark Car

After my first sexual experience with a trans girl in school (Check out Biology of Music), it was a long time before anything else got me that horny again. Which is obviously understandable given how ridiculous that whole event was. This time instead of a trans girl cumming hot jizz into my mouth af... read more

terrifictim March 30, 2023 100%

I fucked my personal trainers ass for the first time

I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... read more

Madison Heights May 18, 2023 100%

Lola Chapter 2

Lola Chapter 2: A couple? It wasn't as if we were together. We had jerked off together once, and of course we slept in separate rooms, but I slept restlessly that night. Dreamed something scary that I couldn't remember in the morning. I didn't have work scheduled that day so I took it easy. When ... read more

BellaBeau October 5, 2023 100%

Edging lessons for Hannah

Hannah and I began spending our weekends together. She didn't have a job and I was always free those days so every Friday or Saturday night became sleep over night where we could be two 18 year old sissies, doing each others makeup, playing dress up and sharing our deepest desires. Now that our rela... read more

KaceyKlarissa January 25, 2024 100%