Free Shemale Stories

Loosing my virginity to Shemale Preet

This story is of may be 2017. When a shemale escort took my virginity n fucked me. I am not new to shemales. I hv been attracted to shemales since 1999 when first time I got internet at home. Suddenly while browsing i saw shemale website n instantly i was hooked to it. Well how I met my first ... read more

Stud4Shemale February 20, 2021 100%

Daddys Bride-to-be

Daddy rings my doorbell. I was waiting impatiently for him, dressed appropriately...today is a special day...today I promise daddy to marry his cock. I am dressed in a silky white wedding dress. Very short and tight, with shiny beads and pearls, along with a veil covering my face, and long white ... read more

lea1234 October 7, 2014 100%

Audry: My Guide to a New World

For a long time, I've known I liked guys. Well, to be more accurate, I like cocks. Guys, I really don't find sexy. Women, I find sexy. A good set of breasts or a nice round ass with a little waist and big round hips will make me hard in an instant. When I look at a guy, I don't get turned on, but sh... read more

shemale lover December 29, 2011 88%

How I sucked my first shemale cock

It was the beginning of the year 2023, in January, three days after New Year's Eve. I was driving home in the morning from a party 100 miles away from my hometown. On the highway, after going half the distance, I received a notification from my dating app, and I was like, "Oh, a new match", I'll che... read more

cock&heels69 May 25, 2023 100%

Camming Down the Rabbit Hole Ch. 12

We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... read more

Dani_does_Dallas May 9, 2022 100%

First Cross-dressings Loosing Anal Virginity

It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... read more

Trapbomb1 July 29, 2022 100%

Crossing lines

It had always been a fantasy of mine. I have very feminine features and long natural straight brown hair. Which recently I had shortened to chin length. I have been dressing in womens clothing now for many months and had decided that this was the night in which I get made up totally and head ou... read more

Zöe from Kingston February 4, 2019 94%

First Outdoor Fuck

Sat in my office with nothing to do was making me tired there was no customers to serve which was slowly driving me mad, what was worse was the hot weather outside which always makes me horny, knowing I had all my girly clothes in the boot of my car was making my cock twitch in my cheap nylon work t... read more

shemale lover December 19, 2012 90%

Outdoor Tranny Sluts Lust

I wake up really early one morning with my cock throbbing hard under the sheets. I got a white camisole on. Out of bed i go with a desire to vouyer and masturbate somewhere around my home. I'm home alone so i head out to my garden with my cock bouncing up, down & dripping cum. It's about 5am... read more

Tracy Bel February 14, 2023 80%

Ginger loses her virginity

My friend's father, Mr Webster, had turned out to be anything but the pillar of the community he pretended to be. Despite his regular Sunday church attendance with Mrs Webster, it transpired he also enjoyed the company of other men. He was certainly enjoying me, and within a few weeks I had fal... read more

Ginger__57 March 26, 2018 90%

HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional

It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... read more

CDDIXIE4U January 8, 2019 91%

Falling For My Roommate Chapter 3

If there's one good thing that college taught me, it was that concentrating in class the day after getting your first blowjob is very difficult. I must've gotten aroused at least four times during my first class, and a couple during the next. It was a true pity that I wouldn't be back in my room for... read more

shemale lover May 23, 2012 60%

From a 50's virgin to a Mature good for all

***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... read more

hippocampus_171 January 11, 2023 100%

I Love To Love You

I Love To Love You Baby By Sabrina G. Langton Author's note: I have published this story on two other sites. I always said it was slightly aurobiographical, but reading it back it is a pretty accurate account of my summer of '88. There are only 3 things that I changed. 2 are itsy bitsy tiny deta... read more

Brina Giselle September 24, 2023 100%

Special Shemale Fun

Everyone in the hallway jumped slightly, turned and quickly looked at the tall girl near the sound of the slamming locker. Satisfied that there was no crisis at hand, the kids at the school mostly went about their business. Of course, there were the few admirers that glanced at the girl at the locke... read more

shemale lover February 6, 2012 100%

Losing my virginity

I have always thought that sex with a shemale would be amazing. I dreamed about sucking and fucking a hot gurl. When I was a freshman at university I got on Craigslist and saw an ad for a t gurl who was traveling through town. I sent an email and she responded very quickly. We made plans to grab dri... read more

lepomme February 1, 2018 90%

She also conquered my soul...

Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... read more

hippocampus_171 November 22, 2022 50%

First time with a Shemale

First off this is a true story. I lost my virginity at a young (i think 13 or 14) age so sex is always been something usual for me. As far as how I lost my virginity... thats another story. I have always dated older women that were openminded, bi-sexual and down right sluts. I have been in strange c... read more

London CD October 11, 2011 66%

Uncut sucknsuck

I used to work at a place that has a locker room and showers. A guy I worked with had a locker right next to mine. Everyday after work I would find my way to the locker room and would be hit with an over powering smell of sweaty balls and I would sit down on the bench in front of my locker. My frien... read more

Uncutsucknsuck March 5, 2018 30%

HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH

It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... read more

CDDIXIE4U January 8, 2019 100%