Free Shemale Stories

She lied ........ Part 1

I had walked into this bar on Castro St. in San Francisco, not realizing that it was a place for transsexuals. I chatted up with this super sexy bartender dressed in all lime green. We made small talk & she invited me up to her place after work. Being that she lived only 4 blocks away & it was a... read more

Curious_billy April 14, 2023 100%

A true first time.

I want to preface this reiterating that this is a real story about my first ever experience with a shemale. It's a memory I will hold forever as it was everything I could have hoped for and, as I may share in the future, lead to other experiences, too. A little history of before the first meet ac... read more

Gtaaddict3 November 21, 2023 100%

Beryl's birthday suit

I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... read more

Beryl December 12, 2023 100%

Regina's Vagina dreams

I think I wanted to be a female from birth. I once looked through a girlie magazine out of curiosity. I had impossible dreams and I longed to trade genitalia with them. I have always fantasized about my Vagina when I was younger. It was during those times that I would drift into my own private world... read more

Regina10 March 1, 2024 100%

All Night Forced Sex Part 7

When I finally awoke there was a woman standing over me with a very sinister look on her face and with something in her hand. When i noticed i was just laying there i tried to get up to run away and she pushed a button on the device that and all i felt was an agonising pain in my balls. I immediatel... read more

shemale lover October 10, 2011 100%

A T-Girl Fairy Tale

Jared tossed the last bit of horse manure onto the highly stacked wheelbarrow. With a heavy sigh he gripped the handles and lifted. His muscular arms strained and bulged as he pushed the unwieldy load out the stable door to the large pile where he would deposit it until it was needed for the gardens... read more

shemale lover October 26, 2011 50%

They Were Right

They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... read more

shemale lover December 29, 2011 87%

She-Male Pimp Daddy

I’ve been working the streets for a long time and I know all the ends and outs of the flesh market. I have six she-males that work for me and I get 50% of everything they make plus all the sex I want, any time I want it. I make them work seven days a week rain or shine. I buy their clothes ... read more

shemale lover February 5, 2012 50%

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%

Becoming Her Bitch Chapter 2

I can feel the toe of her high heels sliding under my balls. I'm on all fours positioned right over it. The big black cock is lubed up and pressing against my back door. I try to relax. I try to let it in without clenching up. It'll hurt if I clench before he's in all the way. "Don't worry a... read more

shemale lover March 17, 2012 80%

Enchantment of the Shadow Realm

It was a enchanting night. The moon was full. The street light reveled an other worldly stream of fog through what I could see of the dark forest. Unfortunately I was having a hard time appreciating all this beauty. I was stranded. I had missed the bus and had no way of getting back to my hotel. I h... read more

shemale lover April 14, 2012 100%

A Night to Forget

The day started out like every other day. Woke up, dragged myself to the bathroom; Stepping in the shower, (I sleep in the nude...) still not fully awake, I let the water cascade over my head. Mmmmmmmmmmmmmmmm, I closed my eyes and could feel the water flow over me. I pushed my hair back off my face... read more

shemale lover April 23, 2012 90%

The Only One

After talking to her online for several hours she invited me over to her house. I got dressed, jump in the car and drove over. I must have been overly excited because my cock was raging hard the entire drive over there. The house was gorgeous, and huge. I thought to myself that this house had to ha... read more

okctshunter August 18, 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%

First Time Sissy Maid

I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for... read more

shemale lover October 27, 2012 70%

Proud To Be A Sissy Chapter 1

I had just turned eighteen and only had two months of high school left. My marks were good and already had a possible placement in a university where I hoped to get a new start. I was so looking forward to getting away from all the shit that life had forced on me in this little hick town. Usuall... read more

shemale lover December 23, 2012 100%

Proud To Be A Sissy Chapter 4

As usual, Mr. Clark was sitting in his recliner when I went into his house. "Good morning daddy," I beamed kneeling before him. "Morning," he grumbled but smiled and said, "more like afternoon." But you do look sweet." "Thank you daddy," I rep... read more

shemale lover December 24, 2012 100%

White fuckslut Tgirl & 3 BIG BLACK COCKS Initiation

You lucky, slutty BBC Tgirl fuckslut, I envy you soooooo much. This is the most erotic and best BBC story on this web site. Pleeease keep writing about your BBC fantasies. What a bargain to get gangbanged by about 30 big black studs for only 15 Euros. I loved it when you begged them to fuck you.\r\n... read more

TgirlJill4BBC June 3, 2013 71%

Why you should never cam

* Sorry for the poor writing but since it is the summer and I am taking sometime off to reflect before starting school next year I thought I would write up about what had happened to me the summer before. It is currently a work in progress and if spot any spelling mistakes or errors feel free to cor... read more

jennychen September 2, 2014 87%

Riverbank Tranny Fucktoy

Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river. It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site. I had been chattin... read more

shemale lover December 3, 2014 90%