Free Shemale Stories

It doesn't get any better than this!

15 years ago, I went into my older brother's room to grab a porno mag. He had stacks of them all over the place. I wasn't too choosy. I picked the magazine off of the top of the pile that was closest to his bed and went into the bathroom. My usual routine was to open the mag, find a babe, pull out m... read more

shemale lover May 17, 2012 57%

Teen Sissy getting ready to give herself to daddy for xmas

Hey Im Rosie and im 22 from the UK im a aspiring sissy slut and i have been getting myself getting my whole body smooth ready for my daddy ready for my daddy for xmas / new years i have found out he has been watching ts / ladyboy porn for a while now and i have allays wanted to become his sissy slut... read more

English Rose December 23, 2016 56%

The Truth about The Fate of Mariana Cordoba..still searching. .

Just yesterday, yet another strange FACT has emerged. And it is not the purported fact which is stated in this new purported information, but the FACT that it is the Same Person posting about Mariana and making the same claim that Mariana has passed away. . . . and THAT person making this statemen... read more

Katrina_Electrika January 8, 2019 89%

Exposure, Disclosure

The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... read more

the greatest liar June 18, 2019 100%

Shemales I'd like to fuck

It goes without saying that I would fuck any of the girls whose vids I've posted, but some stand out (no pun intended). First there is Jennifer Pistoludo - very pretty, slim, a great ass, perky little suckable tits and a monster cock. Then there is Bianca Freire, I love everything about her. Lastly ... read more

bigtranslover January 31, 2014 56%

First Time Having Sex With A Shemale

Ok let's begin so I was walking down the street going to the store one day I saw a woman and her daughter moving into a house they had some heavy boxes that they need help with. At first I thought she was white girl but when I got closer to them they we're Asian becuase i only saw the back and they ... read more

bigtranslover May 21, 2011 78%

How i became a Transexual Tart

This is my true story of how i became a Ladyboy. I grew up in a small town in the UK, Where i lived there wasnt many females in the same age group as me and my friends most of the girls were much older than us which left the boys sexually frustrated alot of the time. My best friend Alan was always f... read more

shemale lover August 9, 2014 85%

Sucked out every last drop

Here's an very exciting story from our reader Salty47 who have given his ladyboy GF a blowjob for the first time and then sucked out every last drop of her delicious cum. This post is not at all like my first experience. We met and became good friends. I never gave a thought to her body parts - b... read more

shemale lover January 23, 2015 93%

A succulent shemale cock in my mouth

Not only the readers of our ladyboy blog love jerking off to our shemale sex stories, some of them are also willing to share. A guy named Steve was always curious about how a shemale cock would taste in his mouth and he just had to let it all out. TFS, Steve. I have always wanted to know what it ... read more

shemale lover February 17, 2015 80%

Sleazy shemale fantasies

Sifting through the comments that readers leave at Trans Ladyboy, i have found two really hot shemale fantasies that I would like to devote separate space to. They are both written by two horny guys, wyocock and Eddie, who dream about being with shemales all days long (the only difference is that E... read more

shemale lover February 19, 2015 100%

Jane from Guess Bar

Again an awesome reader submitted story. One of our lucky readers says he had a great fuck with Ladyboy Jane. Was in BKK in Oct 07 looking for love in all the wrong places. In particular one sexy cum kitten called Jane from Guess bar, Sukhumvit soi 1. When i arrived i found a complex of beer bars... read more

shemale lover April 25, 2015 88%

One of my real life stories with a post-op

This wonderful story was published at our forum, and, honestly, it was the first sex story involving post-op tgirls that I read, and I can't hide the fact that, although the girl had no hard one, it was still very exciting! Thanks for publishing it man! I was on vacation in Japan, and I went out ... read more

shemale lover June 5, 2015 69%

Got more than he bargained for

This story was written for Trans Ladyboy by Brandi, a hot dominatrix and a phone sex operator. She says guys often call her to share their tranny fantasies with her, one of which would be getting dominated by a tranny, and, you know, she's really good at that! Call her for this phone fantasy (1.99 a... read more

shemale lover June 7, 2015 88%

Ladyboy Surprise - Part 1

It has been many years now, but I can't seem to forget what happened to me. I was as a young seaman in the Navy. I still wake up at night rock hard thinking about it! I am happily married now to a good woman and have a few kids, but I can't get this image out of my mind. We had been out to sea fo... read more

shemale lover October 13, 2015 90%

What I dream about

I'm shortly to embark on a trip to amsterdam in the new year and am very excited for one thing in particular, the opportunity to come across a real life shemale! I've been a massive admirer of shemales for a long time now ever since I first saw one. I don't remember exactly how I came across them b... read more

shemale lover August 11, 2011 100%

How To Spot A Shemale

More and more men are taking female hormones, receiving breast implants, and undergoing sex-change operations to become "women." Some start these procedures while they're still teens and more than a few mimic women so well that they can use the ladies' room without raising an eyebrow among... read more

shemale lover August 18, 2011 25%

Nicks Shemale Experience

Nick had discovered he had a thing for shemales 4 months ago after stumbling across some pictures on the Internet of a really hot ladyboy from a porn link site. This sort of thing had never turned nick on before but looking at pictures of the small-breasted brunette really made his dick hard. It did... read more

shemale lover August 22, 2011 57%

Shemales: An Appreciation

Androgyne, futari, girly man, he-she, intersexed, hermaphrodite, kathoey, ladyboy, newhalf, shemale, tranny, transgender, transsexual-there are lots of names for chicks with dicks-maybe too many. As whenever such a case presents itself, it is helpful-no, mandatory-that one define one's terms. As use... read more

shemale lover August 30, 2011 50%

Gargantua

Women do not have penises or testicles. These sex organs are specific to men. As the boy in Kindergarten Cop demonstrates, even young children are aware of this most fundamental fact of life. However, in the genre of erotic fantasy art known as futanari, hermaphroditic "dickgirls" defy nat... read more

shemale lover September 12, 2011 44%

Sex with Shonda

I'm a workaholic by nature. I love my job but that's not why I work so much. I work long hours simply because when I get home I don't quite have anything productive to do. I just sit down in front of the television or I chat over the internet. Life at home is dull so the best solution seems to be en... read more

shemale lover September 18, 2011 50%