Free Shemale Stories

Aunt trip

In 2013, after almost three years of service in Afghanistan, George Madsen, a gay Royal Navy communications petty officer, retired. His experience in the distant deserts had left an indelible mark, the memories of friends lost and challenges faced still burned vividly in his mind. Coming home was n... read more

Rebba April 25, 2024 75%

The Girl Next Door Ch. 03 by derezzed ©

Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Alexis's arm casu... read more

StevelovesTgirls June 11, 2019 100%

The game show,

One day i was looking through a number of competitions and trying to find a way to make some easy quick money. A number of applications were sent, mostly for junk i didn't need or for competitions I knew I had no chance of winning. For example, the types you get $30,000 for answering the easiest que... read more

chris1989r January 24, 2022 100%

Male or Shemale, Still a Slut

Part 1 My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond ... read more

shemale lover December 20, 2012 100%

Girl from Uncle

Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... read more

Regina10 February 14, 2024 87%

Pune crossdresser Night Girl

Hi friends, I hope you liked my earlier stories. This is my new story about a lady boy / crossdresser / sissy boy. Around 2 years back I came across a profile on Planet Romeo with name Nightgirl. I sent her message that i found her sexy and attracted to her and wanna meet her. I am alway... read more

Stud4Shemale May 22, 2017 69%

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%

The Guy At The Pool

The Guy At The Pool Stepping out of my hotel room for a smoke I saw two young guys at the swimming pool which my room overlooked. One of them was standing outside the pool speaking to the other guy who was in the pool. The guy beside the pool immediately caught my attention, his shirtless bo... read more

pennypenny October 21, 2019 76%

The Girl Next Door Ch. 02 by derezzed ©

Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the sunlight that h... read more

StevelovesTgirls June 11, 2019 92%

The Girl Next Door Ch. 02

derezzed Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the s... read more

Gwapo67 May 13, 2022 100%

My Romantic One Night Stand with a Beautiful T-girl.

My Romantic One Night Stand with a Beautiful T-girl. A friend of mine landed a gig DJing at the well known dance club in West Village of New York City. She invited me to check it out. Why not, I had no plans that weekend and she can put me on the VIP guest list. Which means I don’t have to wai... read more

My Shemale Attraction June 11, 2019 94%

Casino Girl

I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... read more

Jon Paul January 3, 2022 100%

Lesser of Two Evils

My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... read more

shemale lover March 27, 2013 84%

Chinese Apple Turnover

I crashed harder than anytime ever in my life and my dreams were fucking vivid. I dreamt of being fucked. And of sucking huge cock and getting face fucked so hard that I was cock drunk and high from holding my breath so much. But so really horny from him doing that, so into that cock. Of Jax f... read more

ASSEaster5678 January 9, 2019 100%

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%

A Night of Lust

I was out at a night club with a few friends, and we were there for for a while before I noticed this sexy, rather short girl across from me at the bar looking over. I could tell, even from this distance that there was something special about her, I wasn’t sure what that was quite yet though. The mo... read more

JessicaEdwards August 7, 2018 96%

Nancy the hot and sexy TS in Pattaya

Hi this is Ris, this is my third story. Well Last year I went to Thailand on lone trip. I went directly to pattaya and had rest and went to Walking Street in the evening. Was visiting many nude bars, ts Bars, dance bars. but while walking on the street one particular girl catch my attention. s... read more

Stud4Shemale May 22, 2017 73%

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%

Wrong Vampire

I consider myself a fairly tolerant person. I judge each person on their merits, not their skin color, gender or even sexual orientation. I'm even in favor of the Vampire Rights Amendment, but I must admit, unlike other groups people discriminate against, they make me uneasy. They claim that all the... read more

ASSEaster5678 April 23, 2019 80%

Slut indiscretion

At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... read more

Regina10 September 16, 2020 77%