Free Shemale Stories

Cindy She Thong

Dialogue from Cindy’s point of View: Her name is Cindy and she is a shemale. Cindy is a beautiful woman is every way except one. She does not like the term tranny and prefers being referred to as a shemale. She is truly happy living as a woman. She began taking light doses of hormones at 19 she had... read more

mrstanley July 29, 2015 83%

Hung Alessia Travestita meets MILF

Hung Alessia meets MILF with Giant Clit Several days ago, Alessia a beautiful English Transvestite met a tall slim sexy Canadian woman named Sandra on the internet. They were captivated with each other's nude bodies and genitals. They immediately engaged in a video sex session together. Sandra fu... read more

darrell August 13, 2023 100%

MILF Alessia Travestita finds a bottom boy

I was several days into a cruise to New Zealand and Australia with my wife. This morning my wife went on an excursion that I had no interest in, so I had the cabin to myself. I hadn't had any sex with my wife in the last 3 days due to the activities such as the various jaunts to Auckland and the sur... read more

darrell August 13, 2023 93%

Francine Hung Shemale

This is the story of "Francine" a Transgender woman from California. She and Jonathan meet in a Tucson resort two weeks after their first weekend together. Note from Francine-Thank you Mrstanley for writing and submitting my story. In real life I live and work in California and Mexico as ... read more

darrell November 16, 2015 85%

Francine Hung Red Head Part 2

This is the second part of the story of "Francine" a Transgender woman from California. She and Jonathan meet in a Tucson resort two weeks after their first weekend together. Note from Francine-Thank you Mrstanley for writing and submitting my story. In real life I live and work in Cali... read more

darrell November 28, 2016 90%

Cindy and Juanita Kinky Shemales

Her name was Cindy and she had been born a male. Cindy was a beautiful woman is every way except one. She didn't like the term tranny and preferred being referred to as a shemale. She was truly happy living as a woman. She began taking light doses of hormones at 19 she had stopped hormones beca... read more

darrell November 30, 2016 86%

MILF Alessia Travestita finds a bottom boy pt 2

Several days ago, Alessia a beautiful Transsexual with a huge cock seduced Stan on their cruise ship. He willingly and enthusiastically sucked her cock and gave her his ass. She brutally throat fucked his mouth before pounding his ass. They spent over two hours together until they were interrupted b... read more

darrell August 13, 2023 100%

Hi, My Name Is Hollie Chapter 1

Hi, my name is Hollie! Hollie Marie Gibson. But my big sis, Emillie, usually just calls me Holl. She and I were born within a couple of years of each other, and we get along really well. I just wish our body types were a bit closer, so we could share clothes like some sisters do. That would be so co... read more

shemale lover December 19, 2012 90%

The Masseuse

I book a massage at an upscale private place in downtown Toronto. I arrive and the masseuse looks gorgeous, dressed casually, in a tank top and short cut off jean shorts. Her breasts barely being restrained under the bra-less top. Her stomach exposed, flat, toned, with hips exposed just above her ti... read more

Basil5503 September 18, 2016 94%

My Fantasy Came True

Hello all I'm a trap or a CD or a Sissy anything you can call me.I can be your trap or Sissy. Here is my first BBC Gangbang. When I got my fantasy fuck.I'm a Sissy Bitch of my friend.He make my fantasy came true.So here's the story. Last week I got my First BBC Gangbang.It's... read more

TrapBomb September 26, 2016 60%

Throat-fucking: A special type of handsfree breathe control

The following directions is a specific way this blogger likes to penetrate the esophagus. The subject is either laying on their individual flat on their back with head flat on the bed as well or haOk ve their head hanging over the edge, while your penis approaches the subject from above. While the T... read more

Hothungmeat. March 2, 2021 50%

My first cock

I've been swaying towards shemales for a few years now. Usually when I'm high. I'd get loaded and all of a sudden I'd have an urge to to be with a transgender. The thing is, initially, when I sobered up, I regretted any such thought, even hated myself to think such thought. Over ... read more

fahrenheit77 October 6, 2014 53%

Deflowering Tgirl - Nathalie Daniels

--{ All my sex-stories are told from my own-experiences }-- “My imagination was becoming equal to reality” After the tour , which by the way was really great , I sat down facing the bed that stood where a maid was busy spoiling . Someone down on a bench There were several people watching and... read more

Nathalie Daniels January 4, 2015 54%

Pay the Genie

Scott trudged along the beach while waving his metal detector from side to side. His afternoon walks had yielded little in treasures over the past months, but helped to center him when he felt lost or depressed. His fiance', Denise, had left him for his boss at the firm when Scott had been passed ov... read more

shemale lover October 12, 2011 100%

My First Time Out Part 4

It was Sunday morning at eight o’clock when the phone rang. Shayna’s eyes felt like they were glued shut but managed to answer the phone on the third ring. “Morning,” said Shayna as she was still half-asleep. “Good morning Shayna. This is the Bell Captain calling.... read more

shemale lover October 18, 2011 50%

Transsexual Sisters Chapter 6

Part 6: A Party to Remember MICHELLE AND NICOLE MAKE A CAREER CHOICE After their tormentors were jailed, Michelle and Nicole felt relieved and happy for the first time in weeks. Whether from curiosity, respect or sympathy for their ordeal they became very popular around the USC campus. They we... read more

shemale lover September 8, 2012 100%

Love to Fantasize

I love to fantasize; it is one of the greatest things on the face of the earth. I have many fantasies, tho I have given up on a couple since I married my wife. I am a white male of 27 years, and since I was sixteen, I have had many erotic fantasies stemming from reading my parents adult story magazi... read more

shemale lover December 20, 2012 100%

Proud To Be A Sissy Chapter 6

It was still early and I wanted to enjoy the feeling of being dressed in my shear hose and garter belt, tiny g-string panties and matching bra and the form fitting shiny black mini dress that barely covered my stocking tops for as long as possible. So I spent some time doing some domestic chores and... read more

shemale lover December 24, 2012 92%

Heather and Lori

This a true story about me and two very hot TS friends. I was down in Ft. Lauderdale and had hooked up with Lori and Heather. Two friends from my NYC days. They had relocated to Florida and told me to stop and see them when I came through. I met up with them at their apartment and we opened a bottle... read more

shemale lover November 9, 2014 95%

Deep Throating Shemale

Yvonne is one of my best friends and we do more than just hang out at the local nightclub. She has long wavy black hair and dark violet eyes. Like me, she is also a pre-op transsexual, which means she has breasts and a penis. In the few years that we have known each other, she has taught me a lot ab... read more

shemale lover May 29, 2015 94%