Free Shemale Stories

A date to the sex shop

So last night I decided to meet up with a young shemale in Portland, now this is my first time ever with a trans and I was so nervous and excited all at the same time my face kept doing this weird little twitch. So we hang out for a little before we decide to go to one of those classic dirty sex sho... read more

Quin Sharp May 31, 2017 38%

Shemale fun

Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... read more

shemale lover November 25, 2014 96%

Shemale fun

Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... read more

shemale lover December 3, 2014 80%

Southern Hospitality Ch. 04

XtinaSmith2017 Ash awoke feeling cold, he pursed his lips a little and shivered, curling up a little tighter, nude as he was, the action brought little relief from the cool air. He let out a soft murr of discomfort as his mind shook off the cobwebs of lingering dreams, he could see light throug... read more

Gwapo67 May 16, 2022 92%

Tight Spot

XtinaSmith2017 Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavor but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way ... read more

Gwapo67 July 22, 2022 100%

The Next Level

Nitromethane It's been a couple of weeks now since I sucked my last shemale cock and swallowed her load, and with enough distractions, it hasn't been too difficult keeping myself preoccupied and my mind off of satiating my new fixation. Still though, I do have my moments when I sit back and imagi... read more

Gwapo67 February 1, 2022 100%

Intense

Holding to my word, I didn't let the incident with Billy and his friends scare me away from Bailey; I kept seeing her, even after the beating I took. To be honest, I'm not sure if he was trying to lay low or what, but Billy seemed to keep his distance from me for a while...thankfully. Bailey and ... read more

Verpa October 21, 2019 100%

Group Sex

Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... read more

Jon Paul April 19, 2021 80%

Southern Hospitality Ch. 02

XtinaSmith2017 Laura felt herself lifted lazily from the arms of sleep, her body relaxed and floating on a small cloud of pleasure, her mind filled with images, sensations, not pulled from whatever dream she had just been having but instead, memories, memories from the night before. Memories of... read more

Gwapo67 May 16, 2022 91%

Alex and Jon

Alex was not beautiful, but had a sexy attractiveness that most could not help but take a second look. This was the case with Jon as he searched adult Friend-Finder ads for someone that would satisfy his desires and dreams of a companion. Alex, a transgendered Filipina girl, had the bronze skin colo... read more

Jon Paul September 21, 2022 88%

Shawshank affair

Courtrooms can be a scary place. They smell like older leather, the wood paneling has been polished with oil and each sound penetrates your body like a loud smack from a cap pistol, which echoes in the forest, especially the gavel smacking on a block from the Judge. I felt strongly that I would be f... read more

Jon Paul August 20, 2018 100%

I am seeking an open-minded trust worthy lifetime partner...

To all of you who are fakers, jerks, wankers, trolls and pretenders, please moveover cos im not interested in your lies and silly games. Life is too short to those who fool around or so, etc. etc... I am Top and dominant. seeking for my lifetime partner. I know im not perfectly beautiful, not a g... read more

Vurikat March 29, 2022 100%

Southern Hospitality Ch. 01

XtinaSmith2017 Ash gawped at his mother, incredulous as to what she had just said. He understood the basic premise of what had happened, but the reasoning she must have had absolutely baffled him. "Why?! Why would you do that?!" He pleaded, voice light and desperate. She shrugged, looking acr... read more

Gwapo67 May 16, 2022 93%

Southern Hospitality Ch. 03

XtinaSmith2017 Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned ... read more

Gwapo67 May 16, 2022 87%

TG girlfriend is my new neighbor

With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... read more

Jon Paul January 17, 2022 100%

TG Neighbor

With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... read more

Jon Paul April 22, 2022 100%

Liberty in Lisbon Part 2

So here I was walking down the Av da Liberdade feeling very pleased with myself. I had just thoroughly enjoyed an experience I thought would only ever be in my dreams and, the best part, there was more to come [cum]. In fact I found myself humming the 59th Street Bridge Song. Life I love you feeling... read more

Rusty12 July 31, 2019 100%

Transsexual Savage

John had walked for eleven days. He was headed towards Fort Winston at the Hiat River, and he still had about three days ahead of him. The Hiat River was the natural border that separated the civilized world, where he came from, and the savage and brutal wilderness, where the natives lived and pract... read more

Anal Orgasm July 10, 2020 80%

My weekend with Nicole

So I believe I last left off about how me and Nicole started dating and let me say it was some of the best sex I've ever had but there is one particular time I could share. So after about 2 months of dating I was basically staying almost exclusively at her place. So the first weekend I s... read more

Duke04 May 20, 2017 84%

Bimini (part2)

Emily was introduced to me by my friend Jan at a night club. ‘Em’ is a 19 y/o t-girl and absolutely adorable figure and very sexy legs. Well after leaving me at the club with Emily, I had invited her to fly to Bimini the next day for a long weekend . If you read part 1 you will know. Waking up... read more

Jon Paul April 19, 2021 100%