Free Shemale Stories

Real TS Encounters

Real TS Encounters Lay Report #1 Thursday June 9th, 2016 Hey, so this is my first “Lay Report”, which is what I will call them for now. My intent with these is to share stories of my encounters, while at the same time being informative enough to the point where you can get some value from ... read more

caspergrey June 15, 2016 57%

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%

The Greatest Lie Part 15

I think that if you could get honest answers, a lot of heterosexual guys would probably admit to having had at least a passing desire to be a girl. If they were honest, they would probably admit they thought of it "when I first noticed a girl's breasts" or "when I first felt a girl or... read more

shemale lover January 20, 2012 50%

The Greatest Lie Part 17

They say that life is about making choices. But we humans don't get to choose the two most important factors in our lives. We don't get to choose our genes, so I got stuck with XY chromosomes. And we don't get to choose our natal families, so I got stuck with my mother and father. My father, Edua... read more

shemale lover January 20, 2012 50%

The Greatest Lie Part 13

Does Life Imitate Art? I love technology, in spite of the stereotype about girls. Although I was a guy, at least outwardly, until a year ago, I think I was always inwardly a girl. According to the stereotype, we girls are supposed to be indifferent to anything more technical than the designer cov... read more

shemale lover January 20, 2012 0%

How I Learned To Love Drag Part 1

"How about doing a sports interview?" I suggested. "We could have hockey's dirtiest player doing a tell-all about how to inflict pain without taking a penalty." "Yeah," agreed Ted. "The bad guy could demonstrate all his dirty moves on the interviewer. Like an el... read more

shemale lover December 29, 2011 25%

I am Baaack! Part 11

Now Rose upped her sincerity level. "I want that kind of friendship with you, Joan! I believe we are kindred spirits. If two manipulative bitches like us CAN be friends, I think we should be. I did this little scenario today as a show of skill, inclination, and sincerity. Could I do to other me... read more

shemale lover December 17, 2011 50%

The Greatest Lie Part 7

The horrible memory of my crackhouse ordeal faded much as the lurid surgical site on my abdomen faded to a faint pink smile at my bikini line. I went off the AIDS cocktail after one awful month of constant nausea, and was pronounced antibody-free. My surgeons pronounced me healed and recovered. Natu... read more

shemale lover January 19, 2012 0%

All Woman and More

It was one of those soft southern nights you hear about in movies and old soft rock songs. I could smell the long leaf pines and the moon was nearly full. I had been on my own for so long that it rarely bothered me as it did in my youth. That lonely feeling that never quite goes away. Now it came on... read more

Windmillchaser September 20, 2018 100%

My two encounters with shemales

I love it when our readers submit their stories. This one was posted by Harry a couple hours ago and i think it deserves its own post. Let us call the story "My two encounters with shemales". Enjoy reading! Last winter while on vacation I also had sex with the most beautiful shemale, wo... read more

shemale lover June 25, 2015 80%

Lay.. BJ Report #3

Lay Report #3 Real TS Encounters Lay Report (BJ Report) #3 Hey, So this is my 3rd official “Encounter Report” lets just say. This was early Saturday morning June 25th, 2016. Unfortunately, this report will not be that interesting/informative. I am writing it just because it did happe... read more

cngwriter August 2, 2016 80%

A T-Girl Romantic Interlude

Dear Reader this is a romantic interlude, not a story. It is a brief glimpse into a sensual moment in a relationship between two people that are in love. Please use this to stir your imagination, no matter the side of the situation with which you may identify. Somewhere in Greece... The whitew... read more

shemale lover October 31, 2011 100%

The Greatest Lie Part 8

I love academia just as I love getting fucked; each validates me in a different way. I was born of academic parents, and was holding forth at their cocktail parties before I could pronounce all my consonants. To me research papers and exams are just opportunities to display my superior intellect and... read more

shemale lover January 19, 2012 0%

Lay Report #6

Lay Report #6 Sunday Night into Monday Morning, August 29th, 2016 Location: Long Island to New York City Title: “Post-Op TS Hookup. Not my first, but probably going to be my last.” What’s up! It’s Casper again, and I have yet another “Lay Report” for you to check out. So let’s just get r... read more

cngwriter October 10, 2016 65%

Crossdresser gets surprised part 2 ( true story)

I laid down on the bed pulling him down over top of me. We started kissing passionately and making out. He kissed my neck and softly sucking it which was driving me crazy. He whispered that he better stop sucking on my neck before he left hickeys. I said you can baby do it. He sucked each side of m... read more

cdpaula September 21, 2023 100%

Tourmenter ⚧️ ⚧️

Sasha attendait avec impatience ces vacances en famille depuis peu de temps. L'invitation était courte mais faisable et même si elle se sentait un peu pressée à son goût, tout se passait bien. Elle adorait sa caravane. 'Glamping'... camping glamour... convenait à son idée du confort e... read more

Femboy 2021 March 23, 2023 50%

The Greatest Lie Part 12

My Own Worst Enemy Let’s face facts. The so-called the "War On Drugs," "Just Say No," and all the other anti-drug campaigns are complete failures because they ignore reality: getting high is fun. College students drink and take drugs to break a boring routine; the poo... read more

shemale lover January 20, 2012 100%

Double Wedding

I was about to marry my childhood sweetheart Paula Rother. I loved her and she loved me but it hadn't been straightforward. After school she went to Manchester University while I went to work at a local accountants as a lowly paid junior clerk. She said we where inseparable but during the two years ... read more

shemale lover November 8, 2012 100%

LES SEINS VOUS RENDENT STUPIDE ⚧️ ⚧️

"C'est jolie!" "Oooh... Sexy !" "Salope !" Ce ne sont là que quelques-uns des descripteurs que j'ai utilisés lorsque j'ai "fait du lèche-vitrines" en ligne. C'est l'un de mes passe-temps préférés. Aller sur divers sites de lingerie et regarder des soutiens-gorge, des culottes, des bas, des jarret... read more

Femboy 2021 March 31, 2023 50%

Good hardcore fuck with a shemale from Vancouver

Our reader Tommy writes about one of his adventures with a shemale. Sure, it turned out to be not as romantic, but, as he says, nevertheless it was a good hardcore fuck! Thanks to him for this great story. One night on biz in Vancouver I saw some adverts in the paper for shemales and got hot and ... read more

shemale lover March 25, 2015 85%