Free Shemale Stories

2nd date with Latina Sissy Destiny

So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... read more

AllenB April 5, 2022 100%

Alex’s Bottom Slut

So when I was younger, I worked at a pizza place as a delivery guy. It was a pretty boring job for the most part but that all changed one night. I got a delivery to just outside of our range but decided to take it anyways because we were slow. When I got there a very tall and muscular black woman in... read more

Jsmithsub November 18, 2019 86%

First time shemale encounter

Lets start off by saying this a very true story, one that i love to re-live over and over. lets begin I was in el paso, texas..my girlfriend at the hotel. Something in me decided to go to the strip club. So i did. After a few dances, i decided to leave. I had always heard in mexico it was very ea... read more

iloveshemales112 December 17, 2011 80%

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%

tgirl Hana in Sydney

I love spending time with tgirls and one of my favourites is Hana in Sydney. Setting up a meeting was easy, I texted her when I was close to her place. In her apartment, we kissed and hugged at the door and then she led me into her room, we settled the finances and Hana offered me a nice clean to... read more

xanykeyx December 19, 2019 85%

My sexy Shemale Cousin

This is 100% True and whyim cumming in my pants while writing it This weekend on my birthday My sexy ass cousin came over I Loved my cousin From the first day i saw her And that was also the first time i beat my dick to her And i Knew she loved me cause i always saw her hold her crotch every tim... read more

TheKingOfLadyboys January 27, 2014 56%

A day to remember

so I'm on a business trip and decide to call an escort to make this trip worthwhile. set up a time for an afternoon date call when I get to the parking lot. she answers the door in a nice skirt and top on invites me in and we procede to her bedroom. from there stood the sexiest black tgirl Ive ... read more

BlkCockJockey April 17, 2018 70%

First Time I tasted Tgirl Sperm

I met a Mexican Trans girl online from Hermosillo and we hit it off and corresponded for a a few months. The vibe was good and ended up deciding that I would help her pay the $140 bucks for her 6-month tourist visa to come up and visit..the process took forever but once she got it, I booked her a pl... read more

AllenB August 9, 2022 92%

Shawshan part2

The summer weather has finally let up and cool evenings where you need a sweater are among my favorite times of the year. Charlene left now from prison and served her time for drug possession. We had become close friends as well as cellmates over the last few months. She no longer cuts her hair as ... read more

Jon Paul May 20, 2021 100%

Oneness with the bodies

many years went into just fantasizing being with shemales. I was getting hornier day by day to try it out. But being in a relationship there was hardly any room or time for it. I once experienced it in bangkok and confirmed that I really can do it and actually love it. One day suddenly it was br... read more

zyankhaan786 May 30, 2023 100%

TS Fiorella in Frankfurt

Recently I was visiting Germany for a conference. I was staying in the city close to the train station and checked out the red light district nearby. Walking through the red light district is an experience, on every corner and many places in between there are multi storey brothels where you can wan... read more

xanykeyx October 24, 2019 69%

Frühes Erlebnis im Kino 2

Mein Gott, kam mir die Woche bis zum nächsten Freitag lang vor. Immer wieder musste ich an die geile Zeit mit dem Mann im kleinen Kino denken: Zum Transporno wichsen, blasen, den gemeinsamen Orgasmus erleben. Jedesmal tropfte Vorsaft aus meinem härter werdenden Schwanz bei diesen Gedanken an den let... read more

owltranslover April 20, 2022 100%

Recording Myself GangBanged

Get ready to grab your ankles as Agatha Tavares, Beatriz Silva, Bianca Reis, Luana Pacheco & Yasmin Dornelles use me as their pool bottom boy! It's Tgirl overload seeing these hung babes in their bikinis. Soon their tanlined tits and throbbing cocks are out as they rub their hands all over my body. ... read more

KevLoc417 October 25, 2021 25%

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%

ATTENTES SUBVERTIES ⚧️ ⚧️

Les choses allaient si bien.... Après un long et misérable quart de travail, Steven rentrait enfin chez lui. La plupart des gens détestent faire la navette, mais Steven trouve que la demi-heure de route est un moyen idéal pour se détendre avec un livre audio ou un podcast. Dernièrement, cette pet... read more

Femboy 2021 February 17, 2023 100%

My Afternoon With Venus - Part II

My mind was still spinning from the out of this world cock sucking I'd just experienced at the expert lips of my exotic little doll as she led me by the hand into her bedroom. Her pink summer dress was draped down onto her waist so now it was only just covering her cute little derriere. As I wa... read more

funpics March 23, 2018 100%

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%

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%

Best session with a T Girl

I like T-Girls. Recently had a chance to go to Costa Rica for work. While I was there I decided to see what Costa Rica had to offer in this department. There is quite a good amount of girls to select from. I started texting this Tgirl and we set a time. I got ready and headed over. It was a Hotel th... read more

horny.hiker April 30, 2019 95%

My first date with a "shemale"

I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... read more

bmogotti March 9, 2020 41%