Free Shemale Stories

What if it is always your turn?

So I'm on AFF and get a ping from a guy whose been wanting to give me a blowjob and see where it goes from there kind of line. I respond back, sure, want to get a drink, I would love some Sake. We met down at the local sake shop, I am uncouth, I only like warm regular sake. I get a large to share an... read more

smtmsbrianne2 October 17, 2023 100%

My Ts Escorts Favorite Memories 1

I tend to turn to my dirty secret once a week. I had been searching for months for the sexiest escort to call when I finally got the nerve to call the ads on backpage. My most recent one was for a Cuban Goddess with a 9 inch FF verse, tall slim big titty small waist tight booty.. When I got to ... read more

Ur Papi Chulo January 20, 2016 72%

Caught!

Let me start out by saying that I was very much in the closet about my dressing and the fun I have when I'm dressed when this happened. But more and more I kept fantasizing about one of my male friends. He's very good looking and keeps in shape by jogging every day. Several of the times we've gone o... read more

shemale lover June 7, 2011 100%

And Life Goes On

I am sitting in the living room waiting for my date to show up. A date arranged by my wife Gwen. I am dressed in a slinky red dress, underneath my torso is encased in a white corset which reduces my waist to a mere 25 inches. On my legs are a pair of black nylons attached to the straps hanging down ... read more

shemale lover January 10, 2012 100%

Dressing and driving

A little about me, I'm married, and wife doesn't have a clue I like to dress up. I would love to have her know and accept it, but I don't think she would. I do cam and love to get instructions from people that are watching on cam. Am I a sub? I think I am. I like to drive dressed. When I take a driv... read more

SandyCrossdresser November 26, 2018 100%

Shock and Awe. Part 2

Carla lay back on the white sheets and said ‘I want you to lick me down there first’ I was a bit shocked to be honest. I mean every guy imagines what it must be like to suck a cock at some point in their lives (and I just had for the first time, it was lovely), but anus licking had ne... read more

shemale lover May 17, 2014 100%

Fucking Insatiable

* Draenei futanari, as many of us have become intimately aware, are fucking insatiable. For many of the same reasons, they also have a tendency towards entitlement and ego issues. This is hardly surprising, being a magically-fueled blue-skinned space-babe with positively porn-star T&A and a d... read more

shemale lover December 7, 2012 66%

Mommy Adriana, I Will Obey You

Finally we were on our way home. Interestingly neither Mommy Adriana nor Mistress Andrea had cuffed or gagged me. So I just sat in the back of our car. During the short drive I had some time to think about what had happened in the past two days since my wife, err Mistress Andrea, and I had picked up... read more

shemale lover December 18, 2011 50%

Attitude Adjustment

Angel sat on a chair in a crowd of women. She had come to this club to take in a couple of shows and she was really enjoying this one! This show was a group of hot looking guys that stripped for a living, which is nothing unusual in Miami, but these guys showed the "Full Monty", or in othe... read more

shemale lover October 24, 2011 83%

transvestite mistress gina

i went to visit tv mistress gina one day. as i walked in she ordered me to strip naked and lick her shoes, i did this for a while then she led me to her room. she placed me in a dentists chair spread my legs wide open strapped them down and did the same with my hands. my cock ass and balls were tota... read more

shemale lover March 13, 2014 84%