A Night Out with My Sugar Daddy
At a relatively young age I met a older top, he lives in the apartment across from mine. He decided to become my sugar daddy and he has paid for me to transition and all my new outfits. In return I
An Unexpected Encounter with the Pizza Delivery Guy
I transition when I was young, I was raised by my step dad and eventually his second wife and they helped me to transition. My step dad enjoyed turning me into his girl, anyway that is a different
A Journey of Self-Discovery Through Fashion
I had been a closeted CD for most of my life. It started sometime when I was in junior high. My next door neighbors were a dad, mom, and 2 daughters, one was my age and we were like best friends the
A Surprising Day Off with Unexpected Guests
I have secretly been bi for years now. I'm 29 and married, but at some point while I was dating my now wife I got curious. At one point I decided to secretly try on one of her thongs and I loved
An Unexpected Roommate Encounter in a New Town
After I was completely done with school and was moving out on my own for the first time I decided to move out of state. Growing up and had gone to a few different places and one of them I fell in
A Memorable Halloween Cosplay Party Adventure
With Halloween around the corner I figured I would share what happened to me last Halloween. I am 22 and a TS. My bf asked was hosting a Halloween party that year and he is into cosplay and makes
A Weekend of Unexpected Encounters
I'm 27 bi and married. Normal day to day I come across as a normal masculine guy, but anytime I'm home and my wife is at work or out of town I become a sissy boy who loves to wear my
An Unexpected Movie Night Reunion with Friends
Part 5 of 5. We had all kinds of fun that weekend then my best friend went back to school, but before he did his dad told us he didn't care if we fucked each other even when he isn't there.
An Unexpected Birthday Surprise at Home
Part 4 of 5. So I ended up moving in with my best friends dad. As we would fuck he began dressing me up more and more he bought me wigs and make up and had me start hormone therapy. I began to dress
An Unexpected Invitation After School
Part 3 of 5. Right as my friend and I finished getting him packed up and all his stuff in his car his dad got back home. We both said goodbye and my best friend left to go back to school. His dad
An Unexpected Visit to a Best Friend's House
Part 2 of 5. So the next morning after my 21st and after getting fucked for the first time from my best friend's dad, I got up and went home to my apartment and showered then rested the rest of
An Unexpected Visit from a Friend
I'm married and bi, and I love to wear my wife's clothes for men when she isn't home. I'm 26 and white and have a thing for black men. I'm not passable and don't wear
An Unexpected Encounter with a Delivery Driver
I'm 26 and a tgirl with nice curves. One day I order Uber eats and when I saw it was a guy I decided I wanted to try something fun. I got dressed in my sexiest most revealing and tightest fitting
An Unexpected Guest Changes Everything
One night my wife decided she want to see me wearing one of her thongs, she liked it so she dressed me up more a took some pics. That night when she blew me she also put a finger in my ass and she
A Week of Exploring New Identities at Home
I'm 26 married and bi, but when my wife isn't home I love getting all dressed up in her clothes. A few months ago my wife left town for 2 weeks to visit family. I responded to an ad of a guy looking
Unexpected Role Play in a Couple's Dynamic
I'm bi, and I was playing with this couple for a bit sometimes all 3 of us sometimes just the wife and i, but almost never was it just the husband and I. Well one day the wife decided to dress me up
An Unexpected Guest and a Roleplay Encounter
I am actually bi, I'm 26 and married and I enjoy wearing my wife's thongs, bras (stuffed), and dresses when she isn't home. I had a guy come over with a nice BBC, he roleplayed that he was breaking
Unexpected Night at the Roommates' Party
I posted another story of a guy having me over then all his roommates joined and after they invited me to a party the next weekend. Well, I get there and there are only guys at the party, I didn't
An Unexpected Encounter with Roommates
I responded to an ad from a guy looking for an Asian ladyboy. I go over to his house, and he said we have to be quick before his roommates get home. I get on my knees and start sucking him. He heard
A Married Man's Secret Encounters
I'm a married bi guy, 26, I love wearing my wife's panties, bra, and dresses when she isn't home. I met my FWB on here, he comes over and I answer the door dressed up. He always grabs me and makes
