Free Shemale Stories

More from my closet....

......being single is so better to play my games, no wives to take up my day, no one to lie to anymore about where I went... I had a layover for 3days in Vancouver last fall, three days all to myself, with the aid of google maps I found the local steambath for men. Steamworks it was called, set... read more

badbadboi667 December 3, 2020 66%

Banana Fetish

I was 27 and single and enjoying being free sort of the ‘sworn to fun loyal to non’ stage in young adulthood. I lived alone in a 1-bedroom apartment and loved working on my motorcycle which I kept in my living room. Most Friday nights for me were jamming out to music, enjoying a few beers and tinker... read more

AllenB February 16, 2023 91%

Slut /W Bad Boy

I was excited as always because I was about to go out in public and hopefully I will meet some horny man with some money and get laid. Now, to make sure that I am a picture of femininity, I double checked my makeup in several mirrors from many angles. My lips were perfect and I made sure my cheeks b... read more

Regina10 December 4, 2020 100%

I fucked the hotel handy man and he had a monster cock

I was on vacation in a new town and decided to stay at this new hotel. I heard it was the best and the location was close to some sites I wanted to explore. I enjoyed my stay there, especially one evening when my air conditioner stopped working, and the hotel guy came to fix it. He looked so hot tha... read more

Madison Heights September 5, 2023 100%

Sissy Slut and Stepdads

Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... read more

Regina10 November 30, 2020 90%

From accidental trans porn addiction to a cum filled booty

One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... read more

CDJaneBooty April 1, 2022 100%

MY Party Favor Fantasy

My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... read more

pennypenny January 8, 2019 92%

The New Daughter In Law

After the evening before, I awoke with some doubts on that Wednesday morning. I went ahead and went to work, just because it was something I always did. I had just come out of a strategy meeting when someone told me that the managing partner wanted to see me. In the office he was Mr. Davis, or in a ... read more

Setinkhan June 2, 2021 100%

The New Daughter In Law

After the evening before, I awoke with some doubts on that Wednesday morning. I went ahead and went to work, just because it was something I always did. I had just come out of a strategy meeting when someone told me that the managing partner wanted to see me. In the office he was Mr. Davis, or in a ... read more

Setinkhan June 3, 2021 100%

Sissy Slut and Stepdads part 2

My mother kicked Frankie out and swore that he was the last loser she would ever date. She believed that we were still having sex, and she was right. Pure raw animal lust drove us, and It was even better when we sneaked and got. That nervous adrenaline mixed with my passion and made me super horny a... read more

Regina10 February 15, 2021 100%

Hot Slutty Sissy

Hello, It’s me, and. I am about to make a big decision and right now I am dedicated to my fantasy. I got a call today from one of my ex boyfriends. I got so horny when I heard his voice that my nipples turn to steel. My titties seem to respond to the sound of his vibrating baritone. I couldn’t refu... read more

Regina10 August 14, 2020 91%

Sissy Slut Reunion

Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... read more

Regina10 September 14, 2020 100%

La pistola NEGRA del Tío, entre Las Bragas de Mi Tía LA PUTONA

Aaayyy.. Yo sabía que la Tía había sido Flor de PUTONA.. pero, jamás me imaginé que me iba a tocar a mí 'hacerme cargo de sus cosas'.. su 'herencia'.. la casa ya vieja, por reordenar destinar y.. LAS COSAS que una descubre ya con los años! Todo estaba igual, pero HORRIBLEMENTE ARRUINADO.. más, e... read more

Ari Riè June 3, 2021 50%

Mi primera vez con una trans.

La semana pasada estaba viendo porno como siempre lo hago, siempre mezclo entre el porno tradicional y el porno de aShemale. ya que bajo cierto punto de vista, me consideraba bisexual y ver a las traviesas me volvía loco, siempre deseaba penetrar esas colas mientras las bolas le colgaban. Eventua... read more

ceresitanueva August 6, 2019 100%

Dating all whole my life

Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... read more

PornoDating August 15, 2019 40%

Shemale transformed in to a living sex doll and kept captive

I had connected with Master X on a BDSM Fetish contact site. He was the owner of a fetish store and he said that he had been on the BDSM for several years. He had carefully studied my own profile and had seen that I had an immense interest in being used like a slut, being covered head to toe in ... read more

__tiffanylondontv__ September 30, 2014 54%

Getting Fucked By Jeff

Getting Fucked By Jeff I was sitting at the bar one night having a drink and wanting some dick when a man sat next to me and said “Hi, I am Jeff.” Smiling at him, I said” Hi, I am Penny.” Jeff and I chatted and he bought me another drink. After a while, Jeff said” In all honesty, I only boug... read more

pennypenny February 25, 2019 100%

Transsexual Son / Daughter

Now I’m a 51 year old mother of one and watching my Daughter who’d been once my son putting on that very nice silk blue bra from Harrods department store and lift up her huge breast in to them made me so wet. Now seeing my son all now transformed and transitioned in to a beautiful woman ... read more

shemale lover October 16, 2012 78%

Giving Up My Freedom For A Fantasy

I arrived at his house early to get ready. I had specific instructions on what I was going to be wearing for the session and I had been locked up in chastity for nearly a month. He had left the door open for me, I entered and walked up the stairs and entered the bathroom. I was to take a shower and ... read more

Sissysophie780 July 8, 2019 50%

Loving Strangers

In the past I had never failed to disclose my sexuality to a new male prospect. I looked good in my tight dress that showcased my woman's ass, and the spike heels that made me look so fuckable. I knew from past experience that guys could get really pissed and violent when they found out you weren't... read more

Regina10 June 23, 2020 85%