Free Shemale Stories

Trying It On For Size Part 2

I looked up and saw the low slung scrotum swaying above my eyes, the long, thick, curved shaft pointing upward just in front of it. I heard a quiet tearing sound,"schshhhtt," looked further up and saw Tanya opening another one of her black foil Magnum condom wrappers. She placed the large,... read more

shemale lover October 26, 2011 100%

A New Spin On Role Playing Games

A New Spin on Role Playing Games By: Shawna Summers shawnavinylltv@gmail.com I've always been something of a geek. I love sci-fi and fantasy books and movies; I can recite countless bits of useless trivia back to you about all kinds of movies. So, it was no real surprise that I took to rol... read more

shawnavinyltv June 14, 2018 88%

Headmistress' Favorite Sport Part 8

For Denise her life as a fully trained slave began with a stay at Mistress Rachel's house before joining the twins' household. Since it was their idea to turn her into the sissy she now was, it was agreed that she would be their slave. But as the twins were moving out of Mistress Rachel's house and ... read more

shemale lover December 13, 2011 50%

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%

Story for adults Part 5

Alice's life continued like that for a couple of years until one day Mistress Angela got fed up with Janice. Janice had never really been into the S&M-bit and in time this began to annoy Mistress Angela. At the same time Mistress Angela began to regard Mistress Jensen as just another freeloader.... read more

shemale lover December 20, 2011 100%

Intro to a Dream Made Real

Jim had known growing up that he enjoyed bi-sexuality. But he had never found a man attractive the way women were to him. For example, he never found himself wanting to kiss a man, but he liked holding a hard cock as much as he enjoyed touching a wet pussy. He really enjoyed sucking a dick as much a... read more

shemale lover January 22, 2013 75%

Helplessly Bound

Hikaru slowly awoke from her deep slumber. She felt her head was so heavy, like having something had weakened her physically. Her vision was blurred and bit by bit slowly getting better, as she tried to investigate her surroundings. It was a dark room, only such a faint light so nothing could be ... read more

shemale lover December 3, 2011 0%

Headmistress' Favorite Sport Part 2

Over the next week the twins trained him further. He was taught how to apply make-up and how to behave in a properly feminine and submissive manner and they trained his movements to be properly feminine. So as not to wear the skin of his ass, the twins introduced a new punishment tool for these trai... read more

shemale lover December 12, 2011 71%

Headmistress' Favorite Sport Part 3

There was no more time for Denise and Susanna to get over their chemically induced bout of incestuous activity as Denise was being sent to school. This was of course part of the plan. Slaves should always feel guilty about something and once their slave training was over, neither would be able to ma... read more

shemale lover December 12, 2011 87%

Debbie Part 7

As Debbie was led into Dr. Jacobsen's office, she saw that Mistress was already there waiting for her. "Your property Miss Chamberlain", the doctor proclaimed, indicating Debbie. Debbie's heart began to flutter with love and submissive fantasies as she saw Mistress. Mistress was dressed in... read more

shemale lover December 23, 2011 80%

Blue collar Master, white collar slave

I sit on the couch in my owner's house, dressed every bit the slave I am. My body from the tips of my toes to my eyelashes is completely and permanently hairless, smooth, soft and beautifully tanned. My upper body is clad in a thin, soft and pink rubber T-shirt and my ass is clad in a pa... read more

shemale lover January 12, 2012 50%

A Great Cocky Owner

Immobilized, that's what I was. Although I did not know for exactly how long. My wrists and ankles were tightly shackled, and I was unable to see or speak because of the tight latex hood that had been put over my head. Nevertheless, I still managed to make out through the heavy gauge rubber the &... read more

shemale lover April 26, 2013 83%

Jessica's Rules

You knew that you had made an error in not following Jessica's instructions. You felt that you would be able to do as you pleased while at home alone. That, of course, included the right to masturbate at any time. After all, you had been beating off several times a day since your early teens. T... read more

Jessicajaxfl2 May 18, 2016 83%

Big Dick Alessia Visits Dallas

Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... read more

darrell April 20, 2022 100%

Fourth Slave

I had been to this particular establishment before. I knew very well what they did and the women here were nearly all abducted. I knew that. What had brought me here today or rather on this night, was the loss of my slave. I had sold her when I got bored with her. I had a particular taste in women t... read more

shemale lover November 19, 2012 66%

Aunt Cindy's Bizarre World Part 2

Chapter 7 I am guessing it was just over an hour until I heard the door open. It was her again, Miss Sindy Satin my auntie. This time she was wearing just an under bust white satin corset, long boots in satin exactly like mine but in white and her long, white bridal satin gloves and a the ribbon ... read more

shemale lover December 2, 2011 80%

Trying It On For Size

I was twenty minutes early for my one o'clock appointment so I found a shady spot in the parking lot of the upscale chain motel, kept the engine running to power the air-conditioner on the warm Sunday afternoon, took a few deep breaths and tried to relax. My mind wondered back over the series of eve... read more

shemale lover October 26, 2011 50%

LE PARI (MAMAN/FILLE FUTA)

Ma mère, Kendra, se promenait souvent dans la maison sans haut, laissant ses énormes seins couler librement. Ça m'a dégoûté. J'étais sa fille, pas un gars au hasard qu'elle a ramené à la maison un vendredi soir (pas qu'elle a ramené des gars à la maison). Elle ne devrait pas montrer ... read more

Femboy 2021 February 11, 2023 100%

Becoming a Shemale's Bitch

I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... read more

metamafia December 21, 2012 84%

LE PROGRAMME D'ÉCHANGE SISSY ⚧️ ⚧️

Kristy a travaillé pour Le Matriarcat. Cela semblait plus officiel que ça ne l'était vraiment. Comme si c'était un "Nouvel Ordre Mondial". C'était en fait un club dirigé par des femmes spécialisées dans certains services que les hommes paient grassement. Cela pourrait être appelé prostitution selon ... read more

Femboy 2021 March 25, 2023 50%