Latest Crossdressing Sex Stories

Growing Up Male & Becoming a Girl

Dressing as a girl.

My sister is four years older than me, and since our father left the family when I was very young, I have really never known of a household that wasn't dominated by women. Growing up in the late 50's and early 60's, female lingerie was extremely feminine. Most every female wore a bra and full cut panties under a half or full slip every day. Garter belts and nylon stockings were also normal...

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My Master

The story of a sissy meeting her real master.

Editor's note: this story contains scenes of incest or incest content. * I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for a fortune 500 company. It's...

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Magic Dress - Yvette Pt. 04

Sex, love and marriage.

"Well," said Kathy when I got home. "You've nearly done it. You proved yourself as a woman in society, on a date and in the bedroom. And you've been dumped! Now what does Yvette want?" I said I wasn't sure, but I was hurt and I wanted the original dress. I got the original bra and panties and put on the dress, sat down and felt calmer. We had some tea and talked. She finally said that we...

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The April Fool's Day Trap

Tricked by my cross-dressing friend at the glory hole.

Author's Note: I am recovering from repeated surgeries on both arms to correct a degenerative nerve condition. To write this, I use voice to text software which isn't always accurate. As my recovery will take considerable time, I have decided to continue writing and give my best effort at doing the thing I love. Please, if you spot any typos or grammatical mistakes, consider volunteering as my...

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Life and Time of Lady Vargos Ch. 07

Martin meets with scheduled guest.

"The New Bitch of Vargos Manor" Written by: Rikki Lady Vargos begins to exert his new found powers as Lady of the House. He is able to channel many of his frustrations and anger through being tough and almost insulting to those try to accept him as the Baron's wife. As a result, word spreads and Martin is slowly becoming the Bitch of Vargos Manner. "Thank you so much," Missy said...

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Stray Cats Ch. 03

The Office Party and a trip to Seattle.

This continues the reprint of a story that I posted on this site in 2015. I was rereading it lately and correcting some of the typos ( many!) when it dawned on me that perhaps I should repost this story (corrected, of course, and in the original chapter format) for readers today. It's still relevant, well most of it is. I hope you enjoy it. _Oh, as a reminder, you might consider...

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Life and Time of Lady Vargos Ch. 06

Daily life and The Vow of Chastity?

Chapter 6 "Lady of the House" Martin had been home three days from his visit to the spa, and things were now becoming a bit more of daily routine for him as mistress of the household. As usual he had been awakened early by his husband with a long passionate kiss on the lips. Martin grabbed the sheets with both hands and groaned as he awoke in the affectionate displays of his...

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The Beast and the Butterfly

A tragic accident and a tale of rebirth.

It is the express intent of the author that all characters in this work are fictional and in no way represent actual people and that they should be interpreted to be over the age of 18. * Chapter 1 The graduation party had been fun. Our small school had made a deal with 'Pizza Planet, Fun and Games', our only local high school hangout, for an all-you can eat pizza...

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Magic Dress - Yvette Pt. 03


If I was truly to be a woman, it could not just be at home, so we started venturing out. The first time was just a walk down the street and back again. I wore trainers as many women do, the original dress (of course) for good luck, and a coat as it was quite cool. I was shaking, but managed. Slowly we increased the time and range of our adventures, but always together. I was of course terrified...

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Unorthodox Methods Pt. 03

FTM and his husband reconnect after the gangbang.

Author's Note: Please read Unorthodox Methods 1 and 2 in order to jump right into this one! This will be the final chapter. * Before I could settle into a moment's rest after receiving my fourth load of cum, a man (presumably the one who had fingered me earlier) began pushing on my legs. He stretched them above my head, but I was too exhausted to hold them there, so the arms of two...

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Mama's Girl

I became a sissy and suck an ebony woman's dick to survive.

Here's a story that just sort of popped into my head. I hope you like it! Of course, all characters involved in sex are 18 or older. This story is based on true events that take place some time in the near future. Please feel free to leave any comments, feedback or questions in the comment section and give it your honest rating. * Living in the projects of Chicago is exactly how it...

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Magic Dress - Yvette Pt. 02

Learning to be a woman.

Having tried on my girlfriend's dress, I had felt the desire to be a woman, and Kathy said she would help me as far as I wanted to go. We also agreed to marry, despite the unusual situation. So began my education and transformation. Which started not quite how I would have guessed. "OK, if I am going to share the flat with another woman, then I am going to share the woman's jobs. You can...

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Discovering Amber Ch. 07

The morning after a night at the club and more fun.

Mistress notes: The morning after is always fun, people tend to get caught up in the moment, sissies included, and amber was no exception. The fact Jenn and I were there to remind her of all of it just made it better! The fact amber seemed to really enjoy humiliation only added to the whole experience. Ms. Allison ~~~~~~~~~~~~~~~~~~~~~~~~~~ The following morning, I woke up...

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Neighbourhood Terror to Sissy Pt. 03

Mark gets a humiliating surprise at the salon.

(Hey, so things have been a bit busy lately, but I'm back with another part. I really hope you guys like what I have done with this and as always comments are really appreciated, enjoy.) * Mark woke up to the sound of his alarm with a loud groan. Taking the bus down town would take a lot of time and he had pretty much made up his mind that he couldn't afford to be late to the...

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Transgender in the Old West

The forgotten story of LGBTQ people in the old west.

Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows? Anyways as my regular readers are aware, I enjoy writing about characters with fluid sexuality. This is a story with transgender and crossdressing characters set in the old American west. ~~ John Calvin Kelly was JC's government name, but she...

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Miss Guided Pt. 02

The doctors agree on a treatment plan for our happy couple.

I arrived at Dr. Bill's office and he greeted me and we sat chit-chatting together for about ten minutes. Then, Charles and Emily arrived. Dr. Bill addressed us all. "I have read Dr. Price's diagnosis and report and I concur with her findings and recommendations. It's probably best that Dr. Price tell us about them herself. Dr. Em began saying, "Well, first Charles is not...

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Life and Time of Lady Vargos Ch. 05

Lady Vargos is spared nothing.

Chapter 5 "A Spa Education" Martin had been through a very traumatic week at the so called spa he had been taken away to. He cried himself to sleep most night wearing only ultra feminine nighties with loads of ruffles and lace in various colors of lavender and sapphire blues, black and even a rather childish looking very short nightie in hot pink. He had been forced to wear in front of a...

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A Long Cool Woman in a Black Skirt

A man meets a special woman.

I first saw her in the lobby of the hotel in which I was staying for my conference. I'm the national sales manager for a large manufacturing company. We hold a national sales meeting every year to which all of the regional managers are gathered for education on new products, sales techniques, etc. She was a tall woman, actually taller than I, but I noticed she was wearing heels, pretty black...

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Stray Cats Ch. 02


This is chapter 2 of a reprint, of a story that I posted in 2015 on this site. I was rereading it lately and correcting some of the typos when it dawned on me that perhaps I should repost this story (in the original chapter format) for readers today. It's still relevant, well most of it is. I hope you enjoy it. _Oh, as a reminder, you might consider going back to read the opening chapter...

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Futa Goddess Society

Miss Ashley hosts a sex party for fellow futa goddesses.

Cameron swayed back and forth on the sex swing, lying bound, gagged, blindfolded and naked with his stomach face down as Miss Ashley swung him forward and back along her large thick 12 inch cock. He moaned feebly as she stretched out his young asshole, as she had been doing for many years. Her beautiful brown skin covered her tight voluptuous body, a stark comparison to Cameron's skinny white...

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Jeri's Love... Ch. 01

Beautiful young trans woman finds love with her best friend.

Shawn came home for a short leave right after basic. He was awaiting deployment to the Mid-East and Jeri was determined to make love to him while he was home. Her eighteenth birthday had come and gone almost three months ago. She was so very sure that she was in love with her Shawn and she was determined to have his love in the physical realm as well as the spiritual. As she waited on his...

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Railed at the Train Station

Train molester has his way with a young FtM.

I'm FtM and this story is one of my darker fantasies. Be warned of intense non-con and the use of terms like 'pussy' and 'cunt' to describe genitalia (my preference). If you don't like the subject matter, kindly move along. * I had thought that all train molesters were ugly old men, but clearly this one beat the stereotype. He was a young businessmen - maybe 30, 35 years to my 21...

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Chuckwagon Cookie

Female cross-dresses to pose as a cowboy in the 1880s.

_Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows? Anyways as my regular readers are aware, I enjoy writing about characters with fluid sexuality. The old American west has an image of hardy settlers, tough as nails cowboys, and Native Americans fighting for their land. However there was another side to...

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Magic Dress - Yvette Pt. 01

I put on a dress and wanted to be a woman.

I put on the dress and my life changed. I cannot now remember exactly how it came about. Kathy had bought the dress second-hand, put it on, and asked me how she looked, so I said very nice. Then somehow she said I should put it on and I did. Perhaps it was a joke, I can't honestly say. It should have been ridiculous, a middle-aged man in a dress, but it wasn't. It was wonderful. I had been...

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First Time Hotel meet

After a cam session a first time meeting was arranged.

I arrived early so I had plenty of time to get ready. The hotel room was a bit scruffy, but as I asked for a 'smoking' room, probably as expected. I'm at this hotel because, earlier today, I was on a chat site and had a sexy chat, then a cam session with a cool looking guy. His name was Tim (so he said anyway) and he was new to the site, wanting to experience something different....

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The very hot cross dresser.

My first meet on the small cock dating site, a cross dresser by the name of Ginger, he is 30 years old and single looking for exactly what I got. He has light red hair and does his make up well. Brown eyes and he looks so sexy in female clothing. I gripped my hand while eyeballing his gallery. Wow he is so hot! My heart began pumping as I walked up to his porch and knocked on the door....

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A plane crashes and a survivors new life starts.

Flight Sixty Nine was going down, I had no idea what had happened, one minute we were cruising along at thirty thousand feet two hours into the four-hour flight from Seattle to Anchorage, and the next we were grasping for Oxygen masks as the plane dropped and lost altitude at an alarming rate. The Captain made an announcement, but no one could hear it over the roar of the engines and mass...

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White Gurl and Her Black Man

White guy becomes black man's gurl.

Well this is something I never expected. Here I am in a gay resort in the Canary Islands, can't remember what it's called, with a man, a black man. I am effectively his woman and my raison d'etre is to pleasure him. Well, he has paid to bring me here and bought me clothes to wear, not that he asked or that they were anything I would have chosen for myself but I seemed to have any choice....

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Unorthodox Methods Pt. 02

The impregnation gangbang continues, with double penetration.

Author's Note: Please read Unorthodox Methods 1 in order to understand what is occurring in this chapter! *** "Who wants to fuck me first?" I said with a smirk. Men pushed eachother out of the way, scrambling to enter my pussy. I heard still more zippers and clothing falling to the floor. I felt hands on my legs, spreading them wide, and fingers grabbing at my hips and ass and...

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Life and Time of Lady Vargos Ch. 04

Dreams and the Spa for Martin Hastings.

The Martin Hastings Saga" is a work of erotic fantasy/fiction in three distinct pieces and is not based on any beliefs/realities or are any of the characters based on person's alive or dead. This story contains elements of b/d, s/m, forced femininity, and some explicit scenes of gay sexual activity, some non consentual in nature. The story is meant to be a piece of erotic literature for...

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