Latest Crossdressing Sex Stories

Mistress Sylvia Pt. 02

A Fag-slave Fantasy.

Having gotten a good look at what would be his future living quarters, Debbie followed Mistress Sylvia through a doorway and down a second corridor of bedrooms. She explained that the rooms were where the fags did their whoring, and the door at the far end of the hallway was the client's entrance. Just before the end of the hall was a set of double doors on the left that opened into the playroom....

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Worthy Prey

As Humanity reaches to the stars, the Isiri push back.

Dickgirl Aliens X Human Females | Non-Con | Domination | Size Difference * Lysera let out a low grunt as she arched her broad back, feeling the sore and stiff muscles throughout her powerfully built Isiri frame stretch and then relax some, helping to work a bit of life back into her uncomfortable form as her Lessers went about her orders, clearing away the human dead and providing...

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My New Neighbours Ch. 02

Katie joins in.

Apologies for the time it has taken to write this second chapter. I went on an overseas holiday and when I returned had to move house. Still settling in so hopefully, this won't be too disjointed as a result. * I closed the front door behind me and leaned back against it, eyes closed. My mind was swirling with what I had just been through. It was without a doubt, the best sexual...

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A Year Ago Ch. 19

Cynthia had been pursuing Sara, and she has been patient.

_The arc of this story will continue, but the timing may not suit some readers. After the two-year Sara's world is a bit clearer. Her relationship with Angelica and Jenn, has de-evolved. Cynthia had been pursuing Sara; she was patient, and she felt comfortable with the idea that Sara's libidinous behavior, with other women, might bring Sara back to her. After running from Angelica, Thomas and...

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Sarah went to Work at a Hotel

Sarah works at the hotel and meets a couple with a surprise.

By now, I had been working as a maid in a hotel for a few weeks. It was an LGBTQ friendly place and so I got to wear my French Maid's outfit while working. I loved walking around being seen dressed as a girl and not just dressed as a girl but wearing a sexy maids outfit. I knew that my suspender straps showed and I loved to show glimpses of my panties. The pay was good but the fringe benefits were...

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Mistress Sylvia Pt. 01

A Fag-slave Fantasy.

Debbie arrived for his counseling session with his therapist Anne O'Malley at 8 pm. As he sat in the waiting room dressed in his maroon, Laura Ashley, wide-wale corduroy dress he wondered why Anne suddenly wanted him to dress in drag for a session. He was puzzled too by the fact they were meeting at night. That had happened only once before due to an emergency on his part, but as far as he knew...

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Daddy Jack Pt. 02

Angel and Jackie misbehave.

"Oh my God, look at you, Jack," Melanie declared as soon as I let her through the door. My first thought was that my boner was sticking out the flap of my boxers. The sudden interruption had reduced it to a semi, but it could easily be drooping out. I tugged on the T-shirt I'd hastily pulled on, but it didn't reach very far past my waist. "Hi, Melanie," I said. I was breathing...

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Sarah Had to Give a Blowjob

Sarah was caught masturbating and made to give a blowjob.

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ---------------------------- After collage, my girlfriend's best friend, Alison, and I found ourselves working in the same city and so we decided to share an...

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My Therapist's Chinese Doll

Asian man is reborn after divorce.

Disclaimer: The content below has many degrading comments on certain race and sexual orientation, so please don't read it if you are looking for "political correctness". * I still re-lived the night Eunsun left me. I remember her blank stare, followed by a cold grin. She wasn't the lovely woman I once loved. She said she didn't love me anymore, and wanted to start a new life....

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Kimmy's Discovery Ch. 07

Kimmy's transformation becomes noticeable.

--- closing Chapter 6 ... Kimmy's lips had become quite full, her hair longer and more lush and any hint of boi hair on her body had vanished. They were all very pleased with the arrangements and the results. ---- Chapter 7 Dougie tried his best to not pay too much attention to Kimmy when their work schedules matched up. Of course, there were the polite 'hellos' that...

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Confession Pt. 03

The fun continues.

After receiving the message I was excited as well as tensed, I was excited for the gift but at the same time I was tensed for masturbating, after giving it a thought I decided not to tell her about this masturbation thing and if she comes to know by herself, I will accept whatever punishment she will give me. I was excited for the surprise and I thought of that I should even do something for her,...

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I Love My Breasts!

And how things developed.

I Love My Breasts! Yes, that's what I said. "I love my breasts! Boobs! Knocker! Honkers! Fun Bags! Tatas! Tits!" It all started many, many years ago. I loved stealing glances of my father's Penthouse and Playboy collection. I could barely wait for my parents to leave so I could sneak a copy back to my room, lay naked on my bed and beat one out. I had to take care not to blast my cum on...

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Kimmy's Discovery Ch. 05-06

The continuing transformation of sweet young Kimmy.

Sensations I had never experienced or even imagined continued to flow throughout my body. Lola's hand was warm, soft but firm, as she guided me to remain between her and Karen. The line to the ladies' room finally dwindled and we were next. And as one of the stalls became available, Lola and Karen pressed me in with them. My body pressed close to them, I stood there, anxious but wanting more. The...

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Life of a Bi Guy

Black man chooses between Mexican gal and Black TS.

What's good, Fam? I'm Kelvin "K-Man" Wattford and I'm a man with a big problem. Alright, let's get certain things out of the way. I'm a Bisexual man, deal with it. I make it with females and with dudes, well, certain dudes. I don't like effeminate males, I find them annoying as fuck. Sorry, but I've got to have some standards. That's not the issue in today's tale, though. The problem is that...

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Continue Crossdressing Adventures

Continued Adventures Crossdressing.

I want to thank everyone for their comments on my journey into cross-dressing, even those that were negative. It has been a number of years since I submitted my last story. Life gets in the way sometimes. For those of you that didn't read my last story let me give a little background. I stumbled into cross-dressing for my own self gratification and then as a method for my girlfriend, Sherry...

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The Futa Ring Ch. 04: An Exchange of Rings

Ali gets married.

"Sweet Persephone," he murmurs in my ear. His cock is hard and presses between my cheeks through layers of cotton and wool. "I cannot wait. I must have you now." My priorities are different, but I can multitask. "As you wish, Professor," I say, parting my legs and lifting my skirt. I bend over, leaning on the table with the translations in front of me. His hand glides up between my...

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Sarah Gets Soaked and Meets a Girl

Sarah got soaked and was rescued by a girl.

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. *** I was on vacation in Florida. On the second day, I decided to visit the 'glades. I wore a matching red bra and panty set, with a white t-shirt that I could tie...

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The TS Paradigm Shift

A fading marriage leaves him open to new experiences.

That cute little punk chick sashayed past me again and I was starting to get worried that I was going to get busted staring at her ass. The problem was that those tight black jeans fit her so well and the ragged cut-off shirt that she was wearing accentuated her heart shaped ass and revealed the intriguing dragon tattoo that appeared to start below her belt and go over her shoulder and down her...

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First Time for Daddy's Girl

Young, Sissy CD's First Time with her Daddy.

I had been talking to him for a while now. This man. Daddy. Somehow the constant barrage of pornographic images and sissy hypnosis had taken a hold of me and brought me to the point where I had actually begun to develop a relationship with a man. I had never thought of myself as gay, or had thoughts about men. I was the typical A-student, moderately athletic, all-American guy that his fair...

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The Good Friend Ch. 01

James meets his "Best Friend" Olivia Jones.

My first story submitted. Everyone involved with any sexual acts are 18+ of age. It's not gonna be a quick 1st chapter. This is a background story and not a "stroker." If you feel compelled to criticize, be constructive please. Also looking for anyone willing to help edit my writing. I am still an amateur compared to most common writers. -The Defective Detective * The...

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Minimum Security Prison Bitch

TransWoman is sent to a facility modeled after Bastoy Prison.

Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows? As my regular readers are aware, I enjoy writing about the transgender experience from different perspectives. Here I write about a transgender woman whose experiences in prison were quite different than she expected them to be. ~~~ Chapter 1....

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Confiding in My Hairdresser

Had the urge to admit my crossdressing to my hairdresser.

I've always had a great relationship with my hairdresser, Mary. She'd been cutting my hair for years and we probably shared a few more details than we should about sex, she made me laugh at some of the naughty stuff she'd been up to! On occasion around a year ago, she came to the new house that I'd just moved into with my girlfriend to cut my hair. The chair was facing the back garden...

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My New GF has a Dick

And I love every last inch of it.

I didn't go looking for a tranny, shemale, dickgirl, or whatever derogatory term a homophobic world has labeled women that happen to be packing a penis. In fact, while I had messed around a little with the man worm, back in college and with a drunken buddy a few times, I considered myself 100% a hetero male, in love with the female form and a total horn dog for a beautiful woman. I must admit,...

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Sarah was Trained to be a Girl

Sarah is trained to be a girl and meets a girlfriend.

I love to search on-line for sites related to crossdressing, that's how I found Literotica. I've also found sites for 'Men in Panties', videos of crossdressing, girls clothes for men, etc. One time, I was really lucky, I found a site offering a weekend of 'girly training'. We would be taught how to walk, sit and act like a girl. We would be dressed the whole weekend and only go by our girl names....

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Neighbors Delight Ch. 01

Accepting The Package.

It was Friday, the alarm rang; my wife reached over and turned it off as she got out of bed to get ready for work. I was a male nurse and had a three day weekend as usual; and as usual I got up and fixed breakfast which was toasting the bagels, cream cheese, and making coffee. "Honey, I have a surprise," she said excitedly as she entered the kitchen. "What is it?" I asked curiously....

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My Neighbor's Submissive Ch. 05

Our relationship becomes more formal.

Chapter 5 - His Personal Servant I was up early the next morning, still feeling high from the new depths Edmund and Mr. Karlsson had taken me the day prior. I was used as a domestic servant, and as a distraction for Edmund to gain advantage during their negotiations. I started in anonymity behind a mask, but ended up exposing my face to his guest, so both men could paint it with their copious...

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The Roommate

A man is stunned to find out his roommate is now a t-girl.

In hindsight, I should have seen the path I would eventually end up on. The signs were all there when I was younger. It's hard to see the truth about something when you're in the early stages of it. My name is Denise Christensen. While I may have been born a boy named Ander, my life is now lived as a woman with ... more. This is the story of how that change unfolded. To understand how...

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Losing My Maleness To Become A Girl Ch. 05


Well it finally has happened. I am now married to Peter, fully and legally. We had two ceremonies - one in a registry office and one in Nigeria, and I am now Mrs. Chrissy Ndidi. My passport bears his name, all my credit cards, my registration with doctors- everything. And I am the happiest woman alive. Here is how it happened. I wrote in the last Chapter of my happiness as a woman, of our...

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Sarah Asked to Work as a Hotel Maid

Has to service not only the room but the guest.

A few weeks before the events described here, I had watched a transgender porn video. It was about a guy who dressed as a French Maid and worked in a hotel. I was so excited by what happened to him, I wanted to give it a try. I searched on-line for an LGBTQ friendly hotel and found a promising one close by. I emailed them and asked if I could tryout as a 'maid'. They emailed me back with a date...

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Abby's Tail

A short prequel to Becoming Abby.

_Note from the Author I would like to take a moment to thank everyone that has been reading along with Abby's adventures. All of the comments, and private messages, have been really encouraging. Please don't hesitate to comment or send me a mail. I always try and respond to each of them. This is a stand-alone short story that I wrote several years ago about Missy and Abby. With a...

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