Sort by
Relevancy

Free Stories

83%
Janine awaits
My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... Read full Story
bunny cat 2019-02-04 3,993 Crossdresser Masturbation Blowjob Lingerie Mature cum in mouth
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 14,082 Masturbation cum orgasm cumshots prostate
100%
Camming down the rabbit hole Ch3
Slowly stirring from my sleep, I stretched under the covers and a pleasant sensation spread across my torso, remembering what I was wearing when I went to bed I smiled at the caress of the fabric on my skin. It was a strangely comforting feeling, the pressure from the bra, panties and nightie felt l... Read full Story
Dani_does_Dallas 2021-08-18 5,447 Stockings Crossdresser solo Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade
100%
The Mind Flip
IT was a weekend like any other, in the city in the north of England. Rain poured in sheets down the basement windows of the flat I shared with my friend Joe, breaking up the shapes of the buildings on the opposite side of the road like a kaleidoscope, and I sat indoors, slouched in front of the com... Read full Story
shemale lover 2013-01-17 5,576 hardcore Blowjob Big Cock Lingerie ass fucking
100%
Camming down the rabbit hole Ch6
In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... Read full Story
Dani_does_Dallas 2021-10-11 5,124 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
100%
Fifi La Femme: A Pansy at Last Chapter 2
Coming Out Telling our wives wasn't easy especially for me who had seduced Shirley's gorgeous hetero husband by dressing up in my wife Doreen's lingerie and make-up and offering him full homo sex as a limp wristed effeminate lady-man. It was my first experience as a queer and when Frank asked me ... Read full Story
shemale lover 2012-07-29 4,874 Cumshot oral sex sissy
100%
Womanhood for Jenny
The muted alarm-clock brought jenny awake instantly. She reached over to shut it off. Being ever so careful not to disturb Master, she slipped out of bed and gazed lovingly at the sleeping man. From their earliest intimacy, He had accepted her completely as a woman, His woman, not a trans-gendered m... Read full Story
shemale lover 2012-10-07 6,046 hardcore Sex Toys tg
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 11,203 Fetish crossdressing feminization
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 4,460 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
91%
Southern Hospitality Ch. 02
XtinaSmith2017 Laura felt herself lifted lazily from the arms of sleep, her body relaxed and floating on a small cloud of pleasure, her mind filled with images, sensations, not pulled from whatever dream she had just been having but instead, memories, memories from the night before. Memories of... Read full Story
Gwapo67 2022-05-16 4,858 Bareback Creampie Shemale Fucks Guy Big Cock Mature
100%
Don't Go Into The Woods
Prologue I am standing here wearing a red plaid schoolgirl uniform skirt. It is so short that although I looked in the mirror before and couldn’t see my white satin panties I felt anyone looking at me could. My blouse is a white collared blouse typical of what you’d expect to see on a... Read full Story
shemale lover 2011-11-10 5,352 sucking Lingerie spanking
100%
Just One of Those Days Part 2
Hello again. My name is Amanda, though sometimes I use the shortened version Mandy, when the mood suits me. I'm 33 and have stayed single for three years, since I discovered that Richard, my boyfriend, was not only cheating on me with dozens of women, some my so called friends but was al... Read full Story
shemale lover 2011-12-09 3,385 cum massage shemale sex
50%
A Perfect Life
The reasons I am not writing this myself. I have finally convinced someone to do it for me. She promised to post it on the Internet, but only as fiction. I suppose it is a bit unbelievable. It all started with the best of intentions. I had married my love while we were still in college. She... Read full Story
shemale lover 2012-05-05 12,842 transgender
100%
Flowers in the Heart Part 2
Chapter 1 "Hey Scott, Fauna kind of likes you," Jenna said, snickering. "Hey Jenna, it hard to hear yourself over that echo?" Scott said as he caught the football, and then heaved it back to Ronnie. "Huh?" Jenna asked, puzzled. "Yeah, your head up your ... Read full Story
shemale lover 2012-11-11 6,429 sucking oral sex facefucking
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 14,290 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
80%
Office Policy
“Ok ladies and gentleman, please put your hands together for the beautiful and talented Erika!” the DJ’s voice rang out over the thumping alternative beat as the object of my lust strutted to the stage. Erika’s saucy red curls bounced on her head and on her soft porcelain whi... Read full Story
shemale lover 2012-08-30 8,806 anal ass sucking threesome tits fingering sex blondie
100%
Angel on the Stage
It was three o'clock on Friday morning and Angel Jones was tired, especially her feet. She had just gotten back to her flat after six hours of working as a hostess at Madame Josephine's, and being on her feet in high heels for so much of that time had taken a heavy toll. Even worse, she would need t... Read full Story
shemale lover 2012-12-03 5,198 tranny
100%
The Mole
Police work is a paramilitary occupation. Uniforms, rank, weapons, discipline…It can be exciting and interesting for some and boring for others. Some officers seem to find lots of action during their career (or maybe it finds them) while others never use their sidearm except for target practi... Read full Story
shemale lover 2012-01-26 6,784 brunette Crossdresser Fetish
100%
Angel Chapter 6
This is an entry in the Literotica Winter Holiday Contest, and is part of an ongoing series on the life of Angel Jones, a beautiful young T-girl in London. For more detailed information on her and on the other characters who appear in this story, please see previous episodes. Angel Jones was uns... Read full Story
shemale lover 2012-12-01 4,424 Cumshot oral tgirl
75%
Aunt trip
In 2013, after almost three years of service in Afghanistan, George Madsen, a gay Royal Navy communications petty officer, retired. His experience in the distant deserts had left an indelible mark, the memories of friends lost and challenges faced still burned vividly in his mind. Coming home was n... Read full Story
Rebba 2024-04-25 3,656 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 9,388 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
100%
Anastasia's Life
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember, not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barb... Read full Story
shemale lover 2012-11-26 7,416 Fetish cock sucking crossdressing