Sort by
Relevancy

Free Stories

100%
Stepping Out
All through the next week we searched through almost all the online dating sites and it was the same as before. Some wanted just me or just Deena, but not the both of us together. One good result was that I found a trans gender support group and they were going to meet on the next Tuesday which was ... Read full Story
Setinkhan 2021-06-02 3,319 Crossdresser Fetish Big Cock Interracial cum in mouth shemale + shemale
74%
My Daughter and I Visit a Lesbian Bar
It is an extremely warm Saturday night and my eighteen year old daughter Krissy and I are sitting around in the house having conversation while we drink sparkling wine. Around midnight I suggest it might be fun if we took off our clothes and sat outside on the front porch. Krissy giggles for a few m... Read full Story
shemale lover 2014-03-17 8,816 shemales Group Sex lesbian sex
84%
I posted a craigslist ad
8 years ago I began crossdressing again and playing with toys. After playing one day while watching videos online I decided I wanted to take the next step and be with a man again. My holes craved it but the butterflies in my stomach had stopped me before. Afraid they would do it again this time I go... Read full Story
shemale lover 2016-04-26 10,511 shemales gay male interracial sex
86%
Alex’s Bottom Slut
So when I was younger, I worked at a pizza place as a delivery guy. It was a pretty boring job for the most part but that all changed one night. I got a delivery to just outside of our range but decided to take it anyways because we were slow. When I got there a very tall and muscular black woman in... Read full Story
Jsmithsub 2019-11-18 57,251 Group Sex Cumshot Shemale Fucks Guy Blowjob Big Cock Ebony gangbang domination Interracial Ass to Mouth cum in mouth
100%
College project surprise
So this story happened while I was still in college and remains without doubt, the craziest, most exciting experience of my life. So I the story begins one day when I walking to class. I went to a big university so my walk was quite long, and the first 1/3 was just through off our campus housin... Read full Story
Jsmithsub 2020-09-16 21,563 Group Sex Bareback Shemale Fucks Guy Fetish threesome Big Cock Ebony domination Ass to Mouth cum in mouth
95%
First time
Hi, my name is Sandra. In fact, I'm not exactly a girl, but a CD. Even as a child, I felt different and I used every opportunity when I was left alone in the apartment to dress up, to put on women's clothes, to put on make-up. In time, I started watching porn, as did all my friends. But, unlike them... Read full Story
cd Sandra 2021-10-13 5,930 Stockings Teen (18+) Small Tits Crossdresser blonde Guy Fucks Shemale
100%
I Believe
I Believe I had just started my senior year in college and was in my 3rd year of transitioning from a male to a female. I couldn’t start in high school so when I graduated and I started college I started as Nikki. The first three years working on my communications degree I used to see people goin... Read full Story
ShelleyParker 2024-07-08 3,171 Bareback Big Cock Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
100%
Blushing Bride Chapter 4
Chapter Four: The Hen Party I've already told you all about the night a couple of days before my wedding, the night of my stag party, the night where I got to live out all my fantasies and play the blushing bride, dressing in my soon to be wife Gina's gorgeous white wedding dress and lingerie and... Read full Story
shemale lover 2012-07-21 4,102 big dick shemale oral sex crossdressing
100%
New Orleans TS dream come true..
In was on New Orleans running water for the victims of Katrina in 2005. I went down to Bourbon St several times an one night I walked into adult fetish store and as I was looking around there was what appeared to be a very beautiful black woman bending over with a very short skirt on. I was admirin... Read full Story
jim3801 2018-09-11 10,942 Group Sex Bareback Shemale Fucks Guy threesome Big Cock Ebony Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
44%
Gargantua
Women do not have penises or testicles. These sex organs are specific to men. As the boy in Kindergarten Cop demonstrates, even young children are aware of this most fundamental fact of life. However, in the genre of erotic fantasy art known as futanari, hermaphroditic "dickgirls" defy nat... Read full Story
shemale lover 2011-09-12 7,875 Futanari dickgirl big cocks
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 15,560 first time ass Cumshot suck cd sissy make up
33%
Duel With the Devil, Chapter 20 of The Greatest Liar
Duel With The Devil This is a work of fiction. All characters (including the narrator), celebrities, places, residences, neighborhoods, restaurants, legal agreements and proceedings, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any r... Read full Story
the greatest liar 2023-07-19 4,320 anal Bareback Creampie Ebony Guy Fucks Shemale post-op celebrity post op sex
100%
Tony to Tanya Part 3
Sarah finished applying make-up to Tony's face. It was mostly subtle, just enough to highlight his eyes and cheeks. The only part that wasn't so subtle was the lipstick; bright red. He was already dressed up in a beautiful black dress that left his back and shoulders exposed and only went down to... Read full Story
shemale lover 2011-12-19 4,724 anal cum oral
100%
A Schoolgirl Story Chapter 2
I must apologise for the amount of time that it has taken for the second chapter of this story to come out. I have to admit that I had kind of abandoned it, but all your lovely feedback comments made me decide that I couldn't leave this one hanging. So thank you to everyone who wanted more of Wendy,... Read full Story
shemale lover 2012-06-05 8,745 Group Sex Cumshot oral sex assfucking
66%
Dirty Business Trip
Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and he... Read full Story
shemale lover 2012-09-26 13,047 Group Sex Cumshot shemale oral
66%
Carioca holidays
My best friend was a shemale named Monica from Rio de Janeiro , she was a gorgeous and sexy brunette , many time at her home she use to tell me many story about her city and the fun you can have as a cd , also she says the guys are really hot and very well packed . One night we where chatting about ... Read full Story
Suellen blonde 2014-09-02 3,597 Group Sex suck Lingerie crossdressing cd
0%
The Greatest Lie Part 16
As soon as we were safely back in our hooch, I retrieved the iBook from its hiding place under the floor and opened up Spartan's main Excel spreadsheet. I re-sorted the list against the data from the last three weeks of our frustrating field work, by district, language group, age, and every other ca... Read full Story
shemale lover 2012-01-20 5,182 first time femdom crossdressing
76%
Porn Princess
They say if you are going on a journey of revenge, to dig 2 graves, one for your enemy and one for yourself. I thought I understood the meaning of that saying, but never so much as right now. My name is Dan, and at the age of 21, I had been working for nearly 2 years as a production manager for ... Read full Story
shemale lover 2012-09-02 24,257 Cumshot Blowjob fuck fingering big boobs
100%
Unconditional Love Chapter 8
After a two' hour nap, Alison and I awoke and the first thing we did was make our way to the bathroom to freshen up. I started up the hot water and climbed into the shower and' once she finished relieving her bladder Allie climbed in with me under the hot water and we embraced each other. We kiss... Read full Story
shemale lover 2013-02-04 6,526 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
50%
Dirty Tranny gang bang
Deep breath Charlotte, step into the night air and strut your stuff girl. This is what I was born to do; I snuggle into my short white fleecy coat as my 5” platform heels click on the pavement. Glancing down I can see my shapely stocking clad legs and, the all important, ankle bracelet glit... Read full Story
shemale lover 2011-12-27 4,896 anal shemales Group Sex
100%
European Vacation
I was 18 when I first went to Europe. That month would change my life. My parents had died when I was five, and I was raised by family friends; they also controlled my trust fund. It's not a coincidence that I went to Europe just as I came into control of the money. I loved my foster-parents, but... Read full Story
shemale lover 2012-04-21 3,976 anal sex cum oral sex sissy
87%
Feminized By My Mother Chapter 2
My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed. "I ho... Read full Story
shemale lover 2012-07-24 13,399 sucking Fetish fucking sissy
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 8,811 anal ass sucking threesome tits fingering sex blondie
100%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2013-07-18 8,663 anal sex Ebony oral sex Interracial kissing
50%
The Zodiac Coins: Libra
2400 YEARS AGO... He was a humble shepherd. It was night and the flocks were sleeping. As he gazed at the stars, he saw a shooting star. He knew it was a portent of some kind, but was not mystic enough to know what. A little while later he saw another shooting star and guessed that wha... Read full Story
shemale lover 2011-10-18 4,836 Group Sex Masturbation shemale oral
100%
A Game within a Game Part 1
Epilogue Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter. Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fas... Read full Story
shemale lover 2012-03-05 14,487 Fetish bdsm crossdressing bisexual
80%
Bisexual Black Man's Paradise
The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... Read full Story
shemale lover 2012-06-24 5,608 big dick tranny anal sex Cumshot orgy facial oral sex
100%
Afternoon Delight Chapter 3
When we got to the cottage, the girls stripped me of my jewelry and took theirs off and poured me into the shower. They washed the cum off of me and got me hard again. Damn, Ally and Carmen were all over my cock, giving me a work out. Needless to say, I came a few more times, and we got into the hot... Read full Story
shemale lover 2012-08-27 2,668 Group Sex facial sucking off
100%
One experience with two black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider myself a cross dresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine lady boy. I have been taking also hormones for 4 years, on and off and I already saw many changes&h... Read full Story
shemale lover 2013-05-16 4,619 Stockings anal sex suck threesome Interracial cum swallowing
94%
CD and BBC Gangbang 1
My name is Mike, as a "Gurl" I go by Fiona. I am a gay man, mid thrities, white, 5' 9' 165, reasonably handsome, both in and out of women's clothes. One of the ways I express my sexuality is to dress as a woman and get fucked by other men. Preferably in a humiliati... Read full Story
FionaFucked 2014-10-27 14,229 Group Sex gangbang Interracial cd sissy
72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 11,660 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
The Fabulous Alessia Travestita
Alessia is a real transexual. Several of her porn videos are on this site. She collaborated with me in this story. Alessia is a natural blonde haired, brown eyed, mature fifty -five year old Transsexual woman from England. She is tall, very fit, stands 5'11," 36B-26-30 and a slender 133... Read full Story
darrell 2021-12-14 4,578 Crossdresser Blowjob blonde Big Cock domination Mature cum in mouth
84%
The Making of Erica - Sperm Loving Crossdresser
Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I have only sucked cocks, but over a hundred at my las... Read full Story
shemale lover 2015-09-03 16,835 shemales Masturbation Fetish
82%
My shemale weekend
I arrived at Chandra's apartment about 2pm. She greeted me at the door wearing a pair of short gym shorts and a tube top. She kissed me and let me in. My cock grew hard immediately and all I did was walked into the apartment. Chandra led me into the livingroom whenre her roommate Jizelle was sitting... Read full Story
shemale lover 2015-09-05 9,663 shemales Group Sex interracial sex
66%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2011-11-14 7,012 Big Cock Ebony transsexual
80%
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 full Story
shemale lover 2011-12-23 9,793 transgender toys bondage and discipline heavy
100%
A New Girl
Still half-asleep, I purred happily when I heard the curtains being drawn. I could hear the sound of rain beating against the outside of the window, but the poor weather was the last thing on my mind. Still barely able to believe my luck, I slid my hand down the side of my smooth thigh, delighting i... Read full Story
shemale lover 2012-04-05 4,698 fingering oral sex small breasts cum swallowing
100%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2012-05-07 5,103 shemale Big Cock oral sex cum licking
66%
Would You
'Would you...?' 'Look the part to play the part....' 1 5' 4...dreaded, and to be dreaded....bookish, be-spectacled—damn near owlish....so much so that you might miss the way her tits spoke to you no matter how much she attempted to 'silence' them ....that you might miss the way her sk... Read full Story
shemale lover 2012-09-23 6,797 sucking cum massage
100%
Working for a Living Chapter 6
I slid out of the old Ford truck driver's side door. Surprisingly, my legs felt a bit shaky as my feet hit the concrete driveway of the Malibu mansion. I nervously straightened my cut-off shorts as I walked around the truck. She was waiting by the tailgate with a big smile on her face. "Wow Jai... Read full Story
shemale lover 2012-10-05 3,789 Group Sex Creampie threesome
94%
Fooled by the Wrapping
It has been about 8 months now since my husband left me. No big blowup, or much arguing. He admitted he had been having an affair his third. I admitted that I had spent an evening with a young man. He had a long talk, and agreed to move out, we could live our separate lives. I kept the house, he agr... Read full Story
shemale lover 2013-03-28 8,785 hardcore sucking Big Cock Shemale and Girl Interracial
89%
Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2016-11-14 18,295 big dick anal sex suck Blowjob cock sucking workplace
100%
Vegas Honeymoon to Remember
I had dated my wife (Carmen) for about 6 months before we decided to Marry. One evening we were soaking in the Jacuzzi together and drinking wine. She always wants to try different things, which makes our sex life wonderful. Carmen asked me if I ever had any fantasies. I said I guess like most me... Read full Story
Jon Paul 2018-05-30 20,695 Group Sex Cumshot Bareback threesome Ladyboy Shemale and Girl
100%
bi to sissy caught and turned
It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... Read full Story
redthongthong 2022-08-02 9,327 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!
100%
Lola Chapter 5
Lola chapter 5 Summer vacation was coming to an end. Most of the time we had been to ourselves, mostly at home but also a couple of shorter trips. Beer tasting in Stockholm's archipelago, a trip to the west coast, overnight stays in hotels, everywhere we were received like any other couple. A fam... Read full Story
BellaBeau 2023-10-30 6,049 anal Cumshot Latina Bareback Creampie threesome Shemale and Girl Lola
100%
The formidable weapon of women
five ears of marriage, my desire for my wife having greatly diminished, she decided to take control of my sexuality. A female association transformed her in a few months into a perfect dominatrix both physically and cerebrally. Every night before bed, she approaches me, dressed in a latex comb... Read full Story
sandratvtg 2024-06-19 2,577 anal Lingerie femdom submissive femboy huge toys
100%
Fetish party with a twist
The smell of rubber and latex and the combination of the strobe lighting was overpowering, the techno sound of the club just added to the already intoxicated atmosphere of the place. The club was a frenzy of half naked, latexed, rubberised bodies covered in sweat dancing to the frenzied sound of tec... Read full Story
shemale lover 2011-09-22 4,523 anal sex Group Sex cum Latex
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 3,388 cum massage shemale sex
0%
Headmistress' Favorite Sport Part 7
At the academy Denise and the others immediately resumed their old routines. The training for the second year slaves had started a few weeks before the new batch of sissies arrived at the academy. Not many new elements were introduced in the training as the second year was mostly about perfecting th... Read full Story
shemale lover 2011-12-13 4,784 torture toys bondage and discipline chastity belt
50%
Old Folks
I had been cross-dressing for some years, but I had never been with another man. I had been talking on a gay chat site for some months when I found someone who I got on with well. We exchanged photos I was happy with his and he was happy with mine. Deciding to get together, we arranged a date and ti... Read full Story
shemale lover 2012-01-10 8,211 transsexuals romance crossdressers
91%
A New Year's Resolution
I'm not gay (laughing), with that said, I have seen some very good looking, uh, guys. Okay, go ahead and laugh. You see, toward the end of this past summer (August 2011), my wife and I visited an old friend of mine in Pattaya, Chon Buri, Thailand. He's a former Navy Seal. I'm a former Army Ranger as... Read full Story
shemale lover 2012-04-16 7,825 anal sex cum oral sex
75%
The teenage slut
Hey folks Sandy here once again. I know every time you see me I go up one grade level but this is one tale I felt I should tell you. Let me start at the beginning after me and Bella fucked each other. Well were still together. Laughing, eating together, just having fun basically. We still fuck in th... Read full Story
shemale lover 2012-04-25 3,813 Teen (18+) Cumshot oral sex cum swallowing
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 10,834 Masturbation Blowjob blonde ass fucking big boobs
81%
Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
shemale lover 2015-02-27 7,279 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
87%
TO BE OR NOT TO BE – PART 1
TO BE OR NOT TO BE – PART 1 by Spanky de Bautumn This is a story about how taking a play to New York City changed people's lives. A transgender coming of age story. I was born Harold Stanley Dayes, not a great name for a kid growing up. I know my parents loved me, but Harold was my mom's dad a... Read full Story
SpankydeBautumn 2021-02-22 4,150 Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob Ladyboy Lingerie Shemale and Girl cum in mouth
50%
Transgender Art: A Sampler
It's not often that transgender art offers viewers a glimpse of a female-to-male transsexual. Usually, the transformation is in the other direction, with the loss of the vagina in favor of male genitals and the acquisition of female breasts. However, one image does reverse this trend, showing a fema... Read full Story
shemale lover 2011-09-06 3,764 shemale transsexual transgender