Sort by
Relevancy

Free Stories

100%
Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
Regina10 2020-11-23 5,271 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 34,587 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,829 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
100%
Club sex the 25yo
There’s a very special private club around, it’d meetings take place in a very secret place. It takes a lot to gain membership. You have to either have a lot of money AND a friend in the club OR you have to take part in the ceremonies for at least a year. Also you have to be willing to b... Read full Story
shemale lover 2011-12-10 5,245 anal Group Sex lesbian
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 5,041 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
50%
Freak House Superstar Come Fest
Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... Read full Story
shemale lover 2012-02-01 6,600 anal shemales Group Sex
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 6,406 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
50%
my sissy fuck scenario 1 to 3
there is also a video!!! my fantasy: 1. after sucking and fucking with him from like 9 am to 1 pm on Monday , he goes for a bike ride at least 30 km, i don't shower, he doesn't shower, while he's biking im on cam drinking smoking having fun with users, he watches me too and tells me what to ... Read full Story
Lena Scarlett 2024-11-06 155 anal Small Tits Crossdresser solo Masturbation threesome Blowjob blonde Big Cock gangbang sissy femboy Ass to Mouth
98%
When Fantasy Comes True 2
After my first threesome encounter with Jenni and her friend, getting a golden shower from three trans women was a bonus. Being drunk and now four of us snuggled in bed, i thought the night had ended but i did hope for more. I was not disappointed as Jenni's friend (Sasha) who had been sleeping d... Read full Story
Sara Banks 2018-10-22 12,022 Group Sex Cumshot Bareback Shemale Fucks Guy threesome Blowjob Big Cock gangbang domination Ass to Mouth cum in mouth golden showers golden shower
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,588 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 3,798 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
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 8,801 Group Sex Cumshot oral sex assfucking
100%
Gemini Sluts and Gang
My good friend Renee and I had set up a double date gang bang for tonight now that she was finally out of the closet and ready. She has decided that life is too short to remain in the closet and miss out on all the fun. Renee and I have so much in common. Besides loving sex, we both have a fetish f... Read full Story
Regina10 2021-04-09 4,736 Group Sex Big Tits Cumshot Bareback Fetish Blowjob blonde gangbang Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Tranny Gang Bang
Gang Banged I stood there looking in the full length mirror very pleased with the image I saw. I was ready for the evening and the first time I would be with more than two men at once. Freddy, had talk me into doing him and two of his friends in a sleaze motel. Freddy had found me on my internet... Read full Story
shemale lover 2011-11-12 4,980 shemales Group Sex gangbang
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 13,467 sucking Fetish fucking sissy
76%
Nylon teasers
They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... Read full Story
shemale lover 2012-01-30 10,210 Stockings Big Tits fucking foot fetish
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 15,655 first time ass Cumshot suck cd sissy make up
91%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 19,736 Big Tits sucking ass licking fucking
100%
Case of the Jealous Transsexual Chapter 2
Dee-Dee was becoming a little possessive after the 2 times that we had seen each other. She began calling me everyday, emailing me, wanting to know when will we see each other again and so on. To tell you the truth I had moved on. I had done everything with Dee-Dee that I felt could be done on a phy... Read full Story
shemale lover 2012-03-19 3,526 Group Sex Big Tits Cumshot
50%
Discovering Mistress Sarah's World Part 5
Chapter 13 Sinking Deeper Into The Feminine World *** Prologue - Joe has made a trip down south to visit for the first time, his online Mistress. Over the past few years she has slowly feminized him with the help of Miss May. Upon his arrival at Mistress Sarah's house, she puts his feminization i... Read full Story
shemale lover 2012-10-03 3,877 Group Sex oral fingering domination
100%
Florida TG Experience
I had known Jan from High School, we always had an attraction for each other but were dating someone else or married at the time. Jan had actually married a friend of mine and I was envious of course. She at that time had sandy blonde hair, and a body to die for. One evening we had them over for dr... Read full Story
Jon Paul 2018-08-13 11,431 Group Sex Big Tits Bareback Creampie Blowjob blonde Asian Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth double anal
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 4,558 anal sex Group Sex cum Latex
87%
Fem Firm 3: The Return Of Frankie
PART 1 THE VISITOR Over the next couple of months, it was pretty much business as usual at the Firm. You know, depositions, court filings, motions, hot sloppy blow jobs and ass destroying anal sex (Thanks Angela!).Not to mention Friday Fuckfests. But since I started working here everyone se... Read full Story
bennyx709 2016-11-14 12,572 anal sex ass fucking oral sex cock sucking thick cock
100%
From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
hippocampus_171 2023-01-11 4,644 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
0%
Tara's Adventures
Part 1 I had met them on line. Marla 1st then her owner Mistress Olivia. We chatted for well over a year and had met for drinks. They knew of my submissive fem side and we had planned meetings on several occasions but things always developed that upset them. Then a period of time developed whe... Read full Story
shemale lover 2012-08-11 5,486 anal Group Sex oral domination sissy
85%
A Glory Hole for Tranny G
I am reveling in what a difference almost a year has made. I remember meeting Chris online, exchanging a few funny e-mails, two days after my birthday. No more and no less, just a person somewhere who I had no idea what he was like or looked like, but someone who made me laugh with our e-mails each ... Read full Story
shemale lover 2012-03-07 3,612 Group Sex licking sucking cum gagging
75%
Fucking Insatiable
* Draenei futanari, as many of us have become intimately aware, are fucking insatiable. For many of the same reasons, they also have a tendency towards entitlement and ego issues. This is hardly surprising, being a magically-fueled blue-skinned space-babe with positively porn-star T&A and a d... Read full Story
shemale lover 2012-12-07 5,971 sucking gangbang Futanari
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,522 Fetish transformation dildo
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 5,949 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 31,419 strapon porn
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 12,264 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
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 10,869 Masturbation Blowjob blonde ass fucking big boobs
87%
They Were Right
They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... Read full Story
shemale lover 2011-12-29 6,091 shemale Big Cock porn
50%
Escapade
I'll never forget Homecoming this year. My boyfriend, Blake, came by my dorm to pick me up around 6 pm. He was in a very excited state and I could tell something was in the works. I asked him why he was so hyper and he told me that he was about to win the sex escapades, which was an annual challenge... Read full Story
shemale lover 2012-04-19 4,536 Cumshot oral sex deepthroating sissy
100%
GRANNY TRANNY'S HOUSE of SIN
It all began after my husband died and I was living alone. I decided to adopt a family and corrupt their minds. You see, I'm an ex SHEMALE PORN STAR and I like to live a wild life and I figured after my husband died I should relive my wild life and be happy. I reached over for my GOLD METAL MESH CIG... Read full Story
BITCHGURLvr 2024-11-07 7,480 shemale cum sex Cigarettes
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 8,889 anal ass sucking threesome tits fingering sex blondie
50%
Transvestite father异装癖的父亲和儿子被农民工虐待
'migrant worker S, good at foul language and humiliation, SP, heavy hands, is it acceptable?' On the SM dating software, a message popped up. Migrant worker S. What the hell? I casually click on his information, 39Get 186 and 76, dynamic is full of handsome muscles, muddy shoes, a glimpse of gar... Read full Story
Oldslut Sissy 2024-08-21 2,167 Amateur Big Cock Asian Sex Toys Mature sissy chinese
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 4,155 big dick shemale oral sex crossdressing
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 18,340 big dick anal sex suck Blowjob cock sucking workplace
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 3,735 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,920 Cumshot Masturbation oral sex
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,650 Crossdresser sucking Big Cock ass licking big boobs
100%
Becoming Paula
I work in an office with 15 coworkers about 11 of them are women. I get along well with my coworkers and go out of my way to be helpful. I find it is more fun to work with friends than to work with strangers. My name is Paul and I work in an insurance claims office processing claims and making recom... Read full Story
shemale lover 2012-04-05 6,714 anal sex orgasm fingering
100%
Eve Quest
Chapter 1 My name is, or maybe we better make that was, Andy Moore. Until recently my personal identification was in the name of Jamie Jo Moore and everyone I knew called me Sissy. My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,... Read full Story
shemale lover 2012-04-21 6,645 domination oral sex transvestite
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 14,432 hardcore sucking ass fucking Guy Fucks Shemale
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 14,551 Fetish bdsm crossdressing bisexual
60%
The Creators: Book One by
Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... Read full Story
sagga 2018-09-18 30,668 Teen (18+)
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 9,862 transgender toys bondage and discipline heavy
85%
The Greatest Lie Part 14
For me, my hometown, L.A., is not the sexy, sweaty night clubs of West Hollywood nor the porn scene of the North Valley. Though I feel more at home there, that side of L.A. is not my home but rather the world into which my transsexual destiny exiled me. Home is the leafy, moneyed boulevards and s... Read full Story
shemale lover 2012-01-20 6,263 cum transsexual fantastic
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 12,908 transgender
85%
THE WEATHERGIRL BY B-MAN
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 2015-07-29 7,911 Crossdresser hardcore ass fucking cd
100%
A Downtown Moment
I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the compa... Read full Story
shemale lover 2012-02-28 5,088 pantyhose mistress
100%
MISTRESS'S TERROR
The night had ended EXTREMELY PLEASUREABLE with BILLY, RYAN & PETER in a literal BANG and I was HAPPY. Now that BITCH I were married with our diamond 2 carat engagement rings and diamond wedding bands we were LESBIAN LOVERS. We were perfect together, Aunt Susie had groomed me into a SHEMALE DOMINATR... Read full Story
BITCHGURLvr 2024-07-01 5,697 cock transsexuals smoking cigarette