Sort by
Relevancy

Free Stories

100%
Debbie Part 8
Moira sat in her booth at the entrance to the subway station and saw people pass by. She sat there every day selling tickets, and although several thousand people passed her during a shift, she could now recognize many of the regulars and she even knew when to expect them. It was now almost 9 o'cloc... Read full Story
shemale lover 2011-12-23 7,609 transgender toys bondage and discipline heavy
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 6,119 hardcore Sex Toys tg
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 5,488 Stockings Crossdresser solo Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade
50%
My friend Barbara,
My friend Barbara, I look forward to welcoming Barbara. She is a lovely brunette with blue eyes who likes to make love without taboos. She knows how to bring our fantasies to life by imagining exciting role-playing games. - You're going to fall in love when you discover my underwear, she assur... Read full Story
sandratvtg 2024-07-04 3,137 Stockings Bareback Fetish transsexual Lingerie Sex Toys travesti Vintage rosebud plug gonflable gode xxl
50%
My desire to be a woman,
My desire to be a woman, Natacha, tall and slender, stands in front of me. Her hair tied in a ponytail refines her face, emphasizing her Dominatrix profile. She wears a lovely nightie and a corset highlighting her magnificent breasts. She is perched on stiletto heels topped with thigh-high... Read full Story
sandratvtg 2024-07-04 3,214 anal Stockings Fetish Lingerie Sex Toys femdom travesti Vintage gode speculum donjon pussy pump castration play
50%
A Revenge Fuck
It had been a long day. I had fought the traffic after a miserable week to get home early and surprise my wife for what was to be a romantic weekend. But as I pulled up to the house my heart sank. I saw a bright red motorcycle in the drive way and something inside told me, "This isn't right!&qu... Read full Story
shemale lover 2012-06-03 11,464 shemale oral sex Interracial
100%
How I Became Vanessa Chapter 1
PART I: I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husba... Read full Story
shemale lover 2012-10-31 4,019 anal Cumshot Masturbation Sex Toys
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 5,181 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
100%
Natacha's dungeon,
Natacha's dungeon, For a long time, I have loved wearing lingerie because it always gives me so much excitement to contemplate myself as a woman in front of my mirror. I learned a long time ago to memorize feminine gestures and attitudes while perched on my pumps. I also know how to put on ma... Read full Story
sandratvtg 2024-06-24 3,034 anal Stockings Shemale Fucks Guy Fetish Lingerie domination Sex Toys femboy chastity cage plug urétral
50%
My transvestite evenings at the hotel,
My wife didn't want me to wear lingerie at home, so I ended up living my femininity without her knowledge. Cycling in my area, I took this excuse to start shaving my legs regularly like most cyclists do. Then, spending my holidays regularly on sunny beaches for surfing and sailing, I used aesthe... Read full Story
sandratvtg 2024-07-02 2,931 anal shemale Lingerie Sex Toys exhibition Vintage guepiere bad dragon dildo estim culotte fendue fémidom resebud
100%
THE WONDERFUL ADVENTURES OF MISS K: QUEEN OF THE ROAD
Miss K drove the car through the Midwestern countryside, enjoying the early spring breeze that leaked through the SUV's window as it blew through her platinum blonde hair. Her tits were held up by the tight, white, midriff-baring top she wore that stopped just below the lower curve of her tits... Read full Story
shemale lover 2012-01-28 4,236 licking sucking fucking Sex Toys
100%
A Dare Gone Right
'Well, Paul, if you're not man enough, just say so!' 'Come on, that's not fair, Isabel. I've never dared you to do anything this risky,' I replied. 'Oh yeah? Walking around the mall in a pink latex micro-skirt and no panties wasn't risky? My balls were swinging around for all to see!' 'Yeah... Read full Story
shemale lover 2012-02-26 3,763 dildo Sex Toys
50%
A Married Marilyn
"Class is dismissed. Don't forget the project due…" "Huh, what?" Marilyn woke up disoriented from her nap. When she finally came to, she vaguely remembered some project for Intro to Computer Science, gathered her legs from the chairs in front of her, dusted off her b... Read full Story
shemale lover 2012-03-18 7,447 Group Sex Masturbation sucking Sex Toys
100%
The game show,
One day i was looking through a number of competitions and trying to find a way to make some easy quick money. A number of applications were sent, mostly for junk i didn't need or for competitions I knew I had no chance of winning. For example, the types you get $30,000 for answering the easiest que... Read full Story
chris1989r 2022-01-24 5,127 Bareback Shemale Fucks Guy Ebony gangbang Guy Fucks Shemale shemale + shemale
100%
Surprise Ending (Part Three)
I rolled my dick around her hole to spread the precum off it and lubricate it. The feeling was sensational and I couldn't spend much time easing my way in --I shoved right in the the hilt in one steady push. Karla practically jumped off the couch and screamed. I thought maybe I had hurt her (I am... Read full Story
Chantel13 2022-08-23 4,610 Crossdresser Amateur Group Sex Cumshot Outdoor Creampie Shemale Fucks Guy Big Cock Shemale and Girl redhead Guy Fucks Shemale Ass to Mouth
50%
DATES NUITS
My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... Read full Story
Femboy 2021 2023-02-07 1,660 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial Sex Toys cum in mouth
100%
Amanda and Me Chapter 2
I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... Read full Story
shemale lover 2012-10-21 8,958 anal Cumshot shemale oral
94%
MILF Alessia Travestita finds a bottom boy
I was several days into a cruise to New Zealand and Australia with my wife. This morning my wife went on an excursion that I had no interest in, so I had the cabin to myself. I hadn't had any sex with my wife in the last 3 days due to the activities such as the various jaunts to Auckland and the sur... Read full Story
darrell 2023-08-13 6,576 anal Cumshot Shemale Fucks Guy Fetish blonde Big Cock domination Mature deep throat cum in mouth sandals
60%
Amy's Surprise 2: Enter Karissa
What did you think? Amy asked. Well, let's see, I started to answer, You gave me the best blowjob I've ever gotten, sucking your dick was about the best thing ever, and sharing your cum with you was incredible.all in all, I'd say it went well. Amy smiled and walked over to sit with me on the couc... Read full Story
shemale lover 2012-05-08 4,774 anal sex shemale Sex Toys
83%
Fun with a latina tranny
So I'm a big fan of a big tranny cock in my ass. Just throwing that out there early on here. So this past summer I decided that with my school being off I should get some tranny cock as fast as I could. I went on a site and set up a new account, hoping for the same luck I had a few months ago wit... Read full Story
shemale lover 2012-09-15 3,857 anal Latina cum oral Sex Toys strapon
50%
My Parisian escapades,
My Parisian escapades, During my many business trips to Paris, I never miss going to see my friend. Sabrina is a Cuban transsexual that I have known for several months. With her, I can let go with complete confidence and live my fantasies. I am one of his friends and lovers who give him the ... Read full Story
sandratvtg 2024-06-25 2,925 anal Stockings Shemale Fucks Guy Fetish Lingerie Sex Toys sissy wig gode pumps rosebud silicone breast split panties
75%
Encyclopedia Erotica By The Fan
It was a normal-looking enough place. A small town in California. Looking at it, no one would ever guess it sat on the hellmouth. The Mouth of Hell. A portal to a multitude of dimensions filled with horrors and wonders. Many things came to the Hellmouth, drawn by its power. Vampires. Demons. Mon... Read full Story
shemale lover 2011-10-19 4,667 asshole orgy Sex Toys
85%
A very hot encounter
I've had been feeling way too horny for days; masturbating every night to shemale porn. I've always loved transexuals. There's nothing better than a very hot body with a fairly large cock to be sucked and drained of hot cum. There's something even kinkier for me about a top shemale. I imagine that c... Read full Story
shemale lover 2012-07-08 4,846 anal Cumshot oral Sex Toys spanking
84%
She never saw it coming
When I was 19/20 I used to frequent LGBT bars roughly twice every month. Most nights not much would happen but I found myself going to the trans nights more often. Until I eventually had some experience with trans girls. It was mostly fairly soft fun. Me getting oral and occasionally topping th... Read full Story
chris1989r 2022-02-01 5,442 shemale gangbang facial
50%
trans=demic
Trans-demic Chinese Flu Sam Wong read the email from Josh Epstein, the partner in charge of the fiendishly complicated real estate deal that had consumed the last three months of their lives. “You’re going to have to close this deal without me. I’m sick as a dog, and my wife just called an ambu... Read full Story
the greatest liar 2024-09-09 1,496 anal Small Tits Bareback Creampie Asian Guy Fucks Shemale small cock Ass to Mouth cum in mouth
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 7,591 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
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 14,493 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
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 31,429 strapon porn
40%
Dating all whole my life
Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... Read full Story
PornoDating 2019-08-15 4,285 Crossdresser Amateur Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock Asian gangbang domination Guy Fucks Shemale Interracial sex Mature Futanari Frottage Compilation Ass to Mouth Cartoon cum in mouth double anal dating life in Mars? life
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 9,226 Stockings sucking domination
71%
Filthy Little Beast
I had very few memories of my early childhood. The ones I did have were anything but pleasant. I did remember my mother and her blind hatred of my father and myself. She was very tall blonde woman with cold blue eyes named Monica. My mother always dressed in the most expensive leathers and satins in... Read full Story
shemale lover 2011-12-02 12,766 taboo Fetish crossdressing erotic encounters
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 5,470 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
66%
Cassandra Chapter 1
Cassandra is a tease, a flirt, a slut, a girl who lives very much for the moment. Unconcerned with propriety or fashion trends, she dresses in clothes that go right for the jugular of a fetishist's libido. Spandex, leather, latex, spike heels, corsets, overdone hair, make-up and fingernails - these ... Read full Story
shemale lover 2012-03-27 6,129 sucking fuck orgasm crossdressing
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,371 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
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 2,647 anal Lingerie femdom submissive femboy huge toys
100%
How My Wife Became a Swinger
Hello, my name is Jackson, Jack for short, and I'd like to tell you about my wife and I and how we became swingers. I've changed the names of people and places to preserve privacy. Just so you know this does involve male on male sex and inter course with a transsexual. So let me begin. For the fi... Read full Story
Loveto 2011-10-12 8,963 anal bisexual gay strap-on
50%
How My Wife Became a Swinger
Hello, my name is Jackson, Jack for short, and I'd like to tell you about my wife and I and how we became swingers. I've changed the names of people and places to preserve privacy. Just so you know this does involve male on male sex and inter course with a transsexual. So let me begin. For the fi... Read full Story
shemale lover 2011-11-13 5,465 Group Sex Cumshot sucking doggy style
100%
Becoming A She-Males Bitch Part 2
After last nights ordeal I was given something to drink and taken to a bedroom upstairs. What I drank must have had some kind of drug in it because I was knocked out. I bet I was asleep in just a couple of minutes. I barely even remember lying down. When I woke up I was naked, sore as hell and fe... Read full Story
shemale lover 2012-01-04 9,101 cum oral domination
50%
Giving Away Virginia Holton
Today would have to wait, thought Marla Holton as she hurriedly gathered her bag and notebook in preparation for a no-holds-barred departure from her office at Prism Design. As general manager she had the privilege of arriving and leaving at will, though no one could ever fault her for not putting i... Read full Story
shemale lover 2011-10-08 4,797 shemale cum ass fucking
58%
My real story
I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him. It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willi... Read full Story
shemale lover 2012-06-10 6,582 hardcore Cumshot bdsm oral sex
100%
The Seductive Seed of a Tranny MILF
The Seductive Seed of a Tranny MILF SugarandSalt Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spo... Read full Story
Gwapo67 2022-05-03 8,190 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
Couple and a Tranny
There is a saying that a single man looking for companionship and good fortune will seek someone for marriage. Lydia and I met several months ago on an online dating site. We agreed to meet at a bar restaurant for drinks and initial meeting. She was at the bar wearing a yellow sundress, white painte... Read full Story
Jon Paul 2022-09-20 5,659 Cumshot Outdoor Latina Bareback threesome Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth double anal
50%
Liberty meeting, chapter1
On a beautiful summer day, my phone rings. It's Steve, the boss of a transvestite company who calls me. - Hello Sandra, I have four new friends waiting for you at the club. - Thanks for thinking of me, I'll be right there, I said, hanging up. I am happy with his call because I always meet ... Read full Story
sandratvtg 2024-06-20 2,751 Stockings Shemale Fucks Guy Fetish Lingerie shemale + shemale
100%
Changling
‘My goodness!’ she exclaimed, ‘It appears that you've had an accident, youngster. You'd better come home with me so that we can make you presentable. It's quite safe, 'cos I live in the big house in the woods on the other side of the hill behind the toilets. Come along, now,’... Read full Story
shemale lover 2012-02-02 8,983 shemales Masturbation Big Cock
100%
David to Dee Chapter 2
His nipples had grown considerably over the last two months. Gina had been putting those little nipple suckers on him twice a day. Dave wouldn't be going to the gym anymore. Well, it had been a long time since he'd gone to the gym, anyway. Since Gina had had him shave his entire body, last spring... Read full Story
shemale lover 2012-07-30 6,013 anal sex Cumshot oral sex rimjob
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 6,127 anal Cumshot Latina Bareback Creampie threesome Shemale and Girl Lola
83%
Teacher Student Confidentiality
It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... Read full Story
shemale lover 2012-02-11 14,357 anal Blowjob black fiction
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 4,751 anal cum oral
100%
Transsexual Sisters Chapter 6
Part 6: A Party to Remember MICHELLE AND NICOLE MAKE A CAREER CHOICE After their tormentors were jailed, Michelle and Nicole felt relieved and happy for the first time in weeks. Whether from curiosity, respect or sympathy for their ordeal they became very popular around the USC campus. They we... Read full Story
shemale lover 2012-09-08 4,347 Cumshot sucking threesome Shemale and Girl deep throat
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 9,453 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
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 3,736 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
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 6,852 sucking cum massage
94%
Crossing lines
It had always been a fantasy of mine. I have very feminine features and long natural straight brown hair. Which recently I had shortened to chin length. I have been dressing in womens clothing now for many months and had decided that this was the night in which I get made up totally and head ou... Read full Story
Zöe from Kingston 2019-02-04 11,405 Stockings Crossdresser Cumshot Outdoor Bareback Shemale Fucks Guy Blowjob Big Cock Ebony Guy Fucks Shemale Interracial
80%
How I Became Vanessa Part 1
I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husband moved to... Read full Story
shemale lover 2011-09-09 4,535 anal sex shemale dildo
100%
Buying Time
It’s a hundred dollars to use the sex machine in the public restroom. Insert a couple of fifty-dollar coins into the payment slot to remain anonymous, though of course it’s more convenient to just let the data terminal do a neural scan and auto-debit your account. A hundred bucks buys... Read full Story
shemale lover 2012-03-25 4,065 anal sex Cumshot shemale
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 18,345 big dick anal sex suck Blowjob cock sucking workplace