Sort by
Relevancy

Free Stories

86%
Pulled over
Kristen hurried to her car, worried that she would be late once again. She got in, slammed the door shut and turned on the engine in one smooth motion and raced off. "Damn!" she thought "the light's gonna change." She pressed her foot to the gas hoping she could make it and breez... Read full Story
shemale lover 2014-08-21 5,366 sucking shemale cum
81%
First time in Bangkok
If you have read my story about the first time I was with a TS girl then you know my experience was limited to just a few times. So about 4 years ago I went to Thailand to visit my buddy who was working there in a high profile job with the Thai government. We stayed in his apartment on the 40th floo... Read full Story
shemale lover 2015-01-13 13,625 shemales hardcore Group Sex
62%
Silver and Gold
Collaborated with: TangoKilo421 (Thanks for all your help, dood. ) A/N: It took several months, but it's finally finished. Be sure to tell me what you think. Naruto whistled cheerfully as he walked through the village of Konoha. Things had certainly changed quite a bit ever since Pein’s ... Read full Story
BoyVixen 2016-03-24 7,229 tranny Big Tits Futanari
100%
Mel - Sexy Olderman
Mel is 66 years old and is in my musical orchestra. he is handsome with a great personality. he is married but his wife is ailing ,so i dont think he gets much action!he is a horn player an i in the percussion section.mel an i joke a welot an he sometimes jokingly says i have a nice ass! he has beco... Read full Story
shemale lover 2011-10-25 2,692 Cumshot Big Cock oral
88%
A Schoolgirl Story
Jason Sheen was eighteen when he moved to River Falls with his mother. Ever since he was a small child Jason had lived with just his mother, Felicity, and he could no longer remember anything about the father who had abandoned the two of them when Jason was just three years old. Fortunately, Felicit... Read full Story
shemale lover 2012-06-05 14,945 cum oral jerking off crossdressing
85%
Busted and Hoodwinked
INTRODUCTION Mack and Barry were cell mates in prison which is where they first met. They had both been convicted of burglary and breaking and entering. The befriended each other while in prison and became lovers. Barry was gay and Mack became a bisexual during their time in the same cell. Mack a... Read full Story
shemale lover 2012-09-30 5,960 anal Cumshot Ladyboy oral
96%
New Job, New Life as as Sissy Slut
I was nearing my thirtieth birthday and times were getting tough financially. I had gotten laid off from my job and was collecting unemployment and doing some part-time work helping out friends with odd jobs. One of them suggested that I look into cleaning houses. I've always been very neat and peop... Read full Story
shemale lover 2012-12-23 9,567 sucking Uniform domination swallowing spanking
96%
New Job, New Life as as Sissy Slut Chapter 2
I was left lying on the floor, my face completely covered in cum. I was wearing lingerie and a dog collar and I had just been fucked long and hard by my "boss." My virginity had been forcefully taken. The thing is that I loved it. I loved being manhandled by this muscular man and I really ... Read full Story
shemale lover 2012-12-23 7,439 Cumshot Uniform Lingerie ass fucking domination
85%
Fucked by indonesian ladyboys
this is a true story of what actually happened to me in bali When i was 17 i was on holiday in bali, indonesia. i'd only had sex once prior, with a genetic girl, and i barely managed to get hard and wasn't able to cum so i knew pussy wasn't for me. i had been clubbing several tim... Read full Story
shemale lover 2014-09-17 61,181 suck Bareback Asian Ladyboy ass fucking
80%
The Grass Ain't Always Greener...
Lawn care takes an unexpected voyeurism and exhibitionism masturbation detour I cut grass, mow lawns, manicure shrubs, trim bushes, and plant trees. Right handed and always trimming from the right side, I've never been a switch hitter when using my hedge trimmer, if you know what I mean. Always ... Read full Story
shemale lover 2013-01-16 5,021 Masturbation Blowjob blonde jerking big boobs
83%
My Life as a Shemale Part9
It is now almost a year later and I am a year older, my hormone treatment has been going on for some time. The short version of the past few months seems some of the most poignant in my life but not conducive to this readership. My skin was getting softer, my body hair lighter and most important to ... Read full Story
shemale lover 2015-02-27 3,577 tranny Cumshot Masturbation anus
69%
TS Fiorella in Frankfurt
Recently I was visiting Germany for a conference. I was staying in the city close to the train station and checked out the red light district nearby. Walking through the red light district is an experience, on every corner and many places in between there are multi storey brothels where you can wan... Read full Story
xanykeyx 2019-10-24 11,343 Shemale Fucks Guy Ladyboy tgirls frankfurt crazy sexy
100%
sex-agenarian's onanic lust
An onanic lust of a sex-agenarian that I am; I'M IN BIG HEAT; it's the season of bodily reunions in nature... I'm like an elephant(e) waiting to be satisfied. My cloaca is starting to titillate at the mere sight (look hah!) of a guy's swollen crotch on the street... I activated all my sensors to sa... Read full Story
hippocampus_171 2024-03-09 4,198 anal solo Amateur Masturbation Creampie Sex Toys Mature small cock
100%
Sex Ed Chapter Two
Over another drink, I learnt how David Lawrence had been dressing up as a girl since he was a teenager, always keeping it secret from his family and what few friends he'd had. He was shy around women and sex and had never had a girlfriend, instead he'd buried himself in his studies and dressing as a... Read full Story
shemale lover 2016-03-10 4,906 first time cum fingering
100%
Eve Quest Part 3
Sometime during the night I was released. That exquisite pain at the point my limbs were release must have dulled my recollection of the events. I'm reasonably sure I was given the Toilet command and I hope I did a good job. In any event, I was still on the bathroom floor when I heard my mistresses ... Read full Story
shemale lover 2012-04-21 4,427 transformation oral sex cum swallowing
100%
Digging for Home
Never Make the Last Out at Third After some minutes, Charlie broke the embrace. Backing away a step, she steered her moist brown eyes into Frank's damp grey ones. "What now?" The man tilted his head to one side and shrugged. "I'm not sure. It hasn't been a day yet since you went... Read full Story
shemale lover 2012-08-25 4,697 sucking cum facefucking
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 6,584 Cumshot Fetish oral sex cum swallowing
100%
Amy's Surprise
We had been going to a local restaurant several times a week for a few months. It seemed that almost every time we had the same waitress. We soon found out that her name was Amy. She was thirty something, very pretty, even sexy all while wearing her uniform and very little makeup. She had fairly sho... Read full Story
shemale lover 2012-11-01 4,765 Blowjob cum oral sex
75%
Flowers in the Heart
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 10,441 anal tranny Cumshot oral
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 10,596 Masturbation Blowjob blonde ass fucking big boobs
68%
Next time fucking her cross dressing husband and bred his wife
Wachenheim dressed up in a pretty skirt and loose blouse with his wife watching walked up to and knelt between my legs. He sucked my thick long black cock. His wife watched and masturbated as he worked my cock deep in his mouth. She knew as soon as I did him that she ws next. It was her wishes for t... Read full Story
Rocky Wachenheim 2014-09-23 4,469 Crossdresser suck Masturbation Big Cock cd
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 8,702 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
66%
Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
ASSEaster5678 2019-01-25 12,198 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,248 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
66%
Can it get better than this?
I had to be in her area, so I set up another exceptional round with my TS ladyfriend on Friday. We smoked a joint (I usually don't) which made everything dreamlike, surreal. She is so feminine - hairless, tight skin (yoga) petite, but with this thick button cock I simply love sucking on. Can't get e... Read full Story
Action69 2023-04-06 4,899 Cumshot Creampie Ladyboy
0%
Cruising for Cock!
Cruising for Cock. Not my Story But very hot for you all. A few years back now I took a drive to a dogging & cruising hot spot in the Haldon Hill Forest on the A38 in sunny Devon. I'd been once b4 with a trucker who picked me up hitchhiking. (That's another story) WOW his cock was huge 8.5" @ lea... Read full Story
Streethawk75 2023-04-18 4,210 Stockings Crossdresser Amateur Cumshot Outdoor Masturbation
100%
Mistress Jasmine made me a slave forever
I should have been honest. I mean I should have known that lies have short legs and now they had caught up with me. The worst was I had not only lost my place in my bed but had also lost my place with my wife. Somebody else occupied these places now. Let me tell you how everything went. More ... Read full Story
shemale lover 2011-11-26 11,439 Big Cock orgasm domination
85%
Unexpected Secret
My neighbor and I get together almost every day after my husband goes to work. We have become very good friends. We go shopping, watch soaps, play cards, and cook together, all kinds of stuff. Her name is Linda. She recently revealed to me that she has a secret and isn't all that she appears to be. ... Read full Story
shemale lover 2012-02-10 4,904 cum oral handjob
100%
A Job in the Theatre Chapter 14
Sarah and Paula shared at drink as they tried to decide what to wear for their date. "Every good outfit starts with lingerie. What do you think of these?" Paula asked holding up a pair of baby blue panties. "Nice. But I really think these will be better" Sarah said holding up ... Read full Story
shemale lover 2012-03-14 2,643 sucking shemale kissing
76%
Open Wide
"Turn your head slightly to the right," she told me. I turned and my face bumped up against her left breast. "Oops, don't you bite that now," she said. "I wouldn't do that," I replied. "You better not 'cause you'd make a hole and I'd fly backward ar... Read full Story
shemale lover 2012-09-01 10,383 Cumshot Blowjob Big Cock Uniform cum swallowing
100%
Roberta, Molly and Ed
Friday "Commander Cromartie?" Lt. Commander Edward Cromartie, USN, turned toward the voice that had spoken his name. He saw two female naval officers, a tall willowy light-skin Black woman, and a short Asian one. The Black one was wearing the uniform of a full commander, the Asian of... Read full Story
shemale lover 2012-09-04 5,355 Cumshot threesome Blowjob Big Cock condom sex
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 6,284 sucking oral sex facefucking
80%
Me and 2 black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider my self a crossdresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine ladyboy. I have been taking also hormones for 4 years, on and off and I already saw many changes&he... Read full Story
shemale lover 2013-06-22 5,604 Cumshot suck Ladyboy Guy Fucks Shemale Interracial swallowing
92%
Thai delight
A few years ago I was sent out to Thailand for a week by my boss to do some checks on our operations at Laem Chabang in Thailand, about 10km north of Pattaya. Our expat manager, Dave, lived locally and instead of having to stay in a hotel he offered me a bed in his bungalow. He lived on a small g... Read full Story
shemale lover 2014-01-23 7,118 suck Asian Ladyboy oral sex cum swallowing 69
100%
Little cock convention
They came from all over the nation to downtown LA convention center. It was the "Little Cock Convention" I watched as men from all races and status came in. Sometimes they came with their wives,friends,Mistresses,lovers, or even their boyfriends. I was on Guard duty and walking the conven... Read full Story
shemale lover 2014-07-07 7,020 shemales hardcore sex humor
60%
The Clinic
I got out of my cab and looked up at the Clinic. It was a small, nondescript hospital. I was still pretty nervous about this treatment since I wasn't even sure of the details. But it was either this or go under the knife. This problem had to be dealt with. I picked up my bag and went into the lobby.... Read full Story
shemale lover 2012-05-02 5,910 Cumshot Big Cock jerking off oral sex cum swallowing
100%
Exotic Escapades Chapter 3
The smell of wood and coffee filled the quiet house as Tammy slowly picked herself up from a plush couch. Daggers of sunlight blinded her eyes as she eventually got on her two feet. Her body ached, and she noticed a small pink bandage on her left leg. The terror and pain of last night shook her as s... Read full Story
shemale lover 2012-05-05 3,028 tranny Creampie Big Cock Ladyboy fingering oral sex
100%
Casino Girl
I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... Read full Story
Jon Paul 2022-01-03 2,927 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
89%
How I Became a Girl
My name is now Stephanie, once it was Stephen. I would like to relate how I was turned into a girl (really a transvestite slave) by the beautiful young lady who has become my mistress. I have always felt that I should have been born a female. I definitely have female traits. I have a very feminine... Read full Story
shemale lover 2018-12-30 13,714 Masturbation pussy little cock
66%
Cock Sucking Jail Whore
I've always known that I was not meant to be a guy. Being sexual curious I would look at porn mags like any one does. At first it was just magazines with pictures of naked woment. It was when I ran across my first Hustler magazine that my life was changed forever. Seeing pictures of studly guys with... Read full Story
shemale lover 2011-09-17 4,452 Cumshot asshole oral sex
87%
The Hotel Part 1
I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days. Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, fucked fem, huge dildos, and giant buttplugs are just a few of my fetishe... Read full Story
shemale lover 2012-02-11 6,073 Fetish cum domination Sex Toys
50%
Sandy TS
The first part of this story is true. Having found myself on an online dating service, I was only looking for women to meet. Little did I realise that would include a lovely Pre-op, called Sandy TS. After seeing the photos, I was captivated and started to dream about her.......I hope that you will a... Read full Story
shemale lover 2012-09-04 3,374 Cumshot Masturbation Blowjob tits licking
100%
Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... Read full Story
shemale lover 2013-01-04 10,191 sucking Fetish Uniform domination big boobs
77%
Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
Regina10 2020-09-16 5,444 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
88%
Trip to Portimão
It is about a 3 hour drive depending on traffic to the Tivoli Marina Portimão in the Algarve from where I was staying at the Hotel Mundial. Oliva came to pick me up. She had one of those Toyota SUV things. I put my bag in the car and I noticed Olivia had rather a collection of luggage. I smiled to m... Read full Story
Rusty12 2020-09-18 4,090 Amateur Cumshot Masturbation Shemale Fucks Guy Blowjob domination old-and-young
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 5,326 Cumshot Outdoor Latina Bareback threesome Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth double anal
75%
Virginia’s Luxurious Evening
West Palm Beach didn’t have many cold snaps, but when one did rake the city the weather seemed twice as frigid as it actually was. Virginia Stanton sat alone in her office on the third floor of Prism Design’s building overlooking the Intra-coastal Waterway. She had been chilly all day, m... Read full Story
shemale lover 2017-07-16 10,997 tranny Big Cock fingering
100%
Alpha Gamma's Secret Part 2
-4- Molly awoke to the annoying sound of her alarm beeping. Groggily, she reached over to her night table and turned it off. It was 7:00 AM, way too early for a 19-year-old college girl to be awake, in her opinion. As she stirred, her girlfriend wiggled up against her, eager for body heat. ... Read full Story
shemale lover 2011-11-02 3,430 anal sex Masturbation shemale
100%
Tony to Tanya Part 2
Tony woke up on Saturday morning feeling excited without knowing exactly why. He tried to sit up, but his left arm was pinned down by Sarah's body. This was normal for a Saturday morning, since she tended to sleep at Tony's house on Fridays. The reason he was excited suddenly hit him. On Tuesday,... Read full Story
shemale lover 2011-12-19 3,155 sucking transsexual cum swallowing
50%
Devastating and dominating
Tracy drove the black SUV with her friend Miss K in the passenger side, both of them struggling not to be bored to sleep with the monotonous countryside I-64, the scenery broken up only by the occasional road sign or truck stop. The Madonna CD thumping in the stereo helped matters though, the t... Read full Story
shemale lover 2012-01-29 5,117 Masturbation sucking Creampie Latex fucking
100%
A New Me...
Flash back 10 years when I had just turned 18 years old and had just been accepted into the University of Vermont. I was ecstatic because this was my reach school (I wasn't all that smart book wise) and it was the school that my sister Elizabeth (20, a junior) was already attending. My sister and... Read full Story
shemale lover 2012-04-14 5,290 Masturbation Fetish crossdressing
100%
The Trip Part 2
I awoke suddenly feeling dazed and with my head pounding. "Kara, baby...you okay?" asked Chris Chris roused from his slumber and reached for me. I was sitting up, breathing hard. "It was nothing. Just a dream, I guess."

 "Okay. If you say so." He rolled ove... Read full Story
shemale lover 2012-05-20 2,190 anal sex oral sex cum swallowing
71%
A Schoolgirl's First Time
I’d been emailing and phoning Dan for several weeks when he first suggested that we meet up. It was very exciting and I couldn’t wait. My every waking hour was spent thinking about it. The only odd thing was the request he’d made. “Can I ask you a bit of a kinky favour?&rd... Read full Story
shemale lover 2012-06-10 4,364 Cumshot Fetish Uniform oral sex crossdressing
66%
Your Waitresses
You begin your evening by taking a long luxurious bubble bath followed by taking the time to apply your makeup at a beautiful white makeup table and mirror from the 1920's. You then slide a sheer pair of black stockings up each leg and attach them to your black and red lace garter belt. You then run... Read full Story
shemale lover 2012-08-10 3,747 Fetish cum crossdressing
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 3,845 anal Cumshot Masturbation Sex Toys
88%
Very Impatient on a sex fanstay
Are you ready for this Mish?" "Not really but it's too late to back out now." I stood in a dark alley before a metal door shaking with both anxiety and the cold, waiting for the door slot to open and for the night to begin. I wouldn't admit it to my friend Simone but secretly I hoped we would ... Read full Story
ASSEaster5678 2018-07-10 10,770 Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale Mature