Sort by
Relevancy

Free Stories

90%
How I became a cute femboy CD part 4
My legs finally started to work again and I turned and was about to walk to my bedroom when Kevin’s voice stopped me. “Come on, Natalie, you know you want to. You have been crushing on David ever since he moved here.” “You’re an asshole, Kevin. You know that. You are a total asshole! I tho... Read full Story
Cute_Femboy 2016-04-05 12,440 first time cumming crossdressing cd sissy cumshot in mouth
100%
The Girl Next Door Ch. 02
derezzed Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the s... Read full Story
Gwapo67 2022-05-13 5,281 Bareback Creampie Guy Fucks Shemale cum in mouth
0%
The Greatest Lie Part 19
The booked me as Alex Rios and handed me an orange jump suit and slip-on boots. I changed in a tiny curtained alcove and relinquished my clothes, shoes and purse, and became Inmate 265743. The booking clerk ignored my pleading eyes, so I begged. "You can't put me into a male population. I... Read full Story
shemale lover 2012-01-21 4,802 hardcore femdom erotic encounters
50%
A Fantasy - Part 3
Sharon put her cell phone back into her purse, turned to Paula and I and said "I'll be right back, with the Chinese food!", gave us a wink and took out her wallet, grabbed some money and then went off to get our dinner. Paula was sitting on the floor, she leaned back on her left elbow and started... Read full Story
swollenrooster 2023-09-20 5,275 Group Sex Cumshot Shemale Fucks Guy Fetish gangbang Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
50%
The Greatest Lie Part 15
I think that if you could get honest answers, a lot of heterosexual guys would probably admit to having had at least a passing desire to be a girl. If they were honest, they would probably admit they thought of it "when I first noticed a girl's breasts" or "when I first felt a girl or... Read full Story
shemale lover 2012-01-20 6,192 anal hardcore erotic encounters fantastic
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 6,547 sucking cum massage
100%
A Fantasy - Part 2
Paula begins to grown, ohhing and ahhing. I suck hard and swirl my tongue around on the head of her cock. Sharon has pushed her dildo all the way into my ass and begins to pump my ass with a slow, steady rhythm. Paula holds my head in place and begins to thrust her cock into my mouth harder. "I'm go... Read full Story
swollenrooster 2023-09-20 5,025 Group Sex Cumshot Shemale Fucks Guy Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
50%
The Greatest Lie Part 17
They say that life is about making choices. But we humans don't get to choose the two most important factors in our lives. We don't get to choose our genes, so I got stuck with XY chromosomes. And we don't get to choose our natal families, so I got stuck with my mother and father. My father, Edua... Read full Story
shemale lover 2012-01-20 4,502 erotic encounters fantastic consensual
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 9,085 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
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 9,460 shemales Group Sex interracial sex
100%
Witch Chronicles
I have been asked to write down my perception of the events of the war. After what's just happened, I thought it best to wait and rest before writing things out, but the big wigs want me to get it all down while it's still fresh, so don't expect this to be an extremely military report. I... Read full Story
shemale lover 2012-01-01 5,840 Masturbation orgasm fantasy tg
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 16,594 shemales Masturbation Fetish
66%
Debbie Part 10
Debbie might have lived out the rest of her life if it hadn't been for some events, which started back at Mistress' mansion. Several years after selling Debbie, Mistress Helen Chamberlain still ran her ruthless slaving operation. Giselle was still her favorite slave, constantly restrained and regula... Read full Story
shemale lover 2011-12-23 4,958 transgender toys bondage and discipline heavy
100%
The Greatest Lie Part 4
Don’t get me wrong, I don’t hate being around people. Actually, I hate being alone: it brings out the weird self-critic inside me. But god, do I hate crowds. Fall registration brought mobs to the campus. The half-empty dormitory that I had shared with a few Asian engineering students was... Read full Story
shemale lover 2012-01-19 4,694 taboo femdom crossdressing
83%
Elaine & Me
- Chapter One – Our First Meeting - I had two weeks to go before the final degree exams and I was working hard. Perhaps too hard, because I desperately needed a break from the hours and hours of revision. It felt like I just couldn't take in any more detail about Quantum Mechanics or Solid ... Read full Story
shemale lover 2012-03-31 11,377 sucking Fetish transsexual
83%
House Hunting Chrissie
When I casually mentioned to one of clients during a session that I was toying with the idea of perhaps buying a house and renting out my condo he needlessly took the time to remind that he owned one of the largest realty offices in town. It must a salesman thing, not being able to leave business ... Read full Story
shemale lover 2012-07-01 3,189 anal oral sex humor
0%
Black Transsexual Nation
Big black transsexual women are truly beautiful. And the big and sexy bisexual and heterosexual men who love us are truly wonderful. I ought to know, I'm one of these magnificent black transsexual ladies. My name is Amanda Joan Baxter, friends call me A.J. I'm a big and tall, big-breasted, wide-hipp... Read full Story
shemale lover 2012-07-06 4,467 tranny Group Sex cum Ebony oral sex
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 3,908 big dick shemale oral sex crossdressing
75%
Old Folks Part 2
It had been eleven months since that day when I arrived at Honey and Frank's house. It was about 1am at night as I stood in a quiet street waiting for Frank to pick me up. I had just finished with my last client for the night a good blowjob with him ending up cumming on my face. I was touching up my... Read full Story
shemale lover 2012-01-10 6,858 transsexuals erotica romance crossdressers
100%
Angel Chapter 3
On Monday morning, Angel Jones reported for her first day of work at the main office of the big London Bank. As she sat on a chair in the anteroom of the personnel office, she thought about what she would be doing there. It was almost a certainty that nobody in the bank knew she was a T-girl, becaus... Read full Story
shemale lover 2012-12-01 4,868 Cumshot sucking jerking
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 4,610 torture toys bondage and discipline chastity belt
100%
Debbie Part 2
There were no clocks and no windows in the dungeon, so Debbie (as she thought of herself after a long night of pain, lust and confused thoughts) couldn't really tell that it was morning. But she assumed it was morning when Mistress came back. Debbie's walk was still perfect even after walking around... Read full Story
shemale lover 2011-12-22 5,217 transgender toys bondage and discipline heavy
75%
Blue collar Master, white collar slave Part 2
About an hour later I was once again naked except for my chastity pouch and my stilettos and once again I was screaming and crying, my body covered with angry red welts from Master Darren's whip. On my knees crying and begging I held his cock in my hands, trying to give the best handjob ... Read full Story
shemale lover 2012-01-13 11,322 torture extreme fiction bondage and discipline
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 6,035 cum transsexual fantastic
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 10,420 anal tranny Cumshot oral
100%
Tight Spot
XtinaSmith2017 Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavor but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way ... Read full Story
Gwapo67 2022-07-22 5,842 Big Tits Bareback Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
50%
Sissies Training Part 2
I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by ... Read full Story
shemale lover 2011-09-17 6,552 shemales Fetish bdsm
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 4,646 Group Sex Masturbation shemale oral
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 30,925 strapon porn
100%
Fantasy Reversal Chapter 7
As this was to be my final day and night as Katrina I awoke early. Sam was still in bed as I pulled my hair back into a pony tail and dressed in my running shorts and sports bra, I stopped a moment to admire how I looked. My hands roving my own girlish body, gently feeling my curves. Finding, to my ... Read full Story
shemale lover 2012-06-30 2,690 Fetish Blowjob oral sex crossdressing
50%
Why, She's A "He"!
Tina had mentioned to Dave a bar she’d heard about that catered to certain sorts of sexual adventurers and suggested she and Dave visit one night to check out the scene. A friend had described it to her and said she occasionally liked to go there with her husband. These two were old fashioned ... Read full Story
shemale lover 2012-10-26 4,624 anal tranny oral rimming handjob
100%
Who's The Sissy Now?
Like many people, I was bullied in school. I was small, slender and effeminate and, as a result, was often called gay, queer, fag and sissy by school bullies. The fact that what they said was sort of true just made it closer to the bone and more painful to hear. Like many teenage boys, I was going t... Read full Story
shemale lover 2012-11-14 6,967 shemale facial oral sex
90%
DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
CD DIXIE IN NH 2016-05-10 10,209 Big Cock cumming sperm ebony cock
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 30,338 Teen (18+)
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 10,336 shemales gay male interracial sex
100%
A Different Kind of Woman Part 2
My hands were at one and eleven o'clock tied to the bed, the beautiful creature that I was so infatuated with turned out to be a shemale and I was at her/his mercy. Tiffany was working her/his penis up my butt with precision all the while stroking my penis keeping me rigid hard. Each time I thought ... Read full Story
shemale lover 2011-10-11 2,459 anal shemales Group Sex
87%
Headmistress' Favorite Sport Part 3
There was no more time for Denise and Susanna to get over their chemically induced bout of incestuous activity as Denise was being sent to school. This was of course part of the plan. Slaves should always feel guilty about something and once their slave training was over, neither would be able to ma... Read full Story
shemale lover 2011-12-12 6,247 toys bondage and discipline chastity belt
100%
The best of two Worlds Part 4
After our adventure on the beach Jacqui had a moral and physical hangover for a few days. She would do things to me that went beyond my expectation. She was absolutely fascinated with my cock, giving me head jobs the moment I walked in to the door. Upon my arrival home I would find her half naked, h... Read full Story
shemale lover 2012-04-26 2,601 anal sex Group Sex Blowjob orgasm
100%
Don't Avoid Daddy
It feels like I haven't been used in ages. I'm too much of a scared sissy. I find guys from all over, talk, email, text sometimes. But when it really comes down to it I get too scared. I've been with this guy before, his cock is soda can thick and he's really rough. The day after my first encounter ... Read full Story
shemale lover 2012-10-23 5,824 Cumshot oral sex deepthroating
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 10,984 Fetish crossdressing feminization
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,456 Big Tits Cumshot Masturbation Uniform Frottage
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 6,985 shemales hardcore sex humor
75%
Something For Everyone Part 2
Josh was the first of the three to wake up. He left the two women in bed and took a long hot shower. The water felt good as it cascaded over his body, and he soon found himself wondering what was going to happen next. The sex had been fantastic, but it wasn't what he had been expecting. He finally d... Read full Story
shemale lover 2011-10-20 2,745 fingering oral sex stroking handjob
50%
Trying It On For Size
I was twenty minutes early for my one o'clock appointment so I found a shady spot in the parking lot of the upscale chain motel, kept the engine running to power the air-conditioner on the warm Sunday afternoon, took a few deep breaths and tried to relax. My mind wondered back over the series of eve... Read full Story
shemale lover 2011-10-26 7,892 asshole licking sucking
50%
Magician's Assistant - Friends & Lovers Part 10
Magician's Assistant - Friends & Lovers takes place in the Magatrix the Magnificent Universe, which was first introduced in my serialized seven-part story, Magician's Assistant. The premise upon which both that story and this story are based revolves around the fact that Magatrix the Magnificent... Read full Story
shemale lover 2011-12-26 4,002 anal erotic encounters erotic
100%
Emily and Steve Part 9
Over the next few weeks things really started to settle in at work. Emily was being more than accepted, she was being lauded. Emily, feeling much more comfortable as a woman, started being a much better worker. The quality of work that Emily was producing was far superior to Mike's work. She was fea... Read full Story
shemale lover 2012-04-07 2,819 anal sex Group Sex blonde oral sex
100%
Dottie's Back
Four weeks had passed since my first blowjob party. In that time, I had become obsessed with getting implants. The concept of being tit-fucked and wearing deep-cut tops without being concerned about the distinct line between my flesh and the fake boobs had become a constant fantasy of mine. After be... Read full Story
shemale lover 2012-11-02 3,842 Group Sex Cumshot facial oral sex
81%
Bimbo Barbiex
Ooh hiya boys, I'm Barbie Leigh, a naughty little bimbo tranny, 19 yr old, 5'7" tall, blond, blue eyes, slim and tanned with a hot curvy ass. I have been dressing as Barbie since I was probs about 16 and I'm very well versed when it comes to horny guys and how to please them.lolz... Read full Story
Barbie Leigh 2013-12-08 4,326 tranny ass Teen (18+) sucking rimming
100%
Hung Shemale has Motorcycle Trouble near Vegas
I drive down a deserted two- lane highway outside of Las Vegas, Nevada. It is August and the temperature is well over 100 degrees. In the distance, I see a tall beautiful mature creature that walks alongside the road. As I pull over, I am stunned by her powerful physique. She sports an incredibly ti... Read full Story
darrell 2024-02-02 5,414 Shemale Fucks Guy Blowjob blonde Big Cock Mature deepthroat cum in mouth toe sucking Fisting Anal
77%
A Night i will Remember 4 Ever
About six months ago I went to a transvestite bar and dance club in the centre of the city where I live. I was dressed in my sexiest all-leather shift minidress, sheer stockings and 4-inch stilettos, and my favourite blonde wig. I was fully made up with long false eyelashes and blue shadow, painted ... Read full Story
bigtranslover 2013-12-19 7,509 anal shemales Group Sex
94%
Ann
Ann was the woman who gave away free samples in the supermarket where I was manager, and as often as we could, the employees could find us sitting in my office, smoking, laughing and talking. Ann had a way of smoking a cigarette that drove me insane with sexual desire. Inhaling, her lips were pucker... Read full Story
shemale lover 2014-10-27 6,674 shemale fondling
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 4,281 anal sex Group Sex cum Latex
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 4,999 first time femdom crossdressing
100%
My last and favorite
it was 3 years ago .. id become close friends with a girl who had so many friends but she had trouble getting guy friends and when she did get boyfriends it never lasted long and i felt so bad for her. one night we were drinking and went to her house. i loved her and treated her like my s****r, but ... Read full Story
shemale lover 2012-01-23 2,424 shemales Group Sex lesbian sex
100%
SheMale Pussy and Cock
I once had a friend who always said "never fuck anything you can't bench-press". He was right, the biggest benefit of having sex with someone smaller and lighter than you is you can lift them easily ! On a recent trip to Thailand I couldn't take my eye's off a stunning, short, tiny but ... Read full Story
shemale lover 2012-01-24 4,222 anal shemales gay male
75%
Backsliding: Tim's Story
Every man has a weakness, but not everyman knows what that weakness is until it is too late. The story I'm about to tell is something I'm not entirely proud of. My name is Tim. I'm a 22-year-old college student at California State University. I'm almost at the end of my senior year studying to be... Read full Story
shemale lover 2012-02-09 4,926 sucking fingering Guy Fucks Shemale