Sort by
Relevancy

Free Stories

71%
A Shemale Christmas Carol
I got a job working as a mall Santa at the local mall during the Christmas shopping season one year. It had been a real shitty year for me. My wife of almost twenty years left me for a younger man, I lost my other job due to layoffs and, on top of all that, my doctor diagnosed me with high blood pre... Read full Story
shemale lover 2011-08-28 4,537 asshole sucking Big Cock
66%
Charisma & Tiffany Part 2
Tiffany's six cocks filled Charisma's six cunts and, although the sorceress was on top and, therefore, able to move faster and with more force and agility than the supine shemale, Tiffany, nevertheless, felt overwhelmed by the welter of sensations that had, as it were, laid siege to her consciousnes... Read full Story
shemale lover 2011-09-02 3,000 asshole shemale domination
100%
Charisma Part 2
After fondling her breasts and her cock and balls for several more minutes while she probed Tiffany's mouth with her tongue, Charisma allowed her guest to get undressed while she removed her own clothes. The seamstress was a beautiful woman, for a genetic female, but, of course, she was nowhere n... Read full Story
shemale lover 2011-09-03 3,048 anal Big Tits Cumshot
100%
My First Time Out Part 6
Preface: It is not imperative, but helpful that you read Chapters 1-5 in order to grasp the personalities of characters in this story. WARNING: The following story contains some explicit foul language and IS NOT for reading pleasure for anyone under the age of 18; nor is it permissible to read if... Read full Story
shemale lover 2011-10-18 2,969 shemale dick skinny
100%
Deal or No Deal
Tina and Gary have a marriage that worked wonderfully because they always checked with each other before doing anything important, and because each got what they wanted by making deals with the other. Deals about vacation - she chose the beach this year because he chose the mountains last year. Deal... Read full Story
shemale lover 2011-11-06 3,940 Big Tits shemale fantasy
82%
My first blowjob
I met a shemale online called melisa and we had been talking over msn for afew days, mainly having saucy chats about sex and getting off. She asked me to meet her on the coming weekend which excited me as i was a virgin to cock. We arranged to meet in a bar that was a stone's throw away from my f... Read full Story
shemale lover 2012-06-06 13,469 first time Cumshot Blowjob shemale cum swallowing
100%
Danielle Works a Saturday
It had been a few months since his wife left him. Well "ex-wife" as the divorce had been recently finalized. It was her choice; she walked out on *him*. She said she got tired of "Danielle", even though she was entirely responsible for Danielle's "birth" to begin with. ... Read full Story
shemale lover 2012-06-18 5,656 anal sex Creampie oral sex cum swallowing
93%
SHEMALE SEX IS THE BEST
I had been in sex with gays for 1 year, but had always been intrigued by those hot looking chicks who packed more than a pussy between their legs. I had no idea where to find one in Kanpur I was definitely bi-sexual, still seeing whores, and still going to gloryholes for my cocksucking needs. I w... Read full Story
shemale lover 2014-03-07 4,724 tranny Big Cock ass licking doggy style big boobs rimming
92%
My Life as a Shemale Part2
Many things happened over the next few months, for one, I healed maybe better than I ever was, I discovered that there was another side to me and most important I met Tim. He was the one that found me and maybe even saved me. A middle aged man who once had a daughter, I know that because I am now li... Read full Story
shemale lover 2015-02-19 3,962 tranny suck Blowjob shemale swallowing
91%
My Life as a Shemale Part6
It was the night before my first day of school, I was excited. Sam was over and we were chatting away, she was really becoming a good friend. I told her about what had happened with Mike the week before and she listened to the whole story. She asked me how I had felt about it and I kind of laughed, ... Read full Story
shemale lover 2015-02-25 3,098 anal ass sex toy shemale anus
71%
Alleyway Adventure
I was on my way home from school and this girl in those tight yoga pants and a shirt that showed off her huge boobs taps me on the shoulder as I walk past her. "Want to have some fun?" She asked smiling. Nodding I said "Yes I would love to." Taking my hand she lead me down the st... Read full Story
HornyCummer2344 2017-09-12 4,315 Big Tits Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale
100%
Threesome fun
We had invited friend over who has big cock --he arrived and we sat around for awhile talking about sexual encounters of the past --I'm a bi part time shemale cross dresser who is very kinky --anyway it got around to looking around the house and as it happened we stopped in the bedroom , and all o... Read full Story
goodgurl34 2019-01-08 4,424 Stockings Crossdresser Amateur Big Tits threesome Blowjob Big Cock Lingerie domination Guy Fucks Shemale Mature Homemade threesome sex
100%
My 1st Time was Not the Only Time.
One late night after hitting the slopes and partying I left my friends birthday party feeling extra horny. It was about 6 or 7 in the morning now and after having no luck finding an escort I responded to an ad on craigslist posted by a trans woman. I figured two things, this dick isn't going to suck... Read full Story
LesFuax 2019-02-16 9,131 first time Small Tits Amateur Latina Bareback Creampie threesome Blowjob Big Cock ass fucking barebacking barebackedshemales first time with a tranny raw anal raw dick raw fucking firsttime
85%
My Knight
I felt good as a looked around the club and watch the Queens on stage perform their acts. I felt like I belonged here among this faction of society. Drag queens and Trannies were my people and the only thing I regret is being in the closet and not having the courage to do it more openly. However i d... Read full Story
Regina10 2020-06-23 3,839 Bareback Guy Fucks Shemale Ass to Mouth shemale + shemale
100%
Jennifer
WhiskeyIsGood I woke with a start, startled by a loud banging sound from downstairs. The floor shook from the vibrations, causing me to sit upright in my bed and glance towards my bedroom door. What in the hell, was going on down there? My question was quickly answered, by another loud bang, foll... Read full Story
Gwapo67 2022-09-13 6,024 Big Tits Bareback Shemale Fucks Guy Blowjob blonde Big Cock
100%
Becoming Kacey
I indulged my crossdressing opportunities as often as I could, but as time went on, the chances grew further and further apart. Although I couldn't play dress up in my alone time, the fantasies never seemed to cease. When I entered high school, I dated girls and enjoyed the young passions that teena... Read full Story
KaceyKlarissa 2024-01-16 4,058 first time Crossdresser Amateur Homemade sissy femboy shemale + shemale romantic teen (18+)
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 3,247 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
100%
Fake plastic bimbo barbie famally in public part 1
My name is lana foxx,i am a fake plastic bimbo barbie shemale whore. I grew up in a whore house with my stepfsister candy,because my mom was a whore then and here job was an escort whore. from a young age, me and candy were interested in naked men, women and sex!! We allways walked in the room wh... Read full Story
Duckfaceslut 2024-05-07 2,229 shemale whore slut Plastic lanafoxx
100%
The switch
HI have been married for 12 years now. Trim and dapper, this 35-year-old's marriage was satisfactory enough and I played the role of husband well. Sex with the wife was still good, with both making out at least once a week or on rare occasions, once monthly. Twelve years on in this heterosexual rela... Read full Story
shemale lover 2014-10-11 8,407 anal shemale jerk off
92%
All The Transexual Stories Came To Life
I’ve spent my adolescent years reading the transexual stories whenever I could. I had a long process of self analysis trying to figure out if I were gay or not, so I wanted to find a shemale who could be my first and see if I even like being fucked or sucking a dick. Thanks to the sex personal... Read full Story
shemale lover 2016-02-12 5,990 suck shemale ass licking
100%
Charisma Part 1
Tiffany De Vine wondered whether the ladies’ dressing room in which she was about to try on a brassiere was under surveillance by some fat, obese fucker with a day’s stubble of beard and a cum-stained crotch. Probably, she thought; it would be just her luck. Well, if some slob was drooli... Read full Story
shemale lover 2011-09-03 3,595 Big Tits shemale Lingerie
50%
Puzzle
Women. There's no figuring them. They're a puzzle, one of life's mysteries, and that's a fact. Who knows what goes on in their brains, or whether they even have brains? I mean, what rational creature would get excited over Valentine's Day? Could any holiday be more obtuse? Like your bitch, mine's... Read full Story
shemale lover 2011-09-05 3,087 Big Tits asshole scrotum
80%
Femme Fatale
Derek sighed heavily, his eyes scanning the bank of security monitors, each of which showed a different view of Femme Fatale. A month ago, he'd taken the job as a security guard for the woman's clothing store because he needed the money and because he supposed that watching the store - or, more spec... Read full Story
shemale lover 2011-11-18 3,317 hardcore cum shemale sex
50%
Interview with a Fluffer
. "Clarissa", I want to thank you for agreeing to do this interview with me. I think a lot of my readers will be very curious to hear about your experiences in the industry. First of all, can you describe what is involved in your job for me? A. Hi Leah, first of all, no problem, I... Read full Story
shemale lover 2012-01-30 5,425 sucking cum fucking
66%
First Time With a Shemale Part 2
"WOW" I thought to myself "I'm gonna fuck a hot Asian hooker for free!"...She took out my cock and started playing with it, "I love your cock babe,mmm I want it in my mouth" and she slowly started sucking on it. Now back in the days I wasn't much of an expert, but that ... Read full Story
shemale lover 2012-02-17 3,153 first time Asian fingering
100%
I've always wanted to meet a gurl!
First of all I would like to apologize for my English. Hello there! I live in a small country's biggest city and here people are strange. If they are crossdressers, shemales, trannies, tgirls, gurls (actually we have only 2 words for a shemale, so I don't know which one is NOT offending please excu... Read full Story
shemale lover 2012-03-30 2,567 Small Tits anal sex oral sex cum swallowing
100%
The new girl in town
It all started when i was a teenager. I was like every teenage boy, i looked at porn on the internet and masturbated a lot. i love to watch lesbian porn it was sooo hot watching to girl have sex. i soon after that i got into the anal sex, watching the girl have orgasm after orgasm while she has a hu... Read full Story
shemale lover 2012-05-06 4,688 anal sex Blowjob handjob jacking off
100%
Fantastic Weekend - First Touch
It finally worked! After a year of posting ads on Craigslist, and what I'd decided was my last attempt, I got results. It was short and to the point, "Panty Sub Seeks Oral Top." As is normally the case, I got a lot of one-line responses and picture requests, but buried in there were two gu... Read full Story
shemale lover 2012-08-31 3,313 Stockings Crossdresser Cumshot Blowjob Lingerie
94%
Adam Picks Up a Transgender
Sitting along the short L stretch of the bar, Adam admired the pretty girl sitting most the way down the longer length of the bar. Her blonde hair was long and curly. Her tight dress had a swoop front that showed plenty of cleavage. He knew the rumors. She wasn't completely a "she." She wa... Read full Story
shemale lover 2013-02-12 7,232 sucking Shemale Fucks Guy Lingerie ass fucking handjob
86%
Shemale Sherri Arrested for Theft
Sherri had had a tough night. First she was involved a little confrontation with a skinny bitch who thought that just because she had a vagina made her hotter than Sherri (and no, it didn’t), and then Sherri borrowed a bottle of whiskey from some advertising executives who called the police on... Read full Story
shemale lover 2013-06-29 5,230 tranny ass Cumshot shemale fingering domination
92%
A very special lady
I knocked at the door, unsure of what to expect. Living in a big city for the last year, where I didn't really know anybody, had certainly put a crimp in my sex life. Where I used to live, in a much smaller town, during my high school years, I'd been able to get my dick into many tight, warm and wil... Read full Story
shemale lover 2013-07-18 6,053 Stockings anal sex Shemale Fucks Guy ass licking ass fingering
91%
First Encounter
I always has a fascination for transsexuals. I remember my freshman year of college, I don't remember how I stumbled upon it, but I was the most aroused I have ever been as I watched the beautiful Mia Isabella stroke her hard cock. Something about a feminine being, with large breast, voluptuo... Read full Story
Drewbee 2014-11-07 8,842 first time Big Tits Cumshot Masturbation shemale
100%
I FIND MY ROAD IN SYGKROY
My name is Anastasia, although the real name is Nick. As you can see I'm a decent boy day, a normal relationship with girl (not so normal, but that another story!), Sociableness and not effeminate at work and generally to the outside world. But when you go home and my girl is missing, I beco... Read full Story
ANASTASIS CD CRETA 2014-12-03 3,909 first time Creampie Blowjob ass fucking 69 cd
100%
My Life as a Shemale Part3
The next year would become the strangest and the most turbulent of my life, I will have to write more chapters just to get it all in. What came next was my transformation, even though it was becoming more clear to Tim, Sam and I that I was transgender from the onset. Sam came and saw me more ofte... Read full Story
shemale lover 2015-02-19 2,746 tranny Cumshot shemale ass fucking sperm
78%
First Time Fuck with Another TS
Since I fully transitioned to a TS I've always admired to have a mutual fuck with another TS like me. TS like me were very rare in my area. I've always fucked lesbian girls who were really getting addicted to me. I really wanted to try out something new. Fortunately that moment came.v ... Read full Story
emmah 2017-11-21 10,983 Big Tits Blowjob Big Cock shemale + shemale mutual
100%
Sports Bar Pre-drink
Sitting on the chair leaning against the bar, Steven sat quietly sipping on his rum and coke. It was a fairly quiet night at the local sports bar he often ventured to after work to wind down from his work shift. Steven looked up at the door as a small group of women walked through laughing and ta... Read full Story
Master VeeJay 2019-09-27 9,425 Big Tits Blowjob Asian Guy Fucks Shemale
54%
Experience with Shemale Kadambari in Pune
PS: this is a genuine experience. Hey, I am back with another story. Let me introduce myself. I am ordinary guy who like to score shemale from Pune. I have already posted one experience with arzoo. So yes let's start, I had a normal chat with Kadambari on what's app discussing the rates. So she a... Read full Story
spidymoto 2020-03-24 6,411 Cumshot Blowjob shemale Big Cock Guy Fucks Shemale indian Indian Shemale Pune Pune Shemale
90%
Why does cock look so good on a girl ?
Horny and looking for something to jerk off on, of started surfing porn sites looking for just the right hottie. Pornstar Christie Lee really gets my juices going so I clicked on her. I started watching the video I was familiar with and knew would get me off when I decided to check out all her video... Read full Story
Verdura08 2022-10-17 6,157 Crossdresser Amateur Cumshot Big Cock ts posing huge dildo
88%
A girl from the bar!
This guy picks up a chick in the bar and takes her to a private room, the only thing on his mind is to fuck her, but there’s a surprise that the chick has prepared for him! When I stepped down to the hotel’s bar I didn’t even notice that girl at once. I sat my ass down on the so... Read full Story
shemale lover 2014-04-23 7,041 shemale ass fucking facial
86%
Giving shemale a blowjob for the first time
I've been fantasizing about a shemale cock for a long time. Get me right, I am a straight man and all, but somehow the idea of sucking a girl's dick always turned me on. I'm not a big fan of anal sex and I don't think I'd love someone's cock in my ass, I'd rather prefer to give shemale a blowjob. ... Read full Story
shemale lover 2011-07-09 12,029 licking Blowjob shemale
77%
Shemale Sex Stories Tell The Truth
You couldn’t help it but to notice when the tall blond came to the party. She was steaming hot, and all the guys turned their heads while all the girls glanced in envy. She was dressed a bit slutty and didn’t seem to mind the looks or the attention. Soon enough, she approached me and tol... Read full Story
shemale lover 2016-02-18 14,069 anal sex oral sex tgirl
71%
Choosing From Shemale Pics Gallery
"You into shemales?", asked the man in Amsterdam's Red Light district, "We have everything in De Wallen, just ask", he continued to promote his girls, "Maybe the gentleman would like to watch some shemale pics gallery before making a decision?" And I thought - why not. ... Read full Story
shemale lover 2016-06-30 10,609 anal sex Cumshot oral
90%
Night With Shana
This meeting took place in Los Angeles, CA. I’m sure many of you are into shemale porn movies and will know who Shana is. For those of you who don’t know her, she is a gorgeous white shemale with long brown/blondish hair, big tits ( think there is some silicone in there — but who... Read full Story
shemale lover 2018-01-14 11,180 tranny suck face fucking
100%
Shemale Maid
Colleen rushed through the mansion's open gate and headed towards the main door. She opened her mini leather bag and searched frantically for her keys, although she knew she was hopelessly late. Was it her third or fourth unsuccessful attempt in a row to get there on time? Or had there been more? Oh... Read full Story
shemale lover 2011-09-13 5,141 licking sucking Big Cock swallowing
100%
Sweet Sherri
"The fuck you want," the girl hissed through her teeth. Well, it's hard to say. For one, this was the one night of the week at the particular club that was tranny night. Unless the lucky woman was either a straight freak or had been exposed to the scene, there weren't too many people wa... Read full Story
shemale lover 2011-10-31 5,555 Big Tits transsexual big ass
100%
Secrets
Jon had invited me to spend another weekend at his place with another of his friends. I always find his friends to be interesting so I accepted. Jon had given me a garage door opener and a key to his home after my first visit. He met me as I parked my car in the garage. He was wearing his usual skim... Read full Story
shemale lover 2011-11-01 6,066 anal Blowjob transvestite
100%
John's Friends
Several of us had decided to meet at a friends house for a long weekend. This friend had a place on the river and a big covered patio, with a huge hot tub, a sauna, and a really nice huge shower. Our friend had his wife, sister, sister in law, and mother in law living with him. He said, "You ca... Read full Story
shemale lover 2011-11-03 2,752 anal shemale Big Cock
50%
Eden
"Hey Frank, where ya been? I need ta ask ya somethin' man." "I'm on vacation. Talk to Abbey. She's the boss until I get back. Ya better get used to it, because when I retire in a few months, she'll be taking over on a more permanent basis." "Retirement? You're only 29 years ... Read full Story
shemale lover 2011-11-25 3,654 cum oral cum swallowing
50%
She had a COCK bigger than mine ..oh my !
this is no B.S ,no fantasy, no make belief, no fairy tale,.. this is a TRUE STORY and an ACTUAL EVENT. iv always been a very observant k** growing up always trying to find the unseen and overlooked things in life i guess you can say curious....how curious ??:] well... there was this older lady... Read full Story
shemale lover 2012-03-16 46,836 sucking Big Cock ass licking swallowing
100%
Hot Trannys & Ebony Shemale Cum
I've always considered myself as a huge fan of heshe cum & porn vids. You tell me what else a man needs besides a tgirl's cock, a nice portion of shemales fucking and sucking & loads of transgender stories to tell the guys... Forget about the usual trans sexual pictures & pre-op transsex... Read full Story
shemale lover 2012-03-27 5,120 big dick blonde cum fingering huge tits
100%
Surprise!
Here I was, on a Sunday night, going in the club to have some fun. After few hours of dancing and drinking, one pretty girl came and asked me to dance with her. Looking at her I saw that she`s not a "grenade" so I was thinking maybe I will have some fun tonight so we started dancing. Afte... Read full Story
shemale lover 2012-06-27 4,100 first time Cumshot Blowjob shemale tiny cock
96%
How I Really Got My BA In College
I was living in an off-campus apartment building two months into my first semester of a two year BA program. I lived on the 22nd floor and my three friends Ray,Jim and Dan lived together on the 13th. As it was Friday night I threw a couple loads of laundry into the wash and went downstairs to cadge ... Read full Story
shemale lover 2013-02-12 6,239 Cumshot sucking Blowjob ass fucking swallowing
100%
Allison the pool slut part 1
Allison had now had her fair share of whore experience. The teen boyslut had fallen in love with big cocks, anal creampies, facials, swallowing, and the rest of the nasty fun she had while becoming a sissy whore for her black neighbor and his dark dicked friends. Little did she know she was going to... Read full Story
shemale lover 2013-06-05 7,770 Teen (18+) Cumshot Big Cock ass fucking Interracial cd
92%
Sissy schoolgirl and her black daddy
I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning... It was summer time. As always I spent m... Read full Story
shemale lover 2013-06-22 39,692 Teen (18+) Bareback Creampie Lingerie ass fucking Interracial cd
93%
Lakeside Awakening
If anyone had told the way I'd meet my soul mate a few years ago, I never would have believed it. It was my senior year of high school and I had recently gotten out of yet another bad relationship with a girl. Lina had been a pretty, chubby blonde with a nice personality but a nasty temper. We ... Read full Story
AlliV 2014-09-02 6,631 tranny ass Teen (18+) Big Cock jerking
55%
MY New Experience with Shemale in Pune
I was browsing on Planet Romeo one day and i came across this profile of Nisha shemale in pune. I sent her offline message and second day i got reply that she is available and she charges around 2.5K. then we exchanged contact numbers and i spoke to her and negotiated with her for 2k and she agreed.... Read full Story
Stud4Shemale 2014-09-17 21,935 Cumshot suck Blowjob shemale oral sex 69