Sort by
Relevancy

Free Stories

90%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 19,203 Big Tits sucking ass licking fucking
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 3,832 big dick shemale oral sex crossdressing
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 6,481 Cumshot Fetish oral sex cum swallowing
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,164 Crossdresser sucking Big Cock ass licking big boobs
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 4,997 Masturbation sucking Creampie Latex fucking
100%
A Ski Bunny is Born Chapter 2
My first real man. Hugs and kisses to everyone who contacted Kim and I expressing how much you enjoyed our first episode. This is the second part of our life story so far, and is the first follow up to 'A New Ski Bunny is born'. It recalls the first time that Kim and I included guys in our ... Read full Story
shemale lover 2012-06-21 4,800 anal sex Cumshot oral sex rimjob
50%
MIKEY DEVIENT MÉLODIE
Le tout premier jour où j'ai rencontré Heather, elle m'a clairement fait comprendre que le sexe était très important pour elle. La même nuit, lorsqu'elle m'a vu pour la première fois avec mon pantalon baissé, elle m'a expliqué que puisque mon pénis était bien trop petit pour jamais la satisfaire, el... Read full Story
Femboy 2021 2023-01-20 723 Stockings Crossdresser Fetish Big Cock Uniform domination
50%
HypnoSissy: Partie 1
DEVENIR COCKSUCKER Alors que je prenais le sixième chargement dans la gorge, quatre autres étaient déjà déposés dans mon cul et il me restait encore une file d’au moins six à attendre leur tour pour déposer leur chargement dans l’un de mes deux dépôts de sperme, je ne pouvais pas m'empêcher de ... Read full Story
Femboy 2021 2023-01-24 882 Crossdresser Fetish domination
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 5,399 Big Tits transsexual big ass
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 11,273 sucking Fetish transsexual
80%
Bisexual Black Man's Paradise
The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... Read full Story
shemale lover 2012-06-24 5,317 big dick tranny anal sex Cumshot orgy facial oral sex
42%
Black Man Becomes A Sissy Maid
My name is Anderson James Crawford. I'm a big and tall young Black man living in the City of Ottawa, Province of Ontario. I presently attend Carleton University, where I'm studying Criminal Law. I originally hail from the City of Atlanta, Georgia. Yeah, there are African-Americans living in the Conf... Read full Story
shemale lover 2012-07-01 3,993 Cumshot oral Sex Toys crossdressing
80%
How it started
What got me started off watching shemale porn was actually meeting a very beautiful shemale at a beach party. I already knew she was a guy but she was so beautiful. So at one point I asked her if she wanted to go for a walk and after a few minutes and let her know that I was down. Her response was ... Read full Story
PNPFUCKBOY 2019-02-12 11,672 Teen (18+) Small Tits Crossdresser Amateur Big Tits Outdoor Latina Bareback blonde Big Cock Ladyboy domination Guy Fucks Shemale Interracial Sex Toys Mature Homemade Ass to Mouth
25%
CDSissy1 Training Regiment
New regimen for sissy Just wanted to say that lately I have a lot more time and freedom so I can play more....for the moment I have placed myself on a strict routine. I have to fuck my 8" dildo ON MY FUCKING MACHINE I figured that is a pretty good set up for an aspiring BBC slut.. It is important b... Read full Story
CDSissy1 2019-01-28 3,356 Stockings Small Tits Bareback Fetish blonde Big Cock Guy Fucks Shemale Interracial
72%
Wie sich schlagartig mein Sex Leben änderte... Teil 1
ich war nun schon einige Zeit heimlicher Crossdresser. Nie wurde ich von meiner Freundin erwischt, auch wenn es manchmal wirklich knapp war! Ich hatte ein sicheres Versteck für meine schönen Sachen und meine Sextoys und konnte hin und wieder meine geheime Neigung ausleben wenn sie nicht da war.Trotz... Read full Story
Holly Swallow 2019-03-20 7,660 Stockings Small Tits Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob blonde gangbang domination Interracial Sex Toys humiliation Homemade sissy girlfriend chastity cage Ass to Mouth cum in mouth chastity sissy amateur crossdresser fendom
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 3,858 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
100%
Making my CD slut fantasies become real
Having an open mind and saying yes to a TS friends' idea has lead me to discover things I never even knew about myself. I’ve always been into kink, but my adventures as a CD have shown Me that I have filthy perverse cravings to satisfy with people I’ve yet to meet. I enjoy transsexual escorts and th... Read full Story
pinkybrown666 2021-05-20 5,258 Crossdresser Amateur Group Sex Creampie Fetish threesome gangbang Interracial cum in mouth blonde cd
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 5,778 sucking fuck orgasm crossdressing
50%
A Perfect Life
The reasons I am not writing this myself. I have finally convinced someone to do it for me. She promised to post it on the Internet, but only as fiction. I suppose it is a bit unbelievable. It all started with the best of intentions. I had married my love while we were still in college. She... Read full Story
shemale lover 2012-05-05 12,435 transgender
82%
Bikini Boy
I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage... Read full Story
shemale lover 2012-06-12 15,275 Cumshot Fetish oral sex crossdressing
100%
Francis Meets a Black Stud Part 2
The first story was easy and this one went by pretty well. If you have any thoughts or suggestions for where Francis should go in installment #3 email me. I will respond to your email and sometimes I will send out previews of what I am working on if you treat me right. Thanks. As I was walking to... Read full Story
shemale lover 2012-11-20 3,703 Stockings cum Ebony oral
78%
Bikini contest
I was at this beach bar in Mt Pleasant SC. There was a bikini contest that day. As I attended, the contest started. I was 23yrs old and the thought never crossed my mind about a tranny. However this was supposed to be all girls. Nobody, including me suspected this girl that won the contest was a tr... Read full Story
jim3801 2017-08-09 19,009 Small Tits Ebony Lingerie Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
14%
Young CD wants to be used
My biggest desire is to have my make up done by a professional. And then be tied up in a room where all of a sudden at least 10 Big Badass guys enter the room. They use and abuse me and put cum all over and all inside me and they leave me there tied...... Read full Story
ASlaveToYourCocks 2018-03-02 2,882 Stockings Lingerie domination Interracial Sex Toys cum in mouth double anal
40%
Kiara's Xtra large treat
I have developed an interest in t girls with the XXL tag, black and Latino girls especially seem gifted in that department, so when I seen this horney bunny on an escort page I knew I'd have to check her stats. A dark Latino Kiara boasted an impressive ten inches, I pondered on my way to meet her... Read full Story
Kinky Dee 2019-05-27 3,471 Small Tits Big Cock Lingerie domination Guy Fucks Shemale Interracial
100%
TO BE OR NOT TO BE - PART 7
TO BE OR NOT TO BE - PART 7 by Spanky de Bautumn Part 6. Sunny, Mel, and Shari had a heart to heart and Mark took Sunny for a night on the town. I woke up next to Mark, he looked so peaceful sleeping. Was I dreaming? Did I fall asleep and dream that Mark said he was going to take me shopping... Read full Story
SpankydeBautumn 2021-03-01 2,494 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
Inmediatamente despues
Luego de que el termino en mi nalga, todavía con la sensación de placer que teníamos los dos, me beso tiernamente y me pregunto donde quedaba el baño. Yo todavía de rodillas en el sofá, pase mi mano izquierda sobre mi nalga y sentí el semen que mi macho había depositado sobre mi y lo trate de recoge... Read full Story
maritza_tv 2023-04-28 1,245 anal Crossdresser Amateur Creampie Big Cock Ladyboy Lingerie Guy Fucks Shemale Interracial Mature Homemade sissy femboy
100%
Gangbanged at the beach
My BBC friend took me to the beach, where people make sex. We arrived in his van. I was in the back of the van, chained blind folded, with my mouth wide open and a huge horse dildo in my sissy pussy. Suddenly I hear the van door opening. I hear many voices of other men. My BBC friend was telling oth... Read full Story
brunasissyslavedolrj 2022-05-09 4,386 Crossdresser Group Sex Outdoor Fetish Big Cock Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
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 6,060 Crossdresser Amateur Cumshot Big Cock ts posing huge dildo
100%
La Entrevista (trabajo de mesera)
LA ENTREVISTA (Trabajo de Mesera) Esta historia es una gran fantasía que tuve por años, pero que ahora aunque a medias es una realidad. Krystal, una de las chicas que me ayuda con el maquillaje, varias veces me había hecho el comentario de que en el bar donde ella actuaba, necesitaban a una chi... Read full Story
Salma TV Pasiva 2023-01-19 1,318 Stockings Crossdresser Amateur Latina Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial
100%
TELLE MÈRE, TELLE POULE MOUILLÉE
Je n'ai jamais connu mon père. Ce n'est pas une excuse pour ce que je suis devenu – et cela ne veut pas dire que j'ai besoin d'une excuse – c'est juste un simple fait que certaines personnes trouvent pertinent lorsqu'elles essaient d'examiner ce que je suis devenu. ... Read full Story
Femboy 2021 2023-02-03 3,333 Stockings Blowjob Big Cock Lingerie domination Interracial cum in mouth
50%
Towel Boi: Heading to Work
“Goddamn, white boi! You got the best fuckin’ ass,” declared the father of two. His steel manly form perspired as he moved hard into the bottom. “Look at all that butt shake! Twerk it for me, baby boi!” “Yes, sir,” cooed Kasey, gyrating rhythmically. “Hell yeah! It’s like fucking two big ol’ ma... Read full Story
Faggyboi and Puzziboi 2023-11-17 5,891 anal Crossdresser Bareback Creampie Blowjob gangbang Lingerie Guy Fucks Shemale Interracial sissy femboy bbc
100%
A Flash of Lace
The insistent ringing of the phone broke my concentration and with great annoyance, I climbed off the bed and picked up the receiver. "Hey little brother!" My sister's sparkling voice filled my ear. "Di, Is that you?" I exclaimed happily "Got any more sisters I don'... Read full Story
shemale lover 2012-03-03 6,016 Stockings Fetish dressing
100%
Britney Story
Yeah, for those of you that have already read it, this is just my "Oops, I Did It With Britney" story that has previously appeared in four separate parts in the "celebrities" section, but I've put it on here for a couple of reasons. For one thing, I've noticed that the stories in... Read full Story
shemale lover 2012-09-25 8,944 Cumshot sucking Creampie shemale
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 10,345 anal tranny Cumshot oral
80%
Dream Date
Who would have thought it; I was reduced to finding a partner on the Internet? I had read about these dating web sites and though dubious I found one, completed my details and waited. A few days went by and I heard nothing. I waited a few weeks and still I heard nothing. I turned to an old girlfrien... Read full Story
shemale lover 2012-11-14 4,759 Fetish heels
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 30,209 Teen (18+)
75%
Aunt Susie's Training Part 5
Aunt Susie and I woke up around 1030AM and Aunt Susie said we need to get ready for a surprise appointment in the city. We put on our make up, I pulled a ponytail again and we got dressed in jeans and heels and matching white button down shirts which we left untucked. We drove first to Aunt Susi... Read full Story
BITCHGURLvr 2024-05-16 1,910 cock sissy Cigarettes
100%
Daddies New Girlfriend
Doug suspected his 19 year-old son Jerry was stealing money. Doug worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror to film his dead wife Cyn... Read full Story
shemale lover 2012-03-09 12,061 sucking Fetish crossdressing
50%
A Murder Misstery
When I rolled out of bed that fateful morning, I had no way of knowing that it would be my last day as Matt McCoy. After showering and dressing quickly (how I long for those days!) I bolted out the door for my train, looking forward to another manic day on the floor. Although I was one of the younge... Read full Story
shemale lover 2012-03-20 4,939 Fetish crossdressing feminization
100%
A Strange Affair
"I think you'd better come in," said the blonde-haired woman. She opened the door to the apartment fully, and stood aside as I walked through the door. She was attractive enough -- it was hard to see why her husband would want to cheat on her. She was very tall, and made taller by her b... Read full Story
shemale lover 2012-07-01 4,701 Cumshot Fetish Sex Toys crossdressing
25%
A Strange Romance
Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to ... Read full Story
shemale lover 2012-07-05 6,795 Creampie Fetish crossdressing virginity
100%
Fender Bender Chapter 9
My name is Robert, I have been cross dressing since I was 14. I turned 18 last summer and this story takes place during my senior year in High School. I am 5'9" 160 pounds, blonde hair and blue eyes. When I am dressed I call myself Vicki. __________ I had met Julie at a recent party. Well... Read full Story
shemale lover 2012-07-27 3,333 Group Sex Cumshot Sex Toys
100%
Whitney's Way
My arms were stretched over my head as I finished hanging the last sheet of drywall. Another step closer to the end of the two year process of renovating our first house, it was hard to conceal my sense of pride at turning a worthless wreck into the nicest place on the block. But as soon as I heard ... Read full Story
shemale lover 2012-11-18 8,426 Cumshot oral sex kissing
100%
Angel Chapter 2
Angel Jones stepped off the train and hoped she was in the right place. It was noisy and confusing in the terminal, a far cry from the relatively quiet station in her home town where she had boarded the train that morning. One hand clutched a small suitcase that contained her makeup and clean linger... Read full Story
shemale lover 2012-11-30 4,173 oral sex tgirl feminization
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 8,958 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
50%
LA FEMME CONVERTIT SON MARI
Je m'appelle Tony et je mesure 5'8 ", ne pèse que 58 kilogrammes, sans graisse corporelle et un chiffre pour lequel la plupart des filles tueraient selon toutes les filles que je connais. J'ai un teint olive et je bronze très bien, J'ai les cheveux bruns courts et les yeux couleur noisette. Je suis ... Read full Story
Femboy 2021 2023-01-06 774 Stockings Crossdresser Amateur Fetish
100%
The Interview
The Interview By Sabrina G. Langton *** 'A crossdresser goes on an interview in lots of pink, of course she gets the job' 'Author's note, just a quick little story with some really graphic sex, and a little tiny moral. I hope YOU like it.' *** "Okay, sit, sit, let's get started. S... Read full Story
Brina Giselle 2023-12-04 6,376 anal Crossdresser Blowjob heels cum in mouth pink dress
85%
Unforgettable First Time
I am in my late thirties and have known for a while that I have a sexy body. I'm 5'11", slim and athletic with little cherry butt and shapely legs. A lot of women have told me my body is sexy. A few men have mentioned it too. Sometimes I get photo-snapped at the pool or the beach. I've been luc... Read full Story
shemale lover 2016-05-06 10,062 cum oral deepthroating
100%
What I dream about
I'm shortly to embark on a trip to amsterdam in the new year and am very excited for one thing in particular, the opportunity to come across a real life shemale! I've been a massive admirer of shemales for a long time now ever since I first saw one. I don't remember exactly how I came across them b... Read full Story
shemale lover 2011-08-11 3,146 asshole licking fingering
50%
My First Time Out Part 4
It was Sunday morning at eight o’clock when the phone rang. Shayna’s eyes felt like they were glued shut but managed to answer the phone on the third ring. “Morning,” said Shayna as she was still half-asleep. “Good morning Shayna. This is the Bell Captain calling.... Read full Story
shemale lover 2011-10-18 4,381 cum oral facial deep throat fucking
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,116 Fetish transformation dildo
100%
The Bitch Bites Back
Pamela stood huddled in the dark doorway, halfway down the back alley. It was cold and a light drizzle had settled in, the sheets of fine rain just discernible in the dull light of the single working lamp halfway down the alley. Pamela was in her mid forties and fighting a losing battle against t... Read full Story
shemale lover 2012-05-12 7,390 anal sex Cumshot oral sex wanking 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 5,548 anal sex Creampie oral sex cum swallowing
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 13,919 hardcore sucking ass fucking Guy Fucks Shemale
100%
Betrayed Chapter 4
I really wasn't surprised when Dianna directed me into the parking lot at Ringers. It was only a few blocks across town from my new home; a five-minute drive, if the traffic wasn't killing at the time. Consciously, it had not been a factor in my decision to take the new place. Sub-consciously... wel... Read full Story
shemale lover 2012-05-29 4,951 Cumshot orgasm condom sex
100%
Blushing Bride Chapter 2
`I stood there, with my hand on the doorknob, waiting to go into the living room where all my friends sat drinking to celebrate my upcoming marriage. I hesitated there for a moment, not quite sure what their reaction would be upon seeing me dolled up like this, my fiancee's beautiful strapless weddi... Read full Story
shemale lover 2012-07-21 3,760 oral sex cum swallowing crossdressing