Sort by
Relevancy

Free Stories

100%
How A straight tatted white guy turned me out to a femboy
So I met this straight white guy on an app (wont say) hes tatted a bit thuggish and likes black femboys I noticed. At that time in my life I really didnt embrace being femme I was kinda in the middle doing the cute gay twink boy thing. He didnt mind me presenting male he did like black guys or femme... Read full Story
Ezra_Kyle25 2024-07-18 1,379 Crossdresser Amateur Ebony domination Guy Fucks Shemale Interracial big ass Homemade sissy femboy interracial fuck
100%
Black Transsexual Power Play
The name is Christopher Jean-Bertrand. I'm a young Black man of Haitian descent living in York, a town located right outside the City of Toronto, Province of Ontario. I currently attend York University, where I major in Civil Engineering. Yes, I'm a deeply intellectual kind of guy. We have those in ... Read full Story
shemale lover 2012-07-11 3,155 anal tranny Creampie Ebony
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 15,248 first time ass Cumshot suck cd sissy make up
81%
White sissy used by black Masters
I’m booked into a London hotel and, after you text me to say you’ve arrived, I text you back the room number. It seems like ages before I hear a firm knock at the door and I jump up, excited but nervous about what’s about to happen. I walk over and unlock the door, careful not to m... Read full Story
shemale lover 2011-11-12 9,360 shemales interracial sex bdsm
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 6,577 sucking cum massage
50%
Freak House Superstar Come Fest
Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... Read full Story
shemale lover 2012-02-01 6,341 anal shemales Group Sex
83%
PF's Black Romp and JoyceLynn's Awakenin
When my wife and I first met, our sex life was fantastic! She was a very sexual lady and always made herself available. She usually wore stockings and garter belt or thigh highs, high heel sandals, and something that was sexy and suggestive. We made love and had sex in every room of the house, inclu... Read full Story
shemale lover 2012-05-17 4,318 Fetish Interracial Sex Toys
50%
champignons sous toutes ses formes et façons
La saison des champignons est ouverte! Miam... J'adore les champignons, sous toutes ses formes et façons. Nous sommes une quinzaine d'amateurs qui se retrouvent uniquement à l'occasion des ceuillettes de champignons sans aucun autre rassemblement amical! Pour cette dernière sortie de la saison,... Read full Story
hippocampus_171 2023-11-24 603 anal Small Tits Amateur Masturbation Mature small cock big ass bisexual Homemade cum in mouth bald
86%
La primera vez que me hicieron mujer
Desde mis mas lejanos recuerdos, siempre sentí la necesidad de lucir femenina...recuerdo que de niña me encerraba en el cuarto de mi mama y me probaba las medias panty y los tacones, sobre todo unas sandalias doradas que me encantaban...podía pasar horas en esa habitación imaginándome siendo toda un... Read full Story
maritza_tv 2023-04-28 10,479 anal Small Tits Crossdresser Amateur Bareback Creampie Big Cock Guy Fucks Shemale Interracial Mature cd sissy femboy
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 1,365 anal Crossdresser Amateur Creampie Big Cock Ladyboy Lingerie Guy Fucks Shemale Interracial Mature Homemade sissy femboy
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,044 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
50%
I kneel in front of Dominatrix Persephone
Fan Mail. I kneel in front of Persephone.. She looks amazing in Her latex catsuit, but there is something else eye catching. Chance, Persephone huge hó rse c... It looks intimidating in picture, but just think how it must look when it is right in front of your face!! Holding it in my sissy hands, i... Read full Story
Dominatrix Persephone 2024-06-18 2,998 anal Stockings Cumshot Shemale Fucks Guy Fetish Big Cock redhead domination Interracial Mature Homemade sissy femboy teen (18+)
100%
Property To Be Pimped
It had been weeks since I'd brought to light my idea of my wife, Suzie, strapping on a big dildo and taking me dressed as Desiree, the Hot to Trot Transvestite. While at first she teased me with possible participation, it never came to be, despite me bringing it up on several occasions. She really d... Read full Story
shemale lover 2013-01-17 7,264 Stockings Crossdresser sucking dildo Interracial
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 3,986 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
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 4,481 tranny Group Sex cum Ebony oral sex
81%
A LadyBoy For My Wife
I have been happily married to my sexy Thai wife Lisa for three years now. My wife is Thai is petite (5'1") with a stunning figure, a tight ass and long waist length black hair. We had met in a bar in Thailand and subsequently we were married back here in the UK. She was very loving with m... Read full Story
shemale lover 2012-06-23 10,839 Group Sex Masturbation shemale Ebony facial
57%
Amsterdam shemales
This was a few years ago I decided to go to Amsterdam and see if I was gay . Booked A weekend and went drinking,went around the the red light district see what girls and others were around. Went to this beautiful brunnett girl from Bulgaria with big tits, she started sucking me off but I could not ... Read full Story
Saoirse1973 2017-06-28 16,815 Shemale Fucks Guy Blowjob Ebony Interracial
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
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
94%
CD and BBC Gangbang 1
My name is Mike, as a "Gurl" I go by Fiona. I am a gay man, mid thrities, white, 5' 9' 165, reasonably handsome, both in and out of women's clothes. One of the ways I express my sexuality is to dress as a woman and get fucked by other men. Preferably in a humiliati... Read full Story
FionaFucked 2014-10-27 13,855 Group Sex gangbang Interracial cd sissy
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 19,173 Small Tits Ebony Lingerie Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
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%
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 5,850 Masturbation orgasm fantasy tg
90%
White dress!
It had been a long and hot day that sunday! Some friends opted the idea to go drinks and have a cookout, little did i know how the night would end. By the time it got to midnight we were all drunk and wanted more action so we decided to head to one of the local bars for more drinks and see if we fo... Read full Story
PeterPiper 2018-03-22 6,095 Masturbation Bareback Mature Ass to Mouth cum in mouth
69%
Kits Adventures in the North
**Crossdress Story** It had been about six months since I'd had any chance to dress, any chance to feel sexy and been even longer since I had any kind of sexual contact. Work tends to do that; gets in the way and screws about with "me" time. Luckily, though, it was only a temporary job... Read full Story
shemale lover 2015-08-31 5,580
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 3,790 Stockings cum Ebony oral
75%
Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... Read full Story
shelli_k18 2021-04-20 8,446 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
50%
A Married Marilyn
"Class is dismissed. Don't forget the project due…" "Huh, what?" Marilyn woke up disoriented from her nap. When she finally came to, she vaguely remembered some project for Intro to Computer Science, gathered her legs from the chairs in front of her, dusted off her b... Read full Story
shemale lover 2012-03-18 7,186 Group Sex Masturbation sucking Sex Toys
50%
An alumni gathering like no other
An alumni gathering like no other; Sea/Sand/Sun' and why not 'Sex' in a vancancy club; we got together to celebrate the 40th anniversary of our 1st meeting at university. The only rule was to come without a partner to relive our 'frosh' days. with friends of whom I had lost all trace, a... Read full Story
hippocampus_171 2024-06-13 1,663 anal Amateur Masturbation Blowjob Sex Toys Mature small cock big ass Ass to Mouth cum in mouth
83%
Janine awaits
My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... Read full Story
bunny cat 2019-02-04 3,815 Crossdresser Masturbation Blowjob Lingerie Mature cum in mouth
100%
How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
Chrissy Tunnell 2022-01-27 4,173 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 4,041 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
Buying Heels
I have to know what it feels like to wear heels. I have the house to myself tonight and I'm going to play. I already have panties but want to buy some new ones. My wife bought me a black, frilly thong which I wore for her when we went out one night; I also have a cheap, supermarket pair of sheer ... Read full Story
shemale lover 2012-09-30 4,760 Stockings Cumshot oral sex crossdressing
80%
A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... Read full Story
shemale lover 2011-12-06 11,495 Bareback cum ass fucking slave
100%
The Mocha Club... A Wife's Awakening
Fran had spent a restless evening in her hotel room, flicking through the channels on the television, finishing the large glass of red that room service had brought her and writing up the actions from the client meeting earlier that day. Now she was bored. It didn't help that the hotel her manager h... Read full Story
ASSEaster5678 2018-07-09 9,041 Amateur
80%
Michele And The Predator
The predator peered through the bedroom window and smiled; he couldn't believe his luck. This woman was just to his taste; he felt himself begin to stiffen as his eyes devoured her; he couldn't wait until he had his hands on her. In his mind he played out the scenario that he envisaged would soon ta... Read full Story
shemale lover 2012-05-13 4,397 Fetish transvestite fiction
50%
Rassemblement d'alumni pas comme les autres;
Un rassemblement d'alumni pas comme les autres; 'Mer/Sable/Soleil' et pourquoi pas 'Sex' dans un club de vancance; nous nous sommes rassemblés pour fêter les 40 ans de notre 1ère rencontre en fac. La seule règle était de venir sans compagne pour revivre nos jours de 'frosh'. avec les ca... Read full Story
hippocampus_171 2024-06-13 96 anal Amateur Masturbation Sex Toys Mature small cock big ass Ass to Mouth cum in mouth
50%
Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
shemale lover 2012-02-08 7,175 fuck oral
80%
Office Policy
“Ok ladies and gentleman, please put your hands together for the beautiful and talented Erika!” the DJ’s voice rang out over the thumping alternative beat as the object of my lust strutted to the stage. Erika’s saucy red curls bounced on her head and on her soft porcelain whi... Read full Story
shemale lover 2012-08-30 8,474 anal ass sucking threesome tits fingering sex blondie
80%
Debbie Part 7
As Debbie was led into Dr. Jacobsen's office, she saw that Mistress was already there waiting for her. "Your property Miss Chamberlain", the doctor proclaimed, indicating Debbie. Debbie's heart began to flutter with love and submissive fantasies as she saw Mistress. Mistress was dressed in... Read full Story
shemale lover 2011-12-23 9,589 transgender toys bondage and discipline heavy
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 7,499 anal sex Cumshot oral sex wanking cum swallowing
83%
An Arse To Die For
I'd arrived in Honolulu in the early evening from Sydney and got a cab straight to my brother-in-law's apartment on Kuhio, which he'd lent me for a fortnight while he was up in Europe on business. It's in an ideal situation, a couple of blocks back from all the hotels and Waikiki Beach. I slept l... Read full Story
shemale lover 2012-11-10 4,423 anal tranny oral
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 4,360 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots