Sort by
Relevancy

Free Stories

86%
Shemale Love Story - part 1
Let me tell you a story of a shemale and her lover. Some background is required here. My girlfriend (we'll call her Lisa) was at the time about 27 years old and had been single for sometime after a bad experience with a man. She is a stunning girl, and most people would not know she was transsexual ... Read full Story
shemale lover 2015-10-05 20,434 cock shemale nipples
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 2,410 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
100%
My Girl Friend and A Shemale
I walk up to the door of my girlfriend’s apartment. As I start to slide the key into the lock, I can hear slight muffled noises from inside. As the door slowly opens, I am met by the sight of my girlfriend laying with her legs spread wide open on the couch and her super sexy friend Shayla, w... Read full Story
tgirlloverme 2011-09-07 7,329 threesome shemale oral
100%
My Sugar Daddy Spanked Me & My Girlfriend (I screwed up again)
In my last fantasy article I explained how my Sugar Daddy allows me to date girls since I am bisexual and attracted to them too, but they, and in fact anyone, are not allowed to touch me intimately without explicit permission from my Daddy. Anytime a girl wants to touch me: kiss, hold hands, put her... Read full Story
Chrissy Tunnell 2022-04-12 2,015 Crossdresser Amateur Big Tits Shemale Fucks Guy Fetish threesome Blowjob Big Cock Ladyboy Shemale and Girl Guy Fucks Shemale cum in mouth
100%
Jo, Shemale Goddess! Part 1
Jo plumped the cushion and carefully positioned it until it was precisely at the right angle. Nothing less than perfection would do. Ricki, her friend of twelve years was coming to stay overnight and she would notice if the tiniest thing was out of place. An impatient knock on the door signalled ... Read full Story
shemale lover 2011-09-04 5,146 anal sex sucking shemale
94%
My Shemale Fantasy
Allow me to introduce myself, i’m a young European man, in my early twenties, writing my first erotic story. This has been a fantasy all my life, it probably will remain a fantasy, but that doesnt mean i cant write about it. Ever since i was old enough to realize my raising sexual interest and... Read full Story
Jakester 2013-04-10 31,244 first time Creampie Shemale Fucks Guy ass licking virgin
94%
My first shemale
This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when... Read full Story
shemale lover 2012-02-12 12,861 first time Creampie Shemale Fucks Guy
100%
Kate Berges the Shemale who fucked first in my ass
I was with her last week. She was in a duo. So I went there and rang the bell. Recognized me right away and gave me a deep kiss. I then asked her if she was available in the duo and her colleague a.) cums properly and if she would also fuck each other, which she confirmed. She then went out and c... Read full Story
Bigpruegel69 2023-12-17 6,155 Cumshot Creampie threesome Blowjob cum in mouth shemale + shemale
100%
TG girlfriend is my new neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-01-17 3,854 Big Tits Bareback Creampie Shemale Fucks Guy Big Cock Asian Guy Fucks Shemale
40%
See Me At Shemale Cam Tube
I was dressing when I heard a new e-mail arriving. "You're hot as hell on Shemale Cam Tube", he wrote, "Wanna meet me 4 lunch? Promise to be a gentleman!" It was cute, especially coming from such a skinny guy. I'm a big girl - over six feet, with strong legs and huge breasts whic... Read full Story
shemale lover 2011-08-09 6,143 asshole Blowjob shemale
80%
My Lesbian Shemale Experience
Me and my friend Sarah was driving to Calfornia , for Summer Vacation. SO we packed our bags , and sat them at the door , and we were ready to go , and then my friend Sarah had to go pee, man was i mad , when she said that, because i just wanted to hit the road. so i waite until she was done, and th... Read full Story
shemale lover 2011-08-16 3,257 pussy shemale fingering
90%
My first shemale encounter
I remember the first time I found myself in bed with a shemale. I had just broken up with my girlfriend. I was lonely, I was horny, and I had zero intention of finding myself in another relationship with a woman. When I told my buddy, Bob, he told me he knew just where to take me to solve this. So ... Read full Story
shemale lover 2014-08-17 8,594 licking sucking shemale
80%
First time shemale encounter
Lets start off by saying this a very true story, one that i love to re-live over and over. lets begin I was in el paso, texas..my girlfriend at the hotel. Something in me decided to go to the strip club. So i did. After a few dances, i decided to leave. I had always heard in mexico it was very ea... Read full Story
iloveshemales112 2011-12-17 9,084 Latina Bareback Shemale Fucks Guy Big Cock
92%
Shemale feet
Hi, im a 20 year old european guy with a true great story I wanted to share with you people. It all happened on a warm but rainy day in the summer, was single at that time. I broke up with my girlfriend because we didnt came along anymore. Anyway, I was bored, not to many options and everyone els... Read full Story
Antwerptslover 2014-12-03 8,446 first time ass shemale Big Cock feet
97%
Shemale fucks guy - My gf fucks my slutty ass.
I have a shemale girlfriend & we both are in a relationship. One day, I decide to give her a visit. I'm 5'7 guy & she's 6 feet. That makes her tall & intimidating & whenever we meet, it's me who become her gf. I visit her, she takes me in. SHe pulls me towards her while giving me a deep kiss. I ... Read full Story
glodobox 2020-12-04 21,595 Amateur Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Homemade cum in mouth
100%
Cat hat einen riesen shemale Schwanz
In meinem zweiten Studienjahr fing ich an, mich mit einem der heißesten Mädchen auf dem Campus zu verabreden. Wir hatten uns in meinem Kurs Geschichte des Römischen Reiches kennengelernt und verstanden uns von Anfang an Ich brauchte fast ein ganzes Semester, bis ich den Mut aufbrachte, sie um ein Da... Read full Story
jimyblue 2021-11-22 3,067 Bareback Shemale Fucks Guy Big Cock cum in mouth
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 3,350 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
My shemale GF
So my girlfriend ,who was originally my friend ,who I had no idea was a shamale, she hid it very well, she is white with brown hair and blue eyes, she is very pretty, has nice boobs very perky, great ass, and a beautiful voice, I asked her out, she was hesitant at first it took her awhile to say yes... Read full Story
shemale lover 2012-07-03 3,779 Blowjob shemale facial jerking off
87%
First Time - Surprise Shemale
I'm an eternal masturbator. I've always like wanking and playing with myself. At a young age I worked out that I likes playing with my ass hole, sticking things in it, walking round all day with something in it. With the advent of the internet I was like a pig in shit. So much porn to be had and so ... Read full Story
shemale lover 2014-09-19 19,096 first time tranny Shemale Fucks Guy jerking wanking 69
85%
Buffy the Shemale Vampire Slayer Part 1
Waking to sunlight streaming through her bedroom window, between the parted curtains, Buffy Summers frowned, blinking. She'd had some strange dreams, including a few that had been prophetic, but nothing like the bizarre nightmare she'd awakened from just now. Last night, she'd fought a Feral Demon a... Read full Story
shemale lover 2011-08-19 5,256 Cumshot shemale hermaphrodite
66%
Buffy the Shemale Vampire Slayer Part 4
Damn! Wherever Willow was, she wasn't home. The witch still hadn't returned to her motel room. At least, this time, Buffy hadn't had to rely on Sunnydale's public transportation system. Xander had given her a ride across town. He'd offered to wait, to make sure that Willow was back, but Buffy, wa... Read full Story
shemale lover 2011-08-19 3,596 shemale orgasm nipples
83%
Buffy the Shemale Vampire Slayer Part 6
Buffy arrived in the demon dimension on her elbows and knees, just as she'd been when her mentor, Rupert Giles, had been butt fucking her a moment before the spell they'd cast transported her from his apartment to this bizarre land of the damned. Her legs were still spread wide apart, and ass was st... Read full Story
shemale lover 2011-08-19 4,054 asshole shemale Big Cock
100%
Betrayed Chapter 10
I would have loved to be waiting at the gate at O'Hare when Dianna de-planed from L.A. that Sunday night. I had to settle for the Baggage Claim Area. Those people working for the Transportation Security Administration have no sense of humor. I guess at eight dollars an hour, they can't afford one. T... Read full Story
shemale lover 2012-05-30 4,464 hardcore shemale fuck
88%
Shemale Ride Along (Part 3)
It was the last day of classes. All of the finals were finished, and everyone was celebrating. My finals had been particularly rough. It was the last semester of my freshman year and I didn't study as much as I should have. The problem was that I lived next door to a girl that I had been having... Read full Story
qtball 2016-09-26 21,178 anal tranny Blowjob Big Cock bj Ass to Mouth
100%
Tina's Secret
My name is Jordan Conrad. Those of you who read my "Rebecca's Secret" series probably remember me. If you've never read them, I guess I should give you a quick summary, so you're not in the dark about what's been going on in the past few months of my life. Bear with me during the slo... Read full Story
shemale lover 2011-11-02 7,051 asshole shemale oral
100%
My First Time Out Part 3
Angelo was still working on Shayna's blonde wig. He fussed with it, combed it, and teased it. Angelo knew a romantic style was very important to Sir Dominique. Shayna was escorted to a tremendous makeup table. Saki placed a headband on her that stretched her scalp and raised her non-existent eyeb... Read full Story
shemale lover 2011-10-18 4,031 blonde shemale massage
62%
Rebecca's Secret Part 3
Kate stood before me, dressed in only a burgundy bathrobe, with her back to the door. She looked up at me as if waiting for me to say something, as if I was the one who needed to provide an explanation. Rebecca, meanwhile, stood behind me, using my body to shield her from Kate's eyes, not that it ma... Read full Story
shemale lover 2011-10-20 4,933 anal sex shemale orgasm
100%
Betrayed Chapter 2
The sex was torrid and went all night. I worshipped every inch of her magnificent body with my lips, tongue, fingertips. She did the same to me. I took her from behind, entered her doggy-style. I fucked her pussy with long, languid strokes even as I was stroking her meaty clitty with one hand. I wil... Read full Story
shemale lover 2012-05-28 4,753 Stockings shemale cum
72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 10,995 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
90%
Caught by the Lodger
Having split up with my girlfriend about six months before, I was getting a little bored of living on my own. I'm a 29 year old guy living in South London and I thought it would be a good idea to get a lodger. I had a spare room that was empty, the company would be good and the extra money would com... Read full Story
shemale lover 2012-06-22 5,373 shemale oral sex Sex Toys strapon
87%
Feminized By My Mother
Hello. My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is inv... Read full Story
shemale lover 2012-07-24 66,792 Fetish shemale oral feminization
66%
A Girl's Best Friend
The party was in full swing when Ryanna and her friends arrived. Of course, they were an hour late, since Glenys had gotten lost on the way. The house was out in the back woods; the owners didn't exactly go out of their way to make it easy to find. Their fellow townspeople probably would have frowne... Read full Story
shemale lover 2012-03-06 5,248 Crossdresser Shemale and Girl oral sex condom sex
83%
Caught at Lunch
Only so long can you hide, if you are wondering what the hell I am on about then let me explain. As a part time transvestite dressing is always a thrill as is the joy of turning myself from a very average looking guy into a sexy cock loving slut, but due to where I live the chances to fully dress... Read full Story
shemale lover 2012-06-11 3,596 anal sex Cumshot shemale fingering transvestite
100%
Whatever Your Heart Desires Part 6
I was excited about going out with Lexi, more so than I had been about anything in the months since Danni left. The prospect of spending my birthday alone, without my sweetheart, was just too daunting. Being dragged out of my self-imposed exile for a night of drinking and dancing actually looked lik... Read full Story
shemale lover 2012-12-09 3,495 Stockings shemale transformation
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 32,331 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
50%
DU VILAIN PETIT CANARD À LA PRINCESSE SISSY ⚧️ ⚧️
Être un mec très petit 1 mettre 60 avec une petite carrure a été un handicap majeur dans ma quête de compagnie féminine. Avoir un micro pénis était le clou de mon cercueil. Tout au long de ma jeunesse, j'ai été ignoré ou rejeté par les filles. J'ai eu ma première petite amie à l'unive... Read full Story
Femboy 2021 2023-03-23 635 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial cum in mouth shemale + shemale
100%
Exposure, Disclosure
The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... Read full Story
the greatest liar 2019-06-18 7,237 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
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 5,526 Big Tits Bareback Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
100%
C'EST LA PATRONNE
Le rêve est mort. L'écriture était ma passion, mais cela n'a jamais servi à rien. La réalité a une mauvaise façon de vous rattraper, déchiquetant vos désirs dans son sillage. Ce cycle d'épargne et de vie de ces économies s'est progressivement révélé intenable et maintenant, à ving... Read full Story
Femboy 2021 2023-02-06 1,191 Stockings Shemale Fucks Guy Fetish Futanari cum in mouth shemale + shemale
100%
FOUTAREICH
Le Parti de l'apothéose féminine, ou FAP, a reconnu les différences physiques entre les hommes et les femmes. Cependant, la FAP a affirmé que même si les femmes pouvaient être physiquement inférieures aux hommes, elles étaient moralement supérieures. Tant que les hommes seraient plus forts que l... Read full Story
Femboy 2021 2023-02-11 831 Crossdresser Cumshot Shemale Fucks Guy Shemale and Girl Futanari cum in mouth
100%
LE PARI (MAMAN/FILLE FUTA)
Ma mère, Kendra, se promenait souvent dans la maison sans haut, laissant ses énormes seins couler librement. Ça m'a dégoûté. J'étais sa fille, pas un gars au hasard qu'elle a ramené à la maison un vendredi soir (pas qu'elle a ramené des gars à la maison). Elle ne devrait pas montrer ... Read full Story
Femboy 2021 2023-02-11 897 Teen (18+) Big Cock Shemale and Girl domination Futanari cum in mouth shemale + shemale
100%
ENFERMÉ HORS DE L'APPARTEM ⚧️ ⚧️
Je m'appelle Layton McGuire. Quand j'avais 22 ans, je vivais à New York et je partageais un très petit appartement à loyer contrôlé à Greenwich Village avec deux autres colocataires pendant que nous fréquentions le City College (qui est un vrai collège, pas seulement un nom générique, cherch... Read full Story
Femboy 2021 2023-03-20 567 Shemale Fucks Guy Fetish Blowjob domination Futanari cum in mouth
50%
MON NOUVEAU TRAVAIL ⚧️ ⚧️
Postuler à l'université a été l'une des choses les plus faciles à faire pour moi. J'ai décidé d'aller à l'université qui m'offrait le plus de bourses d'études et qui était loin de ma ville natale. Tout cela était facile jusqu'à ce que j'arrive à l'université. ... Read full Story
Femboy 2021 2023-03-24 571 Stockings Big Cock Lingerie Shemale and Girl domination cum in mouth shemale + shemale
85%
My dream pt 2
A few hours later I woke up and realized that I had fallen asleep. Sydney must have also fallen asleep as she was still in my arms. I tried to get up with out waking Sydney but that wasn't possible. She woke up and quickly put on her nightie so she could walk me to the door. When we entered ... Read full Story
Sydney Sun Min 2017-12-26 17,780 Shemale Fucks Guy
84%
She never saw it coming
When I was 19/20 I used to frequent LGBT bars roughly twice every month. Most nights not much would happen but I found myself going to the trans nights more often. Until I eventually had some experience with trans girls. It was mostly fairly soft fun. Me getting oral and occasionally topping th... Read full Story
chris1989r 2022-02-01 4,809 shemale gangbang facial
50%
Ma femme et maintenant elle va me transformer en Sissy
Karen et moi sommes mariés depuis 28 ans. Nous avons eu nos hauts et nos bas, mais nous sommes restés fidèles et avons produit deux excellents sexe en conséquence. J'ai toujours été secrètement bi. J'ai été pris au piège de quelques accessions, mais j'ai résisté aux tempêtes et j'ai visité des relat... Read full Story
Femboy 2021 2023-01-24 726 Stockings Crossdresser Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys
50%
Dame et jardinier
Piotr se tenait sur les escaliers de la villa de Klonowa Street, située dans le quartier à la mode et riche de sa ville. Il était environ midi par un chaud samedi de juin. C'était son dernier arrêt ce jour-là. Il avait déjà collecté l'argent des autres clients avec lesquels il traitait des jardins, ... Read full Story
Femboy 2021 2023-01-24 688 Stockings Crossdresser Cumshot Shemale Fucks Guy Fetish Blowjob Guy Fucks Shemale
50%
Maman se met en colère contre son fils Pussyboy
Histoire d'un fils de pussyboy qui est transformé en putain de bite par sa mère. À 31 ans, je ne devrais pas envisager de retourner vivre avec ma mère, mais j'ai récemment divorcé, mon ex-femme m'a viré et j'ai dû me mettre à genoux pliés vers ma mère pour un toit sur ma tête. C'est avec un sentim... Read full Story
Femboy 2021 2023-01-24 707 Stockings Crossdresser Fetish Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-26 1,166 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
100%
DÉBUTS INNOCENTS
"Avez-vous pris votre vitamine, ma chère ?" Ellen a appelé de la salle de bain. Je me frottai le sommeil des yeux et ramassai le flacon de pilule, roulant un gros comprimé dans ma paume. "Ma pilule de cheval ? Je le fais maintenant." "Avez-vous déjà remarqué une différence ?" "Non. Les vitamines ... Read full Story
Femboy 2021 2023-01-26 839 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale
50%
HOSPITALITÉ DU SUD
Ash regarda sa mère, incrédule quant à ce qu'elle venait de dire. Il comprenait la prémisse de base de ce qui s'était passé, mais le raisonnement qu'elle avait dû le déconcerter. "Pourquoi ?! Pourquoi ferais-tu ça ?!" Il a plaidé, la voix légère et désespérée. Elle haussa l... Read full Story
Femboy 2021 2023-02-05 911 Stockings Crossdresser Shemale Fucks Guy Big Cock Lingerie Guy Fucks Shemale
50%
MA MAÎTRESSE MIRACLE
Sam tapota nerveusement ses doigts contre le verre à moitié plein. En règle générale, vous êtes censé boire un coup avec une gorgée, mais sa tolérance à l'alcool n'était pas exactement la meilleure et le bourbon dans la tasse servait vraiment plus de courage liquide à ce stade. Cela faisait ... Read full Story
Femboy 2021 2023-02-05 875 Stockings domination Sex Toys Futanari Ass to Mouth cum in mouth shemale + shemale
50%
UNE FAVEUR INOFFENSIVE
Cela a commencé comme une faveur inoffensive; Je n'avais aucune idée que cela changerait toutes nos vies. La colocataire de ma femme à l'université et son mari avaient emménagé dans notre communauté et dominaient bientôt notre vie sociale. Nous étions à peine sortis de l'université de... Read full Story
Femboy 2021 2023-02-07 764 Stockings Crossdresser Fetish Shemale and Girl domination Guy Fucks Shemale
100%
FUTA UNIVERSITY BOY-JOUET
L'interphone du bureau de Jane Johnson bourdonna. "Oui, Mary," dit Jane. "Il y a une Mme Winter ici pour vous voir madame." Marie a répondu. "Par tous les moyens, envoyez-la directement." dit joyeusement Jane. La porte du bureau du principal a été ouverte par ... Read full Story
Femboy 2021 2023-02-10 820 Stockings Big Cock Lingerie domination Futanari cum in mouth shemale + shemale
50%
IODE VIOLET ⚧️
Meranda avait fait partie du projet militaire d'Athéna. Elle était, très grande pour une femme, environ six trois. Elle se réveillait toujours à six heures sans problème. Ensuite, elle faisait ses cent pompes. Malgré son conditionnement, elle avait toujours une taille de poitrine substantielle q... Read full Story
Femboy 2021 2023-02-11 742 Teen (18+) Crossdresser Fetish Futanari cum in mouth shemale + shemale
50%
LA CUPIDITÉ DE LA MÈRE ⚧️
Nicholas a sorti son téléphone et a pris une dernière photo de sa maison. Nicolas emménageait dans une nouvelle maison aujourd'hui. Nicholas était un garçon de 18 ans, il était le plus petit et le plus maigre de l'école, il gardait ses longs cheveux blonds. Il n'était pas bon en sport et n'a jamais ... Read full Story
Femboy 2021 2023-02-16 725 Stockings Crossdresser Cumshot Fetish Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys