Sort by
Relevancy

Free Stories

73%
My first experience with a tranny
ENGLISH: I want to tell you about my first sexual experience with a transsexual in 2018. I was a bit drunk and got horny, I searched the internet and found a brunette tranny with 7 inches of cock, wavy hair, young and attractive. She had an HIV negative health card. We went to the motel and I was... Read full Story
cuchillo 2020-08-28 7,461 Amateur Cumshot Latina Shemale Fucks Guy Blowjob Big Cock Lingerie cum in mouth brunette ts fingers cocksuck
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 5,064 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,715 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
100%
Being Shemale Part II
After sometime the driver left. Night Two I was again ready by 10 Pm as usual wearing make up and sexy night outfit. My push up bra helped my breast look very attractive looked perfect with my slim body I was standing as usual in the balcony around 11 PM and the driver stopped by again.... Read full Story
babydriver 2024-06-04 2,492 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy Lingerie domination small cock big ass Frottage sissy femboy
29%
Me
I cum here to lopk at all the beautiful shemales I can find. Damn, theres 1,000s I want to wank or enjoy to. Theres not just one kind I want to fondle and cuddle with. But too many to see all. How to choose? Gotta be a trans, transgender, ladyboy, shemale.... Have some tits baby. Large cock is al... Read full Story
Str8guy4u 2019-11-22 4,425 Big Tits Latina Shemale Fucks Guy Blowjob blonde Big Cock Ladyboy masturbating Mature Vintage shemale + shemale Date hot fun 1st timer
81%
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 9,452 Latina Bareback Shemale Fucks Guy Big Cock
42%
First time with a Shemale
I have been curious about shemale's/tranny's for a while now. I finally met one in my small hometown I live in. She was ebony and had beautiful big fake breast and she was so Hot 🔥🔥🔥 and beautiful. We went to her place and she sucked my dick so fucking good and let me beat out her right ass twi... Read full Story
TrannyWarrior 2023-08-30 6,731 first time Fetish Ebony femboy ebony shemale Sexy black trannny
41%
My first date with a "shemale"
I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... Read full Story
bmogotti 2020-03-09 13,100 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
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 22,226 Amateur Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Homemade cum in mouth
100%
Fooled Into Love by a Beautiful Transexual
A fictional, steamy love story about a Man’s first experience with a Shemale... a real take charge kinda girl! Maria Lopez was an absolutely stunning 23 yr old Puerto Rican Goddess. I remember the first time I laid eyes on her, bent over inside her hatchback Toyota, pulling out a hanging fern pla... Read full Story
Oobatz 2018-07-24 12,650 Small Tits Amateur Cumshot Bareback Shemale Fucks Guy Big Cock domination cum in mouth
100%
She Loves Dirty Talk Too
Sexy TS Girl: Hiii! How are you? Thanks for being my new friend. I have so much love forssz you, my friend. Don't hesitate to like and comment one or two photos of me that you like. We can also chat... Love, love, love you, sexy man. HardRock: I really enjoyed looking at your galleries.... Read full Story
Hardrock51Fifty 2024-05-17 3,328 anal Amateur Cumshot Creampie Shemale Fucks Guy Blowjob Big Cock domination Guy Fucks Shemale Ass to Mouth cum in mouth dirty talk
100%
The Game 2
That next morning again Ada and I went down for breakfast and the table was smaller, It wasn't as grand as it had once been and to every guy at the table was now at least two girls. We had our normal breakfast and for once there seemed to be a little more chat between everyone, I think after bei... Read full Story
chris1989r 2022-01-24 4,456 Amateur Cumshot Bareback Shemale Fucks Guy Blowjob blonde Big Cock Asian domination Guy Fucks Shemale Ass to Mouth cum in mouth shemale + 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 31,719 first time Creampie Shemale Fucks Guy ass licking virgin
93%
My First Girly Cock
It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. ... Read full Story
shemale lover 2015-02-27 5,657 tranny Cumshot Shemale Fucks Guy ass fucking Guy Fucks Shemale
89%
My first shemale experience
So before I was even into the porn I had my first experience. I was 25 years old and never thought about anything like this till it happened. I was out with my friends one night hitting the usual bars on the weekend when this hot young woman caught my eye. I was feeling pretty brave due to my "... Read full Story
Duke04 2017-03-28 53,205 first time Amateur Cumshot Shemale Fucks Guy hot shemale
33%
My new Experience with Amy Cute Shemale in Pune
Hi friends i am back with new story. I am mad shemale lover. and keep on finding new shemales for me. This time i got new website to search for shemale www.massagerepublic.com I saw an advertisement of Amy and i liked her. called her and fixed appointment. went to her hotel, which was ok ok ... Read full Story
Stud4Shemale 2021-02-20 6,151 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale shemale fucks man man-fucking-shemale Indian Shemale Pune
87%
Encounter with a dominant shemale
One night I was feeling really horny. I just came back from the gym and I wanted to release and relax. I then began my search for some fun on the personal ads section. I have always been into shemales especially verse aggressive ones. I found this one particular post about Asian bottoms. I was c... Read full Story
SecretAznMan 2013-06-28 47,993 Cumshot Shemale Fucks Guy Big Cock Lingerie ass fucking ass licking big boobs
50%
mi primer scort shemale
Hola me llamo Antonio, por mucho tiempo tuve la curiosidad de experimentar el sexo con una shemale, asi que me di la tarea de cumplirme y quitarme esa curiosidad. Busque una pagina de scorts muy conocida aqui en mexico, una shemale que me gustara; y que creen la encontre. El siguiente fin de sema... Read full Story
discreto28 2018-11-15 4,563 Shemale Fucks Guy Big Cock Lingerie cum in mouth
100%
Shemale sex on a beach
Had to tell you what happened to me recently. I wrote to one of my favourite shemales last week and was telling her I missed sucking and fucking with her due to the current virus situ. Wished I could travel to see her and have some fun and she told me she was away from home too. I asked her where an... Read full Story
xanykeyx 2020-05-07 6,129 suck Outdoor Shemale Fucks Guy shemale cum fuck orgasm Guy Fucks Shemale sex climax deep beach sex
92%
Shemale sex on a beach
Had to tell you what happened to me recently. I wrote to one of my favourite shemales last week and was telling her I missed sucking and fucking with her due to the current virus situ. Wished I could travel to see her and have some fun and she told me she was away from home too. I asked her where an... Read full Story
xanykeyx 2020-05-07 8,762 suck Outdoor Shemale Fucks Guy shemale cum fuck orgasm Guy Fucks Shemale sex climax deep beach sex
100%
Loosing my virginity to Shemale Preet
This story is of may be 2017. When a shemale escort took my virginity n fucked me. I am not new to shemales. I hv been attracted to shemales since 1999 when first time I got internet at home. Suddenly while browsing i saw shemale website n instantly i was hooked to it. Well how I met my first ... Read full Story
Stud4Shemale 2021-02-20 8,032 Bareback Shemale Fucks Guy shemale fucks male first time with a tranny Indian Shemale Pune Sucking Shemale Cock Loosing virginity to shemale
50%
Me & Jo Shemale
Yesterday Jo Shemale and I went for on a pussy hunting fall walk. Well, I did, I'm pretty sure Jo Shemale wasn't hunting pussy. It was getting colder, so we had to put on our woolly panties and sweaters. Halfway down the block, we saw the Old Fuck's out in their yard. The Old Fuck's were raking b... Read full Story
shemale lover 2011-08-16 4,611 cock suck shemale
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 13,290 first time Creampie Shemale Fucks Guy
100%
1st time with Thai shemale
So after months of crosssdressing , camming and phone sex i finally decided to have a meet. I found a lovely Thai shemale on birchplace and went to see her in London. She was gorgeous and put me at ease straight away. After a few minutes of massage she started licking and sucking my nipples, then as... Read full Story
Nutcracker29 2013-04-09 9,266 first time suck Shemale Fucks Guy Asian big boobs
100%
Bareback fuck by Lysa Shemale
Well I am devoted shemale lover and have met many shemales in my life. This incident is of probably December. I called my shemale escort Amy to meet and some how she was not picking call. Then around 4.30 pm she picked n told me that she is having hangover due to party so was sleeping, so I sh... Read full Story
Stud4Shemale 2021-02-20 7,235 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob cum in mouth barebackedshemales shemale fucks male cum in ass Indian Shemale Pune
100%
The Big Mature Shemale Next Door
The Big Mature Shemale Next Door SugarandSalt "Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mir... Read full Story
Gwapo67 2022-05-03 7,962 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
A Live Shemale Chat Session
I was always curious about Shemales. I was never into dudes at all, but there was something about a hot Shemale that just turned me on. The first time I ever got in touch with a Shemale was when I went to have a live Shemale chat session on a website I found a couple of years ago. I got so scared... Read full Story
shemale lover 2015-12-23 4,117 tits deepthroating dick
69%
Shemale Video Galleries And A Cock To Bang
I arrived in Bangkok one early afternoon and I was ready to experience the thing the place was famous for. As soon as I checked in my hotel and got in my hotel room, I started searching for some hot encounter through shemale video galleries. They were all really pretty and promised a lot of fun. ... Read full Story
shemale lover 2016-04-20 4,249 first time Big Tits shemale
91%
MY FIRST TIME WITH A SHEMALE
I`ve always had this fantasy about being with a shemale,i guess something about a chick wit a dick and tits always turned me on,i`ve always been curious about wat it`s like to be fucked by one.Well last weekend was a weekend i`m gonna remember for the rest of my life bc that was the weekend i decide... Read full Story
shemale lover 2013-06-21 15,043 tranny Cumshot Shemale Fucks Guy Big Cock fingering swallowing
88%
MY FIRST SEX WITH SHEMALE
This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous durin... Read full Story
shemale lover 2013-12-01 40,078 first time anal sex suck Shemale Fucks Guy Guy Fucks Shemale
96%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2014-11-25 10,076 tranny suck Creampie Shemale Fucks Guy ass fucking 69
80%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2014-12-03 6,398 tranny suck Creampie Shemale Fucks Guy ass fucking 69
78%
Once wasn't enough!- my 2nd shemale exp
So after my first experience I got really into the porn I bought movies magezines got on websites just couldn't get enough. But watching it wasn't enough I had the real thing once and wanted it again. It had been almost a year now and only one person knew about what I had done that one fat... Read full Story
Duke04 2017-04-01 10,444 anal sex Shemale Fucks Guy ass fucking Shemale on Guy
56%
Big cock shemale from Pune, India
I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in ... Read full Story
Stud4Shemale 2017-05-22 95,931 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
50%
How Sia Shemale Pune fucked me ...
I met Sia through ts-dating . Called her n went to meet her. When I saw her I could not believe that she is shemale n has got cock between her legs. My god so beautiful feminine. Her implants are very sexy n make her more beautiful... Then I paid her n we went to comfortable small bedroom. I d... Read full Story
Stud4Shemale 2021-02-19 5,698 Shemale Fucks Guy Blowjob Big Cock Asian Ladyboy big boobs cum in mouth shemale fucks male Indian Shemale Pune
62%
Bobbys Preggo Shemale Turn
This is a story about how a 14 year old normal guy became a sexy 16 year old pregnant Shemale. It has many similarities to real events. Bobby was a normal guy. he grew up in a good family and was fairly popular. One day when he was in 9th grade his class recieved a new teacher. Her name was... Read full Story
shemale lover 2011-08-18 4,676 Big Tits shemale submissive
90%
My first shemale sex
I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our ... Read full Story
shemale lover 2013-08-14 94,503 tranny sex toy anal sex suck Shemale Fucks Guy dildo
80%
My Shemale experiences
I have had experiences with Shemales. All in Hawaii. Three different ones. I met them all through yahoo chat when it was still fairly popular. In the 1998-2000 time frame. The first one I met up with was doing video shows in some back area part of Honolulu. She agreed to meet me as long as we only h... Read full Story
trisex69 2015-05-20 6,344 anal Shemale Fucks Guy cum oral
94%
My first Shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe that started my intere... Read full Story
SachinJoy 2018-10-04 32,633 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
92%
Real Story with a Shemale Escort
One day I dreamt about a big black cock fucking me on doggy style. The dream felt so real that it made me to ejaculated in my sleep without even touching my cock. It was the first time this happened to me and I was surprised because I’d never felt gay. My underwear became a mess filling the whole su... Read full Story
GusDark 2023-08-28 7,950 Shemale Fucks Guy Blowjob cum in mouth Handsfree cum real life Cheating wife
68%
Shemale Porn Photo On The Wall Of Her Room
She was a truly hot shemale that I’ve been seeing for a couple of months now, from time to time. She had some really big tits and a dick that didn’t really get in our way much. It really wasn’t all about the sex. I loved talking and even cuddling with that girl. We talked about ... Read full Story
shemale lover 2016-06-12 6,521 asshole shemale Big Cock
100%
How I Used To Cum On Shemale Webcam
I like being a shemale and doing webcam shows. A lot of guys out there would never admit it, but they really like my sort - best of both worlds, so to say: tits, asses and cocks in one convenient package. And shemale webcam was also a lot of fun - I could play with myself as much as I liked and dude... Read full Story
shemale lover 2011-08-10 2,907 anal shemale cum
100%
Shemale Cam Made Me Explode
I really thought it would be just another quick cam session. I logged on to my computer, chose a girl and started talking. But after a while, she told me she's a shemale - then I realized I'm in the shemale cam section. I replied that it's ok - hell, I'm all about trying new things and broadening ho... Read full Story
shemale lover 2011-08-11 3,019 Big Tits cum fingering
0%
The orgy with a shemale
I had to move to Japan back in the fall of 2004 and lived in Tokyo in a 3 room apartment.I could not pay all of the rent so I lived with a female school teacher age 27 years of age and japanese.Her name was Miki.There was a one more girl who was friends with Miki ,I never seen much of her.Her name w... Read full Story
shemale lover 2011-08-29 5,182 Big Tits asshole Big Cock
87%
Wife fucked by shemale
This is the story of me Rittu married to a guy named Harvinder in 1996. We had 2 kids from our marriage .Harvinder was very fond of girls and even before my marriage he use to fuck prostitutes right from young girls to middle aged women. He used to get his cock sucked and even used to fuck these pro... Read full Story
shemale lover 2012-07-30 7,176 sucking shemale fucking
27%
I have been out dune by my little brother by a big difference hi
I am 32 years old and my lady who was 46 and my little brother who was just 14 years old then wanted to have some fun and get my woman who was just the right for him he was just out of his mind about her and I was like I'm all about it and I was thinking that I was going to be the big cock an h... Read full Story
Not long but hard 2017-10-19 5,922 Big Tits gangbang Shemale and Girl Solo Shemale Cartoon shemale + shemale Wow.
100%
Shemale snapped
Camilla took a few steps out the door of her balcony to get a feel for the temperature. Thankfully it was cool out. It had been a hot day, which meant a cool night was welcomed. She closed the door and pulled out a pair of gold hoop earrings. She was suffering from a mild case of the jitters. The... Read full Story
shemale lover 2012-06-21 6,256 anal sex Creampie shemale Big Cock
93%
My first encounter with a shemale!
I am a straight guy who had never strayed before.. however i had been having urges over shemales and started wanking to shemale porn every now an again online. i have always been interested with my ass being explored but i never found men attractive. with shemales it was different. they are beautifu... Read full Story
shemale lover 2012-11-24 7,696 first time sucking shemale facial
71%
White fuckslut Tgirl & 3 BIG BLACK COCKS Initiation
You lucky, slutty BBC Tgirl fuckslut, I envy you soooooo much. This is the most erotic and best BBC story on this web site. Pleeease keep writing about your BBC fantasies. What a bargain to get gangbanged by about 30 big black studs for only 15 Euros. I loved it when you begged them to fuck you.\r\n... Read full Story
TgirlJill4BBC 2013-06-03 6,027 Stockings Cumshot Big Cock gangbang Lingerie Interracial Latex
71%
TGirl Initiation by 3 BIG BLACK 12
In my teen years I was often told that I was quite feminine.The high school punks always told me that I filled out the back of my jeans in a girly way. After taking a shower one day I did notice that they were right, I had a nice white bubble butt. Not to mention that my lips were also quite girly. ... Read full Story
TgirlJill4BBC 2013-06-04 9,071 Stockings Cumshot suck Big Cock Lingerie Interracial Latex
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 1,513 Stockings Shemale Fucks Guy Fetish Futanari 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 7,644 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
50%
J'ai enfin goûté la bonne chère/chair
Dépucelée en bon et du forme... Chose jamais osée depuis que je goûte la jouissance par tous les sens et dans tous ses sens... Je la découvris quand elle m'a sourit en guise de remerciement pour lui avoir cédé le passage dans la superette du bled où j'étais pour affaires. Sandales à ses pieds d... Read full Story
hippocampus_171 2022-11-09 1,069 Small Tits Amateur Shemale Fucks Guy Guy Fucks Shemale Mature Homemade Ass to Mouth Vintage cum in mouth
50%
Pa-mie sex-agénaire
Luxure frénétique d’une pa-mie sex-agénaire; entre rêve et réalité Je n’avais jamais fantasmé de mec viril, même après avoir offert ma virginité; mais à une fabuleuse sissy. Avant mon Ѐre, mes préférences de fantasmes étaient toujours avec des lui-femme glabres, idem concernant mes relations d’aprè... Read full Story
hippocampus_171 2023-07-09 850 anal Amateur Group Sex Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy Ass to Mouth
100%
Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
Chrissy Tunnell 2022-02-03 3,613 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
UN RENDEZ-VOUS ROMANTIQUE ⚧️⚧️⚧️
Alex mordilla sa lèvre en fixant le test d'anatomie devant lui. Après une semaine épuisante de finales et de sessions d'étude nocturnes, c'était enfin son dernier test. La liberté était si proche qu'il pouvait presque y goûter. Sa jambe rebondit anxieusement alors qu'il remplissait une autre série d... Read full Story
Femboy 2021 2023-02-17 1,038 Big Tits Cumshot Fetish Blowjob Big Cock Guy Fucks Shemale Futanari cum in mouth