Sort by
Relevancy

Free Stories

100%
My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts :) I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use the ... Read full Story
shemale lover 2014-08-25 9,434 sucking shemale teasing
93%
My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts :) I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use t... Read full Story
shemale lover 2015-01-19 6,271 blonde Big Cock Shemale and Girl
82%
Shemale cum in my pussy
Being a girl and only fucking me, I wondered what it was like to be with another girl. I am attracted to girls but the problem is that I really like the way that a cock makes me feel, especially when it fills my pussy with cum! The bigger the better! While sharing this dilemma with a friend she sugg... Read full Story
shemale lover 2015-06-29 14,357 cum oral dick
78%
My Shemale Stepmother Part 2
"Not yet, bitch. You've got to beg for it first," she slapped my face with her semi hard cock, "Now, tell me what you want." "I want your cock, mistress," I said wimpily. "What do you want to do with it, slave," she slapped her cock across my cheek again... Read full Story
shemale lover 2011-09-01 11,309 Cumshot asshole licking sucking
50%
Spy Girl
Vicki stood in the dark doorway as she watched her mark, Ivan Patrinkov, approach up the empty street. There was no way he would be able to see her where she stood in the shadows. She wore a skin tight leather jumpsuit with black low-heel boots. She would have preferred to have on a pair of stiletto... Read full Story
shemale lover 2011-11-09 4,710 anal sex shemale Frottage
100%
Fulfilling A Girl's Male Fantasy
"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up so she invited me back to her place. It turned out that she was eighteen and still living at ho... Read full Story
shemale lover 2012-04-04 3,716 orgasm fingering oral sex Sex Toys
100%
Shemale on wheels tour
Being a sexy naughty city girl like myself…I get allot of attention from the boys. I always enjoy getting the attention of the small town boys that are not used to seeing a sexy bitch like me roll though town. They jerk off to girls like me online all the time. But having me right in front of... Read full Story
shemale lover 2012-05-17 3,563 anal sex fingering domination oral sex facefucking
100%
Female Seduces a Shemale
As you are sitting in your computer chair , chatting online, I walk up behind you and softly massage your arms. I lean around and kiss you on the cheek. You turn your head to see who it is and I kiss you full on the lips. I walk around your chair and sit on your lap facing you, teasing you. I wink a... Read full Story
shemale lover 2012-07-06 2,790 Cumshot Blowjob Shemale and Girl cum swallowing handjob
0%
A Working Sissy Girl
I look up at my boots. Cute! Received delivery just day before yesterday, my boy friend hasn't even seen them yet. He'll like them, know he will. 3" spike heel ankle boots, very shiny patent leather, I look up at the one on my right foot. I run my hand down the thigh-high lace top seamed nylon ... Read full Story
shemale lover 2012-07-29 3,784 Cumshot oral sex sissy
94%
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 2013-07-17 7,933 tranny sex Stockings oral sex kissing shemale sex
93%
My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts. I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use the... Read full Story
shemale lover 2013-07-20 3,840 Cumshot Shemale and Girl big boobs handjob kissing
83%
MY FIRST TIME WITH A SHEMALE - 2
DEAR READERS I DON’T KNOW IF YOU LIKED MY FIRST STORY AS THERE WERE NO COMMENTS ........ !!! After we finished our late dinner in the very cosy position she whispered “wanna have some wine honey?” I replied “I’d love to”. She got up leaving me sitting on her bed and poured two large glass-full of... Read full Story
Lisawantsu7 2014-09-02 6,579 hardcore Creampie Big Cock ass fucking Shemale and Girl
88%
Shemale Ride Along Part 2
Note: This is a sequel to my previous story, "Riding in Cars with Shemales." If you would like some back story into how Terra and Matt met, please read it. If not, you can probably still enjoy this one by itself. * It was a wonderful day in May. The sun was shining. The sky was clea... Read full Story
qtball 2016-08-31 11,546 Outdoor Big Cock bj Shemale on Guy self fuck
81%
That night....
I was extremely nervous when I pulled out my phone and dialed the number. Never before, in my wildest dreams, had I thought I would act on one of my strongest fantasies. I knew I would be nervous when I first met her, but after exchanging pictures and seeing that big, fat cock of hers, I knew I ha... Read full Story
bigTHICKY 2017-05-08 9,303 Big Tits Cumshot Latina Big Cock Ladyboy cum in mouth
91%
The Beginning Of Penny
This story is about how I became Penny, the cock loving, tranny. I remember being a kid and jerking off to dirty mags we stole from my friend’s dad. The pics that always made me hottest were the ones in the ads in the back few pages for phone sex with trannies. Looking at those hot and perfect women... Read full Story
pennypenny 2017-05-29 10,560 Crossdresser Blowjob Guy Fucks Shemale 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 3,804 Crossdresser Masturbation Blowjob Lingerie Mature cum in mouth
100%
TG affair in Bimini
The day was rainy and weather was dreary, not much to do and have the day off. I fly a charter plane that takes people to and from the Bahamas from Ft Lauderdale. My girlfriend Jan and I only stay together a few days a week, she is in Real Estate and with my schedule we have not been together in t... Read full Story
Jon Paul 2021-04-19 3,300 Teen (18+) Bareback Creampie Blowjob Guy Fucks Shemale
100%
The Dating Game
This happened a few years ago when i had just been accepted into Edinburgh University to undertake my Masters. As all students do, I went to the tourist spots with an eye on the other tourists and potential bars to frequent. Having come prepared with an arsenal of dating apps downloaded I was all s... Read full Story
chris1989r 2021-08-11 6,649 Amateur Bareback Big Cock domination Ass to Mouth cum in mouth
100%
Deflowering Latina Sissy Destiny
A real life story of my one and only time deflowering someone and being their first real encounter, I was 27 at the time and she was 21. I am absolutely convinced that Trans girls and CDs have a bit of a 6th sense when it comes to perceiving which guys are into them even in a public situation. I ... Read full Story
AllenB 2022-09-07 6,325 first time Big Cock Guy Fucks Shemale Homemade sissy travesti cum in mouth
88%
Surprise Ending (Part Two)
My curiosity, unconscious urges, and my horniness pushed me into action. I gently cradled Karla's balls in my left hand while my right hand settled on her taut ass. I caressed both and then let my left hand move on to her now blood engorged shecock. I am a pretty big dude, but I could hardly get ... Read full Story
Chantel13 2022-08-23 4,417 Crossdresser Amateur Group Sex Outdoor Big Cock Shemale and Girl redhead cum in mouth
100%
Been a while and oops!!
Hi been a while since I let you know what’s going on with me. Well after spending the last couple of months getting on with stuff and trying to behave ( boring) I finally snapped and needed to go to the woods for some well deserved dick!! I got myself dressed up as normal, g string , stockings, ski... Read full Story
Samantha Jewels 2022-12-10 3,383 Crossdresser Outdoor Bareback 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 7,918 Shemale Fucks Guy Blowjob cum in mouth Handsfree cum real life Cheating wife
100%
Vegas Encounter- Part trois
This was to be Jack’s second night in Las Vegas, he had met his online pen pal Diane, and her roommate Holli, the previous day and the three hit it off with an evening of sex. Jack had spent the day getting to know Holli, and the day proved to be unbelievable. Holli and Jack took a drive into the mo... Read full Story
Jon Paul 2023-12-24 6,051 anal Cumshot Bareback Creampie Guy Fucks Shemale cum in mouth
100%
Regina's Vagina dreams
I think I wanted to be a female from birth. I once looked through a girlie magazine out of curiosity. I had impossible dreams and I longed to trade genitalia with them. I have always fantasized about my Vagina when I was younger. It was during those times that I would drift into my own private world... Read full Story
Regina10 2024-03-01 5,362 anal Big Tits Bareback Creampie Blowjob Big Cock Ebony gangbang Guy Fucks Shemale big ass cum in mouth double anal
85%
My first time with a shemale escort
This story that was posted at the forum today by our new member got me hard as hell. He writes about his first experience with a tgirl and i can't be more positive that most of us would like to experience this too. Enjoy reading... I recently had my first experience with a shemale. Here's how it ... Read full Story
shemale lover 2011-06-30 178,059 anal cum dildo
80%
Car sex with a shemale at the local drive in
I know for sure many guys are fascinated about fucking a shemale in a car. Well, this is what the story is about. The guy rammed shemale ass at the drive in. Happy reading! I pulled in with my radio up and saw the most beautiful girl walking right in front of my car. Her legs were long and brown ... Read full Story
shemale lover 2015-08-01 8,871 cock shemale fucking
100%
Foot Massage by a Shemale
My wife and I had just finished a nice Sushi dinner in an upscale restaurant outside of LA, with an old college friend of hers. We strolled down the boardwalk and were almost past an asian style massage spa, when my wife said why don’t we take advantage of their 45 minute foot massage for $... Read full Story
shemale lover 2018-05-12 12,703 sucking shemale cum
94%
New Girl in Town
Margo sat next to me in the coffee shop late that Saturday afternoon. His real name was Mark, but he was one of the loveliest Drag Queens in New York City. I had been dressing secretly at home in my mother’s and sister’s clothes for just over three years, but at 18 years old, I had never... Read full Story
shemale lover 2019-06-04 10,036 anal shemale oral sex
84%
Fucked by a Shemale
My names - and I would like to tell you about a very sexual experience I had recently. First I would like to tell you I’m 30 years old and never had a gay experience, until now. It was a Saturday night, me and my brother were round the local town, after a few too many beers my brother met a bi... Read full Story
shemale lover 2011-08-18 169,228 first time shemale cum
87%
Shemale First Time
First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married... Read full Story
shemale lover 2011-08-24 9,229 first time asshole shemale
100%
by a Shemale Part 2
I was awaken early Monday morning when Felicia lightly kissed me on the cheeks and said it was time to start my hormone regimen. I looked at her and she had her left hand opened and she had a white pill and in her right hand a glass of water. I was no longer fighting or resisting especiall... Read full Story
shemale lover 2011-08-29 6,015 anal sex sucking shemale
100%
A Job in the Theatre Chapter 7
The next day Paula woke late in the day. She lay in bed feeling the glow from her bottom. It was totally erotic and the most satisfying sexual experiences she had ever had. The more she thought about it the hornier she became. She grabbed her cock immediately focused on how much smaller it was th... Read full Story
shemale lover 2012-03-13 2,679 Stockings cum oral sex
100%
Fulfilling A Girl's Male Fantasy Part 2
Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a ... Read full Story
shemale lover 2012-04-04 4,378 Stockings anal sex Group Sex Blowjob
100%
Party Surprise - First sex as a Crossdresser
This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly s... Read full Story
shemale lover 2012-05-21 7,458 first time hardcore anal sex Cumshot oral sex crossdressing
100%
Crissie Fucks the Neighbor
It was a Saturday afternoon and I was all alone in the apartment as my roommate Kelly had gone home to visit her mother for the weekend. I hadn't had a date or been more importantly been laid in several weeks. Needless to say I was very horny. I quickly flipped through the TV channels and as usual... Read full Story
shemale lover 2012-06-07 3,942 anal sex Creampie oral sex facefucking
92%
T-Girl Meets T-Girl
It was a silent car ride home. He looked at her, she looked out the window. She looked at him, his eyes were on the road. Neither of them broke the silence. It stayed that way until he parked in her mom's driveway. The soft-spoken young man told his girlfriend, "Goodnight Ashley. I'll call y... Read full Story
shemale lover 2012-08-29 6,163 anal sex Cumshot shemale and shemale domination blondie
87%
My way to shemale sex
It all started with porn. 10 years ago, i was watching porn on my bed, jerking off watching a girl sucking a big cock. I looked at my cock and started wondering what that beautiful peace of meat tasted like. After a few moments of hesitation, my curiosity took over and i put my back against the wall... Read full Story
andre_xp_8 2018-07-24 13,718 anal Blowjob shemale first time
100%
Intense
Holding to my word, I didn't let the incident with Billy and his friends scare me away from Bailey; I kept seeing her, even after the beating I took. To be honest, I'm not sure if he was trying to lay low or what, but Billy seemed to keep his distance from me for a while...thankfully. Bailey and ... Read full Story
Verpa 2019-10-21 10,762 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Big Cock cum in mouth
100%
First Time I Experienced Eating a Tgirl Out
So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... Read full Story
AllenB 2022-10-21 5,109 Amateur Big Tits Cumshot Latina Creampie Fetish Blowjob rimming Homemade cum in mouth latina ts
100%
Whoops, I fucked my bosses son! Real story, written by a tgirl
Normally I never would have entertained the idea of sleeping with a co-worker but when I saw my boss’s son for the first time, that idea quickly went out the window. It wasn't like I didn't think about fucking my co-workers, I did… in fact, I would leave work some days leaking with precum from the v... Read full Story
Madison Heights 2022-10-27 6,861 Bareback Blowjob shemale Big Cock Uniform Lingerie tgirl office sex cum in mouth coworker creampied workplace
80%
Outdoor Tranny Sluts Lust
I wake up really early one morning with my cock throbbing hard under the sheets. I got a white camisole on. Out of bed i go with a desire to vouyer and masturbate somewhere around my home. I'm home alone so i head out to my garden with my cock bouncing up, down & dripping cum. It's about 5am... Read full Story
Tracy Bel 2023-02-14 5,499 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
38%
From Gloryhole Peegasm to Shemale
I was in a porn video booth. I young guy stepped into the next one. I was already jerking my small dick, but he didn't even pull his pants down. He asked me if I wanted my dick sucked. Actually I think he said something like, "hey, let me suck your dick." Recently I had let some weird, ... Read full Story
shemale lover 2011-08-18 16,430 asshole shemale jerking off
71%
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 2012-03-16 2,844 cum oral sex swallowing
100%
Shemale Fantasy
My fantasy is to be taken by a shemale. I have been workingat this boutique for about three months. I sometimes work the same shift with this very attractive young lady who is tall with a knock out shape. Her breasts look absolutely luscious as she dresses very provocative at times. I find myself... Read full Story
shemale lover 2012-05-02 2,644 orgasm oral sex rimming
100%
Female Seduces Shemale Chapter 2
I wake up to your soft kisses on my throat. I open my eyes to see you fully nude laying over top of me with your hands on both sides of my chest holding yourself up. You look down and smile at me seductively. You lean down for a kiss. I feel your hot tongue parting my lips. I open my mouth slightly ... Read full Story
shemale lover 2012-07-07 2,659 anal sex Creampie fingering Shemale and Girl facefucking
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 8,730 first time ass shemale Big Cock feet
83%
Dressing with my cousin
My First Time When I was about 16, I would spend my Summer vacations, from school, at my Uncles’ house. My cousin and I would sleep in one bedroom, with two beds. He was three years older then me and always knew what we could do, to have fun. I looked up to him and wanted to be like him. We had... Read full Story
Topazsteve 2018-01-04 13,662 Stockings Teen (18+) Crossdresser Blowjob Lingerie cum in mouth
87%
Chance Encounter 4/7
With her feet still pointed she starts slowly spreading and rubbing her cream over her nipples while i’m thrusting my cock in and out of her sweet hole. Her hole felt so beautiful! In and out I thrusted until I pulled out. I grabbed her hands, lifted her a little and pulled her towards me as I stood... Read full Story
Katlick 2019-10-30 5,065 Bareback Creampie Big Cock cum in mouth
100%
The Seductive Seed of a Tranny MILF
The Seductive Seed of a Tranny MILF SugarandSalt Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spo... Read full Story
Gwapo67 2022-05-03 7,774 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
50%
Miranda Fucked me & feed me her sweet cum
This is absolutely true story. I am shemale fan & crazy for shemale since many years. But recently in last few years hiring shemale is so expensive in india. Their charges went up sky rockt. But i was looking for some genuine & friendly encounter. I was searching for trans or shemales on PR dati... Read full Story
Stud4Shemale 2023-09-25 4,278 shemale virgin cum in mouth bareback fuck shecock shemale cum Indian Shemale Desi Shemale Shemale fuck men Pune Shemale Man fuck Shemale shemale cum eater Bangalore shemale
50%
Miranda Fucked me & feed me her sweet cum
This is absolutely true story. I am shemale fan & crazy for shemale since many years. But recently in last few years hiring shemale is so expensive in india. Their charges went up sky rockt. But i was looking for some genuine & friendly encounter. I was searching for trans or shemales on PR dati... Read full Story
Stud4Shemale 2023-09-25 4,111 shemale virgin cum in mouth bareback fuck shecock shemale cum Indian Shemale Desi Shemale Shemale fuck men Pune Shemale Man fuck Shemale shemale cum eater Bangalore shemale
50%
Miranda Fucked me & feed me her sweet cum
This is absolutely true story. I am shemale fan & crazy for shemale since many years. But recently in last few years hiring shemale is so expensive in india. Their charges went up sky rockt. But i was looking for some genuine & friendly encounter. I was searching for trans or shemales on PR dati... Read full Story
Stud4Shemale 2023-09-25 4,354 shemale virgin cum in mouth bareback fuck shecock shemale cum Indian Shemale Desi Shemale Shemale fuck men Pune Shemale Man fuck Shemale shemale cum eater Bangalore shemale
50%
Miranda Fucked me & feed me her sweet cum
This is absolutely true story. I am shemale fan & crazy for shemale since many years. But recently in last few years hiring shemale is so expensive in india. Their charges went up sky rockt. But i was looking for some genuine & friendly encounter. I was searching for trans or shemales on PR dati... Read full Story
Stud4Shemale 2023-09-26 4,292 shemale virgin cum in mouth bareback fuck shecock shemale cum Indian Shemale Desi Shemale Shemale fuck men Pune Shemale Man fuck Shemale shemale cum eater Bangalore shemale
100%
Miranda Fucked me & feed me her sweet cum
This is absolutely true story. I am shemale fan & crazy for shemale since many years. But recently in last few years hiring shemale is so expensive in india. Their charges went up sky rockt. But i was looking for some genuine & friendly encounter. I was searching for trans or shemales on PR dati... Read full Story
Stud4Shemale 2023-09-26 5,536 shemale virgin cum in mouth bareback fuck shecock shemale cum Indian Shemale Desi Shemale Shemale fuck men Pune Shemale Man fuck Shemale shemale cum eater Bangalore shemale
100%
A man & Two Hung Shemales meet in Art Gallery o
I spent a week of absolute extreme erotic ecstasy with Stan. I used his throat and ass multiple times a day. He also fucked and fisted my ass as well. It is a week of total decadence debauchery and depravity. In the late afternoon, Stan and I decide to visit a local art exhibit so we can get out ... Read full Story
darrell 2024-02-02 5,227 anal Cumshot Big Cock Frottage deepthroat shemale + shemale swallow cum
100%
In the bus
Everything can happen in a bus, you are going to read something that happened in real life and it’s for you to choose whether you believe it or not. I was looking forward to meeting her in the bus. I’d changed my working schedule since the first time I saw her. I did everything just t... Read full Story
shemale lover 2014-06-03 7,482 shemale cum