Sort by
Relevancy

Free Stories

81%
Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
shemale lover 2015-02-27 6,928 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
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 5,751 Big Tits Bareback Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
100%
Lola Chapter 4
We sat at the table. I had made the effort to cook a small three-course French-inspired dinner. I was in love, but Lola’s mind seemed elsewhere. - How nice… She was chewing absent-mindedly. - I have to ask you something. - Shoot baby. Ask away! Lola looked deep into my eyes: - Could you ima... Read full Story
BellaBeau 2023-10-30 5,561 anal Cumshot Latina Bareback Creampie Shemale Fucks Guy Frottage Homemade Lola
100%
The Massage
The Massage One afternoon I decided to get myself a massage, a deep tissue one as really needed it. I had asked a friend of mine to recommend a masseuse and she said she would make an appointment with her friend, Pat who was a masseuse. I arrived for my appointment and was greeted by a very cute ... Read full Story
Lacetoface 2024-05-13 3,235 anal Shemale Fucks Guy
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 33,160 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
91%
Southern Hospitality Ch. 02
XtinaSmith2017 Laura felt herself lifted lazily from the arms of sleep, her body relaxed and floating on a small cloud of pleasure, her mind filled with images, sensations, not pulled from whatever dream she had just been having but instead, memories, memories from the night before. Memories of... Read full Story
Gwapo67 2022-05-16 4,544 Bareback Creampie Shemale Fucks Guy Big Cock Mature
100%
I fucked my personal trainers ass for the first time
I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... Read full Story
Madison Heights 2023-05-18 6,852 anal Shemale Fucks Guy Big Cock Frottage
90%
My Tgirl lover
This is my first attempt at writing one off these stories so if you like it than please let me know and I'll look into writing another one also any feedback would be welcome My names Phil, I'm 28 and I currently live with my girlfriend with whom I've been dating for several years. U... Read full Story
Maillihp 2017-05-15 9,328 Bareback Shemale Fucks Guy Big Cock
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 16,680 Shemale Fucks Guy Blowjob Ebony Interracial
94%
Flight cancelled
I was on my way back from a long business trip to Chattanooga, Tennessee and deciding to hit the airport bar during my layover. As I walked up to the bar I noticed there was only one seat open. I took it. I ordered my favorite drink, an old fashioned neat with makers mark. As I sat there waiting for... Read full Story
Jsmithsub 2019-10-31 24,243 big dick Group Sex Bareback Shemale Fucks Guy Fetish Blowjob Big Cock pissing Ebony domination cum in mouth monster cock gang bang
100%
Return to Luisa Tavares
Everyone at the office asked my why I was limping. I told them I had fallen playing tennis. The truth was, I had been mercilessly fucked by Luisa Tavares. Her huge cock had destroyed my asshole. Can you imagine someone thrusting a can of Coca Cola up your butt again and again with tremendous forc... Read full Story
hotspur 2020-04-14 15,477 Bareback Shemale Fucks Guy Blowjob Big Cock Shemale and Girl cum in mouth
100%
Got my ass pounded in Miami by a tranny escort
Got my ass pounded in Miami by a beautiful tranny escort with a 10 inch thick cock. Years ago I was in Miami for a business trip. Four days just me in my hotel room. I decided to treat myself to some of the X rated channels that my hotel provided. As usual I went straight to the tranny porn.... Read full Story
My Shemale Attraction 2023-01-03 6,645 Amateur Big Tits Masturbation Creampie Shemale Fucks Guy Blowjob
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,393 Crossdresser hardcore ass fucking cd
89%
Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2016-11-14 17,901 big dick anal sex suck Blowjob cock sucking workplace
100%
About Jack and Diane
Thanksgiving was over the college kids are returning to school and Las Vegas has slowed down from the busy restaurants and overcrowded casinos. It’s the best time of year to see a nice show for less. Jack’s friends had all taken off with families and he had time to think about how lonely he really w... Read full Story
Jon Paul 2023-12-20 6,603 anal Cumshot Bareback Fetish threesome Lingerie Guy Fucks Shemale small cock shemale fucks shemale cum in mouth shemale + shemale
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 2011-08-18 168,961 first time shemale cum
100%
A Shemale Vacation Part 2
We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragem... Read full Story
shemale lover 2011-09-05 7,032 anal cumming cum swallowing
100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 5,190 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 13,729 Masturbation cum orgasm cumshots prostate
100%
Late for Work
She was dressed only in her plain white cotton bra and a skirt when he called her for breakfast. She was frustrated she could not find her favorite blouse and rubbed at the dark circles under her eyes. Picking through the massive pile of clothing she found a gray tank top with a stain on one sid... Read full Story
shemale lover 2013-02-06 5,927 sucking jerking domination Guy Fucks Shemale big boobs
100%
Casino Girl
I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... Read full Story
Jon Paul 2022-01-03 2,823 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
100%
Male or Shemale, Still a Slut
Part 1 My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond ... Read full Story
shemale lover 2012-12-20 9,216 Cumshot sucking blonde ass fucking Guy Fucks Shemale
50%
DATES NUITS
My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... Read full Story
Femboy 2021 2023-02-07 1,249 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial Sex Toys 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 3,543 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
Duality
John and I have been together for about 7 years now. We met at high school during what was the worst time of my life. I had a terribly traumatic childhood as my body developed into womanhood despite being born a boy. As my confusion and depression worsened, my family were incredibly supportive an... Read full Story
shemale lover 2012-12-02 3,717 sucking shemale orgasm
100%
Christy's Fantasy Come True Chapter 6
The alarm went off and Christy rolled over and hit the off button. The clock face was starting back at her flashing 8:00. Since it was Friday she had slept in a bit. Jim had gotten up early and left for work after spending the night. They had gotten into a minor argument last night but came to a... Read full Story
shemale lover 2013-01-30 5,045 anal sex Cumshot Masturbation Blowjob Guy Fucks 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 7,487 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 30,756 strapon porn
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 22,676 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 11,738 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
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 11,263 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 4,796 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
100%
Am I Who I Think I Am? Chapter 2
Well,I can't lay here all day and dream! I feel so good, so loved, so ravished. My smile is touching the pillow on both sides! I'm laying here daydreaming about my deflowering this morning. Inside me lives my lover's DNA, looking for a life to create. (Nice try little spermies, but you won't find it... Read full Story
shemale lover 2012-10-19 3,463 Cumshot sucking Fetish
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,182 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
100%
Florida TG Experience
I had known Jan from High School, we always had an attraction for each other but were dating someone else or married at the time. Jan had actually married a friend of mine and I was envious of course. She at that time had sandy blonde hair, and a body to die for. One evening we had them over for dr... Read full Story
Jon Paul 2018-08-13 10,815 Group Sex Big Tits Bareback Creampie Blowjob blonde Asian Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,554 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 5,371 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
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 4,633 hardcore shemale fuck
100%
Mongoose Hunting and the Dark Car
After my first sexual experience with a trans girl in school (Check out Biology of Music), it was a long time before anything else got me that horny again. Which is obviously understandable given how ridiculous that whole event was. This time instead of a trans girl cumming hot jizz into my mouth af... Read full Story
terrifictim 2023-03-30 5,483 Teen (18+) Cumshot Bareback Creampie Guy Fucks Shemale rimming rimjob Ass to Mouth cum in mouth Surprise secret bathroom sex Daddy daughter risky public
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 11,369 Bareback cum ass fucking slave
90%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 19,243 Big Tits sucking ass licking fucking
92%
Issy used by black men
About a year ago while living in a hotel and living there as a Transexual I was used by a young black man as his whore for the night. He moved in about two weeks ago with a couple friends. They where maybe 5 rooms away from me on 1st floor. As the week wore on I would be coimg and going and would... Read full Story
shemale lover 2013-06-26 4,934 sex toy anal sex Cumshot suck Big Cock Guy Fucks Shemale
92%
The Girl Next Door Ch. 02 by derezzed ©
Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the sunlight that h... Read full Story
StevelovesTgirls 2019-06-11 12,456 Amateur Big Tits Blowjob Big Cock Guy Fucks Shemale
100%
The Girl Next Door Ch. 02
derezzed Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the s... Read full Story
Gwapo67 2022-05-13 5,211 Bareback Creampie Guy Fucks Shemale cum in mouth
50%
Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... Read full Story
Elainetguk 2023-09-06 4,734 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
0%
Sexing It Up
What catches your eye when you're viewing sample pornographic video clips on the Internet? When it comes to sex, my own tastes are eclectic, although I find myself watching videos involving anal sex, bisexual threesomes, cum shots, gay males, lesbians, oral sex, public nudity, shemales, and spank... Read full Story
shemale lover 2011-11-26 4,248 interracial sex spanking
50%
A Revenge Fuck
It had been a long day. I had fought the traffic after a miserable week to get home early and surprise my wife for what was to be a romantic weekend. But as I pulled up to the house my heart sank. I saw a bright red motorcycle in the drive way and something inside told me, "This isn't right!&qu... Read full Story
shemale lover 2012-06-03 11,054 shemale oral sex Interracial
50%
Clinton
"How many inches?" she asked. "Twelve," he said. "Really?" "Really." "If you're lying, you're just wasting your time." And mine, she thought. "I'm not." "Okay, then. It's a date." Tiffany hoped the jerk was te... Read full Story
shemale lover 2011-09-19 10,578 Big Cock cunt anus
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 6,650 Creampie Big Cock ass fucking
94%
Tortured by the T-Girl Tutor
Duncan didn't quite know how to handle it. He'd planned on a quiet Winter Break. Sleeping til noon, watching too much television and eating tons of junk food. That kind of stuff. He had a whole two weeks off from community college. At school, he was an outcast. They say life gets better after hi... Read full Story
shemale lover 2012-12-18 33,934 Big Tits shemale Big Cock Lingerie domination
80%
Me and 2 black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider my self a crossdresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine ladyboy. I have been taking also hormones for 4 years, on and off and I already saw many changes&he... Read full Story
shemale lover 2013-06-22 5,504 Cumshot suck Ladyboy Guy Fucks Shemale Interracial swallowing
50%
There is love, but war
All characters in this story are eighteen years of age or older.* *The following story is inspired by Miss Evie Hyde's "Slut-Box Challenge" story. The following is written with permission from her to use her premise with my own characters and situation* Billy checked his phone when he got th... Read full Story
ASSEaster5678 2019-07-04 3,398 Guy Fucks Shemale bullies
87%
A Virgin Crossdresser
I was newly turned 18 never even kissed a girl let alone had sex. I had been crossdressing for about a year and had stumbled upon a site called tvchix which where I spent my nights in chat looking and getting an insight into what this world could offer. Bit of background I had named my alter eg... Read full Story
Jessicaxx91 2020-02-06 11,826 Crossdresser Amateur Fetish Lingerie Guy Fucks Shemale cum in mouth
50%
Trying It On For Size
I was twenty minutes early for my one o'clock appointment so I found a shady spot in the parking lot of the upscale chain motel, kept the engine running to power the air-conditioner on the warm Sunday afternoon, took a few deep breaths and tried to relax. My mind wondered back over the series of eve... Read full Story
shemale lover 2011-10-26 7,800 asshole licking sucking
87%
Feminized By My Mother Chapter 2
My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed. "I ho... Read full Story
shemale lover 2012-07-24 13,064 sucking Fetish fucking sissy
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 31,203 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth