Sort by
Relevancy

Free Stories

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 7,853 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature 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 5,794 Big Tits Bareback Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
95%
A Trip to the Beach
I had known Stacy for about three years, but I had never known about her little secret. That day when it was revealed changed everything for me, and for Stacy too. We were the greatest of friends, spending almost all our time together. We had come as close to each other as lovers but as two women, n... Read full Story
shemale lover 2014-10-19 5,348 shemale oral
88%
My first taste of shemale cum
This horny story was posted at our forum by a guy named Capablanca who seems to have finally admitted he prefers playing with shemale cocks over playing chess. ;) I have already described my first encounter with a shemale - an amazing experience. One thing I've been looking for since that first e... Read full Story
shemale lover 2011-06-28 40,327 Blowjob cum domination
75%
A Shemale Vacation Part 3
At the French border, it was discovered that we had no passports. We were taken from the train and into a room for questioning. All four of us, Josh, Olly, Harry and myself, were terrified. Sure, we'd been in a sticky situation before on this trip, sticky particularly for me rather than the others, ... Read full Story
shemale lover 2011-09-05 4,160 anal sucking cum
100%
Taken and in Public Part 3
I tried to go to sleep but was just so horny; I wanted to dress up again; I wanted to go out; I wanted to be fucked! All these emotions were running thru my head and I just lay there. My mom told me she would be starting the 7pm to 7am shift at the hospital for some time and thought I should get... Read full Story
shemale lover 2012-01-14 2,857 Fetish crossdressing ass fuck
33%
My shemale GF Part 3
Christy and I are on the couch, we had just woke up, I have a butt plug in and slept with it in cause she was going to fuck me today. She has a Pink G-string on and a Pink bra with her G-string pushed to the side for her cock. Me I'm wearing Metal Mulisha boxers and a Tyler, the creator T-shirt on, ... Read full Story
shemale lover 2012-07-09 3,468 anal shemale cum jerking oral
88%
A Walk In The Park
Each day I spend my lunch down at the park in town. It is down by the lake. I sit and eat my lunch and watch the people walk by. I watch them and they watch me. Then when I’m done I go for a long walk. Each day that I go I start my walk about the same time. At 12:30 pm I start my walk. I like ... Read full Story
shemale lover 2012-07-20 4,717 Cumshot shemale oral jacking off
92%
My shemale girlfriend
I met Andrea out side a bar on the west end, she was outside smoking a cigarette, I started a coversation with something stupid like "you come here often?" she laughed and we started talking had a couple of drinks and exchanged numbers. Andrea is about 5"10", shoulder lenght dark... Read full Story
shemale lover 2013-04-26 8,696 Cumshot suck fingering cum swallowing stroking
96%
A Trip to the Beach
I had known Stacy for about three years, but I had never known about her little secret. That day when it was revealed changed everything for me, and for Stacy too. We were the greatest of friends, spending almost all our time together. We had come as close to each other as lovers but as two women, n... Read full Story
shemale lover 2013-07-21 10,457 hardcore Cumshot Shemale and Girl oral sex kissing
87%
My 1st time with a shemale
I always had the fantasy to be with a shemale, and today i gained the guts to go to a shemale. I saw the add in the newspaper and called, she was a brazilian (ussually the best ones are brazilian :) ) When i arrived to her apartement, she had a beautifull lingeri, and i noticed her big tits, my co... Read full Story
zongf2008 2014-09-02 4,801 first time ass suck shemale dildo
100%
My Life as a Shemale Part5
I wore my new clothes now everyday, Sam and Tim helped make sure that I learned that my underwear was in the right place and I had this terrible habit of not keeping my legs together when I sat down. At night I was always wearing my nighty and it all just made me completely horny all the time and it... Read full Story
shemale lover 2015-02-27 2,902 tranny Amateur shemale fingering stroking
100%
First Cross-dressings Loosing Anal Virginity
It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... Read full Story
Trapbomb1 2022-07-29 6,678 Teen (18+) Crossdresser Bareback Creampie Blowjob Big Cock virgin virginity sissy cum in mouth double anal sissy slut virgin ass
100%
Jennifer
WhiskeyIsGood I woke with a start, startled by a loud banging sound from downstairs. The floor shook from the vibrations, causing me to sit upright in my bed and glance towards my bedroom door. What in the hell, was going on down there? My question was quickly answered, by another loud bang, foll... Read full Story
Gwapo67 2022-09-13 5,922 Big Tits Bareback Shemale Fucks Guy Blowjob blonde Big Cock
100%
Crossdressing at CCBC in Palm Springs
I recently stayed at CCBC in Palm Springs. For those of you who are not aware of it, it is the largest gay resort in Palm Springs area. The resort has about 30 rooms, lockers, a pool, steam room and indoor and outdoor play areas all on a one acre outdoor enclave. I arrived there on a Tuesday and dre... Read full Story
Rocky8844 2024-05-27 2,576 Crossdresser Group Sex Blowjob Lingerie pantyhose cum in mouth
81%
My First Shemale
Let me tell you a little bit about myself I’m five feet 10 inches tall around 220 pounds, brown hair and eyes very muscular, I’m an ex-professional boxer. Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort Lauderdale, when one night I heard a commotion in the ... Read full Story
shemale lover 2018-02-10 18,007 anal cum oral
74%
Sexy Young Shemale
When I was twelve my next door neighbors Sam and Ted trained me in the art of cocksucking and creamy yummy delicious cum eating for hours everyday during my summer vacation and I fucking loved it! I was small framed and wore my long blonde hair in a pony tail and always wore my smallest shorts so I ... Read full Story
shemale lover 2018-09-28 10,527 sucking Big Cock cum swallowing
100%
My first time with a shemale
Let me tell you a little bit about myself I'm five feet 10 inches tall around 220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer. Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort Lauderdale, when one night I heard a commotion in the parking l... Read full Story
shemale lover 2011-08-23 3,796 anal sex cum oral sex
100%
Special Shemale Fun
Everyone in the hallway jumped slightly, turned and quickly looked at the tall girl near the sound of the slamming locker. Satisfied that there was no crisis at hand, the kids at the school mostly went about their business. Of course, there were the few admirers that glanced at the girl at the locke... Read full Story
shemale lover 2012-02-06 5,172 sucking shemale massage
89%
Father-In-Law Shemale Adventure
My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last momen... Read full Story
shemale lover 2012-07-04 7,340 shemale oral facial facefucking
75%
My shemale GF Part 2
So today she, her name is Christy, she wanted to do something kinky, very kinky I said that's fine. We cleaned up, she went into her closet, which was filled with dildos, butt plugs, sexy clothing, fleshlights, cock rings, paddles, lube, videos, magazines, bdsm things, and a fuck machine. She came o... Read full Story
shemale lover 2012-07-04 3,587 anal sex Creampie shemale Latex rimjob
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 2,623 anal sex Creampie fingering Shemale and Girl facefucking
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 7,105 sucking shemale fucking
100%
Pounded to submission part2
Two days ago Joesph was checking out porn. A couple of BBW vids here some interracial there, the usual. Then he saw a just viewed picture with a Brazilian She-male and couldn't stop looking. With his curiosity getting the better of him he clicked on it. She was gorgeous! Her face appeared to be as f... Read full Story
shemale lover 2013-04-21 7,843 Cumshot suck shemale oral deep throat
86%
Sexy shemale 69
I was out at a casino in Reno after work. It was about 10pm and I was unwinding having a beer playing some video poker and watching ESPN. I saw a beautiful dark hair lady at the end of the bar so I decied to move closer. Once I got down there we chat a bit. Her name was Kim. She had some nice B-cups... Read full Story
shemale lover 2013-06-18 4,318 anal Cumshot suck shemale oral fingering cum swallowing
84%
Shemale Gangbanged
Hi........readers.......i am a shemale whose presence looks like an angel.......Due to my physical appearance....boobs,ass....whatever boys use to look at is as soft as cream.My story starts with a mistress ....who fucked me twice....but without any payment...So it was a summer and i called him to p... Read full Story
shemale lover 2013-07-02 6,134 hardcore Cumshot shemale gangbang ass fucking domination 69
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 8,685 first time ass shemale Big Cock feet
100%
Double Anal With a shemale
....He answered the door and there she was beautiful as ever. He had just paid 500 dollars to have a transsexual e****t come directly to his door and greet him. She had on a long pea coat and thigh high boots. When she took the pea coat off all she had on was a one piece swimsuit. Her tits were a 36... Read full Story
shemale lover 2015-04-29 5,335 tranny suck Big Cock ass fucking dp precum
50%
Angel The Shemale Vampire
Angel stood in the shadows watching hungrily as the group of laughing young college kids came toward her down the alley. The group was made up of four guys and a girl. The girl was hanging all over one of the guys and it screamed how badly she wanted to get in his pants. Angel's smile broadened with... Read full Story
ASSEaster5678 2018-10-29 7,363 Group Sex shemale vampire
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 3,756 Crossdresser Masturbation Blowjob Lingerie Mature cum in mouth
86%
My adventure at the adult bookstore
I was horny as fuck the other afternoon. I had some time to kill so I hit squirt.org and fetlife seeing if there were any dudes needing a free blo-n-go. Nobody took me up. Sad face. I drove to the local adult book store that has video booths. I was sitting in the parking lot watching people go in... Read full Story
shedawg 2019-04-15 6,225 Amateur Outdoor Blowjob cum in mouth
50%
Not your usual birthday present
So here we go again “Happy Birthday” to me, at 51 it’s not that great really it’s just a reminder your getting older!! Anyway here I am 51 having an absolute ball and fulfilling my wildest dreams, Justina likes being out of the closest and loooooves cock.. So for her birthday she hopes someone has ... Read full Story
Samantha Jewels 2022-01-12 2,732 Stockings Crossdresser Amateur Blowjob Big Cock gangbang Lingerie domination Sex Toys Mature cum in mouth
100%
Aquick encounter with an Escort
Two years ago my wife and I were downtown, so I picked up a paper. While scanning the escort adds I noticed a picture of a beautiful long haired girl kneeling in such a pose as to cover up all her private areas. Reading the caption, I was shocked to learn that I was looking at a shemale. I c... Read full Story
Hunter043 2022-04-12 2,989 Amateur Latina Asian 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 4,233 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 4,070 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 4,281 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 4,256 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 5,489 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
98%
Shemale on Shemale
We were in the back of a taxi, our tongues deep in each other's mouths, tasting and sucking and swirling. My hand slowly moved up her perfectly toned thigh and under her skirt. I lightly caressed her half hard cock through her thong, barely touching her, just tenderly stroking with my fingertips. Sh... Read full Story
bigtranslover 2014-01-27 6,818 ass cock shemale
75%
My First Encounter With A Shemale Escort Part 3
Crystal stood up and moved towards the bed. She sat down on the end and beckoned me towards her. Her cock still stood semi-erect between her toned thighs. I made my way towards her and as I did so she lay back, raising her legs in the air. She told me to kneel between her legs so I could fuck her in... Read full Story
shemale lover 2011-08-17 3,404 hardcore anal sex shemale
75%
A Couple And A Shemale Encounter
Not long ago I was sitting home alone on a Friday night with nothing much to do and feeling horny so I decided to go out. I showered, misted myself with my favorite perfume, put on a sexy black bra, rolled on a silky new pair of jet black sheer to waist pantyhose, slipped into a tight, very short, l... Read full Story
shemale lover 2011-08-26 5,154 anal Creampie shemale
100%
Shemale Fantasy
I had wanted to be with a she-male for some time. I had purchased several she-male DVDs and found that being with someone as sexy as that really turned me on. I would fantasize for hours on end about being with one of those 'special' girls. Several of my male lovers couldn't understand my attraction... Read full Story
shemale lover 2011-08-27 4,164 suck cum swallowing facefucking
50%
Realization vs. Reality
So…here I sit. 40 years old and revisiting the confusion of my youth. I am, and always have been, a first string heterosexual male. From my earliest memories of when I began to notice girls, I have always delighted in the wonders of women. I became sexually active at age 16, and there has nev... Read full Story
shemale lover 2011-10-18 3,553 sucking shemale cumming
85%
Continuing to Love the Feeling
After an exhausting but exciting day, i slept very well and arrived the next morning ten minutes early. I went through the back basement door and began changing. Ten minutes later i heard Mrs. Hawthorne calling me, Bitch Sheri come up here now! My maids outfit wasn't complete but i went up to ... Read full Story
shemale lover 2011-11-03 3,445 asshole sucking cum fingering
100%
A Night of Makeup, Cock and Cum
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further,... Read full Story
shemale lover 2012-04-18 4,688 Cumshot jerking off domination Sex Toys cum swallowing
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 6,180 anal sex Creampie shemale Big Cock
100%
A Tale of Cum and Passion
It was an anonymous meeting, set up through a popular Internet site. The profile specified I was looking for a transsexual or a transgender woman with nice legs and feet. Basically I was looking for a chick with a cock to satisfy my fetishes for legs, stockings, feet, cock, and cum. Victoria walk... Read full Story
shemale lover 2012-07-06 4,045 anal sex Cumshot shemale oral sex
91%
Cinema fun
I love all sex, anything is good sex as long as everyone involved is happy. Many years ago while working in Berlin i took my car into a garage to have some work done, i was told it would take a couple of hours to complete, not really wanting to take a taxi home for such a short wait i decided to go... Read full Story
shemale lover 2012-11-01 3,210 fingering oral sex cum swallowing
97%
Never Wanted To Be Your Girlfriend Ch. 02
So, after being made up like a slut, left glued to a pair of silicon breast forms, and caught sucking-off my best friend, I was pretty sure my day couldn't get any worse, but I had come nowhere near the end of my torment, as Michelle now had something else planned that I was probably not going to li... Read full Story
shemale lover 2014-07-21 9,443 hardcore Cumshot suck Lingerie ass fucking
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 6,531 hardcore Creampie Big Cock ass fucking Shemale and Girl
54%
Shemale transformed in to a living sex doll and kept captive
I had connected with Master X on a BDSM Fetish contact site. He was the owner of a fetish store and he said that he had been on the BDSM for several years. He had carefully studied my own profile and had seen that I had an immense interest in being used like a slut, being covered head to toe in ... Read full Story
__tiffanylondontv__ 2014-09-30 8,155 ass Fetish bdsm domination bondage
100%
Stepping Out
All through the next week we searched through almost all the online dating sites and it was the same as before. Some wanted just me or just Deena, but not the both of us together. One good result was that I found a trans gender support group and they were going to meet on the next Tuesday which was ... Read full Story
Setinkhan 2021-06-02 3,028 Crossdresser Fetish Big Cock Interracial cum in mouth shemale + shemale
100%
Hooked On Shemale Cock
Nitromethane Well, that did it, I finally swallowed my first load of shemale cum, and I haven't been able to get it out of my mind since. It was three years or so that I'd been wanting to have a shemale cum in my mouth, and it was everything I'd dreamed and more, but now what? I'm at work think... Read full Story
Gwapo67 2022-02-01 3,204 cum in mouth
75%
A slutty cd needing to get used
Crossdressing is something I have done in ll for many years. It's purely sexual and it gives me a thrill. I made plans with a guy to meet up and play. So I put on a slutty outfit underneath my clothes. I get to his house and take off my outer clothes in his bedroom. So now I have on a short skirt,... Read full Story
Thiscdneedsitdeepinside 2022-10-05 3,954 anal crossdressing gay blow job spit-roast mutual masturbation golden shower cum drenched
100%
I met a guy in the nightclub and I didn't tell him I was Trans
I’d worn an absolutely killer dress just to make sure I got what I was looking for that night. Dancing under the lights I could feel eyes all over me, and as the evening progressed men became bolder and bolder about approaching. This one was athletic, sexy and had all the right dance moves, at least... Read full Story
Madison Heights 2023-03-25 6,608 Cumshot Outdoor Blowjob Big Cock cum in mouth club outfit Surprise Cock Partying surprised
100%
Nikki's Massive Strap-on
A quick recap in case you haven't read my previous stories. My name is Kacey. I'm 20 years old, white, 5'10" and 150 lbs. I have straight, shoulder length dark brown hair, light brown eyes and a thick, 6" cut cock. My girlfriend is Hannah, who also 20 years old and stands 5'10" weighing in at 140 lb... Read full Story
KaceyKlarissa 2024-02-23 4,757 anal Crossdresser Big Tits Cumshot Fetish Big Cock Lingerie Shemale and Girl domination big ass Futanari sissy cum in mouth