Sort by
Relevancy

Free Stories

100%
Khwaish Pune fucked me hard
I am a shemale trans lover. Me 6 ft tall, muscular, handsome , fair man 52 resides at pune. I use tobe top but last two years I am living being bottom too. I love sucking shecocks and hv sucked quite few in pune. Story begins when I was looking for some trans partner on Planet Romeo I came acro... Read full Story
Stud4Shemale 2024-04-14 3,146 cum in mouth Indian Shemale Pune Shemale Shemale Fuck Man hard-core shenale fuck
85%
Good hardcore fuck with a shemale from Vancouver
Our reader Tommy writes about one of his adventures with a shemale. Sure, it turned out to be not as romantic, but, as he says, nevertheless it was a good hardcore fuck! Thanks to him for this great story. One night on biz in Vancouver I saw some adverts in the paper for shemales and got hot and ... Read full Story
shemale lover 2015-03-25 5,602 anal Blowjob cum
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 13,905 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
81%
A LadyBoy For My Wife
I have been happily married to my sexy Thai wife Lisa for three years now. My wife is Thai is petite (5'1") with a stunning figure, a tight ass and long waist length black hair. We had met in a bar in Thailand and subsequently we were married back here in the UK. She was very loving with m... Read full Story
shemale lover 2012-06-23 10,847 Group Sex Masturbation shemale Ebony facial
81%
First time with ladyboy / bottom
Hi everyone! now it is my turn to share my experience in Thailand. We were on a Christmas vacation on an island, and I didn’t even know ladyboy existed then. At a Christmas beach party I chatted and danced with a woman and we ended up in my bungalow. We kissed a lot and I knew that now I was g... Read full Story
FoxyLover'ts 2020-10-06 16,166 Cumshot Blowjob Big Cock domination Interracial Homemade cum in mouth ladyboy ts thailand ladyboy shemale fuck guys virgin ass bottom boy bottom virgin
80%
fuck by my best friend's family
= Part 1. Alice's father = My name is Onikky 28-year-old Shemale from ASIAN, this story only shares the first experience of making love. The story begins when I first moved to a big city, looking for a new atmosphere, I don't have a place to live that I know is only my friend's name Alice who ... Read full Story
Onikky 2019-06-25 9,401 Amateur Masturbation Big Cock Asian Ladyboy gangbang Lingerie domination Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
100%
Thai Ladyboy goddes in Tokyo and a cheap love hotel
This is a real account of my meeting last week with a beautiful Thai ladyboy working at a flashy show at a night club in Tokyo. Written as a not to her. Hope you like it. You sexy ladyboy goddess, I must say you have the most beautiful body. When we first started drinking wine and talking ... Read full Story
lblover77 2012-10-09 9,818 anal Ladyboy oral
100%
Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
Regina10 2020-09-14 4,185 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
75%
So good fuck with me and my klients.
Hello, I am Francesca, and I offer company to couples and women. A few days ago, a couple hired me for two hours.The woman was fucking me with her strapon while I was stroking the man's cock. She was pushing her hard cock deeper and inside me, I could feel my ass dissolving more and more. I turn my ... Read full Story
Francheskahotass 2021-08-11 3,354 Crossdresser Amateur Group Sex Cumshot Shemale Fucks Guy threesome Ladyboy Lingerie Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
75%
Soo, my ladyboy friend in Bangkok
This shemale story is not your usual one as it's written by a lesbian girl Jamie and it involves a very sensual description of sex with an Asian ladyboy. Enjoy reading! Well as an openly gay Lesbian woman (submissive as I say) a long way indeed. My friend in Bangkok, Soo is a beautiful, articula... Read full Story
shemale lover 2015-02-01 8,664 Asian Ladyboy Shemale and Girl
85%
Busted and Hoodwinked
INTRODUCTION Mack and Barry were cell mates in prison which is where they first met. They had both been convicted of burglary and breaking and entering. The befriended each other while in prison and became lovers. Barry was gay and Mack became a bisexual during their time in the same cell. Mack a... Read full Story
shemale lover 2012-09-30 5,960 anal Cumshot Ladyboy oral
100%
Lady and the Cop continued
The next night Regina got a visit from. Larry the cop who openly declared war on shemales and trannies. He was working a homicide where a trannie friend had been killed in her apartment. Larry was a known shemale hater and he never failed to express his opinions. Tonight he was in her apartment to ... Read full Story
Regina10 2018-03-06 4,679 Small Tits Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
85%
Cheating Sissy Wife
My name is Ginger and my main stud is Keith, a truck driver, who is only in town once a week. We have and ongoing role-playing fantasy that we carried out whenever he was in town. I am his dutiful ideal housewife who is perfect in every way. My talents excel in both the kitchen and the bedroom. I fi... Read full Story
Regina10 2020-07-27 7,642 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
100%
Uncle sweet Lover
Uncle Barney called me this morning and wanted me to keep my evening free. He wanted to meet me at the motel with a surprise for me. I was so excited and could hardly wait. I had to decide on something to wear, but when I thought about it, I realized that I wanted to wear something special. He would... Read full Story
Regina10 2024-02-19 4,784 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
100%
Late Night Snack (Touch me in the morning)
I was awakened abruptly by someone banging on my door at 1am. At first, I thought it might be Harry, the man who replaced Mr. Cobb in my bed a few nights ago. He had been persistent and horny constantly. I think it was because fucking trans women like me was new to him and he hadn’t got enough of th... Read full Story
Regina10 2024-03-28 3,954 anal Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Ebony Ladyboy Lingerie
100%
Black Dickgirl Fanstay
It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sleeping with a black shemale was about to come true. She paused... Read full Story
ASSEaster5678 2018-09-14 6,546 Ebony Ladyboy dreamgirl
80%
I got humiliated in a catfight
Im a crossdresser and I am very feminine and extremly dainty. I was attracted to a man at a park I went to. He knew I was a crossdresser. I would always say hi when I saw him, but that was it. One day he asked me(on a rainy day as I was getting in my car), do I have a boyfriend am I bi, he wanted to... Read full Story
Kaylamoore994 2023-03-26 5,996 Crossdresser Outdoor Masturbation Fetish Ebony Ladyboy Lingerie humiliation fight sissy crossdresser catfight
96%
True story about a ladyboy first timer fucking her customer's as
Those of You that dream about having a beautiful Asian ladyboy fuck your ass will certainly love this naughty story posted by our reader Tommy where he got his asshole violated by a cute ladyboy. Did I mention that she was a first timer and Tommy was her first customer? Hi, me again with anothe... Read full Story
shemale lover 2015-03-05 10,458 anal cum Asian
78%
Hot Ladyboy
I had a phone number for a hot ladyboy that my friend insisted that I call for something different. I had always admired them but I had never been with one before. I finally decided to call the number a few nights ago and a soft feminine voice answered. The hot ladyboy was named Hollie and she to... Read full Story
shemale lover 2015-09-29 5,859 anal sucking nipples
87%
My ts fuck
Patong beach thailand a few years ago, a few drinhs at a bar with some friends on going to toilet at public loo which was next door to ladyboy bar. Standing and relieving myself in runs two lovely ladyboys from next door. Who proceed to do there make up and have a good look at my cock for good measu... Read full Story
shemale lover 2012-06-15 5,079 anal sex Cumshot Ladyboy rimming
100%
Womanhood for Jenny Chapter 2
Despite the discomfort of her 'boob-job,' and the other surgeries, jenny had enjoyed their Caribbean 'vacation.' During the drive from the airport, she was impatient to show her friends the 'new jenny,' but felt the weariness of the return trip. She was happy when Master Charles pulled into their ow... Read full Story
shemale lover 2012-10-08 3,784 anal sex Cumshot cum swallowing boob job
100%
My Ebony Prince
I love dressing for my man, Terry. When he grips my legs through the stockings I wear I feel dirty, slutty, and oh so loved. The way he lifts my frilly negligee and peppers my stomach and thighs with wet, meaty kisses always makes me leak through my panties. He licks my moist clitty through the fabr... Read full Story
RazedGlory68 2012-02-28 3,343 anal crossdressing gay
91%
Hot Slutty Sissy
Hello, It’s me, and. I am about to make a big decision and right now I am dedicated to my fantasy. I got a call today from one of my ex boyfriends. I got so horny when I heard his voice that my nipples turn to steel. My titties seem to respond to the sound of his vibrating baritone. I couldn’t refu... Read full Story
Regina10 2020-08-14 6,797 Crossdresser Cumshot Bareback Fetish Blowjob blonde Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,363 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
92%
Well endowed ladyboy Yoko
Here's the second part of the story posted by our reader Tommy, and i'll tell you what, it's even hotter than the first one! I went back to Casanova some months later, hoping to see that well endowed ladyboy. She was dancing on stage - we made eye contact, she hopped down straightaway and we kiss... Read full Story
shemale lover 2015-05-01 6,462 anal cum Asian
100%
I got anal creampied at the beach!
As soon as we got onto shore, I knew it was the perfect place. The hot sun was beating down on us and my body was tense with anticipation. Finally, we were going to be alone out in the wilderness with nobody around and could enjoy each other thoroughly. My hunky date and his monster cock were going ... Read full Story
Madison Heights 2022-12-01 4,770 Cumshot Outdoor Creampie Fetish Blowjob Big Cock Ebony Guy Fucks Shemale public bbc massive
100%
Finally A Real Man
After my divorce I found I had some time to indulge in my many fetishes and fantasies. Those being; cross-dressing, smoking 120s and man to man sex. None of these were a factor in my separation however. It wasn't long before I was on line ordering lingerie and shopping locally. This has been going o... Read full Story
shemale lover 2012-08-06 4,820 anal Crossdresser oral
50%
The Ultimate Cock Ball Torture
I miss my cock. Sometimes. I had one once - one of my very own, connected right to me - but now it's gone. Never thought I would miss it. I'm sure you've guessed by now that I am a full transexual. I had the boob job and started hormone treatment years ago and felt much better as a shemale th... Read full Story
shemale lover 2012-04-29 3,595 anal sex oral sex
100%
S is for Selena
"His name is Ken," my friend Isabella had told me as she recounted her own encounter and that of her friend. "I got to first base with him that first time he came in the club. Just a quick snog and then he seemed to take fright." "Were you wearing that red dress, the one ... Read full Story
shemale lover 2012-08-27 3,825 anal Cumshot blonde
100%
Secrets
Jon had invited me to spend another weekend at his place with another of his friends. I always find his friends to be interesting so I accepted. Jon had given me a garage door opener and a key to his home after my first visit. He met me as I parked my car in the garage. He was wearing his usual skim... Read full Story
shemale lover 2011-11-01 6,071 anal Blowjob transvestite
100%
Mommy, can I be your fuck-toy?
I saw my step-mom taking a shower by accident or so I thought. It was not until I saw her pretty big she-cock jus hanging there between her sexy well defined legs. It was even hard & it was already as big as my cock when its hard. It looked so big that it was a bit scary yet some muscle in my anus s... Read full Story
Curious_billy 2022-11-22 7,207 Amateur Cumshot Masturbation Bareback Shemale Fucks Guy Blowjob Big Cock Lingerie Mature Homemade Ass to Mouth cum in mouth seduction
100%
Bangkok Bar Girl
I recently attended an international trade conference in Bangkok. The manager of our small office there, a big, ruddy-faced 50-something American called Mac, took me under his wing. (I'm 32 by the way, and married.) Before I left for the conference my colleagues in London wound me up mightily about ... Read full Story
shemale lover 2012-02-11 4,522 anal sex Ladyboy Sex Toys
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 33,833 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
38%
Am I gay?
Please help me. I'm confused and unsure if I am gay. I feel so ashamed of myself. I don't want to be gay but I was molested by my neighbors at 6 years old and from then on I would wear my mom's panties or sniff my sisters while masturbating. Cumming would always make me feel guilty for what I have d... Read full Story
Chinaysissyslut 2020-02-24 6,240 Stockings Teen (18+) Small Tits Crossdresser solo Amateur Masturbation Asian Ladyboy Lingerie Homemade webcams
100%
Camming down the rabbit hole Ch6
In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... Read full Story
Dani_does_Dallas 2021-10-11 4,897 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
66%
She said I was her fucktoy
So there I was, bent over the bed, face down, buck naked & the feeling of some type of oil being poured down my ass crack. By shivering at how suddenly my asspussy felt so wet, it also looked like I was wiggling my ass in a sexy manner judging by my friend Alma & her reply of "Oh yeah baby. That's h... Read full Story
Curious_billy 2023-06-29 6,015 anal Amateur Bareback Creampie Big Cock Ladyboy domination Homemade
100%
Betrayed Chapter 4
I really wasn't surprised when Dianna directed me into the parking lot at Ringers. It was only a few blocks across town from my new home; a five-minute drive, if the traffic wasn't killing at the time. Consciously, it had not been a factor in my decision to take the new place. Sub-consciously... wel... Read full Story
shemale lover 2012-05-29 5,080 Cumshot orgasm condom sex
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,045 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
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 13,101 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
100%
Camming down the rabbit hole Ch3
Slowly stirring from my sleep, I stretched under the covers and a pleasant sensation spread across my torso, remembering what I was wearing when I went to bed I smiled at the caress of the fabric on my skin. It was a strangely comforting feeling, the pressure from the bra, panties and nightie felt l... Read full Story
Dani_does_Dallas 2021-08-18 5,208 Stockings Crossdresser solo Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade
100%
From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
hippocampus_171 2023-01-11 4,361 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
75%
Aunt trip
In 2013, after almost three years of service in Afghanistan, George Madsen, a gay Royal Navy communications petty officer, retired. His experience in the distant deserts had left an indelible mark, the memories of friends lost and challenges faced still burned vividly in his mind. Coming home was n... Read full Story
Rebba 2024-04-25 3,259 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
100%
Camming Down the Rabbit Hole Ch. 09
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... Read full Story
Dani_does_Dallas 2022-03-22 3,460 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 11,013 Fetish crossdressing feminization
100%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2013-07-18 8,444 anal sex Ebony oral sex Interracial kissing
100%
He Could Have R*ped Me!
This guy was so big, taller than me and I'm 6 feet, and bigger, not fat, just right for his big size, and I am so skinny, except for my tummy, that he could have pinned me down and forced himself onto and into me against my will, and no matter how much I'd struggle with him and fight back, he could ... Read full Story
Chrissy Tunnell 2022-02-02 2,799 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
Lola Chapter 2
Lola Chapter 2: A couple? It wasn't as if we were together. We had jerked off together once, and of course we slept in separate rooms, but I slept restlessly that night. Dreamed something scary that I couldn't remember in the morning. I didn't have work scheduled that day so I took it easy. When ... Read full Story
BellaBeau 2023-10-05 5,428 anal Cumshot Creampie Guy Fucks Shemale Homemade latina Tgirl
93%
The Best Of Both Worlds
The best of both worlds Sandra Grosset climbed out of her bath, and began drying herself off with a huge fluffy bath towel. She had a big date with Greg, and she was really looking forward to it. Greg understood her, not only understood, but was very eager to fuck her. She had been spurned b... Read full Story
TgirlLover4Life18 2018-06-20 9,042 Stockings Blowjob Lingerie bisexual Homemade cum in mouth transwoman tgirl and girl tgirl and male
77%
Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
Regina10 2020-09-16 5,447 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
100%
K*dnapped & R*ped
"You're nothing but a tease, a flirt, you just like to play around and lead guys on," someone messaged me on the swinger site I'm on called AdultFriendFinder. "No," I replied, "I have actually hooked up with guys I met here, I am just very busy." And that is the truth. I work a full-time job and ... Read full Story
Chrissy Tunnell 2022-02-02 3,511 Crossdresser Amateur Outdoor Bareback Fetish Ladyboy domination Guy Fucks Shemale Homemade
50%
Lost Girlfriend Part 2
I was in a pretty pissed off mood for a few days, having just lost my latest hot Tg girlfriend, Kelli to Alesha, a well hung black Tg, and decided to go to my favorite exotic dancers club. I recently had some interesting adventures with several of the dancers, I wrote that up in a 2 part short ... Read full Story
shemale lover 2011-12-03 6,249 Ebony transsexual domination
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 3,957 anal sex Creampie oral sex facefucking
73%
Black Girls Have Big Dicks
She was like no woman I had ever seen before. She walked into a room and everyone's eyes were on her. She just had that incredible presence that just lit up the room and everyone just wanted to be around her. I was working behind the bar of a trendy club when I first saw her saunter in on her long l... Read full Story
shemale lover 2012-06-27 21,320 anal sex oral sex black cock
60%
The Creators: Book One by
Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... Read full Story
sagga 2018-09-18 30,372 Teen (18+)
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 4,090 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
100%
Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
Curious_billy 2023-05-07 7,353 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade cum in mouth