Sort by
Relevancy

Free Stories

100%
Sultry Mistress,
Sultry Mistress, Natacha has now been living with me for over a year. It is a cerebral and perverse Domina who immediately wanted to submit me to her desires. She took power over me by making me discover my femininity during role-playing games. Like a spider, she imprisons me in her web a ... Read full Story
sandratvtg 2022-09-20 4,054 Stockings Amateur Lingerie domination Sex Toys
50%
J'ai enfin goûté la bonne chère/chair
Dépucelée en bon et du forme... Chose jamais osée depuis que je goûte la jouissance par tous les sens et dans tous ses sens... Je la découvris quand elle m'a sourit en guise de remerciement pour lui avoir cédé le passage dans la superette du bled où j'étais pour affaires. Sandales à ses pieds d... Read full Story
hippocampus_171 2022-11-09 1,059 Small Tits Amateur Shemale Fucks Guy Guy Fucks Shemale Mature Homemade Ass to Mouth Vintage cum in mouth
71%
Joanna Tranny Prostitute
Joanna stood on the street corner and casually shifted her posture from one leg to the other. So far it had been a quiet evening for her with few punters around. Not many girls were plying the streets either. She’d had one customer earlier. He had been an Asian guy in a Toyota who’d stop... Read full Story
shemale lover 2014-06-19 7,055 shemales Masturbation voyeur
50%
The Greatest Lie Part 15
I think that if you could get honest answers, a lot of heterosexual guys would probably admit to having had at least a passing desire to be a girl. If they were honest, they would probably admit they thought of it "when I first noticed a girl's breasts" or "when I first felt a girl or... Read full Story
shemale lover 2012-01-20 6,212 anal hardcore erotic encounters fantastic
100%
Delectable Debbie
I can't explain why it was that I fancied having sex with a transsexual. I mean I'm a perfectly normal happily married man, couple of kids, mid-40s, a stone or so overweight but reasonable looking, my own hair and teeth and everything. I must admit, I've been with one or two...escorts, hookers, what... Read full Story
shemale lover 2012-08-10 3,915 tranny anal sex orgasm oral sex
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 5,955 anal Cumshot Ladyboy oral
69%
Pune crossdresser Night Girl
Hi friends, I hope you liked my earlier stories. This is my new story about a lady boy / crossdresser / sissy boy. Around 2 years back I came across a profile on Planet Romeo with name Nightgirl. I sent her message that i found her sexy and attracted to her and wanna meet her. I am alway... Read full Story
Stud4Shemale 2017-05-22 7,429 Crossdresser Asian Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
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 10,962 Group Sex Big Tits Bareback Creampie Blowjob blonde Asian Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth double anal
20%
The Greatest Liar, Deal With The Devil
The Greatest Liar, Trans Erotica With a Purpose By Alexandra Rios, © 2019 The Lost Chapter, Deal With The Devil This is a work of fiction. All characters (including the narrator), products, places, events and incidents are either the products of the author’s imagination or used in a fictit... Read full Story
the greatest liar 2019-08-07 3,226 Bareback Creampie gangbang Guy Fucks Shemale double anal
100%
My new Life with Pat. Part 2
While Jean was discussing with the lady from the next table i feel the didlo starting to vibrate and then something like a small ball move up and down into the didlo, it was a prostate massage. I saw Jean playing with a remote control, He increased and deacresed the frequency of vibration and the ... Read full Story
jperrot 2022-08-09 4,943 Amateur Bareback Shemale Fucks Guy threesome Shemale and Girl domination Guy Fucks Shemale slave Ass to Mouth double anal webcams punishment
94%
My black shemale fucking me
My dear guests, I can't deny the fact that I enjoy reading Your comments more and more. Here is what a guy that goes by nick EbonyTSLover writes about the way his black shemale lover Mary with a huge 10.5 inch cock dominates and fucks the hell out of him. I've had Mary's very large black cock so ... Read full Story
shemale lover 2015-06-11 8,858 anal domination dick
72%
Got dominated by 2 shemales on the last day in Thailand
I took a trip to Thailand when i was 25. I told my friends I wanted to go alone so I could clear my head. The real reason was that I wanted so see some shemales. When I first arrived I spent a day looking at every club I could find in search of a good Shemale. It was nearly a week and I couldn't ... Read full Story
shemale lover 2015-08-05 12,244 Asian ass licking domination
50%
Me & Jo Shemale
Yesterday Jo Shemale and I went for on a pussy hunting fall walk. Well, I did, I'm pretty sure Jo Shemale wasn't hunting pussy. It was getting colder, so we had to put on our woolly panties and sweaters. Halfway down the block, we saw the Old Fuck's out in their yard. The Old Fuck's were raking b... Read full Story
shemale lover 2011-08-16 4,596 cock suck shemale
45%
Threesome with random muslim men from Dubai -
As you all know, most of the meetings with my clients happen in good 3-star or 4-star hotels. Clients normally visit my hotel room and have fun. This exciting session happened during my stay in a 3-star hotel room in Bangalore on March 1st and 2nd. I had bookings for both the days and was prepare... Read full Story
Manusha Tranny 2021-10-14 8,999 Crossdresser Cumshot Outdoor threesome Blowjob Big Cock Asian Ladyboy gangbang domination Guy Fucks Shemale Ass to Mouth cum in mouth
25%
Transsexual Actresses Part 2
On the way to Florida, in 1992, Meghan stopped in New Orleans, Louisiana. Her visit to this city lasted an unexpected five years, during which time she began her transformation into a transwoman. A popular nightclub, Papa Joe's, was looking for a replacement for a transsexual who had played Madonna,... Read full Story
shemale lover 2011-09-08 4,906 shemale transsexual porn star
50%
I am Baaack! Part 13
As Joan, Robbie, and Dainie were ascending the stairs inside the Whip and Cuff, Edwina Porter and Louise Edwards were approaching the back door, having gotten off a bus on Michigan Avenue and Touhy and made their way through back alleys. Barbara, in the cab in front of the club's Fargo Street entran... Read full Story
shemale lover 2011-12-17 3,018 anal hardcore erotic encounters
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 13,807 Masturbation cum orgasm cumshots prostate
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 13,880 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
42%
sexy jane story
I love the idea being a crossdresser wearing women outfit bars in panties n sexy outfit not just for the sex I love sex being on my knees sucking cocks in getting fuck by a big cock see win I was very young I had sex with 3 guys one day they ask me will I suck there cocks in I sand yes we want insid... Read full Story
45sexyjane 2019-05-27 4,210 Small Tits Crossdresser Amateur Big Tits Masturbation Blowjob blonde Big Cock gangbang Lingerie Sex Toys shemale + shemale sexy crossdresser
87%
Melissa
I'm a Japanese in my early forties living in Japan and I met Melissa online about a year and a half ago when looking for someone to chat. She is a black, 6 feet 2 inches tall, around 160 pounds and therefore a slim and beautiful transgender girl in her mid twenties. From Brazil, she is very friendl... Read full Story
cttyy 2020-02-24 15,450 Shemale Fucks Guy threesome Big Cock domination cum in mouth double anal
50%
How Sia Shemale Pune fucked me ...
I met Sia through ts-dating . Called her n went to meet her. When I saw her I could not believe that she is shemale n has got cock between her legs. My god so beautiful feminine. Her implants are very sexy n make her more beautiful... Then I paid her n we went to comfortable small bedroom. I d... Read full Story
Stud4Shemale 2021-02-19 5,679 Shemale Fucks Guy Blowjob Big Cock Asian Ladyboy big boobs cum in mouth shemale fucks male Indian Shemale Pune
33%
My new Experience with Amy Cute Shemale in Pune
Hi friends i am back with new story. I am mad shemale lover. and keep on finding new shemales for me. This time i got new website to search for shemale www.massagerepublic.com I saw an advertisement of Amy and i liked her. called her and fixed appointment. went to her hotel, which was ok ok ... Read full Story
Stud4Shemale 2021-02-20 6,131 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale shemale fucks man man-fucking-shemale Indian Shemale Pune
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 3,636 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
Oneness with the bodies
many years went into just fantasizing being with shemales. I was getting hornier day by day to try it out. But being in a relationship there was hardly any room or time for it. I once experienced it in bangkok and confirmed that I really can do it and actually love it. One day suddenly it was br... Read full Story
zyankhaan786 2023-05-30 6,448 Group Sex Bareback Shemale Fucks Guy Big Cock domination big ass cum in mouth double anal
100%
My Noisy Upstairs Neighbors
So... I just moved into my new apartment a few weeks ago, and ever since then all day every day I have been hearing loud noises from my upstairs neighbors. Not just normal walking-around noise, but loud and heavy bangs, crashes, and poundings against the floor, my ceiling. Not only was the sound ann... Read full Story
Chrissy Tunnell 2024-07-15 1,138 Crossdresser Bareback Fetish Blowjob Ladyboy gangbang domination Guy Fucks Shemale sissy double anal
100%
My first pre-op story
I started becoming interested in transsexuals a couple years ago, when I ran across some websites where I found some crossdressers attractive. I was 19 at the time. This led me to picking up Transformation magazine, a magazine more for the TG community, but they featured some really got centerfolds ... Read full Story
shemale lover 2015-06-03 10,717 anal Asian domination
80%
Buffy the Shemale Vampire Slayer Part 13
Buffy's cock slipped out of Baubo's mouth, and she licked the smooth skin of the stiff, elongated shaft with her tongue. Baubo had no hands, but, even so, she was a superb cock sucker. More than once, she brought the Slayer to the brink of orgasm, then backed off, letting Buffy's sexual passion abat... Read full Story
shemale lover 2011-08-23 3,758 Masturbation pussy shemale
100%
Young Hercules: Versatile Stud by The Fan
Prometheus Academy. It sat atop a hill, dominating the vast region of Thessaly, Greece. It was the most prestigious school in the area. The most famous men and women of the world came there to get their education. The sons and daughters of kings and queens, ... Read full Story
shemale lover 2011-12-01 3,354 anal Creampie jacking off
75%
Backsliding: Tim's Story
Every man has a weakness, but not everyman knows what that weakness is until it is too late. The story I'm about to tell is something I'm not entirely proud of. My name is Tim. I'm a 22-year-old college student at California State University. I'm almost at the end of my senior year studying to be... Read full Story
shemale lover 2012-02-09 4,940 sucking fingering Guy Fucks Shemale
100%
Sleazy shemale fantasies
Sifting through the comments that readers leave at Trans Ladyboy, i have found two really hot shemale fantasies that I would like to devote separate space to. They are both written by two horny guys, wyocock and Eddie, who dream about being with shemales all days long (the only difference is that E... Read full Story
shemale lover 2015-02-19 4,505 hard cock suck Asian
72%
Making Shemale Vanity Tube Your Homepage Is A Great Idea!
It all started as a joke. My roommates at the time pulled a prank on me and made Shemale Vanity Tube my homepage. You see, I was about to hook up with this chick one night so they sneaked inside my room before we got there and made that change. Once I turned on my screen in search for some sexy musi... Read full Story
shemale lover 2015-12-17 5,424 suck Masturbation shemale
100%
Black Cock & Birthday Presents Chapter 6
We went back to our suite. I had no idea what time it was. I'd forgotten how many cocks I'd fucked. It was comforting to see an empty bed when she put me down. When I awoke, I was being spooned, my head under the chin of the black man holding me. His skin seemed familiar but I didn't recall anyon... Read full Story
shemale lover 2012-06-26 2,767 anal sex Cumshot domination
80%
How it started
What got me started off watching shemale porn was actually meeting a very beautiful shemale at a beach party. I already knew she was a guy but she was so beautiful. So at one point I asked her if she wanted to go for a walk and after a few minutes and let her know that I was down. Her response was ... Read full Story
PNPFUCKBOY 2019-02-12 11,870 Teen (18+) Small Tits Crossdresser Amateur Big Tits Outdoor Latina Bareback blonde Big Cock Ladyboy domination Guy Fucks Shemale Interracial Sex Toys Mature Homemade Ass to Mouth
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 5,439 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
100%
The Experience of a Lifetime
My divorce was hitting me really hard. My wife outgrew our relationship and started living her own life and I had a front row seat to everything. My heart and life was upside down. I didn’t go out anymore. Friends and family both told me it was time to get my life back on track and start living ... Read full Story
therefill05 2020-11-30 20,086 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob blonde Big Cock Ebony Uniform domination cum in mouth
85%
Becoming My Roomate's Wife
Him becoming my master started a year ago when we moved in as roommates – we are both in our mid 20's and had relationships break up at the same time (we were sharing apartments with our girl friends at the time). We have known each other for more than a decade and have no secrets from each ot... Read full Story
shemale lover 2012-04-01 8,749 Crossdresser anal sex domination oral sex
100%
Discovering Mistress Sarah's World Part 7
Chapter 18 A Life Changing Decision Sunday morning was not much different than the day before for Josie. He woke-up on the floor outside Mistress Sarah's bedroom, dressed in a silk night-gown and his cock was hard and aroused when he awoke. Just like Saturday morning, he crawled into the bedroom.... Read full Story
shemale lover 2012-10-03 5,426 cum domination oral sex feminization
75%
Flowers in the Heart
Chapter 1 "Hey Scott, Fauna kind of likes you," Jenna said, snickering. "Hey Jenna, it hard to hear yourself over that echo?" Scott said as he caught the football, and then heaved it back to Ronnie. "Huh?" Jenna asked, puzzled. "Yeah, your head up your ... Read full Story
shemale lover 2012-11-11 10,434 anal tranny Cumshot oral
100%
Steve to Stephanie Chapter 1
This is my first attempt at a longer story with deeper characters and a more evolved story line. Stay tuned for the next chapter. As always comments are welcome. * Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve... Read full Story
shemale lover 2013-01-29 3,845 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Clara Bow's Academy for Ladies
Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his an... Read full Story
shemale lover 2013-03-27 5,031 Teen (18+) Small Tits shemale public softcore
90%
Shemale Charlotte caught wanking in the bath
Charlotte is a very small 18 year old, very skinny, only just 5 foot but has an amazing pair of breasts which stretching the skin makes them show veins all over. Her pale skin showing the veins even more. Charlotte is also a shemale, her small size and large breasts she also has a very large 8inch (... Read full Story
shemale lover 2013-06-18 6,985 Amateur Cumshot Masturbation jerking Shemale and Girl
87%
Encounter with a dominant shemale
One night I was feeling really horny. I just came back from the gym and I wanted to release and relax. I then began my search for some fun on the personal ads section. I have always been into shemales especially verse aggressive ones. I found this one particular post about Asian bottoms. I was c... Read full Story
SecretAznMan 2013-06-28 47,971 Cumshot Shemale Fucks Guy Big Cock Lingerie ass fucking ass licking big boobs
92%
A very special lady
I knocked at the door, unsure of what to expect. Living in a big city for the last year, where I didn't really know anybody, had certainly put a crimp in my sex life. Where I used to live, in a much smaller town, during my high school years, I'd been able to get my dick into many tight, warm and wil... Read full Story
shemale lover 2013-07-18 6,044 Stockings anal sex Shemale Fucks Guy ass licking ass fingering
100%
Threesome fun
We had invited friend over who has big cock --he arrived and we sat around for awhile talking about sexual encounters of the past --I'm a bi part time shemale cross dresser who is very kinky --anyway it got around to looking around the house and as it happened we stopped in the bedroom , and all o... Read full Story
goodgurl34 2019-01-08 4,414 Stockings Crossdresser Amateur Big Tits threesome Blowjob Big Cock Lingerie domination Guy Fucks Shemale Mature Homemade threesome sex
100%
The Girl Next Door Ch. 03 by derezzed ©
Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Alexis's arm casu... Read full Story
StevelovesTgirls 2019-06-11 18,598 Amateur Shemale Fucks Guy Fetish threesome Blowjob domination Guy Fucks Shemale Ass to Mouth shemale + shemale
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,238 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 2,722 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
100%
The Three of Us
Imagine you are a lonely person on the inside, and just wanting all your life to be loved for who you are. Holli Artigas, was just that person. Wondering whether her obsession with Jon Silva, a football star, was from a casual encounter, or was she truly fond of him? Growing up in the Sao Paulo, ... Read full Story
Jon Paul 2024-04-28 3,194 anal Creampie Shemale Fucks Guy threesome Shemale and Girl cum in mouth double anal shemale fucks female
90%
My Shemale Webcam Tube Date With A Sexy Shemale
I was rushing back home from work because I was suppose to have a date via shemale webcam tube with the sexiest shemale I had ever seen. We met few nights ago and I could just feel the chemistry between us getting stronger. I entered my place, dropped my things on the sofa and turned on the lap-top.... Read full Story
shemale lover 2015-12-29 3,981 anal suck Masturbation
75%
Home Alone With Shemale
I sat alone at my kitchen table. I drank a cup of coffee, smoked a cigarette. I was wondering what to do with my day and then my cellphone rang. It was my girl friend Carla. She asked if it would be okay to stop by, with her new boyfriend. I sensed something in her voice, but I didn’t know ... Read full Story
shemale lover 2017-06-22 13,667 anal Creampie shemale
40%
Thank Heaven for Little Girly Boys
Thank heaven for shemales (and cross dressers). Without them, erotica might still be sugary and nice, but it would certainly lack the variety that spices up one's sex life. After all, there's only one heterosexual plot (boy meets girl), just as there are but two homosexual plots (boy meets boy an... Read full Story
shemale lover 2011-08-18 4,660 ass cock cunt
50%
Mommy Adriana, I Will Obey You
Finally we were on our way home. Interestingly neither Mommy Adriana nor Mistress Andrea had cuffed or gagged me. So I just sat in the back of our car. During the short drive I had some time to think about what had happened in the past two days since my wife, err Mistress Andrea, and I had picked up... Read full Story
shemale lover 2011-12-18 5,664 anal hardcore erotic encounters
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 9,304 Cumshot sucking blonde ass fucking Guy Fucks Shemale
100%
1st time with Thai shemale
So after months of crosssdressing , camming and phone sex i finally decided to have a meet. I found a lovely Thai shemale on birchplace and went to see her in London. She was gorgeous and put me at ease straight away. After a few minutes of massage she started licking and sucking my nipples, then as... Read full Story
Nutcracker29 2013-04-09 9,253 first time suck Shemale Fucks Guy Asian big boobs
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 22,778 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
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 13,094 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel