Sort by
Relevancy

Free Stories

66%
My Kinky She Male Porn Pictures
I never thought that I would enjoy making shemale porn pictures,but here I am and I must say it's been a crazy ride.I met Mike one night in a bar, and that's how my journey started.Mike was a very sexy and he was a real charmer. When he approached me he didn't know my secret,and I didn't want to ... Read full Story
shemale lover 2016-01-30 5,467 anal Big Cock transsexual
73%
My Kinky Shemale Mobile Porn Movie
I liked him very much but I couldn't approach him. I have been sitting in front of him in the club and I could smell his colone.I have been fantasizing about him all night,and I just had to make contact.Eventually he approached me and we started to talk.We were chatting about all sorts of stuff and ... Read full Story
shemale lover 2016-05-02 9,470 Big Cock oral ass licking
83%
Buffy the Shemale Vampire Slayer Part 6
Buffy arrived in the demon dimension on her elbows and knees, just as she'd been when her mentor, Rupert Giles, had been butt fucking her a moment before the spell they'd cast transported her from his apartment to this bizarre land of the damned. Her legs were still spread wide apart, and ass was st... Read full Story
shemale lover 2011-08-19 4,245 asshole shemale Big Cock
71%
TGirl Initiation by 3 BIG BLACK 12
In my teen years I was often told that I was quite feminine.The high school punks always told me that I filled out the back of my jeans in a girly way. After taking a shower one day I did notice that they were right, I had a nice white bubble butt. Not to mention that my lips were also quite girly. ... Read full Story
TgirlJill4BBC 2013-06-04 9,030 Stockings Cumshot suck Big Cock Lingerie Interracial Latex
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 47,897 Cumshot Shemale Fucks Guy Big Cock Lingerie ass fucking ass licking big boobs
89%
Shocking shemale surprise
I had been out with friends partying after a professional basketball game and reached my hotel around 12:00 I wasn't yet tired and not needed anywhere the next day I decided to call for a massage. I had an adult newspaper and really didn't read the add. I basically called the first number I came ... Read full Story
shemale lover 2013-08-09 13,314 suck shemale Big Cock oral swallowing stroking
68%
Next time fucking her cross dressing husband and bred his wife
Wachenheim dressed up in a pretty skirt and loose blouse with his wife watching walked up to and knelt between my legs. He sucked my thick long black cock. His wife watched and masturbated as he worked my cock deep in his mouth. She knew as soon as I did him that she ws next. It was her wishes for t... Read full Story
Rocky Wachenheim 2014-09-23 4,428 Crossdresser suck Masturbation Big Cock cd
61%
Car Broke Down
A Fantasy: Car Broke Down My car was running hot so I pulled into a driveway so that it would cool down. I got out and raised the hood and added some water. I then got back inside and smoked a cigarette and sipped on a beer that I had. I listened to the radio and glanced out the window and... Read full Story
iluvgurls 2018-11-14 7,300 Small Tits Creampie Blowjob Lingerie cum in mouth
100%
Lady In The House Ch. 03
A story by MicheleNylons ( Michele continues to be used by the inmates of a prison. Hot wet fluid suddenly soaked the tops of my thighs and the crotch of my panties. I felt stream after stream of his creamy seed shoot against my silken hosed thighs and being to slowly run down my legs. My crot... Read full Story
✘Transensual✘ 2019-01-11 6,339 Stockings Crossdresser Bareback Creampie Fetish Blowjob Big Cock Lingerie domination Guy Fucks Shemale PRISON PRISON PUNK prison sex Prison Bitch
95%
Best session with a T Girl
I like T-Girls. Recently had a chance to go to Costa Rica for work. While I was there I decided to see what Costa Rica had to offer in this department. There is quite a good amount of girls to select from. I started texting this Tgirl and we set a time. I got ready and headed over. It was a Hotel th... Read full Story
horny.hiker 2019-04-30 14,756 Stockings Masturbation Creampie Shemale Fucks Guy Lingerie rimming Ass to Mouth escort ts no lube anal fuck just saliva
100%
Business trip
Craig and I were salesmen for the same company and on a trip together to woo new clients. The last thing I expected was that we would woo each other. It had been a long day and we went to our rooms to relax and unwind. After I had my room service and wanted to go over the proposals I realized Crai... Read full Story
Zöe from Kingston 2019-10-07 7,237 Crossdresser anal sex Cumshot Blowjob Lingerie cum in mouth
78%
My wonderful life with Patl : The dinner and after dinner
Suddenly the door bell rings, I went to the kitchen while Pat received Marie. Pat went with her to the garden and one they were sat she asked Marie what she would like to drink. Both agree on a Mojito, Pat came to the kitchen to order me to prepare 2 Mojito and to serve the tapas i have prepared. S... Read full Story
jperrot 2020-07-23 3,947 Amateur Shemale Fucks Guy threesome domination Sex Toys slave Ass to Mouth cum in mouth
100%
Bimini (part2)
Emily was introduced to me by my friend Jan at a night club. ‘Em’ is a 19 y/o t-girl and absolutely adorable figure and very sexy legs. Well after leaving me at the club with Emily, I had invited her to fly to Bimini the next day for a long weekend . If you read part 1 you will know. Waking up... Read full Story
Jon Paul 2021-04-19 3,483 Bareback Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale cum in mouth
100%
Sub to a Tranny story
One night as I was leaving a bar, I was approached by a beautiful woman who asked for my help. Not having plan I agreed. I followed her to her car and helped her take some stuff inside her apartment. After a couple minutes, I was about to leave when she offered me a cooked dinner. Well I am not ... Read full Story
77James 2021-10-07 5,182 Crossdresser Shemale Fucks Guy cum in mouth
50%
I'M A DIRTY WHORE EXPOSED TO PUBLIC HUMILIATION
There are people on porn sites who hunt down people like me and make me a world famous whore. They download all my photos that I publish. Sometimes they add descriptions to photos. They share my photos on all known porn sites, forums, chat rooms. More and more people have my photos. Some people edit... Read full Story
QUEEN HARLOT 2022-02-14 3,021 Big Tits Cumshot Blowjob public humiliation cum in mouth double anal whores humiliated whorehouse degrading degraded public humiliation
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 4,895 Amateur Bareback Shemale Fucks Guy threesome Shemale and Girl domination Guy Fucks Shemale slave Ass to Mouth double anal webcams punishment
100%
Just a Fantasy (one of many)
A lady, Sharon, calls me up to shoot a video for her business. The spokes-person, Paula, is a petite, beautiful Asian shemale with perfect c-cup size breasts. During the interview scene, I can see she's getting an erection, and then Sharon comes over and kneels down before Paula and spreads Paula's ... Read full Story
swollenrooster 2022-08-11 4,662 threesome Shemale and Girl suck-cock
100%
Surprise Ending (Part One)
My wife is the picture of professionalism from 8 to 5, but after hours she is a sexual dynamo who loves men and women. Throughout our relationship she has introduced several of her gal pals into our bedroom, hot tub, shower, etc...you get the idea. Anyway, two weeks ago she let me know that one o... Read full Story
Chantel13 2022-08-23 5,404 Crossdresser Amateur Group Sex Outdoor Bareback Shemale Fucks Guy threesome Big Cock Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth
80%
Outdoor Tranny Sluts Lust
I wake up really early one morning with my cock throbbing hard under the sheets. I got a white camisole on. Out of bed i go with a desire to vouyer and masturbate somewhere around my home. I'm home alone so i head out to my garden with my cock bouncing up, down & dripping cum. It's about 5am... Read full Story
Tracy Bel 2023-02-14 5,472 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
100%
Captain John’s Playmate
Alessia Travestita’s Adventures – Episode 1 – Captain John’s Playmate. It was forecast to be a gloriously warm and sunny day, clear blue skies with a gentle warm breeze from the South. So I decided to leave the town behind and head out into the countryside for the day, get some fresh air, toning ex... Read full Story
Alessia Travestita 2023-07-13 4,671 anal Crossdresser Bareback Blowjob blonde Big Cock Lingerie Guy Fucks Shemale Mature Ass to Mouth cum in mouth
100%
A Grand Awakening
By the time I completed my military service and returned home for civilian life, most of my friends from high school had completed university degrees and had relocated to other cities for lucrative career opportunities. I was absolutely delighted when I went to a popular disco club and found one of ... Read full Story
DRILLMASTER 2023-10-25 5,201 Shemale and Girl
50%
The first requirement of a deal with Dominatrix Persephone.e
There was a number of requirements before I even consider'd fucking that sissy ass, firstly, I expected dedication to be shown and to prove that the sissy could obey my orders, after a trial period, then I consider to force my big dick down the throat of the that sissy, and then fuck brutally and ex... Read full Story
Dominatrix Persephone 2024-06-21 983 anal solo Cumshot Masturbation Shemale Fucks Guy Big Cock Shemale and Girl domination Mature sissy shemale fucks shemale teen (18+)
100%
Dating my Sissy-sister (English)
You are wearing women's stockings and a thigh-high transparent top, the thin shoulder straps of which leave your arms and shoulders elegantly exposed! You're the real lil bunny to me in that girl outfit of yours... How about, should I teach the little one about the naughty girl? I throw you squir... Read full Story
LulaSissy 2024-07-10 402 anal Stockings Crossdresser Cumshot Bareback Fetish Big Cock Ladyboy Lingerie femboy shemale fucks shemale cum in mouth shemale fucks female
82%
Shemale cum in my pussy
Being a girl and only fucking me, I wondered what it was like to be with another girl. I am attracted to girls but the problem is that I really like the way that a cock makes me feel, especially when it fills my pussy with cum! The bigger the better! While sharing this dilemma with a friend she sugg... Read full Story
shemale lover 2015-06-29 14,325 cum oral dick
100%
Buffy the Shemale Vampire Slayer Part 11
Darkness had fallen upon the demon world. In the intermittent flashes of lightning that resulted from Willow's weather spell, the landscape was illuminated, and the horrible phallus-plants were revealed, writhing and thrashing. The cock-stalks within Buffy's mouth, cunt, and ass, and the hollow tubu... Read full Story
shemale lover 2011-08-21 4,212 asshole shemale Big Cock
80%
Buffy the Shemale Vampire Slayer Part 14
"Let's get this over with," Buffy suggested. "The sooner we start, the sooner I kick your demon ass." Baphomet smiled. "You will fuck the witch," he said, "while I fuck you." Buffy shook her head. "Willow's my best friend. I can't-" "Th... Read full Story
shemale lover 2011-08-23 5,030 anal sex asshole Big Cock
100%
Shemale Maid
Colleen rushed through the mansion's open gate and headed towards the main door. She opened her mini leather bag and searched frantically for her keys, although she knew she was hopelessly late. Was it her third or fourth unsuccessful attempt in a row to get there on time? Or had there been more? Oh... Read full Story
shemale lover 2011-09-13 5,107 licking sucking Big Cock swallowing
100%
Dressing Up for New Years
My wife and I attended a costume party every year to celebrate New Year's Eve. This year we decided to cross dress with her dressed as a man and me dressed as a woman. I put on her sexiest silkiest garments and she put on one of my nicest suits complete with a fedora. We had a blast at the party... Read full Story
shemale lover 2012-11-30 3,393 anal shemale Big Cock
95%
My First Time
I used to be a normal straight guy, or at least, so I thought. That was until I began exploring trans porn, I was so turned on by it, but thought it was wrong, I tried to fight it, but soon enough trans porn became the only porn I could get off to. I didn't know what to do with this obsession, ... Read full Story
handsome man 2018-06-07 21,921 Crossdresser Amateur Shemale Fucks Guy Sex Toys Homemade cum in mouth
84%
Becoming Zoe
My soon to be wife Annie had taken a job out of town and I only saw her every two weeks or so. I was so missing her. She and I had become long distance lovers. She was scheduled for a flight home on Friday night. I was going to pick up her son Zakk from his dorm and the two of us were going to p... Read full Story
Zöe from Kingston 2018-08-09 9,159 Stockings Teen (18+) Crossdresser Cumshot Bareback Blowjob blonde Big Cock Lingerie Mature cum in mouth
92%
My wife Gwen
My wife, what can I say she is tall and leggy with thick, natural wavy orange-red hair with beautiful porceline skin and just enough freckles to tell you she is a true ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen. From the time we... Read full Story
Zöe from Kingston 2019-01-08 7,603 Shemale Fucks Guy redhead Guy Fucks Shemale cum in mouth
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 11,813 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
50%
Giving Up My Freedom For A Fantasy
I arrived at his house early to get ready. I had specific instructions on what I was going to be wearing for the session and I had been locked up in chastity for nearly a month. He had left the door open for me, I entered and walked up the stairs and entered the bathroom. I was to take a shower and ... Read full Story
Sissysophie780 2019-07-08 4,840 anal sex Fetish Blowjob Ass to Mouth cum in mouth chastity blackmailed fingering.
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 16,076 Cumshot Blowjob Big Cock domination Interracial Homemade cum in mouth ladyboy ts thailand ladyboy shemale fuck guys virgin ass bottom boy bottom virgin
100%
Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
Regina10 2020-11-23 4,950 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
100%
Sissy Slut and Stepdads part 2
My mother kicked Frankie out and swore that he was the last loser she would ever date. She believed that we were still having sex, and she was right. Pure raw animal lust drove us, and It was even better when we sneaked and got. That nervous adrenaline mixed with my passion and made me super horny a... Read full Story
Regina10 2021-02-15 4,069 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to Mouth
100%
Sissie Slut's Windows of Womanhood
I flash back to my first time with a grownup adult at the tender age of16 . I was so nervous now that we were here in the motel room. I was nervous for so many reasons. I lied to my family and told them I was staying at a friend’s house. Instead, I'm here with Mr. Joey in a motel room and he was my... Read full Story
Regina10 2021-02-22 6,623 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
Mouthful
It was a typical Friday night and I was bored and a little drunk so started by watching some shemale porn which got me hard but wasn’t satisfying me deep down so I somewhat reluctantly went on bp and I say reluctantly because that’s how I justify it I wasn’t reluctant at all and actually wanted noti... Read full Story
Beesknees 2021-09-22 3,788 cum in mouth
80%
intimate Cousins
My favorite cousin and first lover, Billy, was just released from prison and I was anxious to see him. I am ecstatic that he is out, and I am thinking about all the past fun we had as I prepare to revisit those good times. Tommy knows all about my relationship with Billy and he understands my need t... Read full Story
Regina10 2022-05-13 6,002 Stockings Crossdresser Cumshot Masturbation Bareback Blowjob Big Cock Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
My story, more or less pt.2
So there I was, a boy with a desire. (Refer to pt.1 for context) A few months went by from the "initiation" and I've progressed quite a bit I have switched from shemale porn to femboy porn, to relate to the main characters more. I have also scoured every closet in desperate search f... Read full Story
Thigh_High_Boi 2022-12-23 5,236 Stockings Blowjob Ladyboy Lingerie Homemade self sucking cum in mouth
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 6,396 Group Sex Bareback Shemale Fucks Guy Big Cock domination big ass cum in mouth double anal
100%
Police House Call
My heart was beating a mile a minute when I heard the knock on my door. I was hoping that it might be Beau, or Larry, or if I’m lucky it would be Tom Cobb. He asked me to call him Tommy. I had been thinking about him recently. Bo and I had banged the night before, but I was as horny as ever. Larry w... Read full Story
Regina10 2024-04-19 3,456 Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Guy Fucks Shemale big ass femboy cum in mouth
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 3,139 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
93%
My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts :) I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use t... Read full Story
shemale lover 2015-01-19 6,253 blonde Big Cock Shemale and Girl
80%
Car sex with a shemale at the local drive in
I know for sure many guys are fascinated about fucking a shemale in a car. Well, this is what the story is about. The guy rammed shemale ass at the drive in. Happy reading! I pulled in with my radio up and saw the most beautiful girl walking right in front of my car. Her legs were long and brown ... Read full Story
shemale lover 2015-08-01 8,851 cock shemale fucking
92%
Another Transgender Story In Bob’s Life
I got into college right after my surgery. I changed my name into Danna and started my life at college as a ‘real’ girl. I didn’t want to have my transgender story follow me here. Anyway, I kept one picture of me as a boy and held it on my writing desk. I told people that it was... Read full Story
shemale lover 2016-05-14 5,113 pussy shemale Big Cock
100%
A Job in the Theatre Chapter 16
"Ted has invited me to his poker game" Paula let slip. "Oh really? Now that sounds interesting" Sarah said. "It will be if we come up with the right uniform. It's all boys so I am going to dress in some sort of domestic help type uniform. But of course it has to be the... Read full Story
shemale lover 2012-03-15 3,208 shemales anal sex Big Cock
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 6,198 anal sex Creampie shemale Big Cock
100%
Female Seduces a Shemale
As you are sitting in your computer chair , chatting online, I walk up behind you and softly massage your arms. I lean around and kiss you on the cheek. You turn your head to see who it is and I kiss you full on the lips. I walk around your chair and sit on your lap facing you, teasing you. I wink a... Read full Story
shemale lover 2012-07-06 2,770 Cumshot Blowjob Shemale and Girl cum swallowing handjob
93%
My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts. I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use the... Read full Story
shemale lover 2013-07-20 3,819 Cumshot Shemale and Girl big boobs handjob kissing
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 10,471 hardcore Cumshot Shemale and Girl oral sex kissing
91%
My first big cock
So I'm deciding to post a story about an experience I had about a year ago. Ill start with a little background about me, I'm a bi crossdresser 22 years old 5'8" 140lbs, newly exploring bottom, very passable crossdresser. And extremely selective. I tried an online dating site ... Read full Story
Cbosh40s 2015-03-31 10,468 anal Crossdresser hardcore Mature sissy
83%
Dressing with my cousin
My First Time When I was about 16, I would spend my Summer vacations, from school, at my Uncles’ house. My cousin and I would sleep in one bedroom, with two beds. He was three years older then me and always knew what we could do, to have fun. I looked up to him and wanted to be like him. We had... Read full Story
Topazsteve 2018-01-04 13,629 Stockings Teen (18+) Crossdresser Blowjob Lingerie cum in mouth
78%
What Lies Beneath (Part 2)
A RENDEZVOUS WITH SUZY – What Lies Beneath (Part 2) We woke in the morning, showered and dressed before going down to make breakfast. Mia must have planned this all with the girls in advance because she had packed a small suitcase with some day clothes for us both. The sun was streaming throu... Read full Story
The Adventures of Mia & Seth 2020-08-18 7,694 Group Sex Shemale Fucks Guy Shemale and Girl Interracial Latex toys
95%
Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
Ginger__57 2018-03-26 8,577 Stockings gangbang redhead domination Guy Fucks Shemale Ass to Mouth cum in mouth
93%
Nancy finds out...
Nancy’s stay with us that summer was going to prove even more eventful than ever I could have imagined. Even after having been caught wearing her things by the neighbour’s son, Lesley, which led to a whole new dimension in our friendship, as you’ll know if you’ve read “Caught in the Act…” Once ag... Read full Story
caroletv31 2018-04-23 8,577 Stockings Fetish Ladyboy Lingerie Shemale and Girl high heels cum in mouth