Sort by
Relevancy

Free Stories

100%
My shemale GF Part 5
If you read my last story, you know that Ashley said she was going to dominate me, well that's exactly what she did. So today after work I went back to Christy's place not actually thinking she was going to fuck me. Christy was home before me and asked me to clean up, which is the universal sign ... Read full Story
shemale lover 2012-07-22 3,161 anal sex facial cum swallowing sissy
100%
Jenny, Melissa and Me
I’m watching you on the screen, Jenny, as you pull down your pretty nylon panties with the floral prints and spread your legs. Your brunette hair hangs down around your lovely eighteen year old face, smiling as your labia open wide and you begin to rub your clitoris, all the while smiling, and... Read full Story
shemale lover 2012-10-28 2,669 anal Group Sex Fetish oral
100%
First Time Sex With Tranny
Wow - if you have ever wondered what it would be like to be with a TS girl, this would be a great place to start. Just got this from a “friend” of mine who wanted to write about his first TSgirl experience. Can’t say for sure if it’s 100% true, but who cares? I do know that they were together so ... Read full Story
sach 2015-11-16 8,104 first time tranny suck stroking mutual sex
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 13,428 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
50%
I and the old man's story 后面中文
I am from Chongqing, a boy who loves his father. When I was young, my neighbor aunt always said I looked like my sister, like a beautiful girl. At that time, my family was relatively poor. My Sister, my parents, and my family of four lived in public rental housing of less than 30 square meters. Star... Read full Story
Oldslut Sissy 2024-04-15 9,439 Crossdresser Amateur Masturbation Asian Ladyboy Guy Fucks Shemale Mature small cock Homemade sissy chinese teen (18+)
50%
Being Shemale
Every night I wear make up and dress up in a sexy lingerie. I stand in my balcony late night trying to lure men and women driving on the road. Last night a truck driver stopped near my house to inspect his vehicle. During his inspection he suddenly saw a long legged booty women in the balcony inf... Read full Story
babydriver 2024-06-04 3,791 Stockings Crossdresser solo Outdoor Ebony Asian Ladyboy Lingerie big ass sissy femboy
85%
Interracial Encounter With Black Shemale
Me and a buddy decided to go see a rock concert at the Great Western Forum (that's what the Staples Center was called back then). I was 21 at the time, horny all the time and could never get enough pussy. So we go to the concert in our own cars since his brother lived nearby and he was going ther... Read full Story
tgirlloverme 2015-01-15 11,418 Interracial
69%
From Mob to Shemale
Two years ago, I was a member of the Ciccio family in Chicago. I wasn't very high up in the organization, because I wasn't Italian. I had made my way up through the ranks, however, and was making a pretty good living. I had everything I wanted, got all the girls I wanted, and did just about ... Read full Story
shemale lover 2011-10-29 10,715 orgasm facial oral sex
100%
Emily and Steve Part 2
I was sitting at my desk with my office phone pressed against my ear, supporting myself with my left hand and trying not to fall asleep. On the other end, someone from Gooseman Paper Products droned on about terms of payment and invoice formats. It was a typical Thursday afternoon. Just then, an ... Read full Story
shemale lover 2012-04-06 3,184 Crossdresser anal sex Cumshot blonde rimjob
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 3,725 anal sex oral sex
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 3,697 anal shemale cum jerking oral
90%
2nd Shemale experience
All my stories are based on my own experiences After my first experience with a shemale (also pasted on here, She was a He) I wanted to have a second, but this time for me to knowingly know what I was about to do. I trolled chat rooms and dating sites for a few months, getting to know a few gi... Read full Story
shemale lover 2014-07-17 4,114 Small Tits Cumshot shemale Lingerie cum swallowing
90%
Sissy story and 1st meet humiliation
I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before tal... Read full Story
shemale lover 2014-11-19 25,918 ass Fetish domination cd sissy
80%
Owned sissy girl
I met the mature dominant couple that I now call Mummy & Daddy on the internet. Their ad said they were looking for a full-time live-in mature sissy plaything. After we made contact they invited me to their house. I was instructed to bring any sissy clothes with me and to refrain from orgasm for... Read full Story
Andrellina 2015-09-23 29,418 anal ass rimming cd sissy
88%
Very Impatient on a sex fanstay
Are you ready for this Mish?" "Not really but it's too late to back out now." I stood in a dark alley before a metal door shaking with both anxiety and the cold, waiting for the door slot to open and for the night to begin. I wouldn't admit it to my friend Simone but secretly I hoped we would ... Read full Story
ASSEaster5678 2018-07-10 10,999 Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale Mature
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 2,981 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
100%
My First Visit to a CD Sex Club
Feb 16 Time off work booked, nice new wig, false nails & lashes, & a nice new sexy red bra & panties from Ann Summers & I'm all ready for a fab day at Happy Mondays @ lovejoys on the 22nd. I'm really looking forward to meeting SuzieStern & all the other girls. Its been way too long since I last m... Read full Story
Lacy-Rose 2024-09-02 2,087 Crossdresser Amateur Group Sex Cumshot Blowjob gangbang cum in mouth
87%
Shemale First Time
First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married... Read full Story
shemale lover 2011-08-24 9,457 first time asshole shemale
66%
Electric Shock
I'm glad you enjoyed my story. I have been dressing for many years, and it's only lately that I thought I'd share some of my experiences with other cd's I am NOT convincing; all the stories in Nifty seem to be by gorgeous she-males who cannot be distinguished from the real thing. Much as I woul... Read full Story
shemale lover 2011-08-26 2,824 shemales anal sex Big Tits
100%
Joanna's day and night with Tania xxx
It took quite some planning, after our last meet in the lay-by, but at long last we had both been able to get away at the same time. We, well actually Tania, had arranged our meet to be at the Premier Inn at Witcombe, just south of Cheltenham and just of the A46. Tania was arriving just after lunch ... Read full Story
Joannacd1 2012-01-06 3,810 sex crossdressing
71%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2012-03-16 2,981 cum oral sex swallowing
93%
Sissy schoolgirl and her black daddy
I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning... It was summer time. As always I spent m... Read full Story
shemale lover 2013-06-22 40,135 Teen (18+) Bareback Creampie Lingerie ass fucking Interracial cd
96%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2014-11-25 10,340 tranny suck Creampie Shemale Fucks Guy ass fucking 69
80%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2014-12-03 6,653 tranny suck Creampie Shemale Fucks Guy ass fucking 69
100%
My Life as a Shemale Part3
The next year would become the strangest and the most turbulent of my life, I will have to write more chapters just to get it all in. What came next was my transformation, even though it was becoming more clear to Tim, Sam and I that I was transgender from the onset. Sam came and saw me more ofte... Read full Story
shemale lover 2015-02-19 2,883 tranny Cumshot shemale ass fucking sperm
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 7,633 Group Sex shemale vampire
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 34,469 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
33%
sex
Hello I am mahan Very handsome and curious. The date goes back to last year. With our sister, Sepehr, from childhood, we were on the floor of Khalmun Arshida's daughter. One day we went out with the scene, Arshida called me and his parents went to Istanbul and that lone. And asked us to go over the... Read full Story
sima2000 2019-04-18 3,801 Amateur Big Tits Creampie gangbang Shemale and Girl pov double anal
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 5,222 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
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 3,549 Crossdresser Amateur Group Sex Cumshot Shemale Fucks Guy threesome Ladyboy Lingerie Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
100%
sex-agenarian's onanic lust
An onanic lust of a sex-agenarian that I am; I'M IN BIG HEAT; it's the season of bodily reunions in nature... I'm like an elephant(e) waiting to be satisfied. My cloaca is starting to titillate at the mere sight (look hah!) of a guy's swollen crotch on the street... I activated all my sensors to sa... Read full Story
hippocampus_171 2024-03-09 4,515 anal solo Amateur Masturbation Creampie Sex Toys Mature small cock
100%
Being Shemale Part II
After sometime the driver left. Night Two I was again ready by 10 Pm as usual wearing make up and sexy night outfit. My push up bra helped my breast look very attractive looked perfect with my slim body I was standing as usual in the balcony around 11 PM and the driver stopped by again.... Read full Story
babydriver 2024-06-04 3,659 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy Lingerie domination small cock big ass Frottage sissy femboy
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 2,964 anal solo Cumshot Masturbation Shemale Fucks Guy Big Cock Shemale and Girl domination Mature sissy shemale fucks shemale teen (18+)
97%
Shemale Runner
This is based on a real life experience and is about consenting adults engaging in sexual activities, if you are offended by such themes as shemales then do not read on any further. I try to stay fit, I run every day after work for an hour. There is an old dirt track walking path that links fa... Read full Story
shemale lover 2011-09-11 9,501 anal facial oral sex
100%
Club sex the 25yo
There’s a very special private club around, it’d meetings take place in a very secret place. It takes a lot to gain membership. You have to either have a lot of money AND a friend in the club OR you have to take part in the ceremonies for at least a year. Also you have to be willing to b... Read full Story
shemale lover 2011-12-10 5,201 anal Group Sex lesbian
100%
Marilyn's Family Reunion
The warm humid September air blew through the windows of the speeding silver Nissan Pathfinder as it cruised along the Belt Parkway. With the Marshall Mathers LP blaring out the stereo, Sharilynn whipped her SUV along as the wind whipped her ponytail and her plain white t-shirt. As little Mai lay sl... Read full Story
shemale lover 2012-01-02 4,626 sucking Shemale and Girl cum swallowing
100%
The Triple X cocktail - Wife Shares Shemale With H
"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an ... Read full Story
shemale lover 2012-02-21 3,927 Group Sex Creampie face fucking tit licking
100%
Fulfilling A Girl's Male Fantasy Part 2
Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a ... Read full Story
shemale lover 2012-04-04 4,579 Stockings anal sex Group Sex Blowjob
60%
Booty and the Blue Pill
This is my account of the first time I took a Viagra. At 40 years old I have thankfully never had to go that route but you know curiosity killed the cat. Or in this case opened up my ass! After telling the guys at work how I planned on staying in while my wife was out of town visiting her sister,... Read full Story
shemale lover 2012-04-15 4,426 Cumshot sucking jerking gangbang Interracial
85%
Whores and Pimps - Part I
Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... Read full Story
shemale lover 2012-05-13 8,252 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
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 9,561 Cumshot sucking blonde ass fucking Guy Fucks Shemale
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 7,166 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 48,444 Cumshot Shemale Fucks Guy Big Cock Lingerie ass fucking ass licking big boobs
100%
CD new sex friend
Tyrone is a tall skinny black guy 22 years old and his Mel is short and pudgy. I am an older white sissy. I wear female clothing under my regular clothes all the time. Saturday morning I went to the small house they rent and brought an overnight bag. Tyrone opened the door and I walked in. I s... Read full Story
shemale lover 2014-07-31 5,107 Creampie ass fucking ass licking Interracial cd
94%
In Love with a Shemale
I was out one night in a busy club and I couldn't help to notice this one girl staring at me constantly. She was incredible wearing a tight little skirt showing off her long legs with an amazing smile and a very cute face. I planned my move and went to the bar when she did and she started talki... Read full Story
curiousshemalelover 2014-11-29 10,525 tranny suck Shemale Fucks Guy ass fucking domination oral sex
100%
My Life as a Shemale Part8
It was on my way home when I decided not to tell Tim about Sin. This was very private and it was already bad enough that I knew, also, I had no idea what Tim might say or do. I did want to stay friends with her, now more than ever. It was friday morning, the day after Sin was ****d and I was eager ... Read full Story
shemale lover 2015-02-27 3,961 tranny licking Big Cock Lingerie stroking
66%
First time with a shemale
Ive always been turned on by shemales,why i dont know. I always wanted to fuck one for some reason big titty shemales that look like a woman just turned me on. There is a shemale in my town i ran into a couple times, I finnally found out her name and looked her up on facebook. She is a beautiful ebo... Read full Story
Tranny Warrior 2015-11-16 4,266 first time tranny sucking jerking fingering fake tits ebony ts
27%
I have been out dune by my little brother by a big difference hi
I am 32 years old and my lady who was 46 and my little brother who was just 14 years old then wanted to have some fun and get my woman who was just the right for him he was just out of his mind about her and I was like I'm all about it and I was thinking that I was going to be the big cock an h... Read full Story
Not long but hard 2017-10-19 6,134 Big Tits gangbang Shemale and Girl Solo Shemale Cartoon shemale + shemale Wow.
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 4,850 Small Tits Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
Alessia and I shock our guest!
Alessia was sat on the couch and I was sitting on the soft fur rug between her legs. We were relaxing and recovering watching an old movie. My ass was still feeling hot and wet after Alessia had earlier fucked me hard and long and I had returned the favour to her. But that is another dream! So back... Read full Story
Alessia Travestita 2023-01-12 4,718 Crossdresser Blowjob blonde Big Cock Guy Fucks Shemale Mature cum in mouth
66%
BBC Takes sissy slut and uses her properly.
I'm a dominate alpha man who loves to humiliate sissy girls and punish them when they aren't perfect submissive sluts. I want them to worship my big black cock and beg me to let them lick it then grab them by their hair and shove my cock deep inside their throat, making them gag. I like filling siss... Read full Story
lemondropz 2023-11-27 7,921 anal Crossdresser Bareback Creampie Big Cock domination Interracial sissy submission femboy bbc Ass to Mouth chastity
56%
First black T-girl
I've been wondering what to write about lately. I've received a request to write about me and my sister, but that is a road I might have trouble going down. Today I was thinking about my bi-sexual stripper girlfriend from the past, who loved bringing home other strippers (mostly lesbians) for some h... Read full Story
bigtranslover 2014-01-01 7,316 first time shemales interracial sex
96%
A Trannie takes her first big black cock
Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me. Normally it’s just the usual crowd of guys but several weeks a... Read full Story
shemale lover 2014-12-27 8,653 shemales gay male interracial sex
100%
Shemale On Webcam Made Me Cum
It wasn't enough for me - regular porn, regular girls... I felt like I was losing it, not having the only thing I really desired: a shemale. But I was new in that world, not knowing where to go, where to look, so I decided it was better to see shemale on webcam first. I searched the internet and ... Read full Story
shemale lover 2015-12-31 4,145 Big Tits Cumshot shemale
42%
Shemale Free Chat And Sex Adventures
It was another day at work at the mall. Being a security guard wasn't exactly the most exciting job in the world: I'd sit all and maybe get a few calls about some punk kids trying to steal DVDs. I felt like my talents were wasted there - I used to be a competitive bodybuilder, evening getting into f... Read full Story
shemale lover 2016-04-24 3,988 anal transsexual ass licking
58%
Porno Mobile Shemale Video
I have been always turned on by shemales, but somehow I couldn't find any that would like to be with me. That's why I was always watching shemale movies and I even had several porno mobile shemale videos on my android. I was always fascinated by the fact that I could sleep with shemale and touch her... Read full Story
shemale lover 2016-04-28 11,335 asshole Big Cock oral sex