Sort by
Relevancy

Free Stories

100%
How I sucked my first shemale cock
It was the beginning of the year 2023, in January, three days after New Year's Eve. I was driving home in the morning from a party 100 miles away from my hometown. On the highway, after going half the distance, I received a notification from my dating app, and I was like, "Oh, a new match", I'll che... Read full Story
cock&heels69 2023-05-25 8,369 Stockings cock Masturbation sucking Blowjob shemale orgasm oral sex porn high heels cum shot first experience
100%
A Night of Makeup, Cock and Cum
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further,... Read full Story
shemale lover 2012-04-18 4,573 Cumshot jerking off domination Sex Toys cum swallowing
50%
"SISSIFIED": 12 JOURS DE SISSY-MAS
JOUR 1: mardi 25 C'était le matin de Noël quand j'ai entendu frapper à ma porte, ce qui était, bien sûr, très étrange à dix heures du matin. À midi, j'allais chez ma famille pour Noël, et j'avais rarement des visiteurs inattendus. Toujours dans ma robe, je me dirigeai vers la porte et fus s... Read full Story
Femboy 2021 2023-01-20 1,137 Stockings Crossdresser Amateur Fetish Blowjob Big Cock Lingerie domination Sex Toys cum in mouth
0%
Sexing It Up
What catches your eye when you're viewing sample pornographic video clips on the Internet? When it comes to sex, my own tastes are eclectic, although I find myself watching videos involving anal sex, bisexual threesomes, cum shots, gay males, lesbians, oral sex, public nudity, shemales, and spank... Read full Story
shemale lover 2011-11-26 4,125 interracial sex spanking
100%
Seduced At The Gloryhole
I love to write Erotica. For story requests please send me a private message or email noirenoire10@gmail.com Enjoy! Golden blonde hair that rested just past her shoulder, piercing blue eyes, full luscious red lips with colorful sleeves of tatoo’d arms. Wow, she was immaculate. She locked ey... Read full Story
therefill05 2020-12-10 9,098 Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale Interracial cum in mouth
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 31,056 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
50%
A Revenge Fuck
It had been a long day. I had fought the traffic after a miserable week to get home early and surprise my wife for what was to be a romantic weekend. But as I pulled up to the house my heart sank. I saw a bright red motorcycle in the drive way and something inside told me, "This isn't right!&qu... Read full Story
shemale lover 2012-06-03 10,962 shemale oral sex Interracial
60%
Teasing BIG BLACK COCKS at truck stops
I'm a white blonde bubble butt Tgirl living in Las Vegas and sometimes I go out and cruise the truck stops on I15 down south to I10. I do it at night and sometimes for a whole weekend in my mini van which has darkened windows. I love to get out of my mini van and walk around the back parking row at ... Read full Story
TgirlJill4BBC 2013-06-03 7,740 Stockings blonde Big Cock cum Lingerie Interracial Latex
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 16,384 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
93%
Chasity's white pussyboy
I led Chasity into the apartment. She was looking for a one bedroom, furnished place and had called about my ad in the newspaper. I hoped to rent this place quickly, then I would be full and could devote my time to some maintenance and repairs rather than showing places. I looked at the renta... Read full Story
blakepalmer 2020-06-08 15,716 Cumshot Bareback Blowjob Big Cock Ebony domination Interracial black shemale cum in mouth
80%
Tranny's First BBC
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 2012-03-28 3,889 tranny cum deepthroating Interracial handjob
50%
Polish Maid
'You want to get tips,' I explained to Marek, our Polish cleaner, 'You should be more a maid more like her.' Across the street was a girl of about 19, dressed in a fancy dress French maid's costume stumbling home, presumably from a party the night before. She was dressed in a tiny black dress, l... Read full Story
shemale lover 2012-09-01 4,639 Stockings Crossdresser Cumshot sucking heels
83%
Caught by my Sister
It was 10 o'clock on a Friday night and I was all alone in the house. My Mom, Erica, who was in her late 30's and recently divorced was enjoying her new found freedom by going out with he girlfriends. My sister, Jane, was out with her friends for the night and that left me alone as usual. My name... Read full Story
shemale lover 2012-06-17 11,920 first time cum oral sex crossdressing
100%
R Is for Rita
After my debts began to mount, college fees and all that, one of my mates from Brum suggested I try to earn a little extra cash. I was surprised when he told me how. He said he'd done it and ended up with a couple of hundred extra most weeks, sometimes just for an evening's work. "It's easy,... Read full Story
shemale lover 2012-09-05 5,120 Stockings Big Tits Masturbation Big Cock Mature
100%
Fantastic Weekend - First Touch
It finally worked! After a year of posting ads on Craigslist, and what I'd decided was my last attempt, I got results. It was short and to the point, "Panty Sub Seeks Oral Top." As is normally the case, I got a lot of one-line responses and picture requests, but buried in there were two gu... Read full Story
shemale lover 2012-08-31 3,183 Stockings Crossdresser Cumshot Blowjob Lingerie
100%
A Shemale Vacation Part 2
We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragem... Read full Story
shemale lover 2011-09-05 6,911 anal cumming cum swallowing
100%
Cuba
A trendy upscale bar in La Jolla on a warm Friday night was not what I had planned. It's not usually my crowd, but a friend asked me to join him and I didn't really have any plans for the evening. What the hell I figured, I might even meet someone interesting. It's a warm summer evening with a li... Read full Story
shemale lover 2011-10-24 3,478 Stockings Cumshot oral
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 6,403 Cumshot Fetish oral sex cum swallowing
100%
Always Be Closing
Hi, my name is Tom Jacobson. I am 23 years old 5'9" with light brown hair and a slim build. I currently work as a software engineer for a rapidly growing outsourcing company. This is my first job out of college, but I've already been promoted twice. I am now the lead engineer on my team, which ... Read full Story
shemale lover 2012-10-17 3,443 Cumshot oral cum swallowing
78%
Anal Therapy
My new psychiatrist wasn't at all what I expected. When I saw her name in the phone book, I pictured a dowdy old lady wearing a long, gray skirt and flat-soled shoes. What else could Dr. Edith Doss look like? I got my answer when a tall, leggy redhead stepped into the waiting room. A tight, black... Read full Story
shemale lover 2012-11-24 7,543 anal Fetish cum crossdressing
87%
THE ATTIC NOVEMBER 7
THE ATTIC NOVEMBER 7 – PART 1 THE JOURNEY AND GETTING READY. Susan had not had the opportunity to make the journey to the Attic dolled up to the nines so she made do with just wearing her black and pink lingerie under the hideous drab stuff (yuck). Having arrived early and parked up, she relaxed ... Read full Story
sexysusang 2018-03-09 5,734 Amateur Group Sex Bareback Blowjob Guy Fucks Shemale cum in mouth
95%
Jordan's First
My name is Jason, I am a 33 year old road worker. The pay is okay but I never had much more than what I needed to live comfortably. I was hoping to save up for a nice vacation and decided the best way to do that was to take on a roommate. I live in a decent sized two bedroom apartment and the seco... Read full Story
Hydra1979 2019-01-25 9,539 Stockings Crossdresser Masturbation Blowjob Lingerie
71%
A Night of Makeup, Cock and Cum - froam Annamalice
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further, I... Read full Story
shemale lover 2011-11-21 4,989 shemales Group Sex Fetish
100%
Tony to Tanya Part 2
Tony woke up on Saturday morning feeling excited without knowing exactly why. He tried to sit up, but his left arm was pinned down by Sarah's body. This was normal for a Saturday morning, since she tended to sleep at Tony's house on Fridays. The reason he was excited suddenly hit him. On Tuesday,... Read full Story
shemale lover 2011-12-19 2,999 sucking transsexual cum swallowing
76%
Roommate
It was freshman year of college. The college had just started a new coed dorm which I signed up for. On the first day, I was excited to see who my roommate was. I was sitting on my bed reading a book, and I heard the doornob turn. It was my roommate. She was medium height, dark skinned, red hair, sh... Read full Story
shemale lover 2012-05-01 11,982 oral sex cum swallowing 69 position crossdressing
100%
Bob and Carol and Gemma and Alice?
I sat there, in the kitchen, suddenly very nervous again. The previous half-hour had started out nerve-racking enough but I had settled, more quickly than I had imagined. Carol hadn't laughed, she had been kind, and interested, and considerate, and she had listened and asked intelligent questions. B... Read full Story
shemale lover 2012-07-22 3,553 first time Cumshot oral sex cum swallowing
90%
Bethany's Secret Part 2
-3- Before beginning my story about what happened to me the week before Christmas, I should explain what had happened during the past few months. Early in my senior year of high school, I had met a gorgeous girl named Bethany who became my girlfriend. On the day of our four month anniversary, we ... Read full Story
shemale lover 2011-12-18 3,831 licking cum fingering
100%
Becoming A She-Males Bitch Part 2
After last nights ordeal I was given something to drink and taken to a bedroom upstairs. What I drank must have had some kind of drug in it because I was knocked out. I bet I was asleep in just a couple of minutes. I barely even remember lying down. When I woke up I was naked, sore as hell and fe... Read full Story
shemale lover 2012-01-04 8,622 cum oral domination
100%
Blushing Bride Chapter 3
"Those pretty white panties are appropriate given that it's going to be your first time," David, my friend and former flatmate said, lifting up the white skirt of the wedding dress I was wearing and running his hand over the white lacy french knickers that I wore beneath, the feel of his h... Read full Story
shemale lover 2012-07-21 4,529 cum Lingerie oral sex crossdressing
76%
Brotherly Love, Sisterly Love
RICHARD My brother and I were especially close, as twins often are. We shared everything, including all our thoughts, feelings, experiences and desires. Even though we were eighteen, we still shared a bedroom too. It wasn't like there were things that we kept private from each other, it was the t... Read full Story
shemale lover 2012-09-28 6,436 sucking cum swallowing crossdressing
100%
Camming down the rabbit hole Ch5
I was jolted out of my sleep by the phone on my bedside table vibrating, bleary eyed I picked it up and saw a message from the couriers that a package would be delivered today around 4pm. The realisation that this was the package I had been waiting for and I could finally wear something else in my s... Read full Story
Dani_does_Dallas 2021-09-29 4,808 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade cum in mouth webcams
50%
Pris travesti!
J'étais sur le lit avec un vibromasseur coincé dans le cul et le soutien-gorge de ma copine attaché à ma poitrine quand elle rentrait tôt du travail. Elle m'a surpris en train de chercher la télécommande pour éteindre le porno cum shot que j'avais joué à la télévision. «C'est quoi ce bordel? elle... Read full Story
Femboy 2021 2023-01-24 481 Stockings Crossdresser Fetish Big Cock Lingerie Guy Fucks Shemale
100%
My Wonderful Secret Chapter 2
I felt like I was going to explode inside. Such was the anxiety, excitement, fear, horror, and arousal I was experiencing. I had no one to talk about it with. I had no one to tell that I had been caught dressed as a girl. I had no one to share the secret that Mark had taken me home and treated me li... Read full Story
shemale lover 2012-09-09 3,568 Stockings Crossdresser Cumshot Masturbation heels
100%
Whore Street
It was just too many nights, that I had not been fucked, so I decided for the best way of hunting for cocks, another night as a hooker. First the outfit. Tight pink half shirt that zipped in the front, padded leather bra with "B" cups, black leather mini skirt and thigh high black fishn... Read full Story
shemale lover 2012-11-09 3,788 cum oral sex deepthroating swallowing
100%
CD Jinn and Football Jerry
Last weekend my college football team was throwing a party during their off season as a way to relax and take their minds off school and football. I am Jinn a very limited experienced Cross Dresser. I have only ever experienced one man and one strap-on girl. The man was Jerry he was a college foot... Read full Story
Jinn.V23 2014-01-27 5,239 ass Stockings Cumshot Lingerie ass fucking cd
100%
The Twink and the Bear
He stood there, slowly rubbing his hardened cock in the confines of the public toilet cubicle, trousers around his ankles, his legs adorned in black nylon stockings, held in place by the straps of his delicately laced suspender belt. It was so naughty to be playing with himself in a public place, wi... Read full Story
Daddybear71 2023-03-28 4,313 Crossdresser Blowjob Big Cock Mature cum in mouth
100%
Olivia and Katie
After our first meeting me and Olivia became fast friends. We would go shopping, do lunch, check out a movie, pretty much the stuff that girlfriends do. It was lots of fun and most of the time we did these activities dressed up all cute or sexy. Well there was one thing that has eluded me and Olivia... Read full Story
shemale lover 2012-09-06 2,241 Stockings Blowjob jerking cum swallowing
40%
First Sexual Crossdress Experience
How my secretary found out I'm a bi TV and how me and my TV friend educate her into some of the more zany aspects of TV sex. *** As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front o... Read full Story
shemale lover 2012-09-27 5,441 first time Fetish cum oral crossdressing nylon
100%
First Time as a Cum Slut Chapter 3
About a week later I phoned the number Charlie left and we spoke, he asked me if I had enjoyed our last meeting, "I loved it Charlie and want to do it again soon." Charlie replied, "I am glad to hear that as will a couple more friends of mine. What are you wearing right now?" ... Read full Story
shemale lover 2012-10-05 3,507 Cumshot oral sex cum swallowing
72%
Mistress Carol transforms me into a cum slut
I sat on my car and put on my heels, smoothed down my mini skirt and checked my hair growing out nicely and currently in a blonde bob. I was breathing fast and felt my small, c size, breasts move up and down. My nipples were erect and sensitive the piercings quivered slightly in my halter top. Decid... Read full Story
shemale lover 2013-05-17 15,458 Stockings Cumshot dildo fingering domination swallowing
100%
Wet & Messy Sex
It was the text I'd been waiting for for ages. 'I'm back.' it said. Anish, one of the kinkiest guys I've ever met had finally decided to return to his holiday home, just a few minutes away from where I live. He's a well off Asian businessman and has a lovely place to entertain. It's been a while sin... Read full Story
kiwicd 2022-04-27 3,261 Crossdresser Amateur Cumshot Creampie cum in mouth golden shower
100%
Linda and Cum on Heels
I was told by a cute guy today they would love to cum in a pair of my strappy heels............this was my answer to him. (I hope you enjoy what happened in what could have been unfortunate circumstances) Actually a person did. I had picked him up from the Lincoln University area and we went off ... Read full Story
Linda Tiffany Vista 2024-05-07 910 Stockings Crossdresser Amateur Blowjob blonde
100%
Linda and Cum on Heels
I was told by a cute guy today they would love to cum in a pair of my strappy heels............this was my answer to him. (I hope you enjoy what happened in what could have been unfortunate circumstances) Actually a person did. I had picked him up from the Lincoln University area and we went off ... Read full Story
Linda Tiffany Vista 2024-05-07 1,012 Stockings Crossdresser Amateur blonde Lingerie cum in mouth
25%
Westwood Bound Cum Slut
After many months of internet relations I was on my way out west. There to meet the gurl I had longed to finally get to be with, you see Jill was the cd I had been talking to all these months exchanging stories of things we could do to each other, to bring the pleasures to each of us we really ne... Read full Story
shemale lover 2011-11-03 2,816 Blowjob shemale cum
100%
Becoming Bernard's Wife
I put an ad on Adult Friend Finder, thinking I'm never going to meet anyone here but was I wrong. I am in my 30's, tall and slender, long brown hair and practically hairless everywhere else on my body. I was looking for whatever and was very curious. Just out of a relationship with a woman for 8 ... Read full Story
shemale lover 2012-11-07 3,527 Fetish cum Lingerie
100%
Angel Chapter 9
Angel Jones had been working as a teller at the big London bank for over a year, and her duties had become almost routine to her. It didn't seem like a rut, because she enjoyed her work, and it paid well enough to meet her needs. She enjoyed a good relationship with her fellow tellers, mostly attrac... Read full Story
shemale lover 2012-12-02 4,115 cum fuck oral
77%
Westward bound cum slut
After many months of internet relations I was on my way out west. There to meet the gurl I had longed to finally get to be with, you see Jill was the cd I had been talking to all these months exchanging stories of things we could do to each other, to bring the pleasures to each of us we really ne... Read full Story
shemale lover 2012-12-16 3,412 cum oral swallowing kissing
100%
VOGLIO STUPIRE PAOLA
Un' altro sabato sera è arrivato ed io mi preparo per quello che ormai è diventato un appuntamento fisso. Faccio la doccia, mi rado i peli del mio inguine, una sissy deve essere sempre perfettamente depilata! Questa volta voglio essere io a stupire Paola. Arriverò da lei già pronta, truccata e se... Read full Story
Sissy Mari 2022-02-21 1,250 Stockings Crossdresser Amateur Lingerie sissy shemale + shemale sissy slut cum shot sissy crossdresser
75%
The Succubus with a Cock
His cock felt so good between my lips. I savored every inch with such great passion he moaned and fucked my head farther down his shaft. I gagged many times but I was getting better at deepthroating. His balls were coated with my saliva, and soon the couch we were sitting on became wet to. I really ... Read full Story
shemale lover 2012-05-18 7,863 hardcore anal sex Cumshot cum swallowing
94%
Crossing lines
It had always been a fantasy of mine. I have very feminine features and long natural straight brown hair. Which recently I had shortened to chin length. I have been dressing in womens clothing now for many months and had decided that this was the night in which I get made up totally and head ou... Read full Story
Zöe from Kingston 2019-02-04 10,894 Stockings Crossdresser Cumshot Outdoor Bareback Shemale Fucks Guy Blowjob Big Cock Ebony Guy Fucks Shemale Interracial
100%
Buying Heels
I have to know what it feels like to wear heels. I have the house to myself tonight and I'm going to play. I already have panties but want to buy some new ones. My wife bought me a black, frilly thong which I wore for her when we went out one night; I also have a cheap, supermarket pair of sheer ... Read full Story
shemale lover 2012-09-30 4,535 Stockings Cumshot oral sex crossdressing
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 8,287 anal sex Ebony oral sex Interracial kissing
83%
PF's Black Romp and JoyceLynn's Awakenin
When my wife and I first met, our sex life was fantastic! She was a very sexual lady and always made herself available. She usually wore stockings and garter belt or thigh highs, high heel sandals, and something that was sexy and suggestive. We made love and had sex in every room of the house, inclu... Read full Story
shemale lover 2012-05-17 4,166 Fetish Interracial Sex Toys
50%
QUELQUE CHOSE DE NOUVEAU ⚧️ ⚧️
e me suis transformé en un fétiche de travestissement de poule mouillée de Tumblr à l'époque. J'avais l'habitude de m'habiller avec la lingerie de ma femme, de regarder sissy hypno, de discuter avec des hommes. Mais j'avais besoin de plus. Donc, comme "cadeau gag" parce que je n'étais pas du tout sé... Read full Story
Femboy 2021 2023-03-25 918 Stockings Blowjob Lingerie Interracial feminisation gloryhole strapon fuck plug anal cage de chateté domination fémi poule mouillé salope forcé a me protitué
87%
A Picture Perfect Sissy
"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... Read full Story
shemale lover 2012-05-27 10,469 Stockings anal sex Fetish Interracial sissy
100%
My Fantasy Story
My first time, Sissy Cuckold for BBC After ten years of marriage, my wife and I wanted more. First we went to some strip clubs together. One night one of the girls my wife liked told us about a swingers club. So we gave it a try. Best decision we'd ever made. We went, at first just wallflowers, ... Read full Story
Mikky666 2020-10-09 9,531 blonde Big Cock Interracial Ass to Mouth