Sort by
Relevancy

Free Stories

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 13,721 Masturbation cum orgasm cumshots prostate
84%
SUMMER VACATION by Spanky de Bautumn
In our house, it was a well-known secret that my mother kept her change in the top drawer of her dresser. The same drawer she kept her slips, chemises, panties, and all other satin, nylon, or lacy ladies undergarments. During the summer, my brother and I would run to that wondrous drawer when... Read full Story
SpankydeBautumn 2021-01-22 12,531 Small Tits Crossdresser Cumshot Masturbation Fetish Blowjob Lingerie Shemale and Girl cum in mouth
100%
Camming down the rabbit hole Ch6
In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... Read full Story
Dani_does_Dallas 2021-10-11 4,785 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
100%
My afternoon getting some (true story) BB creampie
It was a Sunday afternoon and I was emailing with a guy I just met on craigs list. I was having a few drinks while starting to get in the mood. We exchanged phone numbers had a little chit chat on the phone, he told me he was straight but always wanted to experience a TS. Well this is the type t... Read full Story
shemale lover 2011-10-16 6,414 cum dildo oral rimming
100%
The Bounty Hunter - Working With A Partner
My boss, Carl Bronson, was pleased with the results of my first case, and gave me more jobs over the next few months. In each, I learned from my mistakes and was able to apprehend my target. Even better, I was finally earning some good money and doing something that was worthwhile and, more importan... Read full Story
shemale lover 2012-01-29 4,373 sucking Creampie cum fucking
88%
Carla Chapter 2
This is a grown up story for grown up people. If you're under 18 please don't read this. If you don't like to read stories about transsexual people, please don't read on. I have spent some time writing this story so please do not reproduce this in part or whole without my permission. I am happy to g... Read full Story
shemale lover 2012-03-07 3,956 anal sex Creampie oral sex 69 position
100%
A Strong Man at Work
In life, some people seem to get pleasure out of pissing others off. I think you know what I mean. We've all been there. The first time I laid eyes upon Joan, I thought she was a low-class, boring and obnoxious person. Where I come from, people like that are pretty common. Who am I? Stefan. A tall a... Read full Story
shemale lover 2012-07-05 3,426 anal Creampie shemale
100%
Alexis Chapter 4
Thursday rolls around, and Mr. Hughes tells me to stay after class. As usual, he walks into the supply closet when all of the students have left, and I diligently follow him. I suck his cock for a little bit, and then he says that he wants to fuck me. I nod my head and stand up, looking him in the e... Read full Story
shemale lover 2012-10-06 3,586 Creampie ass fucking oral sex
72%
From Tomboy To Boy
Mike Flannigan is a wealthy man who, at the age of forty, could certainly afford to retire from his law firm with a lot of money to spend. He had always been the most driven person in his family. He was born in 1951 in Dallas and lived there for most of his life. His parents were a working-class cou... Read full Story
shemale lover 2012-12-03 4,155 anal sex sucking Creampie
100%
Castro - shemale goddes
Nobody would have believed the scene was true, her slender, smooth and tanned legs crossed in such a deliberately provocative way as to reveal a glimpse of crisp white panties. Her tightly fitting, classically styled little black dress cut to ensure firm large breasts were displayed to maximum effec... Read full Story
Law12 2018-03-04 4,980 Masturbation Bareback Creampie Ass to Mouth cum in mouth Supernatural
100%
Liberty in Lisbon Part 2
So here I was walking down the Av da Liberdade feeling very pleased with myself. I had just thoroughly enjoyed an experience I thought would only ever be in my dreams and, the best part, there was more to come [cum]. In fact I found myself humming the 59th Street Bridge Song. Life I love you feeling... Read full Story
Rusty12 2019-07-31 4,853 Amateur Masturbation Bareback Creampie Shemale Fucks Guy cumming
100%
Booty call :)
Your cock pounds my ass harder, my cheeks rippling with every deep thrust you give. The sounds of our moans and your balls slapping as you fuck me hard is suddenly broken by the ringing of your phone........... And you wake up. It's 2:30am and I've just finished work. As arranged, I'm giving... Read full Story
BalkanLoco91Ri 2019-08-26 5,096 Teen (18+) Amateur Cumshot Masturbation Bareback Creampie Blowjob Big Cock domination Sex Toys Homemade pov Ass to Mouth cum in mouth
100%
First fuck in public ;)
You’re only wearing a coat, I find a place where, I can kiss you then slide my hand between the flaps of your coat. I expose your breasts and slide my hand down across your tummy down to your pussy. My fingers start to explore your soft bush, working there way to your soft pink lips surrounding your... Read full Story
BalkanLoco91Ri 2019-08-26 3,747 Stockings Teen (18+) Amateur Big Tits Cumshot Outdoor Masturbation Bareback Creampie Blowjob Big Cock Uniform domination Homemade pov cum in mouth
80%
Transsexual Savage
John had walked for eleven days. He was headed towards Fort Winston at the Hiat River, and he still had about three days ahead of him. The Hiat River was the natural border that separated the civilized world, where he came from, and the savage and brutal wilderness, where the natives lived and pract... Read full Story
Anal Orgasm 2020-07-10 6,203 Big Tits Outdoor Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Guy Fucks Shemale
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 6,541 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
TG Girlfriend moves in
Monday morning 6:00 am and I am just awakening, and I realize a naked body beside me has her arm around me, we are both naked. My wife Lydia is out of town to a seminar, and this adorable brunette perky tits and lovely eyebrows, beautiful lips slightly pink, sleeping beside me. Joanne and I had spen... Read full Story
Jon Paul 2022-01-18 5,061 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth
93%
Southern Hospitality Ch. 01
XtinaSmith2017 Ash gawped at his mother, incredulous as to what she had just said. He understood the basic premise of what had happened, but the reasoning she must have had absolutely baffled him. "Why?! Why would you do that?!" He pleaded, voice light and desperate. She shrugged, looking acr... Read full Story
Gwapo67 2022-05-16 6,968 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature
100%
Meeting Amanda Ch. 2 - The Next Day
After a hot evening together, the story continues https://www.ashemaletube.com/story/meeting-amanda-6595/ ------------------------------------------------------------------------------------------------------------- “I could really use a shower,” Amanda said while she... Read full Story
rforasht 2022-09-07 4,222 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
100%
Sweet Encore
I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... Read full Story
Regina10 2024-05-09 2,099 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
58%
Married guy wants a shemale to fuck his wife
I'm a married guy and I've had this fantasy of a shemale fucking my wife for quite some time! She is a very attractive lady. She has been hesitant in the past to try new, kinky things, however, lately, she has begun to get into what initially was my self-imposed chastity. However, she quickly shoots... Read full Story
shemale lover 2015-08-25 8,296 sucking Creampie pussy
85%
My Cock Dream
My name is Iris Cal. A few weeks ago, I had a dream. This is an account of that dream, with some holes and details filled in by my own fantasies. From what I remembered as I tried to write down as much of the dream as I could, I had woken up in the house in which I lived when I went to high schoo... Read full Story
shemale lover 2016-04-14 4,872 shemales Masturbation Fetish
86%
A Great night in by myself
I love dressing up in women's cloths they feel so smooth and sexy against my skin. A backless pinstripe lycra dress shows off my shoulders and back stretched tight over my peachy round buttocks. A little pair of white lace boxers underneath just visible as the skirt rides my thighs when I admire mys... Read full Story
shemale lover 2017-04-28 4,162 anal shemales Masturbation
100%
Angel & Victoria
Angel was a beautiful young girl living with two of her best friends, Monica and Amanda. All were transsexual, and the three shared everything together, from clothes, their sexy intimates, lovers, and each other's bodies. Angel was the youngest, at 23, a Japanese anime lover and the most... Read full Story
shemale lover 2011-09-23 5,691 anal Creampie Big Cock oral
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 8,892 Stockings sucking domination
100%
I am a Shemales' Bottom Slut Part 2
I have been with Nancy and I have moved in and quit my job and I run around her house naked 24/7 so she can take me whenever she wants and I love her cock. She has taken pics of me naked with her cum inside my ass and posted them on the web. Nancy said," We are going to have a party to... Read full Story
shemale lover 2011-10-04 3,862 Creampie cum oral
100%
The Terrace View Apartments Part 7
My new life had settled into a wonderful routine. I would wake very early in the morning, usually still wrapped securely in Mistress Kendra’s arms. I would spend an hour or so working on my figure maintenance exercises, enjoy a cleansing enema, a refreshing bath and body shave, then I would la... Read full Story
shemale lover 2011-11-19 3,868 Creampie Blowjob domination
50%
Man or Mandy? Part 3
We showered together, washing each other. We spent as much time kissing as watching. I was spending much of my time on her incredible tits, getting them all soaped up, and then rinsing them off. We got dressed, hopped on my Harley and roared off towards an auto parts store. As went into the mainl... Read full Story
shemale lover 2011-11-26 2,126 anal sucking Creampie ass licking
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 6,646 Creampie Big Cock ass fucking
91%
Lake Surprise
After finals of my first year in college in a northern university, I was ready for some real relaxation back home in the warm south. During finals I had started thinking how nice it would be to borrow my brothers boat and hit the lake for a week. I talked my roommate into making the trip home ... Read full Story
shemale lover 2011-12-08 10,578 anal Group Sex Creampie
88%
Audry: My Guide to a New World
For a long time, I've known I liked guys. Well, to be more accurate, I like cocks. Guys, I really don't find sexy. Women, I find sexy. A good set of breasts or a nice round ass with a little waist and big round hips will make me hard in an instant. When I look at a guy, I don't get turned on, but sh... Read full Story
shemale lover 2011-12-29 4,929 Creampie Shemale Fucks Guy huge breasts
100%
A Holiday Job Part 2
“Anne” was stunned by Nico’s offer. When Paul had discovered that his sister had left taking the wrong suitcase, the idea of becoming her for a week had been very appealing. The job in the bar, the innocent flirtation with Jorge the cute waiter over lunch had all been very enjoyabl... Read full Story
shemale lover 2012-03-10 2,380 anal sex Creampie fingering crossdressing
100%
A Job in the Theatre Chapter 12
Paula could feel her stomach as they pulled into the circular drive. She was nervous about seeing Sarah for the first time, almost more than seeing Ted. They got out of the car and were about halfway to the door when Sarah appeared. Paula smiled hesitantly. She could see Sarah's eyes go straight ... Read full Story
shemale lover 2012-03-14 2,128 Creampie cum oral sex
85%
Crossdresser At XXX Movie
It was hot and the sun felt like it was going to melt me. I was walking home from work. I never drive that much and I just got off the bus for a fast beer. I walked past this XXX Movie house and thought what the fuck, it has air and it is so hot. So in I go. I should say that I'm somewhat Bi. Tha... Read full Story
shemale lover 2012-03-30 3,951 anal sex Creampie handjob rimjob
100%
Crossdresser Caught in Act
I do not consider myself gay, nor do I think I am bisexual, but I do enjoy a nice big cock. I am not attracted to men at all and under normal circumstances find any and all homosexual activities quite disgusting, until I get really horny that is. When I get all hot and hard, I can't help but want a ... Read full Story
shemale lover 2012-03-31 5,559 Masturbation Sex Toys crossdressing vibrator
100%
A New Me...
Flash back 10 years when I had just turned 18 years old and had just been accepted into the University of Vermont. I was ecstatic because this was my reach school (I wasn't all that smart book wise) and it was the school that my sister Elizabeth (20, a junior) was already attending. My sister and... Read full Story
shemale lover 2012-04-14 5,183 Masturbation Fetish crossdressing
100%
Exotic Escapades Chapter 3
The smell of wood and coffee filled the quiet house as Tammy slowly picked herself up from a plush couch. Daggers of sunlight blinded her eyes as she eventually got on her two feet. Her body ached, and she noticed a small pink bandage on her left leg. The terror and pain of last night shook her as s... Read full Story
shemale lover 2012-05-05 2,956 tranny Creampie Big Cock Ladyboy fingering oral sex
100%
False Imprisonment
Having visited a morning magistrate's court in one in one of the UK's major cities some years ago, I was a little surprised at the way many cases especially of prostitution were pushed through at such high speed. Thinking back on my visit day the bones of this story emerged. I am sure what happened ... Read full Story
shemale lover 2012-05-24 3,847 Creampie oral sex transvestite
100%
Fantasies Fulfilled
I enjoy crossdressing and do so when ever I can. About the only time I dress as a man is to go to work. I have been doing this since I was eleven years old. I love to have sex with a man as if I was a woman and really think I should have been born a girl. I think like a girl and naturally act like a... Read full Story
shemale lover 2012-05-26 4,250 anal sex Creampie Blowjob crossdressing
100%
A Revenge Fuck Part 2
Frankie had been a great sport about the entire affair. She had taken me in, she'd showed me how to become and be the beautiful woman, Josie- she had completely made me who I was, even against her will. And then she was also there to shoulder support in my emotional crisis when things did not work o... Read full Story
shemale lover 2012-06-03 4,774 anal sex Creampie shemale oral sex
100%
Alex Two: The Next Time
Part Two of ??? (there is another series I'll start too, Hopefully its not too repetitive and my fetishes aren't showing too strongly. heh. That is sort of a prequel to this, I guess. I had forgotten about it till just now when I found it in a misnamed folder.) Alex Two: The Next Time.... Read full Story
AlexShouse 2012-07-12 3,150 tranny Crossdresser Masturbation
100%
A Turkish Delight
My export business was beginning to take off as I was now on my second over sea's trip. I was doing business with the Turkish government and I also saw it as an opportunity to explore more my fascination of cross-dressing. I would be visiting a country where I was not know and I would blend in with ... Read full Story
shemale lover 2012-07-15 2,941 Creampie oral facial domination crossdressing
100%
A Turkish Delight Part 2
As I sat in my hotel room I pondered my future and what may lie ahead. My passport had been seized and I was not able to leave Turkey nor could I tell anyone about my plight. It was late afternoon when a courier arrived at my hotel with a large white box. He rang the bell and upon answering I was gr... Read full Story
shemale lover 2012-07-16 2,653 anal Creampie Fetish domination crossdressing
100%
Abducted and Turned Out Chapter 2
2: Fun time So, after I blew the guy downstairs and told him to come and knock on my door and pay me to blow him again anytime, I went up and took a long hot shower and put on a nighty and went to sleep. I slept surprisingly well considering I had just spent a long night out selling my ass. I tho... Read full Story
shemale lover 2012-08-10 4,504 Crossdresser anal sex sucking Creampie facefucking
50%
Transsexual Sisters Chapter 5
Part 5: A friend is forced to say goodbye Cassie had made things right with Michelle and Nicole. She now had to square things with Randy. She found him in the hospital lounge. "Hi Randy, can we talk?" "About what? I think you made things pretty clear the other night." ... Read full Story
shemale lover 2012-09-08 2,749 Cumshot Masturbation threesome ass fuck
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 3,636 Stockings Crossdresser Cumshot Masturbation heels
100%
Sex with strangers in public bathroom
I always had a sexual fantasy of dressing up as a chunky sexy slut tranny and visiting a known public mens bathroom close to my house and giving oral sex and what ever they wanted me to do for them sexually.Well I finally got up the courage to do it and before I go into my true first time experience... Read full Story
shemale lover 2012-10-01 4,808 anal hardcore Creampie Fetish oral fingering
86%
Wife Catches Me With A She-Male
It all started out one day I was sitting around in my apartment watching adult porno on the VCR. My wife had just left for work. I was horny and my cock was hard so I started jacking off. I was lying on my back pumping my cock hard when I started to cum it had been a week or so since I had any pussy... Read full Story
shemale lover 2012-10-22 5,936 Cumshot Creampie shemale jerking
100%
Downsizing Chapter 3
Work was going quite well. The company started to grow again, and some new personnel had been hired. Even unknown to me, there had been a couple of males hired in the last few months. Ms. Stanton had informed them when she got to the dress code that the makeup was a requirement, and that the one mal... Read full Story
shemale lover 2012-11-10 2,976 anal sex Cumshot Creampie oral sex
75%
The dark elavator
I was working on a inportent computer tech. when this women send me a pc to pc message with a picture of a women say want to tast me baby. i look up and she says well how about it and winks i goto get lunch so i goto the elevator but it full. i dont want to take the red elevator its lights fliker... Read full Story
shemale lover 2012-11-18 2,872 anal sex sucking Creampie rimming
100%
Anastasia's Life
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember, not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barb... Read full Story
shemale lover 2012-11-26 7,108 Fetish cock sucking crossdressing
100%
Westward bound cum slut Chapter 2
Again I'm on the big bird headed out west for another fling. This time is going to be way different though, the players have increased, not to mention both sexes. The tale unwinds in the same fashion as the last trip out this way, the plane flight was long and boring, and being very nervous didn'... Read full Story
shemale lover 2012-12-16 3,514 anal Group Sex sucking Creampie cum domination
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 16,481 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
91%
The Dinner Party
The clock above the kitchen sink read 7:48 when I heard the metallic snap of Aya's key unlocking the front door. I opened the oven door and was rewarded with a blast of steam that smelled like a lazy August afternoon, all rich garden spices and earthy head. Inside was a boxy cookie sheet covered in ... Read full Story
shemale lover 2013-01-11 5,296 hardcore Cumshot sucking Creampie ass fucking
92%
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 39,475 Teen (18+) Bareback Creampie Lingerie ass fucking Interracial cd
48%
Guy gets gangbanged
We've all been lost in thought before some of us thin about fast cars or high power jobs. Not me though I think about hot women with big dicks, petite bodies, and Double Dcups. I can't help it I just love shemales that is until I was raped by three of them. They had 9inch cocks a piece and... Read full Story
Iced5 2013-08-14 11,970 sucking Creampie shemale gangbang ass fucking rimming
96%
My First Time as a Girl
I was hoping to hook up with a straight guy. I have 2 b*****rs and a s****r I’m the youngest and a Freshman in high school. Always been fem preferred to play with my s****r and her dolls. My dad is an ex-marine. Tough guy. My b*****rs are following in dad’s footsteps, military orientated. I‘m a b... Read full Story
shemale lover 2013-12-07 6,544 tranny Crossdresser Creampie ass fucking cd