Sort by
Relevancy

Free Stories

91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,622 Big Tits Cumshot Masturbation Uniform Frottage
50%
Spy Girl
Vicki stood in the dark doorway as she watched her mark, Ivan Patrinkov, approach up the empty street. There was no way he would be able to see her where she stood in the shadows. She wore a skin tight leather jumpsuit with black low-heel boots. She would have preferred to have on a pair of stiletto... Read full Story
shemale lover 2011-11-09 4,846 anal sex shemale Frottage
100%
Transgender Encounter
I was at the Mall in Torrance, CA looking for a new pair of pants. There was this lovely young woman named Sherry working there, who was very solicitous, helping me find my size and select a pair of pants that weren't too out of style. I hate to shop, you see, so I usually wear a pair of jeans or sh... Read full Story
shemale lover 2011-09-19 3,881 suck cum swallowing nipples
94%
She was a he
I was recently divorced, 39 years of age and living in an apartment in Sydney's inner eastern suburbs not far from the famous red light district of Kings Cross. After two failed marriages, I was footloose and fiance free and as lusty as a rampant bull on speed. I chased after anything wearin... Read full Story
shemale lover 2012-01-24 7,065 Cumshot Guy Fucks Shemale Frottage
93%
Chance Encounter Part 1
My first encounter with a trans woman wasn’t all that great to be honest but I still felt it was something worth exploring at the very least as I am open minded. My second encounter was trully something special. Through word of mouth I was asked to stop by at a house not too far from where I was ... Read full Story
Katlick 2019-10-07 8,246 Small Tits Frottage Homemade
92%
Lola - chapter one
This is a fantasy but with a lot of inspiration from real life experience. More chapters to follow. Chapter 1 So now I knew, without a shadow of a doubt, what it was that caused this familiar smell in my house - and where it came from. When I got back home my laptop was lying open on the kitc... Read full Story
BellaBeau 2023-10-05 6,246 anal Amateur Cumshot Masturbation Bareback Blowjob Guy Fucks Shemale Frottage Homemade
100%
Wife got suspicious...
Wife got suspicious... I ended up having a relationship with a married man I'll call Tom. I didn't know he was married until he told me we had to stop kind of like dating because his wife was getting suspicious. We met online, he was a guy who liked crossdressers like me. He was pretty cute... Read full Story
Kellygirl81 2024-06-18 2,694 Stockings Crossdresser Cumshot Lingerie Frottage cum in mounth
100%
MY First Time with a non-binary/cross-dresser
After I had graduated high school but before I had left for college: I was hanging out with a friend and a friend of theirs at their friend’s house. For the story let’s call my friend Dan and his friend Charles. We were watching some movie on Charle’s (parent’s) big TV. Charles gets up eventually an... Read full Story
ghostpeople 2019-03-12 7,268 first time Crossdresser Amateur Group Sex Cumshot Bareback threesome Frottage Homemade sissy blow job condomless
100%
Masturbation fantasies 2: Looking for Amanda
Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... Read full Story
ThatEroticWriter 2019-07-24 9,024 Big Tits Cumshot Masturbation threesome Frottage
100%
Horny Writing A Strange Habit
I enjoy watching videos which I can Vicariously live. This is nothing more than my horny hobby, an amalgamation of various thoughts. My form of hands free edging. Spell checked only, "No I haven't proof read a first draft, not trying to publish masterful works here." Hope to hear from those w... Read full Story
Araina 2021-03-08 2,863 Crossdresser Amateur Big Tits Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Frottage Homemade Ass to Mouth cum in mouth
100%
Meeting Amanda
I’m a happily married man. My wife Tess and I have been together since we were teenagers. We were each other’s first real lovers and being in our mid-thirties by now, we still madly in love with each other. Tess and I always are very honest and open to each other. Both in normal life and sexual... Read full Story
rforasht 2022-07-20 7,660 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
100%
I fucked my personal trainers ass for the first time
I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... Read full Story
Madison Heights 2023-05-18 7,196 anal Shemale Fucks Guy Big Cock Frottage
100%
Two CD's the first time we meet.....
We are meeting for the first time since talking online. I want to dress for you gurl, I want to feel as you do, I want to be your slut, your slave of desire. My panties are a sheer white, my hard cock can be seen ever so pressing against them, I rub myself for you as you watch, drooling now. Hand... Read full Story
kelliecdgirl 2024-04-10 4,146 Stockings Crossdresser Cumshot Masturbation Fetish blonde Big Cock Lingerie pantyhose Frottage sissy femboy shemale + shemale
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 4,204 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
Dominated sissy goodgurl34
Mmmm ty Sir Deitrich --I'm standing in your open doorway wearing black latex stockings and garter and some hott red lace panties over top -I have a black corset on and a very sheer dress on ,wig and gurl mask ---my wrists are cuffed to a circle hook one on each side of the doorway door jam about 6... Read full Story
goodgurl34 2022-03-15 2,504 Crossdresser threesome redhead domination Guy Fucks Shemale Sex Toys Homemade shemale + shemale
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 7,802 Shemale Fucks Guy redhead Guy Fucks Shemale cum in mouth
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 4,440 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
88%
Oh My, You Have a Cock...
It was a regular Friday night no different from others I'd experienced before. I was lonely having broken up with my girlfriend earlier that week. What a bitch! I needed to find me a sweet woman capable of matching my libido. My last lady was all about the lights off, missionary position sex, come t... Read full Story
shemale lover 2013-08-09 32,979 anal sex Cumshot Shemale Fucks Guy redhead
100%
Regina’s Double threat.
Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... Read full Story
Regina10 2022-02-08 3,215 Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock redhead Guy Fucks Shemale Ass to Mouth double anal
100%
Birthday Present
Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all about the exchange and nothing else was said about my birthday. The day arrive... Read full Story
shemale lover 2012-06-16 14,295 Cumshot Fetish orgasm oral sex
71%
Birthday Present Part 1
Birthday Present or (I've Looked at Love from Both Sides Now) Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all abo... Read full Story
shemale lover 2013-01-18 11,491 hardcore sucking Blowjob Lingerie ass fucking
50%
Giving Away Virginia Holton
Today would have to wait, thought Marla Holton as she hurriedly gathered her bag and notebook in preparation for a no-holds-barred departure from her office at Prism Design. As general manager she had the privilege of arriving and leaving at will, though no one could ever fault her for not putting i... Read full Story
shemale lover 2011-10-08 4,699 shemale cum ass fucking
50%
For The Sensual
For the sensual, description is everything. The collar. The collar is custom-made; one of two; her request. This particular one matches the corset. The corset—the "bustier." The collar. Literally, no choker here. She is disciplined. Her collars merely evoke ownership. She belongs. Sh... Read full Story
shemale lover 2012-11-14 3,347 anal kissing facefucking
100%
the orgiastic fever of a trans-milf
Simulating a woman, or the orgiastic fever of a trans-milf It's been two months since I moved to the megapolis, where I've discovered several places where the third gender goes. One of my first explorations was a huge lingerie shop in a MALL; I wanted to buy some sexy stuff without being noticed ... Read full Story
hippocampus_171 2024-09-04 1,128 anal Amateur Cumshot Creampie Shemale Fucks Guy Latex Sex Toys Mature small cock
50%
Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
shemale lover 2012-02-08 7,283 fuck oral
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 14,117 first time sucking fuck domination
100%
The Invitation
"You see, we have to come up with something that would be so embarrassing for you that there is no way that you would ever show those pictures of me to anyone, regardless of how d***k you got, or how horny you got or how pissed off at me you were,” Sally went on. “Something that wou... Read full Story
shemale lover 2012-03-20 6,276 Group Sex crossdressing feminization
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 5,223 anal sex asshole Big Cock
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 6,871 Creampie Big Cock ass fucking
100%
Best trip to the mountains
I was driving out to the hills for some solo camping. I was alone since all of my friends had quit on me at the last minute, but i figured i'd just enjoy nature while i had the chance. I was almost through with the four hour drive, and noticed fewer and fewer cars as i got closer to the site. Onc... Read full Story
shemale lover 2012-03-04 3,996 anal shemales Group Sex oral
90%
My Pet
I went into the pet store very excited. I was really going to do this! I walked up to the girl behind the counter. She was pretty and looked very young to be working in a place like this. Hi. I'm interested in the pets in the back. Oh? What kind of pet were you looking for? The kind that... Read full Story
shemale lover 2012-05-02 5,417 big dick Cumshot Blowjob fingering jerking off
50%
A Perfect Life
The reasons I am not writing this myself. I have finally convinced someone to do it for me. She promised to post it on the Internet, but only as fiction. I suppose it is a bit unbelievable. It all started with the best of intentions. I had married my love while we were still in college. She... Read full Story
shemale lover 2012-05-05 12,762 transgender
60%
The Creators: Book One by
Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... Read full Story
sagga 2018-09-18 30,528 Teen (18+)
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,392 Fetish transformation dildo
66%
Dirty Business Trip
Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and he... Read full Story
shemale lover 2012-09-26 12,979 Group Sex Cumshot shemale oral
66%
Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
ASSEaster5678 2019-01-25 12,349 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
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 7,875 anal Fetish cum crossdressing
93%
A discovery
The booze and caffiene had turned from a warm buzz into a slightly annoying headache in Miles' psyche. He watched as his live-in girlfriend Mary danced and ground against a tall blonde that could have been her younger sister. Club Inferno was at the point of orgasmic rush when the standing room o... Read full Story
shemale lover 2014-08-15 5,378 licking shemale pounding
80%
Buffy the Shemale Vampire Slayer Part 13
Buffy's cock slipped out of Baubo's mouth, and she licked the smooth skin of the stiff, elongated shaft with her tongue. Baubo had no hands, but, even so, she was a superb cock sucker. More than once, she brought the Slayer to the brink of orgasm, then backed off, letting Buffy's sexual passion abat... Read full Story
shemale lover 2011-08-23 3,876 Masturbation pussy shemale
0%
Looking-Glass Ladyboy
I was taking a walk to stay--all right; I'll admit it--to get in shape, when I saw the "Going Out of Business" sign in the second-hand furniture store a block north of my condo. I wasn't in the market for anything, new or used, but I can't resist a bargain, and what was better for finding ... Read full Story
shemale lover 2011-10-29 7,802 asshole Fetish Ladyboy
100%
A Discovery
But you see, even in his druken stupor, Miles was leaning against the south wall of the dance floor hoping.dreaming that Mary would coax the woman she danced with to come back to their apartment for a while. Club Inferno was the premiere goth/fetish club in Hollywood, and it was not uncommon for adv... Read full Story
shemale lover 2012-01-22 3,732 hardcore fucking transgender
100%
A Discovery
The booze and caffiene had turned from a warm buzz into a slightly annoying headache in Miles' psyche. He watched as his live-in girlfriend Mary danced and ground against a tall blonde that could have been her younger sister. Club Inferno was at the point of orgasmic rush when the standing room only... Read full Story
shemale lover 2012-04-29 4,341 Cumshot shemale Big Cock oral sex
85%
Unforgettable First Time
I am in my late thirties and have known for a while that I have a sexy body. I'm 5'11", slim and athletic with little cherry butt and shapely legs. A lot of women have told me my body is sexy. A few men have mentioned it too. Sometimes I get photo-snapped at the pool or the beach. I've been luc... Read full Story
shemale lover 2016-05-06 10,298 cum oral deepthroating
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 10,933 Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale Mature
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 31,193 strapon porn
66%
Would You
'Would you...?' 'Look the part to play the part....' 1 5' 4...dreaded, and to be dreaded....bookish, be-spectacled—damn near owlish....so much so that you might miss the way her tits spoke to you no matter how much she attempted to 'silence' them ....that you might miss the way her sk... Read full Story
shemale lover 2012-09-23 6,727 sucking cum massage
93%
The Babysitter's Secret Part 2
Two months had passed since Jenny and I had first made love on that fateful, snowy night. At least once a week, occasionally many more, Jenny and I had found time to be alone and indulge in our secret affair. I had never believed any sexual experience could be greater than our first time together bu... Read full Story
shemale lover 2011-10-24 6,845 Stockings shemale oral sex bisexual
50%
The Wizard's Semen
The forest was dense, thick branches hid the way ahead forcing the four women to push through gaps that weren't really there as the foliage scraped and scratched them, making life very uncomfortable. "This can't be the way, there's something wrong" said Minerva from behind the leader, Cara... Read full Story
shemale lover 2011-11-16 3,907 orgasm facial deep throat fucking
80%
A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... Read full Story
shemale lover 2011-12-06 11,677 Bareback cum ass fucking slave
100%
janine 2
After my epiphany, after my fainting, after my two near consecutive, mind melting orgasms, I was ready to meet the world with new resolve. No longer would I keep my true self under wrap. I was ready to become Janine, however I was going to have to be cautious, for the time being anyway. The first th... Read full Story
bunny cat 2019-02-08 3,830 solo Masturbation Sex Toys Mature
100%
Charisma Part 1
Tiffany De Vine wondered whether the ladies’ dressing room in which she was about to try on a brassiere was under surveillance by some fat, obese fucker with a day’s stubble of beard and a cum-stained crotch. Probably, she thought; it would be just her luck. Well, if some slob was drooli... Read full Story
shemale lover 2011-09-03 3,725 Big Tits shemale Lingerie
100%
Beefy Buns
It's hard to get good help. Probably, that's true in any business, but it's especially difficult to find decent employees in the fast food racket. Believe me; I've tried. I manage the local Beefy Buns franchise--burgers, fries, and shakes is our mainstay, but the menu also features fish and chick... Read full Story
shemale lover 2012-04-22 6,265 anal sex Creampie blonde shemale
100%
Amphotericity
It's hard now to look back on who I used to be and accept that we're the same person. I know a lot of people could say that but whereas they have most likely changed gradually with age the alterations to my life happened suddenly, unexpectedly and all due to a strange twist of fate in an otherwise u... Read full Story
shemale lover 2012-10-29 2,956 sucking kissing
100%
Jo, Shemale Goddess! Part 1
Jo plumped the cushion and carefully positioned it until it was precisely at the right angle. Nothing less than perfection would do. Ricki, her friend of twelve years was coming to stay overnight and she would notice if the tiniest thing was out of place. An impatient knock on the door signalled ... Read full Story
shemale lover 2011-09-04 5,613 anal sex sucking shemale
88%
Amsterdam
zNote: This story evolves around a "shemale" so there is some bi-sexuality in the telling of this tale. If that's not your cup of tea, then please, don't bother reading it. Thank you. Amsterdam My wife and I had flown over from the states to visit with her parents who lived there. I ... Read full Story
shemale lover 2011-10-17 8,947 Group Sex licking sucking stroking
66%
Tgirl
The year is 2044. My name is Robert. I am 26. Light brown hair. Dark brown eyes. 5' 9", 122 pounds. I work for a supercomputer research and development firm. Like many young men at the leading edge of technology, I am transgendered. My counselor is Dr. Elizabeth Paris. Under her con... Read full Story
shemale lover 2011-11-26 7,426 shemale transformation domination