Sort by
Relevancy

Free Stories

50%
An alumni gathering like no other
An alumni gathering like no other; Sea/Sand/Sun' and why not 'Sex' in a vancancy club; we got together to celebrate the 40th anniversary of our 1st meeting at university. The only rule was to come without a partner to relive our 'frosh' days. with friends of whom I had lost all trace, a... Read full Story
hippocampus_171 2024-06-13 871 anal Amateur Masturbation Blowjob Sex Toys Mature small cock big ass Ass to Mouth cum in mouth
83%
Janine awaits
My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... Read full Story
bunny cat 2019-02-04 3,740 Crossdresser Masturbation Blowjob Lingerie Mature cum in mouth
56%
Blow Job
My e-mail is: My rusted, green Toyota Tercel pulls into the mall parking lot. I pick a spot at the back, beyond where even employees park. The next car is a blue pickup 20 spots away. No one parks here, except at Christmas. But I know that I'll soon need the privacy. I'm a freak, a cross-dresser... Read full Story
shemale lover 2013-08-09 6,855 Crossdresser Masturbation Lingerie stripping party
100%
Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
darrell 2022-04-20 4,261 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
The Seductive Seed of a Tranny MILF
The Seductive Seed of a Tranny MILF SugarandSalt Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spo... Read full Story
Gwapo67 2022-05-03 7,694 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
92%
A Surprise Relationship
This is a fictional story, although it is based on people I did know. "Tony" and his twin sister "Kim" are based on a set of twins I knew, who were almost identical. I did have a relationship with "Kim" for almost two years, however, the relationship with "Tony&quo... Read full Story
shemale lover 2013-01-29 5,263 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 4,244 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,247 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,213 Crossdresser sucking Big Cock ass licking big boobs
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 4,816 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,437 Cumshot Masturbation oral sex
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 11,759 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
100%
The Fabulous Alessia Travestita
Alessia is a real transexual. Several of her porn videos are on this site. She collaborated with me in this story. Alessia is a natural blonde haired, brown eyed, mature fifty -five year old Transsexual woman from England. She is tall, very fit, stands 5'11," 36B-26-30 and a slender 133... Read full Story
darrell 2021-12-14 4,247 Crossdresser Blowjob blonde Big Cock domination Mature 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 6,985 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature
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 3,954 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
87%
Southern Hospitality Ch. 03
XtinaSmith2017 Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned ... Read full Story
Gwapo67 2022-05-16 4,713 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
92%
Southern Hospitality Ch. 04
XtinaSmith2017 Ash awoke feeling cold, he pursed his lips a little and shivered, curling up a little tighter, nude as he was, the action brought little relief from the cool air. He let out a soft murr of discomfort as his mind shook off the cobwebs of lingering dreams, he could see light throug... Read full Story
Gwapo67 2022-05-16 6,641 Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Mature cum in mouth
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 4,947 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
100%
Ladies who Lunch - At the Gloryhole
Ladies who Lunch - At the Gloryhole By Sabrina G. Langton *** Author's Note: Hi, just a quick little story to make us all wet and squishy. Three mature crosssdressers have a little more excitement than they are used to after lunch. I hope YOU like it... *** The Boynton Tavern So w... Read full Story
Brina Giselle 2024-01-06 5,158 Crossdresser Blowjob transgender mature crossdresser gloryholes
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 5,213 Stockings Big Tits Masturbation Big Cock Mature
100%
Edging lessons for Hannah
Hannah and I began spending our weekends together. She didn't have a job and I was always free those days so every Friday or Saturday night became sleep over night where we could be two 18 year old sissies, doing each others makeup, playing dress up and sharing our deepest desires. Now that our rela... Read full Story
KaceyKlarissa 2024-01-25 3,685 Crossdresser Amateur Cumshot Masturbation Fetish Big Cock kissing Homemade sissy romantic cum swap edging teen (18+)
100%
MILF Alessia Travestita finds a bottom boy pt 2
Several days ago, Alessia a beautiful Transsexual with a huge cock seduced Stan on their cruise ship. He willingly and enthusiastically sucked her cock and gave her his ass. She brutally throat fucked his mouth before pounding his ass. They spent over two hours together until they were interrupted b... Read full Story
darrell 2023-08-13 5,881 anal Shemale Fucks Guy Fetish Blowjob blonde Big Cock domination Mature deep throat cum in mouth sandals toe sucking
100%
Sabbatical or Continuous Gang Bang?
My twin sister Laura had already left to go back to college this fall season, but I had decided to take off a semester as I was totally burnt out on school and needed a break. We were twins but not identical though we did look a lot alike and roughly the same size me being a few inches taller. My... Read full Story
shemale lover 2012-08-28 5,495 Crossdresser Cumshot Fetish Blowjob gangbang
100%
Proud To Be A Sissy Chapter 1
I had just turned eighteen and only had two months of high school left. My marks were good and already had a possible placement in a university where I hoped to get a new start. I was so looking forward to getting away from all the shit that life had forced on me in this little hick town. Usuall... Read full Story
shemale lover 2012-12-23 11,829 Stockings Crossdresser Big Cock ass fucking ass licking
100%
How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
Chrissy Tunnell 2022-01-27 4,053 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
100%
I Missed Myself
As soon as Dr. Griffin returned to the examination room, I knew that the news wasn’t good. I could tell by the way he avoided my eyes as he studied his clipboard and fidgeted with his pen that something was wrong, terribly wrong with me. The ache in my groin that I had been ignori... Read full Story
shemale lover 2013-03-20 7,936 Crossdresser Lingerie pantyhose cd softcore
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 4,243 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
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 4,409 Crossdresser Blowjob Big Cock Mature cum in mouth
78%
Cara's First Time
Cara's First Time This little true story is about the first time I was with a man and a night that I will never forget. My name is Cara. Well that's my girly name, I'm a cross-dresser. I've loved dressing up in women's clothes since I was young when I used to dress up in... Read full Story
Emma W 2017-07-05 29,968 Crossdresser Amateur Bareback
100%
Groped on the Bus
In real life I do not crossdress in public, I am not yet comfortable being my true transgirl self, I wear normal men's clothes and I look like a guy. So I look very different from my persona here. So...there I was standing among dozens of strangers at a bus stop. I kept looking up from my phone ... Read full Story
Chrissy Tunnell 2023-03-17 4,964 Crossdresser Amateur Masturbation Ladyboy Guy Fucks Shemale Frottage
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 13,730 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
Camming down the rabbit hole Ch1
Back in January 2020 I guess I was lucky, I did have a regular job although the pay was miserable and I did have my own place. On my wage all I could afford was a miserable bedsit in a neglected part of town, but on the upside I didn’t have to flat share and it worked well enough for me. The west... Read full Story
Dani_does_Dallas 2021-08-11 5,321 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams
100%
Emily and Steve Part 8
I didn't even see it coming. I should have. I should have known that life just can't work out exactly like you would expect. Instead it has to throw you curve balls, put you back on your heels, and then put the next one on your chin. The first few months after Emily moved in, things were going gr... Read full Story
shemale lover 2012-04-07 3,057 Crossdresser Fetish blonde
100%
Josephine's First Day
My life at school was fairly uneventful. I wasn't brilliant academically. I wasn't a talented sportsman, actor or musician. I wasn't one of the popular children. I wasn't in physical fear from bullying, although there was a lot of teasing, name calling and 'jokes' that were funny for everyone else. ... Read full Story
shemale lover 2013-01-04 8,630 Teen (18+) Crossdresser sucking Uniform handjob
100%
Karen, My School Teacher Part 2
Just Staying a bit By FoxyHosed “Don't mention it. Now let me start on the pasta with meatballs!” She stood up from her chair “And besides, it will be nice to have someone to eat with, for a change!” She went to the kitchen to start dinner. “Make yourself feel at home!” I watched some TV ... Read full Story
FoxyHosed 2021-02-01 11,114 Crossdresser Fetish pantyhose Mature pantyhose cd
100%
Camming down the rabbit hole Ch2
How had I ended up in this situation? Sure I was going to need to make ends meet, but I could find a normal job couldn’t I? was I this desperate? Perhaps desperate wasn’t the right word, just over a month ago I had started out camming as a bit of fun, to maybe make a few pounds while I masturbated, ... Read full Story
Dani_does_Dallas 2021-08-11 3,550 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams
83%
the start of what to cum
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often mo... Read full Story
oliviabecket23 2023-07-04 6,658 Crossdresser Lingerie domination Sex Toys femboy forced webcams
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,200 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
100%
Revenge is Sweet
Henry Stewart was thirty five years old, married to a very attractive woman who'd given him three kids, he owned and ran his own very successful computing company in San Diego, "Stewart Computing", meanwhile he owned a large house in the wealthy small town of River Falls. All in all, Henry... Read full Story
shemale lover 2012-09-01 7,665 Crossdresser Cumshot Masturbation Lingerie heels
100%
Camming down the rabbit hole Ch3
Slowly stirring from my sleep, I stretched under the covers and a pleasant sensation spread across my torso, remembering what I was wearing when I went to bed I smiled at the caress of the fabric on my skin. It was a strangely comforting feeling, the pressure from the bra, panties and nightie felt l... Read full Story
Dani_does_Dallas 2021-08-18 5,128 Stockings Crossdresser solo Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade
100%
Camming Down the Rabbit Hole Ch. 10
As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous nig... Read full Story
Dani_does_Dallas 2022-04-12 3,402 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 4,135 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
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 30,262 Teen (18+)
50%
Trying It On For Size
I was twenty minutes early for my one o'clock appointment so I found a shady spot in the parking lot of the upscale chain motel, kept the engine running to power the air-conditioner on the warm Sunday afternoon, took a few deep breaths and tried to relax. My mind wondered back over the series of eve... Read full Story
shemale lover 2011-10-26 7,818 asshole licking sucking
50%
Al Fresco: An Erotic Sci Fi Tale
"Thank goodness for modern science," Ali said as she smoothed her tight black skirt across her shapely hips. The tall brunette turned this way and that in front of her mirror, admiring her taut, toned, and trim figure. Her hands moved up from her hips to cup the twin handfuls at her chest,... Read full Story
shemale lover 2012-09-19 7,101 Cumshot ass fucking oral sex cum swallowing
83%
Elaine & Me
- Chapter One – Our First Meeting - I had two weeks to go before the final degree exams and I was working hard. Perhaps too hard, because I desperately needed a break from the hours and hours of revision. It felt like I just couldn't take in any more detail about Quantum Mechanics or Solid ... Read full Story
shemale lover 2012-03-31 11,311 sucking Fetish transsexual
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 7,122 Fetish cock sucking crossdressing
100%
Anastasia's Life So Far
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, Barbi... Read full Story
shemale lover 2012-11-27 10,925 Fetish crossdressing feminization
91%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 19,271 Big Tits sucking ass licking fucking
100%
Eve Quest
Chapter 1 My name is, or maybe we better make that was, Andy Moore. Until recently my personal identification was in the name of Jamie Jo Moore and everyone I knew called me Sissy. My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,... Read full Story
shemale lover 2012-04-21 6,292 domination oral sex transvestite
80%
Debbie Part 7
As Debbie was led into Dr. Jacobsen's office, she saw that Mistress was already there waiting for her. "Your property Miss Chamberlain", the doctor proclaimed, indicating Debbie. Debbie's heart began to flutter with love and submissive fantasies as she saw Mistress. Mistress was dressed in... Read full Story
shemale lover 2011-12-23 9,493 transgender toys bondage and discipline heavy
83%
Teacher Student Confidentiality
It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... Read full Story
shemale lover 2012-02-11 13,909 anal Blowjob black fiction
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 7,100 fuck oral
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 14,022 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
30%
CD Delight
The following is an account of a true encounter between consenting adults. The names and places have been altered to protect the individuals. Any resemblance to actual persons is purely coincidental. It is not intended for minors. If you are offended by sexually explicit material or have receive... Read full Story
shemale lover 2012-01-27 3,228 sucking cum Sex Toys cd
100%
1st Transsexual Affair
Paul's cock was hard as a rock and with a penchant for sleeping in the nude, its fat length pressed against luxurious satin sheets. The dream of searching for a urinal or bathroom now became reality. He stretched, groaned and yawned his way off the comfortable bed and padded across the room. The mar... Read full Story
shemale lover 2012-02-04 4,180 cum fuck oral