Sort by
Relevancy

Free Stories

100%
My Gangbang
It was junior year of highschool. There was this one girl who I liked but was too afraid to do anything about it. Her name was Jessica. I thought she was too "cool" for me. She always hung out in a group of 3 other girls. She was short, about 5'2, her body was alittle plump, not too fat, b... Read full Story
shemale lover 2012-05-09 4,636 anal Group Sex Cumshot oral
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 7,165 Cumshot ass fucking oral sex cum swallowing
100%
Leila My Hermaphrodite Lover
I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most. It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before. I'd stayed over at a friend's house and after a ni... Read full Story
shemale lover 2012-12-17 4,228 taboo Cumshot shemale Mature
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 15,248 first time ass Cumshot suck cd sissy make up
100%
The Dark Backwards Continues
I jerked off several times while watching the SULKA video. At this point I wanted more. I returned the videocassette to the video store and made my way towards the darkness that was the ADULT section. I opened the door and there were several people in the room. My excitement turned to fear. Fear of ... Read full Story
Bryanferryfan 2015-11-16 4,006 suck oral sex dick transsexuals erotica
94%
Lonely in L.A.
I don't do this. I simply don't. But I was emboldened by theloneliness of being in a strange city without any friends around. I was taking my first trip to Los Angeles for an appearance on a game show. I'd be getting up bright and early the next morning and was spending the evening alone in a hotel... Read full Story
bigtranslover 2014-02-13 7,264 anal transsexual
100%
Shemale On Webcam Made Me Cum
It wasn't enough for me - regular porn, regular girls... I felt like I was losing it, not having the only thing I really desired: a shemale. But I was new in that world, not knowing where to go, where to look, so I decided it was better to see shemale on webcam first. I searched the internet and ... Read full Story
shemale lover 2015-12-31 3,964 Big Tits Cumshot shemale
100%
Fantasy Cum to Life
Ryan and Alyssa were in the midst of wild make – out session on his living room couch. She was leaning over him, one hand on his chest, the other behind his head; both of his hands we placed firmly on her ass. Ryan actually had the conscious thought that he had probably not kissed anyone this ... Read full Story
shemale lover 2012-05-30 4,057 Cumshot shemale oral sex handjob porn
84%
Emily's welcome
Since embracing the feminine me I’ve been on a bit of a shopping spree, it’s tough to be a gurl who hasn’t had anything really nice to wear for so long. In particular I love to buy pretty panties which keep my clitty nicely in place, but also rub up against my pussy as I walk – with nobody any the ... Read full Story
EmilyTG 2019-07-04 5,709 Crossdresser Group Sex Cumshot threesome Blowjob
94%
My first time crossdressing with a man
It was Christmas night 2016 and I had gone out to the bar with a few friends. Came home a little tipsy and very horny! I rushed to my room, took off all my clothes and put on a very sexy, slutty outfit (black lace thong with matching bra, a blue sweater, black mini-skirt, and black knee high boots) ... Read full Story
Betty D 2021-01-18 8,467 first time Crossdresser Amateur Cumshot Fetish Blowjob Mature Homemade mini skirt small cocks black panties obese
91%
Southern Hospitality Ch. 02
XtinaSmith2017 Laura felt herself lifted lazily from the arms of sleep, her body relaxed and floating on a small cloud of pleasure, her mind filled with images, sensations, not pulled from whatever dream she had just been having but instead, memories, memories from the night before. Memories of... Read full Story
Gwapo67 2022-05-16 4,643 Bareback Creampie Shemale Fucks Guy 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 4,313 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
100%
My Noisy Upstairs Neighbors Part 3: Making Porn
In Part 2, I recounted how Paul, my commanding upstairs neighbor, coerced me into making porn with him and his younger roommate. Now, I'm excited to share the first video we created together. At 12:45 PM on Saturday, I nervously approached Paul's door. After knocking, Paul opened it with a smile ... Read full Story
Chrissy Tunnell 2024-07-16 928 Crossdresser Amateur Group Sex Bareback Fetish Blowjob Ladyboy gangbang Lingerie domination Guy Fucks Shemale sissy femboy
95%
First TS sex
I think I was near my 35Th birthday and, believe it or not I had never had experience with a transsexual. I had plenty adventures with men and liked it very much as well as with women. Decidedly I was completely bi. As I wrote in previous stories, I’m writing about near 30 years ago. It was... Read full Story
shemale lover 2014-08-11 5,931 shemales gay male wanking
94%
Foursome with two ladyboys
It's been quite some time since I posted a new shemale story here. Hope all of You who have experience with shemales will finally have some courage to write about it and share it with us. Let this sizzling story by Tommy be an inspiration to You. Who wouldn't want to be in his place in this crazy fo... Read full Story
shemale lover 2015-03-15 6,722 Group Sex Blowjob cumshots
88%
Got more than he bargained for
This story was written for Trans Ladyboy by Brandi, a hot dominatrix and a phone sex operator. She says guys often call her to share their tranny fantasies with her, one of which would be getting dominated by a tranny, and, you know, she's really good at that! Call her for this phone fantasy (1.99 a... Read full Story
shemale lover 2015-06-07 6,438 Group Sex Blowjob domination
66%
A Girl's Best Friend
The party was in full swing when Ryanna and her friends arrived. Of course, they were an hour late, since Glenys had gotten lost on the way. The house was out in the back woods; the owners didn't exactly go out of their way to make it easy to find. Their fellow townspeople probably would have frowne... Read full Story
shemale lover 2012-03-06 5,487 Crossdresser Shemale and Girl oral sex condom sex
100%
Buying Time
It’s a hundred dollars to use the sex machine in the public restroom. Insert a couple of fifty-dollar coins into the payment slot to remain anonymous, though of course it’s more convenient to just let the data terminal do a neural scan and auto-debit your account. A hundred bucks buys... Read full Story
shemale lover 2012-03-25 3,817 anal sex Cumshot shemale
92%
Denise - New Beginning
Life was good. A couple of years out of school, I was working as a business software developer in the mini-silicon valley near the university. I was sharing a flat with a couple of undergrads. Unfortunately, both of my "roomies" were about to graduate. One was an ROTC type and would be goi... Read full Story
shemale lover 2012-08-18 4,391 cum fingering oral sex cum swallowing
100%
Deer Hunting with Daddy
Every year, a group of my family members, mostly uncles and male cousins, all pack up our gear and head into the mountains every fall for the yearly deer hunt. I had been going since I was 5. All the younger cousins slept inside an uncle's trailer, while the adult's and older cousins slept outside i... Read full Story
shemale lover 2012-08-20 5,133 cum fingering oral sex rimjob
100%
Lady In The House Ch. 06
A story by MicheleNylons (Michele continues to be used by prison inmates.) From Part V Harry leant over me and kissed me full on the lips. "That was worth every penny; you are one hot nurse," he laughed. Harry grabbed a handful of my clean white skirt and wiped his cock on it. The silver... Read full Story
✘Transensual✘ 2019-02-25 3,754 Crossdresser domination prisoner prison sex Prison Bitch
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 11,869 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
66%
More from my closet....
......being single is so better to play my games, no wives to take up my day, no one to lie to anymore about where I went... I had a layover for 3days in Vancouver last fall, three days all to myself, with the aid of google maps I found the local steambath for men. Steamworks it was called, set... Read full Story
badbadboi667 2020-12-03 3,278 Amateur Group Sex Outdoor Bareback Fetish gangbang domination Ass to Mouth amature
100%
Sissy Training
This is a true story, looking back it is hard to believe it actually happened, but it did. I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We&r... Read full Story
shemale lover 2012-03-12 8,160 Group Sex Fetish bdsm
100%
Dogging tv slut
It was dark enough now I thought. It was about eight o'clock on a warm spring evening and I was ready. I had started getting ready about three hours earlier. I'd showered, cleaned all those special parts, applied my make-up heavily and dressed. I was wearing a skimpy flower print top over a black si... Read full Story
shemale lover 2012-05-22 6,236 anal sex Cumshot oral sex
100%
Double penetration in Vegas
On a trip to Los Vegas for my Birthday we had a great time. Same old shit, we won and lost, saw all the sites and a few shows. The last night we were there however we were BORED…. That being said and knowing US, We took a stroll around the hotel. Maxx was checking out all the hot women in the... Read full Story
shemale lover 2012-05-31 4,834 anal sex Blowjob transsexual orgasm
100%
A Special Girl
Please allow me to introduce myself. My name is Steven Brun. I'm a young Black guy living in the city of Boston. I recently graduated from high school and started college. I go to Boston College. It's a school full of rich white kids but I'm liking it so far. The city is big, much bigger than the sm... Read full Story
shemale lover 2012-06-30 5,451 Cumshot Blowjob oral sex
100%
Adventures Of A Kinky Tgirl Whore
It was a cold winter's morning when Jessica and Phil awoke to the soft twitter of the birds outside and the early morning sunlight shining through the window of their large detached home on the outskirts of London. Although close to the town it was still a rural location and a place in which they... Read full Story
shemale lover 2012-08-17 3,340 Cumshot oral sex
100%
Angel Chapter 7
Angel Jones's Christmas sex affair with Dennis McGowan had been extremely enjoyable, but strictly a one-time thing. Although tempted to stay in London, in hopes of enjoying more of the lovely T-girl's charms, he had previously taken on commitments that had to be met, and he left London in order to m... Read full Story
shemale lover 2012-12-01 3,924 anal sex Cumshot tgirl
93%
Proud To Be A Sissy Chapter 7
"You're being really dirty little sissy slut today," daddy chuckled and asked, "What's gotten into you?" "Making up for the last few days I guess," I giggled hugging him tightly, "and I missed you too." "I missed my little sissy too." He repl... Read full Story
shemale lover 2012-12-24 7,608 Crossdresser Cumshot Blowjob Big Cock ass fucking
75%
Kidnapped (Adult Fiction)
Kidnapped I remember being normal. I was a young man in my 20's living in my parent's house struggling to get by. I was online more than I probably should have, but it was an escape from the harsh reality of my life. I didn't feel fulfilled or like a success, I felt like a failure on many differe... Read full Story
Vennom 2019-06-17 24,628 Fetish transformation fiction pov mind control drug interaction mind mindfuck change
83%
Milking Time Jordan's Arrival
These stories involves a group of shemales who live on an island that exists in our world, but they chose to remain mostly isolated. That's part of the reason I also call them amazons. The shemales in my stories have genitalia that start at John Holmes' size, and then get much bigger. (This is a... Read full Story
gman57 2019-09-25 10,613 Big Tits Big Cock shemale + shemale
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 3,641 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
Surprise Ending (Part Three)
I rolled my dick around her hole to spread the precum off it and lubricate it. The feeling was sensational and I couldn't spend much time easing my way in --I shoved right in the the hilt in one steady push. Karla practically jumped off the couch and screamed. I thought maybe I had hurt her (I am... Read full Story
Chantel13 2022-08-23 4,335 Crossdresser Amateur Group Sex Cumshot Outdoor Creampie Shemale Fucks Guy Big Cock Shemale and Girl redhead Guy Fucks Shemale Ass to Mouth
50%
Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... Read full Story
Elainetguk 2023-09-06 4,832 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
100%
My first made me a femboy (2/3)
I'm sure it was something that was going to turn me on before it started but the first man I was ever with had his own desires for me. I had no idea all the places it would go but I loved all of it. My best friend moved into an apartment building in a quieter side of the city we grew up in. She h... Read full Story
boytoypdx16 2024-07-03 1,426 femboy teen (18+)
74%
Sexy Young Shemale
When I was twelve my next door neighbors Sam and Ted trained me in the art of cocksucking and creamy yummy delicious cum eating for hours everyday during my summer vacation and I fucking loved it! I was small framed and wore my long blonde hair in a pony tail and always wore my smallest shorts so I ... Read full Story
shemale lover 2018-09-28 10,584 sucking Big Cock cum swallowing
50%
Sex with Shonda
I'm a workaholic by nature. I love my job but that's not why I work so much. I work long hours simply because when I get home I don't quite have anything productive to do. I just sit down in front of the television or I chat over the internet. Life at home is dull so the best solution seems to be en... Read full Story
shemale lover 2011-09-18 4,058 Blowjob fingering handjob
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 3,901 anal shemales Group Sex oral
91%
Becoming a Wife
Lucy had travelled a long way in the past few years. From bedroom cross dresser, to out and about T girl. From T haunt socialite, to flirt ,to promiscuous thrill seeker. But it had never been enough. Chance bar room meets, one night stands, and hit and miss internet dates. Like many T girls she had ... Read full Story
shemale lover 2012-03-06 6,520 hardcore anal sex tgirl
100%
European Vacation
I was 18 when I first went to Europe. That month would change my life. My parents had died when I was five, and I was raised by family friends; they also controlled my trust fund. It's not a coincidence that I went to Europe just as I came into control of the money. I loved my foster-parents, but... Read full Story
shemale lover 2012-04-21 3,829 anal sex cum oral sex sissy
76%
Mistress
My wife (Airlia) and I are open minded when it comes to sex. We are pretty much into everything, but at the moment we found ourselves going to a mistress for a bit of fun. We have been to our mistress four or five times so far and we both enjoy watching the other getting abused, especially Airlia wh... Read full Story
shemale lover 2012-04-22 4,445 anal Group Sex oral fingering domination Sex Toys
50%
The club
"Okay ladies," Missy said to her guests, "relax and get ready because I have a very special treat for today's meeting!" "What is it?" and excited Jayne asked while removing her sweat shirt and jeans. "Now you know better than to than that" Missy replied with a... Read full Story
shemale lover 2012-05-03 4,582 Group Sex Cumshot Ladyboy fingering Sex Toys
100%
Jesse’s First Day
Jesse didn’t want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse ... Read full Story
shemale lover 2012-05-16 5,439 hardcore anal sex Cumshot
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 4,318 Fetish Interracial Sex Toys
100%
Bike Shed Rendezvous
Chapter 1 A meeting you can't refuse The sun is shining brightly, but the ground is still damp from the morning's rain and the air is very cold. It's lunch time and you quickly walk across the College car park to the sports pavilion. Becky your sweet heart has told you to meet her and she's been ... Read full Story
shemale lover 2012-06-11 3,204 Fetish oral sex crossdressing sissy
100%
My shemale GF Part 4
I am now pretty much living at Christys place along with Ashley. So Ive reverted back to my 13 year old self of having wet dreams, and its really annoying especially waking up with a puddle in the bed. Chrisy went shopping, while i was just chilling and smoking weed with Ashley. Christy walks in and... Read full Story
shemale lover 2012-07-19 2,685 shemale cum oral sex handjob
100%
A Wife Comes Around
Let me start by explaining that I was the prude wife. I wasn't very experienced in the sex department, and also very naive, when we were married, although neither was he. We had sex but mostly missionary position or me on top, nothing adventurous like doggy style, which in my naivete then I thought ... Read full Story
shemale lover 2012-07-25 4,074 fingering oral sex Sex Toys
46%
My first time and loved it
My name is jay i have been attracted to shemales for a very long time i have always fantasizec of being with one but never happened.i dont know where to go to meet them and im real shy and quiet at first it sort of sucks trying to take to a beautiful woman never know what to say.so i decided to join... Read full Story
Hbjay 2012-08-14 4,028 first time anal sex shemale
80%
Office Policy
“Ok ladies and gentleman, please put your hands together for the beautiful and talented Erika!” the DJ’s voice rang out over the thumping alternative beat as the object of my lust strutted to the stage. Erika’s saucy red curls bounced on her head and on her soft porcelain whi... Read full Story
shemale lover 2012-08-30 8,474 anal ass sucking threesome tits fingering sex blondie
100%
Dress Up For The Girls Next Door
I’m just your ordinary guy, you know the type, women love me, I’m an electrician by trade and there isn’t a single or married woman out there who hasn’t asked me, “Can you really install my ceiling fan for me.” 6’, 200 lbs, brown hair, blue eyes, I keep acti... Read full Story
shemale lover 2012-11-18 3,877 Fetish jerking oral domination Sex Toys swallowing tit licking
100%
Jesse's Dream Job - The First Day
Jesse didn't want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse had ne... Read full Story
shemale lover 2012-12-20 9,595 hardcore Cumshot Shemale Fucks Guy ass fucking handjob
90%
Hermophroditie
Ι am a pure blood. I know many of you have seen Hermophrodites on television, some may actually know one, but I am different. It all started centuries ago in ancient Greece when the gods ruled… My grandmother was a beautiful woman. She was petite with a nice curvaceous body, the desir... Read full Story
shemale lover 2013-07-16 3,937 tranny shemale sex bisexual party
81%
Bimbo Barbiex
Ooh hiya boys, I'm Barbie Leigh, a naughty little bimbo tranny, 19 yr old, 5'7" tall, blond, blue eyes, slim and tanned with a hot curvy ass. I have been dressing as Barbie since I was probs about 16 and I'm very well versed when it comes to horny guys and how to please them.lolz... Read full Story
Barbie Leigh 2013-12-08 4,352 tranny ass Teen (18+) sucking rimming
66%
My TS Mistress
It is night time and I am lying on my side in the bed. I am naked wearing just 3 silicon cock rings. I try not to touch myself. Earlier Mistress had told me to go up to our bed and wait for her. I did as she said. I could hear her with her submissive for the night. A married man...well, another mar... Read full Story
shemale lover 2014-09-07 5,714 tranny hardcore Lingerie ass fucking domination
50%
Angel The Shemale Vampire
Angel stood in the shadows watching hungrily as the group of laughing young college kids came toward her down the alley. The group was made up of four guys and a girl. The girl was hanging all over one of the guys and it screamed how badly she wanted to get in his pants. Angel's smile broadened with... Read full Story
ASSEaster5678 2018-10-29 7,417 Group Sex shemale vampire