Sort by
Relevancy

Free Stories

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 4,329 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
90%
Camming Down the Rabbit Hole Ch. 08
A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... Read full Story
Dani_does_Dallas 2021-11-15 3,885 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov cum in mouth
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 4,199 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
100%
My story, more or less pt.3
Earlier on, when I was scouring through various drawers and closets for feminine clothes in my home I have stumbled upon two old skipping ropes. "A fun time" I thought to myself, not giving them another look and continuing with my search. Little did I know they would become the backbone of my "sessi... Read full Story
Thigh_High_Boi 2023-01-06 3,635 Stockings Masturbation Fetish Ladyboy Lingerie Homemade pov
90%
How I became a cute femboy CD part 4
My legs finally started to work again and I turned and was about to walk to my bedroom when Kevin’s voice stopped me. “Come on, Natalie, you know you want to. You have been crushing on David ever since he moved here.” “You’re an asshole, Kevin. You know that. You are a total asshole! I tho... Read full Story
Cute_Femboy 2016-04-05 12,446 first time cumming crossdressing cd sissy cumshot in mouth
100%
My story, more or less pt.2
So there I was, a boy with a desire. (Refer to pt.1 for context) A few months went by from the "initiation" and I've progressed quite a bit I have switched from shemale porn to femboy porn, to relate to the main characters more. I have also scoured every closet in desperate search f... Read full Story
Thigh_High_Boi 2022-12-23 5,255 Stockings Blowjob Ladyboy Lingerie Homemade self sucking cum in mouth
88%
My first time as a Femboy CD pt 2
David ordered me to dance for him and I hurriedly got off the floor and walked over to the radio and turned it on. I changed the station from an alternative rock station to a top 40 one, which was better for dancing. After I selected the station I moved to the center of the room and started to dan... Read full Story
Nicole_femboyCD 2014-12-03 21,051 anal Crossdresser Cumshot Blowjob rimming cd
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 8,461 Big Tits Cumshot Masturbation Uniform Frottage
100%
Camming Down the Rabbit Hole Ch. 07
Opening my eyes I struggled a little as the residual cum on my face from last night’s show hadn’t been fully wiped off, I felt the dry and crusty leftovers crinkle on my skin, but couldn’t help but smile to myself as I remembered how it had got there. The intensity of that orgasm had been on another... Read full Story
Dani_does_Dallas 2021-10-22 6,315 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade self sucking pov cum in mouth
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 3,468 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
100%
Sexual fantasies on tiptoes
Sexual Fantasy on tiptoes when I was a teenager, I began to like live female gymnastics and ballet, and I had a good feeling about the posture of women straightening their toes and leaning their heads back, my intuition tells me that this is what happens when a woman has an orgasm, and as an adult I... Read full Story
Oldslut Sissy 2024-04-03 4,917 Crossdresser solo Amateur Masturbation Asian small cock sissy self sucking
100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 5,279 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
100%
Camming Down the Rabbit Hole Ch. 09
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... Read full Story
Dani_does_Dallas 2022-03-22 3,425 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
Roberta, Molly and Ed
Friday "Commander Cromartie?" Lt. Commander Edward Cromartie, USN, turned toward the voice that had spoken his name. He saw two female naval officers, a tall willowy light-skin Black woman, and a short Asian one. The Black one was wearing the uniform of a full commander, the Asian of... Read full Story
shemale lover 2012-09-04 5,342 Cumshot threesome Blowjob Big Cock condom sex
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 14,096 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
75%
Flowers in the Heart
Chapter 1 "Hey Scott, Fauna kind of likes you," Jenna said, snickering. "Hey Jenna, it hard to hear yourself over that echo?" Scott said as he caught the football, and then heaved it back to Ronnie. "Huh?" Jenna asked, puzzled. "Yeah, your head up your ... Read full Story
shemale lover 2012-11-11 10,430 anal tranny Cumshot oral
100%
Far Eastern Adventure
He was transferred to the Far East with no real choice in the matter. His boss never took no for an answer and rarely gave him the opportunity to try. She had been acting strangely for the last few weeks, eyeing him oddly as if trying to unravel some hidden mystery within him. This strange perusa... Read full Story
shemale lover 2019-10-20 8,244 Cumshot tgirl nipples
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 6,559 sucking cum massage
100%
A Schoolgirl Story Chapter 2
I must apologise for the amount of time that it has taken for the second chapter of this story to come out. I have to admit that I had kind of abandoned it, but all your lovely feedback comments made me decide that I couldn't leave this one hanging. So thank you to everyone who wanted more of Wendy,... Read full Story
shemale lover 2012-06-05 8,505 Group Sex Cumshot oral sex assfucking
100%
Casino Girl
I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... Read full Story
Jon Paul 2022-01-03 2,915 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
50%
A Fantasy - Part 3
Sharon put her cell phone back into her purse, turned to Paula and I and said "I'll be right back, with the Chinese food!", gave us a wink and took out her wallet, grabbed some money and then went off to get our dinner. Paula was sitting on the floor, she leaned back on her left elbow and started... Read full Story
swollenrooster 2023-09-20 5,279 Group Sex Cumshot Shemale Fucks Guy Fetish gangbang Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
100%
Don't Avoid Daddy
It feels like I haven't been used in ages. I'm too much of a scared sissy. I find guys from all over, talk, email, text sometimes. But when it really comes down to it I get too scared. I've been with this guy before, his cock is soda can thick and he's really rough. The day after my first encounter ... Read full Story
shemale lover 2012-10-23 5,827 Cumshot oral sex deepthroating
100%
Flowers in the Heart Part 2
Chapter 1 "Hey Scott, Fauna kind of likes you," Jenna said, snickering. "Hey Jenna, it hard to hear yourself over that echo?" Scott said as he caught the football, and then heaved it back to Ronnie. "Huh?" Jenna asked, puzzled. "Yeah, your head up your ... Read full Story
shemale lover 2012-11-11 6,272 sucking oral sex facefucking
88%
A Schoolgirl Story
Jason Sheen was eighteen when he moved to River Falls with his mother. Ever since he was a small child Jason had lived with just his mother, Felicity, and he could no longer remember anything about the father who had abandoned the two of them when Jason was just three years old. Fortunately, Felicit... Read full Story
shemale lover 2012-06-05 14,920 cum oral jerking off crossdressing
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 5,506 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
100%
Neighborhood Restaurant Surprise - Kimi
I - The Meeting In the neighborhood restaurant I frequented weeknights after work, I had developed a friendly relationship with several of the college kids who worked as servers. Always having been attracted to the most feminine and petite of girls, dark, almond shaped eyes being a super plus, I ... Read full Story
shemale lover 2012-04-11 5,146 anal sex Cumshot fingering oral sex small breasts
60%
The Clinic
I got out of my cab and looked up at the Clinic. It was a small, nondescript hospital. I was still pretty nervous about this treatment since I wasn't even sure of the details. But it was either this or go under the knife. This problem had to be dealt with. I picked up my bag and went into the lobby.... Read full Story
shemale lover 2012-05-02 5,891 Cumshot Big Cock jerking off oral sex cum swallowing
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 5,543 Crossdresser Cumshot Fetish Blowjob gangbang
85%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 118,745 hardcore Cumshot sucking bdsm domination
100%
Every Year
Imagine me. A slim eighteen year old boy, dressed. I mean Dressed. Dressed up that is, in my sister's clothes. I felt good, very good. In fact I felt incredible. I had done this several times before when my parents had been away but never to this extent. They were away for two nights, visiting Uncle... Read full Story
shemale lover 2012-04-22 5,524 Cumshot oral sex deepthroating crossdressing
90%
On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
shemale lover 2012-09-01 11,291 Crossdresser Cumshot Blowjob jerking pantyhose
100%
Angel Chapter 6
This is an entry in the Literotica Winter Holiday Contest, and is part of an ongoing series on the life of Angel Jones, a beautiful young T-girl in London. For more detailed information on her and on the other characters who appear in this story, please see previous episodes. Angel Jones was uns... Read full Story
shemale lover 2012-12-01 4,243 Cumshot oral tgirl
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 11,386 sucking Fetish transsexual
87%
Finishing School for Shemales
Mistress K looked at the school report and smiled. She wouldn't describe herself as an evil bitch, but plenty had. She was proud of her position. Headmistress of the Finishing School for TGirls. So many beautiful shemale girls had left her careful administration and gone on to happy lives, or ... Read full Story
shemale lover 2012-08-09 10,504 shemales Cumshot domination oral sex
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 6,568 Cumshot Fetish oral sex cum swallowing
60%
A Ski Bunny is Born Chapter 3
Kim and I are thrilled that so many people are enjoying reading about our adventures. We have received so many really nice e-mails from lots of lovely people, its good to know you girls and guys out there are enjoying them! We had promised each other a trip to Europe but hadn't really made any fi... Read full Story
shemale lover 2012-06-22 8,279 Cumshot Sex Toys 69 position handjob
80%
Fifi's Long Wait
Around about 3 weeks ago, Sid had managed to acquire his very own maid; however, 'she' was not your normal run of the mill domestic worker. Oh no, Fifi liked to dress as a maid to fulfill her submissive cravings and the most notable difference was the fact that she had a penis. When working as a mai... Read full Story
shemale lover 2012-08-03 4,752 Cumshot oral sex Sex Toys
96%
New Job, New Life as as Sissy Slut Chapter 2
I was left lying on the floor, my face completely covered in cum. I was wearing lingerie and a dog collar and I had just been fucked long and hard by my "boss." My virginity had been forcefully taken. The thing is that I loved it. I loved being manhandled by this muscular man and I really ... Read full Story
shemale lover 2012-12-23 7,419 Cumshot Uniform Lingerie ass fucking domination
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 13,926 first time sucking fuck domination
100%
A Flash of Lace
The insistent ringing of the phone broke my concentration and with great annoyance, I climbed off the bed and picked up the receiver. "Hey little brother!" My sister's sparkling voice filled my ear. "Di, Is that you?" I exclaimed happily "Got any more sisters I don'... Read full Story
shemale lover 2012-03-03 6,138 Stockings Fetish dressing
85%
Whores and Pimps - Part I
Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... Read full Story
shemale lover 2012-05-13 7,991 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
33%
Click, click, click....
Click, click, click…the sound of high heels contacting a hard surface has always attracted and aroused me. Whether it’s on tile floors in a hallway, the concrete of a parking ramp or the asphalt of a mall lot, I turn in anticipation to drink in some pleasing eye candy. How short will th... Read full Story
shemale lover 2012-06-09 5,281 anal Cumshot oral deepthroating
81%
Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
shemale lover 2015-02-27 7,032 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
66%
The Coma Girl Brain Transplant
[This frivolous story is something I put together as an entry for a comedy competition earlier this year, not to be taken at all seriously, a bit more sci-fi than erotica, more of a mind-fuck than anything else so it’s not jerk-off material but hopefully some of you might still enjoy it] Thankful... Read full Story
cara_elaine 2017-12-19 6,514 Crossdresser Uniform domination
50%
DATES NUITS
My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... Read full Story
Femboy 2021 2023-02-07 1,348 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial Sex Toys cum in mouth
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 8,443 anal ass sucking threesome tits fingering sex blondie
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,636 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
A Night Out
One night I was out on the town. I headed out on my own as all my mates where shacked up with their girlfriends. It used to agitate me that my mates never came out anymore. It didn't take me long to get used to it. I'm an attractive guy in general, a little on the shy side but still did alright for ... Read full Story
shemale lover 2011-10-05 5,162 anal Cumshot oral
100%
A Job in the Theatre Chapter 14
Sarah and Paula shared at drink as they tried to decide what to wear for their date. "Every good outfit starts with lingerie. What do you think of these?" Paula asked holding up a pair of baby blue panties. "Nice. But I really think these will be better" Sarah said holding up ... Read full Story
shemale lover 2012-03-14 2,639 sucking shemale kissing
100%
The Shop
I lunged backwards to get more of him in me. I heard him grunt as half of him slipped passed my tight sphincter muscle. The pain was in the back of my mind, somewhere but this unbelievable feeling of lust had taken over me. I looked over my shoulder (what a sight that must of been, a 18 year old ... Read full Story
shemale lover 2012-04-12 3,745 anal sex Fetish crossdressing facefucking rimjob
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 5,441 Cumshot Blowjob oral sex
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 17,292 Crossdresser sucking Big Cock ass licking big boobs
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 4,335 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
83%
Tilted Kilt Chapter 4
Like most mornings after a late shift at the Tilted Kilt, I awake around 11 am and lay in bed as the day comes into focus. The sheets felt cool on my nude body and I realized my roommate, Shari, had left the air conditioner on before she left for work. It's Summer in San Diego and the days of late h... Read full Story
shemale lover 2012-01-25 3,624 Cumshot sucking transsexual fucking
50%
Taping a Train
Ever since I took the leap and became and transformed my body into the one I was supposed to have I have never been happier. I love my soft skin, long dark hair. When ever I can I will look in my mirrors at home while naked and rub my hands up and down my body, feeling my big D cup breasts then runn... Read full Story
shemale lover 2012-04-12 3,133 anal Cumshot Uniform gangbang oral
100%
Threeway Heaven
Times were tough and I took a job as a bouncer in clubs on weekends. It was a pretty boring job most nights, and frustrating having to deal with drunks all the time, so my boss sent me out to a gay club for a change of pace. Also, I was one of his few workers who wasn't homophobic, and therefore les... Read full Story
shemale lover 2012-05-10 3,221 Group Sex Cumshot sucking fingering