Sort by
Relevancy

Free Stories

44%
First time with a shemale
I must have been 16 back in the day, but I always looked older so it didn't really affect anyone's judgement in the sex world that I had loved since I can remember jerking off for the first time. I was walking the streets of Amsterdam that day, the Red light Disctrict looked like paradise on earth,... Read full Story
shemale lover 2012-02-14 6,951 first time Stockings Small Tits
80%
One night Transtand ;)
One Night Transtand By BalkanMan990 Published on Lush Stories on 05 Oct 2019 I had no idea she was a trans.. I didn't stop kissing or fondling her when I found out. I went out for a drink at one of the many bars at Croatia,where my girlfriend Sabina and I were staying.Sabina and I had been drin... Read full Story
BalkanLoco91Ri 2019-10-24 8,683 Small Tits Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale Homemade pov cum in mouth
100%
TO BE OR NOT TO BE - PART 4
TO BE OR NOT TO BE - PART 4 by Spanky de Bautumn Part 3. Everybody was working hard for opening night when tragedy strikes and Sunny has to make a decision. Walking back to the hotel, I was lost in thought. I was excited but at the same time scared to death, confused and clear of mind, think... Read full Story
SpankydeBautumn 2021-02-23 2,277 Small Tits Crossdresser Outdoor Fetish Lingerie Mature pov
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 6,116 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade self sucking pov cum in mouth
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 3,678 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov cum in mouth
0%
Tits: A Hands-Off Topic
In multicultural America, there is no place for black tits. Brown, tan, bronze, yellow, olive, red, and white boobs are forbidden, too, on the same grounds, which is that breasts of color--any color that is actually effected by various degrees of melanin in the skin--are fast becoming off limits to ... Read full Story
shemale lover 2011-09-14 3,041 boobs tits erotica
100%
Sports Bar Pre-drink
Sitting on the chair leaning against the bar, Steven sat quietly sipping on his rum and coke. It was a fairly quiet night at the local sports bar he often ventured to after work to wind down from his work shift. Steven looked up at the door as a small group of women walked through laughing and ta... Read full Story
Master VeeJay 2019-09-27 9,196 Big Tits Blowjob Asian Guy Fucks Shemale
60%
Susan's First Time Part 4
The shadows of late afternoon crept across the city when Susan paid the cabbie off. Why had 'he' wanted her to come down to this neighborhood? She looked around with apprehension at the garish lights of bars and adult bookstores flashing in the growing darkness. One or two streetlights flickered on ... Read full Story
shemale lover 2011-10-14 2,990 Small Tits shemale massage
38%
Am I gay?
Please help me. I'm confused and unsure if I am gay. I feel so ashamed of myself. I don't want to be gay but I was molested by my neighbors at 6 years old and from then on I would wear my mom's panties or sniff my sisters while masturbating. Cumming would always make me feel guilty for what I have d... Read full Story
Chinaysissyslut 2020-02-24 6,019 Stockings Teen (18+) Small Tits Crossdresser solo Amateur Masturbation Asian Ladyboy Lingerie Homemade webcams
80%
Getting Fucked by Sasquatch
Bill was about to show up, I had known him from a chat room for years now. I was in his town for work and we had set up this date so we could finally meet each other. I heard a hard knock at the door and when I swung it open, I just stood there in awe. It wasn’t the big beard or really long hair tha... Read full Story
pennypenny 2020-08-21 5,778 Crossdresser Bareback Creampie Fetish Blowjob Big Cock redhead domination Guy Fucks Shemale pov Ass to Mouth cum in mouth
95%
T-Girl University
Jason was apprehensive about starting college, as any freshman would be. His high school girlfriend, Becky, whom he loved dearly, was going to a different college on the opposite side of the country. They had to promised to stay together but Jason was worried; there would be a lot of temptation for ... Read full Story
shemale lover 2012-09-05 14,627 Cumshot Masturbation Blowjob ass licking redhead
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 13,873 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
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 4,101 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
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 7,140 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
66%
Samantha sissy TGTF
Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... Read full Story
Samantha sissy world 2022-09-20 4,290 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
73%
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 24,334 Fetish transformation fiction pov mind control drug interaction mind mindfuck change
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 8,726 Big Tits Cumshot Masturbation threesome Frottage
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 3,194 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
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 5,019 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
100%
The WearFemme
The times between his fantasies have begun to shorten and he knew it wouldn't be long now. One chance glance at an outline in gym shorts as a guys walking in the wind, or seeing a girl with similar features wearing revealing clothing. The thought of it is almost overwhelming now and he has to focus ... Read full Story
Jayde Love 2022-12-01 3,192 Small Tits Crossdresser solo Amateur Outdoor Masturbation Fetish Homemade pov
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 4,960 anal sex Cumshot fingering oral sex small breasts
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 4,830 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
86%
My First Ladyboy
I was working in Bangkok a couple of years ago. As was the normal practice all the guys would finish work on a Friday afternoon and head to the local bar for a couple of beers.. This particular Friday we were in the usual place chatting and having a nice relaxing time......when she walked in....t... Read full Story
shemale lover 2015-05-23 8,356 anal Blowjob Asian
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 3,432 Big Tits shemale Lingerie
91%
My First Ladyboy
I was working in Bangkok a couple of years ago. As was the normal practice all the guys would finish work on a Friday afternoon and head to the local bar for a couple of beers. This particular Friday we were in the usual place chatting and having a nice relaxing time. When she walked in. Taller t... Read full Story
shemale lover 2013-08-09 12,756 Cumshot Asian Ladyboy big boobs
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 2,717 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
94%
The Double Sex For Sissy
Jeff Malville awoke slowly, moaning softly. He almost forgot where he was in that moment where sleep and being awake clashed. However, after that split second, it all came rushing back and he moaned in delight. He was a captive on the Double D Ranch, and even though he was considered an employee... Read full Story
shemale lover 2013-04-10 7,506 Creampie threesome blonde redhead domination double penetration
100%
Florida TG Experience
I had known Jan from High School, we always had an attraction for each other but were dating someone else or married at the time. Jan had actually married a friend of mine and I was envious of course. She at that time had sandy blonde hair, and a body to die for. One evening we had them over for dr... Read full Story
Jon Paul 2018-08-13 10,660 Group Sex Big Tits Bareback Creampie Blowjob blonde Asian Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth double anal
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 4,109 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
87%
They Were Right
They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... Read full Story
shemale lover 2011-12-29 5,626 shemale Big Cock porn
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 8,205 anal ass sucking threesome tits fingering sex blondie
100%
Big Surpise In Small Package
It was a Friday night and I was extremely horny and just my luck my girlfriend was out of town, but I wasn't horny for her I was craving cock. I knew I was bi for a long time and loved to have a nice hard cock to play with every once in awhile. So I decide to call my girlfriend to tell her I was goi... Read full Story
shemale lover 2012-06-11 4,158 anal Group Sex Cumshot Blowjob
64%
Big Cock Heaven
This story is written from the Shemale's point of view. "Jane" is based on a real Transgender woman from California & my friend. She gave me the outline of a meeting she had with "Janardhan." ***** My name is Jane and I am a natural red head blue eyed 34 year old T... Read full Story
sach 2015-11-16 7,122 Big Cock ass licking redhead rimming Shemale on Guy
96%
Making A Man Out Of Tommy
I have two good friends, Brad and Matt who are actually my fuck buddies. Both of them travel for work, so they tend to be gone a couple of months at a time. I have a key to their apartment, so I can let myself in for sex when they are home and to bring in the mail when they are not. I also get to us... Read full Story
pennypenny 2018-08-31 9,677 Teen (18+) Crossdresser Amateur Masturbation Bareback Creampie Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
80%
Karen, My School Teacher Part 1
The Meet By FoxyHosed It all started when we got a new class teacher. Her name was Karen. She was a mature lady and had dark red hair to her shoulders. That first day she wore some short dark blue jeans and a brown blouse. My other classmates started whispering about her. “He-he! Have you seen t... Read full Story
FoxyHosed 2021-01-29 8,635 Crossdresser Fetish redhead pantyhose Mature pantyhose cd
100%
TG girlfriend is my new neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-01-17 3,951 Big Tits Bareback Creampie Shemale Fucks Guy Big Cock Asian Guy Fucks Shemale
100%
TG Neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-04-22 6,305 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale
95%
Mai
When I was twelve I met a new classmate named Dave, he and I became great friends hanging out, joining clubs and what ever else high school kids do. His family was from the Phillipines and he and his sister were the first generation born in this country. His sister Mai is the focus of this story. ... Read full Story
Zöe from Kingston 2018-08-09 11,188 Cumshot Bareback Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale Interracial cum in mouth
100%
Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
Curious_billy 2023-05-07 7,029 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade cum in mouth
0%
A Long Friday Night
Labor Day weekend was coming up. It is the weekend that I let myself go. On this weekend I do something that I save for most of the year. I just do it for myself. This year I was going to try to get a date with a young lady called “Lee”. Let me tell you something’s about me first. ... Read full Story
shemale lover 2012-03-17 3,556 sucking Asian domination jacking off
56%
Big cock shemale from Pune, India
I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in ... Read full Story
Stud4Shemale 2017-05-22 95,462 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
33%
Shemale සුසී
සුසී කියන්නේ Shemale කෙනෙක්.එයා ජොබ් එක විදියට කලේ ඇග විකුණන එක.සුසී ගැන කියනවා නම්,එයාගේ දෙමව්පියෝ නෑ.හැදුනේ වැඩුණේ ආච්චි ගාව.අවුරුදු 15 වෙනකොට ආච්චි අන්ත්‍රා වුනා.සුසී තනි වුනා.එයා කඩේක වැඩට ගියා.කඩේ මුදලාලි අතින් සුසී අතවරවලට ලක්වුනා.ඒත් කඩේ මුදලාලිගේ වයිෆ් සුසීට හුගක් ආසයි.සුසී කෙට්ටු කොල්ලෙක් ව... Read full Story
Malinda89 2017-11-24 9,317 Small Tits Crossdresser Creampie Asian Ladyboy domination
40%
Dating all whole my life
Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... Read full Story
PornoDating 2019-08-15 3,745 Crossdresser Amateur Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock Asian gangbang domination Guy Fucks Shemale Interracial sex Mature Futanari Frottage Compilation Ass to Mouth Cartoon cum in mouth double anal dating life in Mars? life
66%
Sex in the kitchen with my hubby's friend - a cop
Ever since my wedding last year, I enjoy a great time with my hubby who loves me so much and takes care of me so much. Since he is married and having another family, he doesn’t stay with me all the time, but comes and stays at least 2 or 3 days in a month and we literally celebrate those nights wit... Read full Story
Manusha Tranny 2021-10-14 4,960 Small Tits Crossdresser Amateur Cumshot Outdoor Blowjob Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
81%
A pervy uncle invited me to his house at 10 PM..!
It's been 8-10 years now, I had this amazing experience. I was standing at the bus stop in my area/street(my daily routine), one uncle was watching me but I ignored eye contact as I feel awkward the way he was looking at me because I act straight in public and I felt that he's seen my girly ... Read full Story
Cindy Sky 2021-07-20 6,971 Teen (18+) Small Tits Amateur Cumshot Outdoor Bareback Creampie Fetish Blowjob Asian Ladyboy Mature
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 13,723 first time sucking fuck domination
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 13,759 anal Blowjob black fiction
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 6,378 sucking cum massage
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 10,559 Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale Mature
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 5,096 big dick Cumshot Blowjob fingering jerking off
80%
Career Shift
Receptions are not my favourite things in the world to attend. I don't mingle and 'rub elbows' like agents and sales people do. I usually end up at the bar drinking alone, looking at all the phoney people. I am a writer, a sports column writer more specifically. The magazine that I write for is one ... Read full Story
shemale lover 2012-03-06 5,579 Group Sex Blowjob fingering orgasms
50%
Plaid Pleasures - TG
Oh what a glorious time to be alive and horny. The miniskirt is back with a vengeance and the must-have item (for girls with the legs to show them off) was a short cute minikilt. I've never quite figured out why, but I've always found a tartan (or more commonly called plaid in the US) pleated ski... Read full Story
shemale lover 2011-11-05 2,934 sucking shemale cum
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 5,706 Cumshot Big Cock jerking off oral sex cum swallowing
85%
Busted and Hoodwinked
INTRODUCTION Mack and Barry were cell mates in prison which is where they first met. They had both been convicted of burglary and breaking and entering. The befriended each other while in prison and became lovers. Barry was gay and Mack became a bisexual during their time in the same cell. Mack a... Read full Story
shemale lover 2012-09-30 5,745 anal Cumshot Ladyboy oral
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 4,879 anal sex asshole Big Cock
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 4,447 shemale cum ass fucking