Sort by
Relevancy

Free Stories

100%
Christy's Fantasy Come True Chapter 6
The alarm went off and Christy rolled over and hit the off button. The clock face was starting back at her flashing 8:00. Since it was Friday she had slept in a bit. Jim had gotten up early and left for work after spending the night. They had gotten into a minor argument last night but came to a... Read full Story
shemale lover 2013-01-30 5,113 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Lady In The House Ch. 08
A story by MicheleNylons (Crossdresser must comply with jailhouse heavy.) "You!!!" Eddie screamed through the bars, then laughed. "Well done girls, quite a show, I really enjoyed that; and so did Michele obviously," he said snickering and pointing at the tent in the front of my skirt caused by... Read full Story
✘Transensual✘ 2019-02-25 5,738 Crossdresser domination PRISON PUNK prison sex Prison Bitch
100%
Marta, Marta, Marta...
Marta, my good female friend I get to eat my wife out once in a while, was curious about my Brianne side and I told her that I would dress up for her if she would fuck me with a strap on. I don't even think I had gotten out that whole sentence when she said ,"Sure!" You have to understand, this is o... Read full Story
smtmsbrianne 2020-09-15 3,262 Crossdresser Amateur Big Tits Cumshot Blowjob blonde Lingerie Sex Toys
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 8,463 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
50%
Lacey gets dominated
thx, get rid of some work, but the pensum will rise again, meetings awaiting ... business as usual. But never mind, I will find some time to play with my sissy slave... thats me lacey Seeing you standing there like this ... I got a new idea. It might bring you up a bit to be ordered to go d... Read full Story
goodgurl34 2022-01-12 1,711 Stockings Crossdresser Blowjob Lingerie domination Guy Fucks Shemale Sex Toys Homemade
100%
Erotic Dreams come true.
You start having intense erotic dreams — and the faces you see is one you don’t recognize but that feels familiar. Mandy was that girl that Chad had been dreaming of, the kind where to see her made a rush go through you like a hot flash. Chad had just broken off a relationship, and his sister war... Read full Story
Jon Paul 2023-05-26 4,875 anal Stockings Big Tits Cumshot Bareback Fetish Blowjob Guy Fucks Shemale small cock
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 5,283 Group Sex Cumshot Shemale Fucks Guy Fetish gangbang Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
100%
Bimbo Bombshell - Chapters 1-2-3
Bimbo Bombshell - Chapter One: Singled Out! Even though it was Friday, the bar wasn't particularly crowded that night. I never knew what hit me. This Gorgeous Blonde bombshell, starts flirting with me right a my table. I found myself wondering why this glamorous beauty, had chosen me. I was... Read full Story
Hardrock51Fifty 2024-06-23 4,743 Stockings Big Tits Shemale Fucks Guy Fetish Blowjob blonde domination Guy Fucks Shemale blonde shemale PDA Public Displays of Affection
100%
Double Wedding
I was about to marry my childhood sweetheart Paula Rother. I loved her and she loved me but it hadn't been straightforward. After school she went to Manchester University while I went to work at a local accountants as a lowly paid junior clerk. She said we where inseparable but during the two years ... Read full Story
shemale lover 2012-11-08 7,238 Cumshot dildo Sex Toys
95%
Late night park visit
It was 11pm on a Friday night, I was driving my car back from a failed meetup with a guy I met online a couple of days prior. I thought it was going to be an amazing night, so I spent close to two hours getting my makeup and hair sorted to look pretty for him when we met. I was wearing a short black... Read full Story
Natalie Bishop 2018-10-08 7,182 Amateur Cumshot Bareback Creampie Big Cock Ladyboy domination Guy Fucks Shemale public Park
100%
Threesome fun
We had invited friend over who has big cock --he arrived and we sat around for awhile talking about sexual encounters of the past --I'm a bi part time shemale cross dresser who is very kinky --anyway it got around to looking around the house and as it happened we stopped in the bedroom , and all o... Read full Story
goodgurl34 2019-01-08 4,413 Stockings Crossdresser Amateur Big Tits threesome Blowjob Big Cock Lingerie domination Guy Fucks Shemale Mature Homemade threesome sex
83%
Imagination 1
I imagine a going on a date with a hot girl and not knowing she has a dick. However, the minute we're in the hotel room that I rented, she places her right heel on the bed and I see her long slimy cock dangling. Man I get super rock hard while I get naked and on my knees and start sucking it. Non-st... Read full Story
Chickzdigmeyup 2019-05-27 3,739 Shemale Fucks Guy Fetish domination
75%
Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... Read full Story
shelli_k18 2021-04-20 8,415 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 5,046 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in 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 4,803 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
50%
The Femininity of the Shemale
Shemales--those transsexuals who have completed the feminization process except for undergoing sex-reassignment surgery itself, having opted to retain their male genitals--disturb some folks. Are shemales to be understood as being women with penises and testicles, as such vulgar phrases as "chi... Read full Story
shemale lover 2011-08-17 3,911 shemales chicks with dicks
25%
Transsexual Actresses Part 2
On the way to Florida, in 1992, Meghan stopped in New Orleans, Louisiana. Her visit to this city lasted an unexpected five years, during which time she began her transformation into a transwoman. A popular nightclub, Papa Joe's, was looking for a replacement for a transsexual who had played Madonna,... Read full Story
shemale lover 2011-09-08 4,905 shemale transsexual porn star
71%
Filthy Little Beast
I had very few memories of my early childhood. The ones I did have were anything but pleasant. I did remember my mother and her blind hatred of my father and myself. She was very tall blonde woman with cold blue eyes named Monica. My mother always dressed in the most expensive leathers and satins in... Read full Story
shemale lover 2011-12-02 12,474 taboo Fetish crossdressing erotic encounters
83%
Caught at Lunch
Only so long can you hide, if you are wondering what the hell I am on about then let me explain. As a part time transvestite dressing is always a thrill as is the joy of turning myself from a very average looking guy into a sexy cock loving slut, but due to where I live the chances to fully dress... Read full Story
shemale lover 2012-06-11 3,827 anal sex Cumshot shemale fingering transvestite
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 11,293 Crossdresser Cumshot Blowjob jerking pantyhose
100%
Discovering Amber Chapter 2
My life is a never ending cycle of tease and denial since I was discovered by Ms. Allison. When I wake in the morning I am curled up in bed with Ms. Allison's naked body while I am dressed in a satin nightgown. I slip out of bed and walk to the guest bathroom where I have to lift up the long nightgo... Read full Story
shemale lover 2012-09-28 3,839 cum oral domination Sex Toys sissy
100%
Angel at a Christmas Party
Angel stumbles along to the upstairs guest bathroom of her friend Helen's house. The downstairs one is full at the moment and she needs to pee really badly. She is also horny as hell after watching one of the guys that is friends with Helen's husband dance and flirt with a bunch of girls that Angel ... Read full Story
shemale lover 2012-11-29 4,968 anal first time party
75%
Lady In The House Ch. 13
A story by MicheleNylons ( Transvestite prison prostitute gets a visit from the Warden. ) I awoke in my cell the next morning unaware of the terrible fate that had befallen my sister Angie. I knew that Steve had sent his henchman Danny to do something to her in retribution for my recalcitrance bu... Read full Story
✘Transensual✘ 2019-02-27 5,372 Crossdresser domination PRISON FUCKBOY PRISON PUNK prisoner prison sex Prison Bitch
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 8,933 Small Tits Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale Homemade pov cum in mouth
80%
Spankys mother cloths torn off on stage reveal she has cockoc
Erotic website remake of the little Rascals short film remake of Beginners Luck. The audience is laughing hysterically at Spanky attempts to open his stuck helmet. Spankys mother, a blonde beauty peeks out at the audience from the stage wing, as the crowd’s loud laughter, nervously biting her finge... Read full Story
kucksissylicktoman 2020-06-16 5,166 Big Tits Cumshot Masturbation Fetish Blowjob blonde Big Cock gangbang Lingerie Guy Fucks Shemale cum in mouth shemale + shemale
100%
Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
Chrissy Tunnell 2022-02-03 3,599 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
50%
My Parisian escapades,
My Parisian escapades, During my many business trips to Paris, I never miss going to see my friend. Sabrina is a Cuban transsexual that I have known for several months. With her, I can let go with complete confidence and live my fantasies. I am one of his friends and lovers who give him the ... Read full Story
sandratvtg 2024-06-25 1,040 anal Stockings Shemale Fucks Guy Fetish Lingerie Sex Toys sissy wig gode pumps rosebud silicone breast split panties
100%
Philippines Vacation with a Dominant Big Cock Ladyboy
I am still in a state of unbelievable joy that I was lucky enough to experience this but I 100% did and I can’t stop thinking about it as I thought things like this only happen in porn or fantasies. Buckle up because this is a wild one and happened in Manila May 2024. I had the opportunity to vi... Read full Story
AllenB 2024-07-14 2,395 Bareback Creampie Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale cum in mouth domination act filipina ts filipina ladyboy
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 2024-07-16 745 Crossdresser Amateur Group Sex Bareback Fetish Blowjob Ladyboy gangbang Lingerie domination Guy Fucks Shemale sissy femboy
100%
A Shemale Vacation Part 2
We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragem... Read full Story
shemale lover 2011-09-05 7,109 anal cumming cum swallowing
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 3,628 Cumshot sucking transsexual fucking
50%
A Murder Misstery
When I rolled out of bed that fateful morning, I had no way of knowing that it would be my last day as Matt McCoy. After showering and dressing quickly (how I long for those days!) I bolted out the door for my train, looking forward to another manic day on the floor. Although I was one of the younge... Read full Story
shemale lover 2012-03-20 5,028 Fetish crossdressing feminization
82%
Bikini Boy
I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage... Read full Story
shemale lover 2012-06-12 15,429 Cumshot Fetish oral sex crossdressing
100%
Britney Story
Yeah, for those of you that have already read it, this is just my "Oops, I Did It With Britney" story that has previously appeared in four separate parts in the "celebrities" section, but I've put it on here for a couple of reasons. For one thing, I've noticed that the stories in... Read full Story
shemale lover 2012-09-25 9,061 Cumshot sucking Creampie shemale
50%
Discovering Mistress Sarah's World Part 5
Chapter 13 Sinking Deeper Into The Feminine World *** Prologue - Joe has made a trip down south to visit for the first time, his online Mistress. Over the past few years she has slowly feminized him with the help of Miss May. Upon his arrival at Mistress Sarah's house, she puts his feminization i... Read full Story
shemale lover 2012-10-03 3,705 Group Sex oral fingering domination
66%
Discovering Mistress Sarah's World Part 9
Part 9 -- The Final Part Chapter 23 Leaving Work Josie's last week at work and concluding week of his normal life went quick. At work he spent time getting things in order for the next unlucky person to take over his job. Mentally he was already checked out of work. All he cared about was gett... Read full Story
shemale lover 2012-10-04 3,966 Fetish ass licking domination
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 11,000 Fetish crossdressing feminization
90%
The Perfect Choice
Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during the day or tiny shorts and vest tops when they were at home together. She did everything she could to t... Read full Story
shemale lover 2013-01-10 6,517 hardcore Shemale Fucks Guy Blowjob ass fucking domination
100%
Boi Toy
They met me off the train late in the afternoon. Their welcome was warm and friendly. I was exhausted from travelling and spent the evening in wonder as we first had drinks with friends of theirs at one home then all went out to eat at a restaurant, then back to another friends home for more drinks.... Read full Story
shemale lover 2013-01-29 5,988 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
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 5,310 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
73%
Nancy the hot and sexy TS in Pattaya
Hi this is Ris, this is my third story. Well Last year I went to Thailand on lone trip. I went directly to pattaya and had rest and went to Walking Street in the evening. Was visiting many nude bars, ts Bars, dance bars. but while walking on the street one particular girl catch my attention. s... Read full Story
Stud4Shemale 2017-05-22 9,470 Big Tits Cumshot Shemale Fucks Guy Ladyboy Guy Fucks Shemale cum in mouth
100%
Porn Cinemas and GinaG
I really like porn cinemas, there is a certain seediness and sleaziness about them that makes them alluring to me. My problem is that living as I do in the south of the UK, there are no porn cinemas anywhere near me. Fortunately, I travel in my job quite a bit and so can get to cinemas in Birmingham... Read full Story
GinaG 2019-01-08 3,400 Stockings Crossdresser Amateur Cumshot Masturbation Blowjob Lingerie Mature cum in mouth shemale + shemale
87%
A Virgin Crossdresser
I was newly turned 18 never even kissed a girl let alone had sex. I had been crossdressing for about a year and had stumbled upon a site called tvchix which where I spent my nights in chat looking and getting an insight into what this world could offer. Bit of background I had named my alter eg... Read full Story
Jessicaxx91 2020-02-06 11,937 Crossdresser Amateur Fetish Lingerie Guy Fucks Shemale cum in mouth
93%
MILF Alessia Travestita finds a bottom boy
I was several days into a cruise to New Zealand and Australia with my wife. This morning my wife went on an excursion that I had no interest in, so I had the cabin to myself. I hadn't had any sex with my wife in the last 3 days due to the activities such as the various jaunts to Auckland and the sur... Read full Story
darrell 2023-08-13 6,154 anal Cumshot Shemale Fucks Guy Fetish blonde Big Cock domination Mature deep throat cum in mouth sandals
100%
About Jack and Diane
Thanksgiving was over the college kids are returning to school and Las Vegas has slowed down from the busy restaurants and overcrowded casinos. It’s the best time of year to see a nice show for less. Jack’s friends had all taken off with families and he had time to think about how lonely he really w... Read full Story
Jon Paul 2023-12-20 6,780 anal Cumshot Bareback Fetish threesome Lingerie Guy Fucks Shemale small cock shemale fucks shemale cum in mouth shemale + shemale
100%
Nikki's Massive Strap-on
A quick recap in case you haven't read my previous stories. My name is Kacey. I'm 20 years old, white, 5'10" and 150 lbs. I have straight, shoulder length dark brown hair, light brown eyes and a thick, 6" cut cock. My girlfriend is Hannah, who also 20 years old and stands 5'10" weighing in at 140 lb... Read full Story
KaceyKlarissa 2024-02-23 4,824 anal Crossdresser Big Tits Cumshot Fetish Big Cock Lingerie Shemale and Girl domination big ass Futanari sissy cum in mouth
50%
The first requirement of a deal with Dominatrix Persephone.e
There was a number of requirements before I even consider'd fucking that sissy ass, firstly, I expected dedication to be shown and to prove that the sissy could obey my orders, after a trial period, then I consider to force my big dick down the throat of the that sissy, and then fuck brutally and ex... Read full Story
Dominatrix Persephone 2024-06-21 1,296 anal solo Cumshot Masturbation Shemale Fucks Guy Big Cock Shemale and Girl domination Mature sissy shemale fucks shemale teen (18+)
100%
Meet Barbies Sissy
Imagination and fantasy can be a wonderfulescape as I am about to relate to you but let me first set the stage. Like many, I have been crossdressing privately for many years. My desire to wear panties, stockings, garter belts, slips and bras started in my pre-teens however, I stopped for a numbe... Read full Story
shemale lover 2011-09-18 3,343 cum dildo ass fucking
62%
Man Is Humiliated By Escort
I am a very adventurous, open minded married guy. I am 6'2", 150lbs and I have a 5" cock. My wife (Mary) is great but she is very straight laced and doesn't like to have sex but twice a year so I decided to look elsewhere to fulfill a few fantasies. I am sure my size and stamina have a lot... Read full Story
shemale lover 2011-09-30 7,125 sucking Big Cock cum domination
100%
Becoming A She-Males Bitch Part 2
After last nights ordeal I was given something to drink and taken to a bedroom upstairs. What I drank must have had some kind of drug in it because I was knocked out. I bet I was asleep in just a couple of minutes. I barely even remember lying down. When I woke up I was naked, sore as hell and fe... Read full Story
shemale lover 2012-01-04 8,832 cum oral domination
100%
Becky's Video
I suppose I was the one that first mentioned porn to Nikki. We'd been chatting on a girls' night out and laughed abut how I'd never found any porn in the house. She giggled and said I was bound to find some sooner or later -- all men had some, somewhere. A few days later, I'd completely forgotten... Read full Story
shemale lover 2012-02-25 4,432 Fetish orgasm domination crossdressing
100%
A Game within a Game Part 1
Epilogue Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter. Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fas... Read full Story
shemale lover 2012-03-05 14,198 Fetish bdsm crossdressing bisexual
66%
Cassandra Chapter 1
Cassandra is a tease, a flirt, a slut, a girl who lives very much for the moment. Unconcerned with propriety or fashion trends, she dresses in clothes that go right for the jugular of a fetishist's libido. Spandex, leather, latex, spike heels, corsets, overdone hair, make-up and fingernails - these ... Read full Story
shemale lover 2012-03-27 5,869 sucking fuck orgasm crossdressing
100%
E is for Erica
I was surprised. Very surprised. I mean, in those circumstances, in that situation. Late in the evening, in a hotel just outside Cardiff, I was there for an interview. I mean, the interview was the next day. TKB were a big firm, still are. I could have driven to their Head Office early the next morn... Read full Story
shemale lover 2012-03-30 2,841 Crossdresser Cumshot Lingerie cum swallowing 69 position
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 5,531 Cumshot oral sex deepthroating crossdressing
100%
Birthday Present Chapter 2
Her Side I ran my fingers into Victoria's beautiful blonde hair and pulled her glossy lips against my labia, pushing up to meet her soft tongue as she probed my wet slit. She knelt beside the sofa, her face buried in my nest, her blonde hair spilling across my stomach, her silky blouse tight agai... Read full Story
shemale lover 2012-06-16 3,291 Cumshot oral sex Sex Toys