Sort by
Relevancy

Free Stories

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 21,063 anal Crossdresser Cumshot Blowjob rimming cd
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 4,351 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
76%
Porn Princess
They say if you are going on a journey of revenge, to dig 2 graves, one for your enemy and one for yourself. I thought I understood the meaning of that saying, but never so much as right now. My name is Dan, and at the age of 21, I had been working for nearly 2 years as a production manager for ... Read full Story
shemale lover 2012-09-02 23,979 Cumshot Blowjob fuck fingering big boobs
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 3,981 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
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 5,061 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
93%
The Tranny Trucker
A gust of freezing wind blasted across my face. I succumbed to worries of frostbite as I walked aimlessly along the side of the highway.\r\n\r\nThe wind of passing trucks nearly knocked me off my feet. This must have been dangerous. It\'s something I should have considered.\r\n\r\nMy parents separat... Read full Story
shemale lover 2013-07-19 6,954 Cumshot ass fucking ass licking oral sex kissing
100%
Towel Boi: You're Hired
Kasey Stevens woke up in his new studio apartment. The five-foot-nine, blue-eyed sissy with ash brown hair yawned and stretched before heading into the bathroom. He showered, taking good care to lather his rosy skin with strawberry scented body wash. He shaved his legs and rinsed off. Then, he appli... Read full Story
Faggyboi and Puzziboi 2023-11-14 5,998 anal Small Tits Crossdresser Amateur Bareback Blowjob Guy Fucks Shemale Interracial small cock big ass femboy
100%
Uncle sweet Lover
Uncle Barney called me this morning and wanted me to keep my evening free. He wanted to meet me at the motel with a surprise for me. I was so excited and could hardly wait. I had to decide on something to wear, but when I thought about it, I realized that I wanted to wear something special. He would... Read full Story
Regina10 2024-02-19 4,775 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
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 5,528 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
88%
Girl from Uncle
Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... Read full Story
Regina10 2024-02-14 5,208 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
100%
Towel Boi: Agreement Signed
Ralph moved the mouse to wake up the computer. He navigated to his legal docs account and downloaded a generic pre-existing relationship agreement. He asked for the spelling of the new hire’s first and last name. “First name K-A-S-E-Y. Last name S-T-E-V-E-N-S.” “Got it,” acknowledged the owner. ... Read full Story
Faggyboi and Puzziboi 2023-11-14 5,903 Crossdresser Bareback Creampie Blowjob Guy Fucks Shemale Interracial small cock big ass sissy femboy
100%
Woman Cross Dresses for Power & Sex
Tucked in the far corner of a dark, dancehall parking lot, Sarah, also known as Robert, was having sex in a car with Joseph, also known as Josephine. Having sex in a car was no big deal. A lot of couples have sex in cars. Yet, if a passerby could see through the steamy windows, a sight to behold, ev... Read full Story
shemale lover 2012-10-09 3,984 sucking Fetish fingering crossdressing
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,711 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
100%
An Unexpected Surprise
When I walked into the bar, I didn't notice her at first; I sat in a booth in a dark corner and ordered a drink from the waitress. The waitress returned with my drink, and when I went to pay her for it, she said it had already been taken care of by the blonde at the end of the bar. I looked, and ... Read full Story
shemale lover 2012-11-21 9,862 Fetish orgasm
71%
A Night of Makeup, Cock and Cum - froam Annamalice
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further, I... Read full Story
shemale lover 2011-11-21 5,145 shemales Group Sex Fetish
100%
A Not-So-Small Piece of Heaven
I'd never really been one for going out to bars to pick up women, but tonight was a bit different. It was my buddy's birthday, and he decided to invite me and a couple of other friends out to go bar hopping with him. Living in Miami, there was always something going on after the sun went down, so th... Read full Story
shemale lover 2012-04-28 3,841 Blowjob shemale handjob
100%
Lady in the House
How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild mannered, and diminutive but highly successful accountant in his 30s ended u... Read full Story
shemale lover 2012-05-12 3,995 Stockings Fetish crossdressing
87%
Feminized By My Mother Chapter 2
My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed. "I ho... Read full Story
shemale lover 2012-07-24 13,175 sucking Fetish fucking sissy
94%
Shemale Ride Along Part 1
I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass. Now... Read full Story
qtball 2016-08-29 12,469 anal tranny Blowjob Big Cock bj asstomouth
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 8,942 Small Tits Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale Homemade pov cum in mouth
84%
SUMMER VACATION by Spanky de Bautumn
In our house, it was a well-known secret that my mother kept her change in the top drawer of her dresser. The same drawer she kept her slips, chemises, panties, and all other satin, nylon, or lacy ladies undergarments. During the summer, my brother and I would run to that wondrous drawer when... Read full Story
SpankydeBautumn 2021-01-22 12,655 Small Tits Crossdresser Cumshot Masturbation Fetish Blowjob Lingerie Shemale and Girl cum in mouth
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 4,353 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
60%
Shemale Chrissy Fucked by a Demon
I wanted to write this the night it happened, Halloween, but I was still so traumatized. I was at my fictional fantasy Sugar Daddy's house alone and already spooked out by the noises of this old hundred-year-old wooden house in this loud thunder storm on what some call "Devil's Night." I had to turn... Read full Story
Chrissy Tunnell 2022-12-01 4,094 Small Tits Crossdresser Amateur Bareback Fetish Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
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 4,884 anal Stockings Big Tits Cumshot Bareback Fetish Blowjob Guy Fucks Shemale small cock
94%
The Babysitter's Secret
The story that I am about to tell you took place on a day that started out very ordinary, but would end up as the least ordinary day of my life. Until that particular Winter day, I thought I knew who I was. I was Peter Fuller -- respected educator, devoted husband, loving father. I had never cheated... Read full Story
shemale lover 2011-10-24 21,114 Blowjob perky tits handjob titfuck
50%
A Night Out
I was at the bar one Friday night after a long, long week at work. It was one of these weeks where at the end you tell yourself you need a drink. I was still new to this town and haven't been out that much so I went to a bar near where I live in case I decided to drink myself into a stupor. I got th... Read full Story
shemale lover 2012-04-19 3,559 Cumshot Blowjob cum swallowing
80%
Becoming Alanna Part 2
Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... Read full Story
shemale lover 2012-07-12 3,888 sucking Fetish Ladyboy rimjob
92%
Lady In The House Chapter. 01
A story by MicheleNylons ( Man in jail is transformed to prison slut.) How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild... Read full Story
✘Transensual✘ 2019-01-11 9,441 Crossdresser Bareback Creampie Fetish blonde Big Cock Lingerie domination Guy Fucks Shemale transvestite slut PRISON FUCKBOY prison sex Prison Bitch
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 24,615 Fetish transformation fiction pov mind control drug interaction mind mindfuck change
100%
The Next Level
Nitromethane It's been a couple of weeks now since I sucked my last shemale cock and swallowed her load, and with enough distractions, it hasn't been too difficult keeping myself preoccupied and my mind off of satiating my new fixation. Still though, I do have my moments when I sit back and imagi... Read full Story
Gwapo67 2022-02-01 5,776 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
100%
I Love To Love You
I Love To Love You Baby By Sabrina G. Langton Author's note: I have published this story on two other sites. I always said it was slightly aurobiographical, but reading it back it is a pretty accurate account of my summer of '88. There are only 3 things that I changed. 2 are itsy bitsy tiny deta... Read full Story
Brina Giselle 2023-09-24 5,016 anal Crossdresser Blowjob kissing transgender virgin romantic earrings
100%
Sweet Sherri
"The fuck you want," the girl hissed through her teeth. Well, it's hard to say. For one, this was the one night of the week at the particular club that was tranny night. Unless the lucky woman was either a straight freak or had been exposed to the scene, there weren't too many people wa... Read full Story
shemale lover 2011-10-31 5,553 Big Tits transsexual big ass
100%
A Close Encounter of the...
Another great tape and another great yank of the crank. Yea, she-males were pretty hot, Tom thought as he hit the eject bottom on the tape deck, but where on earth would he really find one? He had little doubt that if he did find a place where they hung out that there would be more than a few with a... Read full Story
shemale lover 2011-11-13 5,011 Cumshot Blowjob massage
71%
Glory Hole Girlfriend
My boyfriend likes to take me to the local adult bookstore, into the back where the video arcade is. There's always a lot of men there, strangers that we don't know, and I feel funny when they look at me. They wonder why a pretty young woman would be back there. It smells too. A rich sweaty sc... Read full Story
shemale lover 2011-12-18 7,343 Creampie ass fucking mouth fuck
100%
Barbie Jo Adventures Part 5
Friday Night I've gone all week as Joe; no one at work has said anything to me about Monday morning. So I assume I got away without being exposed as a cross dresser. I was working late all week and finally Friday is here. I am so horny and anxious to become Barbie Jo. Hopefully someone will call,... Read full Story
shemale lover 2012-02-18 4,325 sucking Fetish cum swallowing
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 22,782 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,520 Crossdresser hardcore ass fucking cd
89%
Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2016-11-14 18,013 big dick anal sex suck Blowjob cock sucking workplace
84%
First Time: How I Love Cock
The first time I ever sucked a dick was when I was around 12 years old. I was at a sleep over with a friend. We were camped out in his backyard in a tent and he started things out tentatively by asking about my luck with the ladies, which was non-existent. Then he suggested that since neither of us ... Read full Story
wickeddogg 2019-12-11 33,778 Teen (18+) Cumshot Bareback Blowjob cum in mouth
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,243 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 11,375 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
First Time I Experienced Eating a Tgirl Out
So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... Read full Story
AllenB 2022-10-21 5,126 Amateur Big Tits Cumshot Latina Creampie Fetish Blowjob rimming Homemade cum in mouth latina ts
100%
delicious virile male flesh
Tasted delicious virile male flesh… The breeze caressed my swollen nipples giving me pleasant shivers. The two glasses of Riesling had also contributed to my excitement. My crotch was burning as if the disappearing sun had blown all its thermal energy into me. Under my fine lace panties, purple o... Read full Story
hippocampus_171 2023-04-23 5,001 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminisation cum in mouth gaycd virile
66%
The wonderful adventures of miss K: Down by the river...
Miss K and Tracy walked through the park by the Gateway Arch, content to spend a nice spring day enjoying the outdoors instead of another piece of flesh. Tracy had one a pair of short, tight daisy dukes with a light pink crop top that showed off her tight stomach and nice legs. Miss K herself... Read full Story
shemale lover 2011-12-01 4,218 shemale oral ass licking nipples
80%
A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... Read full Story
shemale lover 2011-12-06 11,490 Bareback cum ass fucking slave
100%
And Life Goes On Part 2
So here I sit in my sexy black Miniskirt. The red silk blouse I am wearing shows off my ample sized breasts. Underneath I am wearing a red Satin corset which reduces my waist to a waspy 26 inches. I have on a pair of black satin panties with a matching black lacy bra. The red nylons I am wearing acc... Read full Story
shemale lover 2012-01-10 3,984 Big Tits Fetish feminization
100%
Bar trap Part 2
I was supposed to put on heavy makeup. Starting with the foundation, I applied a generous layer of a brand especially designed for the use on stage, that did a very good job covering up any dark shadows. After I was satisfied with the effect, I used a brush to put on powder and make it all smoot... Read full Story
shemale lover 2012-02-26 3,207 Fetish crossdressing whore
100%
A Dickgirl Part 2
Ginny was mortified. For the first time in her life she hated her body. Why the fuck did she have so little self-control? Why couldn't she hold her body back? Why couldn't she be like normal girls? She cried all the way home, her tears drenching her shirt. She stopped by the time she got home, bu... Read full Story
shemale lover 2012-02-27 6,672 Cumshot sucking Big Cock Shemale and Girl
100%
A Night of Makeup, Cock and Cum
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further,... Read full Story
shemale lover 2012-04-18 4,742 Cumshot jerking off domination Sex Toys cum swallowing
85%
First Time with she-male
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny. S... Read full Story
shemale lover 2012-04-29 4,684 first time Cumshot shemale small cock
100%
Girly
It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. ... Read full Story
shemale lover 2012-09-11 4,407 Small Tits Cumshot fingering oral sex rimming foot fetish
100%
Doctor's Orders
Ever since he was a small boy, James had hated going to the doctor’s office. As he walked through the doors towards the reception desk he felt his stomach tightening, and as he stood there waiting for someone to check him in, he shuffled nervously on his feet. A pretty blonde receptionist walked ... Read full Story
reasonman 2019-08-02 22,634 first time Blowjob ass licking Guy Fucks Shemale foot fetish doctor cum in mouth
100%
The Experience of a Lifetime
My divorce was hitting me really hard. My wife outgrew our relationship and started living her own life and I had a front row seat to everything. My heart and life was upside down. I didn’t go out anymore. Friends and family both told me it was time to get my life back on track and start living ... Read full Story
therefill05 2020-11-30 20,101 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob blonde Big Cock Ebony Uniform domination cum in mouth
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 4,901 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
100%
Karen, My School Teacher Part 4
Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... Read full Story
FoxyHosed 2021-02-17 7,817 Crossdresser Cumshot Masturbation Fetish Blowjob Big Cock redhead pantyhose feet toes legs cock ass pantyhose legs
100%
TO BE OR NOT TO BE – FINAL ACT
TO BE OR NOT TO BE – FINAL ACT by Spanky de Bautumn Part 7. Sunny spent the night with Antonio and the next day they went to Mel and Shari’s for some fun. Antonio had school, so he was up and out early on Tuesday. Mel was in the shower and I was laying in bed, my mind wandering and not real... Read full Story
SpankydeBautumn 2021-03-02 2,538 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth