Sort by
Relevancy

Free Stories

77%
Three tgirls in one day
Three times today with 3 different tgirls :) wow what a day! the first was a big Brazilian tgirl, nice large tits and very sensitive nipples that she liked to have squeezed while I sucked on her breasts or her 7" clitty For the main event she took me in 2 positions, on my back with my legs o... Read full Story
xanykeyx 2014-06-06 4,090 tranny dildo Sex Toys strapon post-op
87%
My 1st time with a shemale
I always had the fantasy to be with a shemale, and today i gained the guts to go to a shemale. I saw the add in the newspaper and called, she was a brazilian (ussually the best ones are brazilian :) ) When i arrived to her apartement, she had a beautifull lingeri, and i noticed her big tits, my co... Read full Story
zongf2008 2014-09-02 4,623 first time ass suck shemale dildo
83%
MY FIRST TIME WITH A SHEMALE - 2
DEAR READERS I DON’T KNOW IF YOU LIKED MY FIRST STORY AS THERE WERE NO COMMENTS ........ !!! After we finished our late dinner in the very cosy position she whispered “wanna have some wine honey?” I replied “I’d love to”. She got up leaving me sitting on her bed and poured two large glass-full of... Read full Story
Lisawantsu7 2014-09-02 6,308 hardcore Creampie Big Cock ass fucking Shemale and Girl
100%
Double Anal With a shemale
....He answered the door and there she was beautiful as ever. He had just paid 500 dollars to have a transsexual e****t come directly to his door and greet him. She had on a long pea coat and thigh high boots. When she took the pea coat off all she had on was a one piece swimsuit. Her tits were a 36... Read full Story
shemale lover 2015-04-29 5,126 tranny suck Big Cock ass fucking dp precum
100%
Angel and Karly 01: Her Girlfriend Has A Dick
Last week Angel had walked in on Karly when she was in the bathroom. Karly had always been very shy around Angel. Now Angel could see why. Angel had a secret. And seeing Karly standing up to pee, with a dick between her legs… well Angel was very surprised. Karly looked up, shocked. “Hey!” she tried... Read full Story
shemale lover 2015-05-01 4,103 Teen (18+) Cumshot suck Blowjob shemale oral sex
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 7,007 Big Cock ass licking redhead rimming Shemale on Guy
97%
Purple Kiss, part 3
Continued... As I reached out for Tiffany's hand, she snagged the towel I had wrapped around my waist and threw it to the floor, “no need for that, cumslut.” The group of women surrounding the doorway applauded once again then dispersed. Most of the women headed downstairs, but Janet, Kimb... Read full Story
Transadmirer 2016-01-15 6,953 Shemale Fucks Guy Fetish Blowjob cum gangbang domination
59%
NORTH HOLLYWOOD GAY BATHHOUSE
Hi so the first time i went to a bathhouse was when i was 18 , i was dating a 44yr old dominate top tranny (Tina) who had the biggest uncut latino thick cock, her cock was the one that made me not only give up on girls but she turned my body and mind into a complete bottom sissy , my butt became her... Read full Story
daddyssissyla 2016-02-22 12,708 anal submissive sissy bbc doggy styду
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 12,138 first time cumming crossdressing cd sissy cumshot in mouth
87%
Threesome for Desi
After months of looking for someone to join us for a threesome, we finally found someone and he is coming over tonight. We are all going to meet at your place so I get over there right after work to get ready. We both take a shower and get dressed before he arrives. We sit on the couch together as w... Read full Story
b0099b 2016-04-27 4,781 anal threesome cd Desi
71%
Cd Shazza (chapter 3)
Hi everyone I hope you all read chapter 1 and 2 because this will make a lot more sense if you did, I wish I was a little better at getting things down in words, these stories a part of my life I would not change but I am loving telling everyone about it the men and the women that I have had sexual ... Read full Story
cdshazza 2016-09-20 3,986 Stockings Crossdresser sex swallow spunk undies
89%
Car Park toilets meet
It was early Sunday Morning , when I had decided to go for a drive into the Lakes , typically soon after setting off I needed the toilets , as luck would have it there was a small village with a car park and toilets not too far off , so quickly stopping I went in , surprisingly as it was quite early... Read full Story
jakuk 2016-10-26 9,275 anal ass fucking cumming casual sex public toilets
71%
Peepshow
The club owner shoves you into the room and you hear the door lock behind you. You are locked in and feeling very vulnerable. “He didn’t say anything about this” you think. The stiletto heels of the black platform heels click on the floor and your arms are crossed over your breast protecting them as... Read full Story
Kraven Moorehead 2017-01-30 8,452 jerking off Sex Toys cd sissy Voyuer
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 95,234 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
83%
Las Vegas Swingers
It had been over 6 months since I seriously dated someone, and I was getting depressed and in a rut. I had directed my attention to my work and it kept me from feeling sad about my loss of someone I almost married. I had met a transsexual girl that absolutely adored, but she was tragically killed. (... Read full Story
Jon Paul 2018-06-11 9,962 Amateur Guy Fucks Shemale Mature Ass to Mouth cum in mouth double anal shemale + shemale
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 9,609 Teen (18+) Crossdresser Amateur Masturbation Bareback Creampie Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
100%
All Woman and More
It was one of those soft southern nights you hear about in movies and old soft rock songs. I could smell the long leaf pines and the moon was nearly full. I had been on my own for so long that it rarely bothered me as it did in my youth. That lonely feeling that never quite goes away. Now it came on... Read full Story
Windmillchaser 2018-09-20 10,402 Bareback Shemale Fucks Guy Big Cock sensual romantic encounters Erotic Fiction
66%
wishing
When I would get off the bus from after school activities, I would always walk through this truck stop on I-94 east of the Twin Cities. I would always look at the truckers parked for the night in the back. I always wondered what would happen if I brought my desires and fantasies to life for one of... Read full Story
cd4fun715 2019-01-08 2,649 Crossdresser Amateur
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 5,460 Crossdresser domination PRISON PUNK prison sex Prison Bitch
95%
She Wood in the Wood
"Alright, juniors and seniors to the white bus please." Mr Jacob's voice cut above the rabble of the moving crowd. All 50 of us filed into the large vehicle, talking loudly, a mixture of excited comments and loud complaints. It was field day, which meant the whole school was going to take up an e... Read full Story
ASSEaster5678 2019-03-18 6,959 Shemale Fucks Guy public natural
69%
TS Fiorella in Frankfurt
Recently I was visiting Germany for a conference. I was staying in the city close to the train station and checked out the red light district nearby. Walking through the red light district is an experience, on every corner and many places in between there are multi storey brothels where you can wan... Read full Story
xanykeyx 2019-10-24 11,052 Shemale Fucks Guy Ladyboy tgirls frankfurt crazy sexy
100%
Estelle
Estelle sat before her dressing table, putting the finishing touches to her makeup. She had prepared herself as well as she was able, as her lover tonight was her benefactor – as the kept “whore” of Marcus Smith she owed her whole self to him and indeed, she loved him, but more than that, she loved ... Read full Story
kathysmokes1 2020-08-13 4,105 Stockings Crossdresser Bareback Fetish Big Cock Lingerie
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 8,918 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
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 8,501 Crossdresser Fetish redhead pantyhose Mature pantyhose cd
90%
Saving My Marriage
I love to write Erotica. For story requests please send me a private message or email noirenoire10@gmail.com It was our anniversary. Today made five years that my wife and I have been married and we were taking a road trip to celebrate. I chose our destination but I let her choose all of our a... Read full Story
therefill05 2021-02-16 5,769 Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob Big Cock Ebony domination Sex Toys cum in mouth
71%
Shy Marcy
After becoming acclimated to my new friends and their life choices, My friend Sammi noticed a girl in "our" restaurant that always sat alone and made no eye contact. We all discussed her and everyone determined that someone should approach her and make her comfortable. One guess who was elected... ... Read full Story
GirlyArms 2021-02-22 2,380 Group Sex Fetish Blowjob transgender skinny shy big load muscles
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 2,639 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
100%
The Biology of Music - I fucked my trans substitute teacher
I was never strong in school. I wasn't very interested in what we were being taught, and the teachers liked me enough to not give me too hard a time about it. I attended an all boys school. It was actually quite a religious school which makes this story all the more surprising. I was in the middle c... Read full Story
terrifictim 2022-01-03 3,546 Creampie Guy Fucks Shemale feet licking first time with a tranny teacher student
100%
How I Became His Office Fucktoy
Until this job ended last year, every day at my lunch break I would service one of my many Daddies in his office in the building where I worked. He'd always slip me a few bucks, a $20 or even $50 afterwards, not as a payment for sex, but as a "tip" "for all the hard work you do here," he says. I wor... Read full Story
Chrissy Tunnell 2022-02-18 3,453 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature cum in mouth
50%
My first time as a female
I was playing with my tiny dick one morning. Thinking what it would be like to have a pussy and some tits. Wondering what dick would taste like. These thoughts made me feel horny. I got a boner. K sneaked into my parents bedroom. Looking for Mothers sexy underwater. I found her panties and bras. I a... Read full Story
2BWoman 2022-09-07 4,479 Crossdresser Big Cock Ladyboy domination
100%
Pizza Delivery
She wraps her hands around the back of his head and shoves her cock harder and further into his throat. She can hear him gag and saliva burble in his throat. “FUCK I’ve needed this!” She says, pulling her cock out of his mouth and letting him take a deep gasping breath. “Holy fuck,” he says, cat... Read full Story
ghostpeople 2022-11-22 5,601 Bareback Shemale Fucks Guy Blowjob Big Cock Uniform Ass to Mouth cum in mouth
100%
Used in a hotel room
This is a recurring fantasy I have about being used in a hotel room. I’m working on making this a reality but for now this will have to do. I travel a lot for work and end up in many cities across the world. Usually I am out and exploring bars and restaurants. Always ends with me jerking off alo... Read full Story
slvr2291 2023-01-11 4,437 anal first time Big Cock fantasy Surprise
83%
A Stay At Cousin Clare's
As a teenager I always used to spend about ten days each year with Cousin Clare and her parents. Clare wasn’t actually my cousin, but her mother and my mother were at school together, and it was a convenient way to refer to her. Clare was an only child. At the time of the following exciting adve... Read full Story
lacemint 2023-08-29 6,087 Crossdresser sissy cum in panties panties crossdresser knickers Cousins clothes
100%
The Interview
The Interview By Sabrina G. Langton *** 'A crossdresser goes on an interview in lots of pink, of course she gets the job' 'Author's note, just a quick little story with some really graphic sex, and a little tiny moral. I hope YOU like it.' *** "Okay, sit, sit, let's get started. S... Read full Story
Brina Giselle 2023-12-04 5,928 anal Crossdresser Blowjob heels cum in mouth pink dress