Sort by
Relevancy

Free Stories

100%
My 1st Time was Not the Only Time.
One late night after hitting the slopes and partying I left my friends birthday party feeling extra horny. It was about 6 or 7 in the morning now and after having no luck finding an escort I responded to an ad on craigslist posted by a trans woman. I figured two things, this dick isn't going to suck... Read full Story
LesFuax 2019-02-16 9,123 first time Small Tits Amateur Latina Bareback Creampie threesome Blowjob Big Cock ass fucking barebacking barebackedshemales first time with a tranny raw anal raw dick raw fucking firsttime
100%
Sissy Slut and Stepdads part 2
My mother kicked Frankie out and swore that he was the last loser she would ever date. She believed that we were still having sex, and she was right. Pure raw animal lust drove us, and It was even better when we sneaked and got. That nervous adrenaline mixed with my passion and made me super horny a... Read full Story
Regina10 2021-02-15 4,100 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to Mouth
100%
The four of us
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
Jon Paul 2021-08-02 4,197 Group Sex Big Tits Cumshot Bareback Creampie Blowjob Big Cock Guy Fucks Shemale Ass to Mouth
80%
TG Girlfriend moves in (part 2)
My wife Lydia and I have been married about 9 months, we have a very close TG friend, Joanne, that lives next door and every once in a while, we get together, and all go out and enjoy. We have had sex together, and when Lydia is away Joanne, and I are together at every opportunity. Joanne and I work... Read full Story
Jon Paul 2022-01-21 3,465 Big Tits Cumshot Bareback Creampie threesome Blowjob Shemale and Girl Guy Fucks Shemale
100%
Becoming Kacey
I indulged my crossdressing opportunities as often as I could, but as time went on, the chances grew further and further apart. Although I couldn't play dress up in my alone time, the fantasies never seemed to cease. When I entered high school, I dated girls and enjoyed the young passions that teena... Read full Story
KaceyKlarissa 2024-01-16 4,054 first time Crossdresser Amateur Homemade sissy femboy shemale + shemale romantic teen (18+)
94%
What If My Mom
Country Boys with a Difference I loved my Brother's cock, don't get me wrong, it's just what happened and our Mother loves our cocks as well as she loves our breasts. Let me explain. It all happened when I was 13 and my brother was 11. Ours was a happy family living in the hill country of Kent... Read full Story
shemale lover 2012-06-14 16,388 shemales taboo Group Sex
86%
Miko and Mali; Thailand's finest teen sisters
Last August my friends and I went on a “lads holiday” to the beautiful country of Thailand. We had booked a fortnight, which was to consist of five nights in a city hotel in Bangkok, and the remainder in a stunning 5* resort in Phuket. It was my first time in the country, my friends hav... Read full Story
shemale lover 2014-06-25 8,207 shemales taboo lesbian sex
85%
Tits and Cock
I had always wanted to fuck a shemale. The idea of a hot chick with a huge thick cock really turned me on. I called an escort service and asked for a lady with something extra. About and hour and a half later my doorbell rang. I open the door and there stood a tall curvy beauty, must have been six f... Read full Story
shemale lover 2012-03-25 4,095 anal sex Big Tits Creampie orgasm jerking off huge cock
100%
End of the Beginning Part 2
The relieved pair headed to the shower. Matthew leaned over to turn on the water. Jamie realized she would have to remove her wig or it would be ruined. Matthew looked over at her inquisitively. “It’s a wig; I have to take it off.” Jamie answered to the unspoken question. “I ... Read full Story
shemale lover 2012-04-14 2,655 anal sex Creampie oral sex
66%
A Perfect Cuckoldress Wife
My wife rose slowly, before lowering herself down his length again. Her head tipped back, she squeezed her breasts, playfully teasing her own nipples. Her eyes opened, lustfully admiring the chiseled ebony body of her lover. Balanced skillfully on her stockinged toes, she began picking up the tempo ... Read full Story
shemale lover 2012-04-30 5,130 Cumshot Creampie Fetish crossdressing
100%
Dogging tv slut
It was dark enough now I thought. It was about eight o'clock on a warm spring evening and I was ready. I had started getting ready about three hours earlier. I'd showered, cleaned all those special parts, applied my make-up heavily and dressed. I was wearing a skimpy flower print top over a black si... Read full Story
shemale lover 2012-05-22 6,227 anal sex Cumshot oral sex
100%
Black Transsexual Power Games
I give dick and my Black male bitches have to take it. No such thing as trying. You either take my dick up your ass or you don't. I smiled to myself as I thrust my ten inches of hard Black dick into the tight asshole of Richard Lucien. The big and tall young Haitian groaned as I fucked him. Well, th... Read full Story
shemale lover 2012-07-10 3,148 anal tranny Creampie Ebony oral
100%
Blushing Bride Chapter 4
Chapter Four: The Hen Party I've already told you all about the night a couple of days before my wedding, the night of my stag party, the night where I got to live out all my fantasies and play the blushing bride, dressing in my soon to be wife Gina's gorgeous white wedding dress and lingerie and... Read full Story
shemale lover 2012-07-21 3,922 big dick shemale oral sex crossdressing
100%
The High Bidder Gets Chrissie
My BFF Kelly belongs to an Alternative Lifestyles Club and her being a member always seems to affect me. Several times a year the club hosts what they refer to as a "Slave Auction". The rules behind the auction state that certain members who are selected by random draw are required to br... Read full Story
shemale lover 2012-08-15 3,805 Group Sex fuck oral
100%
Jenny, Melissa and Me
I’m watching you on the screen, Jenny, as you pull down your pretty nylon panties with the floral prints and spread your legs. Your brunette hair hangs down around your lovely eighteen year old face, smiling as your labia open wide and you begin to rub your clitoris, all the while smiling, and... Read full Story
shemale lover 2012-10-28 2,523 anal Group Sex Fetish oral
100%
Dottie's Back
Four weeks had passed since my first blowjob party. In that time, I had become obsessed with getting implants. The concept of being tit-fucked and wearing deep-cut tops without being concerned about the distinct line between my flesh and the fake boobs had become a constant fantasy of mine. After be... Read full Story
shemale lover 2012-11-02 3,852 Group Sex Cumshot facial oral sex
100%
Simon
This is a true story that I need to share and has completely change my sex life. I've been married to my loving husband for 20yrs and have been totally faithful. we have a good sex life and are both in our mid forties, both in good shape we also have a fifteen year old daughter. I like dressing sex... Read full Story
shemale lover 2012-11-19 2,950 Cumshot orgasm oral sex
100%
White Mistress & Black Male Slave
Right now, I'm staring into the eyes of my favorite person in the world, a sexy black man named Pierre D'Arnaut, as I slam my member up his tight ass. For I am a sadistic biracial transsexual with dominatrix tendencies who can't get off any other way. My name is Claudia Fils-Aime and I heartily auth... Read full Story
shemale lover 2012-11-21 5,358 Creampie domination Interracial
94%
A NIGHT WITH A TRANSEXUAL
Since my passionate weekend with a shemale and just getting my ass fucked for three days almost by a beautiful black transexual with a 13" she meat,my fantasy for tranny cock was finally fulfilled,a couple of weeks after that weekend i went to a local gay bar called Crusing 7,it`s was sunday ni... Read full Story
shemale lover 2013-06-22 5,880 suck Creampie Shemale Fucks Guy ass fucking 69
90%
SIX HOURS OF PLEASURE AT THE STUDIOS
Six Hours of Pure Heaven. Authors Notes: This is the story of my first visit to an anything goes swingers club in Las Vegas. The night of the story I was one of the first arrive and one of the last to leave. This club is a real club and it is called the THE STUDIOS and it is open 4 days a week, Thu... Read full Story
diablo598 2016-04-18 6,416 cum group сrossdresser cockold swingers club
33%
My new Experience with Amy Cute Shemale in Pune
Hi friends i am back with new story. I am mad shemale lover. and keep on finding new shemales for me. This time i got new website to search for shemale www.massagerepublic.com I saw an advertisement of Amy and i liked her. called her and fixed appointment. went to her hotel, which was ok ok ... Read full Story
Stud4Shemale 2021-02-20 6,134 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale shemale fucks man man-fucking-shemale Indian Shemale Pune
77%
A Night i will Remember 4 Ever
About six months ago I went to a transvestite bar and dance club in the centre of the city where I live. I was dressed in my sexiest all-leather shift minidress, sheer stockings and 4-inch stilettos, and my favourite blonde wig. I was fully made up with long false eyelashes and blue shadow, painted ... Read full Story
bigtranslover 2013-12-19 7,516 anal shemales Group Sex
93%
The Hot Girl at the Bar
My girlfriend and I broke up the week before, so I was pretty depressed. The guys at work decided to take me out to the bar after work to get wasted cause that’s what we do. So we all packed into the truck and headed to the bar. When we got there we were the first ones in that night so we sa... Read full Story
shemale lover 2015-10-01 10,348 anal suck Creampie
75%
Tranny and Me Meet The Milf
This past Friday morning my phone rang. It was Chandra my tranny friend who I met and fucked some weeks ago. She told me that she had nothing to do this weekend and that her roommate was out of town and she was alone. I told her that if she wanted to get out of the city that she could spend the week... Read full Story
shemale lover 2011-08-08 3,269 shemales hardcore Group Sex
100%
Bitch Maker Part 3
"Alex bring me some juice." Sammie said, rolling over in bed and hugging her pillow. "Yes mistress!" I replied, with enthusiasm. I crawled out of bed and walked down the hall, on the way past Tim's room I looked in on him. He lay there silent, his cock trapped in it's new c... Read full Story
shemale lover 2011-09-23 4,061 anal sex licking facial domination
100%
New Leila
I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most. It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before. I'd stayed over at friends and after a nic... Read full Story
shemale lover 2011-10-05 2,846 anal sex Creampie orgasm oral sex
80%
Alpha Gamma's Secret Part 3
-7- "This has been an important and exciting year for our sorority," said Jessie, House President, to the assembled sisters of the Northeastern University chapter of Alpha Gamma Tran. Today was a very special day. It was the annual Commencement Ceremony which marked a successful en... Read full Story
shemale lover 2011-11-03 3,720 transsexual orgasm ass licking
100%
Man or Mandy? Part 2
I woke in the morning snuggled into Mandy's back, my arm around her. I moved my hand up and touched her cheek, her skin was so soft. I was letting my thought wander to the events of last night. I still couldn't believe that I had enjoyed sucking a cock. Mandy started to stir, rolling onto her bac... Read full Story
shemale lover 2011-11-26 2,111 anal Creampie Big Cock
100%
TS Prostitute Urge
After college I began to explore the world. To that point I was the average male that happened to get a lot of tail. My sexual exploits with women were something I was proud of and always gave me a sense of being a real man. After years of watching straight porn and imagining myself in every possibl... Read full Story
shemale lover 2012-01-27 3,578 Group Sex sucking cum
100%
Sissy Training
This is a true story, looking back it is hard to believe it actually happened, but it did. I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We&r... Read full Story
shemale lover 2012-03-12 8,150 Group Sex Fetish bdsm
50%
She had a COCK bigger than mine ..oh my !
this is no B.S ,no fantasy, no make belief, no fairy tale,.. this is a TRUE STORY and an ACTUAL EVENT. iv always been a very observant k** growing up always trying to find the unseen and overlooked things in life i guess you can say curious....how curious ??:] well... there was this older lady... Read full Story
shemale lover 2012-03-16 46,821 sucking Big Cock ass licking swallowing
100%
The Invitation
"You see, we have to come up with something that would be so embarrassing for you that there is no way that you would ever show those pictures of me to anyone, regardless of how d***k you got, or how horny you got or how pissed off at me you were,” Sally went on. “Something that wou... Read full Story
shemale lover 2012-03-20 6,104 Group Sex crossdressing feminization
100%
Cross-dresser Drinks Cum
Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she... Read full Story
shemale lover 2012-03-29 3,248 Fetish crossdressing
70%
Trans Sexual Clinic 04
It was some six weeks since Johnny had attended the clinic with Wendy and now he found himself wanting to go there more and more. He could not get DR. Francine out of his mind, he desperately wanted to have her hard cock in him again as he fantasized about leaning forward and sucking on her delectab... Read full Story
shemale lover 2012-04-12 3,841 Group Sex Sex Toys
100%
Catching Up
It was with mixed emotions that I listened to the message on my voice mail. It was the familiar sound of Mark, a long time friend whose call I had missed earlier that afternoon. Now as I heard it, for the third time, I felt my stomach slowly relax from the uneasy twist that had taken hold the minute... Read full Story
shemale lover 2012-06-04 3,655 anal sex Creampie fingering
87%
The Intimate Dinner Party
Susan and I were filled with anticipation as we arrived at Victoria’s house. We had been invited to what the written invite referred to as a “Sexy and Intimate Dinner Party”. Victoria was renowned for her unusual, and always different, dinner and cocktail parties. She certainly ... Read full Story
shemale lover 2012-06-08 4,562 Group Sex Cumshot oral doggy style
80%
Daniel, Dani, Dana Part 2
Looking in the mirror as I drove the highway, the new me felt and I thought looked great. A new hair color with the old one the trim, my face looked smaller and even more feminine. I never had this freedom at home and hated the idea of going back there. Final exams were all that was left to shed the... Read full Story
shemale lover 2012-06-08 3,708 anal sex Cumshot Fetish crossdressing
85%
A Sissy's New Daddy Chapter 2
I hope you enjoy this second installment of 'A Sissy's New Daddy'. I worked hard on it and hope that it brings all of you the same pleasure reading it that it has brought me writing it. There are some extreme moments in this chapter but also some very tender ones. There was a line in the first piece... Read full Story
shemale lover 2012-06-16 12,798 Creampie oral sissy
80%
Bitch Maker Chapter 2
I woke up feeling pretty good. A new place and an unexpected blowjob had fallen into my lap last night. As such I regarded the maid outfit laid out on my dresser in good humor. Sam was a very silly woman after all. Yawning and stretching I stepped into the hall, hearing movement in the kitchen. I... Read full Story
shemale lover 2012-06-24 4,650 hardcore anal sex Cumshot sucking Creampie
75%
Bitch Maker Chapter 3
"Alex bring me some juice." Sammie said, rolling over in bed and hugging her pillow. "Yes mistress!" I replied, with enthusiasm. I crawled out of bed and walked down the hall, on the way past Tim's room I looked in on him. He lay there silent, his cock trapped in it's new c... Read full Story
shemale lover 2012-06-24 3,140 anal sex Cumshot jerking oral sex
100%
Double Take Chapter 2
For those who missed Part I, the players are: Sandy Lane, pro surfer with an uncanny resemblance to... Ashley Vaughn, gorgeous Hollywood starlet in a TV series produced by... Darla Palmer, who convinces Sandy to bob his nose after he is punched out by rival surfer... Buster Cruz, whose m... Read full Story
shemale lover 2012-11-03 3,863 Fetish Lingerie Sex Toys
100%
The threesome not to forget
The Avatar panel had just finished. I went to go to the bathroom, when I ran into Mae Whitman, who plays Katara. We started talking and I mentioned how I had to leave early because I had no where to stay, and she kindly offered to let me stay at her place. Later that evening, we met up outside of... Read full Story
shemale lover 2012-11-18 3,204 Group Sex sucking Fetish swallowing kissing
90%
Brian Becomes Brittney Chapter 1
My name Is Brian or at least it was the first 18 years of my life. Brittney is my new name.... All of this started when I was just out of high school. It was the beginning of the summer and I was feeling great. During the summer I was planning to do a study abroad program for a year before colle... Read full Story
shemale lover 2012-12-21 5,246 Teen (18+) Crossdresser domination Sex Toys ts
88%
Ivana Pushing Sissy's Limits
"You look ravishing," my wife Ivana said as I stood before her in a short red velvet dress with white tights and black Blahnik mary janes heels. She walked over to put a hair band in my long black hair. It was down to my shoulders now, flat-ironed straight. We stood together in front of... Read full Story
shemale lover 2013-03-19 6,692 Crossdresser Cumshot sucking Creampie ass fucking
100%
First Tranny Experience_Part 2
I had said good bye to her at her door and drove home. I got home at a decent hour and went to bed. The following day at soccer practice, I could only think about how wild a time we had together and began fantasizing about the whole affair when my cell phone went off. To my surprise, it was Kim s... Read full Story
Jon Paul 2018-08-06 4,803 Group Sex Bareback Creampie Blowjob Asian Ladyboy
60%
The Greatest Liar, Date With The Devil
The Greatest Liar, Trans Erotica With A Purpose © Alexandra Rios 2019, all rights reserved Disclaimer This is a work of fiction. All characters (including the narrator), firms, business entities, organizations, teams, products, medical providers, medicines, governments, government officials, c... Read full Story
the greatest liar 2019-08-20 4,129 Big Tits Bareback Creampie Guy Fucks Shemale
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 9,239 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
100%
OMG how I love sex
I offered this comment with a gallery and video - "She was a t-girl .. worked at the deli counter .. large breasts, intense eyes, I wanted her to fuck me .. I put on a slutty outfit (as you see) .. ordered some cheese .. she asked if I wanted to "talk" in the back when she took her break .. it was b... Read full Story
Rianna Legs 2024-01-19 5,808 milf slut tease
86%
Party with my best friend
To continue the topic of shemales fucking girls, I am publishing this awesome story of a young girl getting fucked by her high school friend! Enjoy reading! My name is Cindy, and I am 18 years old. I have blonde hair and brown eyes, and boys think I am very sexy and attractive. But the story I am... Read full Story
shemale lover 2015-06-09 5,446 Blowjob blonde cum
100%
A Shemale Vacation Part 1
I was eighteen, naïve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for m... Read full Story
shemale lover 2011-09-05 10,902 Cumshot sucking cum swallowing
50%
Twisted
"Baby, are you sure this is the place?" Eve squealed a bit too loudly, her voice both high-pitched and thick from the third Cosmopolitan. "This looks so, I don't know; fancy-shmancy for a full on mix-it-up ladyboy bar. I know, I know, this is South Beach and everything here is la-de-d... Read full Story
shemale lover 2011-10-31 4,876 shemales Big Tits fingering oral sex
50%
Man or Mandy? Part 3
We showered together, washing each other. We spent as much time kissing as watching. I was spending much of my time on her incredible tits, getting them all soaped up, and then rinsing them off. We got dressed, hopped on my Harley and roared off towards an auto parts store. As went into the mainl... Read full Story
shemale lover 2011-11-26 2,189 anal sucking Creampie ass licking
100%
Danielle's First Time
Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Danie... Read full Story
shemale lover 2012-02-03 5,514 cum dildo fingering
90%
Becoming a Sissy Slave
He gave me the choice. He had programmed me for a week and knew which way I would probably choose, but he gave me the choice. I could get out. Or I could continue. It was up to me. On my knees or out the door. It was that easy. Now I had to choose. I guess I should backtrack, first. You ... Read full Story
shemale lover 2012-03-05 16,853 hardcore deepthroating cum swallowing facefucking
71%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2012-03-16 2,851 cum oral sex swallowing
100%
Sucking hard and good
I was never one of those transvestite porn fans or MTF & drag queen sex lovers. I much prefer sinking my teeth into kinky transgender personals or simply find myself a busty tgirl to love, hold and perform the best heshe fucking ever. So that's exactly what I did last night. I went to one of ... Read full Story
shemale lover 2012-03-26 2,781 Big Tits blonde oral sex large penis