Sort by
Relevancy

Free Stories

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 8,423 anal Blowjob Asian
0%
Looking-Glass Ladyboy
I was taking a walk to stay--all right; I'll admit it--to get in shape, when I saw the "Going Out of Business" sign in the second-hand furniture store a block north of my condo. I wasn't in the market for anything, new or used, but I can't resist a bargain, and what was better for finding ... Read full Story
shemale lover 2011-10-29 7,525 asshole Fetish Ladyboy
100%
Bi Pantyhose Passion
I've had a Pantyhose Fetish for over 30 years now, and love wearing them on a daily basis. But back in the summer of 1995, I suffered a heat stroke, and almost died, when I recovered, I vowed I would stop fantasizing, and live out these dreams and fantasies. I had been masturbating while dress... Read full Story
shemale lover 2012-06-04 4,036 first time Cumshot Masturbation Fetish Blowjob pantyhose
80%
intimate Cousins
My favorite cousin and first lover, Billy, was just released from prison and I was anxious to see him. I am ecstatic that he is out, and I am thinking about all the past fun we had as I prepare to revisit those good times. Tommy knows all about my relationship with Billy and he understands my need t... Read full Story
Regina10 2022-05-13 5,912 Stockings Crossdresser Cumshot Masturbation Bareback Blowjob Big Cock Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth double anal
75%
Soo, my ladyboy friend in Bangkok
This shemale story is not your usual one as it's written by a lesbian girl Jamie and it involves a very sensual description of sex with an Asian ladyboy. Enjoy reading! Well as an openly gay Lesbian woman (submissive as I say) a long way indeed. My friend in Bangkok, Soo is a beautiful, articula... Read full Story
shemale lover 2015-02-01 8,539 Asian Ladyboy Shemale and Girl
66%
Ladyboy dominatrix
If you read my other stories you know I'm intersexed and I was a ladyboy prostitute when I was um, very young. I don't condone such activities. They were sick perverts who used me. True I got a lot of money and expensive gifts but that doesn't make it right. They should all be castrated. Th... Read full Story
shemale lover 2012-10-15 9,784 Fetish Asian domination sissy rimjob
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 2,614 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
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 9,132 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
62%
Crossdressed Lana - Hannover, Germany
Crossdressed Lana - Hannover, Germany Very Sexy & Compliant Sub-Slut Is Searching For Kinky BDSM Live-Dates At Hannover, Germany!!! I Am Bisexual And Want Men, Woman, Couples And Trans For Outdoor, Swingerclub, Porncinema And Public Sex. I Love To Wear Very Hot & Sexy Clothes Like Lingerie, Stoc... Read full Story
Crossdressed Lana 2020-02-06 4,166 Stockings Crossdresser Group Sex Outdoor Bareback Fetish Blowjob gangbang Lingerie domination Latex Sex Toys double anal
100%
Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
Regina10 2020-11-23 4,889 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
100%
Double Take Chapter 3
Sandy and Ashley switched off the television and stared at one another in disbelief. Normally, they didn't stay up to watch the network telecast of Wet Girls, which came on at 10:00 on the west coast. After all, they had to get up at 5:00 the next morning. But they knew the entire country would be t... Read full Story
shemale lover 2012-11-03 3,047 Stockings Fetish feminization
100%
I wanna fuck almost everyday
I can't stop thinking to be Double penetrated for two men at the same time.... It makes me feel I'm insatiable gurl... Two Big cocks mmmmmmm after been fucked for so long ... I will never go back... And certainly I will totally satisfied and addicted to it...... Read full Story
Bellasohot 2022-07-13 3,715 Crossdresser Amateur Latina Bareback threesome Big Cock Ladyboy Lingerie Guy Fucks Shemale Mature Ass to Mouth double anal
100%
Couple and a Tranny
There is a saying that a single man looking for companionship and good fortune will seek someone for marriage. Lydia and I met several months ago on an online dating site. We agreed to meet at a bar restaurant for drinks and initial meeting. She was at the bar wearing a yellow sundress, white painte... Read full Story
Jon Paul 2022-09-20 5,184 Cumshot Outdoor Latina Bareback threesome Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth double anal
57%
Nicks Shemale Experience
Nick had discovered he had a thing for shemales 4 months ago after stumbling across some pictures on the Internet of a really hot ladyboy from a porn link site. This sort of thing had never turned nick on before but looking at pictures of the small-breasted brunette really made his dick hard. It did... Read full Story
shemale lover 2011-08-22 3,800 anal Fetish oral
50%
OTAGE DU CHANGEMENT
3 ans de bonheur conjugal. Cela après être sorti pendant 3 ans. Je savais que j'aurais pu faire bien pire. Nous étions heureux ensemble et l'entreprise que nous menions en partenariat avait pris d'assaut. Nous nous étions rencontrés au départ à l'école de design, nous avions sympathisé à la fois dan... Read full Story
Femboy 2021 2023-01-20 883 Stockings Crossdresser Amateur Fetish Big Cock Lingerie domination cum in mouth double anal
100%
Regina’s Double threat.
Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... Read full Story
Regina10 2022-02-08 2,960 Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock redhead Guy Fucks Shemale Ass to Mouth double anal
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,156 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
100%
The Three of Us
Imagine you are a lonely person on the inside, and just wanting all your life to be loved for who you are. Holli Artigas, was just that person. Wondering whether her obsession with Jon Silva, a football star, was from a casual encounter, or was she truly fond of him? Growing up in the Sao Paulo, ... Read full Story
Jon Paul 2024-04-28 2,307 anal Creampie Shemale Fucks Guy threesome Shemale and Girl cum in mouth double anal shemale fucks female
83%
The Making of A Sissy Part 12
Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as... Read full Story
shemale lover 2012-05-31 4,268 anal Fetish little cock sissy
75%
The Developing of Emma Part 6
As the weeks went by, Emma was subjected to many rituals before a crowd of masked leering males. Each day she was kept caged and plugged; her dosage of pills never forgotten. Each day Emma felt more and more feminine; one morning Elaine had her stripped naked except for cage and plug, and led her be... Read full Story
shemale lover 2012-08-27 2,373 anal Fetish sissy
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 5,825 anal Cumshot Ladyboy oral
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 8,956 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
85%
Whores and Pimps - Part I
Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... Read full Story
shemale lover 2012-05-13 7,899 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
100%
My story, more or less pt.3
Earlier on, when I was scouring through various drawers and closets for feminine clothes in my home I have stumbled upon two old skipping ropes. "A fun time" I thought to myself, not giving them another look and continuing with my search. Little did I know they would become the backbone of my "sessi... Read full Story
Thigh_High_Boi 2023-01-06 3,535 Stockings Masturbation Fetish Ladyboy Lingerie Homemade pov
76%
Nylon teasers
They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... Read full Story
shemale lover 2012-01-30 9,798 Stockings Big Tits fucking foot fetish
100%
Fixing The Car
I had been cross dressing since I was about 10 years old, I'm now in my thirties and this story is about my first encounter with another man. It all started one day when my wife would be out for the day and I had settled down to surf the net looking for transgender sites, I was only dressed in a bla... Read full Story
shemale lover 2012-11-08 3,957 first time Fetish crossdressing sucking off
37%
First time Crossdressing
I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards that allow members profiles and posting messages. I also post to local groups in my area that allows one to post messages to a small geographical area or to a distant user g... Read full Story
shemale lover 2013-07-17 6,011 first time Crossdresser Fetish Mature bisexual
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 11,237 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
50%
The Greatest Lie Part 15
I think that if you could get honest answers, a lot of heterosexual guys would probably admit to having had at least a passing desire to be a girl. If they were honest, they would probably admit they thought of it "when I first noticed a girl's breasts" or "when I first felt a girl or... Read full Story
shemale lover 2012-01-20 6,095 anal hardcore erotic encounters fantastic
100%
Hose and Heels in the Bedroom
Liza giggled as she sat back down on the sofa, a mischeivous smile on her face. "Whats so funny I asked?" wondering what had tickled her fancy. After all the only thing that had happened was that she'd just been to the toilet to relieve the pressure that the 3 or 4 glasses of wine tha... Read full Story
shemale lover 2012-05-15 3,835 anal sex Cumshot Fetish fingering pantyhose heels
100%
Caught and Used
I am a secret, heterosexual panty boy, that loves to dress up in my wife's lingerie when she is not around. My wife and I have two mutual friends named Mike and Mandy. Mike and Mandy had things stored in our garage while they moved. Well my wife had to go away for a day seminar for her company, and ... Read full Story
shemale lover 2012-06-09 5,331 anal shemale Lingerie crossdressing
100%
Karen, My School Teacher Part 3
Regret... Hmm Maybe Not. By FoxyHosed My excuse for a cock got hard again. My horniness got the better off me. I went to lock the front door. I took my shoes, pants and sweater off. I stood in the hallway only in pantyhose and t-shirt. ‘Don't do this. Walk away from this now. But you go to boa... Read full Story
FoxyHosed 2021-02-05 8,400 Crossdresser Cumshot Fetish Blowjob pantyhose pantyhose anal crossdresser guy fucks crossdresser
100%
Dressed for Disaster
After a last look at himself in the full-length mirror on the closet door, Pat put his magnetic key in his purse and left his hotel room. He had done this enough times to be almost calm as he waited for the elevator. When the door opened, he was relieved to be greeted by an empty lift. It always ... Read full Story
shemale lover 2012-11-21 3,002 Fetish pantyhose makeup
80%
Me and 2 black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider my self a crossdresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine ladyboy. I have been taking also hormones for 4 years, on and off and I already saw many changes&he... Read full Story
shemale lover 2013-06-22 5,488 Cumshot suck Ladyboy Guy Fucks Shemale Interracial swallowing
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 4,203 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
91%
Stepdaughters Pleasure Daddy
As I was showering, I was thinking about Anna coming. What would I say to her? How would I act? I felt very uncomfortable and I was getting extremely nervous. I finished washing, then shaved. As I was getting dressed, Dawn came in. "I know your hungry, Daddy, but let's go out for breakfast.&... Read full Story
shemale lover 2011-12-05 7,570 anal licking Creampie
80%
Michele And The Predator
The predator peered through the bedroom window and smiled; he couldn't believe his luck. This woman was just to his taste; he felt himself begin to stiffen as his eyes devoured her; he couldn't wait until he had his hands on her. In his mind he played out the scenario that he envisaged would soon ta... Read full Story
shemale lover 2012-05-13 4,316 Fetish transvestite fiction
75%
A Couple And A Shemale Encounter
Not long ago I was sitting home alone on a Friday night with nothing much to do and feeling horny so I decided to go out. I showered, misted myself with my favorite perfume, put on a sexy black bra, rolled on a silky new pair of jet black sheer to waist pantyhose, slipped into a tight, very short, l... Read full Story
shemale lover 2011-08-26 5,093 anal Creampie shemale
100%
Hose and Heels in School - I'm a bad girl
A knock on the door? Who could that be? After all it was mid-evening on a Friday night and I certainly wasn't expecting anyone. I was looking forward to a night of relaxing on the sofa and nothing more. I opened the door and there stood Liza, staring at me with a smile on her face. "U... Read full Story
shemale lover 2012-05-11 3,052 anal sex fingering spanking crossdressing
77%
Discovered
3:00pm... The workday was done. I'd been eagerly waiting for this time. On lunch I pulled our 'toy' chest (actually a footlocker) out of the closet for easy access that evening. Months before, I told my wife, Kaitlyn, that sometime she's going to come home and find Nicole bound to the bed just wa... Read full Story
shemale lover 2012-09-27 4,647 Fetish pantyhose crossdressing
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 4,888 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
50%
LA CRÉATION DE MONICA ⚧️ ⚧️
Je savais. En regardant en arrière maintenant, je me rends compte que j'ai toujours su. Je n'ai jamais rien fait à ce sujet, jusqu'à ce que je sois prêt mentalement, émotionnellement et physiquement. Je suis né Matthew J. Smith au milieu des années 70 en Amérique centrale aux États-Unis. J'ai grandi... Read full Story
Femboy 2021 2023-03-30 831 Stockings anal sex Masturbation Fetish Blowjob Big Cock Lingerie Sex Toys feminization cum in mouth poule mouillé poule mouillée et fille poule mouillée poule mouillée
100%
First Time Being a Woman
My heels clicked on the concrete path as I made my way toward the secluded toilet block in the southern parklands. Tonight would be my first experience being with a man whilst I would be dressed as a woman. I had been dressing now for some time and had fantasised about what it would be like. I didn'... Read full Story
shemale lover 2012-10-08 4,568 first time Creampie Fetish crossdressing
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 6,376 anal Crossdresser Blowjob heels cum in mouth pink dress
100%
The Mole
Police work is a paramilitary occupation. Uniforms, rank, weapons, discipline…It can be exciting and interesting for some and boring for others. Some officers seem to find lots of action during their career (or maybe it finds them) while others never use their sidearm except for target practi... Read full Story
shemale lover 2012-01-26 6,399 brunette Crossdresser Fetish
100%
David to Dee Chapter 2
His nipples had grown considerably over the last two months. Gina had been putting those little nipple suckers on him twice a day. Dave wouldn't be going to the gym anymore. Well, it had been a long time since he'd gone to the gym, anyway. Since Gina had had him shave his entire body, last spring... Read full Story
shemale lover 2012-07-30 5,674 anal sex Cumshot oral sex rimjob
100%
Betrayed Chapter 8
Did I happen to mention everything was moving so fast? People weren't really surprised Lance Layton took his commission and ran for the door as fast as he could. There wasn't an employee in the firm who didn't wish they could produce the same results for themselves. The rumors ran rampant: he had pu... Read full Story
shemale lover 2012-05-30 3,651 pussy Fetish crossdressing
100%
Sissie Slut's Windows of Womanhood
I flash back to my first time with a grownup adult at the tender age of16 . I was so nervous now that we were here in the motel room. I was nervous for so many reasons. I lied to my family and told them I was staying at a friend’s house. Instead, I'm here with Mr. Joey in a motel room and he was my... Read full Story
Regina10 2021-02-22 6,529 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,368 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
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 4,890 anal Crossdresser Blowjob kissing transgender virgin romantic earrings
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 4,503 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
87%
TO BE OR NOT TO BE – PART 1
TO BE OR NOT TO BE – PART 1 by Spanky de Bautumn This is a story about how taking a play to New York City changed people's lives. A transgender coming of age story. I was born Harold Stanley Dayes, not a great name for a kid growing up. I know my parents loved me, but Harold was my mom's dad a... Read full Story
SpankydeBautumn 2021-02-22 3,722 Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob Ladyboy Lingerie Shemale and Girl cum in mouth
90%
Young Crossdress, Meets His Daddy
Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very ... Read full Story
shemale lover 2012-08-17 4,476 anal Crossdresser Cumshot Fetish oral domination
50%
AGENCE D'ÉLEVAGE FUTANARI partie 2
« Suspendu ? Comment ça, je suis suspendu ? » dit Alina. "Je n'ai pas vraiment le choix. Zut, je pense que je suis gentil de ne pas vous dénoncer à la police. Vous l'avez mise enceinte pour l'amour de Dieu", a déclaré le principal Pulcher. "Mais je n'ai jamais été s... Read full Story
Femboy 2021 2023-02-13 858 Crossdresser Fetish Blowjob Shemale and Girl domination Futanari
100%
A Natural Sissy Part 4
The Next Day I was up early, and called to set up a surgery for Stacy’s breast enhancement. The hormones were working but his tits seemed to have stopped growing at a B cup. I wanted him really top heavy. At least a D cup, maybe a DD. I let the exhausted sissy sleep. As I was finishing u... Read full Story
shemale lover 2012-03-24 3,817 Stockings Fetish cum oral sex sissy
100%
美娇酱幻想系列一
正常的青壮年男子，三天左右就可以排出高浓度的大量浊精，大部分人选择插入女人的毛穴肉洞达到排精，而我雌雄同体人妖享受肛门被插入高潮同时排精，双重享受，女人化妆，涂指甲是为了取悦男人，我浓妆艳抹，红艳艳的脚趾甲让男人流口水，而我比女人更浪，更知道怎么让男人舒服，男人喜欢玩妖艳女人，雪白的玉脚让他吸吮。淫荡的艳舞后舔弄骚臭的阳具，卵蛋，屁眼，龟头冠状沟系带用舌头敲击，舌尖挑弄，马眼流出汁水就吸吮干净，不时用舌尖顶马眼，双手拨弄男人的奶头，爽的上天。 我疯狂的变装持续了11年，从最初的偷母亲奶罩内裤穿身上自慰，到如今……听着嗨曲扭动，甩着没毛的小鸡巴，扭曲红色脚趾，戴着铁链，脚链手铐口枷一次次的灌肠... Read full Story
Bluesyangiip 2019-05-06 890 Crossdresser Fetish Blowjob Asian Ladyboy Guy Fucks Shemale