Sort by
Relevancy

Free Stories

96%
Ladyboy surprise in Bankgkok
A few years ago I went to Thailand for the first time, my first stop was the bustling city of Bangkok. I had heard stories about the nightlife, the girls and the tourists. The country had never appealed to me that much but through a twist of fate I ended up visiting the city of sin for a couple of d... Read full Story
Gracemel121 2021-03-25 11,635 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy cum in mouth
62%
First time with a ladyboy
Another little first timer's story and 5 minutes of glory for our reader Greg. I remember my fist time like it was yesterday. We met at a bar the most beautiful woman i have ever seen. A the end of the night she asked me for a ride home so natrally I gave Her one. She looked so hot in her tigh... Read full Story
shemale lover 2015-05-05 8,691 anal Blowjob dick
100%
Thai Ladyboy goddes in Tokyo and a cheap love hotel
This is a real account of my meeting last week with a beautiful Thai ladyboy working at a flashy show at a night club in Tokyo. Written as a not to her. Hope you like it. You sexy ladyboy goddess, I must say you have the most beautiful body. When we first started drinking wine and talking ... Read full Story
lblover77 2012-10-09 9,625 anal Ladyboy oral
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 8,479 Asian Ladyboy Shemale and Girl
63%
Thai ladyboy Jenifer
Another wonderful story posted by our reader Jason... I have experience with Thai ladyboys and Phillipino lady boys. The one Thai ladyboy that left the most impression on me is Jenifer. She is a bit big on size for a ladyboy, but her gentle demeanour sure make all for her size. The first time ... Read full Story
shemale lover 2015-04-09 5,825 anal tranny dick
96%
True story about a ladyboy first timer fucking her customer's as
Those of You that dream about having a beautiful Asian ladyboy fuck your ass will certainly love this naughty story posted by our reader Tommy where he got his asshole violated by a cute ladyboy. Did I mention that she was a first timer and Tommy was her first customer? Hi, me again with anothe... Read full Story
shemale lover 2015-03-05 10,267 anal cum Asian
90%
Ladyboy Fuck Show
Thai Kathoey Ladyboy Fuck Show in Patpong So last night my TG girlfriend and I went to Bangkok's Patpong prostitutions zone to see a fuck show. Instead of the "normal" sex show with old women shooting darts out of their twats, we asked the touts to take us to a ladyboy fucking show. ... Read full Story
shemale lover 2015-05-21 7,416 anal Asian dick
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 8,364 anal Blowjob Asian
78%
Hot Ladyboy
I had a phone number for a hot ladyboy that my friend insisted that I call for something different. I had always admired them but I had never been with one before. I finally decided to call the number a few nights ago and a soft feminine voice answered. The hot ladyboy was named Hollie and she to... Read full Story
shemale lover 2015-09-29 5,715 anal sucking nipples
80%
First time sex with a ladyboy
Ok guys, this is a milestone in my life. I had sex with a ladyboy!!! It was completely amazing, something i have fantasized about for years but never thought i would do! I met her on the internet a while ago and have been chatting to her since. We got on pretty well and she invited me for dinner!... Read full Story
shemale lover 2015-10-19 10,060 Blowjob shemale jerking off
100%
Smoking ladyboy in latex indulges my fantasies
Our reader, Matt J, have recently visited Pattaya and, as you can see from his story, it was a very fruitful visit! He had a petite ladyboy Lo spend a night with him during which he came countless times, and now he says he'll be coming back for more. Who wouldn't? ;) I recently indulged a few of ... Read full Story
shemale lover 2015-03-01 7,477 sucking Asian Ladyboy
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 7,455 asshole Fetish Ladyboy
50%
Anal Pleasure
Hi, I am nick i'm 21 and I lovee trannies. I have been jerking off to shemales for quite some time now, at least a couple years and I always get really turned on thinking about fucking them. However, for some time now I've been feeling a little curious of how it would feel like to get fuck... Read full Story
nick tamer 2018-03-02 5,231 Teen (18+) Sex Toys sissyboy hypno Anal training trainining
92%
Well endowed ladyboy Yoko
Here's the second part of the story posted by our reader Tommy, and i'll tell you what, it's even hotter than the first one! I went back to Casanova some months later, hoping to see that well endowed ladyboy. She was dancing on stage - we made eye contact, she hopped down straightaway and we kiss... Read full Story
shemale lover 2015-05-01 6,358 anal cum Asian
70%
His first anal!
Andrew was a very simple guy. He was not aggressive, very quiet and nice. Actually he was not quarrelsome, just a man of peace. But we all know that still waters run deep. Over the past few years, Andrew had longed for being penetrated. Vehemently. He needed to be bent over something and fucked thor... Read full Story
shemale lover 2014-05-09 8,675 anal shemale jerking off
100%
Bi male and anal sex
Thru out my adult sex life I have always enjoyed having my ass teased and played with. Then I started dating a woman whom loved to tease a mans ass with her fingers, yes fingers where she quickly got me use to taking 2 of her fingers. Then one night things changed. After a hot night of wild sex,... Read full Story
shemale lover 2012-10-10 5,193 anal sex cum jerking fingering
78%
Anal Therapy
My new psychiatrist wasn't at all what I expected. When I saw her name in the phone book, I pictured a dowdy old lady wearing a long, gray skirt and flat-soled shoes. What else could Dr. Edith Doss look like? I got my answer when a tall, leggy redhead stepped into the waiting room. A tight, black... Read full Story
shemale lover 2012-11-24 7,559 anal Fetish cum crossdressing
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 5,760 anal Cumshot Ladyboy oral
100%
Bangkok Night with Thai Ladyboy Dancer
I was visiting Thailand back in the 90s and was blown away by the “Potpourri” of sites, sounds, and smells (not all of them good) of this city. Beautiful women were at every corner and very friendly to foreigners. I went out with a group of guys on the town after dark to check out the go-go bar scen... Read full Story
AllenB 2022-04-20 5,579 Shemale Fucks Guy Asian Guy Fucks Shemale rimming bottom ladyboys cum in mouth top Versatile
100%
Lola Chapter 2
Lola Chapter 2: A couple? It wasn't as if we were together. We had jerked off together once, and of course we slept in separate rooms, but I slept restlessly that night. Dreamed something scary that I couldn't remember in the morning. I didn't have work scheduled that day so I took it easy. When ... Read full Story
BellaBeau 2023-10-05 5,197 anal Cumshot Creampie Guy Fucks Shemale Homemade latina Tgirl
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 3,730 anal Fetish oral
100%
Cheating Sissy Wife chapter2
My sweetheart Keith is back from his road trip and we were about to make up for lost time. He didn’t even want me to fix dinner. Instead he said that we would order pizza later. Meanwhile we started making out right there on the couch. We were both horny and anxious to get next to each other. I felt... Read full Story
Regina10 2020-10-26 4,597 Crossdresser Big Tits Cumshot Bareback Creampie Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth
86%
Ladyboy orgy in Thailand
During one of my many nights in the sleaze capital of the world Pattaya, Thailand I was at a certain ladyboy bar all dressed up in my sexiest outfit that the "girls" had ask me to wear in as I had shown them some pics of me dressed. Not that I could ever hope to compete with any of them! ... Read full Story
bigtranslover 2014-01-05 13,621 shemales gay male Group Sex
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 4,125 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
86%
9 ladyboys gangbang me and force me to suck their cocks in my fa
Our forum member, Dutchboi, had this fantasy of being dominated, sissified and humiliated by nine Asian ladyboys, with Mint and Nancy being two of them. For some of You this story may sound too cruel, others will find it really hot. My fantasy is to be at a ladyboy's apartment and fall alseep aft... Read full Story
shemale lover 2015-03-03 10,580 anal Blowjob Asian
100%
Delectable Debbie
I can't explain why it was that I fancied having sex with a transsexual. I mean I'm a perfectly normal happily married man, couple of kids, mid-40s, a stone or so overweight but reasonable looking, my own hair and teeth and everything. I must admit, I've been with one or two...escorts, hookers, what... Read full Story
shemale lover 2012-08-10 3,783 tranny anal sex orgasm oral sex
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 2,180 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
94%
Ladyboy Surprise - Part 2
My jaw hit the floor. Between the legs of these to beautiful girls were 6 inch cocks! I was stunned. Here I am standing naked in a shower with a raging hard on with what I thought were two gorgeous women, and they turn out to have dicks! I didn't know whether to shit or go blind! One of the ladyboys... Read full Story
shemale lover 2015-10-15 10,299 shemale cum oral
73%
Free Shemale Dating Site The Place Where I Want To Spend My Life
Browsing through all payed porn services left my wallet thin, so I went for free shemale dating site option. When my boss noticed that I was paying less attention to work and more attention to Shemales, he fired me without any notice. I was hit hard with the economic crisis - the bank sell my hou... Read full Story
shemale lover 2016-08-26 5,315 sucking pissing Ladyboy
57%
It doesn't get any better than this!
15 years ago, I went into my older brother's room to grab a porno mag. He had stacks of them all over the place. I wasn't too choosy. I picked the magazine off of the top of the pile that was closest to his bed and went into the bathroom. My usual routine was to open the mag, find a babe, pull out m... Read full Story
shemale lover 2012-05-17 3,299 shemales Fetish jerking off tgirls
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 32,817 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
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 6,050 anal hardcore erotic encounters fantastic
100%
Crissie Fucks the Neighbor
It was a Saturday afternoon and I was all alone in the apartment as my roommate Kelly had gone home to visit her mother for the weekend. I hadn't had a date or been more importantly been laid in several weeks. Needless to say I was very horny. I quickly flipped through the TV channels and as usual... Read full Story
shemale lover 2012-06-07 3,816 anal sex Creampie oral sex facefucking
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 5,420 Cumshot suck Ladyboy Guy Fucks Shemale Interracial swallowing
100%
A Big Celebration that goes sides for me
I'm reading my book when she enters. I hear a clatter of keys and I look up, to see framed in our little entry way the tall figure of my roommate. She's standing there as in triumph, legs planted apart, her face all smiles. I smile too. Geena never looks this happy, I've never seen this side of her.... Read full Story
ASSEaster5678 2018-09-14 3,629 Ladyboy party Surprise
100%
Catching up with the biggest cock
I have recently written with an account from my diary about the biggest cock that I’ve ever seen and someone saw the experience and wanted to know more as I had said that I met him a few times. So, I can bring that right up to date now because I have recently been to see him again. But let me go bac... Read full Story
lkusex 2021-06-03 10,543 Masturbation Big Cock Ladyboy domination self sucking Ass to Mouth Vintage
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 2,730 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
100%
TG Girlfriend moves in
Monday morning 6:00 am and I am just awakening, and I realize a naked body beside me has her arm around me, we are both naked. My wife Lydia is out of town to a seminar, and this adorable brunette perky tits and lovely eyebrows, beautiful lips slightly pink, sleeping beside me. Joanne and I had spen... Read full Story
Jon Paul 2022-01-18 4,964 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth
87%
My ts fuck
Patong beach thailand a few years ago, a few drinhs at a bar with some friends on going to toilet at public loo which was next door to ladyboy bar. Standing and relieving myself in runs two lovely ladyboys from next door. Who proceed to do there make up and have a good look at my cock for good measu... Read full Story
shemale lover 2012-06-15 4,872 anal sex Cumshot Ladyboy rimming
92%
Thank you for Paradise
This hot shemale story was sent to me by our forum member Leeya and i'm anxious to share it here with everybody. It's a classy story about a guy who went to an Asian country on a business trip and met a very beautiful womain in a very romantic atmosphere... Little did he know that this young voluptu... Read full Story
shemale lover 2015-03-13 6,262 anal Asian Ladyboy
50%
Learning how to deep throat Part 2
Looking up at me from her kneeling position she said 'you aren't to let me choke my self on your cock, but you get the idea.' She stood up, I knelt down, she reminded 'make a fist with your thumb inside and squeeze tight, you will be able to take my cock in you mouth and possible your throat. I f... Read full Story
shemale lover 2012-02-24 2,562 sucking Creampie Ladyboy
43%
Thinking about shecock
This Ode to shecock was posted at our forum by a great guy Ila. It pretty much sums up the feelings of all ladyboy lovers and I can't think of better words to express love for shemale cock, he already brought it to perfection. ;) I think about having a shecock in me just as often as I think about... Read full Story
shemale lover 2015-04-23 4,679 anal fingering sperm
90%
A Good Fit
I didn’t want to be there. Trying on clothes in a department store doesn’t rate high on my list of entertaining activities but I needed a few more sport coats so I bit the bullet and went to the upscale store at the mall. At least I had the freedom to go on a Monday afternoon when there ... Read full Story
shemale lover 2012-04-10 3,945 anal sex Group Sex facefucking
50%
The club
"Okay ladies," Missy said to her guests, "relax and get ready because I have a very special treat for today's meeting!" "What is it?" and excited Jayne asked while removing her sweat shirt and jeans. "Now you know better than to than that" Missy replied with a... Read full Story
shemale lover 2012-05-03 4,387 Group Sex Cumshot Ladyboy fingering Sex Toys
100%
Joe gets to the bottom of things
She kept it tucked away, uncomfortable, squeezed between her legs held in place by the tight rubbery panties that really weren't her style, but they punctuated the "surprise". Joe was aroused by her femininity, as she slipped off the spaghetti straps of her little white dress revealing the... Read full Story
keeponst 2012-10-08 2,788 sucking Ladyboy virgin
85%
True story, TS 3-way
This is a true story. It was a typical night in Pattaya Thailand and I'm still recovering from the 25 hour flight from Tennessee to Bangkok that I flew just days before. After a few days in BKK, I arrange for a hotel car to me to Pattaya, a seedy explosion of lights, blaring music and drunken ... Read full Story
Thailover 2014-03-11 9,580 Cumshot threesome jerking ass fucking facial stroking
100%
Vegas Honeymoon to Remember
I had dated my wife (Carmen) for about 6 months before we decided to Marry. One evening we were soaking in the Jacuzzi together and drinking wine. She always wants to try different things, which makes our sex life wonderful. Carmen asked me if I ever had any fantasies. I said I guess like most me... Read full Story
Jon Paul 2018-05-30 20,218 Group Sex Cumshot Bareback threesome Ladyboy Shemale and Girl
87%
Chicago TG Romance (part 2)
As you must read part one of this story, one of the most interesting and attractive T-girls I have met is sleeping beside me in my motel room after a wonderful evening of being together. Beth awakened around 4am and got up to go to the bathroom. She was brushing her teeth and heard me stirring, I di... Read full Story
Jon Paul 2018-06-04 5,787 Amateur Shemale Fucks Guy Blowjob Asian Ladyboy Ass to Mouth cum in mouth
77%
My Mom the Whore
Since junior high I love the way women clothes look and feel. Sometimes after school I would wear my mom panties and bras I didn't think nothing odd that all my mom underwear where a bit sexy and revealing, but I was a dumb kid who started his life in cross-dressing. Not into several years ... Read full Story
paulinacock 2019-07-17 10,449 Crossdresser Amateur Fetish transformation transsexual Ladyboy tgirl femdom crossdressing transgender feminization tg sexy Tranvestite girly MtF FEMINIZED transgirl sissified womanhood janegirl emasculation tgcaptions emasculate demasculinize
100%
TG Neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-04-22 6,328 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale
100%
Santa Likes Shemales Femboys
Did you know Santa Clause is real....and he likes shemales femboys??!I It happened last Christmas Eve. I fell asleep watching the snow fall just outside my window. I was comfy under my layers of warm blankets I clutched tightly, in the black lace panties and red lingerie night dress or nighty I wear... Read full Story
Chrissy Tunnell 2022-12-01 3,488 Small Tits Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
Curious_billy 2023-05-07 7,065 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade cum in mouth
100%
How My Wife Became a Swinger
Hello, my name is Jackson, Jack for short, and I'd like to tell you about my wife and I and how we became swingers. I've changed the names of people and places to preserve privacy. Just so you know this does involve male on male sex and inter course with a transsexual. So let me begin. For the fi... Read full Story
Loveto 2011-10-12 8,388 anal bisexual gay strap-on
66%
Showing Off For My Wife's Pleasure
There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my f... Read full Story
shemale lover 2011-10-25 5,269 anal asshole shemale
50%
Freak House Superstar Come Fest
Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... Read full Story
shemale lover 2012-02-01 6,156 anal shemales Group Sex
100%
Being a shemale's toy can be fun
Joliet called and asked if I would be interested in having some fun...I thought about the last time and how pissed off she got. I hesitated long enough for Joliet to whimper in the phone 'I promise to make up for my last theatrics, no bondage and I will reward you very handsomely if you attend to my... Read full Story
shemale lover 2012-02-10 3,742 anal sex Ladyboy facial