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My Erotic Free Shemale Porn Movies Sex Scene In The Air
My job as an airline stewardess always keeps me on the move. The fact that I am a shemale limits me to hanging out with a certain group whenever I go to certain cities. Well, one particular night flight, there was a handsome man that pinched me on my ass as I walked by. Normally, I would complain... Read full Story
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A real cd explains what cd on cd sex is like
A lot of "strait" guys love shemale porn.I was one of them.Pre-internet I discovered shemale porn but it was hard to find.I had girlfriends but the sex was never great.like many i was more concerned with cumming to soon than actually enjoying myself.Plus,as a porn watcher my fav was anal.M... Read full Story
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My way to shemale sex
It all started with porn. 10 years ago, i was watching porn on my bed, jerking off watching a girl sucking a big cock. I looked at my cock and started wondering what that beautiful peace of meat tasted like. After a few moments of hesitation, my curiosity took over and i put my back against the wall... Read full Story
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From Gloryhole Peegasm to Shemale
I was in a porn video booth. I young guy stepped into the next one. I was already jerking my small dick, but he didn't even pull his pants down. He asked me if I wanted my dick sucked. Actually I think he said something like, "hey, let me suck your dick." Recently I had let some weird, ... Read full Story
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My Kinky She Male Porn Pictures
I never thought that I would enjoy making shemale porn pictures,but here I am and I must say it's been a crazy ride.I met Mike one night in a bar, and that's how my journey started.Mike was a very sexy and he was a real charmer. When he approached me he didn't know my secret,and I didn't want to ... Read full Story
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The Greatest Liar, Deal With The Devil
The Greatest Liar, Trans Erotica With a Purpose By Alexandra Rios, © 2019 The Lost Chapter, Deal With The Devil This is a work of fiction. All characters (including the narrator), products, places, events and incidents are either the products of the author’s imagination or used in a fictit... Read full Story
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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
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How i changed?!
I had been with my girlfriend for 4 years, after a drunken night i later ended up in a gay club. I came across a lad that went to my school who was always openly gay and he was shocked to see me in here. I just explained that I had only come in for a few drinks as most of the other places were start... Read full Story
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Amanda and Me Chapter 2
I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... Read full Story
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Amanda and Me
I walked in the door of my one bedroom apartment and headed straight for the computer. Lately it seemed like I had the same boring routine everyday: get up early, work all day at my stressful IT job, go straight to the computer when I get home to look at porn and masterbate, then eat dinner and go t... Read full Story
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The Zodiac Coins: Libra
2400 YEARS AGO... He was a humble shepherd. It was night and the flocks were sleeping. As he gazed at the stars, he saw a shooting star. He knew it was a portent of some kind, but was not mystic enough to know what. A little while later he saw another shooting star and guessed that wha... Read full Story
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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
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My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
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My TS Journey
I'm a straight, married guy in my 30's, at least that how I appear to everyone that knows me. I have an intense obsession with Trans women that I have been indulging since I was a teenager. Over the years this fixation has grown into something that ranged from watching porn initially, to having my a... Read full Story
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Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
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A new girl around!
You know, things, I’m gonna tell you about started when I was a teen. I was like every teen guy, I loved web porn, looked at porn on the internet, surfing porn sites through the web space and masturbated a lot. I loved and now love to watch lesbian porn: it was so hot watching girls having sex... Read full Story
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The new girl in town
It all started when i was a teenager. I was like every teenage boy, i looked at porn on the internet and masturbated a lot. i love to watch lesbian porn it was sooo hot watching to girl have sex. i soon after that i got into the anal sex, watching the girl have orgasm after orgasm while she has a hu... Read full Story
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My Dream Cums True
Me and my girlfriend would always talk for hours about our secrets and feelings and as the night would progress we would get into more sexual subjects but this night would change our lives forever..... ''so what's a sexy secret you have that no one else knows about?'' I asked my girlfriend. ''... Read full Story
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First Time With a Shemale
I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we... Read full Story
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A true first time.
I want to preface this reiterating that this is a real story about my first ever experience with a shemale. It's a memory I will hold forever as it was everything I could have hoped for and, as I may share in the future, lead to other experiences, too. A little history of before the first meet ac... Read full Story
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Rebound
My story is nothing new, like most girls who used to be boys I knew from an early age that I was different to all my school friends. My dad was a thug of a man, who enjoyed the physical battle of the rugby pitch as much as the post match booze up, but I took after the mother who died giving birth to... Read full Story
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Home Alone With Shemale
I sat alone at my kitchen table. I drank a cup of coffee, smoked a cigarette. I was wondering what to do with my day and then my cellphone rang. It was my girl friend Carla. She asked if it would be okay to stop by, with her new boyfriend. I sensed something in her voice, but I didn’t know ... Read full Story
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A Slut Awakens
The day began like any other; I woke up, showered, wrapped my towel around myself and sat down to begin applying my makeup. I stared at myself shocked at the transformations I had undergone the past few weeks, my beautiful feminine body so smooth and curvy it could put even the most finely molded ho... Read full Story
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Alessia Travestita Hung Mature Blonde British Porn Star
Alessia Travestita Hung Mature Blonde British Porn Star If you like Transexuals, big cocks, bondage, domination, deep throat, fisting, spit roast, 69, ass fucking, cum swallowing and big loads this story is for you. If not don’t bother reading. If you like my story please leave comments and ... Read full Story
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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
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Realization vs. Reality
So…here I sit. 40 years old and revisiting the confusion of my youth. I am, and always have been, a first string heterosexual male. From my earliest memories of when I began to notice girls, I have always delighted in the wonders of women. I became sexually active at age 16, and there has nev... Read full Story
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Seduced Willingly
Finally, I moved to a city that was exciting, Miami. I moved to Miami looking for something new and adventurous. I grew up in very conservative town where nothing exciting went on. In Miami I found different languages, gay people, different ethnic persons, art, and culture. However, my job keeps me ... Read full Story
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A Dirty Job
It had been three months since I started working at computech. It was by no means the best job in the world but I was pretty hard up and really needed the money. I could certainly never have been considered a model employee though, I had a habit of being late in the morning and often if I was ha... Read full Story
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A very hot encounter
I've had been feeling way too horny for days; masturbating every night to shemale porn. I've always loved transexuals. There's nothing better than a very hot body with a fairly large cock to be sucked and drained of hot cum. There's something even kinkier for me about a top shemale. I imagine that c... Read full Story
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Seduced Willingly Part 1
Finally, I moved to a city that was exciting, Miami. I moved to Miami looking for something new and adventurous. I grew up in very conservative town where nothing exciting went on. In Miami I found different languages, gay people, different ethnic persons, art, and culture. However, my job keeps me ... Read full Story
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My first shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe t... Read full Story
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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
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Jo, Shemale Goddess! Part 2
Jo chuckled as the man in the sharp business suit looked hastily away when she looked up and caught him staring at her legs, again. Her 'Rupaul' legs as men with a history of watching men dressed as women called them, or her 'Naomi' legs as the newer ones to the scene seemed to think. Both divas had... Read full Story
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Hung Shemale has Motorcycle Trouble near Vegas
I drive down a deserted two- lane highway outside of Las Vegas, Nevada. It is August and the temperature is well over 100 degrees. In the distance, I see a tall beautiful mature creature that walks alongside the road. As I pull over, I am stunned by her powerful physique. She sports an incredibly ti... Read full Story
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Regina's Vagina dreams
I think I wanted to be a female from birth. I once looked through a girlie magazine out of curiosity. I had impossible dreams and I longed to trade genitalia with them. I have always fantasized about my Vagina when I was younger. It was during those times that I would drift into my own private world... Read full Story
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My first shemale
This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when... Read full Story
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First time anal for young man
Over the past few years, Danny had desired the need to be penetrated. To be bent over and thoroughly shafted. He didn't consider himself gay, but still felt the need for some anal action. He first discovered his longings whilst he was masturbating. One day, out of curiosity he placed a finger in his... Read full Story
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Amy's Surprise 2: Enter Karissa
What did you think? Amy asked. Well, let's see, I started to answer, You gave me the best blowjob I've ever gotten, sucking your dick was about the best thing ever, and sharing your cum with you was incredible.all in all, I'd say it went well. Amy smiled and walked over to sit with me on the couc... Read full Story
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Fixing her computer
I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon. I showed up at the appointed time and was surprised when I s... Read full Story
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My first Shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe that started my intere... Read full Story
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First Time With Shemale
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
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Big Bot, Sex Hot, Breeder Manbabe Gets Laid
Tyler was really glad to find a new job, after being unemployed for a couple of months, but disappointed that he had to work with two macho, homophobic guys. Trouble was, the only work he could get was in a factory and the office he shared with the two guys was way out in the sheds, away from the ma... Read full Story
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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
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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
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The Wonderful Adventures of Miss K
Miss K sat near her bedroom window in her pink silk robe, staring off into the late morning skyline in the distance while she held a cup of hot chocolate in one hand and ran the other through her waist length bleached blonde permed hair. The indirect sunlight lent the dark chocolate skin on her sili... Read full Story
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Gali's Surprise Package
Chapter One Gali sat in the front row of John's class with her legs crossed, raising her skirt and revealing her garter. She had sat there since the start of a new school year, and it was her seat for the rest of the year. She'd taken Beginning English Literature from him last year, and she was a... Read full Story
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Real Experience: Having Sex With A Shemale On 24th
On 24 Aug 2012 (Friday) about 3pm, I messaged a shemale who has posted her brief introduction in one of the product and services directories. I asked whether she was keen on meeting me for crossdressing and other services. I was thinking of having sex then. She welcomed it and quoted her rate as $15... Read full Story
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Once wasn't enough!- my 2nd shemale exp
So after my first experience I got really into the porn I bought movies magezines got on websites just couldn't get enough. But watching it wasn't enough I had the real thing once and wanted it again. It had been almost a year now and only one person knew about what I had done that one fat... Read full Story
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HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
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Sweet Encore
I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... Read full Story
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A Shemale Vacation Part 3
At the French border, it was discovered that we had no passports. We were taken from the train and into a room for questioning. All four of us, Josh, Olly, Harry and myself, were terrified. Sure, we'd been in a sticky situation before on this trip, sticky particularly for me rather than the others, ... Read full Story
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Shemale Autofellatio Adventure
Hi, my name is Jessica. I'm a 19 year old Caucasian girl with a 6" surprise between my legs. Most of my friends don't know about me but I've got a few who do and one likes to fuck just as much as I do. I was bored one day browsing porn on my computer when I came across a video of a guy sucki... Read full Story
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Emily and Steve Part 1
As I pulled my cock out of Emily's ass and shot my load onto her flat stomach, where my cum mixed with the load the beautiful blonde cross-dresser had just shot from her throbbing cock a moment before, I thought to myself that work was suddenly going to be a lot more fun. My name is Steve and I w... Read full Story
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Francine Hung Red Head Part 2
This is the second part of the story of "Francine" a Transgender woman from California. She and Jonathan meet in a Tucson resort two weeks after their first weekend together. Note from Francine-Thank you Mrstanley for writing and submitting my story. In real life I live and work in Cali... Read full Story
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Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
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A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
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April Fools!!
I'm Jimmy James and I've been hanging out with the same six guys since we started college. We're a pretty close knit bunch and have stayed in touch since then. At 25, I'm the only one of the seven of us still not married. Even though we all still get together for parties and get togethers, for t... Read full Story
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Trying It On For Size
I was twenty minutes early for my one o'clock appointment so I found a shady spot in the parking lot of the upscale chain motel, kept the engine running to power the air-conditioner on the warm Sunday afternoon, took a few deep breaths and tried to relax. My mind wondered back over the series of eve... Read full Story
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First Cock Came From Old Friend
It was Saturday and I had nothing to do so I decided to go for a drive. I got into my car and headed out of the city in no particular direction. After driving for a while I realized I was close to Jim's house. We have been great friends for years but have not seen each other for a long time. I decid... Read full Story
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Bisexual Black Man's Paradise
The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... Read full Story
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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
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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
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She never saw it coming
When I was 19/20 I used to frequent LGBT bars roughly twice every month. Most nights not much would happen but I found myself going to the trans nights more often. Until I eventually had some experience with trans girls. It was mostly fairly soft fun. Me getting oral and occasionally topping th... Read full Story
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His Ultimate Fantasy
Jeff and I had been back together for a little over 5 years when I had decided to give him his ultimate fantasy. To everyone who meets him, Jeff is the all American boy. He is the quintessential small town boy. He always has impeccable manners, says his "ma'am's" and "thank you's"... Read full Story
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Why you should never cam
* Sorry for the poor writing but since it is the summer and I am taking sometime off to reflect before starting school next year I thought I would write up about what had happened to me the summer before. It is currently a work in progress and if spot any spelling mistakes or errors feel free to cor... Read full Story
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They Were Right
They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... Read full Story
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Fulfilling fantasies
What seems like a long time ago in my early teenage years, I found myself being somewhat addicted to watching porn. Every opportunity I got I was at the computer watching porn of all different flavours, and for a while I found myself really enjoying lesbian porn. So one day as I was watching a video... Read full Story
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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
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Duel With the Devil, Chapter 20 of The Greatest Liar
Duel With The Devil This is a work of fiction. All characters (including the narrator), celebrities, places, residences, neighborhoods, restaurants, legal agreements and proceedings, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any r... Read full Story
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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
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A man & Two Hung Shemales meet in Art Gallery o
I spent a week of absolute extreme erotic ecstasy with Stan. I used his throat and ass multiple times a day. He also fucked and fisted my ass as well. It is a week of total decadence debauchery and depravity. In the late afternoon, Stan and I decide to visit a local art exhibit so we can get out ... Read full Story
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Becoming a Chrissy - Chapter 2
I had always felt like I had a hot body for a girl. I was naturally blonde and smooth; I guess I had been blessed by my parents’ Scandinavian genetics. My pubes were always just a small fuzz—easy to shave and keep a clean bikini line. Same thing with my armpit hair. And my ass? Completely smooth and... Read full Story
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Just One of Those Days
Let me start by introducing myself. My name is Amanda, though I sometimes use the shortened version Mandy. I am thirty-three but my sexual awakening didn't really occur until I had turned thirty. Previously I had been a generally shy and quiet girl with a steady and normal relationship. ... Read full Story
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A Strong Man at Work
In life, some people seem to get pleasure out of pissing others off. I think you know what I mean. We've all been there. The first time I laid eyes upon Joan, I thought she was a low-class, boring and obnoxious person. Where I come from, people like that are pretty common. Who am I? Stefan. A tall a... Read full Story
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Black Transsexual Submission
My name is Theodore Morrison Guillot and I'm a six-foot-three, broad-shouldered and strongly built, good-looking black man living in the west side of the town of Brockton, Massachusetts. I am happily married to a lovely black woman named Hera Jackson Guillot. She's fine as hell. Standing exactly six... Read full Story
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My First Time
I used to be a normal straight guy, or at least, so I thought. That was until I began exploring trans porn, I was so turned on by it, but thought it was wrong, I tried to fight it, but soon enough trans porn became the only porn I could get off to. I didn't know what to do with this obsession, ... Read full Story
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Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
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My Descent
This is the first time I've told my story publicly. I wrote this maybe 3 years ago, and have shared it with one person. I used to cross dress in my hotel room while away on business trips. I'm a fat bald 46 year-old who looks ridiculous dressed up in ladies underwear. When you're obsessed, tho... Read full Story
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Just One of Those Days Part 2
Hello again. My name is Amanda, though sometimes I use the shortened version Mandy, when the mood suits me. I'm 33 and have stayed single for three years, since I discovered that Richard, my boyfriend, was not only cheating on me with dozens of women, some my so called friends but was al... Read full Story
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How did i get here?
I’m a thin, pretty good looking 30 years old guy, living with the girl of his dreams. But a girl without a cock is no longer enough now. All my life I considered myself as a straight guy, even if sometimes duchbags at school called me a fag. I only dated girls, prefered long love stories over on... Read full Story
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