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4 years ago
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Magical Ring Turned Me Sexy Shemale

Hi, guys, this is Rii and you can find me on Facebook by searching Rii Femboi. Now coming to the sex story. I am 28 boy and an absolute nerd, always studying and as a result had no friends since my school days. I thought things would change in the college, but I was wrong that time too. After completing my college I got a very good and a high paying job, but there too nobody wanted to befriend me. I had to move away from my parents to Delhi for a critical project that my company entrusted me...

Lesbian
4 years ago
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My First Experience With A Shemale 8211 Part 1

I was on my knees with my hands holding her butt. The smell of her orifice is something that is still fresh in my nose, even after hours. I inserted my tongue between her butt cheeks. I could feel the hair around her orifice on my lips and my tongue. It tasted a little sour, a little tangy. But what aroused me was the feeling of her asshole, it’s wrinkled border on my tongue and the hair around it. My mouth was open wide and my tongue incessant. After a little while, her hole started to give in...

Gay Male
4 years ago
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Shemale Park Shame

Park Shemale Shame Hi All, Now I’m as straight as the next man, I’ve got a cute little blonde girl with a great arse who I love to ride, lick and tit feel, but, well, here’s a cautionary tale. This is a warning for you fellas who sometimes find yourselves looking at pictures of pretty shemales, in all their frillies, on the internet when you just wanna have that added pervy kick so as to cum. Right, the other day I was walking home from the pub after a couple of after work drinks with...

3 years ago
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First Time Surprise Shemale

I'm an eternal masturbator. I've always like wanking and playing with myself. At a young age I worked out that I likes playing with my ass hole, sticking things in it, walking round all day with something in it. With the advent of the internet I was like a pig in shit. So much porn to be had and so many things to see and do. One day I discovered the true beauty of the shemale. Wow. Gorgeous women, with cocks. Prior to this it had been women with strapons that got my attention, but this?...

2 years ago
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Sisterhhood of Female Supremacy

SISTERHOOD OF FEMALE SUPREMACYPROLOGUEAs is my custom I awakened at least an hour before my Mistress, Goddess Samantha had instructed me to awaken her.  I checked my entire body in as many places as I could to be sure there wasn’t a single hair so as to comply fully with my Goddess’ instructions.  Even my legs were smooth as silk, something I have never experienced before. I was to wake her up promptly at nine and have her bath ready with her desired water temperature of 105 degrees. I...

4 years ago
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Real event OMG shemale and another surprise

This is a true event, a lil back history, for about 3 yrs ive become fascinated by shemales, no porn will do without a shemale cock, i dont see myself as gay but i do wonder that if i like penis there must be some gay in me, but i do not like men at all. Now regular porn just does not do it for me and i alway fantasize about a shemale cock, a big juicy shemale cock and what i would do if i had the chance, i envy every man i see in the videos that get to suck and get fucked by shemales.cut the...

3 years ago
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Fucking A Hot Shemale In Bush

Hi guys this is Avinash from Chennai.. I am 21 yrs old and this happened few years ago to me in a local train in Chennai. This story is about how i fucked a shemale and got robbed by her. Now to tell about me i am a fit guy with muscles shaped up.. My cock size is 13cm ( yes u read correctly.. My cock is 5 inches.. I cant lie that its 10 inch huge monster and all.. Now coming to story i used to go to my school by local train in Chennai.. From Guindy to Chrompet.. We all know beggars will get in...

1 year ago
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TGirl Japan

The list of Asian stereotypes includes a predilection for tourist photography, really bad driving, and eternally youthful appearance that makes MILFs look like teens. They also make fun of Asian dick sizes and the way Asian dudes can’t really grow mustaches. That latter trait actually helps them make for passable trannies, as you’ll see on TGirlJapan.TGirlJapan.com is an Asian tranny site from the tgirl porn purveyors at Grooby Girls. If you spend any time at all beating off to shemale pornos,...

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3 years ago
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How I Ended Up a Submissive Shemale Slut Part 1

I am sitting here in my studio apartment, and I am alone and depressed and looking for guidance from a very dominant woman who wants a very submissive shemale slut that is 30 years old, horny as hell, and shares the same likes and tastes that I do. Mainly f***ed blowjobs, and lots of different outfits, everything from leather, latex, lingerie, you name it. Let me go back 5 years ago to how it all started for me. We all have our own stories and beginnings, and this one is mine. I am a very...

1 year ago
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How I Ended Up a Submissive Shemale Slut Part 1

I am sitting here in my studio apartment, and I am alone and depressed and looking for guidance from a very dominant woman who wants a very submissive shemale slut that is 30 years old, horny as hell, and shares the same likes and tastes that I do. Mainly forced blowjobs, and lots of different outfits, everything from leather, latex, lingerie, you name it. Let me go back 5 years ago to how it all started for me. We all have our own stories and beginnings, and this one is mine. I am a very...

1 year ago
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The orgy with a shemale

THE SPELLING IS OFF SORRY I WAS AT WORK! I had to move to Japan back in the fall of 2004 and lived in Tokyo in a 3 room apartment.I could not pay all of the rent so I lived with a female school teacher age 27 years of age and japanese.Her name was Miki.There was a one more girl who was friends with Miki ,I never seen much of her.Her name was chichi and I don't know what her job was but these two woman were not japanese women miki was around 5 feet tall and was around 108 pounds ,Long black hair...

She Males
4 years ago
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Buffy the Shemale Vampire Slayer Part XI

Buffy the Shemale Vampire Slayer, Part XI By Cal Y. Pygia Darkness had fallen upon the demon world. In the intermittent flashes of lightning that resulted from Willow's weather spell, the landscape was illuminated, and the horrible phallus-plants were revealed, writhing and thrashing. The cock-stalks within Buffy's mouth, cunt, and ass, and the hollow tubular stems attached to her nipples and cock also squirmed and wriggled. She shuddered at the feel of the thick, serpentine...

1 year ago
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Jimmy Olsen Shemale Bimbo Chapters 12 to 13

Jimmy Olsen - Shemale Bimbo by Mistress Tawny Suede Chapter 12 - Frustration! Thursday morning. Jimmy woke up and stretched. He rolled over and sat on the edge of the bed. He momentarily lost his balance a bit. Despite weeks of having tits, they still threw off his centre of balance a bit. And his back hurt. But he smiled when he realized that was because his boobs had gotten much larger since his initial transmogrification. He giggled as he took his breasts in his hands and...

3 years ago
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Shemale Funpark

You go to a Funpark in Miami, Florida where you are supposed to meet your Friends. You really like them and drove all the way out here just for them. Right as you enter the Funpark to get to the meeting point, your Friends call you in a groupchat. They tell you that their Car broke down a long time ago but their Phones had no Battery and they were in the middle of nowhere. They could only call you now to tell you that they sadly can’t come to the Funpark. They say that you have to go on the...

Transsexual
3 years ago
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My First Shemale

Early May 2006 or 7, standing on the northeast corner of 46th and 3rd, a rather nice New York City day, except Belinda wasn’t answering her phone for our 3 pm “appointment”, and I was not keen to just hang around smoking cigarettes on the corner wondering if I had been stood up. I had no prior experience but it dawned on me shemales, especially shemales for hire, might not be the most dependable group of people, well, maybe if they were a shemale cop, that thought hit the erogenous spot of my...

1 year ago
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NewTransNudes

Do you enjoy New Trans Nudes? I’m talking about beautiful women with their tits out and dicks bigger than your own, the kind of babes who are truly packing and well endowed. Trans porno is way more common than it's ever been, and it seems like every free tube has some chicks with dicks tucked away in the corner. Well, if you’re a big fan of the women and their penises, it’s usually a better bet to jack off to a site that focuses on them. That’s why you’re here, right?Just like it says on the...

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1 year ago
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SpicyTranny

Looking for some cocks at Spicy Tranny? Are you tired of beating off to the same old scenes of huge cocks slamming into tight pussies again and again and again? Want to mix it up with a little something different? How about adding dicks to the hot chicks? If that sounds like it might do the trick, you might be interested in what they’re peddling over at Spicy Tranny.Look, if you’re having second thoughts about the whole shemale thing, you’ve got nothing to worry about. SpicyTranny’s collection...

Shemale Porn Sites
3 years ago
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Strong fuck from my shemale lover

Last summer I was visiting Kolkata and after a hard day’s work I needed some alcohol to relieve tensions.I ended up going over to the night club at the same hotel where I was staying. Entered the bar late on a weekday and found that there were very few people there. I sat down and asked for some whiskey. Whiskey always seem to help get me fucked up and that’s all I wanted to be right now. Too much seem to be on my mind as I stared off into space. I had only downed two shots. The bartender asked...

Lesbian
4 years ago
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first time with a shemale

Anyone who has read my other stories will know that they are based on real events, this one is also based on an actual event. It happened on a recent trip to Thailand.We arrived in Thailand on a Friday morning, looking forward to a well-earned break. Jaq and I worked long hours, and we lived for our holidays. We had decided to visit Thailand as we were both curious about the availability of good looking shemales.It had long been a fantasy of ours to try a threesome with a shemale and hoped this...

Trans
4 years ago
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My first Shemale a true love story

Even from a pretty young age, I loved Shemales. I loved everything about them. They seemed to me to be the perfect object of sexual desire. Beautiful, feminine, tits and a cock. My first introduction happen by accident, in a way. On the other side of town was a row of newspaper stands that sold adult newspapers. Late one night, I rode my bike to them and with a pocket full of quarters, bought every one. When I got home, i couldnt wait to look at them and in the darkness of my bedroom, saw my...

4 years ago
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My first time with a shemale

OK, I was wasting my time on shamble videos and pictures on the web for about 8 years! When I first entered a porn site I almost got sick, but soon I got really curious about it but didn't dare to click that button; couldn't explain why I wanted it so much though. Eventually I pressed it. I started with shambles alone, then shambles fucking girls, then shambles fucking shemales and end up with shemales fucking guys... I started loving it, watching it on a daily basis. My fetish for thong...

4 years ago
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My first encounter with a shemale

I am a straight guy who had never strayed before.. however i had been having urges over shemales and started wanking to shemale porn every now an again online. i have always been interested with my ass being explored but i never found men attractive. with shemales it was different. they are beautiful, slender but also filthy at the same time. it seemed perfecti had planned a europe tour some years ago and my first stop was amsterdam. after a few hours of roaming the red light district i was...

3 years ago
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MY FIRST SHEMALE ENCOUNTER

I remember the first time I found myself in bed with a shemale. I had just broken up with my girlfriend. I was lonely, I was horny, andI had zero intention of finding myself in another relationship with a woman. When I told my buddy, Bob, he told me he knew just where to take me to solve this. So he took me to this club over in West Hollywood. The place was FULL of gorgeous women. My head was swimming - they were almost all slender and dressed in very sexy attire. Short skirts and sheer nylons...

2 years ago
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me my daughter and a shemale

my last story was with my daughter for the first time now we both have shemale girlfreind very beautiful ones they would come over me and my daughter would put on our sexy heels she picks my shoes now lol and they would fuck us both on the same bed theses shemales are in good shape they would fuck me and my daughters tight lil asses and shoot globs of cum then they would watch us creampie it out one of them came over one night when i got off work my daughter wanted me to tougue out her shemales...

1 year ago
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My First Shemale Encounter

I remember the first time I found myself in bed with a shemale. I had just broken up with my girlfriend. I was lonely, I was horny, and I had zero intention of finding myself in another relationship with a woman. When I told my buddy, Bob, he told me he knew just where to take me to solve this. So he took me to this club over in West Hollywood. The place was FULL of gorgeous women. My head was swimming - they were almost all slender and dressed in very sexy attire. Short skirts and sheer nylons...

She Males
2 years ago
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ABOUT FEMALE DOMINATION

So what is Female Domination? The entire term seems to be a contradiction to our male dominated society. Female Domination (or FemDom as some refer to it) did not originate from dominant women or feminists. It was men who coined the phrase Female Domination to categorize their sexual and social desires to submit themselves to the female gender. So is Female Domination merely a sexual fantasy that some men harbor or is it a reflection of a societal evolution? Based on my years of study,...

1 year ago
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TrannyVideosXXX

Tranny Videos XXX! Is it gay to jack off to tranny porno videos? Are you a huge homosexual if you get wood watching a hot girl stroke her own wood? Would you be considered a fag if you spent all morning touching yourself to TrannyVideosXXX? I guess these are age-old questions probably better suited for a social scientist than a Porn Dude, so I’ll just focus on the easier question: does masturbating to shemale movies get you off? Well, it does if you pick the right tranny...

Shemale Porn Sites
4 years ago
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A night with two shemales

I’m an oil geologist and spend considerable time traveling to the Gulf of Mexico. . I stand 5' 10" wet, have wavy brown hair with already early bits of gray, (which runs in my family). Good genes have also blessed me with keeping the fat off. With moderate exercise I match up well against guys who power exercise once a day. My face has been described as triangular and my eyes are blue with bits of gray. I'm said to have a good personality and women always tell me they feel comfortable around...

Trans
2 years ago
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MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous during a flight, so I needed a drink to calm my nerves. I sat at the bar and ordered my meal and drink. After a few drinks were gone, I noticed this stunningly beautiful lady enter the bar. She sat a few...

2 years ago
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MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous during a flight, so I needed a drink to calm my nerves. I sat at the bar and ordered my meal and drink. After a few drinks were gone, I noticed this stunningly beautiful lady enter the bar. She sat a few...

1 year ago
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TGirls xxx

Tgirls.xxx aka shemale.xxx! There are plenty of great tranny sites out there, but there are also those that fall way short. But when it comes to the hottest premium shemale porn, there is every reason for you to choose Tgirls.xxx. I wasn’t sure of what I was getting myself into the first time I saw the site, but once I landed on the tour page, I realized that Tgirls.xxx is part of the Grooby Production network that specializes in hot transsexual porn and exclusive content. Now, anyone familiar...

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1 year ago
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Futanari

Is Futanari smut just shemale porn with a different name? I know that’s a loaded question, because the weebs might blow up my DMs with thousand-word technical explanations about the differences between Japanese and Western culture and their attitudes towards sexuality. I’m only really asking in a rhetorical sense, because I think it’s a really good way to introduce this next site. If there really is a difference between the two dick-slanging chick genres, this is probably the place to find...

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4 years ago
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Her perverted mother and the shemales

The next day, Jess was busy at work and texted me to ask if I would mind doing her a favour. She wanted me to go around to her sister’s house to pick up some of Ellie’s textbooks. I agreed I would, partly because I was intrigued to meet Ellie’s mother, imagining a mature version of the beautiful student whose mouth had made me come the previous day, crossed with the elegant dirtiness of Jess.I had also heard from Jess the real reason why Ellie was staying with her during her exams. Officially,...

4 years ago
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The Studio and the Shemale

When the company I worked decided to relocate to the north of England, it was made clear to me that there would not be a job for me there and so the decision whether to move woth or leave was decided for me. The redundancypayment was extremely generous, as it should be, I had been with them since I left school. So now I had to find a new job and the decision was whether to stay in the line I was in or change careers, but With the redundancy payment as it was there was no rush.Quite by chance I...

2 years ago
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Shemale in bus with a nice girl

Hi dosto maree 3rd story ap ka leya bohat acha repons raha ap ki taraf sa specially females ka respons to bohat he zayada tha, such bataon to mujha itnee achee feed back ki umeed nahi thee, mai shemale haoin is waqt maree age 30 thee or khoob bara boobs jo 38 ka tha or land ka size be 6″ sa kuch bara tha, Maree nazar aik female par thee jo job kartee thee mai rozana usa dakhtee thee or imagin kartee thee, vo public taransport mai atee jatee thee, aik din maina socha ka is ka sath bus main...

Lesbian
2 years ago
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London Mein Indian Shemale Se Fuck Hua

Hi dosto, mera naam Azim hai. Meri age 23 hai aur main ek bisexual mard hun. Mujhe sex ka bohut craze hai chahe aurat ke sath ya aadmi ke sath. . Aur yeh meri pehli story ek shemale ke sath hai jo kuch saalon pehle ki hai. Agar aap logon ko meri gay stories aur maid ke sath stories pasand hai toh zaroor yeh story bhi aap logon ko bohut pasand aaye gi. Yeh kahani 2 saal pehle ki hai jab main London mein padhai kar raha tha. Meri age uss waqt 21 thi aur yeh meri birthday ke kuch dinon baad ki...

1 year ago
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Grooby Girls

GroobyGirls aka Shemale Yum! Sometimes I get a real hankering for a nice, nasty fuck with a blonde hottie with huge tits and a nice ass. I want that little slut to suck my dick clean, let me put it in her pooper, and then give me another dirty oral cleansing. I bet you have similar fantasies, but in yours the bitch also has a huge cock. I ain’t the type of guy to judge you, fruitcake, and in fact I’ll point you to a classic of the transsexual paysite genre: GroobyGirls.Before rebranding as...

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4 years ago
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A Shemale Fantasy and my wife Part 4

A few hours later I was woken up by Carol. "Wake up baby this day is just getting started" she said. My eyes opened and I was like a kid on Christmas morning. I couldn't wait to see and "feel" what she had in store for me next. Carol instructed me to shower get dressed and leave the house for a few hours. My next surprise needed some set up. I did ask she told me. Before I left Carol came up to me grabbed my dick, kissed me and said "get ready for some fun". Having no...

4 years ago
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A Shemale Fantasy and my wife Part 4

Introduction: The Conclusion Basking in the glow of what just happened, I put my head back and just passed out from total bliss. I didnt know what else Carol had in store, but I knew I wanted to be well rested. A few hours later I was woken up by Carol. Wake up baby this day is just getting started she said. My eyes opened and I was like a kid on Christmas morning. I couldnt wait to see and feel what she had in store for me next. Carol instructed me to shower get dressed and leave the house...

2 years ago
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Shemale Stewardess Seduction

Please note that this story is not written by me! It was stored in my computer for a long time now and decided to share it with you. The author's name as well as the site I found the story are not known... My introduction into the sultry, steamy world of shemales came (and I mean came!) at 35,000 feet, on a plane flight to the Northwest. I had been working myself to the bone, staying until ten or eleven at night, coming back in at six o'clock in the morning, and I guess the stress...

3 years ago
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Beautiful Shemale Sex Fantasy 8211 Part 1

Hello people, Leviathan here with my first story. To describe me, I am an average looking guy with a pint of femme body and many have said I have a great ass. Jumping into the story, this is purely a work of fiction. I request you all forgive me for grammatical and spelling errors. I made up a story by mixing a few of my fantasies and pint of my imagination, and a lot of horniness! It was around 8 pm. I set off for a 16-hour long journey to native, my train just arrived. After a fuss, I managed...

Gay Male
1 year ago
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Femout

Fresh faces and unsoiled cunts are major draws in the world of pornography. Everybody wants to see schoolgirls, ripe teens, virgins, and first-timers earn their wings on camera. The age of 18 is the beginning of a new life for a lot of girls, but it’s a different milestone that marks the newly minted broads at FemOut.In case you hadn’t guessed from the name, FemOut.xxx is a tranny porn site dedicated to tgirls early in their transitions. These are sluts who just crossed the threshold into...

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3 years ago
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A Shemale Vacation

A Shemale Vacation - Part One by Richard-to-Rachel I was eighteen, na?ve 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 me, wild sex was something I wasn't exactly familiar with. I was still a virgin and I was pretty determined that that...

2 years ago
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Fucked by shemale

I've always thought myself as a straight guy. However, I always fantasised about serving a big cock. The problem was that I didn't fancy guys. That is when I came across shemale porn, OMG, what could be better?! A hot ass girl with a huge cock. Unfortunately, convincing shemales that aren't escorts are hard to come by, if not impossible. I started scouring escort sites and found a local shemale offering her services. She was Latino, 5"10, big tits, and best of all, and 8inch cock. I was really...

4 years ago
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Fucked by shemale

I've always thought myself as a straight guy. However, I always fantasised about serving a big cock. The problem was that I didn't fancy guys. That is when I came across shemale porn, OMG, what could be better?! A hot ass girl with a huge cock. Unfortunately, convincing shemales that aren't escorts are hard to come by, if not impossible. I started scouring escort sites and found a local shemale offering her services. She was Latino, 5"10, big tits, and best of all, and 8inch cock. I was really...

3 years ago
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First time hooking up with a shemale

Well the first time I hooked up with a shemale was an escort visit (night out, massage and the rest :)), this was when I just started to gain interest in shemales (about 2 years ago), so I became curious and wanted to know what it was like to spend a night with one, after all they say its having the best of both worlds. I looked up a Brazilian shemale online and when I saw the pictures, I couldn't resist a visit. I mean her femininity was beyond this world, stunning from head to toe. I gave the...

2 years ago
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Shemale And A South Indian Girl In An Abandoned Temple

Hey readers, this is my 4th story here in ISS. I am a fair-skinned bisexual male. I usually write erotica partially based on things that happen in real life. Let’s jump into my story. This is a story of a shy South Indian girl with a pretty face, fair skin, big natural Indian boobs, and a juicy bubbly ass. She meets a natural Indian pretty shemale to realize her wildest dreams come true! So the story is being narrated in the South Indian girl’s point of view. Her name is Lavanya or Lavi for...

3 years ago
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SHEMALE SURPRISE 3

i have just fulfilled one of my fantasies with the help of niki, who used tobe nicolas a male cousin of mine who is now living life as a shemale. i havejust swallowed a river of cum after sucking on my very first cock. being malei have never thought of myself as being gay, and i still don't as i am not attractive to males at all. i love being hetero, but i do have an attraction for crossers or shemales. my cousin niki and i were having our first tryst and after making niki cumin my mouth she...

2 years ago
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One man s shemale adventures part 2

I had gone round to Kami’s as we had planned a dinner date, but she was nowhere to be seen. Amy let me in, having just returned from the gym. “Yeah, she said sorry but she’ll be a few more minutes.” Amy said, and I couldn’t help but eye her up and down in her sexy gym gear as I followed her into Kami’s bedroom. “While you wait, why don’t you suck on my clit?” she said, as she pulled down her lycra shorts and spread in front of me on the bed. Underneath, her white panties were soaked through...

1 year ago
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Trans500

We are heading back to the wonderful world of chicks with dicks at Trans 500. That’s right, tranny, transsexual, shemale, traps, whatever it’s called these days. Does it even fucking matter? They’re chicks, they have dicks, and they are fucking, getting fucked, and doing every kinky act in-between. So, don’t be fucking shy if you love this shit. Some of the hottest porn out there has shemales in it. And talk about variety. These sluts will do anything. Anal, blowbangs, BDSM, and so much more....

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4 years ago
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My first time with a shemale

This is a true story, probably the wildest thing that ever happened to me. It happened when I was about 19 years old and lived in Hamburg, Germany. At the time I was one of those willowy, thin guys, little body hair and a healthy appetite for sex but not much experience yet. At a young age I discovered how exciting it is when I fondled and fingered my ass while masturbating and I developed a real fascination with anal sex.At the time I used to visit a club ("disco" in those days) somewhere...

2 years ago
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Buffy the Shemale Vampire Slayer Part XII

Buffy the Shemale Vampire Slayer, Part XII By Cal Y. Pygia "Let's get this over with," Buffy suggested. "The sooner we start, the sooner I kick your demon ass." Baphomet smiled. "You will fuck the witch," he said, "while I fuck you." Buffy shook her head. "Willow's my best friend. I can't--" "Then you have lost before we've begun." "Buffy, it's okay," Willow said. The Slayer looked at her. "Will, we've been friends since high school." The redheaded witch smiled....

2 years ago
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Sinuosa Planet of Female Aliens

The following is the document I received, relating the story of a previous document that its author in turn received… Scrawled notes from my late colleague Blackwood were all I had to guide me. They existed only in a tattered leather-bound volume, chronicling in his own hand the final journey and his descent into sheer madness. A pity that he should have passed away in the behavioral health unit on his return to Earth without my having any opportunity to interrogate him regarding his...

3 years ago
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Overdose of shemale cock

I had been at college for almost three weeks when the events I am writing about took place. My name is Karl. I’ve always considered myself a pretty normal guy. I played football in high school, dated a cheerleader, and usually got decent grades in my classes. Alright, enough about me… let me tell you how my freshman year started. I was sitting in one of the hang out areas on campus one evening, trying to figure out which of my new teachers would be least upset were I to turn in a...

2 years ago
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My First Time with a Shemale

I had watched porn for a long time, graduating from straight porn to videos of shemales, falling in love with TS stars such as Leilani, Julie Bond, and the gorgeous hermaphrodite Dane Harlowe. However, as much as I fantasized about being with a shemale or cross-dresser, I never thought it would happen.Then one night when I was living in Indianapolis, after being out drinking and dancing, I stopped at the local adult video store. I had parked near a white van and, as I was drinking some more of...

2 years ago
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Sex Survey Females Firsts 2

I inquired in my first Sex Survey for 'females firsts' in terms of erotic experiences.I inquire in this second Sex Survey for 'females firsts' in term of loveliest loving ever.I long to read your most memorable moments and favourite fancies to get off again.I long for memories like mine which never fails to excite me, nor my blonde beauty!I love to read all answers to my first Sex Survey, a double dozen cunning confessions and still coming.I love to share my most memorable experience with my...

3 years ago
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Enjoying A Cleaning Lady 8217 s Shemale Dick

Hello everyone, my name is Ajay Kumar, and have a story of dick. I am based in Visakhapatnam. A little introduction about me. I became bi-sexual under different circumstances. I was later diagnosed with erectile dysfunction. That made me more drawn towards the bisexual world. The following story is a work of fiction. The story dates back to the time I lived in Hyderabad for my training. I stayed in a PG as I’m too lazy to cook or look after myself. I just came back to my room after finishing...

Gay Male
4 years ago
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Shemale Subway Sex

I was out at a dance club with some friends on Saturday night. Clubbing isn’t really my scene though, and I soon found myself very bored. Looking at my watch, I saw that it was almost 1 o’clock in the morning. I was having an awful time, and if I didn’t leave then, I would miss the last subway train and have to take a $50 cab ride home. So I said goodbye to my friends, and caught the very last train home. The subway ride from the club was going to be around 40 minutes. At first, the car was...

3 years ago
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One of my shemale escapades from back in the day

A number of years later, after my first shemale expereince, I still had a penchant for a hot shemale or a slender sissyboy who was passable. That's when I met Gina, who fit the mold of a slender sissyboy who was much more than passable, she was gorgeous.The first time we got together was on a rainy Sunday afternoon. My wife was out of town and I was cruising aroind on AOL in the SoCal Shemales chatroom. I came across her screenname and we started to chat. We traded writen descriptions of one...

3 years ago
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Erotic Massage From A Shemale Masseur

Hello, this is Rahul. This happened when I was on a business trip to Dubai. I am a bisexual guy and like she males, crossdressers. Anyways I found an ad by a shemale offering massage. I booked an appointment and went to her place. Her name was Maria. She was an English speaking shemale from Brazil. I was happy that she was from Brazil since my earlier encounters with Brazilian shemales was very good and satisfying. Maria greeted me with a smile and asked me to undress and lay face down on the...

3 years ago
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my shemale GF part 7 Bukkake

My birthday was like a week ago or s o, and Christy got me what ive been wanting, a bukkake. I finally got this present like two days ago. We went to dinner, we meaning me Christy, Brittany apparently another shemale who I didn't know about but also my friend, and Jennifer, who I did know was a shemale. There are apparently plenty of shemales where I live, awesome. We went to Buffalo Wild Wings, Christy wore a short jean skirt, and nothing underneath, I know cause I dropped my fork and she...

2 years ago
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Shemale Subway Sex

I was out at a dance club with some friends on Saturday night. Clubbing isn't really my scene though, and I soon found myself very bored. Looking at my watch, I saw that it was almost 1 o'clock in the morning. I was having an awful time, and if I didn't leave then, I would miss the last subway train and have to take a $50 cab ride home. So I said goodbye to my friends, and caught the very last train home.The subway ride from the club was going to be around 40 minutes. At first, the car was...

4 years ago
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Sex With Shemales In Train

This was an incident that happened without planning. When our state of Telangana announced that some Corona infected persons have traveled by train, people stopped traveling in trains. I travel daily up and down from Hyderabad to Warangal. One Friday evening, I was returning and the whole train was almost empty. Only about 4 passengers there in the compartment. When the train was on its way, I saw a group of transgenders coming towards me and they were asking for money from every male on their...

Gay Male
1 year ago
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TrannyTube

Who’s ready for some tranny porn at Tranny Tube? I’m going to go out on a limb and guess if you’re reading this, you want to see some chicks with dicks… sucking other dicks. It ain’t really my thing, but hey, I’m The Porn Dude, so I got you covered. Today we’re going to take a look and see why Tranny Tube is currently pulling around 8 million views a month.Tranny has become an offensive word in a world that seems increasingly tranny-friendly. Wake up, you woke fucks. Porno was tranny-friendly...

Shemale Porn Sites
4 years ago
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My Semale Girlfriend part 2

Andrea finished her smoke and too me by the hand and led me downsatirs to her "Fuck room" mirrors everywhere, big T.V. couch, chair, bed and a closet full of toys, everything a sexy shemale or bisexual guy could ever want. We stood in the middle of the room kissing and exploring each others bodies "sit on the couch, put your legs up....." She told me in a very commanding voice. I layed back sprad and lifted my legs, Andrea knelt down and stroked my cock licked sucked my balls. her tounge run up...

2 years ago
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Long sex story 8211 I Was A Reluctant Shemale

Marilee’s fists tightened in despair as she sat at her secretarial desk and listened to the muffled moans emanating from the office of her boss, JC Wyatt. JC was one of the youngest and most famous casting agents in Hollywood and was the most blatant offender of the “casting couch” which degraded women. The young actress, a stunning blonde who couldn’t have been more than sixteen years old, had looked so hopeful when she had entered that office only twenty...

2 years ago
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Shemales humiliate me

One night I was out partying and met 3 girls. They were very sexy and between 20 – 35. One was very dark skinned brazilian hottie and a blonde and brunette one, not very tall. So a couple of drinks later, we went to their apartment (they are living together), things came down really fast. One girl threw me on the bed, the brazilian, as the two others held me down. I was asking what the fuck they are doing and tried to escape them, but they were unhumanly strong. So one girl literally ripped off...

2 years ago
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Trained by a Shemale Mistress Part 1

I did not know it at the time. I thought I was just sleeping around with shemales that I found attractive on Eros, Backpage, and other sites. What I was looking for, subconsciously was a 100% top dominant mistress. In retrospect when I saw the first shemales of this journey I was turned on by their control, but immediately turned off when they submitted to my cock, either sucking it or taking it in the ass.Not until I met Ashleigh did I realize that I wanted to be dominated, not hurt or...

3 years ago
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My Shemale Stripper

This is a true story. The year was 2008. I heard there was a strip club outside of Toronto that was all shemales. The club was celebrating its 5th anniversary and I decided to take the hour and half drive north of the border. I arrived early in the afternoon thanks to my directions from Mapquest and went down the basement stairs. As soon as I walked in, I was greeted by the bouncer/bartender and a beautiful black goddess. I paid my cover, and ordered a beer. “My name is Ashley, want to go for a...

3 years ago
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my first time with three shemales

this is a true story it happened to me back in 1988 when i was still bi i was in a local gay bar it was shemale night close to midnight when i saw this very tall gurl walk in with some friends she was hot about 6' 2" tall with 6" heels" all legs and ass she was blond and so senual with red lips and blue eyes all her friend we shemales too. After the got a table and ordered some drinks the music started so i went over and invited her to dance and to my surprise she said yes so we dancwd this...

3 years ago
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Shemales humiliate me

One night I was out partying and met 3 girls. They were very sexy and between 20 - 35.One was very dark skinned brazilian hottie and a blonde and brunette one, not very tall.So a couple of drinks later, we went to their apartment (they are living together), things came down really fast.One girl threw me on the bed, the brazilian, as the two others held me down. I was asking what the fuck they are doing and tried to escape them, but they were unhumanly strong.So one girl literally ripped off my...

3 years ago
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Me And Two Shemale Lovers

The ad in the local “underground” paper said “2 hot she-male lovers looking for inexperienced open-minded male for exciting new encounters….” It added a few brief descriptions etc. I thought to myself. “Why not, you’re open-minded and adventurous?” So I gave them a call, wondering about the details. I’m not totally new to the scene and have dabbled a little in being in the bottom or receiving side of anal and while I never have travelled the shemale route, it always intrigued me. I have seen...

4 years ago
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Celebrity Shemales

Here, you can fuck the shemale version of your favorite celebrities! Feel free to add new celebrities! IMPORTANT: Leave a like for whichever celebrity you want me to write a shemale story for first!

Transsexual
2 years ago
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Sex date with a sexy shemale

For already several weeks I surf through a website that advertises women, men and also shemales. Since my great experience with the other shemale during my holiday (see one of my other posts) the craving grew bigger and bigger to meet up with one again.So last night I decided it was that far. I drove to the address I got from her on WhatsApp and rang at the door. After paying her the agreed amount (love the humiliation factor of this, need to pay someone to fuck my ass) she showed me the...

3 years ago
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She turned into a Shemale

The weekend had just got under way and from the start of that Saturday you could tell something was in the air. She was acting like a shark with blood in the water.The day started with her rolling over and grabbing my Ballz with an aggressive fist, stretching them out, shaking my cock.The signs were there for a day filled with wonder and experimental crazy sex. The day moved along slow after that, we went out shopping, she tried on dresses to tease, we ate and just spent the day wandering...

4 years ago
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A shemale transformation part 7

So i woke up in my room thinking i just fucked my mom but it was a dream also the name that i gave in my dream was not her real name my mom name is Jennifer she got big hug tits i mean nice round big perfect. She got big booty thin body thick legs anyway. As i was wakeing tho my door had been kinda open. I know somebody been watching me sleep or as come in my room i never leave the door open. I walk over to the door mmm nobody there then i close it and start geting ready for school i took my...

4 years ago
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Shemale massage

It has been one of those long and stressful weeks. I’m in desperate need of relaxation and relief so I head over to an Asian massage parlor for a typical happy ending massage.The girl who usually massages me isn’t available so another girl is suggested which I accept. I think to myself that she can’t be much different than my usual so I don’t care much. I just need a massage badly.She comes out of the back from another massage and introduces herself as Jessica. I smirk a bit knowing there is no...

2 years ago
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Shemale Gangbanged

Hi........readers.......i am a shemale whose presence looks like an angel.......Due to my physical appearance....boobs,ass....whatever boys use to look at is as soft as cream.My story starts with a mistress ....who fucked me twice....but without any payment...So it was a summer and i called him to pay me....he told sure u come to my home .....i will pay you.I thought why he agreed so easily.....but any how i thought what he can do ......maximum he will again fuck my ass and suck my boob snot...

4 years ago
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Brandi the Shemale Cums After MNF

So, I come home from watching Monday Night Football with some guys at the local pub. I turn on the TV and some infomercial for an exercise machine comes on. The model working the machine has a great body and seeing her workout is really working me up. My cock even gets a bit hard.Feeling a bit on the adventurous side, I open the phonebook and look for an escort service that has shemales. I find one. Just talking to the dispatcher and describing what I want makes my cock hard again.The hour I...

3 years ago
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White Male Asian Female Revolutionary Party Part 2

'Have you heard the news about the white men?' he said, looking around at his friends in VR chat, most were similarly engaged in sexual fantasies and not much interested in the chat aspect. His all Japanese group of friends looked just like him despite their situation, the possible issue of players becoming so...

2 years ago
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My first time with a shemale true story

My girlfriend had been out of town for a couple of weeks and i was so horny and wanted to get upto something kinky.I called a shemale site from la costa del sol called taiakshemales and arrange to meet one of the beauties.I was very nervous as i drove to her house as i never touched a dick before.Once i was in her room waiting for her to come out she was wearing this sexy lingerie very slutty and a bead panties that just went around her tool.She asked me if i had any experience and what i liked...

4 years ago
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Transsexual Shemale

TRANSSEXUAL You are not a woman; You are not a man; You are opposites united In a hermaphroditic plan, Perfection, Completion, Wholeness, No longer a person divided Into separate houses, Separate camps; Your genitals--penis and testicles-- And your jutting woman's breasts And buttocks transform you, Save you from the curse With which the rest of us are cursed, Remaining only men or women Instead of a goddess Born of hormone therapy, Surgery, And a desire to...

3 years ago
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Star Wars Young Jedi Knights The Female Conspiracy

Disclaimer: Star Wars and the main characters within this story are property of Lucusarts Ltd. and are used solely for the purpose of entertainment and not for the gain of any moneys. The Female Liberation Movement/Army and named members; fem-troopers; the Rhenda's Haven resort; Sarrifiss; and the Jedi Mirram Moss are my own creations. Any questions or concerns about this work of fan fiction by Lucasarts or its representatives are to be directed to me, the author, and not the...

4 years ago
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Female Orgasms 101

Orgasms 101It is surprising that later in life, a man may still not be sure if and when a woman orgasms. Thus, the reason for this story. Men don't feel bad. Women aren't expected to know when or how a man orgasms. He just stops momentum and displays the obvious (excluding a cumless climax). Orgasms are about life and not just sex. Orgasms sure do keep a woman happy. As a woman loses her inhibitions about sex, the easier it is for a woman to orgasm. I'm going to explain to you when you are...

2 years ago
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The shemale transformation Part 8

So my mom got taken by bigbirtha and i cant believe this happen i mean bigbirtha said she wouldnt harm my mom if i fucked her whats even more bad is that my stumic geting greener something slowly turning me into something even more monstrous well i must get some rest for school next morning ebony cam over she told me aliens have been beeming the girls locker room and that Vanessa is back. Ebony asked do you still love her i side kinda i mean part of me always will but im with you now you...

2 years ago
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When A Straight Falls For Trans Shemale

Hiya guys.This is Aaxer with a new plot and a new story.This story will be different and actually is from the last story.I entered a real different experience this time.It feels shy and embarrassed to express it but I won’t keep you from experiencing it once you have read this story.Let’s jump to the story. Alright, here I’m in a bus moving out to my room as I’m a student in a good reputed college in Pune.I used to catch the bus from PMC depot.I always spotted a girl every time on the ride...

Gay Male
4 years ago
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Two Sex In Two Weeks 8211 With A Shemale And Then With A Married Woman

Hi to all the readers of ISS. I am a great fan of this site. I am Ronald from Mumbai . I am 24 yrs old. I am a football player.I am 5ft 10 in my penis is 6 inches I hit gym regularly. Now lets come to the story. This story is about 2 months old I went to play a match in my friends area. The ground was situated between apartments on all all four sides. While the match had half time I noticed a women from first floor looking at me . As the match was over still she was starring now I knew what was...

3 years ago
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Our First Female President

Chapter 69 – Costume Gala Please take note! Adults Only Literature The text in this story contains erotic material and is expressly writtenfor adults only. If you are an underage minor or offended by such material -or- if viewingthis file is illegal in your locality, then leave, close or delete this file-storynow. This is a work of fiction, any resemblance to persons living, dead or otherwiseis purely coincidental, etc. Email [email protected] with your comments. Copyright 2004 **** ...

2 years ago
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Female fragrances

Hi!This is Sunil again and wishing the best for ISS readers.In my previous stories I had told you about my voyeuristic sexpade with my Mami in Pune and then much later sex with her as Mama failed to satisfy her and during the course of our sexual dalliance she became pregnant and now has a beautiful daughter from me.It was during this dalliance that Istarted worshipping female body.My Mami is a queenlike looking Kokanastha Brahmin with creamy peach complexion and light eyes.She tall and bit...

2 years ago
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My Wife The TOP ONLY Malay Shemale

Hi all, my name is yarra (not my real name perverts!!!) and I am a proudly married matured male, now 57 years old.My wife, 52 is a (or was a) biological female technically, been married to me for the past 24 years.Let me tell you my fantastic and totally out of this world story.Flashback to 24 years ago, that is the 1989, when i just reached my 30'ish age, you had read my earlier life story in this "Xhamster" site, where I started my strange relationship with my shemale mother, the one who had...

2 years ago
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A Shemale Vacation Part Two

A Shemale Vacation - Part Two by Richard-to-Rachel We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragement, very quickly changed in demeanour when he discovered we had not the money to pay. He became quite threatening and aggressive and we...

2 years ago
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Sex experiences of a slutty shemale

« Bhopal girl fingered by boyfriend in hotel room mms | main | middle east lady Officer dressing up after fuck mms » Sex experiences of a slutty shemale Posted on december 15, 2008 12:00 pm, filed under straight couples Hi! This is priya, 21 years and i am a shemale. Hope you know what’s a shemale. I was born as a boy; but i always wanted to be a girl right from my childhood And so, i had medical intervention to change my sex. Since my parents are rich And supportive, I could well afford for...

Incest
1 year ago
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My Indian Shemale Mother Part 1

100% fiction! I woke up the next morning feeling warm and contented. I opened my eyes to find myself lying in my mother's bed, completely naked, covered by soft, do wny blankets. I looked at the clock. It was nearly ten AM! I was going to be late for Office! All at once, the memories of the previous night struck me. I remembered my mom and I watching a shemale porno together, masturbating together, bathing together, and finally sleeping together. If this could be called normal, that was...

Incest
3 years ago
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Stolen Stockings Pt 1 SHEMALE LESBIAN PORN

WELCOME TO CHURCH OF RUBBER - STOLEN STOCKING CONFESSION .the sign read above My study doorway.My transex very leggy young secretary nurse led the new prospect in to My parlor and knocked on my door and I said "COME"the heavy gothic arch door swung open and there stood the two stunning transexual stocking sluts in ultimate sissy wear. One happened to be My private nurse and secretary, the other was a specially chosen pretty thing who had been in communication with ME for some time now. My...

2 years ago
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Shemale Surprise

This is 100% true, I know it may sound difficult to believe and I know if I read what is detailed below I’d struggle to believe it but this is what happened to me on Wednesday.I needed to take Wednesday off from work as a holiday to get some work done to my home, as the day wore on I had planned to get a tribute made, but I felt too horny to tribute I’d been to Northwich Sauna before (Which I’ve posted about before) and seen that they run a TV/TS day on Wednesdays, all are welcome to dress how...

3 years ago
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Nazoo aur Indian shemale and boyfriend

Heloo meri lesbo friends!mera naam nazoo khan hai.main 28 saal ki bahut gori chiti sehathmand sexy badan wali behad khubsorat larki hon.meri figure size 38 28 38 hai.mera aik boyfriend hai jis k 9inch lamby aur 2.5inch motay goray lund ki main dewani hon. Wo main usse khub chudwati hon,hum dono na bahut se khubsorat larkion aur jawan sexy aurton k sath sex ka maza liya hai.muhje yaqeen hai k ajj ki story ko read kar k mero lesbo dosto ki chuton se bahut pani nikle ga.ab ap meri real story ko...

2 years ago
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Future Fucking Powerless Females

On Nov.4, 2036, the New Puritan Party captured the Presidency, a solid majority in the House of Representatives, and 28 of the 34 seats up for grabs in the Senate. Members of all political parties recognized the trend and quickly fell in line behind President Daley, who had campaigned on the slogan, Bitches: Am I Right, Guys? Curiously, he'd garnered 39% of the female vote, which kinda/sorta/maybe proved his point.Anyway, he quickly set about stripping girls and women of all rights, including...

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