Shemales Porn Stories
Page 60

The trannt from work

I've always had a thing about trannies. Just something. Never sure what or why. I loved looking at them. Seeing their huge tits. Their nice asses. Then seeing a dick between their legs. Now I'm not gay but, was always interseted. I would look up e****ts here in town just to see how far I would go. Finally one day, I got the nerve to do it.

Her name was Angelina. She was about 5'4". Say 125 with some hugh tits. Say 38 D or so. I had seen her where I worked. Would of never thought she was a tranny. Just always saw this hot chick with a huge rack & a hot ass. Everytime she came in the store, p... Continue»
Posted by radec_24 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2656  |  
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Tranny and Me Meet The MILF

This past Friday morning my phone rang. It was Chandra my tranny friend who I met and fucked some weeks ago. She told me that she had nothing to do this weekend and that her roommate was out of town and she was alone. I told her that if she wanted to get out of the city that she could spend the weekend at my place. She said that was a great idea and that she would be over in a few hours. When Chandra got to my place she was horney as hell. She dropped her overnight bag, dropped to her knees and opened my pants. She pulled out my cock and began to suck it really good. She was licking my balls, ... Continue»
Posted by adw276 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1784  |  
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cruisin the park for sex

when I started crossdressing,I was bout 15,a few later I got my own place,and was able to do more,except getting in clubs.I was 19yrs old when I got my first appartment,and was not able to get in,cause at the time,the drinking age was 21.and the club,Call club park avenue,hottest gay cub in town,well it was the only one.well I would crise the park where the club was,which was uptown in a very nice setting.so on fridays,and sats nights,I drive around the park looking for hot guys to have sex withI would all way wear a short sexy skirt,and a low cut top,under that a bra,panties,matching gartbel... Continue»
Posted by blonde68 1 year ago  |  Categories: Shemales  |  Views: 617  |  
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Morning Routine at the Mansion of My Misstress


My eyes open with the gentle humming of my small alarm clock. I quickly shut it off so as not to disturb anyone else in the room. Its 4:30am, well before light creeps into the day and the room is now pitch black. Very quietly I rise up on my hands and knees and crawl off of the small doggy bed on the floor next to the big bed. It‘s embroidered with my name “Heather” in pink because it’s my bed and I’m the pet of my Mistress.

I’m silent when I move because I have done this so many times before. On all fours I make my way to the master bathroom and gently close the door behind me. I then st... Continue»
Posted by heatherlingerie 2 years ago  |  Categories: Fetish, Shemales  |  Views: 1142  |  
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my first tranny pt. 2

it hurt so bad but felt so damn good. I told her just to stay still so I can get use to it. get use to having a cock in my ass. that was a totally new feeling. it was something I always wanted to try. now I was.

she slowly started to move back & forth. not really pulling out, just enough to make me feel better about it. she was stroking my cock, which was rock hard. I could feel her balls on my ass. deep down i was freaking out. this is really happening. I knew that coming here I was going to fuck some ass. not get my ass fucked.

eventually, I got use to her cock in my ass & she was pu... Continue»
Posted by radec_24 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1426  |  
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Courtney and Michael

I wrote this last Christmas Eve and sent out to friends who've provided me their email. I tried to include the photo that was the inspiration but couldn't get it to show ... it was stellar! So enjoy ...


"Oh Michael, you're company's holiday party is always so boring! Do we really have to go?"

"You know Courtney that I am expected to be there. I AM the Senior Vice President, after all."

Michael wore his typical grey business suit with a festive tie to the event. Courtney, a tall, shoulder-length blonde, wore a black mesh dress with black stockings and boots. The party was held ... Continue»
Posted by call_me_dana 2 years ago  |  Categories: Shemales  |  Views: 951  |  
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Bus Stop

Dressed with my red 17cm boots, fishnet stockings, transparent skirt and transparent top I was waiting at the bus-stop to go back to my hotel in Barcelona, but suddenly a car behind be honked.


A beautiful Spanish guy stopped and looked at me, he couldn’t leave his eyes from my beautiful huge tits under the shirt. He whispered into my ear, “Need a ride?” I wasn't even startled and thought if this guy would have a nice cock as his body it would be a good start for the night…. I said “Sure, let's go.”
I saw tha... Continue»
Posted by Sexysamara 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1200  |  
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First BJ

Coming home one day a school bully caught me in an area of trees and bushes. He often tormented me and others, being a stupid bully. On this day he ran at me telling me to freeze where I was. I turned and ran. Which set him to cursing me and demanding I stop. He caught up with me and grabbed me by the shoulders. He got in my face and called me names. Fag boy because I was slight and feminine looking, wimp, pussy etc. I begged him to let me go home but my pleading only seemed to increase his pleasure in over powering me. Then he told me since I ran, he was going to de-pants me and make me wal... Continue»
Posted by Celine-Fache 9 months ago  |  Categories: First Time, Shemales  |  Views: 2407  |  
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He makes me feel so GIRLY

My friend that you all see fucking me and me sucking his big cock in my pics and videos. We will just call him Mister. Well he came over this morning for some Sunday fun. He is so good to me he really knows how to make me feel like his girlfriend. Today was so yummy I am still sexually excited just thinking about it.
I was dressed and ready for him when he arrived. I was wearing my sexy white lace halter top and black thigh high stockings, with the cutest little white G String with a sexy little flower in the back. Topped off with my silver jewelry and 6 inch black heels. I was so excited to... Continue»
Posted by Naughtynina 2 years ago  |  Categories: Shemales  |  Views: 1055  |  
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A Special Girl - Birth of a Special Girl

A Special Girl - Chapter 1

By Alhana Escher

Birth of a Special Girl


James’ world had been turned upside down. Just moments before he had been getting off with, in his opinion, the cutest and sexiest girl in school. Now though, his was totally freaked out sitting on his living room floor having just discovered his girlfriend Alice wasn’t actually a girl at all. He had found out when his hand, that had been slowly making it’s way up her legs underneath her dress had reached the silkiness of her knickers to find a unexpected surprise waiting within. A small, but definitely hard ... Continue»
Posted by AlhanaCD 2 years ago  |  Categories: Shemales, Taboo  |  Views: 2318  |  
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first time crossdressing exp

well this hapened a few years back,ive always been into wearing lacy underwear etc so i put an add in for anther knicker wearer for fun in an adult contact site,and was amazed at the replys,anyway i met a guy and we got on so we arranged a meet later that week at his house,i got there had a couple of drinks as it was our first bi experience, so he went upstairs to get changed and i got changed downstairs i put on black see through lacy knickers sockings and matching bra and mini skirt white blouse and a wig,dave came down wearing a very sexy outfit which was similar to mine also complete with ... Continue»
Posted by mumlover1960 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 874  |  
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becoming a bitch

Becoming a Bitch
It was supposed to be simple. A blind date, set up online. A hot chick. Me getting laid for the first time
in a while. You know. Simple. And that's what actually happened. Sort of.
I get to the bar, I see Meghan across the way, sitting pretty in a short black dress, legs crossed,
sipping on a martini like she's sucking my cock already. Far as I'm concerned, I'm as good as fucked,
the way she's making herself out to be: smooth thighs, big, round tits, lips that could blow the cap off
a bottle of Bud, legs long as tomorrow and an ass as big as today. Fuck, I feel I'm in th... Continue»
Posted by pr1456a 10 months ago  |  Categories: Fetish, Shemales  |  Views: 2200  |  
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MY GIRLFRIEND HAS A PENIS???

I met Gina at a club she was by herself at the bar and when I looked at her I was smitten I knows that sounds cliche but it was like that for me! I sat down a few seats down and ordered a drink a whiskey sour I believe it was took a few pulls to get up my courage then I offered to buy her a drink and she looked over at me with these incredible sea green eyes and actually smiled at me "Ok " she said and ordered white wine which she sipped so sexily I asked her if I could sit beside her and she patted the seat next to her I couldn't believe my good luck to find such a babe here and she likes ... Continue»
Posted by laceysgirl 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 4092  |  
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A true story: me and a transvestite man - part 1

This isn't a 'story' at all, in the sense that it really happened. I just thought I'd share my experience with you; perhaps you'd care to comment if you enjoyed it, found it sexy, or want to know more.

There isn't a 'transvestite' niche on xHamster, so this is filed rather awkwardly under 'Shemales' 'Gay male', and 'First Time'.

OK, about 10 years ago I discovered that I got turned-on by 'shemales'. Let's be clear about that: shemale is a casual term for transsexual men, that is, they were born with a male body, male genitals, but for whatever reason, don't want to live as men. Today,... Continue»
Posted by LookingForSomething 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1073  |  
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A Slut is born


There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends.
I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town,
dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat?
It had all started a few months ago. I was locked out of my house in the pouring rain,
and I went over to our neighbor’s to see if I could hang out with him until my parents got home.
He was a cool guy... Continue»
Posted by vosmou_vrot 3 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 4239  |  
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foxxiroxxi takes two BBC,s in sex shop

The other day i went shopping for a sexy fetish outfit for a fancy dress party , the theme was doctors and nurses so i decided to suprise everyone at the party and turn up in a naught nurse outfit with platform heels . Looking online i found a sex shop that had the outfit that was going to blow every girl away at the party. It was red and white extremly short and tight , they also had all yhe accesories to go with it . When i got to the shop there was this big fit and very hot black guy w... Continue»
Posted by foxxiroxxi 1 year ago  |  Categories: BDSM, Interracial Sex, Shemales  |  Views: 1212  |  
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Fulfilling my babys fantacy

Fulfilling my babys fantacy

You and I have been having trouble letting each other know what our fantasy's are.
You finally told me about your transsexual interests thinking that I would think your weird.
But was happily surprised that I fully supported you.
We had been chatting with fairdesire for a few months and I wanted soo badly for you to fulfill your fantasy.
I seen several raffles for to win trips over seas and bought several.
I WON THREE !!!!!
Oh my goodness, I had a hard time keeping my mouth shut about winning 3.
I only told you about 1.
And sent on... Continue»
Posted by tnt88jean 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 1032  |  
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I've always wanted to meet a gurl!

First of all I would like to apologize for my English.
Hello there! I live in a small country's biggest city and here people are strange. If they are crossdressers, shemales, trannies, tgirls, gurls (actually we have only 2 words for a shemale, so I don't know which one is NOT offending please excuse me I do not want to offend you or what so ever) usually do everything for money, or they lack good health, hygiene or I haven't met the right one. This is was a bit new for me. I've always wanted to date a gurl. Not just the sex part, but actually get to know the person, to fall in love and thin... Continue»
Posted by AngelPetrov 2 years ago  |  Categories: Shemales  |  Views: 467  |  
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Sissy Slut Amanda Part 1: The Beginning

The Story of Sissy Slut Amanda

This is a story of fiction

Part 1: The Beginning


When I was twenty-three I meet my Sissy Slut Amanda for the first time. Now he was only eleven at the time and it would be many years before I would know him as Sissy Slut Amanda, but still funny to look back at now. The first time I met my future sissy slut, he was Mark, son of the woman I was dating. He seemed like a nice k**, very shy and timid but sweet nonetheless. It’s wasn’t too long after our first meeting that I would be asking his mother to marry me. We had a good marriage and although I nev... Continue»
Posted by TheSissyFucker 1 year ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2399  |  
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The Triple X cocktail - Wife Shares Shemale With H

"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an hour see you." She hung up.

The phone call made me really nervous.I had reasons to get nervous if not get a nervous break down. Tara and her husband owns a few restaurants in different cities across the States. I have known Tara since 6 months now since she busted me from one of the restrooms of her restaurants. Well wh... Continue»
Posted by Copious 2 years ago  |  Categories: Group Sex, Lesbian Sex, Shemales  |  Views: 4597  |  
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