Shemales Porn Stories
Page 10

My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the room. Like I said there were lots of beautiful ladys there but one caught my eye. She was not too ta... Continue»
Posted by wildbill975 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 4088  |  
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My first time being taken dressed as a woman

I'm a 42 year old married bisexual guy, slim built, average height and shaved below. Ive had a few encounters with other men but none dressed as a Woman.
Ive had fantasies for years about wearing women's clothes and make up. Unfortunately I haven't had much opportunity for either, that was until a few months ago.
As it turned out my wife would be away for 3 weeks and opportunity presented itself. I quickly got down to planning and slowly but surely a plan came together, well sort of anyway.

I went online and ordered some womens lingerie, wigs, panties, make up and a few slutty costumes, ... Continue»
Posted by jimbo70xyz 1 year ago  |  Categories: BDSM, First Time, Shemales  |  Views: 4090  |  
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First time dressed as a woman

Ok, this is an absolutely true story.

I'm a married white guy, stocky, 6'1" with a 5-1/2" cut dick. I've been dressing up on and off since I was a p*****n, starting with my mother's lingerie and dresses. I love makeup, but especially lipstick. I used to masturbate by stroking my cock with a bl**d red lipstick while reading those old trashy porn novels you could pick up in the seedier luncheonettes.

I always denied my cock loving side, imagining myself as a lesbian for the most part, but I fantasized a lot about sucking cock and getting fucked. Once I'd cum I'd feel ashamed and try to... Continue»
Posted by kevinj631 12 days ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 4070  |  
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Losing my Cherry

Although l have been secretly cross dressing for years I have never took it beyond the confines of my bedroom or hotel room. Well I have been really wanting to take this to the next level. So as I was traveling on business this past week I answered an ad on Craigslist for a massage in my hotel room from a male masseur I made the appointment and waited with anticipation for my masseur to arrive. At promptly 8:00 there was a knock on the door and when I answered there was Chris a very handsome young man, I invited him in and he promptly set up his table..
As he was setting up his table and ... Continue»
Posted by mikkas72 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4049  |  
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My new "GF": Danielle's untold stor

My New "Girlfriend": Danielle's untold story.

My name is Danielle, I grew up with both of my parents in a big city. My dad's name is Adam and my mom is Samantha. My parents got married after I was born, they met in high school and that they've been together ever since. My parents say that my name was "improvised" since the doctors made them think I was gonna be a boy , but when I was born I was classified as a girl, it's just that I was born with a full sized penis above my vagina. Ever since I was just a little girl I remember feeling... different because unlike the other girls at school, ... Continue»
Posted by adblman 1 month ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 4046  |  
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becoming a slut

It all started when I was 13 and discovered the joys of wearing women's clothing. It started with my older s****rs panties then my highschool girlfriends things by the time I was 18 I had a pretty good collection of womens clothing even with never having the nerve to purchase any of them myself. Then came the urge for more when dressing up and masturbating wasnt enough I wanted more. I always considered myself straight despite my crossdressing but when dress would get the urge to please a man. So one day I got my s****rs 7 inc dildo. I got dressed up in some sexy thong panties some nylons and ... Continue»
Posted by RenoBoi 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4043  |  
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My New "Girlfriend"

Let me introduce myself. My name is Kevin, I'm 23, I live alone in a two bedroom apartment and I work full time as a store manager. My last relationship lasted 3 years and we were together since high school but both of us split about a year ago. 

It was a long day at work today so I went to a local bar to hang out and meet hot single women. Once I arrived at the bar, I could see three hot looking women glancing at me, checking out my slim, somewhat muscular body. I walked over to one of the prettier looking ones and I said, "Hey beautiful, can i get you a drink? She replied, "I don't know..... Continue»
Posted by adblman 1 month ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 4038  |  
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Sex with teacher(sissy)

I was the 2 year of high school back then. My grades werent going realy well moastly becuse i spent most of my freetime blowing guys,and sticking thing in my ass,then studying.My parents one day decided that i need some extra classes,so they hired a tutor. I wasn't realy up for that idea,but they somehow talked me into it. After a while it was the time for me to have my first class. My parents left for work,and i was home alone waiting my teacher.Then the dorbell rang , i felt so nervous as i opened the door. In walked a handsome 25-6 year old man,fresh out from college,in a very nice suit. We... Continue»
Posted by sissygirl1988 1 year ago  |  Categories: Anal, Shemales  |  Views: 4030  |  
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The Surprise Vacation



The Surprise Vacation


by an unknown author and Tristmegistus

1. Chapter - Innocent Beginnings

"Did you take your vitamin, dear?" Ellen called from the bathroom.

I rubbed sl**p from my eyes and picked up the pill bottle, rolling a big
tablet into my palm. "My horse pill? I'm doing it now."

"Have you noticed any difference yet?"

"Nah. Vitamins are pretty much all alike." She'd gone on a minor health
kick a month before, insisting that I needed to lose a little weight and
take better care of myself. I hadn't actually made it to the gym to wor... Continue»
Posted by klammer 9 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 4031  |  
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Frank's Friend

Frank is a buddy of mine. We grew up and went to college together. While we were in college Frank and I went on a road trip from Lubbock to Dallas. We got to Dallas went to a few strip clubs and then finally found ourselves on Harry Hines Blvd. It was about 1 in the morning we were both horny and a little d***k. Frank pulls up to this leggy blonde in a short skirt and fishnet hose and asks how much. She told us she would do us for free for a ride home. We said fuck yes. Frank had me drive to her house while he had her in his lap, kissing and groping her. We got to her house and went i... Continue»
Posted by biguy52x 1 year ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 4019  |  
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The Truckers Reststop

I had to work yesterday, it was Saturday,I had made plans to spend the day being the slutty little whore for the whole day, but work got in the way. I came home felt tried so I soaked in the tub, shaving my legs and puss yass and gurly clit. The weather was bad all day, when I finally decided to Fem myself up it was already 8pm, so I thought what the heck I'll drive up the Interstate just north of Seattle to a truckers rest stop I have gone too before. The weather had cleared up a bit, so I was hoping for some fun. I dressed in my short wrap around skirt, red thong panties, red Bra, and a shea... Continue»
Posted by cd_lorretta 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 4018  |  
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Wife turns white hubby into black cock cuckold s*s

"Oh my god!"

My wife looked up over the muscular shoulder of the huge black guy nailing her on our bed. Her long tanned legs wrapped around v-shaped torso. "Hi honey. What are you doing home early?"

"Kelli what the fuck's going on here?!"

At that, the black guy turned and shot me a nasty glance. "What's it look like we doing, genius? I'm dicking your old lady. Now get out of here fuckshit I ain't finished."

"Better go downstairs dear," Kelli said, smiling. "I'll be down later to explain."

Of course I was shocked, but what else could I do? I went downstairs poured myself a drink ... Continue»
Posted by whitewhores 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 4016  |  
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she trained me

I was sent to Aunt Fergie when my parents were killed. She is about 5'7"
and 200 lbs she was your stereotypical aunt with some fat and wide hips and
big breast. She picked me up at the bus station in her car.

She said," My household is different and special I have girls who you
will find are very unique. I too am unique and I will show you what I mean
when we go home."

We rode for a half-hour and we arrived to her big old which I would find
was an old Victorian with a widow's roost on top of the roof.

She e****ted me to the bedroom that would be mine and told me," Put your
... Continue»
Posted by pcarter 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 4009  |  
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SOMETHING ABOUT DANNY

What was it about my daughter's boyfriend that turned me on so much? No one characteristic comes to mind. I suppose it was a combination of things. And perhaps a certain time in my life also. I was 52, divorced, alone and quite bored.

I had been divorced from my husband Jerry for 12 years and didn't really have a steady boyfriend. Jerry and I remained friends but he seemed to be turning into an old man. I was still young at heart, or so I felt. But the more men I met the more disappointed I became. It had been getting to the point where I would rather stay in my apartment and read than go o... Continue»
Posted by couple_kinky 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 4008  |  
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fucked by indonesian ladyboys

this is a true story of what actually happened to me in bali

When i was 17 i was on holiday in bali, indonesia. i'd only had sex once prior, with a genetic girl, and i barely managed to get hard and wasn't able to cum so i knew pussy wasn't for me.
i had been clubbing several times on this trip to bali and had been hassled by numerous prostitutes while out but wasn't interested, except for one night whilst walking back to my hotel on a quiet street in legian, a deep but seductive voice called out "hello" to me from the shadows of a run down apartment block, emerging from the dark stood a ... Continue»
Posted by yuneeqboi 2 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 3982  |  
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the surprise I loved

I never had never heard the term shemale or transexual. Didn't know anything about it. I joined the military right out of high school. Ended up in the far east and started out on the town. I saw a great looking girl in a bar and started to chat her up. I bought a few drinks and we were both starting to loosen up. Then out of the blue she asked if I wanted to get out of there and sme place more private. Now I had a few girlfriends in high school and had sex with a few of them but i had never had anyone address me like this. I wasn't she what her intentions were but I knew I wanted to fuck her. ... Continue»
Posted by gayswitch 2 years ago  |  Categories: Anal, Shemales  |  Views: 3978  |  
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Down the Path

Down The Path


I hear the knocking on the door. Have my panties on under my shorts and tshirt. Nervously open the door and the man comes by me and I follow him into the living room.

He stops and turns. 'On your knees now'. He moves in front of me showing me his ID so he knows I know who he is in case he gets out of line. 'Tell me why you invited me here.' Looking down embarrassed to have to say it. 'I invited you here to treat me like a faggot Sir. I need a real man to come over occasionally and show me just how much of a fag I am.'

He lifts my chin with his finger then suddenly he s... Continue»
Posted by lookin02 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 3978  |  
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My one and only experience with a tranny/shemale

One Friday night I decided to take a ride to Hollywood to check out adult theaters as i had always gotten my cock sucked at different adult movie theaters. As I parked my car on a side street i walked to this one particular movie theater I found myself at entrance and paid the 5 bucks to enter. as you all know, when you go into any movie house, its always dark and you wait for a few minutes for your eyes to adjust to the surroundings. i was standing near the entrance and looked around to find an empty seat. i always look to find one in the back near the isle, but they were taken, so i went... Continue»
Posted by 1superhornyguy 1 year ago  |  Categories: First Time, Mature, Shemales  |  Views: 3968  |  
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S****r has a Secret

Sarah was rummaging through her bedside drawers, turning them out and messing up the room she shared with her younger s****r, Hope. She was looking for her ipod. She had no idea where she'd put it when she'd gotten home the night before.

It was when she reached her bottom drawer than she found something interesting. Pulling out the stack of photographs that she hadn't known was there, she became furious. They were nude photographs of her, in the shower and masturbating.

Sarah was a transsexual. She'd had a sex-change when she was 18 because she'd always felt wrong in her male body, thoug... Continue»
Posted by drew1207 1 month ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3966  |  
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On the road

Dannielle had decided to finish work at dinner time and go for a drive the long way home seeing as the day was so nice. As she got into her car she thought "i will put the soft top down and get a tan". As she got in the car she looked at herself in the mirror and checked her make up, hair and her top. She had noticed how the boys in the office had been looking her up and down during the day, well she had dressed for the attention. Her tight white top that showed her black bra off really well and her short black skirt that was so tight that you could notice the outline the suspender belt she wa... Continue»
Posted by danni1 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 3962  |  
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