Shemales Porn Stories
Page 10

my first time




My mother always said she wanted a daughter….my guy name was Adrian, so you could see where she was going with that. I was also a real sissy as a k**, terrible at sports, threw like a girl, did very few real boy things.

My best friend and I discovered porn and masturbation together. My mom didn’t watch what we were doing too closely, so we used to jerk off down my basement like all the time. We would get a Playboy or some other skin mg and just go to town. He would catch his load in his hand and dump it down the sink (what a waste) but I would usually shoot my load on the floor(anoth... Continue»
Posted by adrienneheels 1 year ago  |  Categories: Shemales  |  Views: 3837  |  
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Caught in the Act....

One summer, my cousin Nancy came to stay with us for a while, as her parents had gone away on a cruise trip. At 18 years old, she was a couple of years older than me and in the full bloom of her young womanhood, so to speak. She knew it, too, and it was obvious that she had no problem at all in pulling any guy she wanted. Not only did she look good, but always dressed very sexy, just to make sure…

She was another of these girls I adored during my adolescent years, who LUVed to teeter around perched on very fine pointy hi-heel stilettos, and when she walked, her butt swayed from side to side... Continue»
Posted by caroletv31 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 3815  |  
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Alice 1

Alice

My name is Alan Smith, I am twenty two, about five foot six, fairly slim at just nine stone, my hair is dark blonde and fairly long, sometimes I put it in a pony tail. I have a degree in computer science, I work for an I.T. company, travelling around the southern half of England fixing computers and programming. I live with my dad Greg in a quiet suburb in Essex. My mum Elizabeth left us about four years ago, that was such a surprise as mum and dad got on very well, there did not seem any reason for her to leave, but dad and I have ... Continue»
Posted by ratty9uk 3 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 3807  |  
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Daddies likkle baby girl

Once I had discovered that my role in life was being a sissy girl, I and my Daddy took our relationship further. I started growing my hair, who would take any notice, lots of men have long hair. I also allways had sheer stockings and satin panties on under my trousers when i went to work. I would join in all the macho bull at work talking about girls tits and the usual banter, all the time wearing more satin and silk then there fat ugly wives would ever wear. One day Daddy phoned me to say he was outside my office with a present. I went outside to see him in his car, he handed over a plastic b... Continue»
Posted by igglepiggle 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3795  |  
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Chloe's Slutty Night at the Truckstop

If you have read any of my previous stories, you know that the freedom of college took my secret life as a slutty cross dresser to a whole new level of naughty. I became a great cocksucker and I started to constantly crave a hard cock in my boypussy. I started dressing more often, going from 1 or 2 times a month to at least once a week. I was building up my collection of clothes and toys and getting more and more daring every time I went to meet a guy. I started to just go to my destination in full slut attire instead of getting dressed when I got there. Anyway, this constant escalation of my ... Continue»
Posted by cumslutchloe 13 days ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3811  |  
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An Evening With A Beautiful Woman And Her Cock

An older man finds an older woman and her cock at a Spanish class.

With winter coming to an end I was taking a class in conversational Spanish at the senior citizens centre because I planned to travel to Spain or Mexico next year. The people in the class were about my age, 60 to 70. I was fortunate enough to sit beside possibly the most attractive woman in the class. Unlike the others she dyed her hair a bright red and, come snow or sleet, she always wore a dress. For a number of classes we worked together trying out our poor Spanish until we could both ask where the toilet was, or order a... Continue»
Posted by smallfurrycreature 1 year ago  |  Categories: First Time, Mature, Shemales  |  Views: 3790  |  
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My 1st interracial threesome

I met a guy and he came to my hotel after meeting him on a social network site. He was 6'2 and around 225 pounds military man. We instantly hit it off when he came into my room and gave me a passionate tongue kiss. He then dropped his pants and I sucked his hard 7 1/2 inch cock, he then ate my sweet ass pussy until I couldnt take it any more. Then he topped me and gave me a huge load. About 3 weeks later, he said he wanted some more, I told him that I was super horny and always wanted a 3sum. I was house sitting for a friend and after we emailed each other for about an hour, he agreed to have ... Continue»
Posted by charlie39212 1 month ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 3787  |  
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My Uncle Wally's Sissy Boy Wife

Penned by: Miss Deborah (Debi) Leigh Johnson



One



I did not know what I could expect, as the Greyhound pulled into the
bus station. I did not know a whole lot in fact, as I was a rebellious
know it all, fifteen year old brat.

My parents were pretty good as far as parents went. I had not locked a
roof over my head, or enough food on the table, but I had always
resented the fact that my parents were not rich enough to give me
everything that I wanted. I knew in the back of my mind that this was
a pretty immature attitude, but what the hell, it was the way I
felt. I also di... Continue»
Posted by jayymie 2 months ago  |  Categories: First Time, Shemales  |  Views: 3783  |  
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Abused as a tranny at a sex party with my mum

This story is a follow up to "Caught wearing my mother's stockings"

I decided to go to the party and be the tranny slut they were looking for. After all, it's nice to be wanted and I really would do anything to keep those photos of me dressed in my mum's stockings, private from my friends.

I've never had anything up my ass before, in fact I've never even had sex at all. This was going to be my first sexual experience. Unless you include being wanked off by my mum or kissing and groping fat girl, Stacey Williams at the school Christmas party. So the idea of being the centre piece at a sex... Continue»
Posted by petearch 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 3773  |  
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My First Girly Cock

It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. I don't consider myself being gay, but I always had that ardent lust to be with a transsexual woman. I just couldn't get them out of my mind.

This passion started a couple of years ago, while I was surfing on the Internet looking for hot stuff. Immediately I felt something. That first time, when ... Continue»
Posted by jimpgr 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3769  |  
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Tina trap

A few days after he fucked me so masterfully that day, my friend's older associate invited me to visit him at his apartment. I wasn't sure what to do. Originally I had only had been with the one guy and now he seemed to be passing me on to his business partner. When I asked him about it he told me that he was OK with it. He had done this before: found a young guy and then introduced him to his older business contact.
So I had been used all along. I was just currency.
But I had liked how Mack - the older man - had fucked my ass. And I didn't want to NOT be fucked any more.
I accepted Mack'... Continue»
Posted by dlcalguy 9 months ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 3768  |  
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My shemale boss part 1

I knocked at my bosses door and on her reply went in. She was standing with her back to me looking out of the window and talking on the phone.

She failed to agknowledge me so I just sat down in one of the leather chairs opposite her desk. I looked at her as she stood by the window and perved over her black stiletto leather knee high boots and tight black leather skirt which covered her ass beautifully.

After about five minutes she turned to me, her black hair to her shoulders and her black shirt partly Unbuttoned showing off her cleavage, it has hard not to get a semi hard on as she move... Continue»
Posted by big_rob49 1 year ago  |  Categories: First Time, Shemales  |  Views: 3763  |  
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The mom who sneaks behind the door.

Hi im james and im 20 years old my mom is in her 50s with a larg rack big booty thin tight abbs and long smooth legs blue eyes and long hair aways weres pantie hoes and skirts and coresets and long red hair.
any way I was on my way home from school at night i got home mom was a sl**p i was on my lap top looking up porn watching this black chick lick a nother chicks ass hole i turnd all the lights off and started rubing my cock.
but as the black chick licked the other chick ass she moand so load some wan els came in will there eyes wure closed she was wearing a skirt and coreset.
she was bla... Continue»
Posted by gothicslave 1 year ago  |  Categories: BDSM, Lesbian Sex, Shemales  |  Views: 3749  |  
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My First Night of Being a Sissy Cumdump

Well I first started dressing when I was about 14. One thing that I always noticed is that putting on slutty clothes makes me an absolute whore for cock and cum. Throughout High School I dressed in my alone time but never acted on my slutty urges from fear of being caught by my parents. When I moved to college that all changed though. As soon as I got settled into my private dorm room, I thought it would be nice to spend the evening dressed like a little slut. I decided to wear my schoolgirl outfit that night. So I took a nice hot shower and shaved myself smooth from the neck down. I went back... Continue»
Posted by cumslutchloe 10 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3749  |  
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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 perfect

i 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 very horny and i soon found the 'blue doors'

in one of the doors was a gorgeous shemale from braz... Continue»
Posted by onceuponanas 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3742  |  
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What If My Mom Part 2

Peggy and Me

We all lay together for a while until Mom told us she had to get up, it was lunch time. We had not heard from Bobby or Dad and I was getting hungry. "You two just stay here, I will make some sandwiches. Back in a minute"

Just as Mom left Peggy rolled onto her side facing me, "That was so nice kissing your Mom.........., will you kiss me, down there?".

My feelings were still mixed up, but I did want to. I could show her what Mom had taught me. When I moved to get between her legs she stopped me. "No together, I want to suck your cock at the same time, you know".

Peggy p... Continue»
Posted by chchboy 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 3731  |  
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Meeting with the Boss

I arrived to work to find out that my boss wanted a meeting to discuss my future with the company. I wasn't sure if this was good or bad. My boss, Erica, is a very beautiful woman. She is hispanic with bronze skin. She resembles Eva Mendes and is about 5'7" tall, 130 lbs with great curves. She always wears tight skirts and blouses. I entered her office and she told me to sit. After talking for about 20 minutes I was thinking this is good because I would have been fired immediately.

She then asked me how dedicated was I to her and the company. I said very dedicated and that I love working he... Continue»
Posted by swordlvr69 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 3730  |  
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Caught by a neighbour in my s****rs clothes.

It was 10 o'clock on a Friday in late June of 1997. My parents were away visiting relatives for a few weeks. My s****r Kate had gone out partying with her friends for the night and wouldn’t be back till Saturday morning. Which left me all alone in the house.

For as long as I could remember I always loved dressing up in my s****r's clothes. When I was lucky enough to have a whole night with them out of the house, I usually went all out in my s****r's room. ??
I had been shaving what little body hair I had for years. I used to lie and tell anyone who noticed that a lot of swimmers and athlet... Continue»
Posted by kara_zor_el 3 years ago  |  Categories: Shemales  |  Views: 3713  |  
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foxxiroxxi gets fucked by a black bull at a costum

I was invited to a costume party by a good friend of mine named lexi , she has been my friend since we were k**s and knows i love to dress up as a women from time to time so she invited me and i accepted . The theme of the party was tight and short so unless you had the dress code on you dont get in . Lexi and i had to go shopping for new outfits to wear , we head straight to this dress shop that only has sexy club wear and dresses that only just cover your privates which was exactly what we wanted . Now both us were going to this party looking like two girls that wanted nothing more than cock... Continue»
Posted by foxxiroxxi 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 3711  |  
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It doesn't get any better than this!

15 years ago, I went into my older b*****r's room to grab a porno mag. He had stacks of them all over the place. I wasn't too choosy. I picked the magazine off of the top of the pile that was closest to his bed and went into the bathroom. My usual routine was to open the mag, find a babe, pull out my cock, and have at it. When I opened the mag, my jaw dropped and my dick got so hard, so fast it practically popped out of my pants! I could not believe what I was seeing! It was a gorgeous babe alright, but she had a BIG hard-on where her snatch was supposed to be! My cock was pulsing in my pants,... Continue»
Posted by bugaboobed 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3703  |  
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