Shemales Porn Stories
Page 15

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: 3827  |  
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Sissy Cum Slut Stephy

I have been cross dressing and playing with men for many years now. One of My first experiences being gangbanged by an unknown amount of guys was at a book store. I was about 18 at the time and it kind of traumatized me as it was pretty much a gang fucked. I was dressed up in a white sundress with lace top stockings and white strap on high heeled sandals all borrowed from my older s****r. I had my make up done up just right and looked great. I have long blonde hair and was dressed to kinda sexy and all keyed up being out dressed in public so I decided to go find a guy for some Sexual explorati... Continue»
Posted by SissyCumSlutWhore 3 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 3824  |  
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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 4 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 3820  |  
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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 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 3817  |  
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Tranny, Wife & Me

I have always loved sex with trannies, even more than sex. Friendship and closeness that I would struggle to fin in a guy. My wife had no huge preference for Tgirls but she did have a ravenous appetite for sex and was curious enough to try everything. We decided to go to Manchester and their regular Saturday night Tranny evenings and from previous visits, we had a few drinks in Napoleon's Lounge. It was a popular meeting place for "girls." Trannies who liked other girls, trannies who preferred women and girls who were seeking for the ultimate tranny accessory - a boyfriend who would take the t... Continue»
Posted by totallyurs 29 days ago  |  Categories: Anal, First Time, Shemales  |  Views: 3816  |  
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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 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3804  |  
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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: 3798  |  
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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 1 year ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 3794  |  
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CD at truck stop with three men

Went to a truck stop last night after a party around midnight in my sexy short dress, got out and bent over looking at my tires for assistance. Gave a nice view to whoever was watching of my smooth white ass and sexy black panties with pink trim with half of both cheeks exposed. A nice older (63 yo) black guy (Ted) asked me from his truck if I needed help. We talked and then thanked him and asked if I could help him for helping me.

We walked over to his truck and got in his sl**ping quarters. Gave him some more intimate show of my nice ass, turned around, unzipped his pants and began ... Continue»
Posted by hotcdsub 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3785  |  
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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: 3776  |  
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First time with Brooke.

A few years back I lived on the 2nd floor of a four-flat apartment. Downstairs from me lived Brooke. She was an attractive girl, about a year older than me. We were both divorced at the time and she knew I spent most of my nights alone. She would often invite me down for dinner and vise-versa. Other times we would hand out in each other’s apartment watching TV and talking. I liked her but I didn’t feel that she was interested in me. Plus, she had a boyfriend at the time. He was the athletic type that worked in the corporate world. She really didn’t talk about him too much and since he lived do... Continue»
Posted by ahsleymills 4 months ago  |  Categories: Fetish, Shemales  |  Views: 3775  |  
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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 was visible. My boss, Terry, a very pretty, sexy lady (who I later found out was a hot-bod t... Continue»
Posted by freegre 4 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3780  |  
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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: 3773  |  
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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 9 months ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 3771  |  
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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 2 years ago  |  Categories: First Time, Shemales  |  Views: 3765  |  
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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 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3752  |  
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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: 3735  |  
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Wife Shares Shemale

"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 drew1207 7 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 3727  |  
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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 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 3726  |  
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Date with Young Katie

Fun with crossdresser Katie


So here I am browsing online ads to see who is out there that may be interested in meeting up for some safe adult fun. Lo and behold I’d come across this ad online that I’ve saw before of this young 27-year-old cross-dresser. Other times I was unable to meet with this young thing because of my work schedule so I never answer that ad. I said to myself here goes. I to put a few more pictures in the e-mail, cock, body shots and see if I get a response. I received a response from this young hot, sexy cross-dresser. Wanting to know whether not I was real and serious... Continue»
Posted by JUSTLO 2 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3714  |  
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