Shemales Porn Stories
Page 14

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 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3797  |  
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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: 3782  |  
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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 2 months ago  |  Categories: Fetish, Shemales  |  Views: 3782  |  
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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: 3772  |  
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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: 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 7 months ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 3767  |  
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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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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: 3744  |  
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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: 3736  |  
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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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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: 3716  |  
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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 5 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 3716  |  
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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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this year Dr. visit

My Annual Dr'S Visit 2014

i guess I'll describe this years visit and if you like reading them I'll continue to describe my annual Dr. Visits. I've been seeing the same Dr. and his Nurse for about 4 years now. The first one was mostly normal however the last two previous ones have been kind of embarrassing for me and I wondered how this year's would be. I made my appointment and and as usual the nurse came to the waiting room and got me and took me back to the exam room. She had me go into the changing room to put on the gown . I took off my shorts and top exposing my bra and panties like ... Continue»
Posted by sissygirl 6 months ago  |  Categories: Gay Male, Shemales  |  Views: 3701  |  
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Bi male and anal sex

Thru out my adult sex life I have always enjoyed having my ass teased and played with. 
Then I started dating a woman whom loved to tease a mans ass with her fingers, yes fingers where she quickly got me use to taking 2 of her fingers. 
Then one night things changed. After a hot night of wild sex, she slowed things down before excusing herself. But before she left, she rolls me over on my chest, which to me means she want to tease my ass. I hear her in the bathroom , toilet flushes and I hear her returning to the bed, straddling my legs, she racks her fingers up and down my back before she l... Continue»
Posted by rogue-1966 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3699  |  
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TRAP

I was dating this 27 year old fox. And I was luvn it. You See Im 44 years old a lil overweight and I have a 5 inch cock! So you can imagine my surprise when I picked this little honey up at the bar d***k and the next morning she didnt want to leave!
The first night I got her home and we dove into bed Im 6ft 230 lbs with strong arms and long flowing hair We sucked each others tongues at first. I felt that tight body up and my lil boner was diamond hard. I got up to get her a liquor drink and I let my eyes feast upon this 5ft 8in beauty 115lbs of pure sin. She wore a size six shoe and had a bi... Continue»
Posted by playingroles 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3693  |  
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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: 3669  |  
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He caught me in his wife's cloths

I do odd job's and I was about to do one for my wife's best friend Tina and her Husband Phillip. I went over and looked at the job. I told her it would take several days and that I could do the work while her and her husband were at work. That way I wouldn't be in anyones way. Well the first day of the job I showed up just before Tina left for work. Pillip was already gone. We chatted a while the she left for work. Tina is really very hot and I have wanted to fuck her for a long time. Sense i knew that was not going to happen I thought I would do the next best thing. I went stra... Continue»
Posted by firstknightd 4 years ago  |  Categories: Shemales  |  Views: 3660  |  
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My New Girlfriend Turns Out to Be a Shemale.

Where do I start?
How about at the beginning. My name is Cal I am divorced and living alone. I am not a bad catch I am five foot eleven, short black hair, green eyes and no visible scars. I am a regular at the gym so I am in shape but not ripped. A seven inch uncut cock that I can use well. I dress nicely and have a good job.
My friends Don and Lisa were feeling sorry for me they knew how ugly my divorce was and how lonely I was so they invited me to their pool party last weekend. They said there would be some single women there and I might find someone I like.
Okay, I thought at... Continue»
Posted by triphammer73 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3656  |  
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Letting my neighbor see me jacking off!

Yes, i am lucky to have a hot neighbor, a guy who likes to watch me when i am outside, in the yard or even geting into my car, it seems that when i go outside, there he is! So, why not give him what he wants, whether he knows that i am a shemale with a hot 7 inch cock, or as he might think, a girl with a wet, pink pussy. I know he jacks off to me, i did see him in his upstairs window last month, shades pulled up, jacking his big cock off as i wa outside in shorts up to my ass. He shot a load on the window and i know he knwos that i saw it all. so? My turn! Shortly thereafter, i went outside in... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 3655  |  
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