Shemales Porn Stories
Page 70

The Booty Inspector of the Old West (pt. 3)

The Booty Inspector pt. 3 by markfayer

“Freaky Felatio Foursome”


Dick and his intrepid Lieutenant, junior, had no sooner arrived at the Barnaby’s Circus Fairgrounds when they spied the performers’ ring of campers set about in a cozy circle, creating a small common open space for the freaks and Acrobats and other members of the Freak Parade.
“Alright, Dick, what’s our plan of Attack?” quipped Junior.
“Well…I figgur we just waltz into the Boxler b*o’s trailer, give them an offer they caint refuse—by which I mean they get to fornicate with our Nubian Amazons-in-tow in a no... Continue»
Posted by markfayer 2 years ago  |  Categories: Interracial Sex, Sex Humor, Shemales  |  
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Young Black Motel Stud

I placed a personal ad, something along the lines of “Sexy, slutty, white CD looking for horny black man”. Much to my chagrin, I got little in the way of a decent response (I placed the ad kind of late in the day on a Saturday). Anyway, I spent the afternoon doing a full body shave, bubble bath, etc. so I could be ready for an evening of fun, if it were to happen. Around 10:00 PM, figuring I was out of luck (You should have seen the lame responses I got), I decided to head out to a local sports bar for a few drinks. Hoping I would get a late response. I made sure I had my clothes, makeup bag, ... Continue»
Posted by cdncleggs 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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First time dressing up: Part 2

Dressing in my s****rs clothes became a regular thing after about 2 months of doing it, I would use her vibrator on my ass at least once a week. My f****y was gone more often so it gave me plenty of time to prefect doing my make up, hair and shaving my legs. One night when my f****y WAS home i was looking for a pen to write a card. I went too my parents room to look for one and on my step mom's dresser was a small blue key, i had no clue what it would go to and for some reason it seamed important. I put it back and continued on looking for a pen

Two days later my f****y was i out so imminen... Continue»
Posted by Badassgirl123 2 years ago  |  Categories: Masturbation, Shemales, Taboo  |  
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Marie's playtime: An evening with Susan

Marie woke for work like it was any other day, all hard and swollen, first thing she did was rub her smooth legs together. The silky feeling alone was enough to send a tremor of pleasure through her. Desperate to cum but conscious of the impending lateness to start her day she quickly dressed and assumed the guise of her male alter ego. This meant a grey man's suit, but before that went on so did a pair of 10 denier stockings and garter belt with a lacy mesh fronted pantie through which her cock was clearly visible, under her jacket she wore a tie and shirt, nothing to exciting.

Time passed... Continue»
Posted by Marie_metal 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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First time dressing up

I was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my s****rs clothes. I went into my s****rs room when the house was empty and opened up her closet. I saw all of her nice shirts, blouses and dresses, i looked around pulling some stuff out and eventually made my way to her dresser and saw all the panties and bras. I wanted so badly to try on a whole outfit but i was terrified of getting caught.

Then i got an idea. I picked out the clothes i wanted... Continue»
Posted by Badassgirl123 2 years ago  |  Categories: First Time, Masturbation, Shemales  |  
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My friend's new roommate and her surprise

So my friend Rebecca and I were planning on going to this bar for the evening but she called me and said she was running a bit late and that I should wait at her place and that her new roommate Shawna should be there to open the door for me. Rather, than wait in my car I went upstairs to her apartment like she suggested. The door was slightly open so I walked in saying hello; to see if anyone was home. I heard some noise in the kitchen so I walked over to check it out. It was Shawna cooking. She was actually a pretty cute girl. She was wearing a white tee shirt that just about covered her ass ... Continue»
Posted by lovingitman 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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Tgirl Hooker pt5

All my stories and based on my own experiences.

All other parts are on here and would recommend you have a read.

The next time I saw Emma my ass was still sore and I was quite bruised inside from how are she had fucked me, so we went for a curry and a few beers.

After Emma had been perved at all night by the staff and some older business men in the restaurant but I know she loved it, the cute little giggle she done, the way she would look at them and bit her lip, for all I know they could be clients of her's. The thing I learned was although I was her fuck buddy, I was still paying he... Continue»
Posted by dirtydisco99 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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Valerie on an Island


I’ve been here at the house for about a week. It sits on the side a hill overlooking a valley of trees and shrubs, some farmland, the nearest house is a half a mile away. The room that I’m kept in has a little window and it’s been breezy and cool with a bright sun almost every day.

It’s an old house and the walls seem to be two feet think in most places. That along with the metal bars on the windows gives it the feel of a cell, although a very nice cell. A large metal four poster bed, covered in silky sheets and pillows and a dresser and a large mirrored closet loaded with women’s shoes a... Continue»
Posted by subval79 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Tgirl Hooker pt4

All my stories are based on my experiences.

For those who may not have read pt 1 to 3, Emma is a Eastern European Tgirl hooker who I found online, Pt 1 & 2 are about my first experiences with Emma and pt 3 she told me I was no longer a client but a fuck buddy....

So after that night when Emma told me I was now her new fuck buddy, we spoke all the time and had been out a few times to eat and it always ended with us boozing and me picking up the bill. I was beginning to feel a little used by this as nothing sexual was happening and the money I had spent could of paid for a good few hours ... Continue»
Posted by dirtydisco99 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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angel encounter

We both work in Angel Islington, most days we catch the same tube. Most days we stand close on the endless escalator. Most days we leave the station separate ways We never talk, some times I can smell her shampoo and sometimes and I can barely see her. I know she watches me, but she never catches my eye.

Three days ago she did. Momentarily, if it hadn't been for the raised eyebrow I might not have noticed the look.

She walked off quite quickly, leaving me mouth open like a guppy. I regained my composure and followed her, keeping her in view. She glanced back at me, catching me leeri... Continue»
Posted by j0shr0gan 2 years ago  |  Categories: Hardcore, Shemales, Voyeur  |  
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shes the boss

This story is 100% true well as true as I can remember. This year I celebrated 40 years of marriage. I am 60 and she is young 68. We met on a mini cruise from UK to Europe. I say cruise but it was just overnight boat trip to Denmark a day there and overnight trip back. I worked in a factory and it was a works trip there. There was about 40 of us going. I was 17 and just started work there. She was 24 didn't work in factory but her mum did. I hadn't had much luck with girls and was very inexperienced, she on other hand had 2 c***dren one age 8 and one aged 5. She had got pregnant when she wa... Continue»
Posted by tvtv11uk 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
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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 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Appointment By Card Only. part one

She had always been so vulnerable, growing up with the other boys it was so obvious she was not like them. Now in their late teens as adulthood announced itself to the others by adorning them with bodily hair and a developing musculature, they laughed at the soft hairless form of the one who was well known to them, but only from an external perspective. The feminine tendencies peaked within her at this time; she found other boys strangely attractive, and something also stirred within the loins of most of those who were acquainted with the soft boy, though none admitted it openly. Now pretty fa... Continue»
Posted by midsummerman 2 years ago  |  Categories: BDSM, Mature, Shemales  |  
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Slut Bad Gurl on The Run

I checked into the motel with two suitcases, one for the traveling man and one for Victoria. Vicki likes to come out and play in strange cities where she can be herself in complete anonimity. She is a slutty, smoking sissy gurl!
I run the bath and put in some girlie bubbles. As the hot water fills the tub I unpack my sexy clothes, black lace bra and panties, stockings, waist cincher, 6" black open-toe pumps, and lay them out on one bed. I unpack my make-up and jewelry.

There's something so sexy about a seedy motel room!

The bath gets my skin all pink and girly and my clitty is ready for... Continue»
Posted by ignatzvictoria 2 years ago  |  Categories: Fetish, Shemales  |  
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First time glory hole part2

...... I woke up and the lights were now on so I was guessing it was night and they close this place at 12 so was hoping that the man who closes it down let's me go so I looked at my watch it was 11 so was hoping someone would come soon.

Someone came in I guessed it was the cleaner cos he went into the other stall and sounded like he was cleaning so I was hoping he will let me go he had finished cleaning the other stall and then open the door to the stall I was in he looked in shock to see me sat there with no trousers on after being shocked he looked round went to the main door and shut it... Continue»
Posted by briggs123 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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three gets crowded

I was over at a 'friends' house the other day. Just relaxing on the couch snuggling up to him watching TV. His couch is halfway between a full couch and a loveseat. He is also a fairly large older man (in his 50's, around 6'2" and weighing between 240-250). Just how I like my daddies :)

I was wearing a simple outfit. A nice colorful skirt that went to my knees and a simple blue tank top. Plain, but comfortable. He had one hand around me, and was running his hand across the skin on my arms when the doorbell rang. I quickly got up and answered the door. It was his friend 'Jim'.

... Continue»
Posted by zaria_ts 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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Tgirl Hooker pt3

All my stories are based on my experiences

I’m sure most of you have read The Tgirl Hooker pt1 & pt2 with Emma who I found on a well known website. Pt 1 & pt2 was about my very first meeting with this Eastern European beauty who had a body to die for and a cock to match. I used to get the odd text from Emma every now and again asking when was I coming to see her, which then led to us chatting a bit and then as I got to know her, we then started to text or chat online nearly every day. I bottled up the guts to ask her out for a drink... one where I was not going to be charged by the hour a... Continue»
Posted by dirtydisco99 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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The Portal Part 1

Figures streamed across Jim's screen, highlighting yet another problem with the accelerator. Dr Jim Smith was one year into his 3 year program at CERN and things were not going well. The results from the detectors were way off the predicted scale and Jim would have to delve into the machinery once more to ascertain the problem. "Pass my safety hat Stewie" Jim asked as he grabbed his tools from the case on the floor.
"Should I re-set the experiment Dr Smith?" asked Dr Stewart Jones, as he passed the safety hat to him as requested.
"Yeah, re-set it Stewie and we'll give it one more go befo... Continue»
Posted by dekkard69 2 years ago  |  Categories: BDSM, Gay Male, Shemales  |  
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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 2 years ago  |  Categories: Gay Male, Shemales  |  
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Bad Habits CD Fantasy

Why did I keep making bets like that, was the only thing I could think of while in line. Why did I keep making bets I was destined to loose, and then have outcomes like...well, this. I was standing in line to go to a cosplay convention, and was in full costume, but of the wrong gender. I was dressed up as one of those Vocaloids, with knee length blue pigtails, A black skirt that was barely at my knees, a set of black and blue boots that went up to my thighs, a sleeveless vest like shirt, a weird belt thing, weird glove-like sleeves (that left my armpits and upper arms open for the whole world ... Continue»
Posted by RosalynLee3 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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