Shemales Porn Stories
Page 4

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 1 month ago  |  Categories: Interracial Sex, Sex Humor, Shemales  |  Views: 273  |  
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best friend

my buddy and i had been friend from day one. we grew up together. played sports together. we partied all the time and both had women come and go. i had finally found a steady girl friend, but for some reason he could never keep a girl friend. "i perfer being single, play the feild." he would always say.

after being in a steady relationship we naturally started hang out less and less. and eventually months went by. one day i decied to pop in and say whats up. see how things were going. figured id suprise him with a six pack of beer and some pizza just to hang out like the old days. little d... Continue»
Posted by souljah89 1 month ago  |  Categories: First Time, Shemales  |  Views: 3047  |  
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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 1 month ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1838  |  
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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 1 month ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 1487  |  
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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 1 month ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1172  |  
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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 1 month ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 1669  |  
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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 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 7985  |  
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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 1 month ago  |  Categories: Anal, Fetish, Shemales  |  Views: 934  |  
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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 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3183  |  
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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 1 month ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1099  |  
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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 1 month ago  |  Categories: Hardcore, Shemales, Voyeur  |  Views: 993  |  
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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 1 month ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1530  |  
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The unusual girl...and boy: Part 6

Part 6: "A new beginning."

Sam was now 8 months pregnant and she had just turned 16 in july. The last time we went to her doctor for her sonogram was two month's ago and the doctor said it was gonna be a boy. Sam had to go get another one but this time the doctor also gave her some bad news, saying that since she was going to be having a baby, she would have to consider losing her under developed testicles. Without thinking it over twice Sam said, "Thank you for letting us know doctor... But I'm more than willing to cut my balls off myself for this baby, so that won't be an issue for me." I... Continue»
Posted by adblman 1 month ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 1106  |  
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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 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 4476  |  
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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 1 month ago  |  Categories: BDSM, Mature, Shemales  |  Views: 1406  |  
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The unusual girl...and boy: Part 5

Part 5: "What a party..."
(part 4's subtitle was "The discovery." Not "the disco", lol...)

Sam was almost two months pregnant and my birthday was coming up on Saturday. On Thursday just minutes before our class started, out of no where, Sam decided to talk to some guys in our class about my upcoming birthday and two of the guys on the other side of the class room seemed interested. Sam came back to me and said that we would all be meeting up at her parents house on Saturday. I wasn't expecting anyone to actually show up because we weren't exactly the most popular at our school. 

Saturd... Continue»
Posted by adblman 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 809  |  
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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 1 month ago  |  Categories: Fetish, Shemales  |  Views: 481  |  
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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 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3593  |  
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The unusual girl...and boy: Part 4 "The disco

Pt4:
I had unprotected sex that night with Sam for the first time and I had taken her virginity, also losing mine in the process. I was asle3p for no more than two hours I was lying next to Sam, both of us fully naked on her bed and we were suddenly woken up by her mom, Martha. I was shocked to see Sam's mom staring at us and she was then looking at the little spots of Sam's virgin blo0d on her bed sheets. Then Martha looked at my unprotected dick which was also semi covered in her hermaphrodite daughter's virgin blo0d. Sam's mom looked at both of us saying, "Oh my gosh! You two had unprotect... Continue»
Posted by adblman 1 month ago  |  Categories: Hardcore, Masturbation, Shemales  |  Views: 2592  |  
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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 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 3633  |  
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