Shemales Porn Stories
Page 16

More dirty adventures with Susie

This story is a sequel to my story "A story-tribute to Susie," where I write about how I really, really want to fuck XHamster user soeager2.

While being in Boise for two weeks on company business, I tried to make time as often as I could to get together for some hot times. Susie had some limited availability and we could only spend the most of two Friday afternoons together. She also came by the office all dressed up so we could sneak off to a nearby hotel for a lunch-time fling at a nearby hotel a couple times during my business trip.
Like all good things, it had to come to a... Continue»
Posted by 247hornyboi 5 months ago  |  Categories: Hardcore, Masturbation, Shemales  |  
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Gangbang at Ricks part 2

Gangbang at Ricks part2
Don said were here you sexy slut, helped me out of the car, grabed my butt arm around me like he was showing me off look what i have for the party, opened the front door Rick and 6 of his buddies with just shirts on, a few of them stopped sucking. Everthing got quite for a min. when Damn our Hooker is over dressed, who's first, I should have tape measured it was close to 90" of cock all for me? The party just started. Sex music, some guys saying Danm, good head, I know I should have tryed getting my cock sucked by a guy, years ago, as we walked in to the front roo... Continue»
Posted by mrheat22 5 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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The Making of a Sissy (Part 2: The Metamorphosis)

As the morning rays of sunlight pierced through my bedroom window I was awakened from the most intense dream, reenacting what had happened the night before. My throbbing hard little cock was gently humping against the sheets of my bed while I couldn't stop thinking about the amazing big black cock I had in my mouth just hours ago. I could still taste him on my tongue, and I could smell him on my lips. What had happened to me? Why was I so turned on by all of this? I thought to myself, "Maybe it was just a one time thing, like a one night stand." My mom had been dating a lot lately, so I ... Continue»
Posted by briantid8 5 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Kitty got caught - in college!

I love risky sex. I like to humiliation. I like to be treated as a useless piece of fucktoy for real men’s pleasure! I love the thrill in sex when there are chances of getting caught or something else that pushes me. So how did I figure that out?


Dressed in lingerie and wearing pink lipstick in my college, kneeling on the floor beside the toilet, waiting for the door to open, my mind kept going around in circles to what led me here, wondering if I could have done anything different to prevent it.

I remembered sitting on the toilet earlier today looking at my bright pink nylon and whit... Continue»
Posted by CumLovingKitty 5 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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Jamaican Dick for Chub Bottom

Renald Gold drove his s****r’s blue 2012 Toyota Rav4 down the highway. The five-foot-nine, one-hundred-eighty-pound Jamaican had arrived in the U.S. only days before. He thought Texas was pretty cool for the most part. He was especially happy that a pretty young sissy had hit him up on Tagged. They conversed back and forth for the better part of the day.

Prentiss Lewis was at home in the bathroom getting ready. His parents both worked the overnight shift at their respective jobs. He was an only c***d. The five-foot-eight-inch, chubby, dark-skinned dude douched his boipussy out. Prentiss was... Continue»
Posted by faggyboi 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Playtime Stories Ch 13 - Unbelievable Motel Reward

Ok, so this one is hot, but is mostly fantasy...I have 'earned' a few nights kinda like this though...
13.

I also fuck the hotel managers of another city. To be able to come and go all dressed up without anyone noticing is usually very important. Sometimes my company will have me stay at a premium ‘nice’ hotel. So I’ll get a slightly less nice motel on the side so I can do what I want without having it get back to my boss. A little caution and a few extra expenses go a long way.
One of the cities I go to on a quarterly basis can be a lot of fun. I’ve had some fairly hot times... Continue»
Posted by 6988slutty_rbckyy 5 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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Playtime Stories Ch 14 - Masters and Subs Stop by

As with the story line of Ch 13, this one is mostly fantasy except the Master Titan and 'Hole-boy'. They are people I met but couldn't play with (yet).

14.

I stood up and tucked myself in almost making myself cum in the process. I looked at him with a quizzical expression as I stood and walked to the door, wondering what I’d gotten into. I asked him if he was sure it was safe. He said I was in no danger and everything was going to be fine.
I looked at myself in the mirror to see that my makeup was still fine, despite my phenomenal cocksucking. I still looked a cheap whore with... Continue»
Posted by 6988slutty_rbckyy 5 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Playtime Stories Ch 11 - Carla the Theater Whore a

11.

After I was done stage fucking the nice-tiitted dirty-blonde school girl in her thirties, Carla had lined up some more meat for us. She’d been “working” the crowd while I had the blonde bent over on her knees. Carla and I sucked off about three more cocks each before the crowd waned. It was late. Carla offered to take me to her place and although I really wanted to go, I had to make sure I made it to my meeting on time in the morning. I knew it was past three o’clock in the morning.
We compromised because we knew we both wanted to fuck each other. We’d both been sucked and fu... Continue»
Posted by 6988slutty_rbckyy 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Break Down

Pu-Pu-Pu (Cough). Rattle. Hisssssss. Bang!

Robynn's car gurgled and grumbled, slowly crawling along until finally coming to a complete halt.

"Uggg . . . Not again!!" Robynn teared up in frustration. "Not now!" With all of the burdens she was currently carrying this was like the straw that broke the camel's back. As would be expected with most Sissies, Robynn wasn't mechanically inclined and had no idea what was wrong with her car. All she knew was that she was stranded in the middle of nowhere.

Honk! Honk! Honk! vehicles were expressing emotions since she was still in the middle of th... Continue»
Posted by amberfemxd 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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The Making of a Sissy (Part 1)

It was the summer after graduation, and I was living with my mom who was recently divorced. She had been dating a lot during that period, which was kind of rough for me to deal with. I would usually give her dates a hard time, and to be honest I was completely unsupportive of her decision to be dating. Anyhow, I was up late one night watching something on t.v. when I heard her and her new boyfriend come home from a date. They were apparently somewhat d***k and making a lot of noise, but I just tried to ignore it. It wasn't much longer until I started to hear this moaning and rocking of th... Continue»
Posted by briantid8 5 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Kneel, Suck, Swallow (Part Two)

"My, you're having a good time," said Patricia after our first guest had left. "Oh, yes!" I agreed, "But I am hungry for more." "Good," she said, glancing down at her cell phone where she had been texting with interested guys all evening. "The next guy should be here in about 15 minutes." I went into the bathroom to freshen up and apply more lipstick to replace what had come off my lips.

Soon there was a knock at the door. I took my position cross-legged on the couch while Patricia answered the door. This man was older than the first inexperienced guy, probably in his late twenties or ea... Continue»
Posted by kinkyjodigurl 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Panty Fantasies - Coleen's Magic

Sissy - body change – panties – satin – feminization – lingerie – cocksucking – gender swap

He swallowed hard, his body tense with anticipation and admittedly a small amount of fear. He didn't _really_ know this woman and her beauty was no guarantee of her honesty. He was exposing himself as he had never done before, all in a desperate attempt to capture his dreams, to experience the most intense pleasures.

Looking around the bathroom he saw that it was finely appointed with grey and pink marble and fine Italian tile. The towels were Egyptian and felt wonderful. The whole penthous... Continue»
Posted by naughty_bi_interest 5 months ago  |  Categories: Anal, Fetish, Shemales  |  
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Cupid’s Arrows

Cupid’s Arrows

copyright 2016 Brianna Luid

Lori, a 56-year-old, portish, balding, closeted cross-dresser was chair dancing in front of her computer screen and webcam, joining the other dateless gurls in the chatroom on St. Valentine's Day Eve. A lot of gurls were drinking and had turned on their webcams, so the evening had become a sort-of “lonely hearts” impromptu party.

She wore ballet slippers over black tights. Her pink and black mini-skirt was adorned with sparkly pink hearts and fringes. Her sheer pink blouse showed off her boobs, cradled by a pink shelf bra. Lori had done her ... Continue»
Posted by prairieFreak13 5 months ago  |  Categories: First Time, Shemales  |  
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THE INITIATION OF CARL

We were the cool guys in high school the ones everyone wanted to hang out with because to be seen with us was to be cool yourself…
The leader of our merry band was named Spike he got that nickname because once when he was jumping a fence he slipped and fell on a piece of rebar it impaled his upper thigh just missing his main artery we all freaked out but not Connor he just said “Oh Shit!” and lifted himself off that bar with bl**d pouring out of his leg we put his belt around his leg to stop the bleeding while we waited for the ambulance to come and of course we were making jokes about it say... Continue»
Posted by laceysgirl 5 months ago  |  Categories: Anal, First Time, Shemales  |  
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Tits Have Benefits

transgender – crossdressing – shemale – transformation – feminization

So there I was walking up to the most gorgeous creature in the room, a beautiful woman with incredible tits and ass and beautiful long black hair. This was the woman of my dreams who despite being the person who I could most open up to, nevertheless had been unobtainable in my mind. I had been a shy retiring nerd who could never hope to win the affections of a beautiful woman, but now things had changed and now I felt confident, because now I was a beautiful woman myself.

The story began six months ago.

My na... Continue»
Posted by naughty_bi_interest 5 months ago  |  Categories: First Time, Fetish, Shemales  |  
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Mrs. Thompson

Mrs. Thompson


It was a friday morning and beautifully sunny too without a cloud in the sky. I pulled into Mrs. Thompson's drive-way ready for what should of been half a days work flooring out a loft space. I parked up and rang the doorbell thinking about getting this job done quick so I could have the rest of the day off.
A beautiful lady who I assumed was Mrs. Thompson because I had only spoke to her over the phone, answered the door. Now Mrs. Thompson was at a guess, early thirties and around 5'8" tall with long legs, a nice lean body and shiny dark hair that fell just below her sho... Continue»
Posted by Davey76 5 months ago  |  Categories: Anal, First Time, Shemales  |  
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Lilith the 8mm Shemale Queen

(This was written after viewing Lilith's (fetishmy) video "A Rapid Cumshot. the way it is shot it looks like an 8mm film you would see in the old-time smut booths of a dirty bookstore)

I have an interest in the XXX world from the 40's 50's 60's 70's. Porn back then was not easily of accessed like today from the internet. the difficulty to get ahold of a dirty picture, magazine or film made it a prized possession. Today there is so much that it is rare to find a truly erotic person. One that exudes eroticism as much as exhibits it. Lilith, you are a truly erotic, sensual person.

In the ol... Continue»
Posted by cumjunie700 5 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
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kate monday continued

Do you mean go out now I asked
Yes why not Kate asked
I told her I was nervous!
OK do you like the way you look
Yes I replied
So stop being silly , let's go
We stepped out onto the street, the first thing I noticed was the cool air going up my skirt, also the way my tights held everything in on place,
I found it a huge turn on
We walked onto the high street looking in shop windows, sally pointed at a dress in a charity shop window , do you like that Christine

It was a king fisher blue satin dress, I nodded
Let's go in
I had a choice follow them in or stand outside on my own fee... Continue»
Posted by sissychris 5 months ago  |  Categories: Anal, Lesbian Sex, Shemales  |  
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Kneel, Suck, Swallow (Part One)

On a cold Saturday night a couple of Decembers ago, I was feeling very antsy and restless. I had just shaved my body, applied lotion on my arms, legs, and smooth white ass, and was trying on some sexy fishnets when I got a call from my Filipina ladyboy friend whom I had not seen in a while. She wanted to get together and have some fun. Not ever knowing what to expect, but knowing it would be something exciting and kinky to warm my body on a chilly night, I agreed to go to her house. "Give me an hour to get dressed and ready, and I will be right over," I told her.

So, after thoroughly cl... Continue»
Posted by kinkyjodigurl 5 months ago  |  Categories: Hardcore, Shemales  |  
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The urge to go to an ABS


The urge to go to an ABS soon popped into my head and to further add to the excitement, to go as a guy, but dressed underneath. To those you who go to an ABS, dressed underneath, I'm sure you can relate to this.

The first time I did this I wanted to suck a cock....like to good gurl should. After all, what's the point of dressing as a slut and not being one...and when I dress as "Jolene", I AM a slut. This was, may be, 12 yrs, ago. I told work I was on jury duty and planned the whole day around, getting dressed, going to this one ABS and actually sucking a cock and watching porn.

The on... Continue»
Posted by keripinkpanty 5 months ago  |  Categories: Shemales  |  
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