Shemales Porn Stories
Page 9

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 3 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 3 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 3 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 3 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 3 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 3 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 3 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 3 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 3 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 3 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 3 months ago  |  Categories: Shemales  |  
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My Journey part 2.

My Journey part 2

Up until this point in my life I was quite inexperienced in sex with women and men never even featured in any fantasy let alone real life and at that time I did struggle with guilt and shame but one of the good things about being a young man was that these doubts and guilty feelings were quickly forgotten or justified as soon as we get turned on and or got a hard on, with Matt moving away in a few months for a new job we both had very little time to explore and play so we began playing hard and fast in all sorts of kinky ways, the only thing new I had brought to the table ... Continue»
Posted by silknsatinxxxx 3 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Kitty's hitchhike

One Friday I went to the local shopping center about 5 miles closer to our home. I did some shopping and had a late lunch at a restaurant. But as soon as I got out, I came to know that some VIP has been murdered and there is a sudden transport strike. A 3 mile walk was no big deal for me if I had to. I started walking and putting my thumbs out hoping for a ride. Soon I was picked up by a guy who was noticeably older, driving a real nice older car. He said he could take me to the intersection near about 1 mile from my home and I would be able to walk home from there. That was fine with me. As h... Continue»
Posted by CumLovingKitty 3 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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Kitty's emergency service

A friend of mine once told me that he knew a great guy and gave him my number. Soon I received a message. It was from a 23 year old college student named Mohit. He was going to college in the next town, said he was packed just over 7 inches, and sent a pic that made it look like he had a telephone pole sticking out of his groin. We traded a few emails and next thing I knew I was over to his apartment. I was kinda nervous when I knocked on his door but that went away when a good looking guy opened the door. He introduced himself as Mohit and invited me in.

"You want a beer or something?" Mo... Continue»
Posted by CumLovingKitty 3 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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I Knew I Was A Sissy (part IV)

It was the very next day that the guys asked me to join them. After dinner we went to their cabin where Mary was waiting for us. I was not feeling comfortable not knowing what will happen. Mary looked at me and smiled, she told me not to be stressed and relax. Then she asked Ethan and Peter to leave, we were to join them later at the beach as she said.
We were now alone in the cabin when she came close to me and whispered: “I will transform you to the most beautiful girl ever”. I was excited as you can easily guess. She took a makeup set off her bag and started. About 40 minutes later I coul... Continue»
Posted by georgette32hk 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Pillow Fight

Five little Sissies laughing and giggling like goofy teenage girls exchanging recipes, sharing makeup tips, Omigawshing about everything, and who knows what else. Wandering around in the gossip garden . . . Planting new seeds, indeed. A night, tonight together. Funzies. Sissies only. No! Men! Allowed! Grrrrrrrrr. Purrrrrrrrr.

SPLAT!

And the slumber party begins. Aspen, Ginger, Peggy, Sarah and Jennio awkwardly trying to battle it out on a large king sized bed.

Here comes another fluffy pillow . . .

SPLAT!

The little sissies were being soooooo silly.

SPLAT!

Another pillow a... Continue»
Posted by amberfemxd 3 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Where She Wants Me.....

I love to write. In fact, if I could make a real living at it, that would be my preferred career choice.
However, writers block, deadlines, overall motivation, and my "other," career choice, have thus far anyway prevented me from doing so.
Hence at the moment anyway, it remains a hobby to be indulged in whenever the Muse strikes me.
This work is one such moment.
I hope those who read it will enjoy it, and be kind in critiquing it.
Constructive thoughts are always welcome and appreciated.
Mean spirited jabs obviously are not.

Where She Wants me:

Immobilized, that's what I was... Continue»
Posted by bottomboi4u 3 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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Pantyhose Kink In The Park

Pantyhose Kink In The Park


I was extremely horny one day, and I hadn't been to a public park in a few years, so I decided to get dressed up under my clothes, and try my luck at a local park that the locals referred to as the "Pickle Park". I know that they are around in every state, but this one was very interesting. It has an incredible amount of woods, and it was full of trails that went deep, and winded around so there were many private areas to have fun. This park in particular, was known for the amount of dirty old men that went there, so I decided to pay it a visit.

I pu... Continue»
Posted by silkslipsandhose 3 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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My First Tranny

Cheryl had really opened my desires to fuck. She was, and is totally uninhibited, and a total sex machine, doing whatever she desires at the moment. When I felt my cock enter her throat the first time, and felt her tongue slide up my cock to the balls, and she sucked the cum right out like my urethra was a straw, I knew I had a keeper. I was hoping I was able to satisfy her, and hoping she would keep me around, this was really the best sex ever. I would get no argument from my wife, she was getting all the cock, and later I would discover she was getting pussy also, she had the best of it ... Continue»
Posted by fishkiller 3 months ago  |  Categories: Fetish, Mature, Shemales  |  
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Gangbang party at Ricks part 1

This weekend, Rick my b/f had a poker party, more like a poke her gangbang 6 of his horn dog buds had a female hooker she had a nice 200 cash out there, well she chickend out at the last min. she heard about the cock yes 8" to 12" and she diddnt want the money , said to rick no way, and who she was, OMG she was young n hot and we knew her. found out it was later.6pm no one there yet, everyone knows he is BI his buds did to. So he called me and said His party was a bust he needed a sissy slut like me. we did not have Cell phones 8 pm time to party. well my fantacy he told me be ready just... Continue»
Posted by mrheat22 3 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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