Shemales Porn Stories
Page 59

Afternoon Delight.

AFTERNOON DELIGHT.
Just a brief insight into my rather naughty afternoons.

I usually have a nice warm shower and shave my legs armpits and pubic area. With growing excitement I then I lock all the doors and close the curtains. Back in the bedroom I open my bedroom cupboard and pull out all of the boxes and bags containing my heels, hose and lingerie.
First I select a brand new pair of nude Aristoc Ultra Shine sheer to waist tights. I break the seal and slide out the plastic envelope containing the new unworn, ironed tights. I then break the inner seal and gently float out the new she... Continue»
Posted by pennypantyhosed 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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The Transformation part III

Since Mistress Anna had left me to sl**p with a vibrator shoved in my sissy hole It took a great deal of time before I decided I had had enough of the pleasurable sensation. It was long after she left that I actually slept. Despite the handcuffs and lease I found I slept amazingly well. Surprisingly being locked away in chastity was far from my mind. Then I woke up.

I felt someone step onto the couch where I was laying. When I opened my eyes all I saw was black and realized my eyes were covered. My head was grabbed and I felt a hand guide me to a lowering pussy. The taste said it cle... Continue»
Posted by fictiong 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
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LADY SUKI

It was my best friend who dragged to this little club downtown promising something I had never seen before. It turned out to be a little strip club. We found a seat right in front of the stage and we watched strippers of various shapes, sizes, and ages perform with a bored mechincalness.
"And now our feature attraction...." began the disembodied voice of the DJ.
"This is the one," my friend said, jabbing me in the ribs with his elbow.
"....let's have a big round of applause for Lady Suki."
From behind the curtain steps this amazing Asian girl whos... Continue»
Posted by slappywag64 5 years ago  |  Categories: First Time, Shemales, Taboo  |  
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TOTALLY DOMINATED

I was out walking one night, a walk i used to make with my girlfriend. We had just broken up a few days ago. I don't know why I was walking here again, the memories weren't good ones. She had cheated on me with my best friend. Anyways, I was walking this familiar path through the city streets when I met a very beautiful woman. She was tall and slender with bright red hair. She had a huge rack, at least a double D, and a tight sexy ass to match. Her name was Cherry. This has to be my lucky night I thought when she asked me if I wanted to hit the bars and so I agreed.

I spent the night going ... Continue»
Posted by LORDLONE 3 years ago  |  Categories: Group Sex, Shemales  |  
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I was Used








I Last night I went to an adult book and video store to mainly buy a new dildo to fuck my ass with.I found a nice 8" real looking one that had multiple vibrator settings and picked up a bottle of lube as well.I of course got sidetracked looking at gay videos and magazines as I held on to my new toy and lube.As I browsed the videos a buff looking obviously gay couple walked in.They were looking at videos and the different lubes.I would peek at them from time to time and smile....very hot....one was 6', blond, 30ish, without an ounce of fat on him...acted like the bott... Continue»
Posted by LSancho 4 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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My new carpool lover!

Good fortune smiled on me yet again this summer. If you keep your eyes and mind open, there’s no telling what you might find. At an office meeting a few months ago my company kicked off a carpool plan and the HR staff strongly encouraged participation. I figured I’d do my part by dropping my name & address into the pool database, but I had no intention of joining an actual carpool. After a few weeks I received an email from the pool organizer, saying that there was an opening in a pool group that lived in and around my neighborhood. Being the good guy that I am, I just ignored it of c... Continue»
Posted by ocmike 2 years ago  |  Categories: Fetish, Hardcore, Shemales  |  
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The best s****r ever part 3

As always yes my s****r is a shemale and yes this is all true every word of it.

So since we have formed our new relationship we have been fucking not stop for about 4 years now so im 14 and my s****r is 16 years old. I have now a thick 6" hard cock and my s****r has a huge 7 1/2" cock and we are both familiar with each others bodies but her breasts were so perfect, they were 32DD cups for a shemale.

Well it was a Thursday and both mom and dad said they would be working late which gave my s****r the grin I loved to see and I just grinned bak at her. We heard the door close and the car lea... Continue»
Posted by horndogs 4 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Shemale Assassin


Sarah was lining up a shot with her bow, preparing to take down the deer she had been stalking for ten minutes when there was a loud cry from the North-East of her hunting blind. The cry startled the deer, causing it to flee from the noise that permeated the forest.

"There goes a few meals." Sarah sighed with frustration.

Within seconds of shouldering her bow, Sarah noticed that the cry was actually a call for help and she made her way through the trees towards the screaming woman that was making it. In that area of the forest, it might have been a bear attack, bears being common enoug... Continue»
Posted by drew1207 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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Jake and sexy Tgirl Amanda were next on our "

So after we went out with Pete and Becky all day
Jet Ski's, Diving, and sneaking off for some impromptu blowjobs or a quicky, Alex and I decided that we'd ask Pete and Becky if they'd mind if we brought Jake and Amanda into our group. We described them to them, and they were hooked.

That evening at dinner Alex took it upon herself to make the first move. She sent over some drinks, and they came over to our table and that's where this story begins.


Amanda asked if we were swingers, when I spoke up and told her that even better than that, we're all bi swingers. Her jaw dropped and he... Continue»
Posted by SpicySide69 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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double date fun

It was just normal saturday when the phone rang.I answered it an my mom was on other end.She said can I ask you to do favor for me? I depends on what it is.Well she said, you know Cathy (moms lez lover) she called me and ask me to go out on date tonite.I yea so go, she said want to but her son just moved back in with her.I said yea don't he know about you two?Yes he does but we were wondering if you go out with him with us.I said well let me think,she said he very tall handsome an 46 yrs old.I said but does he know I am fulltime crossdresser? Mom paused a minute and said yes he does.I said ok... Continue»
Posted by cdpaula 4 years ago  |  Categories: Mature, Shemales, Taboo  |  
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Crossdresser drinks cum

Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she wanted me to pop, she'd plunge her head all the way down my pole.

Less than three minutes into the BJ, my cock disappeared into her face. I shot my load. Nikki froze while I unloaded. She couldn't say a word, but the bemused look in her eyes told me she was loving every second of it. I must've d... Continue»
Posted by MasterDavidsslut 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
2019
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Becoming the girl i really am....

I guess I'll start from the beginning, I was in my early teens and my parents had friends in town who we did everything with, travelling, camping, holidays, the works. They had a daughter who was a couple years older, and a son who was my age who was pretty much my best friend.

We started masturbating together in our very early teens, and since we were such good friends we were together a lot. One night i was sl**ping ove rhis house and while we were masturbating he asked "have you ever gotten a blow job?" "No" i said, giggling nervously as he slid right up against me in bedand slowly r... Continue»
Posted by dirtygurl4u 5 years ago  |  Categories: First Time, Shemales  |  
2018
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MANDY’S STORY (Memoirs of a T.V. slut)

MANDY’S STORY
(Memoirs of a T.V. slut)







Introduction
Chapter 1 -Early feelings.
Chapter 2 -Evenings in and nights out.
Chapter 3 -A slut in the making.
Chapter 4 -Bizarre encounters.
Chapter 5 -The Club.
Chapter 6 -A working holiday in Amsterdam. (Fantasy)
Chapter 7 -A video star is born. (Fantasy)
Chapter 8 -Out in the wilds with Uncle John.


INTRODUCTION

My name is Mandy. I’m a transvestite with a bit of a tale to tell. In fact I’ve had so many adventures had I’ve decided to share them with you by putting them down in this book. But first, a bit a... Continue»
Posted by mandydaniels23 1 year ago  |  Categories: Anal, First Time, Shemales  |  
2018
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My New Lover!

I was still testing the waters a bit. I went out in my skinny jeans and just a t-shirt (I still don't crossdress in public at least not heavily, still uncomfortable), my slightly long hair makes me look very androgynous. I wear very subtle eye makeup as well, I am happy in my body, it suits being a guy for my job and a girl for my lover. I thought I liked him a little but by the time we made it back to my house, which was empty, an irregular occurrence, he had been very nice and hit on me a little. He complimented my body and my ass (not to stroke my ego but I love my ass, I get compliments on... Continue»
Posted by bisubtaylor92 7 months ago  |  Categories: Anal, Gay Male, Shemales  |  
2016
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He Got Used and Didn't Mind. (Part 1)

I am getting back into the habit of writing stories. As I have done in the past physical features of characters are left to the imagionation. Please comment on this if you like to let me know when I need to write part 2.

Dave met Jesse online and they kicked it off well due to things they have in common. Since they lived in the same city they decided to meet in person at Jesse's place. Dave had been working side jobs and told his wife Lucy that his new friend Jesse wanted to talk out some jobs he may have available, and off he went.

Once there a conversation took place about common inte... Continue»
Posted by mrman1982 2 years ago  |  Categories: Sex Humor, Voyeur, Shemales  |  
2013
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Settling in with my new RoommateHe

It didn't take very long for my roommate, Ed, to figure out that I was a submissive sissy slut. I think that Ed was basically a straight guy as far as his sexual orientation went but he liked the fact that, if he couldn't score away from home, a willing mouth and ass was always at home when he wanted it. Ed insisted that I wear at least a garter belt and stockings to bed every night. He said that he liked the way the garter belt "framed my ass" and he liked the way my stockings felt when I would wrap my legs around his waist. So, I would go to sl**p in my bed dressed in sexy lingerie and s... Continue»
Posted by rikki50 2 years ago  |  Categories: Gay Male, Shemales  |  
2012
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Met 2 s****rs with a secret part 2

Synopsis: This story is about a young man named Devon who is living abroad as he goes to college. In the previous installment, Devon meets Asha and Shanthi - two half-white, half-Sri Lankan s****rs who live in the apartment next to his, and they begin an immediate friendship. With Asha, that friendship becomes more after Devon discovers that she is a transsexual. After their first night of passionate sex, Asha tells Devon that they must keep their relationship a secret because her s****r Shanthi is in love with him, and Asha fears she has already betrayed her s****r by sl**ping with him. But D... Continue»
Posted by drew1207 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
2012
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Sexy show

One night I was at a friends house with a few people playing cards. The whole time watching my friends wife sit in front of me in little shorts and a shirt that showed her big tits when she bent over. I was so horny that I snuck in her room and went thru her drawers so I could grab some panties and a couple bras. I found a sexy leotard swimsuit, pantyhose, tight sheer shorts, and a skirt. I went to the bathroom and put it all on under my clothes then I left. I was so turned on in her clothes that I took my clothes off and I wore her white bra, a hot pair of her thong panties and put on her p... Continue»
Posted by droger709 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
2008
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Long Distance Cr*!gslist Charity

Through the stresses and demands of everyday life, I had found myself becoming evermore restless being alone after loosing Frank. It was coming up the five year anniversary since he passed. I had been looking on Cr*!gslist infrequently in search for a possible new partner. Often find men who are married seeking a play toy on the side, or those who want a gurl with a dick to suck, and bend over for. While in the world of alternative love, passion comes in far more than 32 flavors- that's not what I'm seeking. After realizing that the local ads are little more that the same handful of horn... Continue»
Posted by gurlinpumps 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
2008
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A used sissy

“This one right here” Bob said. “This little sissy is perfect!” Bob and his two friends had spent the last few weeks scouring Craigslist personal ads for a small transvestite that they could take advantage of. “I’ll email the cunt with a pic of my nine inch cock – see if she bites!” Bob said. Sure enough a day later, the TV named Debi contacted Bob with pictures of “her” own. Bob shared the pics with his friends. “Look!” Bob said, “The cunt could pass easily, and the sissy even has little sissy boobs! Oh, this is gonna be fun! ” They all agreed that Debi was to be the one.
Debi had said in... Continue»
Posted by tvdebi 1 year ago  |  Categories: Shemales  |  
2008
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