Shemales Porn Stories
Page 75

Sissy boy and ... a shave

It’s a Saturday night. I’ve been talking with this guy online for a while now trying to determine if he and I are the right fit…. and also work up the balls to meet up (…so my balls and much more can be worked over). We’d spoken about a whole bunch of things whilst chatting, his fetishes, mine, and what both of us would like to do to the other / have done to us. From this it all seemed pretty enticing so we teed up a night we were both free to dedicate to debauchery. Thankfully for me my instincts were accurate when we meet, the guy hadn’t hyped it up, or just completely lied about what he loo... Continue»
Posted by littlebum85 3 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Part 1.. An Idea forms

My plan was pretty simple really… Find a fem-boi looking for a Sugar Daddy and change him to a her over a period of time… Simple in theory, Much harder then it would seem in reality. Being in my mid-40’s and rather well off from a few investments and a wealthy grand-mother I had plenty of time to indulge my more twisted desires. I got into Trans-Sexual porn a few years ago and I was hooked almost immediately. I do not think I am actually gay because the thought of ass fucking a man does nothing for me.. But on the other hand if that man had very feminine features, a small quiet voice, creamy ... Continue»
Posted by Azmodaz 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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The unusual girl...and boy: part 3

Pt3:
Saturday night seemed to last for ever and I couldn't sle3p for hours since I had just found out what it felt like to play with my butt hole when I was in the shower. My loneliness continued Sunday morning until I finally called her in towards the afternoon. When Sam picked up the phone and I heard her voice say hello, the first words that came out of my mouth were, "I'm sorry for doubting you Sam! It's okay with me, now we can do things how ever you want but please don't be mad at me!" She said, "You mean...you're fine with doing it my way?" I quickly confirmed it saying, "Yes! It reall... Continue»
Posted by adblman 11 months ago  |  Categories: Anal, First Time, Shemales  |  
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my last and favorite

it was 3 years ago .. id become close friends with a girl who had so many friends but she had trouble getting guy friends and when she did get boyfriends it never lasted long and i felt so bad for her. one night we were drinking and went to her house. i loved her and treated her like my s****r, but tonight she was sticking unusually close to me..soon we were kissing and later we started taking each others clothes off.. she soon saw that i was wearing my panties and saw that i was embarrassed in front of her.. she then showed me that she wasn't just a normal girl but a TV , but she never seemed... Continue»
Posted by drewcd 3 years ago  |  Categories: Group Sex, Lesbian Sex, Shemales  |  
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Delilah and the Deep Blue Sea. (part four)



The skipper of my boat was a man of few words it seemed for he maintained a taciturn silence as we sailed away from the island. I didn’t mind the lack of communication. I huddled miserably in the stern of the fishing boat, lost in my own thoughts and hardly in a mood to talk. My tear blurred eyes were fixed upon the dwindling view of the island as we left it far astern. Soon it was nothing but a pinprick on the horizon and shortly afterwards I lost it in the afternoon haze. It felt as if something had been torn from my soul.
I blinked away my tears and glanced ahead. A sliver of land had ... Continue»
Posted by Mikebasil 3 years ago  |  Categories: Shemales  |  
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"Not MY Type?"

I’d known Kelly for most of my life. Growing up I spent most of my time at her mother’s house. It was a way to escape and avoid my parents constant arguing and fighting. It was a pretty well established fact that Kelly was lesbian early in Junior High School. Her mom and I became quite close as I was rapidly replacing the little girlie daughter she was losing to an ever increasing “butch-ness”.
By twelve years old I essentially become like a member of their f****y. Over the next few years they had the opportunity to watch me morph from a small frail Christopher into a pretty, petite and... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Anal, Shemales, Taboo  |  
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Chrissie's High School Reunion

Chrissie’s High School Reunion

When the announcement arrived in the mail notifying Kelly and I that our High School graduating class was organizing a ten year reunion we spent that entire evening discussing the pros and cons of attending. I was fairly certain that I wasn’t interesting in attending but Kelly insisting on listing all the reasons why she felt we should attend.
She was interested in going because she wanted to make passes at all the “stuck-up bitches” that pissed her off in high school. She said it would be fun to hit on these girls in front of their husbands or boyfriends. S... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Shemales  |  
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Ladyboy in a Whore House

I was born a “hermaphrodite” and I had B cup
tits when I was very young.
I was skinny so they looked BIG.

This story is from Pms I sent to SuperSatin
I was a prostitute when I was very1 3young for
a rich perverts' club.
So here's a collection of Pms that add up to
a story.


There was a client who liked me to suck him off
again and again.
he could cum 5 or 6 times. sometimes more.
I know he limped the next day!!

He fucked me too, rested then cummed
again and again.
Another client liked to cum on my face.
he'd feel up my naked body then play with himself
i'd kneel o
... Continue»
Posted by Utubeslut 2 years ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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The Day that Kelli Appeared.


One day when I was still at School (6th form), my Mum and Dad said they
we're going to my aunties for a long Weekend. Leaving on Thursday and
returning Sunday and I would be left at home.

Suddenly in a moment of brilliance an idea flashed through my head I
could spend the whole weekend Dressed (I had been cross-dressing as long
as I could remember)

Thursday couldn't come fast enough, I raced home from School in
anticipation. After having Dinner My parents asked if I was sure I would
be ok, I said yeah no problem as I have lots of home work.

After about 10 mins off they went, a... Continue»
Posted by kellianntv 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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First pair of nylons

When I was working at a machine shop I had to stand all day and my legs would ache at night.

My wife told me she was talking to a friend that was a nurse about it and she told her she should buy me some support hose.

So one day when I was getting out of the shower and getting ready for work my wife handed me a pair of womans panty hose. I asked what that was about, a little freaked out - wondering if one of my old school buddies may had said something about how we used to jack off together and this was a cruel joke.

My wife then told me about the advice she had been given and sh... Continue»
Posted by miguym4m 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Daddy's Popper Challenge

Since I've been enjoying the users’ stories here so much I thought I'd share one.
I'm a pretty good looking guy, love girls and pussy, but I am a closet tranny chasers. I love hooking up with crossdressers and transgender. I dressed a little in high school and college; I left behind the clothes but not the lust for the femme bois.

Last week when work was tough I needed a five minute distraction to clear my head so I called up Craigslist and browsed the Casual Encounters T4M. This was around 2:00 in the afternoon, a very hit and miss time. The ad that peaked my interest was "Mature Crossd... Continue»
Posted by gypsy61 2 years ago  |  Categories: Mature, Shemales  |  
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Guidelines For Other Hotwives

{About a year ago I posted "Guidelines for Happily Married Hotwives." Here is my advice for the rest of you.}

*

OK, many of you have heard about "hot wives," married white women who take lovers, generally hunky young black studs. It sounds sexy but a little scary, too. You have lots of questions and uncertainties and many of you have written to my b*****r, Homer Vargas for advice. Well, he has asked me to respond because this is something better handled between us girls. With three grown white daughters who so far have given me eight milk chocolate grandc***dren, three biracial c***dren ... Continue»
Posted by jonggu 1 year ago  |  Categories: Hardcore, Shemales  |  
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Xdresser Housewife Roxys daily chores while wife i

Well the best fuck I've ever had and continue to have all started when we intalled a pool in our back yard .Once the pool was in the pool shop sent over a young guy to set up the pump and show us how to use it ,as it was a Saturday my wife was home and she was in a bikini looking very hot. Well in walks this 6"5 very toned very sexy black guy ,when I say sexy he is the sexiest guy I've laid my eyes on and the body his arms were huge ,not one ounce of fat ,man the thoughts going through my head were insane but the one thing I knew is I had to have him 100% I would do everything I could to get t... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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An evening out.

I've been a particularly horny little girl for a few weeks now. When trying to just score a quick hook-up I have went all the ways of our wonderful age of civilization. Everything from dating sites, hook-up sites, and even craig's list. After a few weeks of just not being able to set anything up I decided to go hit up a club and see if i could find someone fun that might want to play.

I got dressed up in a sexy little outfit (fishnet thigh highs, black cheeky panties, black bra, fishnet shirt, little vinyl skirt and a pair of knee high boots) I did my make-up, fixed my hair nice, and jumpe... Continue»
Posted by bellaleroux 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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A Special Girl - Prologue

A Special Girl - Prologue

By Alhana Escher


James was nervous. Alice would be arriving soon and he had a feeling that their relationship could be moving onto the next stage that night. He and Alice had been friends for years, and he had fancied her for most of them. He could still barely believe that they had been seeing each other for the last few months. He could still remember staring at her in school. She looked so sexy in her uniform. That blue pleated knee length skirt, white blouse and blue blazer. The way her socks came to just above her knees, leaving just a littl... Continue»
Posted by AlhanaCD 3 years ago  |  Categories: First Time, Shemales, Taboo  |  
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Our First Time

I take my hand a gently begin caressing the ever increasing bulge in your pants while tenderly kissing your neck. I push you onto the bed and crawl up to you and begin to unzip your pants. I take my hand and grasp your rock hard shaft and begin to stroke you. I can feel you get harder in my hand. I stroke you faster and faster until you almost can't handle it, I stop. I pull your pants off and your shorts and begin storking again. I open my mouth and wrap my juicy red lips around you and begin to play with your head with my tongue. My other hand begins playing with your sack, massaging and twi... Continue»
Posted by uatu40 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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My Fantasy Meet

So what is my fantasy...well I suppose that being on this site is a bit of a fantasy in a way as I’m basically a straight guy who has become more and more turned on with the idea of wearing lingerie...then discovering this site accelerated the process and has made me more and more curious to actually meet another dresser like myself...I’ve also had plenty of hot times masturbating on c2c on here too and in doing so have graduated from wearing panties to stockings and now lipgloss, wigs, slips, pearls and heels...so I think that I am so ready to take the final step and actually arrange a meet.
... Continue»
Posted by Michelle62tv 7 months ago  |  Categories: Shemales  |  
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Date Coach from sissifyourself


Chapter 1


“So what brings you here today?”
Daniel looked at the date coach. He wasn’t sure of his height, taller than himself for sure, who stood at a paltry 5’ 4”, even though he was already 23 years old. He’d been made fun of his whole life for his height, but he still had a good bit of muscle, and some fat on him, as he weighed about 150 pounds, with nary a hair on his body. The doctor on the other hand, still looked athletic and muscular through his button down shirt, and didn’t look a day over 35. With his short clean cut hair and clean shaven face he could tell this guy was real ... Continue»
Posted by slim_krak 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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The strange day that left me beging for more

I was at work it a friday so I get to have a break from work after i go home anyways i was on my pc at in my offices and i called my secatary in for my papes it was late so there wasnt meny people there when she cam in i notesed that shewasnt my usal secatary she was beautayfull she had big tits double ds or big i mean these wure big tits an she hade a nice round booty and nice thick strong legs she had a tight skirt on and nice work shirt she said katie called in sick im here to fill in is tere any thing special u need i said im not sure she sad let me know ill give it to u any thing dont be ... Continue»
Posted by gothicslave 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Friends

Another story off the web. Enjoy

i have been friends with my next door neighbor for about 5 years now. he recently divorced his wife, but somehow managed to keep the house. So, we have been doing the bachelor thing together for the last few months... beer and cookouts on sundays while watching football, getting d***k, fixing cars, etc. my wife complains a little about this, but all in all, she puts up with it. she uses the weekends to visit her s****r (who is ill) and go out with the girls. i definitely make it up to her, above and beyond.

yesterday, our typical group of friends was una... Continue»
Posted by BeeJay69 2 years ago  |  Categories: Fetish, Masturbation, Shemales  |  
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