Shemales Porn Stories
Page 58

Moving to a Retirement Community

Chapter 13
(This chapter, as well as the next one, is dedicated to a reader who has become a big fan of this story. I've chatted with him several times and in one of those conversations he mentioned something that stuck in my mind. He knows who I'm talking about and I do hope he enjoys these next two chapters. I will also give credit to those who inspire me with ideas to use in my stories, whether intentional or inadvertent. Thank you very much, T.)
That afternoon I was out doing my daily walk around the neighborhood I met a very interesting woman for the first time. Her name is Barba... Continue»
Posted by eprise01 1 year ago  |  Categories: Mature, Shemales  |  Views: 662  |  
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Moving to a Retirement Community

Chapter 14
All I could do was stare.
I thought I was imagining it, but there it was, a cock!
Barbara has a cock between those beautiful legs.
"I guess you hate me now, don't you?" she asked.
While I'd been staring at her crotch, she'd raised up on her elbows and was looking at me. I could see sadness on her face.
I found that I wasn't mad at her though. I could feel the pain she was in and I reached out to touch her cock for the first time.
"Don't!" she said.
"Buy why?" I asked.
"Because I'm a freak!"
"No you're not. You're lovely," I tried to assure her.
"No, I'm no... Continue»
Posted by eprise01 1 year ago  |  Categories: Mature, Shemales  |  Views: 636  |  
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Moms Trannie

It was Saturday night and my friends had told me about a new club. It was about an hour out of here and had an older crowd. This sparked my interest some what having a fondness for older women.

I walked into the place and looked around, not much going on so I wandered over to the bar and ordered up a beer. A little while later the crowd picked up and things started to get moving.

The women were defineatly older here, I asked a few to dance and had a few takers but couldn't seem to lock in with them.

While I was dancing I must have missed the two that came in, a blonde and brunette wit... Continue»
Posted by frswriter 1 year ago  |  Categories: Shemales  |  Views: 4531  |  
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Aimee and Me

My name is Shaye and I’m a 27 year old pre-op transsexual. This is the story of my only sexual encounter with another shemale, which turned out to be one of the most intense sexual experiences of my life.

I first started speaking to Aimee about two years ago on an adult chat site. We had some cyber fun for a few months, jerking off on cam and generally having a good time. Eventually, Aimee asked me if I wanted to go around to her place for some real fun. I didn’t need to think about it and I arranged to go to her house a week later.

It took me two hours or so to drive to her house. More ... Continue»
Posted by gellid12 1 year ago  |  Categories: Shemales  |  Views: 711  |  
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The morning after my night out with my s****r

Continued from my other stories...feel free to read those first to set the scene.

I woke, feeling a slender arm d****d over me, gently stroking my cock which is getting harder in the knickers I'm still in from the night before.

I relax and enjoy the feeling of nails through the black lace. Before long Jane's hand slides inside my knickers and takes her cock in her hand, she whispers 'I want this inside me Danni'.

My heart races, my cock twitches at the thought of sliding deep into my s****rs wet pussy. I role to face her and we kiss slowly and passionately. Our rongues entwined as ... Continue»
Posted by ukdan78 1 year ago  |  Categories: Shemales, Taboo  |  Views: 1927  |  
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my first cross dressing play time

i sucked my first cock the other day. i posted a ad on craigs saying i like to cross dress and would like to find somebody to dress up with and take turns being sluts to each other and then i posted a few pics of me from my xhamster profile and actually got alot of replies. it took a few weeks but i finaly found somebody that like to dress up and he came over during the day and we started watching porn and i pulled out all my slut clothes and we picked out things that we wanted the other person to wear. he wanted me to dress up just like the pics i sent him so i did, after we got dressed up we... Continue»
Posted by floyd1985 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1408  |  
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Daddy's Caddy

From the moment my Daddy first took my young, naked body in his strong, masculine arms, I knew that he was not like other men. At least not like any of the men that I had gotten naked with! Daddy knew something was different about me when he began catching me, his 12 year old son, playing dress up with my Mommy's make up and wigs, outfits, jewelery, hose and heels! It was shortly after my 14th birthday when we became lovers.

Every morning, I would wake up at 430 am so that I could jump in the shower, shave myself smooth, and put on something sexy for Daddy. Around 5 am, as quietly as he ... Continue»
Posted by cdsexslut 1 year ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 1080  |  
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monday night football

HELLO EVERYONE
I hope everyone enjoy my last story happen on black Friday please leave comments so I know how much u love the story thank you

Well we getting close to football playoff and every other Sunday some one throw football party at their place sometime I get invited sometime I don’t depend what kind of party and what kind people their as you know im a pretty shemale and im proud of it.
My story always a real experience happen to me or my friends I love to share after all us shemale also have feeling too

On Monday night football Texans vs patriot one of black gay friend throw
... Continue»
Posted by shawn777 1 year ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 1776  |  
47%

its monday night football

HELLO EVERYONE
I hope everyone enjoy my last story happen on black Friday please leave comments so I know how much u love the story thank you

Well we getting close to football playoff and every other Sunday some one throw football party at their place sometime I get invited sometime I don’t depend what kind of party and what kind people their as you know im a pretty shemale and im proud of it.
My story always a real experience happen to me or my friends I love to share after all us shemale also have feeling too

On Monday night football Texans vs patriot one of black gay friend throw th... Continue»
Posted by shawn777 1 year ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 2092  |  
50%
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I meet Bam [dildo/poppers/training]

So I had the place to myself again, and if anyone has read any of my other stories, you probably know what I like to do when I'm alone...

My wife wasn't gone more than ten minute for a weekend get away with a girlfriend, when I was out the door too. I was heading to my local sex shop to pick up some fresh poppers,and maybe cruise the video booths and look for some dick. When I pulled up to the store, I was a little disappointed because there were no cars in the lot. I made the trip, so I decided I'd go in anyway. When I walked in,the first thing I noticed was empty shelves-"not good" I t... Continue»
Posted by pbg732 1 year ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 2300  |  
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My first time with a tranny

I had been looking at shemale porn for a while and dreaming of being with one. A few years ago I got away from work early and decided to have a few drinks. I was horny and soon looking at adverts in the paper when I stumbled across one for a ts hooker in the area. I called then number and the husky voice told me the address and to come in 30 minutes.

The next 30 minutes I was very nervous and took a minute or so before I worked up the courage to ring her doorbell. She let me in to her flat dressed in very little. Slightly taller than me, amazing breasts, big slutty shoes and an already erec... Continue»
Posted by ross80 1 year ago  |  Categories: Shemales  |  Views: 3306  |  
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Mom the shemale bitch

Hi I have always had this fantasy

The fantasy starts out in high school a number of years ago, when I started having dreams of the kinkier kind, but not really understanding why. The dreams were about women that had big breasts and large hips as well as being tall and big boned.

The dreams always started out the usual way with a date, dinner, kissing, and petting, but as soon as I got the breasts out and satisfied that part, the girls were pulling down their pants for me, but not complaining I went straight for my goal.

The problem was that as the pants came down, the package would a... Continue»
Posted by frswriter 1 year ago  |  Categories: Anal, Mature, Shemales  |  Views: 12001  |  
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Raquelm part 1

Having arranged for three visitors to service her wife, Latex Letitia set about dressing for
the occasion. Letitia had her own kinky wardrobe and what she was short of she
borrowed from her wife Raquel. She donned a PVC basque, her wife’s rubber panties,
long rubber gauntlets, a ridiculously short latex rubber mini skirt all in black except for
her favourite boots the shiny, baby pink PVC 6” platform thigh high jobbies! It made her
feel horny. She stood in front of her wife’s mirrored wall and rubbed her shaved,
hardening cock through her panties. No makeup would be required tonight as s... Continue»
Posted by latexletitia 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 452  |  
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tranny e****ts are the best

Being a rather horny fellow who loves to get spun on meth and party, I occasionally had to craigslist and check out the casual encounters section to see what's out there. So after seeing The Hangover 2 and seeing sexy transgendered girls it got me a little curious to try it out i mean what could i lose they couldnt say no to my 10 inch cock. So doing a big bump my cock was leaking as if i just had a wet dream , I got home and dared to check the T4M section that was so naughty and off limits before. I came across an ad where a passable Latina wanted to have some fun and she included some pics. ... Continue»
Posted by brianlongham 1 year ago  |  Categories: Anal, Shemales, Taboo  |  Views: 1124  |  
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show me her cock

I hadn't done much partying .I was a mum all too young and a good one .But now theyve fled the nest and I am catching up on lost freedoms .
I am a single women we got on great except 10 years ago I lost them forever.A car crash.It took years too feel anything like horny.Id try sometimes really hard
spending good money on pumps pills and penis props .I was showing flesh to debt collectors and all in aid of getting turned on.
The only thing tat worked was a growing facsination with a new girl in opposite appartment.Why I felt hardend nipples and aclitoral buzzing as I had to... Continue»
Posted by looberry-Cunt 1 year ago  |  Categories: First Time, Shemales  |  Views: 1364  |  
43%

mommy's wanna be girl

"Hi honey, how was your day?" My mom called out her usual question as I came in through the side door, and tried to quit sniffling. In vain -- I still had the hiccups from my recent crying jag, and my nose was running. I'm sure my face was red too.

"F-fine," I hiccuped. Obviously, it hadn't been fine.

"Oh, hon, did those boys tease you again? They're so rude."

"Why do they keep calling me a girl, mom? It's so mean! Just 'cause I don't play sports..."

In truth, it was more than that -- I just didn't want to admit it to myself.

My name's Jake. I'm 18, but you wouldn't think it -- ... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Fetish, Mature, Shemales  |  Views: 1432  |  
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black man's sissy boy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.

One day when my mom was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The draw... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 6798  |  
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sissy wants to be black man's slut

Hi Sweeties! Guess what? Well, adult arcade sissy, Miss Terilyn Bardot, got her ass whipped but good the other night. It happen at an adult video arcade in Providence, RI.

One of the reasons Terilyn likes going there is because they could care less what kind of sex goes on in those preview booths. in fact they installed larger booths that hold up to 6 occupants. A lot of the adult bookstores, mainly the ones in Massachusetts, have signs posted to the effect of no sexual behavior allowed, or, one person per booth - violaters will be ejected...legal prosecution, etc. So that's why Terilyn lik... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1323  |  
87%
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mommy's wanna be girl

"Hi honey, how was your day?" My mom called out her usual question as I came in through the side door, and tried to quit sniffling. In vain -- I still had the hiccups from my recent crying jag, and my nose was running. I'm sure my face was red too.

"F-fine," I hiccuped. Obviously, it hadn't been fine.

"Oh, hon, did those boys tease you again? They're so rude."

"Why do they keep calling me a girl, mom? It's so mean! Just 'cause I don't play sports..."

In truth, it was more than that -- I just didn't want to admit it to myself.

My name's Jake. I'm 18, but you wouldn't think it -- ... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Fetish, Shemales  |  Views: 721  |  
53%
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black man's sissy boy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.

One day when my mom was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The draw... Continue»
Posted by jeffreybarnes 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 741  |  
41%
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