Shemales Porn Stories
Page 121

My first Trans experience

It was about 15 years ago and I thought to myself, Hmmmm I do love transexual porn, I mean I really love it! So I embarked on my search for a transexual that would rock my little world.

Adult Work, ALT and other sites skimmed though to find just the perfect Tgirl for my initiation, as I searched and watched videos, photo galleries along with reviews from fellow punters, I came across Joanna Jet, a fully fledged porn star whom, with long blonde hair, gorgeous body and a cock that simply stood head and shoulders above the rest, this is it, I thought! So without a second thought I booked a 2hr... Continue»
Posted by cardiff_paul 6 months ago  |  Categories: Anal, First Time, Shemales  |  
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Gift of a blowjob

Some years back when I was younger and occasionally crossdressed, I was staying in a motel out of state. My room was on the second floor and had a full floor to ceiling window overlooking the parking lot. I was dolled up very sexy, and drinking wine. It was early evening but already dark. I noticed a man walking around the next building several times, and as he'd come around his walk placed him walking straight towards me. I think he was just walking for exercise. I thought he might be a good candidate for me to tease a bit, so I watched until he came around again and stood in the window with... Continue»
Posted by dana213 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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MY SYBIAN

I have had my eye on the Sybian for about a year now. I watched a blonde sort of curvy girl use it once & they way she was convulsing made me envious of the toy. I really enjoyed watching her ride it, I could genuinely tell that she was getting off incredibly hard. Her screams alone made me hard. I finally decided to buy one and give it a test run. When it first arrived at the door & went running like a k** in a candy store. I practically ripped the packing to shreds, lol. When I opened it up I realized that they had sent all the attachments that I had requested. There must be 10 different att... Continue»
Posted by cocklover47 3 years ago  |  Categories: Gay Male, Shemales  |  
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Titties on ya back

When you think about Bowen Homes, you think about any other southern low cost housing project. A large 99% afro american community. Full of both your bullshit folks and a lot of real folks who just need a community; a place to live.


Growing up in Bowen Homes I can remember meeting and dealing with hundreds of personalities. Anyone coming up in my era will no dought remember a group of three notorious b*****rs .... The Beatle Boys a.k.a the Beatle b*****rs. Stephen, Randy and Handy Beatle.

Don't keep nothing of value around the Beatle... Continue»
Posted by fromtheprojects 5 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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becomiing a bitch


It was supposed to be simple. A blind date, set up online. A hot chick. Me getting laid for the first time
in a while. You know. Simple. And that's what actually happened. Sort of.
I get to the bar, I see Meghan across the way, sitting pretty in a short black dress, legs crossed,
sipping on a martini like she's sucking my cock already. Far as I'm concerned, I'm as good as fucked,
the way she's making herself out to be: smooth thighs, big, round tits, lips that could blow the cap off
a bottle of Bud, legs long as tomorrow and an ass as big as today. Fuck, I feel I'm in the bag already,
... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Interracial Sex, Shemales  |  
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Both girls had nice cocks..

[user]http://xhamster.com/user/scorpiodragon[/user]

So Im online, couple years ago, in a chat-room, im checking out profiles, looking at their locations, bingo find someone in California. finally found someone with similar interests, BOTH OF US very horny and love to give oral top & bottom also HIV-.

She didn't live that far, we started regular chatting n flirting just about every other night..
One night she happen to be in LA - Im in the valley not too far. So I Sent a TXT PM. She replied back very fast.. It seemed we had instant chemistry always flirting.
always saying lets hooku... Continue»
Posted by scorpiodragon 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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China (Part Two)

China had invited me to a little party at her house for her “Special Friends” it wasn’t supposed to be a sex party but there were going to be plenty of girls I would want to at the very least flirt with. And she said, “I will make sure to put you in the hot tub with at least six or seven that will just love you.”

I was hard the moment she even mentioned that opportunity though I had to realize this wasn’t supposed to be about sex it was just a little gathering of her friends and others who liked them. There might be prospects of sex for a later date or even possibly later that night but n... Continue»
Posted by NaughtyNshy 3 years ago  |  Categories: Shemales  |  
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xdresser Foxxiroxxi fucked by daddies poker buddie

Sorry its taken so long for the final part to be written . So im in the car with my two black bulls one is driving and im sitting in the back seat with the other . This is when I get to see how big marcuses cock really is mmmmmm OMG its fucking huge ,like the size of my forearm . I have never seen such a huge thick cock in my life and it was right in front of my eyes . All I can do is stare at it for a while ,it had me mesmirized... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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My "boyfriend" Moby

My "boyfriend" Moby

Moby is my boyfriend and he likes when I dress for him, I always wear my black lingerie: my black garter belt holding up my sexy black stockings, my bikini panties, 3 inch heels, my black bra and my black chemise. That’s the way I greet him at the door.

Moby didn’t know about my cum eating fantasy. When I sucked his cock, I usually let him cum in my mouth, but I didn’t swallow. I loved giving him a blowjob but I didn’t swallow. After reading some of my stories, I decided I needed to eat his cum, I was a cocksucker and I should swallow my guys cum.

I told m... Continue»
Posted by guycd 2 years ago  |  Categories: Hardcore, Shemales  |  
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Two Gurls and a Guy

I know you had a long day but do you mind if I invite a girlfriend over tonight, Celeste asked? Of course not babe I am just going to chill upstairs with a book tonight. Who is coming over? Just a new friend Carmine I met at work. Cool I replied as I finished dinner and headed upstairs. Kicking back on the bed half asl**p and deep into a novel I heard the doorbell ring, some chatting a wine cork and the back door slider. At some point I must have dozed off and awoke startled with Celeste in a black see thru silky nightie rubbing me thru my sweats and kissing my neck. My cock begin to stir as I... Continue»
Posted by iheartm2f 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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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  |  
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The Origin of Sgt. Steel Part 2: Iraq, Internet Po

For a long time I skated around the periphery with my attraction to shemales and fembois. After my initial exposure watching Jaye Davidson in "The Crying Game," I went back to living with my soon to be future ex-wife and my two stepdaughters.
I didn't really start considering shemales and fembois until my second deployment. In August 2007 I arrived in Iraq. Although I have been in the military for over thirty years, I’ve never been one of those gung ho types. To be honest I’m more of a cynic. Kind of like a character named the Comedian in a movie called Watchmen. He looked at all the serious... Continue»
Posted by sgtsteel 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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When will normality return...

Having been caught and transformed into my wife's house keeper, the initial excitement wore off. We now slept in separate rooms and I was continually being told what to do. My wife often came home late from work and whilst serving her supper I was convinced I could occasionally smell another man. Part of me didn't care as I was living out my dream of being a full time transvestite. Less than a week had gone by and my breast development was coming on well. I was close to out growing my bra and suspected I would be going up a size soon. I was ordered to remain dressed each day and to never wear ... Continue»
Posted by LaceTops4U 7 months ago  |  Categories: Anal, Fetish, Shemales  |  
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Inmate Succumbs After Seven Years

In the seven years that Damon Winslow had been locked up for home invasion, he had never once had sex with a guy. He was not gay was not about to start just cause he was in the slammer for 10 years. The twenty-eight year-old light brown prisoner swiped the screen of his contraband phone. He was looking at ass pictures of his ex. After getting a hard on, he decided to jack off his fat meatiness. After shooting a decent sized load, he drifted off to sl**p.

The five-foot-eleven brotha was up just before the C.O.s came around to announce it was time for breakfast. He brushed his teeth and went ... Continue»
Posted by faggyboi 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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Chaz

Chaz

I met Chaz online. It was to be the first time I met and dressed for a guy without my wife’s knowledge. She had stopped being into dressing me or letting me dress around her. She felt we needed to get back to “normal” play.

Chaz told me he wanted me to come over in the afternoon around 3 pm after he got home from his teaching job. From our online conversation I knew that he was single, had an apartment, was a top and was looking to get sucked. He seemed a bit indifferent towards my dressing but that was ok.

I arrived at his place which was on the second floor of a big three st... Continue»
Posted by MichelleSEmass 3 years ago  |  Categories: BDSM, Group Sex, Shemales  |  
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Baby's Surprise

Baby's Surprise

After a long hard Stressfull month at work I came home Friday and Lisa was not home and had left a note
(Hey Baby unwind and take a shower I left somethings on the bed for you wink wink, See you in an hour xoxo Lisa)

I sit down turn on the stereo and get loaded, I get up and go to start the shower and take a shower and shave
all over and clean out. Lisa's wink wink is a hint to shave and clean out back there she wants to play.

Back Story 10 years ago Lisa and I ventured into Strapon's and then one night as she was using the Strapon
in Me she said Hey Baby I want yo... Continue»
Posted by Bi_Norfolk_cd 11 months ago  |  Categories: Anal, First Time, Shemales  |  
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Scum - Part 1

I couldnt believe it was stupid enough to fall for it, because it wasnt going to be a real offer… was it?
I was stood there outside the prison on a road round the corner on a cold wintery night, waiting to be let down.
Was I shaking because it was cold and I was just wearing a short mini dress to show off the stockings, suspenders, and thong, with high heels and large hoop earings, with my long hair swept down and round to one side….or was it because I had a slight chance that maybe, just maybe it was actually true, and was about to happen?!

My last text to say I was there as planned had ... Continue»
Posted by tarasexytgirl 5 months ago  |  Categories: Hardcore, Shemales, Taboo  |  
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An unusual surprise

This storey is a bit different to anything I have written before. It was written for a friend as this was a scenario she wished to explore.

Sally contacted me and asked if I fancied some fun, never being one to turn down a good time I immediately agreed, she said she had a little surprise waiting and I was intrigued. I arrived on time and was stunned to see Sally sat with another beautiful lady at the bar, after greeting both ladies Sally suggested we head straight to the room as she could not wait to show me what the surprise was!

As the room door clicked shut behind us I watched as yo... Continue»
Posted by zibbles 5 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
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a very special girl

"Slam!"

Everyone in the hallway jumped slightly, turned and quickly looked at
the tall girl near the sound of the slamming locker. Satisfied that
there was no crisis at hand, the k**s at the school mostly went about
their business. Of course, there were the few admirers that glanced at
the girl at the locker, but it was no major deal.

After all, Marilyn Walker was used to being looked at. After all, how
many 6'3" girls wear 4 inch platform heels? How many 6'3" girls are
there? Oh well.

She swung her backpack over her shoulder, and strode slowly along the
bustling hallways ... Continue»
Posted by pcarter 1 month ago  |  Categories: Interracial Sex, Shemales, Taboo  |  
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The continued adventures of Allison the cumsissy

The Continued adventures of Allison the cumsissy
This is a continuation of the same sissy slut’s story from my two previous works about Allison the sissy schoolgirl and her black daddy.

After the week long fuckfest, Allison the sixteen year old sissy schoolgirl boybitch had with her black daddy neighbor, she realized she was meant to a be a sissy cumwhore and decided to shop for as many sissy items as she could afford as soon as she could discreetly do so. As luck would have it, the following weekend her parents informed her that they would be going out of town yet again to visit his mothe... Continue»
Posted by AllisonCumms 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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