Shemales Porn Stories
Page 66

caught masturbating & crossdressed living at a

This is the first story of a few that I was so lucky to be a part of and I would love to share them with you!

I had hired this woman as a delivery driver because the store I had just taken over had ruined the reputation of the business with terrible service. Her bubbly demeanor, bordering on ditzy was cute and she was herself a beautiful 40 year old woman and a milf for sure! She would be my best tool in the road to rebuilding the business. The customers will love her. She was tall with long slender legs and a real nice round ass, small titties with huge pinky size nipples. Her hair wa... Continue»
Posted by happytayls 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.

We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.

Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or would prefer to wait in the room while she finished dressing. I told her I would like to wai... Continue»
Posted by johnny_antares 1 year ago  |  Categories: Shemales  |  
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Boi CD Hooker

There I stood, by the gas station waiting for my next "client" to come along. "Client" makes it sound so professional. Shit, I was waiting for
some horny old man to come by and pay me for my ass. I admit I looked good. All 5 ft of me, long black hair, smooth tanned skin, wearing
tight torn daisy dukes with a hole in the ass for easy access and a bra covered by a leather jacket. No underwear, of course. That just gets in the
way. I'd had three "clients" tonight. I'm sure i could have another soon. Who were these clients? Whoever would pay my fee. What do they look
like, I don't usually reme... Continue»
Posted by TiniToni69 25 days ago  |  Categories: Fetish, Shemales, Taboo  |  
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super cock 14 inches meets angel buxom (written by

This how I see the biggest cock in the world violating the biggest tits in the world ,was looking at the news one day when they had announced the opening of a very unique new building that was just built in NY NY and clamed to be the tallest in the world at 4500 stories tall it was the biggest building on the planet ,it is uniquely shaped like a massive erect cock shaped after Mr Supercock the longest most powerful cock in the entire world the next biggest would only be about half his length the building is owned by Mr Supercock ,multie zillinare porn king ,king of the cock.
They showed some... Continue»
Posted by huge_cock_rules 3 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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Halloween Pt3

My enthusiasm waivered a little once his crotch was in my face. I could see his cock straining against his sweat pants. But, I considered the alternatives: He was horny, and he was expecting relief. We were in his frat house. And he was much bigger than I was. And, I was dressed like a young woman hot for the D. If I told him no, he could easily beat the shit out of me. And then tell everyone he was fooled. God knows what his frat b*****rs would do.

Besides, he'd sucked my cock. How bad could it be? Women liked giving blow jobs, and obviously some guys did too. It's not like anyo... Continue»
Posted by TransContinental 12 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Boston Surprise

Boston Surprise by FRSWRITER
It had been weeks since I saw the gurls, their memory burned deep in my brain.

Hanging around the house with not much to do didn't help either. I had been trying to call Jill for a few days, but she would not answer. About now I was thinking it was a dream and never happened.

It was getting late and I was contemplating going out and trying to score, headed for the shower to get cleaned up and go. The water felt good and I was getting hard just thinking about what tonight may bring. When I was all soaped up the fucking doorbell rang, I yelled but I guess they... Continue»
Posted by frswriter 2 years ago  |  Categories: Shemales  |  
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xdresser foxxiroxxi fucked by daddies poker buddie

So I have finally got my men doing what ive wanted for a long time now and I have never been so horny . John is licking and fingering my ass while im getting marcuses tounge shoved in my mouth all the while my daddy and his buddies are outside . Fuck me im so fucking horny these guys could do anything they wanted to and I wouldn't stop them. Johns fingers start at one then two big black fingers slowly stretching my virgin ass then he slipped a third in and out licking and sticking his tounge in my ass then fingering me ,he kept the same pace making sure he didn't rip me so it would be a pleasu... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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LADYBOY DOMINATRIX

YOUNG LADYBOY DOMINATRIX
by utubeslut


If you read my other stories you know I'm intersexed
and I was a ladyboy prostitute when I was um, very young.
I don't condone such activities.
They were sick perverts who used me.
True I got a lot of money and expensive gifts but
that doesn't make it right.
They should all be castrated.

This is a story about one of my clients.


Let's call him Mr. submissive.
My sex club supervisor gave me a sheet of paper with all
of Mr Sub's needs and desires.


How do I begin this? It's almost unbelievable.

An expensive hotel room, laminated h... Continue»
Posted by Utubeslut 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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A night to remember with G/F and a sweet little tr

At 52 years old i have had a extensive sex life. I have always been impressed by and i will use several words to describe Shemales, trans, Gurl, Traps, cross-dressers. I guess I like the fact that they take some time to look and or change into a better person and going from male to female can take some time and tricks.

Boston MA 1997: My G/F and I decided to add some spice to out very adventurous sex life. We went out one night to a alternative club that had a fashion show. Most will call it a drag show, this was a little slice of heaven for her. She played with my cock through my pants as ... Continue»
Posted by wankingamerica 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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My life at home.

This is a purely fictional story, and in no way reflects real events.


My name is Greg, I am 47, 5'11", 225lbs, and a widower. My wife died shortly after c***d birth. She was on her way to the store, when a stolen truck, driven by a man wanted by the police. She left me to raise our son, terry. for the last 16 years, I have been mother, and father to him, watching him grow from a little boy, to a young man.

Terry was never into sports, just accademics, and these he excelled at. He was never muscular, kind of thin, graceful. I work as a product designer for a multi-national com... Continue»
Posted by chefjohn2112 6 months ago  |  Categories: Anal, First Time, Shemales  |  
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Tgirl fun

Because it was a little cold I went out dressed in a nice pair of tailored jeans, which show of my bum beautifully, black bra, lacy top and a really tarty shimmering jacket. I was wearing a lovely pair of ankle boots and was able to quickly slip out the front door of my house and into my car. It felt wonderful to be dressed up and driving through the rainy streets. People were able to look at me when I stopped at traffic lights but no one seemed to notice anything amiss. I wasn't able to park too close to Mandy's flat so had a longish walk before I got to her front door. I loved the sound of m... Continue»
Posted by TaniaHarvey 4 years ago  |  Categories: Anal, Shemales  |  
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Daddys whore


I had always been fascinated by the feel of womens clothes against my skin, and today was no different. Mom was away on a business trip to Canada, and dad was away at work for the next couple of hours.

I had always had an effeminate look to me, with me being 6’1” and thin as a twig at 19, I was scrawny. I had bought a black wig to go with the outfit that I had picked out. It was black 6” heels, black pantyhose, a black garter belt and panties, with a short black skirt and a little black tube top. I was hard just thinking about what I would look like.

I took a shower and completely shav... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Gay Male, Shemales  |  
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Transsexual Son Daughter

Now I’m a 51 year old mother of one and watching my Daughter who’d been once my son putting on that very nice silk blue bra from Harrods department store and lift up her huge breast in to them made me so wet. Now seeing my son all now transformed and transitioned in to a beautiful woman but she’d still had got her manly bits now that didn’t harm anyone but boy did she look awesome and lovely all 5’9 of her slim size 10 with her rather large 46DDs which shed always wanted and her slim lines like a guy would say about a classic sports car.

Now as I was saying I am a 51yr with a son that had b... Continue»
Posted by 1superhornyguy 1 year ago  |  Categories: First Time, Mature, Shemales  |  
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Brad cant go back

It was a foggy evening in the Town. Brad was walking beside the road that lead to a truck stop. He couldn’t help but wonder how the hell everything happend so quickly. Brad was 19 year old boy who seemed to be an ordinary c***d of an ordinary f****y. He was a dark haired skinny boy and had a bit of a feminine features. He was currently in no school as he was not admitted to any since he didn’t do well on the tests. He was living with his mother, enjoying the carefree lifestyle of a student who didnt go to any school. He had friends but no girlfriend; he never had a girlfriend. Yes he seemed o... Continue»
Posted by vacantwhore 1 year ago  |  Categories: Gay Male, Shemales  |  
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End of the Week

Ernest Gaines, known by most as ‘E’ or ‘Big’, bounded down the corridors of Presbyterian Regional Medical Center wheeling a patient towards discharge. It was shortly before 8:00 a.m. on Saturday which meant this was his final task of his shift. He made it to the waiting area and brought the chair to a stop as the elderly man peered out the window for his f****y.

“What’s going on,” a fellow orderly asked.
“Can’t call it,” E replied.
“I hear ya, man. You gettin’ off soon?”
“Yeah. Goin’ to the crib and chill. Got three in a row off.”
“I’d do that. But I got too many people at home to get a... Continue»
Posted by faggyboi 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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LOVE

I was work as a counselor for people with gender identification. One day a beautiful lady, Pham, approached me for an assignment related to her doctoral work at an university nearby. Her work was related with gender identification issues.

Our scientific bent of mind and approach to research enabled us to relate closely to each other. I would say that was an attraction. We met at least thrice a week for one year and all that we did was to talk and share notes on gender identification issues over coffee, tea, lunch and dinner. We spent days and nights talking about it over phone, at office ... Continue»
Posted by tran4mate 1 year ago  |  Categories: Shemales, Taboo, Voyeur  |  
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Interstate Reas Area Whore

Driving down the interstate the sign said Rest Area one mile. My heart skipped a beat and there was slight stiffing of my male meat in anticipation of events to unfold. This interstate rest area was always packed full of eighteen wheelers as many as forty. Surely one or two of these truck drivers would be horny enough to over look the fact that this slut had a little something extra a top her nylon covered legs.
I had a black merry widow corset on that pulled my waist in a nice four inches. Eight garters held up my coffee colored FF nylons. I had on five inch red stiletto pumps. My bla... Continue»
Posted by littleoralvee 3 years ago  |  Categories: Shemales  |  
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My First Kiss

This is a story in progress so please be patient.

My name is Denise Babcock. I am a longtime transvestite having begun cross-dressing when I was 12. I began to have sex with other boys shortly thereafter. But it wasn't until I was 18 that I shared my first kiss with a boy. Paul had been one of my closest friends all through high school and we stayed friends even after graduation. Often when we hung out together complained to each other about our troubles with girls. One evening he called me up to go hang out at a bar with him. His girlfriend had recently dumped him and he was a bit depresse... Continue»
Posted by DeniseTV 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Trapped and Trained Sissy Ch. 18

Trapped and Trained Ch. 18
I don't remember much to how I got here from the previous night, mostly just flashes. I remember the limo pulling into the parking garage and seeing the redness behind my eyelids as we passed under the various lights before it crept to a stop in front of the elevator. Mitch climbed out, then Vivian stirred me awake and led me out, still wearing just my red latex leggings, gloves and black heels, dried cum sticking to my legs and pulling at my skin as I walked. Mitch quickly slung me over his shoulder and strode to the elevator, his hand resting on my ass as he walke... Continue»
Posted by hpm12 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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Tranny's First BBC

Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me.

Normally it’s just the usual crowd of guys but several weeks ago a big muscular type African guy in his mid 30’s kept going past me and looking at me out of the corner of his eye. After about his third walk past I gave him a little smile. When I could see him coming down the hall the next time, I got up and slowly walked around the corner into the next hallway so he... Continue»
Posted by kbking64 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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