Shemales Porn Stories
Page 67

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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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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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 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 4 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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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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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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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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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 2 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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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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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 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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My shemale boss part 3

I was woken by the vibrating noise of my mobile and looked over at the time, the bedside clock said 1am. The caller I'D on the phone simply showed Bitch, naimly my boss Miss Jones, would she never leave me alone.

I answered the phone and still being half asl**p simply said 'yes'.
'Don't answer me with that tone Rob' she said. 'Sorry, but its one in the morning' I replied.
'Be a darling Rob and pick me up from the club, text me when your outside'. Before I could say anything she hung up.

I pulled my arse out of bed, slipped on some tracky bottoms and a t-shirt, jumped in the car and dr... Continue»
Posted by big_rob49 2 years ago  |  Categories: 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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Found out and Sissified by Wife Part II

After our first encounter Karen began buying me more frilly girly things and making me dress up for her. Pretty soon after that she started putting some makeup on me and bought me a blonde wig. I really liked the way I looked all made up in slutty clothes and heavy makeup and she did too. Then we would sit in front of the computer and we would watch porn together. It started with femdom stuff, with the girl fucking the guy with a strapon. Then pretty soon it graduated to CD porn, with sexy CDs sucking cock and getting fucked. Pretty soon after that it was just gay porn, usually guys sucking ea... Continue»
Posted by smilinwillie2001 5 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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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 2 years ago  |  Categories: First Time, Mature, 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 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Bet You Didn't See That One Coming


I looked down at my cell phone. The two way talk ID popped up. I shuddered.
"Hey baby, come out, come out, wherever you are. Be prepared, cause when I find you; You're going to find out that life is a bitch.!"
My God! What the fuck was happening to me?---------- I've created some kind of a monster! It was just a little joke. It wasn't even mean. I don't do mean. But here I am on the run!
The cell buzzed again. "Come on my sweet. Trina wants to play."
Lord help me! I might not last through the night! I have to be calm. I have... Continue»
Posted by vosmou_vrot 1 year ago  |  Categories: Anal, Fetish, 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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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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First Time CD In Public

Just got back from a Adult Bookstore with an arcade. Prior to going I had decided to dress in garter belt and hose, short mini skirt, bra and panties, with a see thru top. Put my sweat pants and t-shirt on over it all. Walked out of the hotel and into the car. Drove into the parking lot there were only a few cars there. Went in and proceeded to the arcade. Found a booth went in and locked the door. Put the card into the machine and found a hot she-male video. Took my sweats and t-shirt off leaving me in my outfit.

I must say that my heart was pounding and could feel my head throbbing.... Continue»
Posted by Bobcat_139 2 years ago  |  Categories: First Time, Mature, 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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