Shemales Porn Stories
Page 76

“Some first date, huh”

So I had just gotten this new job at a fast food/dine in kind of place for the summer trying to make some extra money before the fall semester started. And there was this boy named Danny that would come into the restaurant every so often. He was really cute and had nice lean looking body. He was pretty shy but I could tell he was in to me because quite frankly the food wasn’t that good and he would always stop by during my shift checking me out. So a few weeks past and he had yet to make a move. I was a little hesitant as well because I didn’t know how accepting he would be of my “situation”. ... Continue»
Posted by pleasurenfun 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 2287  |  
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Weekend with my s****r - part 1

Continued from sunbathing with my s****r.

The week went so slowly, my mind always wandering back to our day together....stroking my cock endlessly replaying each and every kiss, touch and stroke. We stuck to our agreement of not talking about it when anyone else was in the house, not touching or staring was the hardest part, the sexual tension between us was incredible, I can't believe our parents didn't sense anything. We did leave bedroom and bathroom doors open just enough it was safe. Each morning when Jane left for work she'd leave some underwear on her bed for me.....twice it was e... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 5955  |  
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My uncle Jim opens the door part 5

As I am here on my knees on the inside of the front door wearing my moms sexy lingerie and bight red lip stick on my lips with my uncles bottle of beer in my hand I see the front door open up. My uncle see me and looks at me waiting at the front door like he told me to be. He smiles at me and says " that's a good sissy little whore. You did as you were told to be waiting for me". My uncle did not come in the house he just pushed the door wide open and than with his camera in his hand took some nasty pictures of me waiting in the door for him. Than told me to stand up and hold out his beer in m... Continue»
Posted by suecd58 2 years ago  |  Categories: Shemales  |  Views: 1033  |  
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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 1 year ago  |  Categories: Shemales  |  Views: 1540  |  
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Gang banged in bondage by shemale co-workers

I had just got home when my cellphone started to ring. When I anwered I heard my boss on the other end of the line. And she told me to come to her house for some "Fun" in a very ¨seducing voice.
After I took the buss there and walked up her driveway I kept wondering if my great looking boss and her sexy secretary was gonna tie me up again. The first time had been a real suprise but I had still enjoyed it in the end.
When I knocked at the door her secretary opened it and beckoned me in.
When I came into the living I came to the conclussion that I would be tied up again. There was bondage equ... Continue»
Posted by Ankakalle 3 years ago  |  Categories: Shemales  |  Views: 1356  |  
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lucky guy (part 1)

Ive been with my girlfreind may for around 3 years now,she was my fuck buddy until we decided we wanted a realationship.
Although we dont live together as i like to keep my apartment for a bit of space now and then.
After a while the sex dried up and we were more freinds than lovers which was nobodys fault it just turned out that way.
May had a daughter,a very spoilt daughter who was growing up quite quickly,Raynor was 21.
I had never thought of her sexually,that is until May asked me to decorate Rays room while she was on holiday as a suprise for her.
Then it happened.
I had to move Ray... Continue»
Posted by wankersoffagain 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 845  |  
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Tonia...

One night I went to a different club to check things out. By now, I
knew what I was looking for and where to find it. I was cruising the
area with several bars for people with my kind of preferences you
know women with more to offer a man.

I parked out in the lot and began to walk in as I did I noticed this
beautiful brunette with long legs. I was very interested in
following her into the bar. I rushed to open the door for her as she
just politely blushed and smiled at me. I tipped my head to her in
respect trying hard not to blush too. She smelled very beautiful,
the sweet smell of... Continue»
Posted by NaughtyNshy 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 470  |  
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World of Confusion

I first fell in love with transexuals when i first stumbled on a video called world of confusion, at first i was like oh yeah! this is gonna be a good porn one guy and three girls awesome, so then at first the guy is jerking off then all of a sudden these three females come out i was like about time now suck his cock, so this one female goes down on him then the other female start playing with the other females ass fingering it i was like oh yea! this is getting hot then out of nowhere he grabs one of the females by her g-string and starts pulling her panties down and then starts licking her p... Continue»
Posted by Ray3 2 years ago  |  Categories: First Time, Sex Humor, Shemales  |  Views: 983  |  
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my first tranny pt. 2

it felt so good to cum in her mouth. that wasn't planned. her mouth just felt so good. nice & wet. told her what really got me off so fast was having her cock in my mouth.

"in that case, come here & suck it some more."

she laid down with her legs open & her dick in the air. without hesitation, I got between those nice long legs & put her dick in my mouth. she was moanig as I sucked her cock. she was about a good 6 inches. I just sucked & sucked. she put her hands on my head & was making me go up & down. I got her cock nice & wet.

I never told anyone this but, I loved sucking her coc... Continue»
Posted by radec_24 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1124  |  
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The Slave and the Sissy Part Eight

Slave kissed Pepper’s pretty face to reassure her before they were both shackled and then gagged, and sat on a prominent open seat on Ayesha’s carriage, their hands bound in front of them; Ayesha loved to display her power and ownership of slaves, and would always ensure other people were made aware of it, even if the chattels were only hers to borrow. Slaves cock was in an erotic quandary as he felt the closeness of his soft sissy; bound and submissive and thinking only of how she could please him, and there before him cracking a whip above the heads of the horses, sat the impressively domi... Continue»
Posted by midsummerman 1 year ago  |  Categories: BDSM, Interracial Sex, Shemales  |  Views: 221  |  
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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 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1339  |  
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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 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1539  |  
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My Early Crossdressing

I started cross dressing around 12. At first it was knickers or tights. As I got older I started to get more serious with it. Just after I turned 16, I'd often go out round the streets round town dressed in full girls clothes. I'd always prefer going out late in the evening in winter, as I'd not pass many people and id normally only pass a few cars, some would slow down as I walked along the side of the road.

One day I was home alone, my parents were away for the week and my s****r was staying with her boyfriend. I turned up the music and got dressed from head to toe. I was pretty much smoo... Continue»
Posted by VirginAsAGirl 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 1854  |  
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He or she? It did not matter to me!

I was sitting in my small apartment watching TV and having a few pipes when I heard a ruckus in the hallway. It was my room mate Joel and some of his friends retuning from the pub. When they knocked on the door I answered and there he was with some girls he knew but who were all strangers to me. As they entered I noticed Candy, a tall (obviously) male dressed in a bright yellow top and skirt, black stockings, high heels and the most outlandish purple eye shadow I have ever seen. As she passed me she smiled and asked where the bathroom was.

A short time later we were sharing some lines and ... Continue»
Posted by sydguy 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 2045  |  
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Sissy crossdresser and her Black Daddy Part 2

After nearly a week of almost nonstop creampies, facials,deepthroating blowjobs and bareback anal fuckings, my black daddy and I were sad to know we had one more night in which to have our nasty, kinky fun before our respective f****y remembers return. I had dressed in all manner of nasty lingerie and costumes for his black cock to use and I loved every second in which he entered my holes. This being our last night together my daddy told me to "take a shower white slut, and make yoself pretty. I got a surprise for dat ass babygirl". My cock could hardly get any harder I was so excited. I enter... Continue»
Posted by AllisonCumms 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3056  |  
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My first time

I sat in the car outside the address and to say I was nervous is a understatement. This was the first time I had ever done anything like this and I was half thinking of just driving away.

I had got messaging to Sara a month ago after liking the pictures they had posted. I was really in to clothed sex and the pictures showing Sara in a selection of boots whether they be leather or pvc, knee high or thigh high I didn't care as long as they have a stiletto heel l love them.

As for clothes I get hard for the slutty secretary look, a nice tight pencil skirt with some stockings and high heel... Continue»
Posted by big_rob49 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3584  |  
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A slut is born.......

I've always had this magnetic attraction to slender pointy hi-heel stilettos for as long as I can remember. Even when I was just a little k** of around five years old, I used to get these stange feelings between my thighs every time I saw a young teenage girl strutting and teetering around on these fabulously erotic pointy heels - This was the 1950s era. The era "par excellence" for these gorgeous shoes that did so much to excite me but also to trouble me - Because I was only five, I didn't understand these wonderful sensations at all. All I knew was, that it must be "sinful" to have s... Continue»
Posted by caroletv31 3 years ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 1684  |  
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fantasy

This is a fictional story, a personal fantasy of mine

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"Cum to my place, I need you ;) xxx" Was the message I recieved from her. Needless to say you do not pass up on an invitation like that so I had a quick shave and a shower, got dressed and headed out to find my 'girl'.

When I arrived in her apartment it was pitch black except from the candels lit down te corridor, guiding me to the bedroom. Feeling the bl**d start to rush away from my head and into my cock I proceeded hastily down to the bedroom. I opened the door, expecting to see my lover but there was a note and a pil... Continue»
Posted by shyadam89 2 years ago  |  Categories: BDSM, Shemales  |  Views: 941  |  
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Office Fun - Part 2

Marcia was sitting in the car park of the office, about to leave having just finished work, when she saw Lee walk out of the building and head towards his car. It had been four days since they had fucked in the office, and she was eager for a second round. She checked herself in the rear view mirror before beeping the horn. Lee looked towards her and she beckoned him over, winding down the window as she did.

“Hey,” she said with a smile.

“Hi,” he replied, ducking his head in through the window. She caught him taking a quick glance at her cleavage.

“You wanna come to my place for some ... Continue»
Posted by gellid 3 years ago  |  Categories: Shemales  |  Views: 1100  |  
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First experience

I want to tell you about my first experience in cross-dressing and what happened afterwards.
First some explanations. When I was 12 or 13 years old I was a slim and tender boy with long hair (early 70’s it was normal for boys to have long hair). I lived in a neighborhood with a lot of c***dren my age (some a few years younger or older). So I had a lot of friends to play with. One of our favorite games was “cowboy and Indians”. We played this in the woods not far from our street. It had most of the time the same scenario. The older boys (2 or 3) would be the Indians and I and the younger boys ... Continue»
Posted by Catharina 3 years ago  |  Categories: First Time, Shemales  |  Views: 2080  |  
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