Shemales Porn Stories
Page 115

Daddy's lil bitch

As a young boy growing up I always had a fetish for dressing up like a girl. When I was 20yo I had my first experience with an older man, Tony a man in his 70s. I met him through a phone chat line and we seemed to hit it off right away. He told me that he would buy me some clothes and lingerie to wear for him when we met. So after a couple weeks of phone chat I mustarded up enough courage to meet him face to face.

When I arrived at Tony’s house he greeted me with a warm hug and kiss. Tony was a very handsome man, stood about 6’ tall and clearly looked like he took good care of his body. He ... Continue»
Posted by aznfemboi 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 3068  |  
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Taken to be a Shemale Lover

I had went to work at the burger joint, when the manager informed me that 'I have too many people on payroll today, I need you to clock out and leave.' This is what happens when you work for a fast food joint, all the k**s that go to school and can get a permit flock to the fast food places. At least you get some training in how to be on time and understand job responsibility.

As I was working towards the park a coral blue car passed by, it pulled into the lot across the street and came speeding back. The driver was a familiar face, Joliet, one of the she-males that enjoyed my restraine... Continue»
Posted by d4david 3 years ago  |  Categories: Anal, Shemales  |  Views: 1580  |  
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something more to her, part 1


jasmine had just left the local club and was walking to her favorit street corner. jasmine had an IV league education, was extremely beautifull, having dark tanned skin, having 34 DD breasts, a perfect figure, and perfectly done honey blonde hair. she was smart, sexy, and she was one of the most charming people she knew. so why was she selling herself on a street corner? the reason was simply becuase it pleased her as much as it pleased her customers. she may have convinced herself it was becuase she couldnt find a man that would except her 10 inch "secret" that she hid under her tight mini ... Continue»
Posted by mj2397 3 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 537  |  
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MEL-SEXY OLDERMAN

MEL IS 66 YEARS OLD AND IS IN MY MUSICAL ORCHESTRA. HE IS HANDSOME WITH A GREAT PERSONALITY. HE IS MARRIED BUT HIS WIFE IS AILING ,SO I DONT THINK HE GETS MUCH ACTION!HE IS A HORN PLAYER AN I IN THE PERCUSSION SECTION.MEL AN I JOKE A WELOT AN HE SOMETIMES JOKINGLY SAYS I HAVE A NICE ASS! HE HAS BECOME MY FANTASY DURING MY MASTURBATION SESSIONS!WE HAD A PERFORMANCE IN SIMCOE AN WE HAD TO GET CHANGED AFTER PRACTICE INTO OUR UNIFORMS.THE MEMBERS WERE PROVIDED CLASSROOMS TO CHANGE INTO.WHEN I GOT THERE I LOOKED AROUND TO SEE WHERE MEL WAS CHANGING! THERE WERE ABOUT 10 OF US CHANGING SO I JUST COUL... Continue»
Posted by bashunia 3 years ago  |  Categories: Shemales  |  Views: 666  |  
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A Night to Remember

About six years ago just before Christmas I went to a transvestite bar in the centre Manchester after I had finished my act at a private party on the outskirts of the city. I was dressed in my sexiest outfit mini dress, suspenders, sheer stockings and 4-inch Fuck me hard stilettos, and my favourite long brown wig. I was fully made up with long false eyelashes and blue shadow, red painted finger nails, and dark red lipstick, pearl necklace and large chunky earrings. I looked quite stunning . I have a very good figure and long shapely legs. I need to, in my line of work, as a part-time tranny... Continue»
Posted by TgirlViki 3 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1208  |  
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How i became a girl

Hi my name is Mandy and this is my story..in parts. I started dressing when i was in my early teens. At first it was just panties, maybe pantyhose and masturbating with my friend B, but it soon became wearing skirts and heels, little tube tops and sexy dresses, then it was makeup and wigs, and soon we were both dressing up fully, doing our makeup and hair, and accesorizing with pocketbooks and jewelery.

We had suuuuccchh hot sex, kissing and fondling each others sexily clad bodies, our hands and lips and tounges roaming, licking, stroking and nibbling each other erogenous zones, before a ... Continue»
Posted by miniskirtmandy69 3 years ago  |  Categories: Shemales  |  Views: 1921  |  
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Hooky

"You're not seriously gonna leave me like this are you?" Daddy Mike said as he waved his now hard (again) cock back and forth. I stood on wobbly legs as I had still not gotten used to walking in the heels daddy bought for me.

"Daddy I gotta go to class, you already fucked me twice. You can fuck me again after class, now I gotta find my clothes and get out of these stockings and thong." I looked around for my pants but couldn't seem to find them which seemed to make Daddy Mike harder as he watched me bend over a lot to look for them, the heels he bought for me to wear during our play enhanci... Continue»
Posted by sublimeguy 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1505  |  
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transvestite in trouble 4 - the internet porn quee

Bright light filled the room, waking me from my unconciousness.

so bright it took a while for my eyes to focus. When they did the first site i saw was myself, in the wall sized mirror opposite me, strapped to the chair. It was me only now i had masses of long blode hair, tied up in 2 pigtails, loads of black eye make up and long false eyelashes, and big bright red lips. A new ball gag in my mouth, I was wearing a pink latex basque, white stockings and red slutty shoes, 6" heel with a 2" platform. I had on no panties, my cock was now locked in a heavy, metal chrome device, and there was som... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1173  |  
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First Time Shemale Encounter

Lets start off by saying this a very true story, one that i love to re-live over and over. lets begin

I was in el paso, texas..my girlfriend at the hotel. Something in me decided to go to the strip club. So i did. After a few dances, i decided to leave. I had always heard in mexico it was very easy to find shemales. So i decided to go over the boarder to the very dangerous city of Juarez. After i was in mexico i grabbed a beer and started walking. Within 15 min i noticed these beautiful women all standing outside of an apartment building. I walked over and proceded inside. Not kno... Continue»
Posted by iLoveShemales12 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2616  |  
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Job Opportunity

So. A bit about me. I'm 5'4", 139 lbs, long brown hair and deep brown eyes. 5.5 cock, cute 'bubblebutt'. I had been looking for a job for a long while with no luck, and REALLY needed the money bad. I finally got a call from the female owner of a coffee shop I had applied to. I had actually filled out one of the old fashioned applications. As in paper, not online. I had handed it to this owner and she just smiled and said nothing. I felt kind of weird about that smile then, but said nothing and just smiled back.

The owner was a VERY cute voluptuous redhead at coffee shop who was to 'show me ... Continue»
Posted by rockywhoreor 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1807  |  
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unnecessary roughness

Some years back, I was on an overnight business trip. I would often crossdress in my motel room to entertain myself and practice looking sexy. I could pass as a real woman from a distance but not so much up close. I'd been strutting around in a short a****l print dress and platform heels, admiring myself in the mirror and occasionally walking around outside my room in the motel parking lot. There was a convenience store/gas station next to the motel, and I kept walking over toward it, daring to be seen by people filling their tanks, etc. Late that night I decided that I just had to go over to ... Continue»
Posted by dana213 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 1167  |  
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First Time Dressed… at an Electronica Conce

I had been dressing as a girl to get off for some time now. For some reason there is nothing that turns me on more than a tight little cotton thong stretched across the bud of my asshole, holding my tiny little boy toy down where it should be. Over the years I’ve slipped into my mom and s****r’s underwear drawers while they were out and stolen the sexiest piece of clothing I cold find, most likely leaving them wondering where all their stuff went. This practice has gradually become a longer and longer as every time I do it I have a hard time taking the clothes off. Within the first few times,... Continue»
Posted by Cleveland2dc 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 840  |  
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A taste of Sandy

My phone rang and a husky feminine voice whispered I am here. Trying to hide my hard cock with my shirt I quickly went out to my hotel parking lot and found the Escape with a silhouette waiting. I walked up to the window and introduced myself “Hi Sandy, I’m Zef” Come sit for a minute sugar Sandy replied. I climbed into the passenger seat my cock straining hard against my shorts. Continuing were we left off on craigslist we talked for a few as I admired her dark nylons and pulled up skirt just covering her thigh. She had brown wavy hair to her shoulders, her eyes were covered with a blue shado... Continue»
Posted by Zeffer 3 years ago  |  Categories: Shemales  |  Views: 1279  |  
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Huddersfield fun (true story)

I had been to the Huddersfield porno cinema all day. I was sucking and wanking around 30- 40 guys in there. The guys like watching porn and then going into the rpivate rooms with me. I would suck and wank and then let them finger my sweet arse for hours.

As i left the cinema for a break, I walked onot the street and wanted fresh cock. I was bored of the middle aged guys all wankers sweaty and filty from masturbating for hours to hardcore pornographic films.

I walked down the back street and saw a guy i recognised as the local d**g dealer in the area. He was on bike and was often out in... Continue»
Posted by ritaboy 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1082  |  
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Courtney and Michael

I wrote this last Christmas Eve and sent out to friends who've provided me their email. I tried to include the photo that was the inspiration but couldn't get it to show ... it was stellar! So enjoy ...


"Oh Michael, you're company's holiday party is always so boring! Do we really have to go?"

"You know Courtney that I am expected to be there. I AM the Senior Vice President, after all."

Michael wore his typical grey business suit with a festive tie to the event. Courtney, a tall, shoulder-length blonde, wore a black mesh dress with black stockings and boots. The party was held ... Continue»
Posted by call_me_dana 3 years ago  |  Categories: Shemales  |  Views: 951  |  
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my first cock experience (true story crossdressing

I will never forget my first experience with another cock , it was the only time I have ever been with another man, now saying that I do date ts women, I love them as much if not more then I do genetic women. I was 12 years old and like any young boy , very horny . At that time my best friend liam and I would have sl**p overs and do normal k** stuff , sports , video games , camping , never did I think that one day I would have his warm milky cum in my mouth or his warm hard throbbing Dick inside my ass pussy .

It all started when we were looking at a magazine and saw a picture and article ... Continue»
Posted by dickissogood 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4912  |  
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saturday at the Park

Saturday afternoon at about 3PM I left a bar after lunch and a few drinks. On my way home I passed a park that typically is crowded but today there weren't many cars so I went back. In the park I saw a few people at the entrance but no cars parked in the back half.

I parked on the side of the road and I looked around once again and no one was in sight. I pulled my jeans and underwear off and slipped on panties and hose. I took my T-shirt off and slipped a bra around my chest. Snapped in on then spun it around in place. Stuffed my socks in the cups. Lastly I put on a silky slip and a dress. ... Continue»
Posted by Sigrid-DWT 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2830  |  
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My afternoon getting some(true story) BB creampie

It was a Sunday afternoon and I was emailing with a guy I just met on craigs list. I was having a few drinks while starting to get in the mood. We exchanged phone numbers had a little chit chat on the phone, he told me he was straight but always wanted to experience a TS. Well this is the type that I love to entertain. So we set up a time to meet and gave him directions. I quickly jumped in the tub to wash up, shave my legs, gave myself a enamma. I had a couple hours before my man would arrive so I took my time doing a really good job my makeup (especially we where meeting during the day time)... Continue»
Posted by sarahcd_legs 3 years ago  |  Categories: Shemales  |  Views: 1892  |  
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A Different Kind of Woman pt2

My hands were at one and eleven o'clock tied to the bed, the beautiful creature that I was so infatuated with turned out to be a shemale and I was at her/his mercy. Tiffany was working her/his penis up my butt with precision all the while stroking my penis keeping me rigid hard. Each time I thought I was about to shoot Tiffany would stop long enough for me to calm down.
Tiffany had called some body named 'Joliet' and told her(?) to bring 'Bambi' with her(?). Tiffany was having her/his self a fantasy come true pumping her/his penis deep into my butt, all I could do was grunt and groan with... Continue»
Posted by d4david 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1162  |  
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A Different Kind of Woman pt1

As I was leaving work, a car stopped at the corner in the drivers seat was the most sexiest woman that I have ever seen. She had a pair of breast that was to die for, and legs that seemed to stretch for ever, and a smile that would bend steel. She saw me looking at her, probably with my mouth hanging open, she smiled and sorta of waved than drove off. I could not get her out of my mind, when I got home I jerked off thinking about her.
Two nights later I was at the corner waiting for the light to change, the same car pulled up, as I stepped into the streets, she moved forward just a little... Continue»
Posted by d4david 3 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1267  |  
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