Shemales Porn Stories
Page 59

First time glory hole part2

...... I woke up and the lights were now on so I was guessing it was night and they close this place at 12 so was hoping that the man who closes it down let's me go so I looked at my watch it was 11 so was hoping someone would come soon.

Someone came in I guessed it was the cleaner cos he went into the other stall and sounded like he was cleaning so I was hoping he will let me go he had finished cleaning the other stall and then open the door to the stall I was in he looked in shock to see me sat there with no trousers on after being shocked he looked round went to the main door and shut it... Continue»
Posted by briggs123 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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three gets crowded

I was over at a 'friends' house the other day. Just relaxing on the couch snuggling up to him watching TV. His couch is halfway between a full couch and a loveseat. He is also a fairly large older man (in his 50's, around 6'2" and weighing between 240-250). Just how I like my daddies :)

I was wearing a simple outfit. A nice colorful skirt that went to my knees and a simple blue tank top. Plain, but comfortable. He had one hand around me, and was running his hand across the skin on my arms when the doorbell rang. I quickly got up and answered the door. It was his friend 'Jim'.

... Continue»
Posted by zaria_ts 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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Tgirl Hooker pt3

All my stories are based on my experiences

I’m sure most of you have read The Tgirl Hooker pt1 & pt2 with Emma who I found on a well known website. Pt 1 & pt2 was about my very first meeting with this Eastern European beauty who had a body to die for and a cock to match. I used to get the odd text from Emma every now and again asking when was I coming to see her, which then led to us chatting a bit and then as I got to know her, we then started to text or chat online nearly every day. I bottled up the guts to ask her out for a drink... one where I was not going to be charged by the hour a... Continue»
Posted by dirtydisco99 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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The Portal Part 1

Figures streamed across Jim's screen, highlighting yet another problem with the accelerator. Dr Jim Smith was one year into his 3 year program at CERN and things were not going well. The results from the detectors were way off the predicted scale and Jim would have to delve into the machinery once more to ascertain the problem. "Pass my safety hat Stewie" Jim asked as he grabbed his tools from the case on the floor.
"Should I re-set the experiment Dr Smith?" asked Dr Stewart Jones, as he passed the safety hat to him as requested.
"Yeah, re-set it Stewie and we'll give it one more go befo... Continue»
Posted by dekkard69 1 year ago  |  Categories: BDSM, Gay Male, Shemales  |  
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this year Dr. visit

My Annual Dr'S Visit 2014

i guess I'll describe this years visit and if you like reading them I'll continue to describe my annual Dr. Visits. I've been seeing the same Dr. and his Nurse for about 4 years now. The first one was mostly normal however the last two previous ones have been kind of embarrassing for me and I wondered how this year's would be. I made my appointment and and as usual the nurse came to the waiting room and got me and took me back to the exam room. She had me go into the changing room to put on the gown . I took off my shorts and top exposing my bra and panties like ... Continue»
Posted by sissygirl 1 year ago  |  Categories: Gay Male, Shemales  |  
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Bad Habits CD Fantasy

Why did I keep making bets like that, was the only thing I could think of while in line. Why did I keep making bets I was destined to loose, and then have outcomes like...well, this. I was standing in line to go to a cosplay convention, and was in full costume, but of the wrong gender. I was dressed up as one of those Vocaloids, with knee length blue pigtails, A black skirt that was barely at my knees, a set of black and blue boots that went up to my thighs, a sleeveless vest like shirt, a weird belt thing, weird glove-like sleeves (that left my armpits and upper arms open for the whole world ... Continue»
Posted by RosalynLee3 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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Never Wanted To Be Your Girlfriend Ch. 04

8:20am Monday Morning

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"...You can't be serious, Mike. There is no way anyone is gonna believe me," I whispered intensely.

I was sitting in the school office dressed in the patently ridiculous outfit Michael had picked out for me that morning, waiting to see the principal over my "disruptive" behavior. I just glared open-mouthed at Mike as he patted me on the head and smiled.

"It's gonna work great, Andi. Just trust me," he said, and then walked out of the office.

I watched him walk down the hall back to class, and it was then that I saw my mothe... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales, Taboo  |  
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Never Wanted To Be Your Girlfriend Ch. 02

So, after being made up like a slut, left glued to a pair of silicon breast forms, and caught sucking-off my best friend, I was pretty sure my day couldn't get any worse, but I had come nowhere near the end of my torment, as Michelle now had something else planned that I was probably not going to like.

Brittany got all tarted up to go clubbing with her friends. Michelle and I ordered pizza, flirted with the delivery guy like a couple of teeny-boppers at a sl**p-over, and killed time by playing video games. I got my ass kicked more than usual because I couldn't stop staring at my reflection ... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales, Taboo  |  
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Never Wanted To Be Your Girlfriend Ch. 03

Derrick really took advantage of having me captive that first weekend. He spent the entire time making me watch porn videos, and then had me recreate the scenes with him. He said, that he needed his girlfriend to be fully versed in all the ways he liked to be pleased. His appetite for sex was unreal. The only time we ever really took a break was to eat. And I have to admit, he made the most amazing strawberry milkshakes to go with the food. It was almost worth the humiliation of being fucked sideways by my best friend's b*****r just to get those shakes.

By Sunday night we were both exhauste... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales, Taboo  |  
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Daddys little helper 2

I was in shock. I had just watched a video of on my father's computer of my dad and my best friend Sam on the very bed I was sitting on. My friend was dressed in sexy pink lingerie and had sucked my father's dick until he had exploded all over Sammi's (as daddy called her) face. The pair of them had very obviously enjoyed the experience.

That wasn't what had really shocked me though, the shock came from a couple of things. The first was that as my father had unloaded his come all over my best friends face, I had been thinking that it should be my face that was receiving his tribute. The oth... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales, Taboo  |  
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Daddys little helper 3

My heart was still racing as I stood up, pulled my underwear back into place and walked into the bathroom. I used a facecloth to wipe away the cum that had spattered my chest and neck when I had lost control watching my father and my best friend have sex.

I hurried to my room and picked up a memory stick and returned to my father's room. I plugged the stick in and copied the folder onto it. I put the laptop back in its place, gathered up my clothes and walked back into my bedroom. I lay on top of the duvet and put my hands behind my head and tried to process what I had just seen and heard.
... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales, Taboo  |  
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Never Wanted To Be Your Girlfriend Ch. 01

So here I sit, waiting to hear what will become of me, and I can't help wondering how the hell I got here. I know how it all got started. And it was all Michael's fault --

Michael and I met my first year of high school. We were both the smart nerdy types. And at around 5'6" and just over a 100 pounds, with long hair neither of us were exactly the jock type. Michael's dad split when he was young. His mother remarried, but his step-dad Brent spent most of his time in China running some sort of import business, so his Mom, and older siblings, s****r Brittany and step-b*****r Derrick, pretty mu... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales, Taboo  |  
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Daddys little helper

Maybe if I'd minded my own business and stayed off my dad's computer, my life would have been a whole lot different. As it is I wouldn't change it for the world.

My name is George Mason Jr. I was twenty years old when I moved back in with my father (George Snr, obviously) after my mum left him and took up with some arse-wipe she met at her gym. He had been devastated by the betrayal and I had moved back in to keep him company and make sure he didn't do something stupid. I was quite a good cook and a bit of a neat freak, so it worked out okay for both of us. I got out of my shitty one bedroo... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales, Taboo  |  
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my second time

after failing to loose my virginity,i decided to try again. my man friend love to fish and would make his way to inch early every sat morn. being a creature of habit he always returned at the same time. one sat evening i accidently on purpose bumped into him on his way home. standing at the side of the road he stopped and offered a lift. knowing rightly what i was doing i told him i was just out for a walk. asking if i was ok after our last encounter and seeking reassurance, i told him that i really would like to do it again.he told me that he hoped id say that and he had a surprise for me at... Continue»
Posted by smw1970 1 year ago  |  Categories: Fetish, Mature, Shemales  |  
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First Time Crossdressing with a mate part 1

This is a work of fiction, though someday I hope to make it a reality.

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It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I dressed up like a slut for the first time, I couldn't stop thinking about meeting another crossdresser for some horny mutual fun. I had been faithful to my girlfriend, but after that halloween party where she dressed me like a slut, I realized that there was a whole side of me yet to explore that lay untapped. My partner knew I was bisexual, and was into me crossdress... Continue»
Posted by obm_cd 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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Another Lawrence.

The other Lawrence

I was working on the top floor of a block of flats, it was a neglected old block that had a bad reputation. I knocked on the door of a flat that I had to repair a kitchen in. A guy anserd in his pants and let me in. The flat was dimly lit and unkeept ,it smet of smoke and musty sex. I had a few jobs to do so I got to work. I was on my knees in the kitchen working on the floor. It was so hot in this flat i was sweating. He walked in and put the kettle on. He stood with is crutch inches from my face. I noticed his cock getting bigger in his pants. I Couldn't take my eyes of... Continue»
Posted by ofluffy2 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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The Tgril Hooker pt2

All my stories are based on real life experiences.

As I left off.....

Emma pulled the toy out of me and said "I want you on all fours and ready yourself for a extra surprise...."

I was still blind folded and as horny as hell, Emma had so far made me feel amazing and I think due to being blindfolded it had almost given me double the pleasure and the darkness had added an extra thrill of never really knowing what was going on.

I got on to all fours like instructed and I could feel Emma behind me. Her cock was thick and long, maybe the thickest I had ever had and now I could feel it ... Continue»
Posted by dirtydisco99 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
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The Tgirl Hooker

All my stories are based on real life experiences.

I spent a few weeks looking at e****t sites, reading reviews, services, likes & dislikes, pictures... until Emma caught my eye.

Emma was Eastern European, had a tight slim body, blond hair, very fem and a nice cock. I wasted no time and contacted her to set up a visit and within a few hours she replied and we discussed what I wanted.

The day soon arrived and I was quite nervous through excitement. I had visited e****ts before but never a Tgirl. I pulled up to this house in a normal road and knocked on the door, and there stood Emma i... Continue»
Posted by dirtydisco99 1 year ago  |  Categories: Anal, BDSM, 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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BIG changes happen on Fridays ;) continued

Friday 11/4/07 Continued

After doing my duties around the house I moved upstairs and lying on my bed was something that took my breath away it was a dress my first proper dress (Mistress Isabella had given me many dresses before but they were never very ladylike they always carried a message with them that I was her plaything a doll to be played with and fucked at the drop of a hat) a real dress I picked it up and held it against me it was a soft red satin Square Neckline mini Cocktail Dress with long sleeves it was perfect I knew what to wear with it instantly I grabbed my favourite pair ... Continue»
Posted by Sissy_Kara 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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