Shemales Porn Stories
Page 68

Island Fantasy

Part 1

My ship arrives off shore at about 10 in the morning local time. We drop anchor about a 1/4 mile out and busy ourselves with getting ready for some shore leave. I'm very excited because I've only been on the ship for about 3 weeks and I'm already getting to go to a new and exciting foreign country.
As I look over the sides of the ship I see a large crowd of small vessels starting to appear. They're locals, fishing boats, runabouts, and all of them loaded with people staring up at us.... at me.... I wave and they wave back. Friendly.

When its my time to depart the ... Continue»
Posted by SandyCrossdresser 1 year ago  |  Categories: First Time, Shemales  |  
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Missy's Revenge

Missy grew up in a very poor f****y, and lived most of her young years in the projects. Her f****y's small apartment complex was in one of the worst parts of town.

Missy's mother had left when she was only five years old and she barely remembered her. Her father drank every meal, and spent all of his money on alcohol. Missy and her s****r had to wear hand me down clothing, and were often un-bathed and unruly.

She rarely had time to play with the other c***dren who were mostly black. Once in a great while she would take a risk and steal some change from her fathers laundry, so she... Continue»
Posted by debra_young2014 2 years ago  |  Categories: Voyeur, Hardcore, Shemales  |  
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Magic Panties Ch.01 (Sissy story) by Nolfon

This story is a work of fiction, all characters are fictional and obviously the events are fake. You may reprint this as needed, just give credit to the author. Oh, and enjoy!

Chapter 1: Beginnings

It was a Tuesday night, and I had an anonymous date with a self titled freaky gal that I met online. The time was 8pm and she an hour late and I was pretty pissed. I was stood up by another girl. The whole female gender pissed me off these days. They never wanted to get to know me, or they were so selfish it pissed me off. The guy next to me at the bar looked over and saw my sorrow. He bought ... Continue»
Posted by bqreus 1 year ago  |  Categories: Shemales, Taboo  |  
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Luckiest night in my life!

So here i was, off work, and hoping to find some fun online.

I had posted a couple nsa ads, replied to a few, and gotten no replies. But then this gurl amber told me she wanted me asap. I'm always eager and ready to go, so i hopped in my car and headed over right away. When i got there the bathroom was closed in her hotel room, and there was a pile of clothing all around us. But the bed was clear and that was all that mattered. She grabbed my hands and started kissing me. While sucking on my lips, she pulled me on top of her on the bed, and put my hand on her crotch. Under her nighti... Continue»
Posted by kevlar20 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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Caught dressed

I had been dressing for a while when I got married. I had enjoyed my time dressing and especially when I would go out of town.

One trip I took I got hjome and was called to go help a friend right away. I left with out unpacking my bags. I really didn't think about what I had in my bags when I left the house. When I came home I went into the house and I found a note that said I will be home soon I have a surprize for you.

I went into the bedroom and remembered what I had in my bags. My clothes and under them were my sexy clothes. I had panties, hoses, garters, crotchless hoses, heels and... Continue»
Posted by pamcd 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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the train ride




The Train Ride

Has anyone taken a night train following a major event in an
Asian country? I have. If you think trains are crowded during
peak hours in New York, you must experience riding trains in
Asian countries. Then you may ask what is common between a
crowded train in Asia and a can of sardine.

The idea to see the festival was planted in our minds by George,
who was our bartender at the hotel. He stated that the Kandy
parade was a once in lifetime experience, two days before we were
to head back to Oslo. After hearing what we were about to miss,
we made plans to hit... Continue»
Posted by pcarter 3 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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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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Turned into a Toy

I clicked the lock shut on the locker containing all my clothes and looked down at my now naked body. I was in very good shape for a fifty year old. I'd always been thin and now I was shaved from the ears down and all six feet of me looked smooth and toned. My cock was a bit tumescent, larger than average and some found this odd for a complete submissive and was often disappointed when I didn't let them play with it, but I preferred to be always aroused when I served others.
I placed a towel around my waist. There was an odd clicking sound behind me and a soft lilting voice spoke, "And whose ... Continue»
Posted by kbking64 4 years ago  |  Categories: Anal, Fetish, Shemales  |  
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The Lindy Factor

When I walked in the first thing out of the ordinary was the cute little blonde sitting on the couch with all her books all spread out next to her and she was typing in her laptop. She stopped and moved an index card so that she could read it better and then noticed me.
"Hi", she said. "You must be Steve right? I'm Lindy and I'm in a couple of Julie's classes. She invited me over for dinner, I hope that's ok?"
I assured it was and I went through the small living room into the kitchen where I could hear Julie making supper. I walked quietly up behind her while she was washing something in ... Continue»
Posted by subjaye 10 months ago  |  Categories: Fetish, Shemales  |  
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gay sex with 60 years old man in chennai

Hi I'm ashwin, about me IM FAIR AND SLIM HAIRLESS BODY MY AGE IS 23. I LOVE GAY SEX CD SEX AND STRAIGHT SEX. TOTALLY IM A PURE BISEXUAL GUY THATS WHY I ALWAYS WEAR RING IN THUMB FINGER. BOYS OR GIRLS IF YOU WANT A HOMO SEX PARTNER THEN WEAR A RING IN THUMB FINGER AND MIDDLE FINGER, LEFT HAND OR RIGHT HAND IT DOESNT MATTER.....here is my another true story which happened 2days back. As I told you in my last story I'm a call taxi driver in chennai. Before 2 days at morning I got a trip so I reached there to pickup my customer. I called him and said I reached so u can come sir, he said OK I'll co... Continue»
Posted by Ashwinchennai1 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Wifes friend

Johanna had invited a friend to stay over the weekend. Her friends name was Lorenzia. She was from Chile and had a natural tan skin. She was a fitness geek and was extremely fit. She had thick black hair that she keept in a thick ponytail down her back. She had a wonderful ass and a c-cup sized breasts.
Johanna had to leave for work one day so I was left alone in the house with Loraezia. She was working out in the living room, lifting weights that would break my back if I tried lifting them.
she was dressed in a sports bra and tights. I looked as the sweat ran down her neck and back, over ... Continue»
Posted by Ankakalle 3 years ago  |  Categories: Shemales  |  
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My best ever day

Okay. I'm not a stpry writer but I think my experience was hot enough that it may keep your interest.

I was 19 and I was on a training course for my new job. I had knew 2 weeks in advance where I was going so had started looking for mistresses in the area online. I didnt contact any but saved the numbers of my favourites in my phone.

I arrived late the first night, slept, went to the course then went home and got ready. I had a few glasses of wine then dialed the first number. Part of the fun for me was not knowing which one it was.

After a ten minute chat about what I was looking for... Continue»
Posted by LauraJaneXoX 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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Sissies Feminization and Hormonal Transformation t

I was 39 years old and I have been a female inside a mans body. I've dreamed of changing into a full woman. Yet I got married, and had a wonderful boy. I asked my wife one night what she thought of being with another man, & was very upset. I continued to explain how I fantasized about being her cuckold an being feminized completely including hormones, body modifications, and living as a female on our Jamaican vacations were she could fuck, suck, and eventually be impregnated by a BBC. She said I was disgusting, and shed never do BBC. So I continued with a very WEWC, and detailed his thickness... Continue»
Posted by briannasissycuck69 5 months ago  |  Categories: Interracial Sex, Shemales, Voyeur  |  
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SISSIES TRAINING PART 2

SissyIndy©

I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by the sight of this brunette in a pink corset and black stockings leading down to her pink high heels being pounded by this horrid machine from both sides. Knowing that the slut in the video was me, a man f***ed to wear these whorish clothes and caked on makeup with a brunette wig bounci... Continue»
Posted by stig1963 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Internet acquaintance

When I once again was bored and surfed the internet looking for some fun, I found the following ad: “Experienced and dominant master is looking for a young, unexperienced and submissive TV. You should be slim, shaved and very feminine. If you are interested, fill out the added form and send me some pics of you.” I found the text a bit short and I was disappointed that there were no photos of the man. Nevertheless I became curious. The text exactly applied to me. Already a bit excited I filled out the form, where I had to state my body measurements and sexual desires. I attached some slutty pi... Continue»
Posted by notgeile_fickstute 1 year ago  |  Categories: BDSM, Gay Male, Shemales  |  
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My highschool girlfriend 2

It had been a week and me and my girlfriend had not done anything else, but ofcourse we talked about it. Her mostly, saying "I was so sure you were so strait, im so happy your okay with my cock" all I would say was "I was so sure I was strait too, but being with you, just changed that I guess but I love it, you make me hornier than a girl with a vagina ever could." She also brought up another point, that the anal can go both ways, and ask if she could be on top next time. I was kinda scared it would hurt, but thought it may be fun, and told her that and she said she would make it painless, by ... Continue»
Posted by suckmedry69 5 years ago  |  Categories: Anal, First Time, Shemales  |  
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My firs time as a crossdrese

Hi,i am 19 and i have always liked wearing womens clothes.While wearin them i always imagined there was a nice older guy fucking me and cumming on my face. After a while i decided to try my fantasy for real. I got in contact with an older men and we decided to met. He said that he would come for me in a car and that we will go to his house and have a lot of fun. I was so nervous and could hardly wait to meet him. The next day i was waiting for him at a spot where we arranged to meet. He came in his big black suv and opened the door and said to get in. I got in and sat next to him. He had dark... Continue»
Posted by nikoletakurva 5 years ago  |  Categories: First Time, Mature, Shemales  |  
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Masturbating on the Airplane... Sort of

I was on my way back from Boston after a torrid night of partying. I was tired and it was early in the morning; I really felt like I had JUST gone to sl**p when the alarm went off to go to the airport.

I threw on a long t-shirt, black panties and leggings, my boots, and a red pull over, since it was cold. I hadn't brought much with me so I would not have to check a bag. The cab took 25 minutes to get there, and I was standing at the gate charging my phone for nearly an hour.

My mind kept wandering back to some of the shenanigans from the night before. The faux lap dances we were giv... Continue»
Posted by noellejordan 4 years ago  |  Categories: Masturbation, Shemales, Voyeur  |  
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new job fantasy

I was pretty nervous as I looked at myself in the mirror and put the final touches on my make up. Not only was this the first day of my new job, it was the first time I would be working anywhere in full femme mode. I’d spent the last few months perfecting my look, my walk and my voice. The hormones we beginning to kick in and my cute little tits looked perky. I fact I’d been passing successfully for a while now, but still this was a big step.

I did a last twirl to check my self out.

“Not Bad”, I said. My red hair bounced at my shoulders and crimson lips we plump. The knee length skirt I ... Continue»
Posted by cinful6767 2 years ago  |  Categories: Fetish, Hardcore, Shemales  |  
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First time dressing up

I was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my s****rs clothes. I went into my s****rs room when the house was empty and opened up her closet. I saw all of her nice shirts, blouses and dresses, i looked around pulling some stuff out and eventually made my way to her dresser and saw all the panties and bras. I wanted so badly to try on a whole outfit but i was terrified of getting caught.

Then i got an idea. I picked out the clothes i wanted... Continue»
Posted by Badassgirl123 1 year ago  |  Categories: First Time, Masturbation, Shemales  |  
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