Shemales Porn Stories
Page 59

At Jake's Cabin

Jake and I had been secretly seeing each other for about a year. We took every chance we could get to go and fuck. Jake’s famly had a cabin on a private pond in northern Minnesota. He had asked me to go up there with him for spring break. He told the fam that it was a guy’s weekend to fish and drink. It would be just us two up there the whole week. We did do some drinking but we fucked instead of fished.
We stopped at a small town just south of the cabin, probably about ten minutes away. He went into the convenience store to get beer and food. As he was in there I got into my bag and pulled ... Continue»
Posted by taylorbaby 4 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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How I got caught!

I had a day off and I was on my computer looking to see if anyone was on to chat with. I didn't see anyone and was about to close the page when a message notice flashed "Do you want to chat?" I said sure I would love to. The first thing he said was I have been watching you when you use your web cam I am very interested in a private veiwing!I was not sure how to respond to such a quick demand. I had never had anyone respond back when I have been using my cam.

The question now was what do I say or do. Soon he was asking are you there? I answered back yes I am. He said well what will it take f... Continue»
Posted by pamcd 4 years ago  |  Categories: First Time, Shemales, Voyeur  |  
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Gina's Thank You Surprise

I get pretty excited when my company sends me to Cincinnati for the week. I think my wife can sense something and I have been getting a little nervous she might be catching on. Over the last year I have made the trip seven times and on the first trip I met up with Gina a nice 35 year old CD I friended on Xhamster. We started out slow and met for a quickie but the last couple of trips we spent the entire night together feeling more comfortable and excited with each meeting.

Gina has always met me at my hotel, but this time she invited me to her apartment. After my nightly call home I jumped ... Continue»
Posted by iheartm2f 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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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 3 years ago  |  Categories: Gay Male, Shemales  |  
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From Femboi to faggot Madison

From Boy to faggot sissy Madison

I meet Maddi Ng one night as I was heading back to my hotel form a sales meeting. I noticed this young lady walking down a dark street while being followed and heckled by 4 thug looking guys. I pulled over and asked her if she needed a ride or to use my cell phone, she jumped in so fast I thought she was going to rip the door off my suv. As I drove away I looked over and noticed that she was actually a very feminine boy. I asked “what was going on” and she whispered “I promised to meet those guys for some fun but chickened out”, I asked “why would you want ... Continue»
Posted by BigDaddyJSubStable 3 months ago  |  Categories: Fetish, First Time, Shemales  |  
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How My Wife Found Out I Was A Slut

I was fucked by many men before my teens, but that is a whole story unto its self. When I was about sixteen my mother took ill and I was sent to abode with my grandparents. I had many dates with the hickory stick and soon learned to act like a man and suppress my desires to be with men.
After high school the government required my services in the military— I did look dashing in a sailor suit. It was during this time that I meant and married my wife— still suppressing my female desires. Within the first year of our marriage we were swinging with other couples and other men.
Soon we were m... Continue»
Posted by littleoralvee 2 years ago  |  Categories: Shemales  |  
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I went back for a male massage....

After my last visit, as I said my head was spinning...I'm not gay, but I loved being used that day...have a cock in my mouth and in my ass??...but, I loved it...so here I was again...when I went in, I didn't see the same staff...it was asain women this time...???...ok, this can still be fun but...A very sexy asian lady asked me if I wanted a massage...she was smokin...great face...nice tits...very short dress....hmmm....but her voice??? a little deeper than I expected....
I undress in the room and wait...a few minutes later "she" walks in and as she walks to the head of the table, she runs h... Continue»
Posted by clvsdude 4 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Serving Waitress

This is the first “didi” story I ever wrote. It’s my deepest (and darkest?) fantasy. It probably needs to be rewritten at some stage because I think it’s been written too much by my male brain and not enough by my female side.

The story begins…..

My wife, Susan, one evening announced to me that we had been invited to a party at a new friend of hers. Victoria had inherited a fortune from her father and she lived in a mansion in the best part of town. It all sounded very exciting. Apparently she had these parties once a month. Susan said that we would go earlier as she had offered Victoria... Continue»
Posted by didi_galtier 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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its monday night football

HELLO EVERYONE
I hope everyone enjoy my last story happen on black Friday please leave comments so I know how much u love the story thank you

Well we getting close to football playoff and every other Sunday some one throw football party at their place sometime I get invited sometime I don’t depend what kind of party and what kind people their as you know im a pretty shemale and im proud of it.
My story always a real experience happen to me or my friends I love to share after all us shemale also have feeling too

On Monday night football Texans vs patriot one of black gay friend throw th... Continue»
Posted by shawn777 3 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
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Ladyboy DP for Thai Wife

I opened my eyes and lay still in bed, awake unusually early. I could feel the warm presence of Noi snuggled up in bed bedside me. She was sl**ping face down with her little bottom next to my right hand. I reached out and touched the warm butt cheeks of Noi's tight and shaped ass. I gave them a fond little squeeze and felt my cock stirring with desire.

Noi was your typical lovely pleasure loving Thai woman, very petite with a slender shaped body and girlish hips. She had lovely soft silky brown hair and a wonderful pair of red lips that were delicious to kiss, as feel heavenly wrapped arou... Continue»
Posted by sanpeesua 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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my gardner plowed me

My wife and daughter had left to spend a week with my mother-in-law in Brazil. So it was time to breakout my secret wardrobe. Having two women in the house made it easy to keep a sexy supply of clothes. Add a wig and some makeup, I'll soon be lookin pretty hot.

I started by shaving my body and taking a long hot bath in some lovely smelling bath oils. Just the thought of dressing up was making me wet. I dried off and went to get dressed. Being in a wheelchair made it take a long time to get dressed. I wasn't even going out but I wanted to dress up and maybe video chat with some hung studs, ... Continue»
Posted by cdaisy1 4 years ago  |  Categories: Shemales  |  
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The Fuck that would never end

This is a short story k?
I went to Italy to visit my cousin Lance and he showed me around and some of the guys hit on me but when the day was over i layed on the couch and fell asl**p...
about 3 hours later...
I woke up on a stool tied up and saw my cousin nude infront of me with a HUGE COCK! and he said,"Well well....the fuck slave finally woke up..." I tried to speak but i realized that a gag was in my mouth i looked aroun i could only see Lance,the lightbulb,and darkness around me.
All at once 3 white guys about 7 inch each (not counting lance) all slapped their dicks in my face.
after... Continue»
Posted by FuckmyhornyAss 4 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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The Perfect Woman, Plus (Part I)

This is the 1st part of a 3 parts story. It is not mine but I hope you like it...


The week my girlfriend Monica broke up with me, I had to fly to New York City for a convention. I must admit, my mind wasn’t on business, and the first chance I got, I went to the hotel bar to drown my sorrows. The bar was fairly empty, which was O.K. with me, since I wasn’t really in the mood for conversation anyway. I was half-way through my first pint of Guinness when the cocktail waitress brought me another glass.
“Hey,” I objected. “I didn’t order this!”
“Relax,” the pretty brunette said. “It’s fro... Continue»
Posted by freegre 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Teen pussy of 18 years in bathroom stall masturbat

Certain noises merge from a closed bathroom stall door which you well know are only from a girl pleasing herself, so it was no surprise to myself, a shemale, who uses the girls room very discreetly, to hear such moaning 2 days ago in the bathroom stall of a store in the local mall. And since i jack my cock off in those stalls also and spurt my jizz, it is always a thrill to hear another girl moaning, even so slightly, with pleasure as she fingers her wet pussy. Thus, i literally stood next to the door and wham, it was not locked, guess she wanted to be watched, so i went in and she just smiled... Continue»
Posted by cumsquirter 5 years ago  |  Categories: Shemales  |  
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Shemale on wheels tour

Being a sexy naughty city girl like myself…I get allot of attention from the boys. I always enjoy getting the attention of the small town boys that are not used to seeing a sexy bitch like me roll though town. They jerk off to girls like me online all the time. But having me right in front of them sometimes makes them overwhelmed and easy targets and my prey… lol.

For me, I love sex. I enjoy the attention of men and I love being used by a man. But the biggest turn on for me is finding some dumb straight boy and wooing him with my big tits and dropping to my knees and having him give me a go... Continue»
Posted by tashajones 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Surprise!

Here I was, on a Sunday night, going in the club to have some fun.
After few hours of dancing and drinking, one pretty girl came and asked me to dance with her. Looking at her I saw that she`s not a "grenade" so I was thinking maybe I will have some fun tonight so we started dancing. After a while I started rubbing her ass, then I kissed her...OMG she was such a good kisser.
After she broke the kiss she asked me to come to her place and I was so excited that i took her hand and put it to feel my boner.
She gigled and we start walking to her place.
As soon as we arrived..i couldnt stop ki... Continue»
Posted by mercander 4 years ago  |  Categories: First Time, Sex Humor, Shemales  |  
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f***ed to cross dress on Halloween

Halloween is a great reason to show your submissive side and cross dress for your mistress. Other than writing these articles and stories, I also enjoy dominating my partner.

This Halloween was no exception and I wanted to share this exciting day with you. Below you will find a story that is heavily based on the events that took place in my house this year.

***

I could tell he was anxious. Informing him about the Halloween party raised a lot of questions on his end which I skillfully either ignored or diverted.

I had not been mean right from the start, but I clearly told him he had... Continue»
Posted by lokokolo 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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The best s****r ever part 5

Yes this is all true. please read from the first stories.

The next morning I woke up and we had all slept in our parents room and my cock was still in moms pussy while i had dads cock up me as well. Me and my s****r both went ownstairs and had a sandwich and another fuck before mom came downstairs to leave for work. When she came downstairs my s****r came in my mouth and I came in my moms mouth nd we swapped cum as she kissed me goodbye.

It is two years later now and we are all above age now so nobody could look down on us outside the f****y for having sex. I had taken a course in the lo... Continue»
Posted by horndogs 4 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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Willows transformation 1


Fern and I had been married for three years. Our sex life had become bland, routine, and, frankly, I preferred masturbation to the work it took to cum by intercourse. I was pretty sure that Fern felt that way, too. You see, my cock is, at best, 5 inches. My touch, or my tongue, on her clit seemed to be much better received than my cock inside her.

I've always been a cross dresser. I can remember being in first grade and wearing my older s****r's clothes and pretending I was on a date with a boy. Before we married I told Fern about this. She treated it as something that would go away once ... Continue»
Posted by stig1963 5 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Jason's Joy

Mum had asked me if I would look in on her half b*****r Jack. He hadn't been in touch for a couple of weeks and normally will contact his s****r twice a week. On a Saturday afternoon I would normally meet with friends in town. I call them friends, but I am a bit of a loner and I hang around the fringes of a group of lads. To get to Jack's house means crossing through town. Now that i have my scooter it takes no time at all.
I arrive at Jack's house and I find the curtains are drawn. No windows open despite it being a warm afternoon. I knock on the front door but there is no response. The side... Continue»
Posted by dasilva1672 2 years ago  |  Categories: Mature, Shemales  |  
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