Shemales Porn Stories
Page 59

Sissy Mailee's first black cock - part1

As long as I could remember I have always had a craving for black cocks. My first time was a few years ago after partying with a friend of a friend.

I had called up one of my CD friends, Suzy, to attend a Halloween party at a local warehouse. We had agreed that we’re both going to the party as slutty school girls. We met up at her place to get dress together. When I arrived at her place she told me she can’t go because she was coming down with the flu. There was no way I was going out in public for the first time by myself. I was super disappointed but she told me that her friend Brad woul... Continue»
Posted by aznfemboi 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Thougt i could fool the staff

Realized this day would go on so decided to go buy lightbeers an two packs of ciggarettes..

Uppon arival i smoothly asked two female store attendants where i could find makeup.. yeah sure over here, they where holding back giggles i swear and as suave as james bond i just flat out lied someone is gonna look really pretty for his birthday! (u know im just getting supplies) then i asked them about what i thoght was foundation and they wher like yeah u use it to blabla and i said yeah just wanna make sure i got this note with me im not al so sure of what everything is...
So far so good..
... Continue»
Posted by tinyswede 1 year ago  |  Categories: Sex Humor, Shemales, Taboo  |  
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Cow Girl`s got something hard in her jeans

Last Friday night me and the guys from work stopped to have a couple of beers. which of course turned out to be a whole lot more. boy was i going to be in trouble when i got home. but when i got home it was all quite, too quite. then i saw the note. "You son of a bitch you knew we had that dinner at my mother`s!" i knew i was in big trouble now. being a little d***k i thought hell with it i am going to have a good time any ways. so i put on my boots and grabbed my cowboy hat and headed to the bar to do a little country dancing. as i looked around i noticed a nasty looking blond on the other ... Continue»
Posted by manard 4 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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AdDicked to porn

Hi is Peter home. Sorry just me come on in. I wonder where Peter is but who the fuck is this babe? I'm Peters cousin in case you were wondering. My name is Julie and you? Ah Tim, I was blown away at how pretty she was. But its so warm why are you wearing a robe, I mumbled. Silly boy I only have on my new undies, I was trying them on. Oh sorry to intrude, I backed up but she stopped me and said how would you like to see them and let me know if they look good on me.

Sitting down in front of Julie she strips off the robe. My cock likes the undies. She had on soft silk stockings with a nice pri... Continue»
Posted by TenderLoins 1 year ago  |  Categories: First Time, Shemales  |  
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Adult Video Store #2

I got up and walked into the next room as she closed the door behind me.

I took a second to look around the room. First I noticed the desk she had been leaning against when she first appeared on the tv screen. Looking to my right, I saw a nice camera on a tripod. Behind it was another desk with more camera equipment and a computer with a large monitor. On the monitor, I could see the room I had just been in. The chair I had been sitting in was clearly visible in the center of the screen. I had a feeling, while I was in the other room, that she was able to see me somehow. Now I knew she had ... Continue»
Posted by naughty_bi_interest 8 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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My Evil Landlord..

This is my 2nd true story of my transexual life and the things that have happend to me in it. I moved into my own flat when i was 17, i needed the space away from my mum who was always drinking and getting fucked by strangers who she would bring back after a night out, many a time id hear the bed banging in her room and her screaming out a different mans name at night. Id find wet cum stains on her bed during the day or a pair of her panties lying somewhere that she had thrown and forgot about in her d***ken state. Always id find that the gusset of my mums panties were wet with mens cum and i ... Continue»
Posted by cinderella88 5 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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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 5 years ago  |  Categories: First Time, Shemales  |  
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Working Away From Home

Im an engineer by trade and my job sometimes takes me to different parts of the country, customers want me to design a specific peice of machinery for them.

I had an appointment with a firm just on the outskirts of Manchester, my company had booked me into a nice hotel for 3 nights whilst i was up there.

After my first days work i went back to my hotel and had a shower, got dressed and set out to find a nice restuarant for my evening meal, the consierge had suggested i went a particular restuarant that he new and gave me directions.

I got there it seemed very nice sat down at a table ... Continue»
Posted by BAZSEX 4 years ago  |  Categories: Gay Male, Shemales  |  
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Would I be happy if I could remember...

My story began a few years ago when I was in college. My roommate decided
to let his girl move in with us and although it is annoying working my
schedule around their love life, she was very hot and I didn't mind the
occasional show when she would run from her shower to their bedroom. I have
to admit. My roomie was a lucky man. That girl had to have the nicest
breast on campus and an ass to die for.

Eventually as most love stories go, things fell apart
between them she had somehow talked my roommate into moving out. I should
have known she wore the pants in that relationship. How do... Continue»
Posted by urgonnaputthatwhere 3 years ago  |  Categories: Anal, Fetish, Shemales  |  
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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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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 3 years ago  |  Categories: Fetish, Gay Male, 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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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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My wife introduces me to submission and cuckoldry

The next morning after an early breakfast my wife and i set out for Jeanie's house, on the way i asked her what she would be doing for the day and she said that she had some stuff that she needed to buy and that i would be more use helping Jeanie out than moaning about shopping as i usually did. I nodded and said what is Jeanie like as i would be spending several hours in the company of a woman that i had only met for a very short time. She thought for a while before answering me and said that Jeanie was a lovely woman but a woman who didn't tolerate fools, that she had a sense of humour, but ... Continue»
Posted by oldognewtrix 1 month ago  |  Categories: BDSM, Mature, 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 4 months ago  |  Categories: Fetish, First Time, 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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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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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 4 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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