Shemales Porn Stories
Page 82

Becoming a Princess Part I

Well, I figured since I havent posted a story yet it was about time I did. This story is for the most part fiction. But has some fact in it about me as well as partly being based on an experience I once had. Some parts that are fiction will be slightly obvious. But I know some of it could work in reality even if its a little out there. I may write an “extended version” in the future. Or maybe “directors cut” would be a better term. I will be compressing the story because I think if I were to go into exact detail with every part, writing the whole thing would take me several days. And I just do... Continue»
Posted by want2bespoiledutcd 3 years ago  |  Categories: Mature, Shemales, Taboo  |  
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Transformation

This is a cross between real life and fantasy. A deep, dark desire which may never be fulfilled but I can't help a part of me wanting it anyway. I hope you enjoy.

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I was a usual guy. Or I had thought so anyway. I mean, I had worn some of the female members of my house' panties and swimsuits on occasion as a young boy but I always thought that was normal. I mean, apart from the silky smoothness of lace and satin massaging and teasing the penis, y-fronts are exactly the same really... just with less frills. It didn't last long though, I mean, how can a boy in a strict and straigh... Continue»
Posted by shyadam89 4 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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0047 Femboy Camp – Nick

0047 Femboy Camp – Nick

Phil and Scott were sprawled out with their legs wide. Each man was on one of the twin’s beds. Phil’s son, Jack, was sucking on his daddy’s throbbing dick while Scott’s stiff cock was in Steffie’s warm mouth. Warm pre-cum from both men was leaking into the twin’s tight, nursing mouths. Jack was stroking his dad’s balls, even twisting them a bit to bring Phil a wave of pleasure-pain coursing to his brain. Steffie was fingering Phil’s asshole. She was doing what she called Swirlies, circular propeller motions in his butt. This she knew always drove Scott complete... Continue»
Posted by tankengine123 1 month ago  |  Categories: First Time, Shemales  |  
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SISSIFIED

art 1

It was quarter to 12. The door bell rang and she got up and went to the door. It was her friend Carmen.

Carmen was there to pick her up. They were going to a movie after lunch. She said." We can’t go yet. I have to feed my b*****r."

Carmen looked at her. "You’ve got to be k**ding me." She said.

"No." Stephanie said grinning. "It’s not quite what you think."

Stephanie looked at Carmen standing there. They had been friends for years. Carmen was black, tall, long black hair and a body that wouldn’t quit. She was ... Continue»
Posted by stig1963 6 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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My First threesome Part 2

After Ray's step-mother put make-up on me and fixed my already long hair she had me looking like a young sissy boy, that's saying a lot because I was 23 at the time. She then had me slip out of the outfit Ray had given and put me in a red throng and matching garter belt and bra. She had me wear black seamed stocking to make me look like a real slut. She then told me that she had to get ready for Ray's father Bob to get home and that I was to go down to Ray's room and sit with him until then.
When I got to Ray's room he was already dresses similar to me except his lingerie was white, and bo... Continue»
Posted by billieearls 5 years ago  |  Categories: Gay Male, Shemales, Taboo  |  
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Watching too much porn

It’s another night at home alone.  You get that aching again so you go to put on your favorite video.  You just love big asses and big titties.  The video starts and you see the gorgeous blond strutting in wearing her 5 inch heels, incredibly short skirt that is flashing her skinny red thong, a thin, white, button up shirt that she has forgotten to button all the way.  The few buttons that are buttoned are barely holding her large breast inside.  Her nipples already erect and showing through the pockets just screaming “lick me!”  As she passes the camera just can’t help but stare as her sweet ... Continue»
Posted by urgonnaputthatwhere 3 years ago  |  Categories: Interracial Sex, Masturbation, Shemales  |  
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One Weekend

One Weekend
I was twenty when I met Michelle. She and I didn't actually move in together, but she had a suitcase
that she kept over at my place with many different clothes in it. Everything from nice panties to no
frills granny panties. Her sexy black dress, jeans, bikini, lingerie, and regular stuff also like white tshirts
and pajamas. She had some cash through her f****y. She wasn't rich, richer than I was and still
am. So her clothes were mostly higher end stuff ordered or purchased from Europe. Also in the
suitcase were two dildos and three vibrators of different sizes along with som... Continue»
Posted by pr1456a 3 years ago  |  Categories: First Time, Shemales  |  
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Sissy Sarah’s Story


I couldn’t believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him.
It had all started two weeks earlier when I had changed my profile on one of the sites that I regularly use. Up until then, I had been ‘Mr versatile’ – willing to do anything anyone wanted – pretty bland actually.
Now what I had written was the following:
“Young 52 year old, looking for an older man, early to mid sixties, still sexually active willing to be my top. Would love to get together and decide what our roles would be and then keep them going wh... Continue»
Posted by cocksucker1966 2 years ago  |  Categories: Shemales  |  
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His teacher, The transsexual

A really nice story from another web page! Enjoy

Greg was late for class. He ran through the hallways. They were very particular about being punctual here. His health teacher especially. She was very focused on such things. Greg had been late twice this week. He couldn't help that his car kept breaking down. Ms. Sin was a real hardass and didn't accept excuses.

Greg had only started his last year of high school here after his eighteenth birthday a few months ago. He was worried about the impressions he was making. He got to the door of his health class and checked his watch apprehensive... Continue»
Posted by Ankakalle 4 years ago  |  Categories: Shemales  |  
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Slowing becoming a Cuck...what next?

I have not gotten rock hard in over a year and a half. It is a medical condition and it slowing getting better, but it is causing my wife and I to try new things.

We always had good sex, but because of her beliefs it was pretty straight forward. She did not enjoy me going down on her, because she had issue with me kissing and licking her where she pissed. She would give me a little head, normal foreplay (kissing, tit sucking, fingering) but within minutes we were in position to fuck! I could cum quick and go again...rock hard.

But that ended in January last year. I can orgasm now, b... Continue»
Posted by mattraulerson 1 year ago  |  Categories: Fetish, Mature, Shemales  |  
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Tranny Attack Ch. 02


"You'll be hearing from me again, sweety!" With those words Julia had kicked me out of her apartment.

I dragged by bruised and ass-fucked body home. Thankfully, Jane was not back as yet. All through the journey back to my house images of the previous night kept playing through my head. Discovering Julia's cock, of being tied up and buggered, of sucking her cock, and of having Julia piss on me. And it was all on camera! And who had she sent the videos to? If she blackmailed me, what would I do. I could pay her off quietly, since we were a traditional household and Jane never said anything ... Continue»
Posted by bi_hengst 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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my fantasy part I

I've always been interested in being a prostitute but never had the guts! This is what I would do if given the opportunity!!

It was another morning alone in my dump of a one bedroom apartment. Sexy shemale porn playing on my laptop and me performing my usual morning edging session!! I was strolling the web and came across some pictures of sexy crossdressers hooking on the streets! This made me want to cum so bad but I couldn't because I was edging and it felt to good when I stopped myself from cuming. I usually edge for an hour or two until I get so much precum my hand is sliding up and do... Continue»
Posted by nebraskasissypussy 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
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The Hotel Part 1

I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days.
Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, f***ed fem, huge dildos, and giant buttplugs are just a few of my fetishes, and I expected every fantasy to be fulfilled this week.
As I pulled up under the awning of the front enterance I was met by a woman in a French Maid uniform. I introduced myself, and said I was checking in fo rthe week. She smiled, as she opened my car door, helped me out of the car, took my ba... Continue»
Posted by NJStraponLover 4 years ago  |  Categories: Anal, Fetish, Shemales  |  
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me my daughter and a shemale

my last story was with my daughter for the first time now we both have shemale girlfreind very beautiful ones they would come over me and my daughter would put on our sexy heels she picks my shoes now lol and they would fuck us both on the same bed theses shemales are in good shape they would fuck me and my daughters tight lil asses and shoot globs of cum then they would watch us creampie it out one of them came over one night when i got off work my daughter wanted me to tougue out her shemales ass while she shoots in her pussy she has a big dick mine would never reach in that far i loved watc... Continue»
Posted by keiporn 4 years ago  |  Categories: Shemales, Taboo  |  
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SheMale Encounter -Hot Story -Please Comment

“Promise not to fall in love while you’re away?” Lana asked as she wrapped her arms around me.

“I’ve told you several times already,” I snapped at her. I had begun to get more than frustrated with her. “This is just a business trip and nothing more, besides I’ve never been the type to just fall in love,” I said.

She held on a little longer before she finally let me go. We kissed one last time and then I was off. As I walked down the runway I waved good-bye. She waved back animatedly. One look at her and I regretted letting her get on my nerves. Quickly I ran back into the waiting area ... Continue»
Posted by bmckzi 4 years ago  |  Categories: First Time, Shemales  |  
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How my chastity started

There was this woman where I worked at. She had a thing for retro and would wear business skirts, high heels and actual real stockings every now and then. She had a body to die for and legs that just simply made me melt. When she walked by I would simply melt. Could not explain it this power she had over me, it was more than just sex or lust, it was like the magnetic pull that keeps the Earth in orbit. I started small talk with her and over time we began chatting now and then. I WANTED TO HAVE SEX WITH HER SOOOOO BAD!!! But would not even flirt with her in that direction because I knew from of... Continue»
Posted by debbielynn 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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First time dressing up: Part 2

Dressing in my s****rs clothes became a regular thing after about 2 months of doing it, I would use her vibrator on my ass at least once a week. My f****y was gone more often so it gave me plenty of time to prefect doing my make up, hair and shaving my legs. One night when my f****y WAS home i was looking for a pen to write a card. I went too my parents room to look for one and on my step mom's dresser was a small blue key, i had no clue what it would go to and for some reason it seamed important. I put it back and continued on looking for a pen

Two days later my f****y was i out so imminen... Continue»
Posted by Badassgirl123 2 years ago  |  Categories: Masturbation, Shemales, Taboo  |  
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Exiting second time

After the first time had already passed, I decided to take some time as my ass still hurt a few days after my encounter. The guy I used to talk still had not sent me any message a 2 weeks after the events of the previous story so I decided to do something. After the pain went away I noticed I coul very easily play with my ass and I would not hurt at all! I went to the point that I could fist myself and it would rarely hurt.I played putting things in my ass and it felt awesome. I decided I was 100% bi and wanted to try something new, so I began crossdressing more seriously. I went to swimming l... Continue»
Posted by Ktm999 9 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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total sissy humiliation

my phone buzzed.

looking at the screen the name before me both puzzled and startled me.
I had posted an ad on craigslist 10 days ago, offering to suck cock. i was 32 and had been dressing as a girl and fantasizing about sucking cock since i was 13.....and now being single, I'd decided to act. within 12 hours of my ad going live I'd had 10 emails from guys...some of which i deemed timewasters. I'd quickly narrowed it down to a guy named Lee...at least thats what he said his name was.

Lee lived locally, and worked as a bar manager for a local pub. I knew the pub, it was a normal quiet pu... Continue»
Posted by hornyTVluvr 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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shemale sex slave

BDSM JOURNEY.

Let me first say i am no writer by any means.

This story starts 5 years ago. I was looking to move up in the mountains off grid with a homestead. I was a single man and wanted a parnter who could share with the daily chores and have for sexual gratification. Finding some one to leave everything the city offered to move to a rural area was a quest in itself. I knew I wanted a completely submissive woman ant my feet.
So I put a ad on craigslist and it went a lil something like this" tall single white dominate male iso single submissive woman to move to a homestead in a very ... Continue»
Posted by bigfranks36 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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