Shemales Porn Stories
Page 73

The Making of a Gloryhole Gurl Part 3

Making of a Gloryhole Gurl! Part 3
By Kristy

I look back on some of the Pictures from my early days, going to the Adult Bookstores and the Park and can’t believe how bad badly I was at putting my makeup on and some of the things I wore. Although I still like to dress slutty!
I could sneak away for only so long before I had to change back and make it home without a trace. I made a major breakthrough soon and began going into the bookstores completely dressed and I was going more and more to the ABS’s and sucking as many cocks as their were, and if I got real lucky I would fi... Continue»
Posted by kristygurl 5 years ago  |  Categories: Shemales  |  
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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 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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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 2 years ago  |  Categories: Mature, Shemales, Taboo  |  
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"Just Treat Me Like A Lady" My First TS

I had just moved to San Antonio for a new job. I only knew a few people from work and asked them where I should go for some night life. They told me to go downtown and gave me the names of a few bars. I was 27 at the time, athletic, a little over 6'0" and about 175." I have a good body and dress casually. I went to the first bar on the list they had told me to check out. I walked in wearing faded bluejeans and a tight gray t-shirt. The bar was about half full of men and women and everyone seemed laid back and cool. I sat in the corner booth and ordered a beer. A few drinks in I noticed a stunn... Continue»
Posted by JesseM75 1 year ago  |  Categories: First Time, 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 1 month ago  |  Categories: Anal, Group Sex, 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 5 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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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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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 4 years ago  |  Categories: Gay Male, Shemales, Taboo  |  
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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 1 year ago  |  Categories: 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 2 years ago  |  Categories: First Time, Shemales  |  
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Crossdressing I Got Fist Fucked

I was feeling horny so I put on my blue satin dress with white polka dots, satin panties, my white satin gloves, garter belt & flesh colored stockings. Then I put on some deep red lipstick and lip gloss and topped it off with my blonde wig.

When I looked in the mirror and saw the sweet hot girl looking back at me I knew I'd find a guy who wanted to fuck me tonight.



I posted a picture of myself on Craiglist and within minutes I had half a dozen guys messaging me so I invited them all over.

The first guy who came to... Continue»
Posted by Doyoudeep 14 days 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 7 months ago  |  Categories: Fetish, Mature, Shemales  |  
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Taken to be a Shemale Lover

I had went to work at the burger joint, when the manager informed me that 'I have too many people on payroll today, I need you to clock out and leave.' This is what happens when you work for a fast food joint, all the k**s that go to school and can get a permit flock to the fast food places. At least you get some training in how to be on time and understand job responsibility.

As I was working towards the park a coral blue car passed by, it pulled into the lot across the street and came speeding back. The driver was a familiar face, Joliet, one of the she-males that enjoyed my restraine... Continue»
Posted by d4david 4 years ago  |  Categories: Anal, 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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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 3 years ago  |  Categories: First Time, 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 1 year ago  |  Categories: Masturbation, Shemales, Taboo  |  
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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 11 months ago  |  Categories: BDSM, Fetish, 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 1 year 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 10 months ago  |  Categories: First Time, Shemales, Taboo  |  
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My Sexual Resume

About Me

I am a very sexual crossdresser who enjoys all sorts of activities. I have a small cock which I milk on a daily basis. I love to be photographed when I am with someone. You might say that I am a exhibitionist, when I am dressed like a slut.

Sexually

I am bi sexual and love women as much as I do men. I am very oral, anal, and a kinky submissive. I like to be used by men and women when I am dressed. Those that have been with me usually leave satisfied, which for me would be a face full of cum. I love those hollywood pop shots all over my face. I love kissing and fingering of m... Continue»
Posted by slut2eatcum 4 years ago  |  Categories: Shemales, Taboo  |  
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