Shemales Porn Stories
Page 64

My New Lover!

I was still testing the waters a bit. I went out in my skinny jeans and just a t-shirt (I still don't crossdress in public at least not heavily, still uncomfortable), my slightly long hair makes me look very androgynous. I wear very subtle eye makeup as well, I am happy in my body, it suits being a guy for my job and a girl for my lover. I thought I liked him a little but by the time we made it back to my house, which was empty, an irregular occurrence, he had been very nice and hit on me a little. He complimented my body and my ass (not to stroke my ego but I love my ass, I get compliments on... Continue»
Posted by bisubtaylor92 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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We Met at the Gym

This is my first story. Feedback is appreciated.
When I woke up this Saturday morning I was hornier than usual, but I had to suppress my urges in order to make a 5:30am group fitness class. I put on my normal workout clothes, Gray/ White Stripe Shimera Boyshorts panties, Nike loose leg shorts, t-shirt, hoodie, socks and New Balance cross trainers. I like wearing the boy shorts for two reasons, one- they are very comfortable and two, sometimes I like to have my balls hang down on either side of the crotch. About 5:15am, I walked into the gym, swiped my membership card and walked past the r... Continue»
Posted by randy1stonez 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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Chance Meeting at the Gym

This is my first story. Feedback is appreciated.
When I woke up this Saturday morning I was hornier than usual, but I had to suppress my urges in order to make a 5:30am group fitness class. I put on my normal workout clothes, Gray/ White Stripe Shimera Boyshorts panties, Nike loose leg shorts, t-shirt, hoodie, socks and New Balance cross trainers. I like wearing the boy shorts for two reasons, one- they are very comfortable and two, sometimes I like to have my balls hang down on either side of the crotch. About 5:15am, I walked into the gym, swiped my membership card and walked past the rows ... Continue»
Posted by randy1stonez 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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Ashton & Terry

Mona Harris headed out of the door. She had both of her daughters in tow. It was going to be an all-day affair at the salon.

Terry heard his wife of three years start her white 2009 Nissan Altima. He waited for her to pull out of the driveway. He six-inch long, four-and-a-half-inch thick dick was rock hard. As usual Mona had given him no pussy. The six-foot-two, two-hundred-fifty-five-pound, dark-skinned, barrel-chested man got out of his bed. He marched down the hallway and into another bedroom.

Terry examined his cute, slim stepson asl**p. He walked over to the bed and ripped the black... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Shemales  |  
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NFL Season Opener

Marcus Phillips opened the door of his apartment. The six-feet-three-inch, two-hundred-fifty-pound dark-skinned man looked at the slim boi.

“Come inside,” Marcus ordered.
The twenty-six year old complied and said, “Yes, sir”

It was a Sunday – the second one of September. Marcus had asked the pussyboi to come over before the game. It was the season opener for the New York Giants. They were playing the Dallas Cowboys. The sissy boi switched inside. He was five-feet-six and weighed one-twenty-two. He had a caramel-mocha-latte complexion. The game started at 4:25 p.m. It was still early in ... Continue»
Posted by faggyboi 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Another College Experience

My Junior year of college was definitely the most sexually active time of my life thus far. Granted, I just started my Senior year, but thus far, I haven't kept the pace that I did last year.

I started crossdressing a few years back and do it in public every now and then as I look pretty feminine when I get dolled up. I have made it a habit that every Halloween, I would dress as something sexy and girly.

Last Halloween, I had a plethora of costumes that I wanted to wear, but ended up wearing a sexy sailor's costume. It consisted of a very short mini skirt, a very low cut top, and a litt... Continue»
Posted by wattheef 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Real Man Fucks Fags

“Where are you going,” asked Cynthia Ford.
Her husband of twenty years, Mike, yelled, “Out!”
“It’s 10:30. Why are you going out?”
“Cause I need to get some ass.”
“What,” she cried out.
“Yeah! You don’t be giving up the pussy and I got a hot li’l faggot that’s ready.”
“Fuck you,” she screamed.
“Whatever, bitch!”

The six-foot-two-inch, two-hundred-ten-pound, caramel-skinned dude walked out of the house.

His wife went to the fridge and extracted a bottle of gin. She opened it up and drank it straight. She was an alcoholic and had been since she first walked in on her husband fucking ... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Sam's Sissy Computer Tech

Since my first day at work as a computer specialist at C@T Construction I desperately wanted to have sex with Sam the owner. He was a stronger older man, divorced and in his early fifties. He started his company with a bulldozer and a dump truck and now it had 300 employees and over 100 pieces of equipment. Every day I worked around these beefy men and went home and masturbated furiously. Here I was a 110 pound, sissy, effeminate, gay twink surrounded by these manly specimens. I was dying to be fucked by one of them, hopefully Sam and hoped to be his “girl” one day. I just had to find the oppo... Continue»
Posted by captjim51 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Stepdaddy & Boi

‘Pomp & Circumstance’ began playing over the loudspeakers. The graduating class of Eleanor Roosevelt High School marched inside. The boys wore green robes while all of the girls were wearing white ones. In the stands, sat the f****y of Claro Booker. The s*******n year old’s mother, Belinda, was present with both of her s****rs. His stepdad rounded out the crew that came to cheer him on. He had been a star pupil. And finished in the top ten percent of his class.

When his f****y saw him enter, they clapped and yelled. The five-foot-eight-inch, two-hundred-pound, chubby medium-brown-skinned gr... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Shemales  |  
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Locke Up...New Arrivals

It was Tuesday – the day when new inmates arrived. Chris, a tall, white dude with a long, thick dick was the first off the bus. He was ready to get inside and sample the faggot punks this prison had to offer, the final person down the steps was Jericho.

Jericho was 18 years old. He was five-foot-seven and weighed one-hundred-forty-two-pounds. His crime of joyriding had cost him dearly. Veep heard about the young, soft bitch. He was promised to him now.

Veep was a medium-height, medium-build, Black man. He had gone five weeks without a pussyboi. He was ready to have his own slut.

Whe... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Locked Up Part 2

Keno Reese yawned as he woke up in the top bunk of his prison cell. His eight-inch yellow dick was rock hard. He nestled up close again to his cell mate, Winnie. He squeezed the chocolate bottom’s butt cheeks and placed his manhood at the sissy’s hole. He spat in his hand and rubbed the saliva along the length of his dick. Successfully lubed up, he began to slide his cock inside of the punk.

Winnie grimaced as he woke up.

“Owwww, Daddy,” Winnie screamed.
“Shut the fuck up, bitch,” Keno demanded delivering a blow to the side of his girly boi’s face.
“Yes sir,” whimpered the young fag c... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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DReft..

How I became a Bi GURL


So how did you become a bi gurl?

That's the question almost everyone I meet or chat with asks me... how did you become such a sexy transvestite, when did you figure it out, when did you learn you liked cock.

I actually love the question, because it turns me on to answer it.

When I was 15 or 16 I used to sneak into my parents room, find my dad's stash of Playboys and jack off to them. The girls were sooooo beauitful, I just couldn't believe it. I wanted to see and touch one, which led -- I guess this is common among us gurls -- to digging into my Mom's s... Continue»
Posted by Girliemagbator 1 year ago  |  Categories: First Time, Masturbation, Shemales  |  
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STEP INTO GURL: PART ONE; CHERRY POPPIN’ DAD

(not based on entirely true events)
TEE HEE!

My body was speaking to me for years, from puberty and possibly before that. I was different. I longed for feminine things and all that encompassed.
Including men.
I was finally old enough to drink and that helped lower my inhibitions.
I found a guy in his thirties online and he was not creepy or brash as the others.
He was a nice guy.
He was a nice guy that talked dirty, about things I had imagined for such a long time.
I was thinking of the touch of another cock against my own the first time I came.
I squirted my ow... Continue»
Posted by sweetsillyguy 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Comicon

Carmen Bullard sat down the last plate of scrambled eggs, thick-cut Applewood-smoked bacon, and toast with strawberry jam in front of her husband of nine years. He was seated at the breakfast table along with their two sons aged seven and five. The boys scarfed down their own meals while Larry munched away perusing the digital copy of USA Today on his tablet.

“Are you all packed for your flight,” the fourth grade teacher asked.
“Yep. I’ll head out shortly after y’all leave,” answered the average height, stocky dark-skinned man.
“Well, be safe and call me when you land. Have fun! Come on ... Continue»
Posted by faggyboi 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Theater gangbang of cockslut Kitty


I drove to the old-and-rotten-unofficially-turned-adult-theater that I had been too before, parked and headed in. I walked in, went to the counter to pay and the clerk gave me a once over.

"Ladies are free on Friday nights," he said.

Did I really pull off the appearance of a girl? "Oh, I'm not really a girl," I said, not wanting to cheat the establishment out of revenue.

"Hot stuff, you are close enough for my tastes," he said with a dashing smile. "Have fun up there." He then winked at me.

He was a cute boy, maybe mid-twenties, tattoos, and hoop piercings in his ears that stretc... Continue»
Posted by CumLovingKitty 2 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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Better than your wife!

I had to do some shopping one night, and I happened to be feeling particularly naughty. I put my hair in pigtails, put on my makeup, pink lipstick, black bra, white tank top, black thong, pink miniskirt, white stockings, and pink 6" heels. After grabbing my purse, keys, and phone, I headed out the door.

I arrived at the store and parked my car. As I went inside, I could feel guys checking me out. I picked up some vegetables, got some pasta, I was looking at the meat case, when I heard some hater say to the guy she was with, "I can't believe they allow sluts like that (she points to me) in h... Continue»
Posted by CumLovingKitty 2 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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My First Time With Old Man in Girls Undies

First, me say, this is a true story of how I lost my anal virginity but to protect my privacy and the people in the story, I will be changing people’s names.
This story is set when im s*******n and had just began experimenting with crossdressing and having gay thoughts. My favourite categories on this site are Bisexual, Anal, Shemale Fuck Guy, Guy Fucks Shemale and Latex. I was also broke as fuck and unemployed and summer was just around the corner so I needed money fast. It was around this time I remembered about the casual encounter section of Craigslist. I had been wanting to experiment w... Continue»
Posted by TeenTranny 2 years ago  |  Categories: Gay Male, Shemales, Taboo  |  
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Norman and Anastasia Part 2.

Luke and I follow Anastasia up the stairs. Her wrap round dress is tight across her big firm arse. Luke looks over his shoulder at me and grins. His eyes are level with that big swaying arse. She reaches the landing and opens the door to the bedroom. She hesitates a moment before walking in. She climbs onto the bed on all fours and Luke climbs up behind her. Her grabs the material of her dress and throws it over her back, exposing her arse God!! Where did Norman find her. On all fours behind her he buries his face into her crack and licks all the way up it. Reaching between her thighs he grabs... Continue»
Posted by dasilva1672 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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my first time ( translate from ilk seferim )

i think it's gonna better if i tell the story from the begining. When i was born my father was very happy to heard a has ason. İ guess lmost he doesnt know after happens. From the time after some situation happened about somethings wrong but my parents prefer didnt talk about that until i was twelve. the year at the begining of effective my hormones top so my body was begining the transform like a girl. espicially my breast my booty my emotional situation not different from my body. İ feels like so hot and get turn on when i see naked man body at magazine or beach finally my parents made a dec... Continue»
Posted by arzulumelek 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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Norman and Anastasia

For the first time in my life, my uncle Norman was not pleased to see me. His s****r, my mother, had not heard from him in a little while and was worried so I had been volunteered to drop in on him and make sure that all was well. So here I am stood on his doorstep and he is peering round the door at me, holding the door open as far as he can to make sure that I can't see in but so that he can see me. He wears an annoyed look on his face. I am disturbing him in some way. It is then that all becomes clear. A voice speaks behind him.
"Who is that Norm?"
He turns his head so that he is speakin... Continue»
Posted by dasilva1672 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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