Shemales Porn Stories
Page 12

Stefan's Blackmail

When I was about 19 I started to crossdress. I didn't have gay feelings or strongly identify as feminine but I felt strangely attracted to my older s****r's clothing. One day I tried on a skirt and I found this simple act feel so thrilling that at the next opportunity I tried on a two more things...a dress and and a pair of her jeans. I was always thin, especially when I was younger, and my s****r was only three yeas older than me, so I had little problem fitting in most her stuff. Actually the stuff at the back of her wardrobe, the stuff a year or two old that she didn't really wear anymore w... Continue»
Posted by tricked-sissy 3 months ago  |  Categories: First Time, Shemales  |  
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Being a good slutty Sissy

Being a good Sissy for my mistress

“Hey Martina. do you like what you see?” Samantha, a very beautiful shemale with tits size D, asks standing in front of me. A smile curls her lips as she strokes her 8 inch cock.

“Yeah, I'd love to play with a cock that big.” Martina says licking his lips at the sight of pre-cum dripping from the tip of her cock. I’m a 5 feet 11 tall sissy original called Mark. If I have to dress for my shemale mistress as a sissy gurl I call myself Martina.

“Well then, come and get it. on one condition. You're my pet until I'm satisfied.” Samantha says with a smile... Continue»
Posted by Arnie65 3 months ago  |  Categories: BDSM, Shemales  |  
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Sexual Fantasies 001

One of my sexual fantasies is what I call "f***ed anal orgasms" or "anal ****"

Everything starts with a date with a shemale scort. I arrive to her flat and a 185 tall woman, dark skinned and with a femenine figure, opens the door. She invites me to get inside with a toothpaste advertisement like smile and a long curly hair. She takes my hand and gides me to a room with a king size bed with black sheets.

She sits me in the bed and starts asking me
-What would you like to do, honey? Do you want me to start blowing you and then you fuck me in all fours? Or would you like a girlfriend expe... Continue»
Posted by Auspex 3 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Becoming Madison_CDs Daddy Chapter 2

"Madison I know you enjoyed that didnt you, you little faggot" I said as I reached the bedroom door.
" Yyyess daddy " he whimpered
" Tomorrow I want you completely shaven use your mothers hair remover and shave your cock dont let me down , understand ."
I shut the door and went to bed .
In the morning I went downstairs for coffee and waited.
I finished my cup showered then knocked on Madisions door and opened it.
He was there in his bed with his covers over his head.
I walked to the bed and pulled back the sheets.
There he was naked and smooth from the neck down his shaved cock laid ... Continue»
Posted by rabbit007 3 months ago  |  Categories: Anal, Shemales, Taboo  |  
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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 3 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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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 3 months 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 3 months 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 3 months 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 3 months 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 3 months 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 3 months 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 3 months 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 3 months 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 3 months 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 3 months 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 3 months 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 3 months 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 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Confessions of a cross dressing slut....1st BBC

So about 6 months after my first taste of cock, i began talking with another man on xhamster. He was dark, handsome and middle-aged.

He told me how much i turned him on with my pictures and how much he'd love to meet. The problem was, he was married and worked as a professional and couldn't be seen for the sake of his marriage and career. No problem. I told him we could be very discreet and no one would find out.

We agreed to meet in Manchester. He booked a hotel near the centre. I thought one outside the city would be better and more discreet but he said this one would be fine.
It wa... Continue»
Posted by mileslong34 3 months ago  |  Categories: Anal, Interracial Sex, 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 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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