Shemales Porn Stories
Page 12

My First Time as Sara... Pt. 02

sissy boi – crossdresser – tranny – lingerie – virgin

I look up at Steve and give him a genuine smile. A smile that tells him I want and crave him. In a whirlwind day that started with me buying some girly stuff to enjoy on my day off from work, is now ending with another mans cock in my lipstick covered mouth.

I have his legs open and I'm on my knees. My hands are now running over his muscular and tight legs and my tongue licks his stomach. I have a naked man, average in every single way, except for his very thick, 8 inch cock sitting on my couch and I'm in my black stockings wit... Continue»
Posted by naughty_bi_interest 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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My first cd sexual experience w my virgin roommate

My dorm room was wrecked trashed with take out containers and empty beer cans. I would ask my roommate Matt to help clean the place but he was always face deep in his hdtv playing video games. Maybe if he got laid atleast once in his life he would put the controller down. He never tried talking to any girls because he was always afraid they would turn him down because of his weight. And as much as I really needed the place cleaned I wasn't going to clean a dish but had a better idea. A few weeks ago I went into my room after class and created a cliche sexy girl name online account in hopes to ... Continue»
Posted by triplexvenom 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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The civillian

I shadow wrote this story for a friend. The two of us hope you enjoy it.

When I finished high school I spent a few months working, before being drafted. Aside from a short period of training, during the first half of my term I spent most of my time behind a desk. I did spend a day a week doing guard or drill duty, to keep in shape and keep my field skills fresh. When things escalated and another unit was in need of a new sergeant, I was promoted and got reassigned. Still behind a desk, but now assigned to a war zone, I did spend a lot more time in the field. I had to go often to an improvi... Continue»
Posted by GalFa 3 months ago  |  Categories: Anal, First Time, Shemales  |  
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My First Time as Sara... Pt. 01

crossdresser – sissy – virgin – sissy boi – anal – lingerie

I only knew Steve as my landlord. To be exact, Steve was the only son of the two people that owned the small apartment complex I am currently living in as of right now.

My reason for moving here was out of necessity than anything else. Three months prior to moving in the 20 unit complex I lived on the other side of town with my then fiancé Sara. We're both late 20 something k**s that moved in together after collage and while the first couple of years seemed grand, it was bad things that were under brewing in the relation... Continue»
Posted by naughty_bi_interest 3 months ago  |  Categories: Anal, First Time, Shemales  |  
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Tits Have Benefits Ch. 03

Shemale - crossdressing – feminization - transfirmation - anal – strapon – oral

Thank you for everybody's support for this story. In this chapter the complex dynamics of a polyamorous relationship including 4 women and a shemale is explored. Andrea becomes gradually and lovingly integrated into this 'f****y' while having the time of her life ...........

After transforming myself into a shemale and returning to claim the love of my life Jane, I was accepted into Jane's loving f****y of lesbian lovers, this despite the initial protestations of Jenny a tall blond bombshell. In fact J... Continue»
Posted by naughty_bi_interest 4 months ago  |  Categories: Anal, Fetish, Shemales  |  
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Brad's Bitch

bisexual – gay – reluctant – domination – feminization

The phone rang. I pulled it from my jeans pocket and saw that it was Brad. Shit! I really didn't want a call from him right now. Maybe I should just ignore it. But somehow he always knew when I'd just ignored his calls. And then that was even worse.

I answered it, thinking only fleetingly about "the speech" that I'd composed and honed over the years and knew now that I would never actually give. I don't know why I even thought of it anymore. Maybe it made me feel just a little bit in charge of my life to at least imagine that ... Continue»
Posted by naughty_bi_interest 4 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Playing with myself dressed.

I lived by myself for a while so no problem there, so after showering and shaving my balls and butthole, I set up my dvd player, (yeah it was a while ago), to play Ladyboys in Latex. I retreated to my bedroom to choose an outfit.
Hmmm, I feel naughty and nice tonight, so white, definitely white. I chose a white silky bustier with spaghetti straps and garters, and some brand new thigh high sheer white stockings. After I attached the garters, I pulled the laces on the back as hard as I could and tied them tight. I tucked the laces up so they wouldn't get messed up in my ass.
I looked in the m... Continue»
Posted by badboy4320 4 months ago  |  Categories: Anal, Masturbation, Shemales  |  
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Cockatoo part 10

Cockatoo Part 10

Nikkie Silk

My heart skipped a beat as I heard Shane’s voice from behind me and felt his hand on my shoulder. It couldn't be, I thought, I must be so tired I was hallucinating. Alex said, ‘Hi Shane, glad you could join us.’ Nin looked as if she had seen a ghost, Areeya was smiling in welcome and I felt like I would pass out. The hand moved off my shoulder and Shane’s massive frame came into sight.
‘Hi Nin, Hi Areeya.’ he said, then paused and looked at me, ‘Hi Jamie, how are you? You look gorgeous babe.’
I looked at Shane and then Alex and back at Shane. It was clear ... Continue»
Posted by nikkiesilk 4 months ago  |  Categories: Gay Male, Shemales  |  

Tits Have Benefits Ch. 02

crossdressing – shemale – strapon – anal – feminization – oral – transgender

Well thanks for the positive feedback from my first story guys. I am touched that you picked up on the fact that this is actually a sensitive love story. In this next part Andrea finds that in choosing to be in a relationship with Jane she also is choosing to be in a relationship with Jane's lesbian friends.........

In summary may name used to be Andy, now it is Andrea. And after completely transforming myself into a woman, tits and all and with the only exception being my dick, I had returned to claim ... Continue»
Posted by naughty_bi_interest 4 months ago  |  Categories: Anal, Fetish, Shemales  |  
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Never Going Back Again

feminize – feminization – transsexual – crossdresser – gay

To tell the truth, I never really figured out how to do the guy thing very well. I was always small for my age. People used to say that I'd shoot up someday, but it never happened. All through my school years, I looked about two years younger than my classmates. It didn't make for an adolescence filled with confidence, or even security. I was picked on mercilessly—teased, of course, but also actually beaten up from time to time.

It didn't help that I wasn't just small of stature but also small in the "manhood department"—s... Continue»
Posted by naughty_bi_interest 4 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Successfully squirting like a sissy

After getting home from a long day of work i realized i would be alone for a few hours. I haven't came in a week. An all time record for me! Then i thought about using my toys on my sissy hole. My cock stands up throbbing with agreement. I thought about trying to make my cock squirt just by use of toys sad that i don't have the real thing.

I showered, cleaned out with a douche and stripped naked i sat down in front of my computer my cock rock hard.

Looking on xhamster i found a few sissy trainer compilations and bare-backing vids. The thought of a hard thick cock cumming inside me set me... Continue»
Posted by sub_guy_Sissy 4 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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1st time-GAY BATH TS's and Black men

I was in Columbus on business a few years ago and happened to see an ad for a place called CLUB BATHE at a gay bar I was in. It was near closing time at the bar which was loaded with Transsexuals (mostly black) due to a drag show they were having. By the end of the night I was so horny I was dying to suck some black cock as I am hopelessly addicted to the wonderful taste of them that I decided to go to the bathhouse on the ad.

I drove the few blocks to the bath and went in. The guy at the front desk told me how much for a "membership" which gave me access for as long as I wanted to stay as... Continue»
Posted by reesielover 4 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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The Odd Meeting Part 2

Ross stands and takes me in his arms. He kisses me again, pushing his cummy tongue deep into my mouth and letting me taste my own cum. When he breaks away, he asks me if I would like a hot drink! The question seems so incongruous but I say coffee, please. He makes the coffee and I watch him and then we sit side by side at the little table! He has put out some biscuits as well. 'To keep your strength up' He grins! We sit and chat about all sorts of things and his hand rests on my stockinged thigh and he slowly rubs it. When his hand starts to creep up towards my panties I know that I should be ... Continue»
Posted by dasilva1672 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Kitty's cab ride!

I was coming back from a trip and I took a taxi from station to my home. The train was 5 hr late and what was supposed to be a 7 pm arrival was a late arrival at 1 am midnight. I got in the taxi as I noticed the city slowly going to sl**p with roads getting clearer and quieter every minute. I was in the taxi with a man; he was a nice man, maybe thirty years old by looking at him. We made small talk, he moved here with his f****y when he was three years old, he was single, and did not say much. He kept on looking at me and smiling in the rear view mirror, but what could I say? I'm an attractive... Continue»
Posted by CumLovingKitty 4 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Married Black Man's Ladyboi

Torrance Denkins was completely infatuated with transsexuals. He watched shemale porn constantly. He was married to his second wife. In total, he had five c***dren - three by his first wife and two by the current one. Torrance was forty-eight years-old. His betrothed was only 29. The homicide detective walked out of the precinct and got into his personal vehicle. He drove a black 2014 Cadillac CTS.

Once he got settled in the car, Torrance started it up and then sent a text message to Mitzie.

Mitzie Lim was elated to get the notification alert. She had not seen Torrance in two weeks. She... Continue»
Posted by faggyboi 4 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Sissy Toes

Little Sissy Tippytoes

"Queen Mary, she's my friend;
Yes, I believe I'll go see her again."
Bob Dylan
"Just Like A Woman"

As is true of young soldiers everywhere, I hung out with a bunch of
guys from my platoon, since those were the people I spent most of my time
with, and felt closest to, aside from my folks back home. It seemed
that the goal in life of all the guys in my barracks - again, like
most soldiers everywhere - was to earn weekend passes, so we could
go off-base and l... Continue»
Posted by klammer 4 months ago  |  Categories: Fetish, Gay Male, Shemales  |  


It was very lonely in my room, but it had been lonely in all
of the rooms I had lived in. My Mother and Father had been killed
in a car, bus accident during my first semester at college, Since
I had no other relatives and no money of my own I had sold their
house and with the life insurance money and the settlement from
the bus company, I was relatively well off. I had decided to
continue at college and was able to live well and pay all of my
tuition. But now having graduated with a major in photographic
journalism, and minors in business and computer science, I had
barely over $ ... Continue»
Posted by klammer 4 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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My First Threesome

My First Threesome

This is a story which happened to me a few years ago. I was living in London at the time.

I woke one Saturday morning and went through my usual routine - nice bath shave etc. Once I had done my makeup and got dressed (nice lingerie, natural coloured tights, denim skirt and a t-shirt), I sat at the computer to do some work which I had to finish – once the work was done, I had a little surf through the internet and suddenly became really horny. That was it I had to get some cock in me, I went through all the usual sites to get some action – but it wasn’t happening. So I ... Continue»
Posted by imogencole 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Dogging Orgy!

This is a little story about my antics when I go Dogging (which I do not do that often, but when I do – I love it).

My first experience of dogging (or cruising as it was then) was back in 1996. After having done all of the usual nonsense, in the bathroom. I picked up my bag of tranny bits, jumped in the car and made my way to a secluded spot to get changed and do my makeup.

Needless to say, I ended up looking like a whore – little black mini dress, black/red matching lingerie, black seamed stockings and black patent heels, with makeup to suit. It wasn’t the intention, but I had limited ... Continue»
Posted by imogencole 4 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Office Party

The office party was great. Since moving into the new space, TechTronix had not thrown a happy hour. The office manager had sprung for an open bar. The company had just over 300 employees and about half of them worked from this particular location.

One of the support team members, Vic, had several screwdrivers. He was not the only person to drink a bit too much. He was about six-two and weighed around two-hundred-forty pounds. His beer gut was slight and he had nicely defined arms and pectoral muscles. His head was shaved and he wore glasses. The caramel-skinned brotha had no problem getti... Continue»
Posted by faggyboi 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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