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Shemales Porn Stories

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First TimeGay MaleShemales

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… Read more

Posted by faggyboi 2 years ago 2 1,981 100%

Theater gangbang of cockslut Kitty

Gay MaleHardcoreShemales

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… Read more

Posted by CumLovingKitty 2 years ago 7 3,302 90%

Better than your wife!

Gay MaleHardcoreShemales

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… Read more

Posted by CumLovingKitty 2 years ago 7 3,915 90%

My First Time With Old Man in Girls Undies

Gay MaleShemalesTaboo

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… Read more

Posted by TeenTranny 2 years ago 10 7,106 96%

Norman and Anastasia Part 2.

AnalGay MaleShemales

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… Read more

Posted by dasilva1672 2 years ago 2 883 100%

my first time ( translate from ilk seferim )

AnalFirst TimeShemales

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… Read more

Posted by arzulumelek 2 years ago 2 3,161 17%

Norman and Anastasia

First TimeGay MaleShemales

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… Read more

Posted by dasilva1672 2 years ago 8 5,555 90%

The Open Door.

FetishGroup SexShemales

There is nothing so erotic, as the opening of two legs, no matter what they reveal, to get the juices flowing and create that volcanic feeling, that an eruption is due to be created. So much of foreplay is eroticism, expectation, fantasy becoming reality and the anticipation of excitement, that will be better than it has ever been before. Just simply the brushing of two hands, lingering to squeeze for just a second, a twinge that says - I'm here. The hello kiss on the cheek that takes a second to become a brush of the lips on the long slender neck, which bristles… Read more

Posted by totallyurs 2 years ago 2,249 83%

HOW I BECAME a hollywood HOMO AND ADDICTED TO BEIN

Gay MaleInterracial SexShemales

PART 2, ok so I'm still extremely high and I'm on the corner of samo blvd and st andrews and we are now attracting multiple cars driving past and staring and i have no idea what I'm doing i was just so nervous being dressed like a CHEAP WHITE SISSY AND my top ts momma has basically made me understand that we are gonna stay here with about 6-7 other tgirls that are older and all are mexican and black,, they were yelling at me and saying that because I'm young and white I'm basically gonna be picked up any second,, i ws nervous to leave my top ts mommy erika and she promised that she… Read more

Posted by LosAngelesSissy33 2 years ago 5 2,948 80%

Part Two: The Carpet Guys Koni Gets Ruined

AnalGroup SexShemales

Richard said something to Juan and they both laughed as I laid there in puddles of my own goo... my face covered in cum and stoned out of my sissy mind, I knew I couldn't get up. Richard pulled his pants up, leaned down and with his heavy accent, said, "chica our boss, Mike, will be here soon to check on our job... You'll need to tell him those big wet spots are from you okay? It's not our fault... " he stopped and snickered, "that you can't control yourself ya little slut." Both men laughed and went back to work. I couldn't get up. My body felt so heavy and sl**py. I didn't care who walked i… Read more

Posted by Konicum 2 years ago 8 1,829 100%

The College Fantasy Part 4

FetishHardcoreShemales

I walked towards the bathroom where she had gone before me. I was in a daze. The reality of what had been happening was sinking in and my body would not stop the incessant tingling. It felt like my skin was heating the room. A cold shower sounded magnificent. The water was already running. I could hear it from the hallway. When I turned the corner into the bathroom she stood before me. Her whole body was exposed and for the first time I was able to observe all that had changed. Her tits had grown from the C cups they once were to D cups. Her feminine figure was as beautiful as ever… Read more

Posted by fictiong 2 years ago 4 2,369 100%

divorced

FetishGay MaleShemales

After I was divorced from a 20 year marriage with bland sex I met Marcella. She tuned into my unfulfilled fantasizes and told me about her wild sex life. After she introduced me to my first three some with a black boyfriend I was hooked and we got married. After that, my life was full of depraved raunchy sex and even cross-dressing. (MF, MM, 1st-bi, oral, anal, swingers, alcohol, cd, orgy, voy) *** Marcella and I were a perfect match. I was in my 40s and just out of a 20 year marriage with all sorts of sexual fantasies She was divorced, in her 30s and scaring guys off… Read more

Posted by pcarter 2 years ago 3 4,697 100%

Bernadette's Initiation

BDSMFetishShemales

Bernadette's Initiation A shy, innocent t-girl dreams of domination by a man. She is persuaded into a day's adventure in this role and gets very much more than she bargained for, but gradually comes to understand her own desires. Contains scenes of bondage, non-consensual hardcore gay sex and breath control: if this will upset you, please look elsewhere. I must have hesitated for a moment for a sharp jolt of electricity on my nipples left me in no doubt that my immediate compliance was required. So, heart in mouth, I obeyed the male voice in my earpiece and started to… Read more

Posted by klammer 2 years ago 1 2,629 80%

First time hooking up with a shemale

FetishFirst TimeShemales

Well the first time I hooked up with a shemale was an e****t visit (night out, massage and the rest :)), this was when I just started to gain interest in shemales (about 2 years ago), so I became curious and wanted to know what it was like to spend a night with one, after all they say its having the best of both worlds. I looked up a Brazilian shemale online and when I saw the pictures, I couldn't resist a visit. I mean her femininity was beyond this world, stunning from head to toe. I gave the e****t a call and asked to see if she was available for night out and it must have been my lucky day… Read more

Posted by mensah9 2 years ago 7 4,065 92%

HOW I BECAME a hollywood HOMO AND ADDICTED TO BEIN

HardcoreShemalesTaboo

PART 1 I was 18 high and d***k when i stumbled onto a tranny hooker neighborhood and i stupidly picked up a sexy girl not realizing she had a huge 9in uncut cock and was almost twice my age!! I'm 18 thin great body lots of girlfriends and this night changed it all!!!!! i went back to her place and we got naked and started smoking and parting and listning to house music and thats when i realized that i wasn't the top in this situation!!i was gonna bottom !!!! she dressed me up and shaved my ass and legs and head, put a wig and fishnets and a skirt that was really 2 short and black t… Read more

Posted by LosAngelesSissy33 2 years ago 11 6,831 100%

First Time With A Guy And First Time As A Gurl

First TimeShemales

worked summers in a factory by my house when I was in college. Nice, clean summer job. Charlie, the Chief Engineer was my boss. He played Div. 2 college football and still was in great shape. Thick arms and legs, big hands, broad shoulders. He was going a little bald, but otherwise...anyway. I wasn't into guys, so I didn't notice those little 'things'...signals, whatever. I had a somewhat steady girlfriend, but she went abroad that summer. Being 19 I was, it seemed, always thinking about sex. Loved jacking off to the 'Men's Magazine; I found in the guys locker room. I especially found the Fre… Read more

Posted by keripinkpanty 2 years ago 21 6,125 100%

Tranny orgy

Group SexInterracial SexShemales

You can live with someone and never really know them. I was running a car wash in West Palm beach and every day I would take lunch at a cafe down the Blvd. The food was good, and cheap and I had the hots for Debbie, this built to the hilt redhead chick working there. She wasn't any great beauty but she had a body to die for. 36 DD tits. big hips and thick legs. Just my type. After a couple weeks I got the nerve to invite her to TGI Fridays for some drinks. After a few, she started talking about her past. She was on parole from Ohio for cocaine trafficking. I found that interesting because a… Read more

Posted by kwhagie 2 years ago 3 5,087 95%

My t-girl experience

Shemales

so I FINALLY got with this t-girl named Chrissy, turns out my gay friend from school Martin calls me up, he's like, ya wanna go to this special club with me? oh yah! :) so I meet him there & he's def'ly dressed as queer bate! lol I wore a skirt & a cute sleeveless top cause it's still hot as f*ck here even in october, Martin's in white shorts & a pink golf shirt. he flashes me his undies outside the club, he's wearin like, the tiniest thong - ever! plus he's already hard. so I'm like, you want some relief on that before we go in? he goes, hell no, I'm not shootin my wad unless I'm sitting… Read more

Posted by surfsup18 2 years ago 10 3,188 50%

A Wife's Revenge

Shemales

"What the hell is this!" Michael Landers turned slowly toward his wife. She had been changing the sheets on their bed when she came across an unexpected surprise. When the couple finally stood face to face, Michael noticed his wife of three years staring back, her left arm pointing straight at him with a purple bra dangling off her index finger. "Well, um, it looks like a bra," Michael answered. "Ya think? Gee Michael, I never would have guessed if it hadn't been for you. What I really want to know is who it belongs to and what it was doing underneath your pillow." "Wha… Read more

Posted by lana100 2 years ago 4 5,859 20%

The College Fantasy Part 3 (Futanari)

FetishHardcoreShemales

I was on my back in the bed. My head was at the edge and she stood over me stroking her massive fleshy cock. I was transfixed by her luscious tits and the warm tingling was intensifying. Her words, "open up my little cum slut," echoed through my mind and I could only resist a moment. She slapped my face and as I opened my mouth in pain she filled it with her massive futa dick. "Thats a good cum slut, take your time and enjoy my cock." She spoke slowly as I imagined the smile on her face. I could see nothing except the space between her legs. He cock was long and fat at best I could ge… Read more

Posted by fictiong 2 years ago 2 1,462 100%