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My Shemale experiences
I have had experiences with Shemales. All in Hawaii. Three different ones. I met them all through yahoo chat when it was still fairly popular. In the 1998-2000 time frame. The first one I met up with was doing video shows in some back area part of Honolulu. She agreed to meet me as long as we only h... Read full Story
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My First Filling
It was my 18th birthday and my friends were getting on my back about still being a virgin. They’d pick on me about having not had sex with a gir yet, but they didn’t know that I fantasied about something other than a girl, I lusted and craved myself a trans partner. All the fun of a girl but with a ... Read full Story
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When I Knew I Was A Crossdressing Sissy Slut
I remember the fun I had taking selfies with sexy little outfits and make up on. I loved the dirty,sexy feeling of taking pics of me exposing my asshole and sliding back onto a suction cup dildo stuck to the wall. Hearing from a guy just how much he wanted to eat my ass or fuck me always got me ting... Read full Story
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yes, Mother give it to me
"Do your fucking job right, Henry! Jesus Christ, what are you, five years old? If I ever have to call you in here again, you're done! You hear me? You'll never work in this business again! Now get the hell out of my office." Mona could feel every set of eyes on the floor anxiously awaiting the pi... Read full Story
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Taking Ricky's Cherry
My work has me traveling all over the US and if you have read any of my previous stuff then you might have figured out that I have a major cougar streak. I just love being the first T gurl to a sexually inexperienced young guy. I was bored and horny in the hotel room, so I logged into a gay dating s... Read full Story
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The trip
I was at work and they decided that some of us had to go to Florida to work on some problems so I was picked. I went home and packed and made sure to pack some of my sissy outfits also because I would be in a hotel for 7 days and have the room to myself it was perfect. The next morning me and the ot... Read full Story
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The four of us
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
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My first time having sex with a Tranny
I have been obsessed with Trannies for as long as I can remember. There is something about a gorgeous feminine woman with a big thick cock that drives me crazy! I turns me on so much that I kept pushing myself further with my love for Trans women. I bought sexy dresses, underwear and heels to wear s... Read full Story
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Gangbanged By 3 trannys
Gangbanged By 3 trannys This is a story about the night I was Gangbanged by 3 trannys. I was at a Transgender after hours clubs that was filled with hot ass Tgirls. This tall white gorgeous woman was eyeing me the moment I walked in. She was wearing this fitting blue dress that showed off ... Read full Story
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My Shemale Stepmother Part 2
"Not yet, bitch. You've got to beg for it first," she slapped my face with her semi hard cock, "Now, tell me what you want." "I want your cock, mistress," I said wimpily. "What do you want to do with it, slave," she slapped her cock across my cheek again... Read full Story
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Hot Part 3
It's hard to explain, but sucking his dick that night ignited something within me. There was clearly a sense of control over him, but the feel of his warm meaty flesh sliding across my lips and filling my mouth was intoxicating. It's as if I'm addicted to it now. The truth is that I have never wa... Read full Story
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Next Phase - sequel to Continuing to love the feeling
Now I would like to have both of you engage in some light bondage, how do you feel about that? Maggie quickly replied, I'm up for anything and since Sheri's my Bitch she'll do as I say. Ok then, let's get started, Linda , please come over here and let me strap you into my special sex lounge.... Read full Story
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A Night Out To Remember
A night out with Liz and Sue I had known Sue for almost five years but had known Liz for a lot longer. We had met while she was still at school although I was four years older we still became good friends. After she left school I helped her with her college work and more importantly when she need... Read full Story
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Big Daddy
BASED ON ACTUAL EVENTS As is the case with most hard drug users, you start off small and end up making your way up. Since I was 15 I had been smoking weed. One of my friends had introduced me to some other drugs like meth or coke a few years later. The weed was still a big influence but it all se... Read full Story
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Click, click, click....
Click, click, click…the sound of high heels contacting a hard surface has always attracted and aroused me. Whether it’s on tile floors in a hallway, the concrete of a parking ramp or the asphalt of a mall lot, I turn in anticipation to drink in some pleasing eye candy. How short will th... Read full Story
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Birthday Party
It was now about 11 pm and Sue and I have been at it for the past 3 hours. Sue had me get up and go into the bathroom. As I stood in the shower I thought of what we did. Sue knew how to pull the right strings on me or in me. And she knew what pleased me. I washed all over. I had no idea of what was ... Read full Story
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David Invites JoJo Over
Although I fucked Del that night, for the first time in our marriage I was thinking of someone else. I just couldn't erase the image of our sexy neighbor lying bound and helpless on our bed wearing the very same peignoir set that Del wore when I took her virginity on our wedding night. As I lie awak... Read full Story
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Dawn's Diary Chapter 2
The month before I was due to go back to San Francisco on business went slowly as I thought about the incredible fucking that Sam had given me and the prospects of another, even more adventuresome trip. I hoped that the next trip would again find me with Sam's dildo up my ass. The anticipation kept ... Read full Story
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50 Shades of A Bookseller
So, I finally got a "proper" job and managed to move out of my parent's house. It was a damn good job too, as my crossdressing was becoming increasingly difficult to keep secret. Numerous times my Mum would try to talk to me through my bedroom door, whilst also slowly creeping it open to ... Read full Story
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I Told You
“No, please…” I barely audibly whispered. “Shut up you little cum whore!” “So... ohh god, no... Fuuuuuuuck,” the words leaked through my painted lips. “You want that hole filled too, you little cocksucking bitch?” “No, please! ... Read full Story
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Trisha
The doorbell dinged. It was my next door neighbor Pete. I had known him since I moved into these condos two years ago. We met at one of the monthly parties our association throws. That one happened to be a barbeque and I remember the dish he brought to the potluck was amazing. Pete was always trying... Read full Story
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My first shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe t... Read full Story
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SHEMALE SEX IS THE BEST
I had been in sex with gays for 1 year, but had always been intrigued by those hot looking chicks who packed more than a pussy between their legs. I had no idea where to find one in Kanpur I was definitely bi-sexual, still seeing whores, and still going to gloryholes for my cocksucking needs. I w... Read full Story
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Shool teen crossdresser first time sex
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest f... Read full Story
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Francine Hung Shemale
This is the story of "Francine" a Transgender woman from California. She and Jonathan meet in a Tucson resort two weeks after their first weekend together. Note from Francine-Thank you Mrstanley for writing and submitting my story. In real life I live and work in California and Mexico as ... Read full Story
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My Dream pt 3
Our first invitation arrived at the end of September. Sydney spotted it first and tossed it into the trash with out looking at it. She didn't tell me what it was and I didn't bother asking. The next invitation arrived two weeks later. This one Sydney opened and after reading it she passed ... Read full Story
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Vegas Honeymoon to Remember
I had dated my wife (Carmen) for about 6 months before we decided to Marry. One evening we were soaking in the Jacuzzi together and drinking wine. She always wants to try different things, which makes our sex life wonderful. Carmen asked me if I ever had any fantasies. I said I guess like most me... Read full Story
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When Fantasy Comes True 2
After my first threesome encounter with Jenni and her friend, getting a golden shower from three trans women was a bonus. Being drunk and now four of us snuggled in bed, i thought the night had ended but i did hope for more. I was not disappointed as Jenni's friend (Sasha) who had been sleeping d... Read full Story
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My Vancouver get a way....
I was in a different city, where no one knows me, free. My boi hole started to tingle as soon as I realized I could finally prowl the gay scene of a big city, with two and a half days of zero commitments I had little time to waste. I went to the hotel room in Abbotsford and showered, shaved and trie... Read full Story
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Pizza Delivery
She wraps her hands around the back of his head and shoves her cock harder and further into his throat. She can hear him gag and saliva burble in his throat. “FUCK I’ve needed this!” She says, pulling her cock out of his mouth and letting him take a deep gasping breath. “Holy fuck,” he says, cat... Read full Story
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The colossus and me
The colossus and me... step by step towards completion (1) When my phone rang I was watching the World’s news in TV, only tragedies. It was Lina (cf. my previous story) on the phone. The colossus with an angel heart and an elephant dick. She was in my town for business. And without her saying ano... Read full Story
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Passionate Sex with a Beautiful Shemale
a man and his shemale lover get down to business Will led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sa... Read full Story
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Buffy the Shemale Vampire Slayer Part 3
Buffy couldn't stop smiling. It felt great to have left Spike on his knees, clutching his balls in pain after she'd sucked his cock and swallowed his load of icy vampire's semen. Sex was about power, not love, and nothing made a girl feel more powerful than reducing a man-or, in Spike's case, a u... Read full Story
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SheMale Encounter
“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, besid... Read full Story
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Fantasy Reversal Chapter 6
It was late and the sun was shining through the window. The clock on the stand showed it was just before 11am. My hands wandered, to confirm I was still Katrina. As I did I recalled the night of dancing, well actually stripping and how turned on I felt. In particular, the sensation and thrill as Sam... Read full Story
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The Football Jock and Chrissie
Back in college, sharing an apartment with my BFF/roommate Kelly, a lot of my dates and hook-ups were arranged by Kelly. For some reason she always seemed to know just who was into what when it came to sex. She learned a lot about other people’s likes and dislikes from hanging with her lesbian... Read full Story
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Professor to Sissy Slut
I had just turned thirty-four and I was miserable. My wife of twelve years had left me for another man and was living with him. We were not yet in the process of filing for divorce and I was hoping she would have a change of heart. I was still in love with her but I understood why she had left. We h... Read full Story
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A very special lady
I knocked at the door, unsure of what to expect. Living in a big city for the last year, where I didn't really know anybody, had certainly put a crimp in my sex life. Where I used to live, in a much smaller town, during my high school years, I'd been able to get my dick into many tight, warm and wil... Read full Story
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Shemale Ride Along Part 1
I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass. Now... Read full Story
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Too Much Hospitality
Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned t-shirt and some ... Read full Story
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College project surprise
So this story happened while I was still in college and remains without doubt, the craziest, most exciting experience of my life. So I the story begins one day when I walking to class. I went to a big university so my walk was quite long, and the first 1/3 was just through off our campus housin... Read full Story
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badbadboi's walk in the park
...My boi hole was freshly washed, shaved and lubed with a lovely hot shower, my wand is perfect for cleaning my pussy, flushing it clean very time, I luv to let the water spray my hole driving deep enough to tickle the bottom of my prostate. My cock cage locked in place, my white crotchless panties... Read full Story
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My wonderful life with Pat : Pat birthday
Today we will received a friend of Pat for her birthday Charles and Pat are friends since the kindergarden Today Charles is married with Suzanne. Charles has followed the Pat sexual changes from young man to lady shemale. Before being with Suzanne Michel had participated to several parties... Read full Story
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I Believe
I Believe I had just started my senior year in college and was in my 3rd year of transitioning from a male to a female. I couldn’t start in high school so when I graduated and I started college I started as Nikki. The first three years working on my communications degree I used to see people goin... Read full Story
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SheMale Pussy and Cock
I once had a friend who always said "never fuck anything you can't bench-press". He was right, the biggest benefit of having sex with someone smaller and lighter than you is you can lift them easily ! On a recent trip to Thailand I couldn't take my eye's off a stunning, short, tiny but ... Read full Story
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A Revenge Fuck Part 2
Frankie had been a great sport about the entire affair. She had taken me in, she'd showed me how to become and be the beautiful woman, Josie- she had completely made me who I was, even against her will. And then she was also there to shoulder support in my emotional crisis when things did not work o... Read full Story
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Caught by Neighbour
- 1 - It was a beautiful warm day, and I had it to myself. My wife Sam was interstate on business for the week, and not due back for another five days. For me that meant housework to be done, but plenty of time to enjoy my own space, and entertain one particular hobby. I smiled to myself, and not... Read full Story
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A Visit To The Booths
I walk nervously into the booths area. My heels clacking on the floor, as I enter the darkness. I pull my dress down, as its already riding up my ass. There are a few men waiting in the first hallway, checking me out as I walk past. I smile and head into the bigger area around the corner. There are ... Read full Story
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Wife fucked by shemale
This is the story of me Rittu married to a guy named Harvinder in 1996. We had 2 kids from our marriage .Harvinder was very fond of girls and even before my marriage he use to fuck prostitutes right from young girls to middle aged women. He used to get his cock sucked and even used to fuck these pro... Read full Story
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Finally A Real Man
After my divorce I found I had some time to indulge in my many fetishes and fantasies. Those being; cross-dressing, smoking 120s and man to man sex. None of these were a factor in my separation however. It wasn't long before I was on line ordering lingerie and shopping locally. This has been going o... Read full Story
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Getting Fucked by Sasquatch
Bill was about to show up, I had known him from a chat room for years now. I was in his town for work and we had set up this date so we could finally meet each other. I heard a hard knock at the door and when I swung it open, I just stood there in awe. It wasn’t the big beard or really long hair tha... Read full Story
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Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
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CD Gone Wild
I'm a little CD slut, and get strong sexual urges that I can't control or resist. I think I'm far from passable, but men seem to think otherwise. Some men value a slut as a precious thing; the kind I look for. For that reason, I'm proud to be a slut. I love to be told what a slut I am; being called ... Read full Story
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Glory Hole Girlfriend
My boyfriend likes to take me to the local adult bookstore, into the back where the video arcade is. There's always a lot of men there, strangers that we don't know, and I feel funny when they look at me. They wonder why a pretty young woman would be back there. It smells too. A rich sweaty sc... Read full Story
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Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
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Very Impatient on a sex fanstay
Are you ready for this Mish?" "Not really but it's too late to back out now." I stood in a dark alley before a metal door shaking with both anxiety and the cold, waiting for the door slot to open and for the night to begin. I wouldn't admit it to my friend Simone but secretly I hoped we would ... Read full Story
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