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Jack & Jill - his first time with a transexual
Jack and Jill meet It was when I went to the patio to enjoy a cigar after dinner that we met. On the road for business, I found a decent bar and grill near my hotel where I was welcome to enjoy a fine smoke. I had dinner and then moved outside for a relaxing smoke in the cool weather. I lighte... Read full Story
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My Dominate Spanish Mistress Parts two and three
I wasn't going to write anymore for this story but i posted the first part of the story on 99chan's elit board which a recommend going to. Maybe with the help of some of you people writing or encouraging more writers on their stories the board might return to its former glory. After all some guy sa... Read full Story
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I Can't Control It
Woke up, laying on my left side, to the sound of Marissa making quiet whimpering noises. I knew it was her because she had an unmistakable “little girl” voice that she moaned with while we had sex. Or while she masturbated. Just whenever she had pleasure.. down there... My back was to ... Read full Story
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And Then There Was Eve
There was an assortment of eclectic regulars at the coffeehouse I owned. The Hipster Café was in fact the hippest place in the East Village. Some would dare pronounce it the hippest place to down java in all of Manhattan. We had fun. Sure we worked hard, but it was always fun opening our stag... 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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Emily and Steve Part 1
As I pulled my cock out of Emily's ass and shot my load onto her flat stomach, where my cum mixed with the load the beautiful blonde cross-dresser had just shot from her throbbing cock a moment before, I thought to myself that work was suddenly going to be a lot more fun. My name is Steve and I w... Read full Story
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Bend That Gender
Shannon's Shocking Discovery Shannon leaned against Marilyn. She was definitely light-headed from her last drink. Marilyn's hand resting on her left hip pulled her closer, a move at once comforting and unsettling. She slid her arm around her new friend's waist, resting her head on the silk covere... Read full Story
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The club
"Okay ladies," Missy said to her guests, "relax and get ready because I have a very special treat for today's meeting!" "What is it?" and excited Jayne asked while removing her sweat shirt and jeans. "Now you know better than to than that" Missy replied with a... Read full Story
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A Real Fantasy
It was a boring Wednesday evening. I was away from home on business. With nobody to talk to and nothing good on the TV I decided to go for a walk. I walked for a few blocks and noticed the neighborhood was changing from hotels and bars to strip clubs and adult bookstores. I had never been to a strip... Read full Story
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Boys will be Girls
Jack sat at the bar, his eyes moving about the dimly lit room as he sized up the possibilities. He was relatively new to town and had yet to draw a circle of friends around him. He was the sort of fellow that typically drew others toward him. He was handsome, athletic and wealthy, but it was his fri... Read full Story
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Transsexual Sisters Chapter 5
Part 5: A friend is forced to say goodbye Cassie had made things right with Michelle and Nicole. She now had to square things with Randy. She found him in the hospital lounge. "Hi Randy, can we talk?" "About what? I think you made things pretty clear the other night." ... Read full Story
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Christy's Fantasy Come True Chapter 6
The alarm went off and Christy rolled over and hit the off button. The clock face was starting back at her flashing 8:00. Since it was Friday she had slept in a bit. Jim had gotten up early and left for work after spending the night. They had gotten into a minor argument last night but came to a... Read full Story
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Lady and the Cop continued
The next night Regina got a visit from. Larry the cop who openly declared war on shemales and trannies. He was working a homicide where a trannie friend had been killed in her apartment. Larry was a known shemale hater and he never failed to express his opinions. Tonight he was in her apartment to ... Read full Story
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Gym time surprise
Another day, another gym session. Kelly was not looking forward to her gym session, she was bored of doing the same old routine and just going through the motions. She knew she was hot, she knew she didn't need to work at it. She wanted to go home and chill and play with herself as she'd seen that h... Read full Story
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Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
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A Stitch in Time Saves Nine
I'm lucky to have met Frankie. She's not one in a million, not with (at last count) one in ten males transitioning to shemales, but she's still a relatively rare find. We females who are transitioning to hemales, on the other hand, currently number thirty-three percent of the world's population! Fem... Read full Story
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A Special Girl
Please allow me to introduce myself. My name is Steven Brun. I'm a young Black guy living in the city of Boston. I recently graduated from high school and started college. I go to Boston College. It's a school full of rich white kids but I'm liking it so far. The city is big, much bigger than the sm... Read full Story
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Brazilian Discovery Chapter 3
Chapter 03: Partying in Copacabana On the Ipanema beach, Barbara and Joan were joined by Tereza and Consuela. The beach was less crowded than the Copacabana one. Tereza pulled down her shorts and her T-shirt to appear in a quite hot red bikini, an uplift bra that was supported only by a band arou... Read full Story
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Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... Read full Story
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Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
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TG girlfriend is my new neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
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Being taught a lesson .......... I think!
How did I end up on my back in my own bed, legs straight up with my ankles over her shoulders, ready to have my ass fucked from a lost bet? A bet that Alma clearly cheated at as we discover. I was off to Thailand for a 16 week course in Thai massage at a school recommended highly by a friend I ha... Read full Story
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A T-Girl Fairy Tale
Jared tossed the last bit of horse manure onto the highly stacked wheelbarrow. With a heavy sigh he gripped the handles and lifted. His muscular arms strained and bulged as he pushed the unwieldy load out the stable door to the large pile where he would deposit it until it was needed for the gardens... Read full Story
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Mike and Chris Together
Mike's sex life had taken a definite series of turns for the worse. When he called one of his favorite partners, Stella, she apologized for not returning his earlier calls, and told him she had been very busy lately. "I'm really sorry, Mike. I've had some great times with you, and I will alw... Read full Story
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Angel & Two More Men
The sex on Friday night and Saturday with Bob Marley Cliff was the best Angel had experienced up until that date, but it was only one of many fabulous carnal adventures in her life. Because of her beauty, her sexual prowess and her reputation as a woman who was free and open with her charms, she had... Read full Story
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Angel Chapter 2
Angel Jones stepped off the train and hoped she was in the right place. It was noisy and confusing in the terminal, a far cry from the relatively quiet station in her home town where she had boarded the train that morning. One hand clutched a small suitcase that contained her makeup and clean linger... Read full Story
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Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
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Sissy Crissi Chapter 1
Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need ... Read full Story
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How I Met Alyssa
I groaned as the sun was shining onto my face. I turned around so I could get some more sleep, but I saw it was 9:22 am and I decided it was time to get up. I got out of bed and went to the bathroom of my little apartment to freshen up a bit. I looked at myself in the mirror and saw a 20 year o... Read full Story
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The Curse (Sissy Story) by sdvine
I wasn't really having a good time that night at the bar. Truth be told, I had been practically dragged out in the first place by my best friend Joe, who told me he was tired of me "sitting on (my) ass" every night "finding new ways to be boring." Quite frankly, if this is what qualified as being no... 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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Francine Hung Red Head Part 2
This is the second part of 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 Cali... Read full Story
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Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
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Gemini Sluts and Gang
My good friend Renee and I had set up a double date gang bang for tonight now that she was finally out of the closet and ready. She has decided that life is too short to remain in the closet and miss out on all the fun. Renee and I have so much in common. Besides loving sex, we both have a fetish f... Read full Story
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Lost Girlfriend Part 2
I was in a pretty pissed off mood for a few days, having just lost my latest hot Tg girlfriend, Kelli to Alesha, a well hung black Tg, and decided to go to my favorite exotic dancers club. I recently had some interesting adventures with several of the dancers, I wrote that up in a 2 part short ... Read full Story
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Bikini Boy
I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage... Read full Story
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Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
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Five Into Three Does Not Go
Kristina It is waspish in the late evening out in the open in Portsmouth Harbour as we step out of the vehicle and walk over to the private section of the docks, the sign says Ceres St docks. Dark has long since fallen but lights, white, yellow and orange light up the skies. The feeling is one of... Read full Story
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I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... 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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A Revenge Fuck
It had been a long day. I had fought the traffic after a miserable week to get home early and surprise my wife for what was to be a romantic weekend. But as I pulled up to the house my heart sank. I saw a bright red motorcycle in the drive way and something inside told me, "This isn't right!&qu... Read full Story
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David to Dee Chapter 2
His nipples had grown considerably over the last two months. Gina had been putting those little nipple suckers on him twice a day. Dave wouldn't be going to the gym anymore. Well, it had been a long time since he'd gone to the gym, anyway. Since Gina had had him shave his entire body, last spring... Read full Story
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Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
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Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
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Betrayed Chapter 7
Angie kept my arm locked in hers, preventing any attempt at escape. We caught a cab back to my place. She was even more appreciative of it than Dianna had been. "Girlfriend, you live like a queen!" she exuded. Realizing what she had just said, she giggled. "Oops! Well, you kn... Read full Story
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Intro to a Dream Made Real
Jim had known growing up that he enjoyed bi-sexuality. But he had never found a man attractive the way women were to him. For example, he never found himself wanting to kiss a man, but he liked holding a hard cock as much as he enjoyed touching a wet pussy. He really enjoyed sucking a dick as much a... Read full Story
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Betrayed Chapter 10
I would have loved to be waiting at the gate at O'Hare when Dianna de-planed from L.A. that Sunday night. I had to settle for the Baggage Claim Area. Those people working for the Transportation Security Administration have no sense of humor. I guess at eight dollars an hour, they can't afford one. T... Read full Story
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My Wife's Fantasy
I am originally from Brazil but moved to the USA when I was an infant with my parents when my father was transferred with his job. I married a Latina girl from Texas just a few months ago. Lydia has always been a sexual partner that enjoys different things. After a while as everyone usually does we ... Read full Story
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The Greatest Lie Part 1
The greatest lie that they tell you is that what happens in high school doesn't really matter: that life begins in college. I pretended to agree, though I never believed it. For as you will see, I am the world's greatest liar. "Take Sadie Hawkins Day, for example," I said to my buddy Qu... Read full Story
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Betrayed Chapter 6
Monday was the most vile, loathsome day of my life – for no earthly reason other than having to be me. The first thing I had to come to grips with was who 'me' was that particular morning. 'Lance' had to put in an appearance at the office. Back to the old routine, go out there and make the big... Read full Story
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The Greatest Lie Part 18
They say that prostitution is the oldest profession. I disagree. Some guy must have been a professional hunter to have gotten together the spare change to pay for that first commercial fuck. It's like that chicken and egg conundrum. Eggs definitely came first. Just as mutation precedes evolution, th... Read full Story
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The game show,
One day i was looking through a number of competitions and trying to find a way to make some easy quick money. A number of applications were sent, mostly for junk i didn't need or for competitions I knew I had no chance of winning. For example, the types you get $30,000 for answering the easiest que... Read full Story
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Force of passion
::The Ebon Hawk hurtled along silently through hyperspace. The Jedi Exile, Shi'la Raan, watched the white stretching stars as they headed towards Korriban. She felt uncomfortable heading to a planet that was a graveyard for Sith. It was like a darkness in the back of her mind; a whisper in the force... Read full Story
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Angel Chapter 6
This is an entry in the Literotica Winter Holiday Contest, and is part of an ongoing series on the life of Angel Jones, a beautiful young T-girl in London. For more detailed information on her and on the other characters who appear in this story, please see previous episodes. Angel Jones was uns... Read full Story
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My First Time Out Part 3
Angelo was still working on Shayna's blonde wig. He fussed with it, combed it, and teased it. Angelo knew a romantic style was very important to Sir Dominique. Shayna was escorted to a tremendous makeup table. Saki placed a headband on her that stretched her scalp and raised her non-existent eyeb... Read full Story
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The Greatest Lie Part 19
The booked me as Alex Rios and handed me an orange jump suit and slip-on boots. I changed in a tiny curtained alcove and relinquished my clothes, shoes and purse, and became Inmate 265743. The booking clerk ignored my pleading eyes, so I begged. "You can't put me into a male population. I... Read full Story
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