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Jobe, Cross Dresser Extraordinaire
I used to be pretty bored. Not last week, or a mouth ago, but the last twenty five years. Life has just always seemed to be… dull. But lately, things have been looking up. I grew my hair out recently, I've got black hair, I'm tall and skinny, perfect body to pretend you're a girl in. I'm t... Read full Story
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Caught cross dressed Part 3
The next few days felt like a lifetime for me. I couldn't sleep at night - every time I closed my eyes, all I could see were replays of myself, dressed like a whore, being strapped to a padded sawhorse while it fucked me from both sides. Everything I ate and drank had a horrid aftertaste of that bas... Read full Story
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Jamie is taken Part 1
Jamie loved his job. Not only did he enjoy the job itself, but it also provided him with outstanding opportunities when it came to getting laid. Jamie was 21 years old and had moved to the city eighteen months before. Not long after he had gotten the job, working as a sales clerk and tai... Read full Story
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Jamie is taken Part 2
Jamie came to on the cold dungeon floor retching and coughing, his mind paralyzed by a mixture of pleasure and panic. He had loved the orgasm he had just experienced. His experience with breathplay was less than half a day old and already he knew that he loved it almost as much as finally ... Read full Story
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I am Baaack! Part 2
Louise Edwards, behind her Art Deco desk in her office at Transformation Systems, leaned back in her designer chair, set down her cup of coffee - black, regular, thank you - and looked with satisfaction through her open door at her secretary seated at his desk in the outer lobby. Not "his"... Read full Story
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I am Baaack! Part 4
It was 2:00pm, exactly five weeks after The Meeting. Jessica stood fidgeting behind the Vaingirls cash register. Things had returned to seeming normalcy after The Meeting, but all the secondary participants in Rose's plan knew it was like the Phony War of 1939/40, and that things were being done beh... Read full Story
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I am Baaack! Part 11
Now Rose upped her sincerity level. "I want that kind of friendship with you, Joan! I believe we are kindred spirits. If two manipulative bitches like us CAN be friends, I think we should be. I did this little scenario today as a show of skill, inclination, and sincerity. Could I do to other me... Read full Story
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The Birthday Gift Part 2
This story continues the events started in "The Birthday Gift." If you want the full effect you should go back and read part one. If you like it, and this story as well, be sure to vote and leave feedback. The TV standing in front of the bed showed the scene we had watched I don't know ... Read full Story
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Judi's Fantasy
When I got home I could hardly stop thinking about the wild night with Judi. I didn't even care if my wallet was empty. I was going to work plenty of overtime that next month to make up for it. Judi gave me specific orders not to call her but she would call me whenever she was not busy. About two da... Read full Story
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The Greatest Lie Part 7
The horrible memory of my crackhouse ordeal faded much as the lurid surgical site on my abdomen faded to a faint pink smile at my bikini line. I went off the AIDS cocktail after one awful month of constant nausea, and was pronounced antibody-free. My surgeons pronounced me healed and recovered. Natu... Read full Story
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Tilted Kilt Chapter 4
Like most mornings after a late shift at the Tilted Kilt, I awake around 11 am and lay in bed as the day comes into focus. The sheets felt cool on my nude body and I realized my roommate, Shari, had left the air conditioner on before she left for work. It's Summer in San Diego and the days of late h... Read full Story
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THE WONDERFUL ADVENTURES OF MISS K: QUEEN OF THE ROAD
Miss K drove the car through the Midwestern countryside, enjoying the early spring breeze that leaked through the SUV's window as it blew through her platinum blonde hair. Her tits were held up by the tight, white, midriff-baring top she wore that stopped just below the lower curve of her tits... Read full Story
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Can I Be This Lucky?
I had just broken up with my wife of 4 years. So I was definitely not feeling good about myself. My time in the Navy was just about up, & not a second too soon. Now that I was done with my wife, I had no reason to stick around here anyway. I decided to go check out a movie to get my mind off thi... Read full Story
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Buying Time
It’s a hundred dollars to use the sex machine in the public restroom. Insert a couple of fifty-dollar coins into the payment slot to remain anonymous, though of course it’s more convenient to just let the data terminal do a neural scan and auto-debit your account. A hundred bucks buys... 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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Beefy Buns
It's hard to get good help. Probably, that's true in any business, but it's especially difficult to find decent employees in the fast food racket. Believe me; I've tried. I manage the local Beefy Buns franchise--burgers, fries, and shakes is our mainstay, but the menu also features fish and chick... 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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Billy Is Billie on Halloween
It was October 30th when I first found out who I really was, a cock sucking cum drinking whore that needed to be fucked. For so long I have dreamed of women without having any luck actually being with them. With my very feminine figure and shoulder length hair I was always pushed aside for the bigge... Read full Story
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Caught by my Sister Chapter 4
I woke up late on Sunday with the distinct taste of cum still in my mouth from the night before. For the life of me I couldn't even remember how many cocks I sucked at the party. I slowly got myself out of bed and took a long hot shower. It took me a long time to scrub all of the dried cum from m... Read full Story
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Fantasy Reversal Chapter 5
Thankfully I had taken the week off work, or at Katrina had prearranged my week off prior to the switch. Though as the week had progressed I was less sure that Katrina was in my former body of Sam. None the less ass the week progressed I was growing increasingly comfortable as Katrina, and in most c... Read full Story
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Yellow Polka Dot Bikini(s)
"She was afraid to come out of the locker. She was as nervous as she could be. She was afraid to come out of the locker. She was afraid that somebody would see. Two, three, four, tell the people what she wore. It was an itsy, bitsy, teenie, weenie, yellow polka-dot bikini that she wore for the ... Read full Story
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Bringing Daddy's Work Home
"Whew! I can't believe this shit." Marilyn Walker, recent high school graduate, stared into the reflection in the bathroom mirror and breathed deeply, thinking to herself about her latest situation. Here, she was standing in the bathroom of the office of some city bureaucrat whose name ... Read full Story
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Alexis Chapter 3
The beginning of the next week goes by rather uneventfully. Mr. Hughes doesn't acknowledge me in class, and I'm starting to wonder if he's regretting everything we had done. My suspicions are proven wrong however on Wednesday. The bell rings and kids scramble to get out the door for lunch. I'm sl... Read full Story
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First Time Out
I'm so excited and want to relate this 100% true story quickly while it's still fresh. Please forgive any typos. [My background: Age 48. Closet dressing in earnest for 15 years. Began with slips stockings and nighties but have collected extensive full wardrobe and accessories over time. Boobs, wi... Read full Story
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First Time S & M Whore
Suellen certainly looked the part of a cheap S & M whore: black seamed hose, shiny pink patent 5 inch heels, a black leather miniskirt, and a translucent white nylon blouse that clearly showed the black bra underneath. Her long blonde hair swayed seductively and naturally. Well the hair was natu... Read full Story
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Amber Becomes a Reality
Over the years I had fantasized more and more about kinky sex. At first it was just a little kinky but after surfing the Internet I have wanted to try almost anything and everything. The problem was I had been dating Jen. She wonderful and beautiful but she was not kinky at all. I would have loved t... Read full Story
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Doubly Endowed
There was a very real sense in which Eunice could be considered doubly endowed. Not only was she a very attractive young girl, possessed of a proud pair of breasts, with good-sized nipples, and a slender figure, she was also possessed of an asset which even in these more enlightened times was a matt... Read full Story
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Forced Entry
Danny sat at the bar of the Holiday Inn nursing his fourth double scotch, espousing to the man beside him the reasons why his company was the best designer and distributor of accounting software in the world. Danny was a large man in his forties and was running to fat. He was dressed in a travel-... Read full Story
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An Unexpected Encounter
Alexander entered the bar with trepidation. He really, really hated going out to new places to get fucked up, but dealing with his friends at the bar just down the street from his place wasn't an option. He'd -- albeit accidentally -- wrecked his best friend's car into the side of the bar. To be fai... Read full Story
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Maxine and Pam's Love Story
Oh, that Dominant TV was so mean! She really did rape and humiliate both of us. I will never consent to having her over again. I am so so sorry I thought of having a Dom play with us. It seemed like it would a real turn-on for both of us when we picked her up at the CD bar. I thought it would be fun... Read full Story
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Whatever It Takes? Chapter 2
"Every thing all right?" Penny asked. She was standing there wearing a baggy rugby shirt, loose fitting boot-cut jeans and a pair of timberland boots. She looked very sexy, even though her clothes were not particularly feminine. Then in stark contrast, there was me. I was standing in... Read full Story
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Male or Shemale, Still a Slut
Part 1 My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond ... Read full Story
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Old Folks Chapter 1
I had been cross-dressing for some years, but I had never been with another man. I had been talking on a gay chat site for some months when I found someone who I got on with well. We exchanged photos I was happy with his and he was happy with mine. Deciding to get together, we arranged a date and ti... Read full Story
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Blow Job
My e-mail is: My rusted, green Toyota Tercel pulls into the mall parking lot. I pick a spot at the back, beyond where even employees park. The next car is a blue pickup 20 spots away. No one parks here, except at Christmas. But I know that I'll soon need the privacy. I'm a freak, a cross-dresser... Read full Story
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Never Wanted To Be Your Girlfriend Ch. 02
So, after being made up like a slut, left glued to a pair of silicon breast forms, and caught sucking-off my best friend, I was pretty sure my day couldn't get any worse, but I had come nowhere near the end of my torment, as Michelle now had something else planned that I was probably not going to li... Read full Story
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Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
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Sara by Sara
1000 – Sissy Story 29 – Sara by Sara Filed Under: Sara, Sissy Story by Anna Malice — 3 CommentsFebruary 26, 2012 4.00 avg. rating (81% score) - 3 votes Post number #1.000 I never thought to reach this moment.. in truth i always thought to cancel this blog.. a lot of time before of this.... Read full Story
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Becoming Zoe
My soon to be wife Annie had taken a job out of town and I only saw her every two weeks or so. I was so missing her. She and I had become long distance lovers. She was scheduled for a flight home on Friday night. I was going to pick up her son Zakk from his dorm and the two of us were going to p... Read full Story
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Lady In The House Ch. 05
A story by MicheleNylons (Crossdressed prisoner is forced into prostitution.) From Part IV Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread th... Read full Story
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Lady In The House Ch. 13
A story by MicheleNylons ( Transvestite prison prostitute gets a visit from the Warden. ) I awoke in my cell the next morning unaware of the terrible fate that had befallen my sister Angie. I knew that Steve had sent his henchman Danny to do something to her in retribution for my recalcitrance bu... Read full Story
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Camming Down the Rabbit Hole Ch. 08
A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... Read full Story
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The Golf Bet
A couple of years ago I joined a new golf course, I wasn't the best golfer but very keen, I would be at the practice area almost everyday for at least an hour. Over this time I got to know a number of members and it was a good way of meeting people to play with. Over that year I met a number of new... Read full Story
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The Big Mature Shemale Next Door
The Big Mature Shemale Next Door SugarandSalt "Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mir... Read full Story
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Tight Spot
XtinaSmith2017 Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavor but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way ... Read full Story
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Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
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Amsterdam
zNote: This story evolves around a "shemale" so there is some bi-sexuality in the telling of this tale. If that's not your cup of tea, then please, don't bother reading it. Thank you. Amsterdam My wife and I had flown over from the states to visit with her parents who lived there. I ... Read full Story
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Sweet Sherri
"The fuck you want," the girl hissed through her teeth. Well, it's hard to say. For one, this was the one night of the week at the particular club that was tranny night. Unless the lucky woman was either a straight freak or had been exposed to the scene, there weren't too many people wa... Read full Story
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Sexretary
Sam Nichols had a comfortable, reasonably well paid job in a computing firm called Stewart Computing. He was twenty two and had recently graduated college and had been lucky to find such a good job in the firm on the edge of San Diego, just a couple of hours drive away from where his parents still l... Read full Story
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Headmistress' Favorite Sport Part 6
At Mistress Rachel and Master Tony's house Denise was pushed into the role of maid along side her mother, Susanna. Susanna had been reshaped exactly as Mistress Rachel wanted it. She was now a devoted little nymphomaniac slave who loved her mistress and master and who would do anything for them. Lik... Read full Story
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Headmistress' Favorite Sport Part 10
When Denise came to she was lying in bed. She had been washed and she could no longer feel the annoying diaper rash. In fact she felt fine, clean and well rested. On her feet were what turned out to be black Oxfords with seven-inch heels. Her ankles were in steel cuffs and connected by a eight-inch ... Read full Story
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I am Baaack! Part 1
PROLOGUE: Ross Thorn, aka Nick Mitchell, paced back and forth in his office high up in the Hancock Building. He glanced out the corner windows. North you could see out over Chicago's North Side to almost as far as Wilmette, and east out over the lake almost to Michigan. It was a perfect spring da... Read full Story
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I am Baaack! Part 5
Joan hung up the phone. One of what she liked to think of as "Dr. Adkin's Rules for Having It All.And Keeping It" was, "Always expect the unexpected", but this had thrown even her for somewhat of a loop. Rose was still alive! Not only alive, but here in Chicago and wanting to mee... Read full Story
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April Fools!!
I'm Jimmy James and I've been hanging out with the same six guys since we started college. We're a pretty close knit bunch and have stayed in touch since then. At 25, I'm the only one of the seven of us still not married. Even though we all still get together for parties and get togethers, for t... Read full Story
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Old Folks
I had been cross-dressing for some years, but I had never been with another man. I had been talking on a gay chat site for some months when I found someone who I got on with well. We exchanged photos I was happy with his and he was happy with mine. Deciding to get together, we arranged a date and ti... Read full Story
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Old Folks Part 2
It had been eleven months since that day when I arrived at Honey and Frank's house. It was about 1am at night as I stood in a quiet street waiting for Frank to pick me up. I had just finished with my last client for the night a good blowjob with him ending up cumming on my face. I was touching up my... Read full Story
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The Greatest Lie Part 3
My weekend escapade with my first real lover, Jake, convinced me that I was destined to live as a girl, despite having been born a boy. Unfortunately, it was my male persona to whom the University of Minnesota had extended admission and a scholarship, and I wasn’t quite sure how they would rea... Read full Story
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