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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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The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
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The Invitation Part 4
The light was gently filtering in through the curtains as Jack slowly drifted towards consciousness. For a moment or two of his half awake and half asleep state he was confused - something didn't quite feel right. He stirred in semi consciousness and his eyes shot open at the unfamiliar sensatio... Read full Story
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A Helping Hand
It was late on a Friday night when I heard my parents arguing. It always happened whenever they were getting ready to throw a big party. My mother played the role of party planner and handled all of the details, but between caterers, musicians, and the other help something always went haywire. My fa... Read full Story
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TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
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What Price Desire
I stood in front of the imposing door, my hands visibly shaking, my mind running rampant, my thoughts a jumble as I opened it. The front of the building had only the number of the business adorning it, no letters, no writing, nothing to indicate what it was. Now that I think back on it, I can unders... Read full Story
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Halloween Double Cross
It all started off so innocently... My wife Jo, tall, slim, blonde, aged 40 with 34DD tits and the sexiest big ass imaginable, works as a doctor. Her hours are long and arduous. She often comes home completely worn out. Only during the holidays does she tend to recover her sparkle. She is gorgeou... Read full Story
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Ambers torment
It seem to be the typical day for Amber as she entered the home of Master. The usual early wake up and long drive down to his house seemed nearly routine though, the last visit was a few months past and the girl was anxious for what was to come. Although, her expectations were not different from any... Read full Story
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The Mole
Police work is a paramilitary occupation. Uniforms, rank, weapons, discipline…It can be exciting and interesting for some and boring for others. Some officers seem to find lots of action during their career (or maybe it finds them) while others never use their sidearm except for target practi... Read full Story
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HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
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A Holiday Job
'Bye!' Paul stirred briefly in bed as his twin, Anne, called out as she dashed from their holiday apartment. Paul glanced at his watch; it would be a rush but she should make it to the airport in time for her flight back to England. They had been on holiday at a popular Mediterranean resort fo... Read full Story
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Aunt Cindy's Bizarre World Part 2
Chapter 7 I am guessing it was just over an hour until I heard the door open. It was her again, Miss Sindy Satin my auntie. This time she was wearing just an under bust white satin corset, long boots in satin exactly like mine but in white and her long, white bridal satin gloves and a the ribbon ... Read full Story
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Dear Karen Chapter 4
#4 05.18.09 Dear Karen, You helped me explore the fantastic feelings that breasts can produce when properly handled and I yearned to replicate the feelings that you elicited from my tits. So, since my last letter I have been training BJ to be the consummate breast lover. I have coached him in ... Read full Story
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Patrick's Treat
As usual, Maria entered my apartment as if she owned the place, slinging a bag down by the door and offering me a demure kiss. Her long dark hair had been pulled into cute bunches, one peeping out from either side of the back of her head. She was wearing a blue and white cheerleaders' uniform and wh... Read full Story
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A Murder Misstery
When I rolled out of bed that fateful morning, I had no way of knowing that it would be my last day as Matt McCoy. After showering and dressing quickly (how I long for those days!) I bolted out the door for my train, looking forward to another manic day on the floor. Although I was one of the younge... Read full Story
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The Greatest Lie Part 16
As soon as we were safely back in our hooch, I retrieved the iBook from its hiding place under the floor and opened up Spartan's main Excel spreadsheet. I re-sorted the list against the data from the last three weeks of our frustrating field work, by district, language group, age, and every other ca... Read full Story
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A Game within a Game Part 2
The first steps A few weeks later, after their 'special' marriage, on a Sunday morning, while having breakfast in their glasshouse, Helena asked Rob: "Are you up for a game, dear?" She watched Rob with some caution because she knew from the past, that 'games' did not always end well.... Read full Story
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A Game within a Game Part 3
A letter. Rob decided, after cooling down a bit from his anger which Jenny's visit had given him, to do a short survey on the things she had left. First he checked their bedroom, and like Jenny said, she didn't take anything of her make-up. He rummaged through her belongings and wasn't sure he wa... Read full Story
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Doggy Style
"OK, which exit is it?" Trish was driving with Penelope in the passenger seat up front. Meredith sat in the back behind Trish's seat with Angela behind Penelope. The quarter were sisters in a sorority attending an annual Alpha Phi event together. Every year different chapters across Sou... Read full Story
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Changling
‘My goodness!’ she exclaimed, ‘It appears that you've had an accident, youngster. You'd better come home with me so that we can make you presentable. It's quite safe, 'cos I live in the big house in the woods on the other side of the hill behind the toilets. Come along, now,’... Read full Story
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R Is For Roleplay
Chase Abernathy was exhausted. A combination of a heavy meal and a long flight had conspired to make him feel as if he’d just completed a triathlon. His shoulders ached from carrying his on-flight bags, his legs were sore from standing most of the day and his mind was numb from the effort o... Read full Story
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For a while I worked as a transsexual street prost
When I first moved to Sydney in my mid 20’s I had trouble meeting the bills. This was desperate times so after a lot of soul searching I decided that the only thing I could do was to become a prostitute. I knew Sydney that the transsexual prostitutes picked up clients on William Street near... Read full Story
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Becoming Amy
I had been dressing up in women’s clothes since I was a kid. Started with my sister’s clothes, I loved her school uniform. I used to prance around in it when I was lucky enough to have the house to myself, which wasn’t often. I loved pretending I was a school girl, and a rather nau... Read full Story
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DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
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The Invitation Part 5
This is the latest installment of a story about cross dressing and the changes in a relationship between a young man and woman at college. Bits are autobiographical, but not as much of it as I would like! If this is illegal where you live, don't read it. If this sort of thing offends you, don't ... Read full Story
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A night to remember
Josie wasn't a girl a man would turn his head for if he saw her on the streets. She was a small, petite girl, her breasts barely an B cup. She was wearing her light brown hair in an inconspicuous short cut and the thick glasses she needed for being able to see anything in her surrounding, didn'... Read full Story
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I am Baaack! Part 9
Rose stood before Joan's office door at 1:59pm. She was dressed in the same black leather outfit she had worn the night before, and she was also wearing the same "Don't fuck with me!" attitude. She had pulled herself together in the limo, assuming that Joan would have security cameras focu... Read full Story
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Damsel In Distress
1. The Request Duncan was fond of his older sister, Helen, but she pushed the boundaries of brotherly love to its limit when she asked him an unusual favour. 'Let me get this straight.' Duncan said, lounging on his bed whilst listening to the radio. 'You want me to escort you on a date with some ... Read full Story
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Fixing The Car
I had been cross dressing since I was about 10 years old, I'm now in my thirties and this story is about my first encounter with another man. It all started one day when my wife would be out for the day and I had settled down to surf the net looking for transgender sites, I was only dressed in a bla... 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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Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
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Don't Go Into The Woods
Prologue I am standing here wearing a red plaid schoolgirl uniform skirt. It is so short that although I looked in the mirror before and couldn’t see my white satin panties I felt anyone looking at me could. My blouse is a white collared blouse typical of what you’d expect to see on a... Read full Story
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A Job in the Theatre Chapter 14
Sarah and Paula shared at drink as they tried to decide what to wear for their date. "Every good outfit starts with lingerie. What do you think of these?" Paula asked holding up a pair of baby blue panties. "Nice. But I really think these will be better" Sarah said holding up ... Read full Story
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Flowers in the Heart
Chapter 1 "Hey Scott, Fauna kind of likes you," Jenna said, snickering. "Hey Jenna, it hard to hear yourself over that echo?" Scott said as he caught the football, and then heaved it back to Ronnie. "Huh?" Jenna asked, puzzled. "Yeah, your head up your ... Read full Story
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An Invitation
"Oh come on,Sarah. There has to be a way." An innocuous enough statement, but that's how it all started. I'd just received an invite to Cressida's annual Christmas party which, maybe not on the Hollywood A list, was within the cognoscenti an occasion not to be missed. The soirees of ... Read full Story
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caught crossdressing by my roommates
I am the monitor of my class and the president of the student union. On the surface, I looked glamorous, but I actually had an unknown secret - I would put on black stockings and boots every night in the dormitory and masturbate while watching pornographic movies. One day, my secret was revealed by ... Read full Story
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The Terrace View Apartments Part 7
My new life had settled into a wonderful routine. I would wake very early in the morning, usually still wrapped securely in Mistress Kendra’s arms. I would spend an hour or so working on my figure maintenance exercises, enjoy a cleansing enema, a refreshing bath and body shave, then I would la... Read full Story
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Debbie Part 5
Debbie didn't wake up until her gag was wrenched from her jaws. Her hood, collar and earplugs had already been removed. "Wake up, shit-head," Mistress spat and slapped her face hard. Debbie came awake and noticed that all the straps holing her to the couch had also been removed. She felt a... Read full Story
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Special Shemale Fun
Everyone in the hallway jumped slightly, turned and quickly looked at the tall girl near the sound of the slamming locker. Satisfied that there was no crisis at hand, the kids at the school mostly went about their business. Of course, there were the few admirers that glanced at the girl at the locke... Read full Story
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My Wife's Secret Fantasy Chapter 1
PART ONE: REALIZATION The old saying "you never really ever know some one" is quite true when it comes to my wife Debbie. Debbie has always seemed to come up with new surprises to keep our marriage stimulated and adventuresome. As I've recently found out though she seems to have been ke... Read full Story
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Beginnings
The Intimate Liaison You would think being at home all day while the wife works would give me all the time in the world to indulge myself as Michaella but not so. Being a closet crossdresser with a family and home to look after is OK but a great number of friends and family call in knowing I’... Read full Story
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The Greatest Lie Part 4
Don’t get me wrong, I don’t hate being around people. Actually, I hate being alone: it brings out the weird self-critic inside me. But god, do I hate crowds. Fall registration brought mobs to the campus. The half-empty dormitory that I had shared with a few Asian engineering students was... Read full Story
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Sabbatical or Continuous Gang Bang?
My twin sister Laura had already left to go back to college this fall season, but I had decided to take off a semester as I was totally burnt out on school and needed a break. We were twins but not identical though we did look a lot alike and roughly the same size me being a few inches taller. My... Read full Story
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Rebound
My story is nothing new, like most girls who used to be boys I knew from an early age that I was different to all my school friends. My dad was a thug of a man, who enjoyed the physical battle of the rugby pitch as much as the post match booze up, but I took after the mother who died giving birth to... Read full Story
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Filthy Little Beast
I had very few memories of my early childhood. The ones I did have were anything but pleasant. I did remember my mother and her blind hatred of my father and myself. She was very tall blonde woman with cold blue eyes named Monica. My mother always dressed in the most expensive leathers and satins in... Read full Story
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Just One of Those Days Part 3
Hello again. My name is Amanda, I'm 33 and single, since I discovered that Richard, my now ex boyfriend, was a nasty cheating bastard. He turned me into the woman I've become, confidant exhibitionist and uninhibited, especially with sex. I'm a natural blond with long hair nearly down ... Read full Story
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A Strange Romance
Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to ... Read full Story
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Lady In The House Ch. 09
A story by MicheleNylons ( Continued adventures of a cross-dressed prison prostitute. ) I lay there stunned, how had I miscalculated my effect on the Warden? The one man who could guarantee a transfer from this shit-hole; fuck!!!! The cravings of male sexual hunger within the confines of the ... Read full Story
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Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
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A Turkish Delight
My export business was beginning to take off as I was now on my second over sea's trip. I was doing business with the Turkish government and I also saw it as an opportunity to explore more my fascination of cross-dressing. I would be visiting a country where I was not know and I would blend in with ... Read full Story
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Always Be Closing Chapter 4
Tina woke me up early the next morning because we had a flight to catch. She had clearly gotten up a while before she woke me up and already had all of our stuff packed and ready to go. "I thought you deserved a little extra sleep since you covered for me last night. By the way, I already go... Read full Story
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Jamie is taken Part 3
When this process was completed the Chinese gentleman s turned to his new acquisition in the floor. He lifted him up from the floor and deposited him on a high-backed chair; his legs still folded up, and tied him to it. Then he removed the strap from around his throat and instead shoved ... Read full Story
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How I Learned To Love Drag Part 8
When we stopped shooting to break for lunch, I hurried off to visit the men's room. Or rather, the washroom in my dressing room. Walking into the spacious dressing room area, I could see that Daniel and Sean were still hard at work. Daniel, with brush in hand, was styling an auburn wig. It was lo... Read full Story
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Angel Chapter 5
On Monday morning, Angel Jones woke up smiling and with a feeling of well-being. She was still feeling the effects of the great sex that she enjoyed Friday night and Saturday morning, and the plaudits of the people at the Friday dance at the Gay, Lesbian, Bisexual and Transgendered Association. She ... Read full Story
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ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
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TO BE OR NOT TO BE – PART 3
TO BE OR NOT TO BE – PART 3 by Spanky de Bautumn Part 2. At the hotel in New York City, Sunny meets the bellhop, Antonio, and they go out for a drink when he gets off of work. The call came at exactly seven. I had woke up about five minutes before and was watching Antonio sleep. All of the oth... Read full Story
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