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The Beginning Of Penny
This story is about how I became Penny, the cock loving, tranny. I remember being a kid and jerking off to dirty mags we stole from my friend’s dad. The pics that always made me hottest were the ones in the ads in the back few pages for phone sex with trannies. Looking at those hot and perfect women... Read full Story
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Ann and I
Last night I had an awesome experience. I was down in Fort Worth to meet a tranny I had been talking to on squirt. I got off work early, took a shower and shaved my cock and balls and dressed in jeans and a t-shirt and headed down to Club Changes to meet her at four. The bar was pretty empty, Thu... 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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Chicago TG Romance
Most transgendered girls I have met want to be treated and romanced just as a normal girl would. Only in the height of passion should your animal instincts take over. I was in a Las Vegas club earlier this year and had great conversation with some tranny women. I was instructed if I wanted to meet s... Read full Story
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Las Vegas Swingers
It had been over 6 months since I seriously dated someone, and I was getting depressed and in a rut. I had directed my attention to my work and it kept me from feeling sad about my loss of someone I almost married. I had met a transsexual girl that absolutely adored, but she was tragically killed. (... 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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Halloween Night Again
Last October my girlfriend Kelly and I were drinking wine and playing cribbage on a cold, rainy night. After dating her for six months we usually stayed in on weekends. I consider myself very lucky to be dating her. She is an incredibly beautiful brunette and has a perfect 36C-24-26 figure on her 5'... Read full Story
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The Guy At The Pool
The Guy At The Pool Stepping out of my hotel room for a smoke I saw two young guys at the swimming pool which my room overlooked. One of them was standing outside the pool speaking to the other guy who was in the pool. The guy beside the pool immediately caught my attention, his shirtless bo... Read full Story
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Flight cancelled
I was on my way back from a long business trip to Chattanooga, Tennessee and deciding to hit the airport bar during my layover. As I walked up to the bar I noticed there was only one seat open. I took it. I ordered my favorite drink, an old fashioned neat with makers mark. As I sat there waiting for... Read full Story
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girls need a daddy
Friday July 18 Hello daddy, I have arranged to meet a man next week and we are in 'phone contact. He is coming to visit me and I just need to tell him whether Wednesday or Thursday. I haven't done this yet as once done is done .... I know he wants to take photos of me but I don't know if ... Read full Story
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TO BE OR NOT TO BE – PART 1
TO BE OR NOT TO BE – PART 1 by Spanky de Bautumn This is a story about how taking a play to New York City changed people's lives. A transgender coming of age story. I was born Harold Stanley Dayes, not a great name for a kid growing up. I know my parents loved me, but Harold was my mom's dad a... Read full Story
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TO BE OR NOT TO BE - PART 7
TO BE OR NOT TO BE - PART 7 by Spanky de Bautumn Part 6. Sunny, Mel, and Shari had a heart to heart and Mark took Sunny for a night on the town. I woke up next to Mark, he looked so peaceful sleeping. Was I dreaming? Did I fall asleep and dream that Mark said he was going to take me shopping... Read full Story
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A different couple
I am Hans, as I already mentioned in my previous story, I am a mature guy (47 years old) who came to the Island of Tenerife more than two decades ago. I am a drinker, a womanizer and a gambler. In these more than 20 years I have seen them in all colors. I have made a lot of money and lost as much, I... 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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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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Regina and Tommy
I was getting fucked hard and aggressively by a certified bad boy named Tommy. I've never been the kind of girl who liked bad boys until I met Tommy. Tommy like doing all kinds of wild crazy things to me and I was under a spell and couldn’t object. Tommy was like the asspussy whisperer and he gave m... Read full Story
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Amy and the Straight Jocks PT1
Only a couple close friends knew for sure and most others knew it as just a rumor. Amy dressed and lived life as a girl like she had since the start of high school when she moved from a new town. The jocks would laugh and whisper to each other when she walked by debating if the rumors were true. Co... Read full Story
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First Time I Experienced Eating a Tgirl Out
So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... Read full Story
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Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
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Alessia Travestita’s Adventures – Game, Set and Match
Chapter 1 – A chance meeting? Alessia sipped her double-espresso slowly, savouring the strong flavour and the sweet aroma as she gazed absent-mindedly out of the window, watching the passers-by on the walkway outside the coffee shop. It was approaching mid-day so she had chosen to sit inside out of... Read full Story
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Lola Chapter 5
Lola chapter 5 Summer vacation was coming to an end. Most of the time we had been to ourselves, mostly at home but also a couple of shorter trips. Beer tasting in Stockholm's archipelago, a trip to the west coast, overnight stays in hotels, everywhere we were received like any other couple. A fam... Read full Story
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Seduced Willingly Part 2
She must have had on lacy silky panties, but cause as she picked up the rythm doing my back and lower back with her hands, her cock was slowing sliding up and down. I was literally having butterflies, I was probably trembling in my thighs and precum was leaking out of me like a faucet. I was more tu... Read full Story
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Adventures of Shemale Sandra Part 1
His name was Phillip. Or at least it had been. Honestly, he wasn't sure who he was; all he knew was that what he had done two years ago was what he thought was right. This was the lifestyle he wanted. It should be said that Phillip has always had strong female influences throughout his life. He a... Read full Story
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Shemale Fantasy - Suck Fest
This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behi... Read full Story
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Clinton
"How many inches?" she asked. "Twelve," he said. "Really?" "Really." "If you're lying, you're just wasting your time." And mine, she thought. "I'm not." "Okay, then. It's a date." Tiffany hoped the jerk was te... Read full Story
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Allison is Born
What a wonderful day this is. This is the first day of my new life but before that I should give you some history about me. My name is Allison, I am a 24 year old male that lives in a small town in Ohio. My father died when I was very young and I was raised by my mother. I guess you could say I am i... Read full Story
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Man Is Humiliated By Escort
I am a very adventurous, open minded married guy. I am 6'2", 150lbs and I have a 5" cock. My wife (Mary) is great but she is very straight laced and doesn't like to have sex but twice a year so I decided to look elsewhere to fulfill a few fantasies. I am sure my size and stamina have a lot... Read full Story
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The Client
Meeting the client and selling your firm's abilities to the client's firm is about the toughest part of the business of being in the contract evidence collection business. Invariably you want a lot more for the work than the client thinks it's worth. This is partly a function of time estimates, or m... Read full Story
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Experimenting with Cock
I was 22 and at the time did not have a girlfriend. I had a habit of jerking off at least once a day if not more. Starting masturbation at an early age made me bored by "normal" porn star videos. Leading me to amateur porn. Soon that became boring and I was experimenting with everything. O... Read full Story
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Happy Halloween
Hello my name is Mike! Let me tell you a little about myself for the story. I'm about 5 foot 5 and thin, about 135bls. I am half white and half hispanic, so i have a nice light brown complextion. I don't have much body hair and am very GAY! I have always know that I was gay, there was never... Read full Story
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Flying High
The plane landed as scheduled. Luckily it had been a very smooth flight. I made my way through the busy airport. While I was waiting for my luggage my eyes went everywhere looking for beautiful girls. I saw my luggage come around and went for it. At the same time a voluptuous brunette reached for th... Read full Story
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Bar trap Part 2
I was supposed to put on heavy makeup. Starting with the foundation, I applied a generous layer of a brand especially designed for the use on stage, that did a very good job covering up any dark shadows. After I was satisfied with the effect, I used a brush to put on powder and make it all smoot... Read full Story
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Hidden surprise
Midori slowly made her way around the sumptuously appointed living room before stopping by the window to take in the breath taking view of Central Park. "I just love your place," the cute twenty something Japanese American called out, "but the rent must cost you a fortune!" A voi... Read full Story
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Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
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Fantasies Fulfilled
I enjoy crossdressing and do so when ever I can. About the only time I dress as a man is to go to work. I have been doing this since I was eleven years old. I love to have sex with a man as if I was a woman and really think I should have been born a girl. I think like a girl and naturally act like a... Read full Story
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A Revenge Fuck Part 3
Chase gripped my ass-cheeks and plied them apart, shoving his cock up, balls deep into me. My legs, stuck up into the air and folded back, my knees bouncing there even with my head as he fucked me there in his car. We faced each other, panting and kissing, hot breath and saliva mixing. His ruddy coc... Read full Story
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Black Mafia - 1975
Bucky Collins downed the last of his whiskey and collected his chips to cash in. His cousin, Don Lee, who served as his driver and bodyguard escorted the Black Mafia attorney-slash-lieutenant to front door. His leisure trip to the Big Apple had been fruitful. Tonight, his winnings totaled $2,300.00.... Read full Story
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A Tranny Whores Tale Chapter 2
By the time I pulled up near the house it was 4am. I was drunk, completely revved up and ready for some action. I emptied my pockets of everything except Elle's 'offering'. I took my last swig of vodka from the bottle and took one last deep breath. "He we go, again." I thought. Here I am 4... Read full Story
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Defend Each Other
San Francisco International Airport, San Francisco Ca. Main Terminal area 12:35 a.m. 16 September. Alex sat in the quiet airport terminal, fixing her lipstick in a small compact and checking her make-up, waiting for John to arrive from Japan. John had gone to Japan to convince his investor in ... Read full Story
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Your Best Damn Girlfriend Ever
There are times in a young man's life when it is so full of fun and sex that it's a wonder they survive. College is one of those times for many young men and it certainly was for me. I attended a small private collage in southwestern Ohio at a time when the world seemed to be totally focused on it's... Read full Story
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On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
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Roberta, Molly and Ed
Friday "Commander Cromartie?" Lt. Commander Edward Cromartie, USN, turned toward the voice that had spoken his name. He saw two female naval officers, a tall willowy light-skin Black woman, and a short Asian one. The Black one was wearing the uniform of a full commander, the Asian of... Read full Story
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Down the Path Part 3
I haven't been able to concentrate all day, didn't get anything done. All I can think about is having to go back to the bookstore tonight. I don't know if I can do it but if I don't I'm not sure what he might do. Maybe he just won't contact me anymore and I really don't want that. More troubling is ... Read full Story
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Dirty Business Trip
Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and he... Read full Story
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Discovering Mistress Sarah's World Part 6
Chapter 15 Joe's first 'female' public appearance as Josie was approaching fast. He was nervous about it. Fortunately Mistress Sarah had kept him busy most of the day so his mind was distracted. Shortly after his mind blowing masturbation session with her in the morning, she left to run errands a... 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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Proud To Be A Sissy Chapter 7
"You're being really dirty little sissy slut today," daddy chuckled and asked, "What's gotten into you?" "Making up for the last few days I guess," I giggled hugging him tightly, "and I missed you too." "I missed my little sissy too." He repl... Read full Story
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Proud To Be A Sissy Chapter 8
I woke up to hear daddy lightly snoring and in my sleep I had draped a leg over him so that my body was almost covering him. I giggled to myself realizing that even in my sleep the sissy slut in me reached to grasp his flaccid penis. Then I curled closer up against daddy and contemplated about how m... 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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Horny Aerobic Instructor
Carla is big on aerobic workouts and she loved watching her instructor's muscles as he worked out hard with them. His hot sweaty muscular body did wonders for Carla's sexual appetite. She puffed around the room when he did, did step-ups when he did them she always worked out at the front of the c... Read full Story
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A New TS Slut is born
There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried i... Read full Story
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Cindy She Thong
Dialogue from Cindy’s point of View: Her name is Cindy and she is a shemale. Cindy is a beautiful woman is every way except one. She does not like the term tranny and prefers being referred to as a shemale. She is truly happy living as a woman. She began taking light doses of hormones at 19 she had... Read full Story
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My amazing date with Miranda M.
I arrived a few minutes early. I'll admit it, I was extremely nervous. I gathered my confidence and knocked on the door. In a minute or so, The door opened and she was standing there, My Goddess! "You look amazing Miranda" I said. She smiled and thanked me as she invited me in ... Read full Story
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Cindy and Juanita Kinky Shemales
Her name was Cindy and she had been born a male. Cindy was a beautiful woman is every way except one. She didn't like the term tranny and preferred being referred to as a shemale. She was truly happy living as a woman. She began taking light doses of hormones at 19 she had stopped hormones beca... Read full Story
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Bikini contest
I was at this beach bar in Mt Pleasant SC. There was a bikini contest that day. As I attended, the contest started. I was 23yrs old and the thought never crossed my mind about a tranny. However this was supposed to be all girls. Nobody, including me suspected this girl that won the contest was a tr... Read full Story
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My 1st transgender experience
Many years ago I was living near the San Francisco area. I had purchased the most recent Hustler magazine and one of the layouts had Shannon. She was so beautiful, and oh my what a cock. I had only ever been with women and did not consider myself gay, but for some reason I wanted to suck that cock. ... Read full Story
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