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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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A Cross Dressing Suck Off Fantasy...
Yes, this is a true story that really happened to me a while back. I went out of town a few weeks ago on business, and at the same time, I was hoping to hook up for some hot man sex. I went to the Male Hookup Forum page for the city I would be visiting and posted a message. The message read " W... Read full Story
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First Cross-dressings Loosing Anal Virginity
It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... Read full Story
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First time dressing and having sex
I had some experiences with men in the past but for the most part I had been living my life as a straight man. I was in a relationship and happy. I was walking through a thrift store one day when I happened upon a form fitting stretch denim jumpsuit. For some reason this garment aroused me. I am not... Read full Story
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Cross Dressing fun at the Adult Book Store
I was chatting with a guy in San Leando, California named Jim. Jim was a 70 y/o, nasty old man black guy, 6'2", 210lbs, 8" cock and big cum filled balls. He loved to molest Cross Dressing sluts like me and wanted me to cum to his place in San Leandro and be his sexy cock sucking cum ... Read full Story
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Adult Bookstore Dancer
Adult Bookstore Fun At one time there were eight adult books in my city now there is only one. Makes me very sad as I loved dressing up like a twenty-five cent whore and visiting them on the weekends. I think I enjoy all the humiliating comments and condescending looks the customers would make abou... Read full Story
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My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
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Janine awaits
My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... Read full Story
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Ladies who Lunch - At the Gloryhole
Ladies who Lunch - At the Gloryhole By Sabrina G. Langton *** Author's Note: Hi, just a quick little story to make us all wet and squishy. Three mature crosssdressers have a little more excitement than they are used to after lunch. I hope YOU like it... *** The Boynton Tavern So w... Read full Story
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An Unwelcome Visit
It had been over a year since I had split from my boyfriend, Rick. We had a terrible row in which he had accused me of seeing another man. He walked out, never to return. I had tried to give up wearing girls' clothes afterwards in an effort to become a 'normal' person and to try to blot out some bad... 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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Fun With Friends Chapter 4
As I stepped into the shower the warm water hit my body and felt great. I relaxed my ass and let Greg's cum stream down my leg. I could not believe that in the last couple of hours I had been shown to one of my best friends as a cross-dressing slut and had now taken his cum in both my ass and mo... Read full Story
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An alumni gathering like no other
An alumni gathering like no other; Sea/Sand/Sun' and why not 'Sex' in a vancancy club; we got together to celebrate the 40th anniversary of our 1st meeting at university. The only rule was to come without a partner to relive our 'frosh' days. with friends of whom I had lost all trace, a... Read full Story
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How I became a sissy
So it all started from answering a random craigslist posting that didn't even have a picture. I was off work and horny so I was cruising the ads and I came across a Cross dressing married dom and his wife looking for a sub. I was no stranger to the lifestyle and it intrigued me so I began to write a... Read full Story
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Woman Cross Dresses for Power & Sex
Tucked in the far corner of a dark, dancehall parking lot, Sarah, also known as Robert, was having sex in a car with Joseph, also known as Josephine. Having sex in a car was no big deal. A lot of couples have sex in cars. Yet, if a passerby could see through the steamy windows, a sight to behold, ev... 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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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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My First Night of Being a Sissy Cumdump
Well I first started dressing when I was about 14. One thing that I always noticed is that putting on slutty clothes makes me an absolute whore for cock and cum. Throughout High School I dressed in my alone time but never acted on my slutty urges from fear of being caught by my parents. When I moved... 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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Claudia Coming out adventure part 1
*Author's Note: This story starts off being told in First person and after awhile the story shifts to third person* Hello everyone, my name is Claudia I am a Cross dresser who one day hopes to be transgendered, although I do not want the surgery, I am looking to eventually live my life full... Read full Story
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Do You Know A Cross-dresser?
I never considered writing a story about cross-dressing until I was confronted with it. I just recently found out that a friend of mine who I have known for several years is a cross-dresser. He's a good guy, a family man, is married with kids, and, by all accounts, appears normal. Whatever that mean... Read full Story
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First time out of the closet
I had always been more than a little interested in the world of cross dresser and she males. Since I was a teenager I had experimented with cross dressing. Usually just small stuff. As the years progressed whenever I was out of town on a business trip I would sometimes dress up in my hotel room. I a... 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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The Twink and the Bear
He stood there, slowly rubbing his hardened cock in the confines of the public toilet cubicle, trousers around his ankles, his legs adorned in black nylon stockings, held in place by the straps of his delicately laced suspender belt. It was so naughty to be playing with himself in a public place, wi... Read full Story
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Why I’m a Cock Whore!
Hello Love, The summer before my freshman year in high school. I found a VHS porno video right next to a dumpster behind our local video store. Brought it home. Couldn’t watch it until my family left to use the VHS player. It turned out to be a she male porno at first I felt weird but after watch... Read full Story
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A Reluctant Gang Bang
Hi all! I have been cross dressing and playing with men for many years now. One of My first experiences was being gang fucked by about 9 guys at an adult arcade. I was 18 at the time and it kind of traumatized me as it was pretty much a gang rape at an adult arcade. I was dressed up in a white flowe... Read full Story
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Let me introduce myself
Hi everyone this is my first time cumming out to the public. I been cross dressing for about 20 years now. I’m 30 years old now. I started dressing up in my mother’s and older sisters clothes every chance I got. Both of them had swag so I dressed cute af lol. Now it’s my girlfriends clothes. I love ... Read full Story
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Olderman and mature crossdresser Part 1
It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all. As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a c... Read full Story
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From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
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Dressing Up For My Wife
My wife and I had a bet on the football game that pitted our two rival teams against each other. It was a horrendous day for my team and hers slaughtered mine 31-0. It was the same bet we always have with each other. It is a bet where no one really loses because it ends up with us having wild kinky ... Read full Story
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A good laugh turns into a new experience
I have a friend that works in theater and makeup, one night he got tickets to a "trans" ball and invited me to go with some friends as a joke. So I figure, throw on a skirt, toss some apples in a bra throw on a wig and go party. I show up at my buddy's house around 8. I figure we're gonna ... 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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Cross dressing Aunt
CD Aunt Well, my uncle was a crossdresser, but the group is Aunt CD, so it is all kind of confusing. Back in the mid 80's I was fresh out of high school and was offered to spend the Summer with my uncle in TX, he was only 10 years older than I and was offering to let me stay with him so I could work... Read full Story
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A Flash of Lace
The insistent ringing of the phone broke my concentration and with great annoyance, I climbed off the bed and picked up the receiver. "Hey little brother!" My sister's sparkling voice filled my ear. "Di, Is that you?" I exclaimed happily "Got any more sisters I don'... Read full Story
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Φαντασιώσεις μιας Cross
Είχα γνωρίσει τον Τάκη στο Romeo. Καθαρόαιμος top, 55άρης, γεροδεμένος, πρώην ναυτικός και τώρα εισοδηματίας, όπως μου συστήθηκε. Του άρεσαν πολύ οι cross και στο chat μου μιλούσε στο θηλυκό γένος. Μου έλεγε πράγματα που θα έλεγε αν φλέρταρε με πραγματική γυναίκα. Από την αρχή επέμενε να βρεθούμε αλ... Read full Story
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Dressing Up for New Years
My wife and I attended a costume party every year to celebrate New Year's Eve. This year we decided to cross dress with her dressed as a man and me dressed as a woman. I put on her sexiest silkiest garments and she put on one of my nicest suits complete with a fedora. We had a blast at the party... Read full Story
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