Free Stories

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What do you do on a first date?
Well, first thing Id like to do is have us both get naked and take a shower. Id get you all lathered up in soapy suds and start to shave you all over. So nice to have someone get to those hard to reach places. Your stiff cock would be firmly in my grasp as I carefully shaved your penis and nutsack. ... Read full Story
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First Date With Daddy
My Dream Date. It hasn't happened yet, but a girl can hope, this story is very short story based on my fantasy's. It was Sunday night and I had my first date lined up with daddy. We hadn't met, but we had spoken online at depth and exchanged numbers. I had sent him a couple of pic... Read full Story
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To a date with Storm
Her figure shadowed by no dimming light as she drags all lovers alike from where little did they know they were at comfort before from. In her fiery beauty I know I would burst into flames like punk dry timbers at first glance and incinerate upon touch. My brotherly advice I was given when once ... Read full Story
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First Date
"Hey babe, the movie has been over for an hour. I really should be going," Joe said as he stretched, letting out a yawn. "Thank you for dinner, that was wonderful." "Hmm? You don't have to go, you know. You could hold me tonight while we sleep." I yawned a little. I ... Read full Story
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Some first date, huh
So I had just gotten this new job at a fast food/dine in kind of place for the summer trying to make some extra money before the fall semester started. And there was this boy named Danny that would come into the restaurant every so often. He was really cute and had nice lean looking body. He was pre... 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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My first date with a "shemale"
I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... Read full Story
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My ideal first time
We talk online for long enough to build trust. He is aggressively letting me know how much he wants to fuck me. His size is bigger than 6. He is physically larger than me and slightly older. After cumming to and on my pics several times over the course of weeks or months, we finally decide to meet. ... Read full Story
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Party Surprise - First sex as a Crossdresser
This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly s... Read full Story
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First time
I was the only boy in my family. Tall, slender, and somewhat effeminate. Many said I looked like my mother, who I adored. As a youngster, I longed to dress like my sisters, who wore such pretty things. One day, when I was alone, I snuck into my sister's room and admired all of her pretty things. On ... Read full Story
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MY FIRST SEX WITH SHEMALE
This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous durin... Read full Story
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Make that Date
Below is a transcript of a recent episode of a new made for TV series called 'Make that Date'. Chuck: "Hi, everyone, this is Chuck Woolery, and welcome to another episode of . . ." "Make that Date," the audience screams in unison. Chuck: "I would like everyone to pu... Read full Story
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Junior's Department
Junior’s Department The long-haired young male browsing alone in the ladies’ junior’s department caught his eye and he stopped walking to the store exit. He stepped behind a display rack across the aisle, then watched him approach a mirror and scan the area before holding the skirt and blouse up ... Read full Story
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Blind Date
XtinaSmith2017 Anthony awoke to a piercing buzzing tune, a nice enough melody, but one he had come to despise shortly after he had made the mistake of making it his alarm. The culprit, his smart phone, was plugged in on the nightstand beside him and was in the process of making him gleefully aw... Read full Story
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Catching up, last evening, a date at last
After I moved to France I was too busy to do anything about finding somebody to have fun with – just life getting in the way. I had a date with a post-op ts woman when I went back to the UK in 2008 but since then, no dates. Last year I decided to do something about it so went online and found ... Read full Story
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A Mate's Trans Date
I had been seeing Nikki for about 6months and taking her out as you would any girlfriend, sharing our groups of friends socially of course. One evening we went to a friends place and when Nikki has snoozed off to sleep on the sofa me and my mate called Al got talking, we had been drinking most of th... Read full Story
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First Time
I'll start with a description. I'm 46 years old 6' tall and fairly thin. Oh and I'm a cross-dresser that when dressed goes by Lisa. I have been for years. Don't know why other than it pleases me. I love the feel of stockings and garters and for a few years now have gotten to where I enjoy having a n... Read full Story
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First Time With a Shemale
I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we... Read full Story
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Blame Abba Chapter 3
Part 7 First date I do like making entrances, that was one of the best. I didn't wait for anybody's reaction, I just strode across the bar as easily as my tight skirt would allow. I didn't see Patrick at first, but Jeff was there, and he was looking at me. I had assumed none of my mates would be ... Read full Story
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First time Crossdressing
I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards that allow members profiles and posting messages. I also post to local groups in my area that allows one to post messages to a small geographical area or to a distant user g... Read full Story
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Perfect First Date
i would make dinner for us at my house and we would relax get to know each other better and wed eventually end up sucking each other till ever ounce of fluid in ur bodies was drained, intertwined your cock deep in my throut,as i slowly work my tongue around your cock, you begin to breath harder and ... Read full Story
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My first cock experience
I will never forget my first experience with another cock , it was the only time I have ever been with another man, now saying that I do date ts women, I love them as much if not more then I do genetic women. I was 12 years old and like any young boy , very horny . At that time my best friend liam a... Read full Story
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My First Sex with Tgirl
This is story about me......Hope you all enjoy it I was 19 years old and itching to have sex like every normal teenager. Years of jerking off to porn had only expanded my imagination and made me want to fuck a girl even more. I was turned on by just about anything and everything except gay porn. Ev... Read full Story
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My first encounter
I started dressing in my s****r's clothes when I was about 11, she would have been around 13 then. It was wonderful, just Mother, s****r and me at home so when I got a little older, I promoted myself to Mother's clothes. She was a real fashionista back in the 1950s to 1970s, always very elegant and ... Read full Story
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First time with a Tranny
My first tranny I had was back after I graduated from high school. I was working with her/him at a Wal-Mart store. We got along pretty good then we started to date, I was living on my own so we usually go to my apartment. I had no clue she had a cock, she was a very beautiful woman with size B tits.... Read full Story
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My First Tranny
I met Charkara (her real name) through an adult dating site. You can find her pictures on my xhamster page titled, "My First Tranny". We corresponded through the dating site quite regularly before we decided to take it to next level and exchange phone numbers and email addresses. We ... Read full Story
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My First Time Out Part 1
Shayna paced back and forth throughout the entire Suite while she nervously smoked the long thin cigarette. She occasionally stopped and peered into the mirror thinking that all of her hard work had gone to waste for tonight. She was dressed to kill and had no place to go. The red patent platforms w... Read full Story
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Slut bi cross dresser
Party Surprise - First sex as a Crossdresser. This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed ... Read full Story
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My first time as a Femboy CD
My name is Nick aka. Nicole. I am a 20 year old gay femboy crossdresser and this is a little story of how I started dressing to become Nicole and my first sexual experience besides masturbation. I grew up living in an apartment complex with my mother and sister, who was 2 years older than me. M... Read full Story
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My First "Real TS Encounter"
September 2007 Alright, so I’m going to put into writing the story of my very first “Real TS Encounter.” This was back in 2007, so I’m going to do my best to remember as much detail as possible. However it’s been nearly a decade, so we’ll see how it goes. I had be watching “Shemale” porn for a... Read full Story
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First Time Fantasy
We talk online for long enough to build trust. He is aggressively letting me know how much he wants to fuck me. He is physically larger than me and slightly older. After cumming to and on my pics and videos several times over the course of weeks or months, we finally decide to meet. He may or may no... Read full Story
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A true first time.
I want to preface this reiterating that this is a real story about my first ever experience with a shemale. It's a memory I will hold forever as it was everything I could have hoped for and, as I may share in the future, lead to other experiences, too. A little history of before the first meet ac... Read full Story
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TV Times
One evening I was online when someone wanted to start a chat with me. It was a bi guy who enjoyed cross dressing and having viewed his online profile I said "Hi" and we got to talking. He was married guy named Mike and he had a very understanding wife who allowed him to meet men and a... Read full Story
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First black T-girl
I've been wondering what to write about lately. I've received a request to write about me and my sister, but that is a road I might have trouble going down. Today I was thinking about my bi-sexual stripper girlfriend from the past, who loved bringing home other strippers (mostly lesbians) for some h... Read full Story
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Shemale First Time
First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married... Read full Story
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A Lady's First Time
When he'd first stepped into the bathroom, it had been Daniel who had stared back at him in the mirror. Now, the face that smiled back was almost complete, and Cassie was nearly ready to go. First had come all the undergarments -- the satin panties that felt oh so right, then the bra that had giv... Read full Story
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My first shemale sex
I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our ... Read full Story
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My first shemale sex
I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our ... Read full Story
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MY FIRST SEX WITH SHEMALE
This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous durin... Read full Story
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First Time Fantasy
I'd never had a real experience before. Years of wearing panties and fantasizing, but nothing legitimate. I imagine it's the same story as many other panty lovers: started when I was about 13 by stealing some of my mom's things. Bras at first, then panties. Soon I began looking forward to being home... Read full Story
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Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
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tiffanylondontv becomes a captive slave prisoner and whored out
I had connected with Master X on a BDSM Fetish contact site. He was the owner of a fetish store and he said that he had been on the BDSM for several years. He had carefully studied my own profile and had seen that I had an immense interest in being used like a slut, being covered head to toe in... Read full Story
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P.A. for a Day
The gates swung closed behind Charles as he slowly drove his car up the sweeping driveway. Even though he was looking forward to the erotic delights which were in store for him that day, the cares of the world seemed to weigh heavily on his shoulders. As he drove up to the garage he mused about t... 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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DATES NUITS
My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... Read full Story
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Becoming Her Whore
"I know," my wife Casey said softly as her hands caressed my naked body beneath the covers of our king sized bed. "You know what?" I asked. I didn't know what game we were playing but I was ready to fuck. "I know what you look at on the computer and what you fantasize ... Read full Story
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Betrayed Chapter 4
I really wasn't surprised when Dianna directed me into the parking lot at Ringers. It was only a few blocks across town from my new home; a five-minute drive, if the traffic wasn't killing at the time. Consciously, it had not been a factor in my decision to take the new place. Sub-consciously... wel... Read full Story
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I meet my new Mistress for the first time
I was feeling excited about and looking forward to Friday night. The reason for this was that I intended to dress up as my alter ego, Tania Harvey, and to go for a night out to a club nearby that is popular with TG’s, TV’s and other like minded people. I took a lot of care and attention over the way... 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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My Dream Cums True
Me and my girlfriend would always talk for hours about our secrets and feelings and as the night would progress we would get into more sexual subjects but this night would change our lives forever..... ''so what's a sexy secret you have that no one else knows about?'' I asked my girlfriend. ''... Read full Story
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Date With A Mistress Part 2
The week went rather slow for Patrick and he was anticipating Friday night. He didn’t know what would happen as he picked up the phone. He dialed the number with trembling hands. When the phone rang the person on the other end told him to call back in an hour as the Mistress wasn’t at ho... Read full Story
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Darling Nikki
Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She ... Read full Story
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Deep trouble
I'm at a bar, it must've been a weeknight because it was sparsely crowded. I'm having a few drinks (more than a few but), there is music playing, people are kinda dancing. This beautiful blonde about maybe 5'7'' comes in all alone. Sexy little thing with big dick sucking lips, huge breasts squashed ... 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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Teasing BIG BLACK COCKS at truck stops
I'm a white blonde bubble butt Tgirl living in Las Vegas and sometimes I go out and cruise the truck stops on I15 down south to I10. I do it at night and sometimes for a whole weekend in my mini van which has darkened windows. I love to get out of my mini van and walk around the back parking row at ... Read full Story
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The Perversion of Bev - Part 1: The Beginning
“Some fucking romantic weekend this is turning out to be” thought Bev as she sat alone in the hotel room. Phil had told her he’d booked something special to celebrate their Silver Wedding anniversary and she’d been so looking forward to a weekend away without the kids. The fi... Read full Story