Free Stories

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Steve to Stephanie Chapter 1
Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve did not consider himself gay because he really wanted to be female. While having sex, Steve fantasized about being the woman. Since he normally bottomed it was fairly eas... Read full Story
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Pretty Like My Sisters
Of course she was surprised. Who could blame her. Walking in on me like I was, I'm surprised that Sarah, my twenty two year old sister, restrained herself to a simple, "What the hell are you doing, Everett?". Her confusion, and possible anger was completely justified. You see, I was fiftee... Read full Story
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Trained and Tailed
It started like any normal relationship. I had dated my owner for several weeks now. He was not my owner yet, at the time he was just my boy friend. He was older than me, I was only twenty four and he was in his forties. A bit older than I had ever dated before, but he seemed nice and I didn't have ... Read full Story
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Crossdressed feeling sexy and horny
I love transforming myself into a woman. I love applying my make up, putting on false lashes, hair piece, padding my bra out, tucking my cock away in my knickers, putting my dress on and slipping my feet into my 6inch heels.I was strutting around my apartment swinging my his like a cat walk model, d... Read full Story
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Punished for Cheating
How my life had changed in the two months since I had taken in Caroline as my lodger. The arrangement seemed ideal at first – I was a newly divorced male and she was a single girl. Of course, I should have foreseen that the 30 year age gap might present a problem but that is the wonder of hind... Read full Story
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I Missed Myself
As soon as Dr. Griffin returned to the examination room, I knew that the news wasn’t good. I could tell by the way he avoided my eyes as he studied his clipboard and fidgeted with his pen that something was wrong, terribly wrong with me. The ache in my groin that I had been ignori... Read full Story
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Having Fun With Reluctant CD
I was at the office and I guess I must have been a little quiet because I scared my coworker, David in the next cubicle to death, almost. Sometimes I take off my shoes and work in my socks and when I stood behind him and cleared my throat, I wasn't sure if he was going to hit me, shout, sit dumbfoun... Read full Story
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Crossdresser 1st time!
Hi, im new to this. this happened about 3 years ago now. I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from th... Read full Story
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Such a whore
I finnaly made this happen a few days ago ! i have been crossdressing for as long as i can remember.I still remember when i snathed a pair of my cousins panties when i was young i dont know theres is just something about womens clothes that just intrigies me . Any way growing up i always masterbate... Read full Story
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Fitting Room Fantasy
Being a 'girl of a certain kind', I always use the women's fitting rooms in stores when I am out trying and buying clothes. I tend to avoid the 'communal' type, where we are all stripping off together, as I'm quite shy and you also never know if someone may pick up on the fact that not everything ab... Read full Story
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Sissy Ghetto bitch part 1
-The Guys 4 ghetto guys was inside a porn site looking at random sissy babe pictures when they accidently found a picture of someone they know. Like every album they clicked it that specific one with a tranny dressed so girly with mouth open. The guys had such a stone hard erection by watching al... Read full Story
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My Neighbor and I first time!
Recently I had a college student move into the apartment next to mine. He was small, shaggy blonde hair, without any facial hair, looks like ever. Skinny with little muscle tone. We started talking while he was taking a break. I told him the normal neighborly bs. Then I went on about my day. Seen hi... Read full Story
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Continuing adventures with a TV
Danni and I met up again this past weekend and again, "she" literally rocked my entire fucking world. Coming in wearing a tight jean skirt, a loose black top and heels. Knowing what we already wanted and needed, she hardly got in the door and we were all over each other, kissing passionate... Read full Story
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Roadtrip - Part One
My vacations started in five minutes, and I couldn't wait to get out of the office. I had been counting the days impatiently for 2 weeks. Unfortunately, I had made no plans but that was ok, I was going to sl**p late for days! A last minute customer call and I was walking down the hall and out the do... Read full Story
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My fantasy of losing my ass virginity
Before I start let me tell you that I am extremely closeted and I love to dress up in women's clothes. I love feeling girly down to the last detail, starting with a complete shave down, then make-up, fake nails, a wig, and of course the sexiest and most slutty clothes and shoes. Most of the time I a... Read full Story
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Allison the pool slut part 1
Allison had now had her fair share of whore experience. The teen boyslut had fallen in love with big cocks, anal creampies, facials, swallowing, and the rest of the nasty fun she had while becoming a sissy whore for her black neighbor and his dark dicked friends. Little did she know she was going to... Read full Story
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Crossdressers first time with a guy
Hi, im new to this. this happened about 3 years ago now. I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from th... Read full Story
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Bookstore sissy slut
My name is dollie I love to be a girl and being very petite and pretty long black haired its easy for me too feminize. And until now I wouldn't go out, dressed up, sometimes a quick walk around or a short drive but nothing real. And one time in college I walked around the campus. Anyway I ignored al... Read full Story
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Crossdressed cocks
I was looking forward to the fun I could have in my own place. I spent some time on the male chat line looking for someone to play with. he to liked to dress but like me was not at all passable . when he showed up at my place he hade on black thigh highs open toe heels and a corset ,he was taller th... Read full Story
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Sissy schoolgirl and her black daddy
I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning... It was summer time. As always I spent m... Read full Story
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My black lover
After one year as a sissy whore and secret wife to my turkish Pascha, I felt the desire to look for a black man. I looked for ads online and put ads online myself. One day I saw an ad from a young black man looking for a crossdresser and wrote him an email. I actually thought I would never hear from... Read full Story
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Me dressed as a Gurl
this happened about 25 years ago when i could half way pass i went to this night club for crossdresser, transexuals and transvestites west of balboa park one thursday night it wasn't has busy has on a friday or week end but there was a nice crowd mustly crossdressers a few trannys it was not to late... Read full Story
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My First Sex Session
I am an Asian crossdresser living part-time. The reason I decided to dress is ever since I was little, I had been getting signals. First at my boarding school when I was fourteen, which is where that experience happened. Every Wednesday night was devoted to activities run by your adviser. I had an a... Read full Story
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Finding master
It had been my dream all along to be someone’s sissy slave. To be able to please them time and time again. I met my master in a gay club that had cross dressing night. I was of course dressed in a dress with stocking and stilettos. Master was in leather pants and a tight tee shirt with his mus... Read full Story
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My cossdressing habit
I am now 30yrs old man, I have the habit of dressing in a female dress,enjoy my female appearance, then masturbate finally. It all started, when I was around 6-7yrs, I started wearing panties of my elder without the knowledge of my family members. It all started just like that, there is now reaso... Read full Story
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Me and Sabrina
This story is fictional. I was just another normal kid. I'm just small and effeminate. My name is Nick. Im 13 years old. I have always enjoyed dressing in woman's clothing. I have a friend her name is Sabrina. Shes a very hot girl. I thinks she 5'5,110 lbs and 36c. Compared to me I'm 5'4 and 10... Read full Story
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Devil with a blue dress
I had the whole day alone and so I decided to get dressed to the nines. After a fragrant bubble bath with body oils I began by painting my nails a pretty pinkish red and putting on my sexy little silver anket. Next my favorite black satin garter belt and a brand new pair of very sheer off-black stoc... Read full Story
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The Training of Julie
The story of the successul aiteration of a good looking youn man into a stunning, talented, ultra feminine boy/girl John was about to learn obedience in the strietbatt sense of the word. his whole life style was about to be changed, The rather alightly built, pretty boy of 17 was to become Julie,... Read full Story
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My brother caught me crossdressing
It all happened 3and a half years ago.I started secretly crossdressing about an half a year before.One day my parents went out and told me that they will be late,and my b*****r was staying at his friends house (he was 17 back there and i was 14).As soon as they left the house i ran down to my mom's ... Read full Story
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How i became a sissy/my first blowjob
I'm a 17 year old sissy now but i started crossdressing 4 years ago when i was 13 :).This is the story. One day my parents went to our lake house for the weekend with my s****r but i was feeling sick so they left me with my grandparents. They were taking care of me for a day or two and i got better ... Read full Story
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Young sissy goes for a little shopping... caught
May be first a little introduction? My name is Sylvia and I love women's clothes! I like panties, stockings but most of all, I adore high heels! just love them! That feeling when it becomes higher and I feel so sexy and feminine! And you know what? I'm a total slut, I love to be humiliated,... Read full Story
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Gina Thank You Surprise
I get pretty excited when my company sends me to Cincinnati for the week. I think my wife can sense something and I have been getting a little nervous she might be catching on. Over the last year I have made the trip seven times and on the first trip I met up with Gina a nice 35 year old CD I friend... 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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Loaning me out to strangers
My wife and her friend Tina were going shopping in Kansas City for the week end. I knew this meant that I would be with Phillip. Tina's husband and the man I can't stay away from his cock. This meant I would be dressing up like a slut and servicing Phillips cock the whole time our wives were in KC. ... 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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Daddy Girlyboy
I was alone in the house so I was indulging in my fantasy of dressing up as a girl. I had my long hair all straightened, full make up and my skimpy sheer black thong on with black stockings and suspenders with a tight lycra dress which showed off my very girlish figure. This was finished off with a ... Read full Story
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My First Time as a Girl
I was hoping to hook up with a straight guy. I have 2 b*****rs and a s****r I’m the youngest and a Freshman in high school. Always been fem preferred to play with my s****r and her dolls. My dad is an ex-marine. Tough guy. My b*****rs are following in dad’s footsteps, military orientated. I‘m a b... Read full Story
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Slave in Training
There's never anyone that I'm interested in at my school. None of the guys here are hot, and I don't even want to deal with them anyway. That's why I began going out and looking for older guys, ones that know what they're doing. Since I just turned eighteen, that meant that ... Read full Story
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Oh The Joy!
As I removed my trousers my mind started to think about the naughty things I could get up to very soon. What possible delights that may await me today. With my male clothes now in a pile on the floor, I stand there naked with a completely hairless body, the recent full body wax worth all the pain I ... Read full Story
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Good Friends are the Best
This story takes place after I had been crossdressing and watching shemale porn for years. It all started out with me trying to avoid seeing men's cocks while watching porn so I tried lesbian porn and then found shemale fucking girls porn to be crazy sexy. After watching a lot of shemales fuck... Read full Story
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Fucking A Cute Asian CD
I've always wanted to fuck a cute young tranny. I love their femininity - those gorgeous gurl bodies and the way they are into the lifestyle. Such a turn-on. I pulled my cock out of my boy Kevin the other night and the two of us collapsed in a heap, satisfied with what we'd just done. As we lay in... Read full Story
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Alaska adventure
I was stuck in my parents apartment, living with them and working at a bar downtown for the summer. I got bored hanging out alone in my room,. so I snapped a few pics and put an ad in the TV/cd section on craigslist. I waited a bit and it wasn't long before someone replied. Then a few dozen ... Read full Story
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Fucking CD
So it had been a while since I went to my favorite hot spot in Atlanta. I knew that whe I decided to make the drive it was gonna be a hot day, I actually wasn't looking for anything in paticular that cool day I just wanted to cruise and flirt a little. As I started walking around I noticed that... Read full Story
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I am a sissy maid
Part 1 Around the end of my last high school year, my curiosity for crossdressing had just emerged, but I didn’t explore the fantasies too much as I thought it was just a phase. The following fantasy is something I have dreamed about for years… A friend of mine, Peter, was into the same video ... Read full Story
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End of a great thing
So in an earlier story I told all of you about I guy I literally ran into when I was trying on lingerie and it turned into my first sexually with a man. So we had a great time for several months. One night he called me over and we had our usual sexual adventure. After we were done he told me tha... Read full Story
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CD Jinn New Adventure
So my last story "college experience" was about one of my three roommates finding out I was a cross dresser along with his girlfriend. His girlfriend Stacy encouraged him to dominate me and display power over me. I think that is really what she enjoys seeing. While he was slipping his cock... Read full Story
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Oh The Joy! Part II (revised)
Oh The Joy! - PART II I returned to the cubicle to get some wipes and clean myself up. Touching up my make-up I ran through in my head what had happened and I smiled inwardly. What else may lay ahead for the rest of the day? After what had been done to me earlier would be hard to beat, that’s for s... Read full Story
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CD Jinn Caught
Lately I have been having great times with one of my roommates who found me out and found he really enjoyed being with me when I am dressed. However before any of this happened I had met a guy through a friend on the football team at my college and had a couple great times with him while I was dres... Read full Story
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Crossdresser Lovemaking
Oh Daddy, I'm your little princess! Your wife is out taking your kids to a sleep-over at a friend's house across town and we're in your bedroom. I long for you to see me with bursting lust, and I take off my coat to reveal myself wearing a white tutu with bra, panties, stockings and h... Read full Story
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First Hotel Encounter
we met online and agreed to meet at a hotel. I was so nervous but excited to explore this very wrong side of sexuality. At the front desk, you had your arms around me kissing me deeply as you pushed up my skirt so the clerk could see my pink panty covered rear as he flashed you the "way to go p... Read full Story
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New Black Friends
I go to a small discount store near my house once a week to buy candy. One sales clerk is obviously gay. He is nice to me and we have short conversations when I pay. He is a tall skinny black guy 22 years old and his roommate is short and pudgy. Over the past few months I have often thought to just... Read full Story
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Turned into a slut
I had been kind of seeing this really cool CD for a month or so. It was very casual, I would see her in certain clubs and we would hook up and have a great time but I don't think either of us wanted anything particularly serious. Whenever I saw her she would always look really smart and had a r... Read full Story
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My Date with a Crossdresser
A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity. We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready ye... Read full Story
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First time dressing up
I was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my s****rs clothes. I went into my s****rs room when the house was empty and opened up her closet. I saw... Read full Story
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Cross Dresser Fucked Like A Whore By Black Cocks
My name is Ryan and I turned eighteen years old a week and a half ago. I live with my mom and s****r in an apartment in a pretty nice part of town. My dad left when I was little and I know that living with two girls had the effect on me that it has. A couple years ago when my mom and s****r were at ... Read full Story
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White Sissies on Black Dicks
Sunni inhaled the marijuana, held it in for a few moments, and then released a puff of smoke in the air. The effeminate white man with a platinum blonde Mohawk pressed the number two button on his phone to listen to the message. He heard a deep-voiced Black man say he needed his dick sucked and woul... Read full Story