Shemales Porn Stories
Page 57

Caught by a neighbour

I started crossdressing at quite an early age, 'borrowing' items of my mum's underwear and furtively dressing in them when she was at work. As I was an only c***d, and mum and dad had separated, I had quite a lot of time to indulge my little hobby! I used to love wearing her tights, the sexy feel of them encasing my legs and cock, and the way they made me feel so girly when I admired my reflection in the long mirror in our hallway. I would also wear her big full-cut knickers and doreen bra, and complete this with a lace slip and a pair of strappy heels or mule slippers that I could fit into th... Continue»
Posted by sparkyking 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Vicky's Pink Diary 01

There he is sat on my bed, my Uncle, Uncle Creep, well that's what I call him. I'm just staring in shock as he flicks through it.

"Put that down, it's private," I manage to blurt out.

"Don't worry, you poor little thing. I've read it right through a few times. I won't tell anyone, Vicky, isn't it?"

I'm shaking in horror, my diary, my pink diary with all my secret thoughts and wishes, my fantasies, and things I've done, embarrassing things. Well how many 18 year old boys get a kick out of wearing their and their stepmother's underwear and dresses? How many boys write things like tha... Continue»
Posted by sparkyking 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  
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A night to remember with G/F and a sweet little tr

At 52 years old i have had a extensive sex life. I have always been impressed by and i will use several words to describe Shemales, trans, Gurl, Traps, cross-dressers. I guess I like the fact that they take some time to look and or change into a better person and going from male to female can take some time and tricks.

Boston MA 1997: My G/F and I decided to add some spice to out very adventurous sex life. We went out one night to a alternative club that had a fashion show. Most will call it a drag show, this was a little slice of heaven for her. She played with my cock through my pants as ... Continue»
Posted by wankingamerica 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Slutty Sissy Used in a Cheap Motel Part 2

After being fucked and bred by the first 2 strangers and watching my sissy hypnosis videos I was definitely ready for at least one more deep fucking. It was around 10 p.m. when the next guy knocked on my door. I opened the door to find a very large black man about 6'8" and a smaller black man who was about 6 feet even. I invited them both in and was very excited that I was going to be tag teamed by 2 black cocks. These two guys were very demanding and knew exactly what they wanted. I knew that I would do whatever they told me to do, because every ounce of my male thought process was gone and m... Continue»
Posted by cumslutchloe 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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Lyn In Chains

Woman In Chains

You better love loving and you better behave
You better love loving and you better behave
Woman in Chains
Woman in Chains



FAQ - Yes I know this bears a bit of a resemblance to Anais Nin's The Story Of O, and that
is probably where Paul (and Nicole) got the idea. This is my account of what happened to me,
it did not just take place happenstance, obviously, but it IS absolutely true.




I'm a bit you know.... strange. If I have to do something I ostensibly don't want to,
like - you know - smear tests and the like, it turns me on so much I tremble. I had
... Continue»
Posted by lyn_hornygirl 1 year ago  |  Categories: BDSM, Group Sex, Shemales  |  
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Holloween with a surprise

I read this story on literotica and just had to share it with my Xhamster friends.
Here goes.

Halloween my favorite holiday of the season. If you think a twenty five year old does not like going to costume parties, you've' got no idea what goes on in my life. Everyone I hang out with likes to enjoy themselves to the best of their advantage, and Halloween is one of the best ways we can accomplish that. This year, like the last four years in a row, I was hosting a Halloween party at my apartment with a number of friends coming over and naturally, it was a costume party. There was Jessie who... Continue»
Posted by miguym4m 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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My first CD Mistress

It was quite a few years ago, I was so horny that time all I could think about was sex... and cock. I was desperately looking for some fun. I was in a chat room for shemales and crossdressers and ended up talking to Lisa, it turned out we weren't that far away from each other, just 40 mins. We talked over an hour, she asked me what I would like to do if we met... I told her I want to meet with someone who will take control and use me like his slut, she liked that and started asking more questions, asking what I am willing to do for her if we meet, I am willing to do anything for you I said exc... Continue»
Posted by niki_cd 1 year ago  |  Categories: Gay Male, Shemales  |  
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Mistress Cunt's two fairies



Mistress Cunt's two fairies

By Taffy, the little sissy fairy girl



My, my what a wonderfully gay time Angela and I had with our slut friend Lauren and her Mistress Cunt! Here’s a little story about that faggy time and how fairy we were for her.

The weekend started the night before with Angela and I at the hotel; I had already properly dressed in my sexiest outfit, a gold sequin mini skirt with black fish net stockings. It did not take Angela long to get herself prepared and we sat to chat. Chat turned to feel, feel to kissing. It wasn’t long before my panties were down and the... Continue»
Posted by Tigerpaw46 1 year ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Bi Curious Escapades Pt. 2

If you haven't read Pt. 1 yet, you may want to do so.

After my encounter with Chuck, I turned to Craigslist again and got several responses to my post.

First, I will tell you about Norman. He is old, rich, and married and has a wife that he hides his attraction for men from. When I got to his large house, I noticed the brand new Mercedes in the driveway.

I enjoy small cocks, and I knew that this car was a sure sign his was. This would be my first time with a much older gentleman.

He wanted to sit and chat first. Once we felt comfortable he invited me to kiss him. I ... Continue»
Posted by cumquarts 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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Mom Transforms Son into a Transsexual. Part 2


Mae and me were laying in bed cuddling when our Mothers walk in and informed us we had a doctor appointment Mae and I exchanged looks and went into the shower Willa came in the Bathroom and told us to shave each other's body.

We finished as told and dressed each other in our best prissy outfit and walked down stairs we quickly left, jumped into Moms Caddilac we drove for about a half hour then pulled up to a Medical Building. Me and Mae waited in a room while our Moms Talked to a doctor, 90 minutes later a Nurse marched us into The doctors office. The sign read Dr. Goldstien Our mothers w... Continue»
Posted by sissytimmy 1 year ago  |  Categories: Interracial Sex, Shemales, Taboo  |  
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Just a friendly chat. A very HOT, friendly chat

With his permission, http://xhamster.com/user/sevrynxxx and I have decided to share this little chat we had with everyone. I hope you all enjoy. We certainly did:)


sevrynxxx -*licks Michelle on the back of her neck*

MichelleRoxx *Sighing slightly, closing my eyes...*
sevrynxxx - *lightly traces circles with my fingertips on her belly while nibbling on her left ear* *Whispers in her ear*, "I want to take you in front of my fireplace"

MichelleRoxx -I take your hand that's on my belly and put in my slip. Together with mine.

sevrynxxx- Mmmm:) Youre nice and hard:) That pretty little... Continue»
Posted by MichelleRoxx 1 year ago  |  Categories: Anal, Shemales  |  
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University Fun 2

The following night Pete and I both told our friends we needed to study so would be staying in.
Pete gave me a white bra, French knickers, suspenders and white silk stockings, He wore the black outfit I had first seen him in.

As we dressed in front of each other our cocks stood erect and struggled into our panties.

I walked over to Pete and held his lovely hard cock and began stroking him. He moaned as I built my rhythm after a few minutes I felt him tense and a warm sticky mess began to ooze into my hand. I looked him in the eye as I lifted my hand to my mouth and for the first time ta... Continue»
Posted by webbyhose 1 year ago  |  Categories: Gay Male, Shemales  |  
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CD Slut Wife Role Play continued from before ....C


MR x i want you to wait for me in doggy position,than i'm comming and slide my hard cock sooo deep in your asshole that you scream like crazy and your cock becomes rock hard and you can feel my hard cock slide dpep in your stomach while my balls massage your balls in that position...mmmmmmmm i want you in my bed every night with my hard cock sticked in your asshole....

freakyerica mmmmmmmmmm yes baby please fuck me good and hard make my clitty drip with pre cum as to ram my pussy deep and slap my ass tell me i am a good little slut and how you love to fuck my pussy

IN response MrX sent... Continue»
Posted by freakyerica 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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Raised as a gurl

“Here, Slut Puppy! Here, girl!” Gina called from the living room, and I dutifully crawled in from the bathroom where I had just finished using the litter box. My little cockette dangled between my legs, the lock on my chastity cage clicking and the little bell on the end of it tinkling with each sway of my hips. My breasts hung down and swayed slightly as well. Gina liked me to crawl when I was being her Slut Puppy. She liked the collar around my neck and the little tail attached above the butt plug harness that kept a large bulb firmly in my boi-pussy. It was all part of this particular form ... Continue»
Posted by scatpetsmaster 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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Mom Transforms Son into a Transsexual.


I'm a very sensitive white teenage boy who's always been close to my Mother,but my Dad looked upon me with disgust calling me fairy,sissy,faggot, and other choice words, Father was a Marine he is six feet seven inches tall, black hair, Blue eyes, and a Alcoholic. My Mommy is six feet three inches tall, 42DD 28 44 inch frame, long red tresses that flowed over her Boobies and she like to show them off. My parents divorced two years ago he drifted off into alcoholism some place, I was watching porn on Moms computer checking out Shemale and Cross dressing web sites when all of a sudden I heard... Continue»
Posted by sissytimmy 1 year ago  |  Categories: Interracial Sex, Shemales, Taboo  |  
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SUBMISSIVE STOCKING FEMME

WEDNESDAY WAS OUR FIRST MEETING IN MONTHS, STACIE HAD SUGGESTED WE GET A MOTEL ROOM, SO I FOUND A CHEAP MOTEL IN SOUTH JERSEY...I ARRIVED AND GOT A ROOM...THEN I WAITED FOR HER ARRIVAL...



I HEARD A CAR PULL UP OUTSIDE AND SAW A WHITE CAR PARKED...IT TOOK SOME TIME BUT I SAW IT WAS HER AS SHE STEPPED UP...SHE LOOKED HOT...WEARING TIGHT JEANS AND SPIKED HIGH HEELS...HER SLIM BODY SEEMED TO MELT INTO HER JEANS...AS SHE WALKED TO ME ON THE SECONF FLOOR WE SMILED AND KISSED BEFORE WALKING INTO OUR ROOM...INSIDE WE ONCE AGAIN KISSED AND MADE SMALL TALK...
I SHOWED HER THE PANTYHOSE AND SE... Continue»
Posted by blkice2u 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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SUBMISSIVE PANTYHOSE FEMME BMW

WEDNESDAY WAS OUR FIRST MEETING IN MONTHS, STACIE HAD SUGGESTED WE GET A MOTEL ROOM, SO I FOUND A CHEAP MOTEL IN SOUTH JERSEY...I ARRIVED AND GOT A ROOM...THEN I WAITED FOR HER ARRIVAL...



I HEARD A CAR PULL UP OUTSIDE AND SAW A WHITE CAR PARKED...IT TOOK SOME TIME BUT I SAW IT WAS HER AS SHE STEPPED UP...SHE LOOKED HOT...WEARING TIGHT JEANS AND SPIKED HIGH HEELS...HER SLIM BODY SEEMED TO MELT INTO HER JEANS...AS SHE WALKED TO ME ON THE SECONF FLOOR WE SMILED AND KISSED BEFORE WALKING INTO OUR ROOM...INSIDE WE ONCE AGAIN KISSED AND MADE SMALL TALK...
I SHOWED HER THE PANTYHOSE AND SE... Continue»
Posted by blkice2u 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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The pretty girl with her thumb out

It had been a couple of years since my wife left and I was finally starting to enjoy trips by myself. So that fall I through some stuff in the car and headed out to see things and clear out my mind some.

As I turned at the freeway ramp there was a young woman standing at the side with her thumb out. So I quickly pulled over and, with a smile, she hopped in. As we chatted I learned Chris had recently turned 18 and was using her new status as an adult to head north to see a friend. That worked out great since it was the direction I was already going for my trip.

Chris had long blonde hair ... Continue»
Posted by need2try 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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My fate

Oh dear!

Remember the self-confident, virile, young, up-and-coming business executive, with the trophy wife, you were, or were pretending to be, on your wedding day?

Look at you now!

An emasculated, sissy faggot locked in chastity, made up like a pretty girl, dressed in stockings,and high heels and panties, prostrate and helpless before one of your wife’s lovers, as he pumps your mouth full of his residual cum after he has pumped her to delirium!

You thought, when you true on your first pair of stockings and panties, that it was just an innocent curiosity. You kept doing it, taki... Continue»
Posted by sissyteri 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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University Fun

I was 18 and had was in my first year at University.
I had chosen to go into a hall and to my surprise found I was sharing a room.

My room mate was called Pete. He was a bit taller than me well muscled and very butch. We got on well and had lots in common. We both did alright with the girls and were both enjoying being away from home,

The only thing I missed was being able to slip into some panties and stockings or tights for a nice wank and to fantasise. I had being slipping into my mums panties for 7 years and occasionally stealing my friends mums or s****rs. I had not plucked up cour... Continue»
Posted by webbyhose 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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