Shemales Porn Stories
Page 64

crossdresser ashley[this my story]

hi my name is ashley,I'm 48,and have been crossdrssing since I was 14.its about the time I discover masturbation.when ever I would take a bath or a shower I would take out of the hamper my s****r panties and bra sit the and stroke my cock thru the material.often I'd find a pair of pantyhose,and would slip them on.felt so hot wearing them,I even wore them to school.lot times if no one was home I would sneek down to our shop that we had out back where you could not see it.inside I would strech out on the table and rub my cock getting it nice and hard sticking a finger in my ass,it felt strange,b... Continue»
Posted by blonde68 1 year ago  |  Categories: Shemales  |  Views: 960  |  
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The Developing of Emma part Six

As the weeks went by, Emma was subjected to many rituals before a crowd of masked leering males. Each day she was kept caged and plugged; her dosage of pills never forgotten. Each day Emma felt more and more feminine; one morning Elaine had her stripped naked except for cage and plug, and led her before a full length mirror. Emma now understood more than ever just why she felt the way she did.

Elaine smiled victoriously as the sissy saw with her own eyes just why she had almost forgotten she was ever a male; her hair had grown rapidly and a just a little make up from the maids, had her l... Continue»
Posted by midsummerman 1 year ago  |  Categories: BDSM, First Time, Shemales  |  Views: 949  |  
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After My First Tatse of a Dick

After I got over the heart pounding of actually touching another man's cock and then putting it into my mouth, I wanted to leard how to be a good cock sucker. My first cock sucking was in 1979 in Charlotte NC in an adult book store. Back then there was only books and I also wanted to be exposed in them too. I made up my mind that I would do everything necessary to learn cock sucking and being sexy for TV/CD mag.

The first dick I sucked was somewhat a disappointment. The man was probably also somewhat worried about being in a booth with a made up sissy so he did not really cum with a large l... Continue»
Posted by sandyjcd 1 year ago  |  Categories: Mature, Shemales  |  Views: 1657  |  
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The Developing of Emma Part Five

As Kurt caressed Emma’s sweetly pronounced bottom, she realised she had never felt so feminine before, despite her newly freed cock standing stiff in nervous anticipation. She looked at the powerful male and the leering male audience; the few females there would now witness her being used as a woman. Kurt’s large stiff cock rubbed against her belly as he moved her round to a large and convenient futon, stroking her soft and slender hairless arms as he savoured the sweetness of her. He had her kneel in the middle of the futon, and then pushed her forward, the soft fabric seemed to engulf her,... Continue»
Posted by midsummerman 1 year ago  |  Categories: BDSM, First Time, Shemales  |  Views: 941  |  
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The Slave and the Sissy Part Seven

Honey was viewed like a new toy by her new master’s people as she was led whimpering to the ominous looking padded pole, the males jostled to fondle her soft white bottom and rubbed their erect cocks against her sweet little body at every opportunity; the womenfolk smiled with eager anticipation at the prospect of seeing a whipping; the sissies looked on with blank faces, having tasted the whip before. The males at the front howled with wicked derisory laughter as they viewed Honey’s little cock rising to an erection once more; despite having already spent herself generously twice before toda... Continue»
Posted by midsummerman 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 755  |  
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My First Bukkake

It was shortly after my 14th birthday and I had already discovered (at the tender age of 12) how much fun it was to have sex! Me and my BFF, Ashley, were always finding people to get naked and have fun with and we were ALWAYS together ;-) We quickly learned that we enjoyed wearing stockings and heels, wigs, makeup and sexy outfits, dressing up like whores for men. We quickly learned that we loved sucking cocks and licking balls. We learned that we liked having our blossoming, young bodies provide pleasure for men. But most of all...we learned that we enjoyed making men cum...older men...well-h... Continue»
Posted by cdsexslut 1 year ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 3335  |  
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The Developing of Emma Part Four

Emma awoke in the softness of her silk sheets and wondered what the day would bring; her sissy cock bulged and dribbled sticky pre-cum through the outlet of her cage as she thought of sucking Kurt’s cock; her tight little anus clenched and released at the plug, which acted like a comforter. Elaine was right, Emma was beginning to enjoy the plug and as she tried to rub her confined cock, she imagined the plug to be Kurt’s cock; how she wanted to cum! The blue pill she had been given would keep her little cock hard in the cage and make her yearn to orgasm. This would make her extra obedient a... Continue»
Posted by midsummerman 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 829  |  
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The Developing of Emma part Three

She awoke to the sickly smell of a woman’s perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence.

“Hello again ‘Emma’; that’s a very pretty name you’ve chosen for yourself, we shall soon have you worthy of being Emma, and you’ll soon know your place amongst men, and women.” The woman was sat with her legs crossed in a throne-like chair, no store clothes now, she wore a one-piece black leather bodice which accentuated her mature curves exquisitely, and black seamed panti... Continue»
Posted by midsummerman 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 530  |  
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The Developing of Emma Part Two

The lush feel of the silky panties was overwhelming; even after his spent balls were drained for the fourth time there was no sating his urge to return to the store and that woman who had controlled him so easily. The reflection in the mirror was so ‘Emma’; the vision so strikingly effeminate, enhanced by the luxurious lingerie. Tomorrow could not come soon enough.

It was with little trepidation that he entered the store again the following day; there, this time dressed entirely in black, was the buxom matronly woman, oozing dominance. The figure sent a shiver down his spine as she sneer... Continue»
Posted by midsummerman 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 653  |  
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My Asian fetish

I have a ongoing fetish and desire to dominate and have as my wife a petite asian sub t girl. I meet her online and fly her here and in the car she reaches over and pulls out my stiff cock. She coooes as she strokes my shaft and tells me how it is just the right size and thickness. She sucks me slowly and then slides all the way to my balls as I know i have a skilled lover. At home she changes into white lace lingerie stockings teddy and 6" stilleto heels. She enters the living room and hits her knees and begs to suck my lovely cock. she looks up lovingly into my eyes and tells me she ha... Continue»
Posted by brett40000 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 505  |  
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Trying times

i`d been out all night and had only met a couple of fellas around midnight it was about to get

light soon so i`d better get myself off somewhere a little more suitable
as i`m a bit more tarty than usual... i`d been walks.. across the carrigeway and around the estate

ther i`d ventured a fair bit further than antisipated and found myself lost .
having to make haste i headed straight down the main road towards the A556 which inevitably

took me into the path of other road users afew cars ..acouple of
which ,occupants had shouted get em off !. pipping there horn the others had s... Continue»
Posted by Carla69Brown 1 year ago  |  Categories: Shemales  |  Views: 683  |  
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Michael's Prom Night (A Chrissie Conway Story

Micheal’s Prom Night (A Chrissie Conway Story)


Kelly and I are home for a few days and were staying at Kellys' mom’s house as usual. All week long all her b*****r Michael can ramble
on and on about is the senior prom coming up this Friday night. He and
Two of his buddies decided to pool their money and talked Kelly into renting them a Cadillac for prom.
When any two of them are together all then talk about is how they are
finally going to laid on Friday. They been waiting the entire school year for prom weekend because the popular myth is that even girls who don’t “... Continue»
Posted by chrissieCD 1 year ago  |  Categories: First Time, Shemales  |  Views: 1389  |  
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Chrissie Learns A Harsh Lesson PT 2

Chrissie Learns A Harsh Lesson Part 2

I returned to the small adjoining room as he had instructed me and once again I amazed at the accumulation
of S and M devices. The difference this time was now i was expected to select three different spanking implements
that he intended to subject me to. I suppose I could have just refused and ended this ordeal but a part of me wanted
it to continue.
"You don't have all night to make your selections you know" he bellowed "I am going down to shut the lights out
in the store and I expect you to have made your choices by the time ... Continue»
Posted by chrissieCD 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 436  |  
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Chrissie Learns A Harsh Lesson PT 1

Chrissie's Gets A Harsh Lesson Part 1

This is a story I've been wanting to write for a while but I only recently got the gentleman involved to tell me it
would be okay to write about our encounter. Normally it wouldn't bother me to write about any experience I've had but
this gentleman is a special friend and I didn't feel right about relating the story without his knowledge. As you probably
guessed, with exception of Kelly, I generally change the names, dates, and locations mentioned in my stories. Even though
I won't be using his name or telling you any personal ... Continue»
Posted by chrissieCD 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 818  |  
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Weekend Office Sex

So I am the low man on the scale at work. My job is with the City I work in dispatch and am one of the people responsible for getting road crews, hydro and sewer crews out to fix problems wherever they occur. My boss is a very attractive woman named Jamie. She stands about 152 centimeters and dark chestnut hair that is short at the back but gets long at the front. It matches her deep espresso eyes. She dressed very professionally at work ankle length skirts, blouses and blazers that type of thing. She has perky c cup breasts that when she trots or runs through the office they have a nice... Continue»
Posted by triphammer73 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1867  |  
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The Developing of Emma Part One

From an early age it had always been the same; an attraction to girly things, never quite fitting in with the boys. When adolescence brought out its spots and downy genital hair, it also brought the urge to dress in s****r’s clothes when no-one else was at home. The feeling of a tight bra and panties contrasting with the airy freedom of a thin cotton dress, whilst perched precariously on high heels, always guaranteed a healthy erection followed by most gratifying hand relief. Oh to be a girl! On one of these occasions, as an eager cock erupted whilst viewing dress and heels in the mirror, ‘... Continue»
Posted by midsummerman 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 1765  |  
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Fixing her computer

****d (sort of) by a Shemale!
By johnnyshemalelover


I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon.

I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.

Her hair was dirty blond and loosely curled, and her face w... Continue»
Posted by leadpencil21 1 year ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3297  |  
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Two girl adventure


TWO GIRL ADVENTURE
It was a dark night as I strolled into the main street bar. I was 21, had been having hard luck with the ladies, and was looking to drown my sorrows in a couple brews. That's when I saw her. She was simply a knockout. She was about 5'8", blonde hair, blue eyes, and a smoking body. She was wearing a tight white belly shirt and low hip hugging jeans.
I watched her play pool and talk to people for a few minutes before I decided to make my move. I approached her as she was standing around holding a pool cue and asked if she would like to play me. She agreed and we began play... Continue»
Posted by leadpencil21 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 1660  |  
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my first 3some

at the time I was 21,I was able to get into the clubs,it was saturdaynight which was drag night,and I got all dressed up,wearing a red miniskirt,black top,with a black lace bra,matching garterbelt lace stocking,and panties,and a pair of black6inch high heels.I met this guy name john,who wanted to know my name,as I told him my name is ashley,by the way thats my real name.well john was very interested in taking me back to his place,I lets go.he was 6ft 200lbs,very good looking,with a 10inch cock.he had told me that he had a roomate,that my be there,and quite possble he might want to join in,I us... Continue»
Posted by blonde68 1 year ago  |  Categories: Shemales  |  Views: 1071  |  
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poker night

one night,my ex wife decided to play poker for fun,bout 30 min of playing,we made more interesting,that on the next hand,the loser had to do what ever the winner wants.I lost on purpose,so then she said to take a shower,and shave off all bodyhair,legs,chest,arms,underarms,face.then meet back in the bedroom,where she laid out a very short black minidress,black lace garterbelt matching panties,lace stocking 6inch high heels.then she applyed makeup,painted nails,jewery,and wigI look in the mirror and saw this sexy girl standing there,she had transform me into a beuitifull female.she said now your... Continue»
Posted by blonde68 1 year ago  |  Categories: Shemales  |  Views: 1388  |  
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