Shemales Porn Stories
Page 8

Sissygirls Sweet Adventure

She had spent an eternity with the finishing touches, making herself look as soft and girly as possible, not that she needed to do so. She was as nervous as hell and teetered just a little on the tall black stilettos with silver spikey heels she had waited so long to wear. The walk down the path to the waiting cab seemed three times as long as usual; would the driver think there was anything unusual about the girl who was his latest fare? He smiled warmly and watched the long legs enter his cab.

“Where to Miss?” Sissygirl was wary of speaking for the first time, a little scared that her t... Continue»
Posted by midsummerman 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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my shemale GF part 2

So today she , her name is Christy, she wanted to do something kinky, very kinky I said that's fine. We cleaned up, she went into her closet, which was filled with dildos, butt plugs, sexy clothing, fleshlights, cock rings, paddles, lube, videos, magazines, bdsm things, and a fuck machine. She came out with this red latex suit on, which exposed her tits, ass, and her sexy 7 inch cock, with red boots that went to that hot cock and a cock ring. She ordered me to get on the bed face up, she sat on my face with her big round ass. I licked her ass for about a minute, she then ordered me to get on ... Continue»
Posted by germanface 3 years ago  |  Categories: Anal, BDSM, Shemales  |  
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My Addiction

My addiction
Is the sweet syrup
That drips from your dick
It’s like honey,
And the more I taste
The more I wish I could shoot it in my veins
It’s like my liquid cocaine,
Daily doses required to keep me sane…
And I will be your junkie
Just tell me how you want me
Down on my knees begging baby please,
Just let me taste you.
I would do almost anything
To have that every so sweet nectar
Trickle down the back of my throat
As I drain you dry
Nothing compares to the complete embrace
Or look in your eyes when I am pleasing you
This is all I want to do
Make you my 9 to 5,
But I work... Continue»
Posted by Hangdog90 3 years ago  |  Categories: Fetish, Shemales, Voyeur  |  
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2nd date

So I previously posted a story about my thursday night at the gloryholes at Frenchy's on Polk in San Francisco. I met a gorgeous tranny and we went back to her place for some fun. Well since then we've had lots of fun.

A few days after meeting Bianca I was really wanting a repeat of the fun we had so I gave her a call and she invited me over. It was still kind of early when I got to her place, I was a bit nervous because I didn't know if we could have a repeat of the time before because it was so hot. Well she answered the door dressed in a tiny plaid skirt, white stockings, white shirt w... Continue»
Posted by tat2sf 3 years ago  |  Categories: Fetish, Shemales  |  
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Rebecca

I work at a large restaurant chain in their construction division. I spend my time co-ordinating the construction and remodelling of the stores in our chain. Part of my job includes travelling to locations where restaurants are being built, and ensuring that nothing goes wrong.

I was recently in another town, and on my first night in town I hooked up with Chantal, the woman who worked behind the counter. She was an aspiring architect, and so we discussed the construction industry at length over dinner. After dinner, we went back to my hotel, and after some very hot and heavy foreplay, she p... Continue»
Posted by pau10s 3 years ago  |  Categories: Fetish, Shemales  |  
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Afternoon's Delight


She stood at the folding table in the apartment's laundry room. She saw him across the room, reading a paper, but not really. She could tell from the glances around the paper every now and then that he was checking her out. She smiled to herself. She enjoyed being checked out, especially by an older guy. She stood five feet six inches, and had rich thick brown hair, with some sun bleaching, lightening it. Right now it was up in a pony tail but unpinned would fall to her lovely tan shoulders. She was wearing a halter top, one of her faves. It accented her full 36C breasts besides exp... Continue»
Posted by sliplover 3 years ago  |  Categories: Fetish, Masturbation, Shemales  |  
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Becoming Alanna - Part 2

Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work with is there” she laughed looking at my small cock “but also not much to work with in the way of hair". She applied the preheated wax and then the strips to the areas around my cock and my asshole, the area connecting them and lastly my balls. She gently tugged them off and I cried with pain. “Oh shut up s... Continue»
Posted by KristyQuinn 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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The Football Jock and Chrissie

The Football Jock and Chrissie

Back in college, sharing an apartment with my BFF/roommate Kelly, a lot of my dates and hook-ups were arranged by Kelly. For some reason she always seemed to know just who was into what when it came to sex. She learned a lot about other people’s likes and dislikes from hanging with her lesbian crowd. She was also super inquisitive and fancied herself as somewhat of an amateur detective. I just thought she was nosy.
It was 1998, the middle of our junior year, and I had already been transforming from Christopher to “Chrissie” for 4 ½ years by this time. Needl... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Anal, Shemales  |  
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TRANSLESBIANS [this is a true story ]

When I first got married in 1992,my exwife,and I were getting along well,everything inbetween,ecept for sex,either I was stressed out from work,or somthing else.well one night we were talking in bed,and were dicussing what we wanted to try out in the bedroom.I'd say well blindfolds,and being tied up sounds nice,or even whipcream,and some type of cream dessert,where we would smear over are bodys and lick it off.but then it happen,I told her that I use to dress in drag,she replied what?she new what I was talking about,and went to raing hell.after a few hours of arguing,she finaly calm down,wasn'... Continue»
Posted by blonde68 3 years ago  |  Categories: Shemales  |  
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Alex Two: The Next Time.

Part Two of ??? (there is another series I'll start too, Hopefully its not too
repetitive and my fetishes aren't showing too strongly. heh. That is sort of a
prequel to this, I guess. I had forgotten about it till just now when I found it in a
misnamed folder.)


Alex Two: The Next Time.
By Alex Shouse.

Chapter Three - Hard Work.

I had stayed there for awhile long after he had left. Long enough for my own cum to start drying
where it had spattered. The inside of my mouth felt thick and coated, with a slight acidic aftertaste,
And my jaw was a little stiff from the ... Continue»
Posted by AlexShouse 3 years ago  |  Categories: Shemales  |  
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A Sissies Humiliating Confession

This is a real life situation that happened this past weekend. I am sissy slave jennifer and i am owned by my beautiful Mistress Rita. Mistress Rita loves nothing more than putting this pathetic lil sissy through the most humiliating situations She can get away with. I once confessed to Mistress that when i was 16 i wore my very 1st pair of panties. Mistress insisted that i tell her who's they were, where i got them, and how i got them. i was embarassed to confess that i actually stole them right out of my mother's best friends panty drawer. Mistress insisted i continue and to give her the com... Continue»
Posted by jenniferday 3 years ago  |  Categories: Masturbation, Mature, Shemales  |  
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Devina is blackmailed

This is how I become owned and f***ed to serve my Master…

I had arranged to meet a Dom Master in a hotel, we have spoken more than a few times on line and he has asked many questions about me and my fantasies. He seemed nice and only up for a bit of fun and nothing to heavy or long term. So we arranged to meet in a seedy hotel near King Cross in London one evening for a bit of fun. He would take a few humiliating pics & I would, of course suck is cock.

Anyway he told me how I was to be dressed - short black pvc mini skirt, tight white blouse (top buttons undone), black seemed stockings, ... Continue»
Posted by Devinatv 3 years ago  |  Categories: BDSM, Shemales  |  
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The wonderful feeling of a sissy penetration by yo

Nothing like that initial penetration, it is soo wonderful however there is so much more for me. just knowing that i intend to give myself to him submitting to his Big Hard Man Cock is a turn on. He wants me ready for him so he can show me his love and make me his girl.

The act of preparation, the douching and initial lubing, knowing I'm going be taking a real man cock inside me builds on the sexual emotion and makes me feel so submissive and feminine.

laying there in my nighty and panties and assuming the position he desires, normally face down, pussy up, legs together, wiggling my bo... Continue»
Posted by sissygirl 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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The Slave and the Sissy part Four

Pepper and I knelt on the silky sheets of the bed and studied each-other in disbelief; our cocks rigid and ready for relief. I took her sweet sissy cock in hand as I sniffed and licked at her face and neck; her skin as white and silky as the sheets. She thrust her slippery little sissy cock back and forth between my fingers as I teased her glistening little pink bell-end. Pepper panted with anticipation as she unhitched her crop top; her sweet little breasts stood firm and inviting, my cock throbbed as I licked and sucked at her stiff little nipples. She quivered and let out a little moan a... Continue»
Posted by midsummerman 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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I came to soon

Out in my car on a thurs. night / fri. morning calling at all the usual`s, as well as looking for places i`d not yet found, basically dropping in and stopping at every place i knew as a pick-up point an other places i`d just a hunch about really,i hadn`t a clue really but it`s just so nice to pull over along a lane or in a quiet village, sometimes just any where and grab my bag , hat if i`m wearing one hop out and take myself for a walk. With my heels clicking away and a cool evening breese blowing up and around the exposed flesh of my thighs above my stocking tops and barely covered by a mini... Continue»
Posted by Carla69Brown 3 years ago  |  Categories: Group Sex, Shemales  |  
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Brought to Heel

Brought to Heel.

Chloe liked shoes. No that doesn't even begin to do it justice. Chloe loved shoes. Court shoes, stilettos, strappy sandals, ankle boots, whatever. She loved them all so long as they had proper heels that allowed her to show her legs to their best.

Chloe had perhaps 30 pairs, she had never really counted them, she wore them whenever she could, certainly every day she wore one pair or another.

As soon as she came home from work, even while she was still in drab, her feet would be slipped into something with at least 4 inches of heel. Putting them on was almost a ritual,... Continue»
Posted by drooroo 3 years ago  |  Categories: Anal, Shemales  |  
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50 Shades of A Bookseller

*Crossdress Story*

So, I finally got a "proper" job and managed to move out of my parent's house.
It was a damn good job too, as my crossdressing was becoming increasingly difficult to keep secret. Numerous times my Mum would try to talk to me through my bedroom door, whilst also slowly creeping it open to talk face to face; why she does this I have no idea, but it's usually at a time when i'm either half dressed in a skirt and bra, with my cock hanging out or when i'm posing for timed photo's on my mobile phone (probably with my ass cheeks spread and my puckered hole pointing at the camer... Continue»
Posted by KitsuneTV 3 years ago  |  Categories: Shemales  |  
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xdressing school fucked by black teacher

This is a kinky sexual fantasy about my university teacher .Well it all started the first day my new teacher walked in the door .Six foot, very good looking black man .He was 15 years older than me very smooth with the girls.I just turned 21 and am three years into my transformation from male to female i have DD cup boobs. After 2 months of fantasizing and flirting with him i decided to make my move i needed that black cock inside me .I decided to wear the sluttiest school uniform i had it was short tight barely covered my boobs and i wore a killa pair of platform heels .Boy did i look like a ... Continue»
Posted by foxxiroxxi 3 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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At Jake's Cabin

Jake and I had been secretly seeing each other for about a year. We took every chance we could get to go and fuck. Jake’s famly had a cabin on a private pond in northern Minnesota. He had asked me to go up there with him for spring break. He told the fam that it was a guy’s weekend to fish and drink. It would be just us two up there the whole week. We did do some drinking but we fucked instead of fished.
We stopped at a small town just south of the cabin, probably about ten minutes away. He went into the convenience store to get beer and food. As he was in there I got into my bag and pulled ... Continue»
Posted by taylorbaby 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Kelly Pimps Out Chrissie (a Chrissie Conway story)

Kelly Pimps Out Chrissie (a Chrissie Conway story)


When I think back on all the years that I spent almost every day with Kelly I can't help but think that she
just may be a big part of the reason I'm a high paid "tranny whore" today. Kelly never missed on opportunity to
"pimp me out" whenever she got the chance, especially if it would benefit her in some way. Today Kelly is a
detective with the County Sheriff's Department. Going from a lesbian "pimp" to a lesbian cop just may be one of
the stranger lifestyle changes you'll see. OK so she wasn't a real '"Superfly" pimp or Manhat... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Sex Humor, Shemales  |  
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