Shemales Porn Stories
Page 10

Young Master Ch. 02

There I was, still impaled on a shemale's cock, one belonging to what was supposed to be my sissy slave, wearing her bra, her cum on my cheek along with my post-fuck smeared make-up, and my cum running down the full length mirror. "I fell" wasn't the best explanation for what happened, but it was all I could think of with my step-father's hulking frame looming over me. I knew I was fucked...well more fucked than already had been, but I still hoped for some miracle to save me.

"You...fell? I'm not even going to begin to catalog the many reasons that is the most insultingly stupid lie I have ... Continue»
Posted by bi_hengst 3 months ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 421  |  
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Young Master Ch. 01

It was supposed to be the best day of my life...and maybe it was, but definitely not in the way I planned.

My 21st birthday...my first day as a man, as a true lord of the Manor...my first day as a Master. I was so nervous I threw up my lunch. Not very manly, I know, but just the thought of having my very own sissy to play with had me teetering between the giddy excitement of a k** right about to open the biggest present under the tree, and the stark terror of officially being a man in my step-father's eyes...how could I measure up to him? I felt destined to disappoint him...and I didn't eve... Continue»
Posted by bi_hengst 3 months ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 1824  |  
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Young Sissy Ch. 01

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.

*

I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a... Continue»
Posted by bi_hengst 3 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1160  |  
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My Boss Tricked Me

I work for a cell phone company. Part of my job is to travel to cell phone towers and fix any problems they might have. I enjoy it but am on call most weekends. Now I consider myself a man in public but at home I love dressing up as a slutty tramp. I love the feel of lingerie on my body. I had a few experiences with a man but it was mostly mutual masturbation. My crossdressing is a secret to everyone except the few I have met online.

Most Friday nights me and the coworkers go out drinking. Just a bunch of guys out having a good time. One particular Friday I got really d***k and my superviso... Continue»
Posted by sissysadie 3 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 9817  |  
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The Upsell





The Upsell


I walked in holding the busted cable. The stupid iPod cable had a cut in
it, or something, I didn't know. All I knew is it didn't work anymore.

Adelaide's was the new department store in town. They were having an
opening-week sale and I figured it would be a good chance to replace the
cable and check out the new place. I'd left my roommate Cal on the couch
and went out to get our music situation sorted.

I headed to the electronics section and began poking around, looking for a
new cable. Before too long I felt a tap on my shoulder and turned around.

... Continue»
Posted by klammer 3 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1262  |  
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Preparation of passive slut pt. 1

I had been meeting my master for a while, and had got used to dressing as a woman, being stripped naked in public, spanked and being fucked. I decided to take things a step further, and my master agreed. We met in a cafe one evening, I was dressed as usual, like a little slut. I was wearing a tight red dress, black stockings, red heels, my fake silicone breast forms contained by my red bra, my useless little dick squeezed into a red thong, and my hair had now grown long and dyed blonde. 'Ok you little slut, I'd like you to meet your new Mistress, she is going to transform you into a horny litt... Continue»
Posted by barefoottransnude 3 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 716  |  
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The first meeting

I knocked on the door, it opened and I walked into a room I had seen many times on XH. I turned as she closed the door and came towards me. I looked at her long black hair, plain blouse, short denim skirt and black hosiery with black mid heeled shoes. I put my bag on the floor, faced her and said “You look so good, I’m all yours”. She smiled nervously; I knew this was her first time. She drew closer, her dark eyes fixed on my face. Gently she put her lips against mine, I let my mouth open a little and she took the hint, pushing the tip of her tongue into my mouth. We stood quietly, gently sway... Continue»
Posted by spankbuoy 3 months ago  |  Categories: BDSM, First Time, Shemales  |  Views: 670  |  
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The Transformation part II

I was in the closet dangling surrounded by mirrors for what felt like an eternity. Mistress Anna, my once friend now dominatrix, had helped me to the best orgasm of my life but my penance was to stay handcuffed in her closet seeing my sissified self in all the mirrors she had set up around me. I felt ashamed and aroused all at once. It was probably a few hours later that the plug finally slipped from my ass as I started to doze. The glass plug thudded on the carpet and woke me from my daze. I could hear footsteps.

She was gentle with me. She carefully lifted me and unlocked the handcu... Continue»
Posted by fictiong 3 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 2079  |  
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Being Vicky for the first time

(November , rain storms releases the opportunity to go and take a lonely car ride .... what can possibly go wrong?
Damn it….the car engine stops ,typical my bad luck , the torrential rain I am now soaked , who will stop at this hour to pick up a man in a terrible state wet sad mad…at his luck my thoughts take an abrupt end simultaneously with the car passing before me and slowly stops a few meters away from me)
E: I guess you didn’t see that coming? shouts the girl running with an umbrella towards me
Me: Thank you, I saw the weather I couldn’t “see” the car abandoning me on my own... Continue»
Posted by vicky_cross33 3 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 1265  |  
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Babysitter Part 3

From: A K little s****r Alyssia

Babysitter Part 3
________________________________

My life as Alyssia continues, please let me know if you enjoy it or have
suggestions or just want to chat. I would love to commiserate with other
writers and readers. I truly appreciated and loved hearing from those who
wrote to me and gave me the courage to continue! Thank You. All rights
reserved.

littles****ralyssia@yahoo.com

Babysitter - First Date

I'm still laying on the couch where I passed out last night after Paul
called when I drift awake. I look down my smooth legs to my ankles ... Continue»
Posted by jayymie 3 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 2322  |  
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Babysitter - Part 2

From: A K little s****r Alyssia

Babysitter - Part 2

I'm a mess in the mirror, well, I think I look sexy too with my hair all
tussled, a little cum rubbed over my cheeks and chin, and a grin like the
cat that ate the canary. The dress has some wet spots and a few small gobs
of his cum. I wash up as best I can and blot the spots on the dress, I
start thinking, Nicole is going to kill me! I might have ruined her dress
and I just gave her man a blowjob. That could be a problem. I still can't
believe it!. He kissed me and I sucked his dick! But I know I want to do it
again.. Did I real... Continue»
Posted by jayymie 3 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 1626  |  
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Babysitter

A K little s****r Alyssia


Babysitter

I had been watching Paul and Nicole's two c***dren for a while. She was
very pretty, about 5'8", nice legs and loved to show them off. She towered
over my 5'6' in her heels, Paul was about 6'1 or so, clean shaven and a
trim wide shoulder athletic build, they made a very good looking couple.
They would go out, she in a sexy dress and heels, and he in nice pants and
shirt, or a suit sometimes dancing or parties I guess, I never really
cared. It was a cool gig, the k**s were young, and went to bed around 8 or
so, so I had lots of time to mys... Continue»
Posted by jayymie 3 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 1628  |  
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Best Friend ? part 6

As we drove off sam asked me if i had any idea about what was happening ? i said i didnt, well let me explain i have now taken you and linda over, she loves my big cock and enjoys the way i treat her rough, as such i intend to keep her as my own fuck toy, you are now a plaything i know all about you going to the toilets etc and as you give a good blow job i will be useing you for that, but i will be sharing you with some of my special friends, i have shown people your photos and you are popular ! but wait till they see ones of you dressed as you are now,today we are going to peter and annes ho... Continue»
Posted by loopylinda 3 months ago  |  Categories: Anal, Shemales, Taboo  |  Views: 409  |  
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Photographer's Assistant

By Teresa Wood

Photographer's Assistant

It had been my mom's idea that I get a part time job, but I certainly
didn't argue with her. I was going to be sixteen in a few months and there
wasn't any other way I would ever get a car. Not that I really needed one. It's
not like there was anywhere I needed to go.
My name is Louis, just plain `Lou' to my friends or at least the casual
acquaintances I've made at school. The truth is that I'm a loner, I just prefer
my own company, and so my list of true friends is pretty short. Not that I'm
disliked or anything. I'm quiet and most of the... Continue»
Posted by jayymie 3 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 14017  |  
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A Lodger's Leanings

By - Lucy Roberts

A Lodger's Leanings

I was brought up by my Mum as my Dad left us when I was very small.

Mum and I had a good relationship and, only having a female role
model, perhaps it wasn't surprising that I got into wearing my Mum's
clothes. At least that was where it started but as I entered my
teens I used quite a bit of the money given to me at birthdays
and Christmas to buy my own clothes.

By the time I was about 13 I was used to having the house to myself
while my Mum was at work. As well as being able to have friends over,
it gave me plenty of opportunity to ... Continue»
Posted by jayymie 3 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6655  |  
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I Disco

By - Tex Lee

I Disco

I discovered crossdressing in my early teens when I was once
using the bathroom I noticed my mothers red lipstick on the
bathroom counter. I opened the tube out of curiosity and
twisted out the red phallic looking lipstick and felt
compelled to put it on. I felt a strange and exciting sexual
arousal that I never felt before and soon was wearing
lipstick and masturbating every chance I got. Eventually I
started wearing my mom's and s****r's panties and bra, then
dresses, skirts and high heels. By the time I was 16 I
accumulated a nice little wardrobe of sexy... Continue»
Posted by jayymie 3 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3186  |  
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Confessions of a She-male Toilet slave.

CONFESSIONS OF A SHE-MALE TOILET SLAVE
CHAPTER 8 - TESTED AND FOUND WANTIN'...

This is a short story about my first wife, about the day the World changed for me. When we married she was bi and a swinger, an older woman (40), and lot's of fun, I was young, barely 18, we swung all around town, her and her pretty boy. As soon as she got into my ass it was her friends using me, not her sharing her 'toys' with me... By the time we split up she was living as a hardcore biker dyke, and I was chained in a k**die pool in the basement serving as a human toilet, urinal, cum dump, and fist hole for w... Continue»
Posted by bucketkunt 3 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1350  |  
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24 hours with steve 11.00am till 00.00am

I have always considered myself to be a straight young man 27 years old, even though i have sucked a mans cock once or twice in my life time. i have a wife who likes sex (well wants it at least once a week). Me having a higher sex drive turned to xhamster for sexual relief. i was in to watching gangbang films for a while then cuckolding but then i discovered CEI videos, i got to a stage that whenever my wife left the house i was on xhamster jerking of and eating my own cum, i would even come home on my breaks to do this. i dont even like the taste of my cum that much its just the thought of ac... Continue»
Posted by cuck_old_82 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2050  |  
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Apartment to rent

When my wife suggested that we rent out the guest rooms above the garage to a college student it sounded like a good idea. It was very much like a small apartment, with a bedroom, bathroom, and small living room. No kitchen of course, but we could share ours and it seemed like a good way to make a little extra every month. We'd only recently gotten married and had just bought the house, so we could use the money.

Being my wife's 'project' as it were, I left the details up to her. I was working hard at my new job anyway. We were both just twenty-six then and recently graduated from the unive... Continue»
Posted by Alic91lovesporn 3 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 12671  |  
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Renting out a room

When my wife suggested that we rent out the guest rooms above the garage to a college student it sounded like a good idea. It was very much like a small apartment, with a bedroom, bathroom, and small living room. No kitchen of course, but we could share ours and it seemed like a good way to make a little extra every month. We'd only recently gotten married and had just bought the house, so we could use the money.

Being my wife's 'project' as it were, I left the details up to her. I was working hard at my new job anyway. We were both just twenty-six then and recently graduated from the unive... Continue»
Posted by Alic91lovesporn 3 months ago  |  Categories: Hardcore, Shemales  |  Views: 2967  |  
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