Shemales Porn Stories
Page 120

turned into a slut by my dad

I opened my eyes, blinked, yawned, closed them again.

I felt confused, disoriented in a way that was... strange. It wasn't like waking up was supposed to be, I wasn't half asl**p. I can't remember getting in the bed, in fact I can't remember the last thing I remember. Where did consciousness end last? I was clueless.

I tired to move my body and I found it difficult. I could move though, I rolled over onto my stomach and opened my eyes, I was on the guest bed in the basement. Blinking didn't clear the fuzz from the world, so I went ahead and tried to get out of bed. As I stood I felt an i... Continue»
Posted by crossD93 3 years ago  |  Categories: Anal, Shemales, Taboo  |  
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My first Crossdresser - Part Two

We finished our drinks and got up from the table. As we walked out of the restaurant I could feel everyone's eye's on me. On us. Uncomfortable to say the least, and I wondered for a moment just how it must feel to her, or to anyone who lives outside the norms that our society dictates. We walked through an open lobby and entered the Sahara casino side by side, but a group of oriental tourists rushed past us and she stepped ahead of me to get around them. As she walked in front of me I once again saw just how sexy she was, and for the time being my discomfort took a back seat to lust. Beautiful... Continue»
Posted by abend 4 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Mommy and sissy


I really had been expecting to be shopping most of the
morning, but I got to the mall and miracle of miracles,
not only did I find a place to park close in, the mall
wasn't at all as crowded as I had expected. I got in
and picked up the few things I needed, and headed home.
One of the things I had to get was a couple of new
bras. It just seemed that the elastic in the ones I had
were wearing out. I sort of calked it up to their being
more cheaply made, every thing was any more it seemed,
being made in China or wherever.

I pulled into the drive and I didn't open the gara... Continue»
Posted by 6270daniel 6 months ago  |  Categories: First Time, Shemales, Taboo  |  
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Cutting Ms Betty's Lawn

My mother had suggested I might consider cutting Ms Betty's lawn as none of the other boys in the neighborhood would. All the other mothers hated Ms Betty and wouldn't allow their sons to associate with her. She was one of my mom's friends and I thought nothing of it, so I agreed to do it every week. It seemed Saturday mornings would be best, so I put her in my schedule and planned on the following Saturday to the first.

I was doing a great job with my lawn cutting service, picking up new clients from word of mouth after I did a lawn or two, but my schedule was becoming full. I needed to sa... Continue»
Posted by goodsonformom 2 months ago  |  Categories: First Time, Mature, Shemales  |  
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The Convoy

Several years back I was driving down I-95 south through South Carolina. I was dressed in fishnet thigh highs; platform heels, g-string, bra, all black. Over it was a black zip up the front mini dress. I had a hand held CB radio so that I could hear truckers talk about me as I passed them, and I'd been enjoying that for many miles. Clearly they all thought I was a real woman, and were very appreciative of me giving them all a little road show. After a while I came up on a convoy of 6 trucks all pulling trailers from a dollar store chain. As I passed them I got some horns blowing and all but I ... Continue»
Posted by dana213 4 years ago  |  Categories: Gay Male, Shemales  |  
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First fuck for Freda

I'm such a slut. It's not easy to know where to start. I suppose my routine - that's what got me into this, I guess.

Each morning, after my mother went to work, I had three or four hours before my shift at the factory started. I would get the box from under my bed and dress myself. The stockings, the suspender belt, the bra, the patent heels.

I would brush down my long hair and apply my make up, slip into a short mini-dress and admire myself in the mirror. I loved turning from Fred to Freda in the mornings. I'd always put my panties on last, for some reason; I just liked it that way. My ... Continue»
Posted by laceonlegs 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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transforming into ashley crossdresser

durring the day,i'm working i'm dressed in my work clothes,but when I come home I take a hot bath washing all over my body,then shave my legs,arms chest,and face.I even add babyoil in the water so that my skin becomes soft.then I will clean myself ass inside/out.then as i'm drying off i'll start ptting on my makeup,this takes me about an hour,I like taking my time so that my makeup looks perfect,so that when I put my wig on I'll have that female look.then go in the bedroom pick out something to wear.I more less like wearing short miniskirt,to feel a brezze up my skirt,such a turn on.but first ... Continue»
Posted by blonde68 3 years ago  |  Categories: Shemales  |  
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Book Store Bop By Cumhunger



A lady friend of mine Kelly had been riding to work with me for the past week
and every evening on the drive home we past an adult book store.I mentioned
something to her in passing that the lot always seemed to be full.She looked at
me with a mischivous grin and said... yeah all the guys who's wifes won't suck
their dicks frequent the place.

I've been there a few times to suck a few myself she giggled,what I said to her
in shock? Not straight laced Kelly,she's the demure type I never would have suspected to frequent this... Continue»
Posted by cumhunger 3 years ago  |  Categories: Anal, Shemales, Voyeur  |  
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A taste of Sandy

My phone rang and a husky feminine voice whispered I am here. Trying to hide my hard cock with my shirt I quickly went out to my hotel parking lot and found the Escape with a silhouette waiting. I walked up to the window and introduced myself “Hi Sandy, I’m Zef” Come sit for a minute sugar Sandy replied. I climbed into the passenger seat my cock straining hard against my shorts. Continuing were we left off on craigslist we talked for a few as I admired her dark nylons and pulled up skirt just covering her thigh. She had brown wavy hair to her shoulders, her eyes were covered with a blue shado... Continue»
Posted by Zeffer 4 years ago  |  Categories: Shemales  |  
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TOTALLY DOMINATED

I was out walking one night, a walk i used to make with my girlfriend. We had just broken up a few days ago. I don't know why I was walking here again, the memories weren't good ones. She had cheated on me with my best friend. Anyways, I was walking this familiar path through the city streets when I met a very beautiful woman. She was tall and slender with bright red hair. She had a huge rack, at least a double D, and a tight sexy ass to match. Her name was Cherry. This has to be my lucky night I thought when she asked me if I wanted to hit the bars and so I agreed.

I spent the night going ... Continue»
Posted by LORDLONE 3 years ago  |  Categories: Group Sex, Shemales  |  
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The Bondage Whore, Chapter 4

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.


Chapter 4 - First Day on the Job

Rachel barely slept that night, wondering and worrying about what exactly was going to happen on Thurday. It was terrible when she crawled into bed, realizing that she wouldn't be able to finger herself to orgasm, a nightly ritual for her. As she laid in bed, she chanted "$2,000 a week, $2,000 a week" to herself to try to keep herself upbeat, that she had made the right decision.

She finally rose at around 2pm, and showered. Her bladder felt full and she could feel pressure in her intestin... Continue»
Posted by thongcutoffs 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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I decided to try prostate milking today...

So last night when I was browsing the infinite collections on xhamster, i came across a video of a tranny ( <3 ) doing something called "prostate milking". I had never heard of this before so I click on the video to see what it is. First off the lady starring in this video was gorgeous, beautiful tits, great ass and a dick that was killer. During the video this lady first beats off and unloads a massive load of cum all over herself. I noticed that the video was only half over though and that I hadn't seen anything that reselmbled "prostate milking" just a tranny jerking off her cock lol. I kep... Continue»
Posted by MDvirgin 4 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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First night out as a sissy

Nervously, I came out of the restroom. I had never come out side fully dressed in my girly outfits. Rickey was about meet me in 15 minutes so I hurried. I found out what cross-dressing is when I was in high school and that was the time when I, with a slim and little frame started doing it. Inside house and at various encounters I had brought the dresses with me in bags. But outside among people dressed as a girl?! Now way, never…till now! I could not believe that I was outside wearing a tank top and hot pants! Every step I took gave me goosebumps. Every time Ilifted my head and saw any one loo... Continue»
Posted by CumLovingKitty 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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The woods

I met my sissy boy slut at the pathway to a secluded woods. Our eyes met as I walked past her and continued down the path, she followed without being asked and caught up And held my hand as we made our way to a hidden spot. My arousal was growing as she rubbed my arse through my trousers, I stopped by a large tree with a branch we could use to fuck on and over. I kissed her and ran my hands over her body the tight jeans allowing her bulge to been seen I un zipped her and put my hand in to feel silky panties and a hard cock! Then slowly pulling her jeans and panties down that rock hard little c... Continue»
Posted by kawa696969 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Used by Taxi Driver and more ch.2

The taxi driver headed off down the road towards the town again but on the way there walking along the road was 2 young girls and the driver pulled up beside them and asked if they wanted a lift?
They both smiled and said yes that would be great...town centre please. As they got into the back of the cab they were stunned to find David tucked up in the far corner.
They looked at the driver and then carried on getting into the cab. As they all headed into town the girls asked why he was there and why he was dressed as a girl and again the driver told them what he had done and the girls had a s... Continue»
Posted by Acebottom 5 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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The Day Lana Turned Me Into Her Daughter!

When I was much younger my neighbor, Lana, a divorcee, kept an eye on me while my folks went out of town. It was she whom formally introduced me to cross dressing and it was quite to my surprise. Back then I could actually pass for a woman due to my build. My hair was shoulder length and my body was small framed with feminine features.
I used to try on my mother's panties and clothes even though they were too big for me. Lana, on the other hand, had a great body. She was athletic and did not have a huge chest or big ass. She had great curves and was well defined. When my parents asked if ... Continue»
Posted by lovetopleaseu 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
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BECOMING MY BOSS MARGO'S SISSY BITCH BOY TOY.

WHEN I GOT CAUGHT GIVING A SUPPOSEIDLY QUICKIE BJ IN THE MENS ROOM STALL TO A CO-WORKER OF MINE, I WAS SURE MY FIVE YEAR JOB AS AN UNDERWRITER AT MY INSURANCE COMPANY WAS A THING OF THE PAST. LUCKY FOR ME, THE GUY I WAS PLAYING WITH WAS ONE OF THE OWNERS NEPHEWS, SO I WAS CAREFULLY TRANSFERRED INTO AN NEW POSITION ON THE SIXTH FLOOR AS THE ONLY MALE IN A SEVEN PERSON RESEARCH TEAM. MY NEW BOSS WAS AN OLDER (LATE 40'S)VERY CONSERVITIVE WOMAN NAMED JOAN. FOR THOSE FIRST TWO WEEKS, I WORKED LONG AND HARD IN ATTEMPTS TO NOT ONLY REDEEM MYSELF, BUT TO FALL INTO HER GOOD GRACES AS WELL. JOAN ... Continue»
Posted by cddixie 11 months ago  |  Categories: First Time, Shemales, Taboo  |  
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Should I cont.

Alot of us have had lustful thoughts of kinky sex. We even act on it. This is my first encounter with cum. I have been to 2 to 3 bars that have shemales. But I found her on craiglist. Just came to town, Islandergirl and was want some company. I replied and we meet a day later.
She was so tall atleast 6"4 with heels on. we began our date and eding at my place. She brought a dress like wrap and changed. I brought the drinks and lil smoke. Then we kissed and nevered stop. I never had anyone kiss me, so f***efully. Clothes were off now and she pushed my head to her medium size cock I thought. ... Continue»
Posted by Ammo550 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Chrissie and Julian

One of my oldest and wealthiest clients is a foreign born gentleman I'll refer to as Julian. I don't see Julian as often
as some of my other clients but always look forward to a session with him. I think the reason I so enjoy my time
with Julian is because I never know what to expect from him. Whenever his assistant contacts me to appraise me
of one of his impending visits my mind goes into overdrive. A visit from Julian is always interesting, always exciting and certainly
never dull.
Julian usually arranges a session with me after he's just completed a major business deal. I often fee... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Anal, BDSM, Shemales  |  
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My New Mistress

Ever love the feeling of a woman cummin on you? Well I felt that this evening after I picked up a random woman off the street who asked to be drive home. When we reached the house she asked me to come in. I did and she actually blindfolded me into here bedroom where she tied me up on her bed. I didn't need that but I just played along with it begging to be let go. Of course she didn't let me go. Then she started to tear off my clothing and found me wearing a bra and panty. Then she said,"Well aren't you dressed up nice?" she pulled on my panties and let go juggling my balls around. She laughed... Continue»
Posted by SissySlut9084 3 years ago  |  Categories: BDSM, Shemales  |  
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