Shemales Porn Stories
Page 66

Jason's Joy Part 3

I parked my scooter at the side of the house. Walked through the unlocked gate and the unlocked kitchen door. I knew where Jackie would be and was not surprised by the house being silent. I was just about to slip past the sitting room door when a voice came from that room.
"Is that you Jason?"
"Yes Jackie." I replied. "I need the loo. Won't be long." I held the rucksack I was carrying down low so that she wouldn't see it.
"OK!"
I slip upstairs quickly and pause at the bathroom door just to make sure that she is not following me. Satisfied, I enter and quickly shut the door and lock it. I c... Continue»
Posted by dasilva1672 11 months ago  |  Categories: Shemales  |  Views: 1199  |  
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chase the pool boy (fictional)

after the thunderstorm and hurricane wreaked havoc on our town, and we had a lot of damage, my house was repaired but my pool was full of crap from the hurricane, no one could come out and help, everything was pretty much shut down, food was being dropped in by helicopter.
well finally, everything began to fall in place, but my pool still needed work, so my neighbor lisa(the shemale) came over and and said her friend was staying with her due to the death of his father, and knew a lot about pool cleaning and we worked out a price for the next day. i awoke about 6am and went into the kitchen ... Continue»
Posted by rollpayer1105 1 month ago  |  Categories: Gay Male, Shemales  |  Views: 1202  |  
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First Sissy Fuck part 1

I am in a hotel room and there is a knock at the door. I open it to let in a sissy girl in heels, fishnets and a very short dress. She has lots of make up and very red, shiny lips.
'I assume you are wearing everything else I requested' I ask.
She giggles and hitches up the dress to reveal lacy panties barely concealing a but plug at one side and a cock cage at the other.

She asks for permission to touch me, and when I nod she feels stokes my erection which rises to the occasion and trembles under the soft touch.
She kneels down in front of me and unzips the fly, releasing my fairly av... Continue»
Posted by honestjohn1962 1 year ago  |  Categories: Anal, Shemales  |  Views: 1198  |  
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Atrip to the dentist

My wife thought I was at the dentist but I was really with my special friend Sandy. It had been over a month since I could sneak away to see Sandy. My cock was wet and hard just from the ride thinking about what she would be wearing and how we would please each other. When She met me at the door I almost exploded just looking at her. She had blonde hair today in a long braid d****d over the front of her shoulder. Her eyebrows were dark thin lines followed by different shades blue all the way to her eyelashes. Her cheeks were painted a blush color and her lips a dark crimson. She wore a black ... Continue»
Posted by Zeffer1 2 years ago  |  Categories: Shemales  |  Views: 1197  |  
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Waiting for my uncle Jim to get back home. Part 4

My uncle Jim had just left to go back to work after catching dressed up in my moms lingerie. He made me suck his cock with him jacking off all over my face. He told me not to wash my face with his cum all over it until he got back home from work also. His cum was starting to dry on my face and I could smell it also. I went into the bath room and looked into the mirror to see what I looked like. I could see his cum drying on my face. I thought about washing it off but I reambered that if I did not do as he said he would tell my mom about me. So I did not wash it off but I could still smell the... Continue»
Posted by suecd58 2 years ago  |  Categories: Shemales  |  Views: 1202  |  
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Letting it all "hang out" 3

This is a continuation of previous stories, it includes
homosexual and transsexual activities. If it's not
your cup of tea, I respect that but don't read it and
leave mean and nasty comments.





Kelly and I had just sucked each others cocks, exploding
down the others throats. My finger had been slowly encircling
her rosebud. She stopped me, turned and slithered up my
body until our cocks were touching. She looked at me in my
eyes, smiled, slid up some more until we could look directly
into each others eyes. Our lips met, just lightly at first,
I could taste my cum still on her... Continue»
Posted by Bigrodtaz 29 days ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1199  |  
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A Fantasy Realised

I have a great many fantasies and have been lucky enough to realise some of them. This has been a very mixed blessing. Some have been fantastic, even better than the mental image but others have been disapointing, for various reasons and did in fact turn me off from the fantasy altogether. The following is one of the succesful attempts.

I'd been chatting to a guy on the internet over the course of a couple of weeks. He was quite dominant, which I liked and the chat was very erotic.

He asked me if I had any fantasises and when I said yes, he asked me to tell him one.

I'd had a recurrin... Continue»
Posted by ksopen1 2 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1195  |  
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Sissy Emma is Turned Chapter 4

I couldn't go outside dressed like that could I?

Here I was f***ed to dress like a slut in locked on heels, barely black stockings, mini skirt, frilly white blouse with which could clearly see my black bra and 38d breastforms and heavily made up face. I would have looked like a reasonable vision of a woman, albeit a very slutty woman other than the fact that my new Master and my ex-wife had failed to give me a wig. So to anyone seeing me it would be clear that I was in fact a feminised male. This was going to be humiliating.

But I couldn't think of a way out. At the least it was going to... Continue»
Posted by emmahighheels 1 year ago  |  Categories: Shemales  |  Views: 1195  |  
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Fringe Benefits

Shawn showed his employee badge to the TSA agent and was waved through to the metal detector. He quickly slid off the lanyard placing it into small bin to take a ride down the conveyor belt. Once he was fully cleared, he collected his belongings and headed away from the security checkpoint to the Office of Physical Plant. He clocked in then spoke to his boss’s secretary before heading out to make sure the trash bins in the terminal were empty.

The 29 year old airport custodian landed this job just six months earlier thanks to his aunt, who was the administrative assistant for the deputy may... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1194  |  
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Happy Birthday to Me, Part 2: The Early Birds

Well, in case you didn't know, this is part 2 of a sordid tale. A tale of debauchery. A tale of depravity. A tale of a crossdressing cockslut with an insatiable appetite for cum. You see, it was my birthday and for more details on how I celebrate, see part 1.

I had just had sex with 19 young men over the course of 4 hours, and collapsed, exhausted for a brief power nap. I layed down at 430 am and when I woke to the sound of my alarm at 515, I lifted my head from the pillow and was surprised to find my face stuck to the pillowcase. Now, you know you had good time when you wake up and... Continue»
Posted by cdsexslut 26 days ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 1200  |  
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sissy lola gets a treat1

Last night was my first night as a sissy maid for my beautiful goddess maureen and i have been instructed to tell you what a dirty little cock sucking whore i have been.

I have known goddess maureen for a while now, she has been giving me instructions via webcam. She would make me flog myself or fuck my ass with a huge black dildo untill she was amused. So last night, i received a set of instructions telling me that i must prepare for a very special night. I was to lock my cock in a chasity device a week before. I then had to post the key through goddess maureens door. She said i had to get... Continue»
Posted by sissy_bitch 2 years ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 1193  |  
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shemale adventure

I was at the bar for the night. relaxing, putting down a couple drinks. I had started talking to another guy at the bar. we had a lot in common. after a good couple of laughs, a woman came up and joined in. we were suprised, she was really hot! we sat around for a cpl minutes, talking and laughing. as the bar was closing, me and my buddy needed to find cabs to get home. the woman offered to give us a lift, and we saw no problem, and agreed. on our way back, she said she wanted to drink more, and I said I had some beer at my place. so we all decided to go there for a little bit.
as we get set... Continue»
Posted by ballin420 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1194  |  
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gut next door

Well after Dan next door find out I was a crossdresser and we had sex.I knew there was something I had to do.
I woke sunday morning and loaded some boxes in to back of my pick up.He seen I was dressed as Paula and came over and asked what was in the boxes.The stuff I don,t want anymore all of Paul's old clothes.For now on you only see Paula.
He said really?Yes, what about the other nieghors he asked.I don't care what they thing it free world and they know.I said well I better take this stuff and but it collection box for homeless.He opened my door for me and gave me kiss before I left.I... Continue»
Posted by cdpaula 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1190  |  
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dogging tv slut

It was dark enough now I thought. It was about eight o'clock on a warm spring evening and I was ready. I had started getting ready about three hours earlier. I'd showered, cleaned all those special parts, applied my make-up heavily and dressed. I was wearing a skimpy flower print top over a black silk bra, my favourite suspenders, black leather micro mini skirt, black gloss stockings and high heeled black knee length boots. I peered from out behind the curtains. Yes the street was clear apart from some young lads on the nearby street corner. It was only about ten yards to the car. Quickly I c... Continue»
Posted by JuliaMiller 2 years ago  |  Categories: Group Sex, Mature, Shemales  |  Views: 1190  |  
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Gina

Gina

you hate yourself. that's all you can think of. every day. every night. you hate what you are. you hate what you have become. it's been one year since you've been k**napped. one year locked in this house! in the middle of nowhere. one year since the last time you saw your office. your friends. your wife. your son! it's been one year since you were normal. if you only knew... you would never have opened the window of your car! that guy would never have sprayed you! you would still have your life...


you hate what you have become...


*****


1 year earlier...

this nightmare... Continue»
Posted by slim_krak 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1190  |  
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Brianna...

Rob asked me to house sit and I didn't hesitate since he lives in a
beautiful big house on the end of a Cul de Sac. There is only one
house next to his and no one can see his backyard except the house
next to his.

His neighbor Bryan is a local college professor at the community
college and doesn't seem to mind when we skinny dip in the middle of
a Saturday afternoon. He seems cool so I thought this was going to
be a great two weeks. I had no idea what was going to happen during
these two weeks.

It was the first Saturday of my two week stay and I was sitting in
the back yard enjoy... Continue»
Posted by NaughtyNshy 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 1189  |  
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Rendezvous with Cheryl

Pulling up to the motel my cock was already rock hard just thinking about Cheryl. It had been a few months since my last trip to Baltimore and I so wanted her. We had met on craigslist about a year ago and rendezvous a few times. Now it is kind of a regular thing whenever I am traveling through. Cheryl always grabs a room at this seedy super 8 and then text me the room number. Cheryl looked so sexy today she had dark brown shoulder length hair that curled at the end, nicely lined eyebrows, long and dark eyelashes, her cute cheeks glowed matching her light pink lips. Two long earrings dangled f... Continue»
Posted by iheartm2f 8 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1188  |  
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Nice surprise on the journey to work

This is a deliciously erotic story sent to me by my fellow writer Ila, I hope you enjoy it as much as I did and also the second part of the story which is to come..

I got up early this morning for a change.  I had a feeling that today was going to be a good day.  At the time I didn't realize just how good.  The sun was shining for the first time in several days.  That, at least, was a good sign and an improvement over yesterday's rain.

I headed off to the bathroom for my morning ritual.  A quick shower and then I was ready to get dressed.  I put on my normal businessman's uniform ... Continue»
Posted by keliana 3 years ago  |  Categories: Shemales  |  Views: 1187  |  
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Lakeside Awakening

Lakeside Awakening



If anyone had told the way I’d meet my soul mate a few years ago, I never would have believed it. It was my senior year of high school and I had recently gotten out of yet another bad relationship with a girl. Lina had been a pretty, chubby blonde with a nice personality but a nasty temper. We just didn’t click after a while and I was feeling down on myself for not being able to hold onto a girl for very long. My friend Dan took me to a friend’s house where there was a party going on and I went along mostly to distract myself from my thoughts. The place was a dump an... Continue»
Posted by valeriuscatullus 3 years ago  |  Categories: Shemales  |  Views: 1185  |  
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Mommy catches you masterbating....

Well first, I walk into your room and dont know that you are home... It had been awhile since I saw last because you have been working at your new job so much lately... It had only been a few weeks since you got home for the summer from college, and I was celebrating having you in the house again...

You dont even notice me, since you are propped up on the other side of the bed, half naked with your dick hanging out...I dont notice you, but you see, im being sneaky too...I was seeing if you were home so that I could have a cigarette... youve never seen mommy in such a hott outfit...or smoke ... Continue»
Posted by dawichrister1 3 years ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 1184  |  
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