Shemales Porn Stories
Page 62

Ladyboy Secrets

LADYBOY DIARY
by utubeslut

forgive the misspellings but inocent words get sensored
by the auto censeless

Diaries can be dangerous and have unexpected
consequences if they fall into the wrong hands.
Or the right hands ….


Early Spring and that meant a visit from my
Aunt Becky and my cousin Susie.
I loved Susie but she was kinda weird.
She had mood swings like she had permanent
PMS, very unpredictable.
Otherwise she was very sweet.
Crazy bitch.

The neighborhood girls were drawn to Susie
like a magnet. Crazy peop
... Continue»
Posted by Utubeslut 2 years ago  |  Categories: Lesbian Sex, Shemales, Voyeur  |  Views: 1208  |  
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TV Times

One evening I was online when someone wanted to start a chat with me. It was a bi guy who enjoyed cross dressing and having viewed his online profile I said “Hi” and we got to talking.


He was married guy named Mike and he had a very understanding wife who allowed him to meet men and allow him to explore his feminine side by dressing up. His wife did not participate with him and none of his explorations happened at home.


During our chat he explained he’d just bought a pair of long, nearly thigh high, boots and he longed to be fucked whilst wearing them. He was off th... Continue»
Posted by hotbiguy 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1207  |  
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Never Wanted To Be Your Girlfriend Ch. 03

Derrick really took advantage of having me captive that first weekend. He spent the entire time making me watch porn videos, and then had me recreate the scenes with him. He said, that he needed his girlfriend to be fully versed in all the ways he liked to be pleased. His appetite for sex was unreal. The only time we ever really took a break was to eat. And I have to admit, he made the most amazing strawberry milkshakes to go with the food. It was almost worth the humiliation of being fucked sideways by my best friend's b*****r just to get those shakes.

By Sunday night we were both exhauste... Continue»
Posted by sparkyking 23 days ago  |  Categories: Shemales, Taboo  |  Views: 1211  |  
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The "Ball" Game

Dad and myself had not had any "Barb" time in quite awhile. We never played when mom was around and needed some time together. A "boys" trip to KC would be just what we needed!

Soon as dad got home from work we headed for KC. He had put my stuff in the trunk and when got a ways from home he got it out. I jumped in the back seat to see what he had brought along for me to wear(he always chose my attire for me). Several very pretty dresses and a couple skirts, one was very short, and some blouses. An eight garter waist cincher and the most beautiful FF nylons! Black, coffee, suntan, all with s... Continue»
Posted by Barb51 2 years ago  |  Categories: Anal, Mature, Shemales  |  Views: 1203  |  
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My special day

Mistress Beth comes to me late in the morning and wakes me. She has let me sl**p in as today is my special day.
She takes me to the bathroom and there is already a feminine smelling bubble bath waiting for me with candles and rose petals on the bubbles.
She bathes me and gently washes my hair and whispers gently to me, converting my mindset from masculine to feminine as we talk about clothes and perfume and makeup.
She makes me stand in the middle of the room and raise my arms, proceeding to lather me all over and shave all my body hair, until my skin is smooth. Mistress Beth moisturise... Continue»
Posted by diesel41 5 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1205  |  
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Interview with Emma Stone

While I was in New York City, I discovered that the new Spider-Man film was being shot just a few blocks away from where I was staying. I was very excited for the new film, so I decided to head around to the set and have a look around.

So I was snooping around the city when I decided to grab a coffee. While waiting in line, none other than the film's star, Emma Stone, got into line behind me! I was babbling in no time; simply rambling on about how great the movie would be and so on. She was very nice, smiling and nodding and even laughing. Then, she was even nice enough to pay for my coffee... Continue»
Posted by IFuckedYourGF 1 year ago  |  Categories: Celebrities, Hardcore, Shemales  |  Views: 1201  |  
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Bus Stop

Dressed with my red 17cm boots, fishnet stockings, transparent skirt and transparent top I was waiting at the bus-stop to go back to my hotel in Barcelona, but suddenly a car behind be honked.


A beautiful Spanish guy stopped and looked at me, he couldn’t leave his eyes from my beautiful huge tits under the shirt. He whispered into my ear, “Need a ride?” I wasn't even startled and thought if this guy would have a nice cock as his body it would be a good start for the night…. I said “Sure, let's go.”
I saw tha... Continue»
Posted by Sexysamara 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1200  |  
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From big band to big bang

My special friend Marla and I like to get all dressed up and go out dancing. Well we ended up at a club that has different thems. The night we went was the Big Band era that played a lot of swing music. If you're not careful some of the moves has your dress flying out and even over your head. It's not unusal to see two girls dancing, so we could scan the patrons and see who was going to be the lucky guy. I spotted a tall handsome prospect so I gave him a little sneak peek up my dress to peak his interest. He took the bait and ask to dance. he was a very good dancer, swinging me around s... Continue»
Posted by slipn2panties 1 year ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1200  |  
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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: 1199  |  
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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 10 months ago  |  Categories: Shemales  |  Views: 1199  |  
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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: 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 1 year ago  |  Categories: Shemales  |  Views: 1196  |  
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Slut Bad Gurl on The Run

I checked into the motel with two suitcases, one for the traveling man and one for Victoria. Vicki likes to come out and play in strange cities where she can be herself in complete anonimity. She is a slutty, smoking sissy gurl!
I run the bath and put in some girlie bubbles. As the hot water fills the tub I unpack my sexy clothes, black lace bra and panties, stockings, waist cincher, 6" black open-toe pumps, and lay them out on one bed. I unpack my make-up and jewelry.

There's something so sexy about a seedy motel room!

The bath gets my skin all pink and girly and my clitty is ready for... Continue»
Posted by ignatzvictoria 16 days ago  |  Categories: Fetish, Shemales  |  Views: 1200  |  
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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 1 year ago  |  Categories: Anal, BDSM, 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: 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: 1197  |  
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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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My biggest ever-scary, but rue!

Since I'm pretty much sub, I don’t really ever say no, but maybe sometimes I should? I got an IM from a guy on a hookup site I sometimes visit and after a little bit of chit chat about the weather and what sorts of music etc we liked, he invited me to his place for an afternoon of fun. I'm usually horny and love to have fun, so I agreed and he gave me his address and digits. I asked him if he would prefer me dressed fem or butch, and he asked me to surprise him. Well, I love playing dressed fem, even though I'm not passable it seems to make guys just that little bit more turned on to see a nic... Continue»
Posted by LRock4fun 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1193  |  
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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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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 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 1189  |  
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