Shemales Porn Stories
Page 4

The Slithering: The Cloak and the Dagger

The Slithering: The Cloak and the Dagger

The young boy quickly wiped the large amount of sweat from his brow,
finding it very difficult to withstand the unbearable heat of the dingy
workshop as he placed the fiery, malleable blade against the flat
surface of the blacksmith's anvil. The thick, black smoke choked his
lungs and he gagged a bit while trying to maintain his composure.
Grabbing his small hammer with his left hand, the boy raised it upwards
and then f***efully brought it down against the blade with a loud
strike, as bits of heated metal spewed forth. This was a ... Continue»
Posted by klammer 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  



He coluld do nothing to escape the lip gloss brush across his lips as he
had just started the engine to the car and done up his seat belt when she
reached over and applied it to his lips. He had thought she was going to
put it on her own lips and was caught by surprise by her sudden act.

She told him, "Pucker up your lips like you see other women do."

Having just had lip gloss put on his lips against his will why did he
obey this direct instruction? He could have refused as he wasn't a woman
was he? He felt the sticky feeling on his lips of the lip gloss she
... Continue»
Posted by klammer 1 month ago  |  Categories: Shemales  |  

Who is seducing who?

One of my main fantasies involves me seducing a girl in public... in a cafe for example! I've only just met you & you are so glamorous I am absolutely captivated! We are in a 50's style diner & it's really busy but we have a table in one of those booths. We;ve ordered our food & are chatting easily all the while flirting uncontiolably,
We're sat opposite eachother at the small table & your stocking clad leg accidently brushes against mine I can feel the silkiness even through my jeans. You apologise & I tell you thats absolutely fine & I reach my hand under the table & touch you kneee.. A sm... Continue»
Posted by chrisluvsgirls 1 month ago  |  Categories: Masturbation, Mature, Shemales  |  

My first blowjob (sirky)

I started crossdressing when I was in high school. Small things that I had found or stolen: stocking, make up, thongs... I loved to look sexy, but I didn't feel gay at all. In high school I met a boy some years older than me. He was a great friend, we used to go to his house to play videogames since I didn't have a console.

One day he started dating a girl, and we started to talk about porn and sex (I was virgin, so I was really interested in that topic). We eventually ended watching some porn. I had some magazines, but no videos, so it was awesome to go to his house, play for a while with... Continue»
Posted by sirky 1 month ago  |  Categories: Gay Male, First Time, Shemales  |  
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Transwoman or Sissy Faggot?

When a male decides to transition and become feminine she
may decide to be as womanly as possible, many are ladylike
and demand and deserve to be treated with respect.
Many are promiscuous to the point of being whores but they
still get treated like women because, frankly, they have tits,
very often big boob job tits.
But a whore is still a whore and gets treated like one.

Sissy faggots are lower on the respect totem pole than
trans woman whores though.
They usually have smaller or NO tits but they usually shave
off their body hair and feminize themselves.
They're somewhere bet
... Continue»
Posted by yutubeslut 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  
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Becoming a Sissy Bitch

Becoming a Sissy Bitch Part 2

As I stood there completely naked in front of this wonderful woman I realized that what was happening to me would completely change my life forever. She looked me straight in the eye and asked me how I felt. That question came from a different part of her than the dominant woman that just a few minutes ago slapped me and admonished me for not addressing David correctly. The question was almost motherly in its tone. I felt completely free for the first time in my life to say what I felt.

So I responded, “ Mam I feel free, I want to be a pretty girl so badly ... Continue»
Posted by yummycumshot 1 month ago  |  Categories: Fetish, Hardcore, Shemales  |  
  |  1

My slow realization, I liked dick.

So as most stories go, it started off with curiosity, and a little bit of alcohol. I was freshly 18, moved away from home for school and wasn't really tied down to anyone or anything at the time, but I had this gnawing curiosity ever since I was young, I always knew I was a little bit bi or at least something close to it because even when I was young I liked the look of some cocks, and I loved the idea that there was people out there who had cocks and were women too.

While I was away, I lived with 2 other guys, they had no idea that I had these feelings and they still don't to this day, I m... Continue»
Posted by SwagorTrusty 1 month ago  |  Categories: First Time, Shemales  |  
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Uncle Bobs Lesson

I posted this story on another site years ago. I had some nice feedback, but not many views.

In '91' during my senior year of high school my folks split up just after my18th birthday late in the summer. The whole thing was a mess, with me being sent off to relatives while my mom took my younger siblings to the gulf coast to stay with her parents. They sold the house and Dad moved to be with his new future 'ex-wife' outside of Dallas.

Since I am older by about 7 years, and was in high school I did not want to leave town in my last year. No way did I want to be sent off to someplace I did... Continue»
Posted by Cuckarama 1 month ago  |  Categories: Gay Male, Shemales, Taboo  |  
  |  1

The Pill - part 1

Early in the morning, I parked the van in the multi-storey car park and sat there looking out over the rooftops of the shopping centre which serviced the needs of this drab London suburb, without really noticing what I was looking at. My mind was elsewhere.

It was a major decision I was taking; the potential for disaster was huge, but the rewards, if it all worked as promised, would be immense: a dream come true, if only for a day.

I looked down to the small pill case in my hand, surprised that I was holding it, as I did not remember having taken it out of my pocket. I flipped open the l... Continue»
Posted by mallenwc 1 month ago  |  Categories: Masturbation, Shemales  |  

The Pill - part 2

This is the second chapter in the story of my adventures in London, on the day when I took a small pink pill and my face and body transformed into that of a beautiful young woman.

However, I knew that I only had 24 hours before the effects wore off and so determined not to miss any opportunity as I had a day of sexual adventures, some planned, some on the spur of the moment.

The story so far: I had started my day in the back of a van, in a multi-storey car park, choosing the outfits I would wear during the day, and discovering the wonders of my new female body...

====================... Continue»
Posted by mallenwc 1 month ago  |  Categories: Shemales  |  
  |  1

Seducing Nelly, a TS erotic story

I first noticed Nellie on a Friday evening when my fraternity and her sorority got together to make a homecoming float. She had gorgeous blonde hair that flowed down to her shoulders, she knew exactly what she was doing with her eye makeup, lining them in black with a smoky finish. Once my gaze connected with hers I couldn’t look away.
I smiled, grabbed a couple beers from the ice trough, walked up to her and offered the drink. She smiled, accepted and introduced herself, “I’m Nellie” she said, I told her my name, we shook hands and both smiled. Her teeth were perfect, bright white surrounded... Continue»
Posted by Mskyeuploads 1 month ago  |  Categories: Anal, First Time, Shemales  |  
  |  5

Becoming a Sissy Bitch: Part 1

This all started for me when I was very young, I'm sure you've heard
it all before, Mom leaves for the day, sissy boy gets into her clothes etc etc. I did go through that phase and it was strong for me. However my story takes an unusual turn in my early adulthood. My experiences changed dramatically.

I was just starting college and was working after school everyday at a downtown firm that published catalogs, manuals, and those types of books. I would go there everyday after class and usually put in 4 or 5 hours and then head home to catch up on my chores. I started in the mailroom, as clic... Continue»
Posted by yummycumshot 1 month ago  |  Categories: BDSM, Hardcore, Shemales  |  
  |  11

Riding along the edge with a slutty gurl :)~

We take our time in the shower making sure to be very clean, shaved, lotioned smooth and fresh... After choosing the porn - We slip into panties and bras, then do our hair and makeup - ohh the firetruck red lipstick is really hot! Soon enough we are doing nails and prepairing the room for a long steamy passionate session... We have several fun and wild toys to share... We pile them with extra towels on the bed tables... You choose some hot lingerie and we sit on the edge of the bed and watch each other dress... I slip into my yellow dress, black pantyhose and yellow 6" fuck me pumps w... Continue»
Posted by hotbrandilove 1 month ago  |  Categories: Fetish, Hardcore, Shemales  |  
  |  1

My s****r

My s****r caught me crossdressing over the weekend when she stopped by, and she was rather interested.. She stood there looking at me as I was dressed in my stuffed bandeau bra, a black sports bra over that with a gray VS cammy, and I was wearing my black VS boy shorts panties under a pair of black yoga pants, my cock was hard and bulging out of the yoga pants! She said I love how you look! "You have a nice plump girl booty in those yoga pants!" she said, she too was wearing a white cammy a bra and black yoga Capri's.. I didn't know what to say after she said that to me, all i replied with was... Continue»
Posted by cdyogas 1 month ago  |  Categories: Fetish, First Time, Shemales  |  
  |  1


AZNSWAG here in toronto , canada !

i dont even know how to start this .. because everything i can sense and feel is still so fresh .. and im by no means an author ..
this story is gonna be as raw as it gets lololol .. i think what happened this week will be stuck with me for the rest of my life.. im only writing this now because it is sunday.. and now it is time for me to recover and get some rest for what remaining time i have before i end up going back out for more debauchery.... but i also wanted to reflect and share what happened with me this week ..

i live in a luxurious condo i... Continue»
Posted by AZNSWAG 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  3

Brittany The Cheerleader

It was my second year as an assistant counselor at River High School. I was young, in my mid twenties. Everything was typical in the small town school. I would help students with scheduling issues, direct them towards colleges, and help them with different scholarships and programs that would benefit them. It was entirely unremarkable and nothing out of the ordinary happened until I met Brittany.

One day a woman walked into my office. She was tall for a woman of her age, yet very slender and petite, with an almost non-existent chest, gorgeous round bottom, tanned skin, and long deep brown... Continue»
Posted by wedgietime 1 month ago  |  Categories: Fetish, Hardcore, Shemales  |  
  |  1

It's been a long hot summer

If you've read my blogs you know that Kimmy and I have had some incredibly hot encounters, but the summer months have been rough on a married closet sissy like myself.f****y obligations ,works schedules and vacations have left little or no playtime lately.But things are starting to get back to normal. The sky"s opened up and our schedules synced up for a window of opportunity this morning,neither one of us could host but we did have some time to get together,I must interject that we have a sort of sissy bucket list that we want to work through what happened this morning is ,or was on that list... Continue»
Posted by jeper11us 1 month ago  |  Categories: Gay Male, Shemales  |  
  |  3

First meeting with Dom sissy mistress

I was a longtime secret panty sissy who played in private and only dared dream of finally meeting someone face to face when I met Miss Jamie on xhamster. We had an immediate rapport online and before long she suggested meeting. Of course, with her long experience as a sissy, and with me being an obviously natural submissive, she would take the role of teaching me my proper place as a submissive sissy. This is the account of that first meeting.

Miss Jamie's logistics were simple:
I was to park at a nearby shopping center and wait for her.
When she arrived, I was to get in her car.
She wou... Continue»
Posted by Shelleyisasissy 1 month ago  |  Categories: Fetish, First Time, Shemales  |  
  |  1

Daddy's Little Slut

Here I am, surfing on my favorite porn site. My dirty little urge has taken hold of me again. After a long period of deniying myself the need to dress up, i relapsed again. I bathed and thought of trimming my pubes a bit, but ended up shaving myself completley again. I tend to do it in my urge to cam and show off my sexy body and after cumming i regret it instantly. It makes my life difficult because i have to hide my hair free body from all my workmates and friends. So here i am, shaved, smelling really good from my favorite gucci scent, wearing my dark hair wig, my sexy stockings and lingeri... Continue»
Posted by ignitron 1 month ago  |  Categories: Fetish, Masturbation, Shemales  |  
  |  3

Dragon's Hole Part 2

On the long trek back to the room, something else catches your eye, another sign. This one says Dragon’s Persuasion. Just the name on the sign is enough to pique your curiosity, so you turn and head down this hallway. Unlike all of the other halls that are adorned in medieval decorations, this one has various colors running horizontally down the hall. The colors, you notice, are the colors of the rainbow, but very faint. You wonder what could be down this hallway and continue along until you reach a heavy oak door. You push this door open and right away, you hear moans. Not the same moan... Continue»
Posted by sabre72 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
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