Shemales Porn Stories
Page 8

Locked In Chastity – Sissy

“Oh, dear, baby! This won’t do at all. Another two months it is!” Amelia chirped as she gazed upon her helpless husband, “You know the rules!”

John was fully aware that being caught with his hand on his straining little sissy clitty, desperately trying to stroke it through its cage for the third time, meant that his period of enf***ed chastity would now last six months. In the brief, thrilling moment of his quickening heartbeat forcing bl**d into his face, John remembered the first day he had been locked up by Amelia, and a shiver ran up his spine. They had been happily married for nearly f... Continue»
Posted by JSissy206 2 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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My sissy son,by his dad and lover Part 7

Thought I'd tell you what about Carol and I.

Carol had given me hand with my make up and she'd dressed me up in my lingerie dress,slip,stockings and heels
She looked at me up and down,inspecting our handy work, "You know honey,you're just as cute as your 'daughter'!"
I was taller than her, (even more so in 4" heels) and she pulled my head down and kissed me.."Now we have a few
'select' friends who'd like to meet up with you..and your sissy daughter.They are our age really..professional husbands
and their wives,nearly all are bi-sexual,although some of the men are 'straight'.Now ... Continue»
Posted by chocandres 2 months ago  |  Categories: Fetish, Group Sex, Shemales  |  
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I lost my virginity to a shemale

As living in an Asian country where sex is very personal thing and no body wants to share any thoughts regarding that.Me as a person wants to try it in a different way and which took me to another level of that,which I had never thought of.
Being a young 18 year old boy I use to see porn just to control my thoughts and body,like every guy use to do.Then while searching on net I came to know a word called shemale.I had heard that word earlier also when I was 14-15 but didn't paid attention towards that.But that was the day when my life twisted and took a u turn.
Just to have fun I was in sear... Continue»
Posted by hunter043 2 months ago  |  Categories: Anal, First Time, Shemales  |  
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Fantasy Mum and her Bloke

Please excuse my shocking grammar.
My parents split not long after I was born. I lived most of my life with my Dad not even knowing who my mum was. Mid t**ns I was introduced to my Mum. During my late t**ns, due to life and circumstances i was f***ed to move away and live with my Mum.
She tried to play Mum but the reality of why she wasn’t there from birth was quite hard to hide. She had no maternal instincts at all, or any interest in being a parent. Her main Priority was work, and her house. she had a lovely 5 bedroom house all to herself. This worked well to give us space as I was a very... Continue»
Posted by jessicacd1982 2 months ago  |  Categories: Shemales, Taboo, Voyeur  |  
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cant help falling for hot sexy times with married

When i was younger i never got the pretty girls and never functioned down below well and soon became transgendered. I dont have the pressure to perform any more . I was still attracted to girls but one day saw a huge black man with 2 sexy girls and i began to wonder why so many females had black boyfriends. All of my female relationships ended with the girls going to black men so got intrigued.
One day i was out one night in Manchester and was asked by a very tall black man if he would be able to lick and kiss my feet. Instantly i thought that would be lovely. I didnt expect to see his m... Continue»
Posted by Jennifertaylor 2 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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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 2 months 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 2 months 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 2 months 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 2 months 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 2 months 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 2 months ago  |  Categories: Fetish, Hardcore, 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 2 months ago  |  Categories: Gay Male, Shemales, Taboo  |  
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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 2 months 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 2 months ago  |  Categories: Shemales  |  
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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 2 months ago  |  Categories: Anal, First Time, Shemales  |  
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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 2 months ago  |  Categories: BDSM, Hardcore, Shemales  |  
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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 2 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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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 2 months ago  |  Categories: Fetish, First Time, Shemales  |  
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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 2 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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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 2 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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