Shemales Porn Stories
Page 67

What does it mean to be a sissy?

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.

Sissies are transvestites who can’t be sated by just throwing on some panties and jerking off. They must strive to bec... Continue»
Posted by fatimaait 11 months ago  |  Categories: Gay Male, Shemales  |  
1853
  |  
89%
  |  8

Weekend with Kelly, my new lover, part 7

This is a story about the LOVE of my life, a T-Gurl whom I'm
gonna marry someday soon.


I sat at the table while Kelly finished making breakfast.Kelly
waked in with a plate that had a breakfast burrito, sausages,
toast and a carafe of coffee.


I asked her where her plate was. She said, this plate is all
mine, picking up one of the sausages, sticking it halfway
in her mouth, stroking it in and out while licking the underside
with her tongue.


I went into the kitchen, fixed myself a plate. When I turned
around, she was right behind me. Grabbing my shorts and
yanking them down... Continue»
Posted by Bigrodtaz 1 year ago  |  Categories: Anal, Shemales  |  
1850
  |  
50%

bookstore sissy slut

My name is dollie I love to be a girl and being very petite and pretty long black haired its easy for me too feminize. And until now I wouldn't go out, dressed up, sometimes a quick walk around or a short drive but nothing real. And one time in college I walked around the campus. Anyway I ignored all the signs being overly sensitive for a boy It should of clicked when I was diagnosed with disphoria. I knew I liked being girly but I really thought all teen age boys were like me. Always being a pretty-boy girls always came my way but they all end the same I get hurt because just like a girl ... Continue»
Posted by dcdollie 3 years ago  |  Categories: Fetish, Shemales  |  
1849
  |  
93%
  |  5

Wife does a Blow Bang

What a night, ended up at Pandora’s Box a local strip club for a few drinks, Lynn (my wife)is an ex dancer and enjoys the entertainment and hot chicks at the club, she actually gets more attention than I do. We only had time for two drinks and it was last call, as we were leaving Jason doorman stopped us and ask if wanted to burn a joint. We decided it would be all right because he wasn’t really a stranger as he always was at the door when we went there. He said he would be out in a few minutes.
While we were waiting I tried to convince Lynn that we should have a threesome with Jason. She sa... Continue»
Posted by jm6060 2 years ago  |  Categories: Voyeur, Hardcore, Shemales  |  
1850
  |  
100%
  |  1

So hard so big hoooffff

Hello my friends. I realised u liked my diary. ((Please excuse my writing mistakes and English))
I went trough of a lot of memories, good and bad, nice and ugly ,
but most of the memories of that time is about how to make someone's happy.
After my fathers start to see me as a girl ,who can satisfy him in lots of different ways.
Slowly slowly I get use to it . To how be a good girl for him and how to quickly in different places specially in public places make a cover up story or cover my naked body for good.
I loved my father and my female part. Drawer full of panties and bra shelf f... Continue»
Posted by Echoes90 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
1849
  |  
100%
  |  1

Portuguese Summer part 1

i`m not tall, in fact for a guy i am quite short at just 5ft6in and very slim for a guy as well weighing in at just over 8 stone, so girls friends have been a little hard to come by but i have had a few over the years, 2 in fact but one of those was when i was 14 the next one came 3 years later.
So now at 18 years old i am jobless and without a girlfriend and its just coming to the summer.
Paul is my best friend he is from a well off f****y and he turned up at my house one day in June and asked if i wanted to head out to Portugal with him for the summer, His parents had a 2 bedroom villa out... Continue»
Posted by julieanneff 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
1847
  |  
100%
  |  2

Sabrina and the Black Quarterback

Part I – The Encounter

I've been a crossdresser since my early teens. I'm a 5'3”, 28 years old, 130 lbs, latina sissy. I have long black hair and green eyes, with a dark silky brown tan and very athletic figure with a big ass and small tits. I love feminine things and have always had an intense desire to be a full time girl.

Whenever I'm home, I always wear women's clothes. I just love weekends because I transform into a very sexy and exotic girl. Every Saturday morning I get up early and exercise. I always wear an 80's workout outfit, white tights and a sexy bright-colored spandex leot... Continue»
Posted by mspetite 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
1846
  |  
100%
  |  6

Becoming sissy Jenny Part one

Hi, my name is Jonas and I´m 25 years old. This is the Story of how I became a sissy. So actually my name is Jenny now. But lets not get ahead of ourselves. The story has a slow build up, I hope it´s interesting for someone. Thats part one, I will continue the story from time to time. Everything sexual in this story happens to people over the age of 18.

I guess it all started whit my mom being a gold digger. One of those women who have a pretty face and a nice body and try to make a living out of it. After a few years of being an e****t, getting to know people, sucking the right dicks, gett... Continue»
Posted by jenny42 9 months ago  |  Categories: First Time, Masturbation, Shemales  |  
1846
  |  
100%
  |  2

Art Student

It was the beginning of the semester at the Art Institute and I was pretty excited about my new schedule. Professor Ludovian always brought interesting nude models to his classes, and his tips on how to draw the human body were most useful. I had learned a lot in the intermediate class but now in this advanced class, I knew the professor was going to be more demanding.
Ludovian greeted his students with a grin and a wave of his extremely thin and graceful hands, the hands of a maestro, someone who had mastered the art of drawing the intricacies of the human body. "Hi Daniel, good to see you ... Continue»
Posted by latinCharm 3 years ago  |  Categories: Anal, Mature, Shemales  |  
1845
  |  
100%
  |  9

T-Girl at the bus stop

The radio was loud and the top was down when I first saw her.
She looked so beautiful sitting there at the bus stop.I remember her legs, they were long and tan and clad in silky smooth thigh highs. Her skirt shifted when she crossed her legs and I could see the garters clinging to her tan skin. She turned her head and smiled at me while I waited for the light. Her eyes were so bright. I think they were green, maybe blue. Every movement she made seemed to beckon me. As if she was calling me to her.

I couldn't help but stare at her tits - they were fabulous. A car behind me honked. shatterin... Continue»
Posted by shemalefckn 4 years ago  |  Categories: Anal, Hardcore, Shemales  |  
1844
  |  
89%
  |  9

My Friends House Part 4

I could see that she started moving. I tried to hide by the foot end of the bed. It got quiet again. I’d better try to get out now. I came to my senses and it was enough now. I tried to take my clothes off that I had borrowed from his mom. I took off the jacket, and was just about to take the wig off, when I heard her moving in the bed again. Now she was facing towards me, but I thought she was still asl**p. I was standing in his mom’s white pantyhose, in heels, bra, and her wig. My cock started to move again.

‘No!! Not now!’

I pulled my cock out and started playing with myself in front ... Continue»
Posted by HosieryQueen 2 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
1842
  |  
100%
  |  4

Just Like Being Girly For A Man


I've just been thinking how nice it is for a sissy to be able to be in the feminine role with a bf. I'm lucky in that regard in that my bf likes me to be girly and I really like to be girly for him. nothing like being the soft feminine girly boi that I am and being in the passive roll when being made love to. being the receiver and not the giver in the penetration. course sucking his cock is also pretty girly isn't it?

my sissy pussy just loves the feel of a hard cock entering me and the the slow movement as he penetrates me further, then feeling him completely inside me. laying on my bac... Continue»
Posted by sissygirl 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
1838
  |  
100%
  |  25

sissy blackmailed, gang banged, then ruined.

*This is my first story ever, I have no writing background whatsoever, in fact I failed every English class I ever took.. This is simply my fantasy, with a little bit of my real life experiences mixed in here and there. Parts of this story may be sadistic and extreme.
My apologies if the story is a little s**ttered.. You will just have to deal with it! :)

Please be kind, but honest and let me know what you think.


Chapter 1
The beginning.


Buzzzzz, buzzzzzz... My cellphone vibrated on the night stand beside my bed. I groggily felt around in the dark until I got... Continue»
Posted by submissive_boy1990 5 months ago  |  Categories: BDSM, Group Sex, Shemales  |  
1840
  |  
88%
  |  2

My Ultimate Fantasy...

Let me start with the details...

I'm straight, 21 years old, and am probably no more than 7 inches long. But if I may say so myself...it's a perfect cock, thick and veiny and almost always pulsing. I have always loved my cock, and rather recently I began to realize that I could no longer stop at just mine.
The more I watched facial vids, the more I focused on how hung the guy was and how thick his lines were. Now, I'm a fit guy. Work out daily, I think I have a pretty sexy body as far as gentlemen go. But, I simply don't think guys are attractive.
But I have this compulsion for cocks! I... Continue»
Posted by reddyforyou 5 years ago  |  Categories: First Time, Masturbation, Shemales  |  
1837
  |  
97%
  |  3

Moonlight ride


I take a deep breath and open the door, it's a summer night, nearly dark. The street is quiet, dumb to the scandal about to unfold. I doubted anyone would recognize me, in my short fur coat, denim mini and trademark purple heels. Not unless they were a fan anyway :) I just need no-one to see me leave the house, once a few yards away, I could be anybody.

The coast is clear, I step out and shut the door as quietly as possible and walk away from the house, praying I don't activate the neighbour's floodlights. As I clear the first few houses, I relax a bit and a thrill runs through me. I... Continue»
Posted by christinasucks 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  
1836
  |  
77%
  |  9

Stefan's Blackmail

When I was about 19 I started to crossdress. I didn't have gay feelings or strongly identify as feminine but I felt strangely attracted to my older s****r's clothing. One day I tried on a skirt and I found this simple act feel so thrilling that at the next opportunity I tried on a two more things...a dress and and a pair of her jeans. I was always thin, especially when I was younger, and my s****r was only three yeas older than me, so I had little problem fitting in most her stuff. Actually the stuff at the back of her wardrobe, the stuff a year or two old that she didn't really wear anymore w... Continue»
Posted by tricked-sissy 8 months ago  |  Categories: First Time, Shemales  |  
1834
  |  
100%

Father Knows Best

“Dad,” laughed the 37 year old high principal when his father answered.
“My man,” replied the 56 year old small town chief of police. “What’s happening?”
“Not too much, pops. Just making it. It’s been hectic around here lately.
George replied slightly confounded because he never heard his son speak in such a manner, “Oh yeah? “Everything good with you and Candace? How are my grandk**s?”
“Yeah. We’re fine. The k**s are good.” Jerome fibbed. “It’s just a combination of work and normal shit.”

“I hear you. Sounds like you need what the white folks call a ‘mental health day’.”
“Wish I could... Continue»
Posted by faggyboi 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
1833
  |  
100%
  |  4

My sissy son,by his dad and lover. Part 2

Hi,thought it was about time i let you know about my son and me.

This is Part 2.

So...there i was,on my knees staring at my son's beautifull cock. Not big,only 4" long..but sweet with a nice head and completely shaved..(or waxed). "Oh Jack...suck me please...pleeease...been ages since a handsome older gentleman touched me there." Pre-cum was leaking from it...and i licked the end...and gently took him into my mouth! He moaned and slowly made his hips go forward and back...gentle movements like he was fucking my mouth.I was sooo horny at this point i would have done anything...so i did...... Continue»
Posted by chocandres 4 years ago  |  Categories: Anal, Shemales, Taboo  |  
1834
  |  
99%
  |  7

The Adventurous Couple

"Whose ass is this?" Nancy screamed at me as she had me bent over the edge of the bed and fucking me in the ass with her 8" strap-on dildo.

"It's your ass Mistress; it has always been your ass!" I replied through gritted teeth.

Earlier that evening, my loving wife, came out of the bathroom with her jet black hair pulled back into a bun and wearing black rimmed glasses, letting me know she was in the mood to dominate me. She was also dressed in her shinny black teddy that pushed her large milky white breasts together, causing her cleavage to look even deeper than it already was, and her... Continue»
Posted by heatround01 3 years ago  |  Categories: Shemales  |  
1830
  |  
100%
  |  14

Two Gurls and a Guy

I know you had a long day but do you mind if I invite a girlfriend over tonight, Celeste asked? Of course not babe I am just going to chill upstairs with a book tonight. Who is coming over? Just a new friend Carmine I met at work. Cool I replied as I finished dinner and headed upstairs. Kicking back on the bed half asl**p and deep into a novel I heard the doorbell ring, some chatting a wine cork and the back door slider. At some point I must have dozed off and awoke startled with Celeste in a black see thru silky nightie rubbing me thru my sweats and kissing my neck. My cock begin to stir as I... Continue»
Posted by iheartm2f 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
1826
  |  
91%
  |  2