Shemales Porn Stories
Page 62

My Early Crossdressing

I started cross dressing around 12. At first it was knickers or tights. As I got older I started to get more serious with it. Just after I turned 16, I'd often go out round the streets round town dressed in full girls clothes. I'd always prefer going out late in the evening in winter, as I'd not pass many people and id normally only pass a few cars, some would slow down as I walked along the side of the road.

One day I was home alone, my parents were away for the week and my s****r was staying with her boyfriend. I turned up the music and got dressed from head to toe. I was pretty much smoo... Continue»
Posted by VirginAsAGirl 3 years ago  |  Categories: Gay Male, Shemales  |  
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The Arrangement





My wife and I have been married for 10 years and are very much in love but we do have our own little fantasies as we have learned over the years. She is 5'8" tall, blonde hair blue eyes, in my mind, quite a sexy body, with great legs, a nice ass, and ample breasts. She really looks pretty hot.......when she wants to. As for, me I am 5'10" about 165-170 lbs, and as her I have blonde hair and blue eyes. I have a fairly nice build, having been a collegiate athlete and still in ok shape.

That being said let me set the scene for what has taken place in our lives. Early in our marriage w... Continue»
Posted by lonicd 3 years ago  |  Categories: Fetish, Shemales  |  
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I Told You

“No, please…” I barely audibly whispered.

“Shut up you little cum whore!”

“So... ohh god, no... Fuuuuuuuck,” the words leaked through my painted lips.

“You want that hole filled too, you little cocksucking bitch?”

“No, please! God, just stop please…”

“You’re so ready… I told you you’d be my bitch,” she taunted.

Of course, there wasn’t much I could do to argue with her. Regardless of the obvious physical advantage I would normally have over her, there was the small problem of being helplessly slung over the side of the couch with my hands bound tightly behind my back, while he... Continue»
Posted by Femluver 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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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 2 years ago  |  Categories: Fetish, Shemales  |  
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Cock In The Coffee Shop



So anyone who has got to know me on xhamster knows I love the "3 c's"; Chocolate, coffee and cats. Well, to be fair it's four c's and the other is cock, though it's more a lust thing rather than love.
I only mention this as a recent event led me to consider removing chocolate from the list and replacing it with a rather beautiful and perfect cock.

My adventure begins in "guy mode" in the little town square over the station bridge from my house. I was originally going to meet a friend in sainsbury's and get something to eat but she cancelled on me and I'd already left the house, so I th... Continue»
Posted by KitsuneTV 2 years ago  |  Categories: Shemales  |  
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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 11 months ago  |  Categories: First Time, Shemales, Taboo  |  
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The Intimate Dinner Party

Susan and I were filled with anticipation as we arrived at Victoria’s house. We had been invited to what the written invite referred to as a “Sexy and Intimate Dinner Party”.

Victoria was renowned for her unusual, and always different, dinner and cocktail parties. She certainly did not like doing things the way other people did them. You never knew what to expect, but you always enjoyed them and could say that you’d had a new and exciting experience.

My wife, Susan, was looking incredible. She had a short black skirt that really set-off our beautiful long legs encased in sheer black sto... Continue»
Posted by didi_galtier 3 years ago  |  Categories: Group Sex, Shemales  |  
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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  |  
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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 4 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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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  |  
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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 29 days ago  |  Categories: BDSM, Group Sex, Shemales  |  
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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 2 years ago  |  Categories: Anal, Mature, Shemales  |  
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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  |  
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Amsterdamned

At what age it can be definitely classed as that, is for lawmakers and
judges to decide. UK law is clear but not always a realistic guide. For
reasons of shame or guilt many gay or trans youngsters have found that
casual sex with much older adults was the only discreet way of exploring
their own sexuality, before they felt ready to step into the more
familiar minefield of emotional relationships with people nearer their
own age.

An age-limit there must undoubtedly be, and obviously for the protection
of vulnerable young teenagers it has to be rather a blunt tool. But many
adults (an... Continue»
Posted by klammer 2 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
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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 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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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 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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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 4 years ago  |  Categories: First Time, Masturbation, Shemales  |  
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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  |  
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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 3 months ago  |  Categories: First Time, Shemales  |  
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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  |  
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