Shemales Porn Stories
Page 4

Russian Shemales 2: Electric Boogaloo

The next Friday, Serge and I take bus into the city again. He was very anxious to be there and to get pretty again. I am just anxious.

Friday night is much like the previous Friday night. We move furniture, and build set, and then smoke cigarettes and drink vodka. Saturday is again the same: We are showered, and painted into pretty ladies. We take turns posing for camera in bras and panties and slips and stockings and high heels. We are both getting better at walking in heels. (If you search "Russian Shemales" in photo gallery of XHamster, you may see some of our photographs.)

But... Continue»
Posted by TransContinental 1 month ago  |  Categories: First Time, Shemales  |  Views: 296  |  
100%
  |  2

Mommy Has A Cock

I want to sing to the world about my beautiful wife
Perry. Fuck anyone who questions true love between men.
A wife with a cock is better than one with a cunt any
day. Perry is so sensitive and worships my cum filled
cock with his cock sucking mouth and his tight brown
ass hole.

He is so beautiful dressed in his short red party
dress, black thigh stockings, leather high heels and
make up. His hair is shoulder length and he is prettier
than most women. I demand that his soft body is shaved.
I am demanding and he loves me for taking charge.

The only thing needed to compl... Continue»
Posted by 1superhornyguy 1 month ago  |  Categories: Group Sex, Mature, Shemales  |  Views: 2215  |  
32%

T-Girl Obsessed

You now know that I have a
thing for T-Girls. Ever since I experienced that first
mouthful of cock on a female Amazon body, I can't get
enough. I don't consider myself queer or even bi-
curious. The thought of all out sex with a man doesn't
interest me at all. I have had my cock sucked at the
local porn shop, but I never gave back.

Anyway back to the main story. My first encounter with
a shemale got me hooked. My next chance was about sex
months latter. The rest of the f****y went out of town,
so I was home alone for the weekend. I called my
shemale heart throb for an app... Continue»
Posted by 1superhornyguy 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1096  |  
100%
  |  2

Joe, Chrissie and, Paula

) I don’t know why I need to get all dressed up, it’s you he’s coming to see.
I know, but I like to see you looking sexy and I’m sure Joe appreciates having a sexy woman watching.
Anyway, you finish off and I’ll make sure dinner is OK.
It would be the second time Paula had met Joe, the first time she was only there to take photos, not taking any part in proceedings.

How does that look Paula?
Yes, you look good, very tarty though, I can see your stocking tops
I know, but he likes me like this. Oh,Oh, that’s him now. Will you go?

Paula lets Joe in, greets him with a kiss and when he ... Continue»
Posted by chrissie28 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1170  |  
67%
  |  1

a work in progress...

(a collaboration with @lizreed... would love to get this started with her again...)

...<i>In medias res</i>...

....fantastic Kate ... I'm all about your lips at the moment. Incredible!

these lips would love to be all about you liz.... plump, soft, supple, tender..... great for soft kisses.... butterfly kisses.... french kisses... kissing a neck... moving around and nibbling an ear... and kissing the sides and nape of a neck... and maybe for whispering into an ear.... delicate whispers of things to cum...

...i imagine sitting with you late at night in a very dark bar. as we get up... Continue»
Posted by naughtykate13 1 month ago  |  Categories: Shemales  |  Views: 146  |  
100%

Rainy Day Transformation

Prelude
I was driving into Boston to see my GF. We were both graduate students but at different colleges. I was staying in her dorm room and there was no hassles at all. Other guys stayed there with their GFs. We had been steady for about 3 years. {I did not know she was cheating on me}. I was 30 years old, thin , petite with real long hair. My GF K. often brushed it and put it in barrettes. I am about 4 inches and she said it was too small for her and she called it her, " little man". Our sex life was slow and good for me but not he... Continue»
Posted by robin48 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2816  |  
100%
  |  4

Not Your Average e****t pt1

There was a knock at the door. I got up and walked over, checked the peephole first, saw it was a woman and opened the door. She was at least six feet tall, had long raven black hair, pale skin, deep blue eyes and smallish but perky breasts. Her nipples showed some through the fabric of her short, hot pink dress.
“Hello. May I please come in,” she asked with a nearly perfect smile. I stepped back, pulling the door open wide, swinging my arm in a wide arch waving her in. As she walked past I could smell her vanilla scented perfume. Her little pink dress was stretched tight over her firm, ro... Continue»
Posted by TheHumanoidTyphoon 1 month ago  |  Categories: Shemales  |  Views: 1223  |  
100%
  |  9

Surprise surprise for the babysitter

It was September of 2009 and I was coming home from my high school when my mother called me with the details.

“Hi mom, what’s up?”

“Lex, you remember the Jones’ right?”

“Sure, they have the twins right? How old are they now?”

“Well, I think they just turned twelve last month…but anyways, Mrs. Jones just called me not ten minutes ago to see if you could head over to spend the night. They received an emergency from the hospital where her mother lives and they need to leave now and they cannot take the k**s with them.”

“Wow…uh, sure, I can head over. They’re in the new part of the ... Continue»
Posted by 6270daniel 1 month ago  |  Categories: Anal, Shemales, Taboo  |  Views: 17496  |  
69%
  |  4

The Origin of Sgt. Steel Part 2: Iraq, Internet Po

For a long time I skated around the periphery with my attraction to shemales and fembois. After my initial exposure watching Jaye Davidson in "The Crying Game," I went back to living with my soon to be future ex-wife and my two stepdaughters.
I didn't really start considering shemales and fembois until my second deployment. In August 2007 I arrived in Iraq. Although I have been in the military for over thirty years, I’ve never been one of those gung ho types. To be honest I’m more of a cynic. Kind of like a character named the Comedian in a movie called Watchmen. He looked at all the serious... Continue»
Posted by sgtsteel 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 1332  |  
89%
  |  4

Poker Night Part 4

I wake up the next morning, dried cum on my face. It was already a little later than usual. Mistress and Master come into my room. "Is my little sissy all ready for a big day today?" She said. I bounced up and down excitedly, giggling at her every word. "My goodness Craig! You couldn't even clean her up after you came all over her precious face?" "I was tired, and I'd thought it'd make her sl**p easier." He said. "Is he right sissy? Did having real man cum on your cute little face help you sl**p better?" She asked. "Yes Mistwess, having Massa's cum on my face put my fas asweep" I responded. "W... Continue»
Posted by ConvertedGirl914 1 month ago  |  Categories: Gay Male, Shemales  |  Views: 707  |  
83%

Tranny tricked the Postman

A true story…

I’d woken earlier than I’d wanted for a rare day off from work and decided to see if I could have a little fun.
So I did my make up and found the longest false lashes I had, touched up with the darkest mascara there is… with a touch of glitter… bright red lippy, a naughty smile, get the picture?

I put on some sexy underwear and a black lace top, little skirt with heels and hold-ups… I was on the hunt for cock but how could I trick a complete stranger into some naughty fun with a horny tranny??… I had a plan…

I was expecting a parcel in the mail that was too big for the... Continue»
Posted by JoanneCoxTV 1 month ago  |  Categories: Shemales  |  Views: 5513  |  
100%
  |  4

Lucy and Emma Part 1 (Friday night fun)

Please go easy on me this is my first story


Ians Journey home home was much more rapid than normal somehow the excitement of his holiday week ahead had put a little extra zip in his step, so by the time he got home they was no sign of his girlfriend lucy which wasn’t out of the ordinary as she normally got home later than he did most nights.

With the house empty he decided to draw himself a bath not something out of the ordinary in fact is what he did every day but his friday baths were special as it marked the first step of his transformation from dull professional weekly Ian t... Continue»
Posted by Chloe_ 1 month ago  |  Categories: Shemales  |  Views: 1362  |  
100%
  |  2

A Warm Cum Bath, on Sara's Hen Night

Part 1. The Meeting with Alise

No one can say that Swedish girls can't attract attention, especially on their last night of freedom, on the eve of their betrothal, some will be found d***k, and some found stripped nude, and even some having a last minute sex with old boyfriends and so on, but one, only one had the experience, most girls cream their knickers thinking about, and this is her and her e****ts account, of her wildest fantasy come alive, the night 200 men ejaculated onto her, boys and men alike, all strangers, doing what men like to do to a beautiful blond 18 year o... Continue»
Posted by MarieL 1 month ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1920  |  
100%
  |  4

Russian Shemales

(Translated from the Russian)

We lived in small village, no work, nothing to do but smoke all day. Friend Serge and I sitting by road one day, when black sedan, shiny from city stop near us. The man inside wearing a expensive suit, and ask if we want jobs as models.

Serge and I think must be joke. But man introduce himself as talent scout. He speaks Russian but with accent I don't not know where from. He says he is from modeling agency and is looking for new talent to model. Introduces himself as Mr. Aronoff, and asks us to stand and turn around. Looks closely at our faces. Serge... Continue»
Posted by TransContinental 1 month ago  |  Categories: Shemales  |  Views: 1649  |  
100%
  |  4

Young sissy loses her virginity (true story)

So this is a true story about the 1st man that I ever met. I was about 13/14 years old and had been talking to a much older man over the internet. He was about 50 if I remember correctly.

I had been dressing in my mother’s underwear and dresses for a few years and found it so sexy, I had not considered myself gay or bi, I just knew I belonged in female attire, it made me happy and felt natural.

The thought of pleasing this man made me excited, terrified and scared, but very excited. I could tell from my little clitty. After chatting for a few hrs he wanted to meet me?

I had never me... Continue»
Posted by Subtvnicola 1 month ago  |  Categories: First Time, Shemales, Taboo  |  Views: 6712  |  
100%
  |  5

Straight, to Bi, to Gay, to Trans, to Straight (Pa

I don't want you to think we simply lived happily ever after. Nothing is that simple.

We've had our ups and our downs, and our ins and outs. We've had three major hurdles, so far. The first was me freaking out over the idea of having a boyfriend. As natural as it seemed to be with him, and as mind-blowing as the sex was, it was still a huge shift in thinking for me. The second hurdle was coming out.

The third was his affair. But more on that in a minute. As I want to talk first about coming out. Friends and f****y may say they support gay rights and all, and they may be fans of... Continue»
Posted by TransContinental 1 month ago  |  Categories: Gay Male, Shemales  |  Views: 1721  |  
100%
  |  6

Jeremy's School Bully

Jeremy hopped off the bus in front of his new school. He lived close enough to walk, but had decided to ride the bus instead. He wanted to see what it was like, because he'd never rode the bus at his last school, he had always walked. The school was a hulking sandstone building that loomed over the small front lawn like some mid-evil wyvern, gobbling up c***dren every morning only to puke them back out onto the lawn in the afternoon. Over the years acid rain made long dark streaks of black and brown down its façade making it look as if Mother Nature had raked it with her claws. It was a post w... Continue»
Posted by test2012 1 month ago  |  Categories: Shemales  |  Views: 2383  |  
100%
  |  4

Portuguese Summer part3

After that night with Alan and the girl back at the villa i was very nervous about going back into work the next night , i was just not sure how much he had felt while he was fucking the girl with me under her or even if he was aware of what happened. When he turned up for work at the bar about 20mins after me he pulled me to one side and just grinned at me and asked if i had enjoyed it
I sighed with relief and said "yeah it was great fun,he just grinned again and said ok ...well if we ever get the chance lets do it,ohhh and i saw her give you her thong as she was leaving and i saw you puttin... Continue»
Posted by julieanneff 1 month ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 999  |  
100%
  |  4

Portuguese Summer part2

I have been in Portugal now for 2 weeks Paul has phone to say he wont be coming out for the rest of the summer as his dad is in a bad way , His mum has asked if i will stay in the villa and look after it for them until the end of august, of course i said yes, but i was getting bored and needed to get some work as the little money i had was not going to last long.
Since Paul went back home i have discovered that i love to dress up in his s****rs clothing that she has left here , and boy has she left a lot of stuff, I have full shaved my body and have started to become quite good at putting on ... Continue»
Posted by julieanneff 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 2471  |  
89%
  |  4

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 month ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1836  |  
100%
  |  2