Shemales Porn Stories
Page 18

Transgender dating advice

13 RULES FOR DATING A TRANSGENDER WOMAN
Greetings, Ariscestocrats!
How are your dating lives? Any single transgender women out there? Not too many, eh? Well, I’ll attest to that being the reason I keep running into the same type of guy. He’s Mr. Uninformed, Mr. Inexperienced, and he has a million questions, none of which have anything to do with who you are, but “what” you are. And it’s not that these men don’t mean well, it’s just that they’re hurting their chances by remaining ignorant to a person that they’re clearly attracted to.
So, if you’re attracted to transgender women, here are a ... Continue»
Posted by holdatduck 5 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 2042  |  
100%
  |  8

Completely Fooled

I could not have expected the encounter I had the other night. Having recently separated from my wife a buddy and I went out to a local pub for a few beers. While we were sitting at the bar deciding what beer to try next a very hot redhead comes over and sits next to me. We exchange hellos introduce ourselves. Soon begin to talk about the different complexities of the beers we are tasting. She is so sexy with small b cups and a perfect mouth. After a few beers my buddy decides to take off leaving Veronica and I to get ourselves. She is just a darling; her smile, her laugh, her sensual demeanor... Continue»
Posted by IndieMe 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 5158  |  
96%
  |  5

After School Dick-tention

I was late for class. Again. I slowly opened the door to my classroom, hoping Ms. Peterson was absent. Just as I managed to open the door enough to peer inside the class, I saw her. She had her back to me, as she was writing down notes for the students to copy, on the blackboard. I couldn't help but admire her form. This was her first year teaching high school history, and she had no shortage of teenage boy admirers. She was tall, I don't know how tall she was bare foot, but in heels (which she always wore) she was taller than most in the school; faculty or student. If I had to guess, I would... Continue»
Posted by SlaveX 5 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6304  |  
100%
  |  3

school teen gay crossdresser first time sex

A young cross dresser's first gay experience
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest for me......they were wrong.

It had been a great afternoon jacking off in my new bra and panties and watching my first porno when it happened, I saw the most beautiful thing ever, Peter north titty fucking a hot blonde and cuming all over her face. I w... Continue»
Posted by allisontranny 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 10951  |  
97%
  |  21

"Just Treat Me Like A Lady" My First TS

I had just moved to San Antonio for a new job. I only knew a few people from work and asked them where I should go for some night life. They told me to go downtown and gave me the names of a few bars. I was 27 at the time, athletic, a little over 6'0" and about 175." I have a good body and dress casually. I went to the first bar on the list they had told me to check out. I walked in wearing faded bluejeans and a tight gray t-shirt. The bar was about half full of men and women and everyone seemed laid back and cool. I sat in the corner booth and ordered a beer. A few drinks in I noticed a stunn... Continue»
Posted by JesseM75 5 months ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1602  |  
100%
  |  2

A Special Little Girl ( I did not write this )


"Your hair is getting so long now." The Mommy says as she smooths
Erin's wavy blond hair down. "I think we should take you to get it cut."

"No Mommy, I like it long."

"Before much longer it will start getting into your mouth when you eat.
It might get annoying. "

Erin thought a moment. His head down, hesitantly, not wanting to upset
The Mommy he says: "But, I like the way it feels when it's long."

"How does it feel, Erin?"

"It makes me feel pretty like you are Mommy."

The Mommy's heart warmed over. She likes it when her son says she's
pretty. I... Continue»
Posted by whiteshadowz 5 months ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 7540  |  
95%
  |  1

The Sissy Gene: Prologue

An amazing study has shown how to weed out inferior men from the age of 16 by identifying a certain gene in the boy's body: The Sissy Gene. This method has shown 100% success rate and has now been implemented as a global law. Promoting world peace, decreasing poverty , increasing employment, and strengthening future generations. The basis of the study is to label certain men as Sissies, creating a 3rd gender below male and female. Whereas men and woman are considered to be equal, Sissies are considered below them, and even in some cases below pets and other domesticated a****ls. In order to d... Continue»
Posted by sissyslovebbc 5 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1280  |  
84%
  |  2

Crossdresser gets help from a stranger



A Good Relationship - Cross-dresser gets help from stranger.
I had just moved into the country to a nice little cottage that my mother owned, she left it to me when she died. I had lived there for a couple of months, and began to feel at home and took to exploring the countryside. Across the lane from my house was a footpath lined on both sides by a tall hedge, it went past a large mansion house, which was the only other building for miles. The path led to a small wood which I thought I would investigate at some time.

My name is Ian I was 25 then and loved dressing as a women (s... Continue»
Posted by klammer 5 months ago  |  Categories: Fetish, Shemales  |  Views: 1070  |  
100%
  |  2

my satin shemale evening

It was a usual Friday night. The bar was busy with guys as ever but nothing seemed to stand out this evening. I drank for a while then i got a pat on the shoulder, i lowered my drink and turned to see the most beautiful lady id ever seen. (or least i thought see was a lady)
She asked me if i was alone, to witch i replied yes. after a few drinks we were getting along great she said,
'shall we ditch this joint and head for mine' Winking at me. I thought id hit the jackpot. The taxi ride was long she had a house miles away which seemed to give her chance to keep rubbing my groin and kissing me... Continue»
Posted by satindresser 5 months ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 3130  |  
100%
  |  3

Out in Public

b]Tales of a Crossdresser: Dressed in Public

Author's note: This post originally appeared on my blog, Tales of a Crossdresser. If you are looking for a story with oodles of hot, kinky sex, you better keep looking I'm afraid......Bri


I used the clicking of my heels on the neon-lit sidewalk to keep time with the mantra I was chanting in my head,

“Point the toe, heel first, straight line, swing the hip…”
as I turned the corner of the alley where I had parked the car and onto the crowded Kansas City Halloween sidewalk.

Ok, maybe not really crowde... Continue»
Posted by prairieFreak13 6 months ago  |  Categories: First Time, Shemales  |  Views: 1142  |  
100%
  |  8

Graduation Night for My Sissy Girl

I’m going to give you a special set of instructions to make you feel like a soft, sensuous girl. You love feeling like a girl, don’t you? There’s no other feeling like getting dressed up in pretty, feminine clothes, trying new looks, new shoes, new dresses and skirts, new lingerie, new pantyhose and stockings, new panties and bras, new jewelry, accessories and makeup. It’s so much fun being a girl.
You are a girl. And you want to do allthe things girls do, don’t you? You want to look like a girl. Feel like a girl. Think like a girl. You want to be a girly, ultra-feminine sissy. But you want -... Continue»
Posted by MartyDT 6 months ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 2405  |  
100%
  |  5

bonfire.

One gorgeous spring morning strolling into the kitchen my other half hands me a cup of coffee and says a beautiful weekend for a first run on the bike ,looking over the rim.of my cup smiles a weekend away with you sounds heavily when we leaving finish your coffee I will make you breakfast then we will pack the the bike.
We are ready dressed bike is packed asking him any place in mind he says we will let the bike decide ,the bike comes to life vibrating with anticipation on our destination ,lift my leg straddling the bike wrapping my arms about the Mr.
Driving the road to know where we have b... Continue»
Posted by chocolatelace 6 months ago  |  Categories: Shemales, Taboo, Voyeur  |  Views: 776  |  
72%

Sissy School

Chapter 1: Welcum to Sissy School
Dear Diary,
My name is Aaron Antony, 18 year old bi curious male. For the past month I have been seeing another man, his name was Geroge but he preferred that I call him Daddy. I never thought of myself as being completely Gay, because I would still find girls attractive, and Daddy knew this which was fine by him. But one day at the beginning of summer time Daddy suggested I should go to a special school for 4 months, a place where other boys confused about their sexuality could go to find themselves. Daddy said it was a gift from him to me, and that he wo... Continue»
Posted by sissyslovebbc 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3149  |  
100%
  |  10

A New Day (MFF, trans, LP, cons)

Normally, Patrick couldn't remember his dreams. There were vague after-images of things, people, places, but nothing really coherent. Instead, he recalled emotions. Fear, anxiety, happiness. Sometimes, rare times, he realized he was dreaming while the dream was unfolding, allowing him to take control of things. Those dreams were the shortest, as if his mind didn't want him directly connected to his subconscious. So as he woke that morning, he wondered exactly what it was that was happening. Was he dreaming? If so, he could do something about the strange sensation he was experiencing. ... Continue»
Posted by Spectreofhell 6 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 615  |  
100%

Daryl Wants Me Girly. Another story.

In my last story Daryl wanted me to be a slut for him. It was an awesome experience and Daryl was really great at making me feel the part, the way he swore and bossed me. And the way he shagged me like a rag doll.

But Daryl has many moods as I discovered when he said he would call me his girl Jackie - with the very tight ass and slender figure, wrapped in a hugging black silk dress which he pulled out of his role play wardrobe.

He wanted the whole caboose, the black and red underwear, suspender belt and black stockings which truly made me feel the part. Simply putting them on made me fee... Continue»
Posted by Yoav_Roth 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 782  |  
100%
  |  1

the library

Thursday hubby burst through the door smiling honey have some exciting news as he kisses me he then tells me we are leaving for the weekend ,we have been invited to a masquerade ball ,we leave Friday after work here is my card get what you need .
Friday morning arrives I am.excited I jump out of bed ready my self for a full day of shopping ,the day is almost over hubby is due home shortly I head for the shower stripping as I go leaving a trail of clothing behind stepping into the shower washing my hair I fail to here hubby walk.into the shower ,he whisper hello honey I am I turn to face him.s... Continue»
Posted by chocolatelace 6 months ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 2049  |  
100%

New Control

I'm no stranger to the concept of chastity and orgasm denial / control; but recent events have really opened my eyes to it and I now feel I can speak about my experiences with it now having been subjected to it for an extended time. Unlike my previous experiences with being controlled through chastity, this time I feel well and truly broken -in a totally submissive way. I had believed that my time with it before was all there was to it as previous lovers and Owners had locked me up from time to time in an effort to establish more control over me. Now my current situation has me at a whole new ... Continue»
Posted by LaArana 6 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1741  |  
100%
  |  2

My first steps ---- / My second time. Misha /

Hello dear readers. More recently, I quite casually come here, read the stories of many of the authors in this issue and, if not original, also decided to share with you my story. Of course it will not be very different from the others, but it will be supported by my photos, and you can get an idea about me. My story is absolutely true and real as myself. I just changed it in minor details (names, places, and events), but otherwise, everything that I have outlined here - happened to me actually.

Before you start reading my story, I recommend you visit the page "My World" on «mail. ru »at m... Continue»
Posted by aleksandr40 6 months ago  |  Categories: Shemales  |  Views: 1215  |  
33%

My second time. Misha

Once in the middle of June last 2013, I first give the man a half months have passed. Transgressing the line because of which there is no return, I learned to live with this new idea, the thought that I was fucked. Experienced by me that night forever changed me. Conflicting feelings overwhelmed me: on the one hand - I could not believe that I still decided on this, on the other - somewhere in my town lived a man who ****d me, and I liked it, despite all the confusion of the meeting and small penis size of my first lover. Losing virginity and realize the seriousness of this event, I was fright... Continue»
Posted by aleksandr40 6 months ago  |  Categories: Shemales  |  Views: 342  |  
50%
  |  1

Gina C

A number of years later, after my first shemale expereince, I still had a penchant for a hot shemale or a slender sissyboy who was passable. That's when I met Gina, who fit the mold of a slender sissyboy who was much more than passable, she was gorgeous.

The first time we got together was on a rainy Sunday afternoon. My wife was out of town and I was cruising aroind on AOL in the SoCal Shemales chatroom. I came across her screenname and we started to chat. We traded writen descriptions of one another and she sounded very hot. She was white, in her late 30's and was married like me. Sh... Continue»
Posted by Blackpapi65 6 months ago  |  Categories: Shemales  |  Views: 1668  |  
100%
  |  2