Shemales Porn Stories
Page 18

The Sissy Gene: The Preparations

***PLEASE READ***
TO FULLY UNDERSTAND THE WORLD OF THE CHARACTER I AM WRITING ABOUT BE SURE TO READ MY PROLOGUE AND "THE TEST" THAT CAN BE FOUND ON MY STORY POSTS AND BLOG RESPECTIVELY. THANKS




THE Preparations

As soon as I entered into my classroom, the teacher started clapping. Congratulated me on becoming a sissy. She was just catching the class up on how she was ending class early so she could help me and the other sissies be ready for the ceremony. After I followed her to the change rooms where the other 3 boys who had just become sissies should already be getting ready.
Mrs.... Continue»
Posted by sissyslovebbc 5 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 364  |  
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Sissy and her Mistress

"Mistress, what are we doing tonight? I need to know what to wear" I pout.
"You'll see. Put on your slutty schoolgirl outfit with your white thigh high stockings, and your 4 inch heels. I'll be there in a half hour"
"Yay! I love that one!" I exclaim.
"Be waiting outfront" you command.
"But Mistress..."
"No butts sissy, this is what you want - and oh, yea, don't forget your plug. The large one"
"Yes mistress"

40 minutes later, I am outfront of my apartment complex trying to hide in the shadows. Given my height and the heels, I am attracting a bunch of attention. You chuckle as 3 black... Continue»
Posted by drew1207 5 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 930  |  
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My 1st time having sex with a guy!!

I went out with a gay friend of mine hem was my hairdresser Rodney he is fine as hell ripped stomach sexy body big fat cut shaved cock,he. Be out for cocktails at a gay bar after about five drinks apiece we started dancing mingling with people I met a beautiful TS lady boy he look & acted just like a girl we was dancing dirty I was getting so turned on she was grabbing my dick kissing my neck talking dirty and it was working so we,went back to,the vip room and was making out she had just un button my pants was stroking my cock so,go... Continue»
Posted by Cockriider69 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2918  |  
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PartyPlanning Chp1. Pt1.

Sarah...


"This feels great. The sun is not to hot on my skin but it's a bright clear day, the ladies are running like clockwork and so am I. Ten, I think ten moms have strolled by, just like yesterday. I'm so glad I decided to workout in my garage. Chicks love to see a man workout, especially a single guy like me. Last minute of my work out and this new workout DVD "Get Slim 4 Fem" Has me in top shape. And the host, Princess!, her highness. What a bitch but if I could fuck her I'd never stop. Last minute gotta focus...

10 m... Continue»
Posted by cohonjames380 5 months ago  |  Categories: Sex Humor, Shemales, Taboo  |  Views: 2461  |  
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My Girlie Fantasy part 3

Suddenly among the Eden of pleasure Ken was providing, the
doorbell rings like thunder as lightning strikes burning away the
sacred garden. Ken curses under his breath while he gets up to go
see who it is. I quickly sit up & fix my clothing as he walks to the
door, watching him as he goes. Almost as soon as he disappears
around the corner he returns proclaiming that it is his b*****r that
he hadn't seen in years then disappears again to let him in. I feel a
bit of a chill roll down my spine as I hear the door open & them
talking loudly. I stand up as Ken walks around the corner with... Continue»
Posted by multiplierx 5 months ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 655  |  
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Return Visit to My Favorite Dr.

Finally the day came for my return visit to the Dr that made me look pregnant & I can't wait. I decide to wear more seductive undergarments this time to maybe get my cute Dr a little more worked up. I wear a matching red & black lace lingerie set with the same shade of red lipstick. I put on a little black dress & some red heels before heading out with an empty bottle in my purse in anticipation for his excessive load. I get to the Dr office & check in like I did before & begin the long wait till I'm finally called back. The nurse does some quick standard checks then leaves me to wait for the ... Continue»
Posted by multiplierx 5 months ago  |  Categories: Fetish, Shemales  |  Views: 957  |  
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The Perfect Woman, Plus (Part III) - Happy Rear En

The 3rd and last part of the Perfect woman, plus story... Hope you enjoy it!


When I got home from my second steamy assignation with Amber, the sultry blonde she-male “girl of my dreams,” I found out I’d won ten million dollars in a magazine contest! Of course, I didn’t believe it at first, but when I phoned the company to confirm, they said I was indeed the Grand Prize winner!
My first thought was to call Amber and let her know my good fortune. I called the number she’d given me, but I got an answering machine. Then I remembered that she’d told me to say my name and she’d pick up. She ... Continue»
Posted by freegre 6 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 492  |  
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Shemale Summer

Once again, this is not a story written by me! It was stored in my computer for ages and decided to share it with you. Hope you like it!


One hot summer day, my friend Sam and I were scoping out the babes at our local beach, as usual. I saw this really hot, busty blonde a few towels down giving me the eye.
"Hey, check her out!" I said to Sam. He peeked up from beneath his Ray Bans and shook his head.
"Forget that one," he said. "She's not your type."
"What do you mean?" I said. This girl would be anybody's type—even blind men!
"Just take my word... Continue»
Posted by freegre 6 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3978  |  
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The Perfect Woman, Plus (Part I)

This is the 1st part of a 3 parts story. It is not mine but I hope you like it...


The week my girlfriend Monica broke up with me, I had to fly to New York City for a convention. I must admit, my mind wasn’t on business, and the first chance I got, I went to the hotel bar to drown my sorrows. The bar was fairly empty, which was O.K. with me, since I wasn’t really in the mood for conversation anyway. I was half-way through my first pint of Guinness when the cocktail waitress brought me another glass.
“Hey,” I objected. “I didn’t order this!”
“Relax,” the pretty brunette said. “It’s fro... Continue»
Posted by freegre 6 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 2090  |  
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The Perfect Woman, Plus (Part II) - Bright Lights,

This is the 2nd part of a 3 parts story....


I arrived home in Los Angeles after my steamy, scorching encounter with a magnificently sexy “shemale” woman named Amber, and found my ex-girlfriend Monica weeping on my doorstep! It turned out the “perfect, buff guy” she’d dumped me for was a d**g-addicted, abusive, macho jerk, which is what I’d thought from the beginning! I was exhausted from the long flight and not really emotionally read to deal with a sobbing girl on my stoop, but what could I do? I let her in and we drank hot tea and talked for a long time. I didn’t make any overtures, bu... Continue»
Posted by freegre 6 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 723  |  
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Shemale Stewardess Seduction

Please note that this story is not written by me! It was stored in my computer for a long time now and decided to share it with you. The author's name as well as the site I found the story are not known...


My introduction into the sultry, steamy world of shemales came (and I mean came!) at 35,000 feet, on a plane flight to the Northwest.
I had been working myself to the bone, staying until ten or eleven at night, coming back in at six o'clock in the morning, and I guess the stress was visible. My boss, Terry, a very pretty, sexy lady (who I later found out was a hot-bod t... Continue»
Posted by freegre 6 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3786  |  
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Dutch Transaction

Amsterdam, April and May is cold and wet.

Back when I was there in 1976, there was no way I was going to let the weather dampen my spirits. It was my second visit to this great city so I considered myself a seasoned veteran who was eager to experience all that it had to offer.

On my first visit, I discovered the red light district. Canal Street with its rows of shops and bay windows. In each window sat a scantily-clad lady selling her sexual wares. I found numerous porno shops with their plethora of novelties that I never know existed. I frequented some of the night clubs whi... Continue»
Posted by freegre 6 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 633  |  
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TV Beginnings - Caught by Neighbour

I started crossdressing at quite an early age, 'borrowing' items of my mum's underwear and furtively dressing in them when she was at work. As I was an only c***d, and mum and dad had separated, I had quite a lot of time to indulge my little hobby! I used to love wearing her tights, the sexy feel of them encasing my legs and cock, and the way they made me feel so girly when I admired my reflection in the long mirror in our hallway. I would also wear her big full-cut knickers and doreen bra, and complete this with a lace slip and a pair of strappy heels or mule slippers that I could fit into th... Continue»
Posted by sparkyking 6 months ago  |  Categories: Gay Male, Shemales  |  Views: 2797  |  
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One Fun Physical

As anybody knows,people in the medical field have seen enough that nothing phases them. So I decide one day when I am going in for a physical to go as Raven just for the hell of it. I get there & sign Raven with my real name in parentheses. I sit & wait for my name to be called hoping not to hear my real name be called. As usual I sit waiting for about 45 minutes before the door opens & to my glee, Raven is called. I fallow the nurse back & she does a basic checkup of my vitals & size before telling me the Dr will be in shortly. After a while there is a knock then the Dr enters with a smile. I... Continue»
Posted by multiplierx 6 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 2165  |  
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Last Weekend - Sunday Morning - Being treated like

The satin rug moved ever so slowly exposing my shivering smooth skin as I groggily opened my eyes. It was 7 AM and my master was already up and was uncovering my nudity on a pink silky bed in which we slept the previous night. The chill in the room and the smooth silky slithering feeling of the satin rug, turned on every nerve ending on my body and my sl**py eyes were opening just enough to sense the nakedness and sensuality of my master's well chiseled body and his morning wood glistening and bathing in the sunlight, peeping through the curtains of the room.

The satin rug had just cleared ... Continue»
Posted by tran4mate 6 months ago  |  Categories: Hardcore, Shemales  |  Views: 2969  |  
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Athens Queen

Our last day in Greece, in a taxi on the way from the ferry to the
hotel we'd be staying in before our flight. (Never, never, never,
trust the Greek ferry schedule to get you to Athens in time for an
international flight, always go the day before!) My daughter sitting
next to me, my wife next to her, my mother-in-law and the Greek taxi
driver in the front seat.

We stopped at a traffic light and I looked over. In bright blue and
white neon, the sign in English said, "Cabaret" and then on the second
line, "Athens Queens". My mind wandered. Could it be a drag club?

With a name like t... Continue»
Posted by freegre 6 months ago  |  Categories: Shemales  |  Views: 923  |  
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School Days ( I didn't write this )




Christopher Reilly woke up early that morning and quickly showered
and dressed in his school uniform. He was a freshman at St. Mark's
Academy for Boys, and although his studies were progressing nicely, he was
still homesick. It was November and he had been away from home for over
two months. He had always been an excellent student in grammer school and
from his earliest years had been something of a teacher's pet to the nuns
at St. Stephan's. Boarding school was a new experience, however; he
missed his mom and s****rs and, although he never would ha... Continue»
Posted by whiteshadowz 6 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 2164  |  
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Paying rent

I’ve always enjoyed getting dolled up like a sexy girl ever since I hit puberty. Doing my hair, wearing frilly panties, skirts, painting my nails and doing my makeup. But being a boy that isn’t viewed as proper behavior. Which is why I’ve always had to dress in private. But luckily with the power of the Internet I’m able to express my inner girl. I run a blog where I post dirty pics of myself dressed up, erotic stories of young crossdressers being used by older men, captioning dirty pictures and I do webcam shows just about every night. I even get tipped for my webcam shows and can use the mo... Continue»
Posted by ScarlettMaeBottom 6 months ago  |  Categories: First Time, Shemales  |  Views: 4135  |  
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My girlie fantasy part 2

A few days passed since my heavenly Halloween night with the wondrous morning after & I was so excited at the possibility of meeting up with the stud that took me like a woman again. Since I knew Halloween wasn't for another year I invested in a new outfit so to meet him in. I returned to the bar one week afterwards but he never showed, though several men hit on me I never entertained them at all. The bartender wasn't the same so I never asked if they knew my hunk or not. Disappointed I went home but was motivated to keep trying. Realizing I only had one new outfit I went shopping the ne... Continue»
Posted by multiplierx 6 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1162  |  
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My CD / Sissy story and 1st meet humiliation

I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before talking about the meet up, skip the first few paragraphs to get to that bit.

I have always known I love girls clothes, lingerie, miniskirts, colourful sheer blouses , anything satin or lace, since a very young age. When I was 18, I finally had a credit card, and bought my own lingerie. I bought clot... Continue»
Posted by indoblu 6 months ago  |  Categories: BDSM, First Time, Shemales  |  Views: 5796  |  
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