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sissypenetrator

Author: 

  • sissypenetrator

Organizational: 

  • Author Page

Audience Rating: 

  • EXPLICIT CONTENT


sissypenetrator's tales

Sasha - An Introduction

Author: 

  • sissypenetrator

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Fiction

Genre: 

  • Transitioning

Character Age: 

  • Preteen or Intermediate

TG Themes: 

  • Age Progression
  • Autobiographical
  • Voluntary

TG Elements: 

  • Estrogen / Hormones
  • High heels / Shoes / Boots / Feet

Permission: 

  • Posted by author(s)

Prologue:
Hi, my name is Sasha Anderson. I just turned 12 years old last week. I'm
four foot ten inches tall, and almost 90 pounds. You may have seen photos
of me on the internet. I am a contestant in America's Hottest Teen
Transsexual Pageant, under 13 category. It's an online beauty pageant for
young transgirls. Some nasty people online have accused my mom of setting
me on the path of being a TS porn star and escort. But it's way more
complicated than that. This is a path that I choose for myself. She
definitely helped set me along with the process though, and I will be
ever grateful for this.

I had been crossdressing on and off for a few years, but after 5th grade
I decided I wanted to start wearing more adult style clothes, and grow my
hair longer. I also begged my mom to let me start hormones. I also showed
her stories about how sexy child models made lots and lots of money on
the internet. I was betting that with the right amount of hormones and
puberty blockers, that I would make a smoking hot teen model in a few
years. So on my 10th birthday, we set up social media profiles for a 10
year old transgirl who was an aspiring model. And that was the morning I
started taking the little purple pills that my mother managed to acquire
over the internet. Although my mother and I live in Seattle, we set up
all the contact information to be in Los Angeles, where my mom's sister
lives. The plan at first was to give me puberty blockers and a very low
dose of estrogen for a few years. We followed that plan for about 9
months. But then when COVID hit, school was all from home. We didn't need
to worry at least for now about hiding my feminized body because
everything was remote. So we did what any reasonable people would do in
my position, and we started adding more estrogen to my regimen. We did it
slowly at first, and although I didn't get a lot of breast growth, my
nipples became very sensitive and bigger. My butt also got more rounded
and softer. By my 11th birthday I could easily pass for an 11 or 12 year
old girl. My long blonde hair was down to my shoulders by the end of the
first summer after COVID, and my mom had her stylist give me bangs and a
medium bob style haircut.

My mom had been making professional modeling photo and video sets for my
social media accounts. We set up an account with a local PO Box down in
LA that my fans could send gifts and clothes that they would like me to
wear, and my aunt would forward the packages to our house in Seattle.
Once I had graduated 5th grade, my mom allowed me to use my own private
social media accounts. It was just easier that way because a bunch of
them wanted to do private chats or ask for sexier photos. It was a little
bit after my 11th birthday that I learned about the Teen Transsexual
Pageant. One of the members told me about it in a private chat. His name
is Mike, and he is always one of the most generous guys that I talked to
in the chats. He produces high class porn sites that are very popular. He
confided to me that they also have a secret child modeling agency that
for legal reasons cannot be associated with the porn studio. But he
assured me that they all used the same makeup and wardrobe people, and
that the contents would be very sexy and glamorous, as far as they could
legally get away with. His studio was down in Los Angeles, where my aunt
lived. I did a little research on the internet and discovered that some
of the porn studio models had been alleged to be underage during certain
movies. There was never more information about this to be found, and the
stories seemed to just have a dead end. My mom and my aunt were very
suspicious about this, but for me, it seemed like an opportunity. I had
seen those movies of the glamorous models in their lingerie getting
fucked on camera. I wouldn't admit it to my mother, but I secretly wanted
to be one of those girls. I may have had a penis, but I was determined to
be one of those girls when I grew up. My preference would be to get a sex
change as young as I possibly could. But if that wasn't possible then I
wanted to go into TS porn. But I was only eleven years old, and I knew
that none of this would be possible until I got older. And after being on
the hormones for a while, I started to find myself attracted to adult
men.

By this time, my photos sets were starting to become very popular. We
would release usually one set per week of me wearing different outfits.
The more tame sets would be released on my regular social media, and they
were my public persona. These photos were of me hanging around the house,
or wearing conservative swimsuits at the pool behind our house in
Seattle. But then we also made more revealing and sexy photos. These
could easily bring in thousands of dollars for a single photo-shoot.
Through the social profiles, my mom started talking with men who started
commenting on my photos. This is when she started getting professional
photo shoots done of me. My fans from the internet would send me outfits
and gifts. By the time I started 6th grade, I had a complete female
wardrobe, including a large selection of sexy lingerie.

Tiffany Starts her modeling career

Author: 

  • New Author
  • sissypenetrator

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXTREMELY EXPLICIT

Publication: 

  • Fiction

Genre: 

  • Transitioning

Character Age: 

  • Preteen or Intermediate
  • Teenage or High School

TG Elements: 

  • Bad Girls / Promiscuity
  • Estrogen / Hormones

Permission: 

  • Posted by author(s)

Steve Hardman was a billionaire at just age 35. He made his fortune in the cryptocurrency craze of the early 21st century. He's also 6 foot 3 inches of lean muscle, always keeping himself in great shape. He generally splits his time between NYC where his 60th floor penthouse has a commanding view of Central Park, and the rest of the year is spent at his mansion in Marin County, California. He's a lifelong bachelor and has had no long term girlfriend. And to be honest, he prefers it that way. He prefers the playboy lifestyle and he can easily afford it.

Maria Alexander is a high class escort. She had her son Timmy when she was just 18 years old, and kept escorting after she gave birth. The father was one of her clients, who quickly skipped town and she never heard from again. Despite being a single mom, she was happy with just herself and her son. Marina eventually got into porn, which allowed her a more luxurious lifestyle. She had a nice condo in Los Angeles with a sweeping view of the city, and she drove a fancy BMW that was given to her by a client. Life was good for both of them.

She knew of her son's sissy and girly ways from an early age, and encouraged him to be as femmy as possible. She bought him girls clothes, taught him how to do makeup, and they played dressup and fashion games from an early age. At age 11, he really got into being a girl as much as he could, and Maria helped him set up a web site. Coming up on his 12th birthday, he told her that he wanted to be a fashion model and be a girl full time. Although shocked at first, Maria quickly embraced the idea, and came up with a plan to help. They were able to acquire puberty blockers and hormones over the internet, and she started the feminization process on his 12th birthday. With the financial support of Mr. Hardman, she was able to start having him home schooled instead of going to public school for the 7th grade.

Timmy had been as fem as he possibly could get away with, even at school. His hair was long and he regularly kept his brows plucked. He would do things like wear girls sneakers and jeans to school. Most of the kids thought he was weird, but they didn't tease him about it. Whe he started a modelling page on the internet as his alter ego Tiffany, no one at school caught on that it was actually him.

Her web site was a modelling portfolio, where customers could pay a monthly fee and download modelling sets and short videos. Her customer base was varied, but was mostly men who are tuned on by young femboys or transgirls. She would have weekly chats with the highest paying customers, and would model clothes that they sent to her mother. She would model everything from innocent schoolgirl outfits, to girly anime characters, or more revealing sets for her more elite customers. After around 6 months on her illicit hormone regimen, Tiffany had 2 small but definite breasts, and her hips started to fill out. She was starting to look less like a 12 year old boy and more like a 12 year old girl, with the curves and soft skin that would be expected of a girl that age.

One of her most daring photosets came out at this time. In it, she was expertly made up with deep red lipstick, dark eye makeup, expertly shaped eyebrows. Her light blonde hair was in a bob, and she wore a black choker and silver hoops in her ears. Her bra was black satin with tiny cups that barely covered you young growing breasts. She had on a black satin garter belt attached to sheer real silk stockings, and her feet were shiny black high heel pumps, the kind you would typically see on a high class porn star. Her black satin panties left no room to the imagination and you could clearly see that she had a small feminine penis. Although with the hormones she was on, she would never get a bigger cock, she could still get hard and she was definitely excited in this shoot. Most of her fans really loved this, by the way. The set featured her posing in suggestive poses that showed off her young developing body, which by this age she was keeping completely hairless except for the hair on her head. It secretly made her hot thinking about all those men that are turned on by her photosets. During their members only chats they would sometimes ask to do more illicit things. The chats were supposed to be monitored by mom, but when certain elite customers came on, she would just tell Tiffany to be a good girl and that she trusts her judgement. Tiffany was elated by this because she knew she could make more tips with these guys, and also because more and more she was starting to get turned on by the thought of getting fucked by one of these successful rich businessmen. She was especially attracted to Mr. Hardman.

With her mom's help, she was starting to bring in enough money that her mom vastly cut back on her escorting activities, but she did still see some elite clients. One of those clients just happened to be Mr. Hardman. Maria had known that Mr Hardman had a thing for young tgirls, and she told him about Tiffany, the site, and everything. She explained to Mr. Hardman that she couldn't date the first year she was on hormones, but that when she is 13 that she can make her own decisions. Mr. Hardman secretly thought that she was the mom of the year.

To be continued...


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