Brandi's Diary Ch. 01

This Friday is my 21st birthday, and I could not be happier about the wild young girl I've become over the last three years. The following is the mostly true story of how I went from a scrawny geek to the hottest t-girl in all of Los Angeles.

I'll fill you in more on my background as my story goes along, for now it makes sense to just give you a brief outline of who I am. I grew up north of Los Angeles in the San Fernando Valley; it was just me and my mom, one of my best friends. My mother had me when she was young, and as cliché as it may sound, it really was the two of us against the world. She is one of the greatest people I know. She did what she needed to do to provide for the two of us, living in the Valley, that basically meant she worked in the adult film industry, and occasionally as an exotic dancer.

Through of all of that, I had a fairly great childhood, I managed to find friends who were totally accepting of me. I was never really "one of the boys" though, I only grew to be five feet two inches, and had a pretty petite frame., I certainly was not the captain of the football team. While, I was not the most popular kid in school, things were not terrible

I guess I never bothered to define myself, I was open to men and women, and never really felt comfortable being masculine. Being alone quite a bit, I became very adept working on a computer, and I wrote some programs that would attract the attention of some major software companies. On my 18th birthday, I sold my company for more than enough money to set myself up for life, and subsequently set out on a journey to explore all the pent up sexual fantasies I had.

So my story begins here, with a giant bank account and the whole world in front of me. It would be disingenuous of me to claim that I was inexperienced sexually, I had plenty of fun, and I had in fact a few times dressed up around the house as a cute girl, big hair, tons of make-up. As I said, my mother was very accepting of me, and she totally encouraged me. Of course, I really wanted to try new things, and the one of the first things I really wanted to do was explore my submissive side with a professional mistress I had found and lusted over online for quite a while.

Shaking a little bit, but mostly excited, I called up Lady Natalie and arranged for a session the next afternoon. Since it was my first time, I really had no idea what I was looking to do, or what would actually happen, I just for some reason was drawn to the pictures I had seen of Lady Natalie. She was in a tight latex bodysuit, and something about her curves just told me this was who I needed to meet.

The next day, I drove down to meet Lady Natalie at her dungeon in Hollywood. Ringing the door bell I was lead to a waiting area by an amazingly attractive young receptionist, with her hair pulled back and glasses she looked like a stereotypical porn actress librarian. My mind was beginning to wander to what I would like to do to the receptionist when my mistress for the afternoon walked in. She looked better than I could have ever imagined, intricate leather bustier, leather thong, thigh high silk stockings and 5-inch stiletto heels. Her blonde hair draped over her shoulders, and her oversized breasts peeking out, I was on the verge of losing it right there.

She took one look at me and purred, "I know exactly what to do with you, come..."

As I stood to follow her, the receptionist rushed over and put a collar and leash around my neck, and told me to obey all commands. The leash was handed to Lady Natalie who lead me down a hallway with multiple doors. Stealing glances, I could see each room had a different theme, a medical room, a dungeon with a cage, and the room we settled in, which looked like a Hollywood star's dressing room. There was a giant make up mirror and racks upon racks of glamorous outfits and whorish minidresses, a closet filled with shoes, and dressers and trunks filled with lingerie.

"You are the perfect little sissy boy, I've been waiting for someone like you to come along for so long, we are going to have so much fun today, just think of me as your new BFF and I'll make sure you reach your true potential. Now strip off those frumpy boy clothes. We need to get you pretty."

I didn't exactly hesitate; I had certainly played with gender roles in the past, and would be lying if I said I had not fantasized about being a slutty party girl myself. So I eagerly complied with the orders, and exposed my smooth feminine body. Lady came over with a riding crop started tapping my slowly growing cock.

"This right here is such a shame, you would make the perfect little girl otherwise. Oh well. Let's find something for you to wear, what's your style?"

Normally I might try and play a little coy and pretend I was being forced to go along with this, but my eagerness overtook me and I sprinted over to the rack of minidresses, and found the shortest, tightest black dress I could. It barely covered my ass, was low cut in the front, and exposed all of my back, with a couple chains draped across the back.

"Oh does my little girl want to shake her ass for all the men in the club, well we're going to need some hot heels to go along with that outfit."

She first handed me the smallest thong imaginable and had me put it on, as she went to rummage through the closet for shoes. Natalie gave me some little ankle boots, they had buckles and exposed my toes. Before I could put on my new dress, Natalie told me to sit at the makeup mirror and began to completely transform my face. When she was finished, she topped it off with a dark red lipstick and a long blonde wig that had curls down the back. Spinning around in the mirror I was shocked how much I looked like a girl. I knew I was pretty small and petite, but I was a hot girl.

I stood up and walked to the full-length mirror as Natalie handed me the dress, I slowly pulled it on. When finished, if I didn't know better I would have thought it was someone else in the mirror.

"My, my, my, even better than I envisioned when I saw you walk in today. I cannot wait to introduce you to my boyfriends; you are going to make the prettiest cocksucker. But first, you have perfect your skill."

I had come to Lady Natalie today without much of an idea what would happen, I thought maybe she would tie me up, torture my cock, call me worthless and humiliate me. Instead, she awoke in me this dormant desire that I had to be the hottest, sluttiest, girl in the city. I wanted to suck all her boyfriend's cocks at the same time, I wanted to be passed around like a party favor, but first I had to learn to act like a dirty whore.

Lady Natalie grabbed a large black strap-on cock from one of the trunks and had me help her put it on. She then had me kneel in front of her and slowly begin to take the big veiny dick into my mouth. She starting to slowly pump it and before long I was gobbling it up and deep throating it. I began to lick to the balls and stroke the shaft, I wished with every fiber of my being it was real.

Lady then grabbed my shoulders, had me stand and violently turned me around. Spreading my legs she pushed me over against the makeup table. I felt her hands pull my thong down to my ankles and lift my short dress over my ass. I was totally exposed and I loved it. I knew what was coming, but was shocked nevertheless to feel the cock start to push into my ass. The next thing I knew I was being fucked in the ass by a mistress I had desired for months, dressed like a hooker on the corner and loving every minute of it.

"Stroke your little girl cock!!!" Lady Natalie screamed.

After a few minutes of pure pleasure, she pulled me from the table and had me kneel on all fours over a clear glass bowl. I knew I would not last to much longer.

"Cum into the bowl, we want to make sure you get fed today."

As the plastic cock kept pushing further into my virgin ass, my own cock began to throb, before long I was shooting my load all over the bowl.

"Hmm, look at how yummy that looks, now lick it all up."

I eagerly complied with her order and lapped up the cum like it was the tastiest thing in the world. Before I could finish it mistress grabbed the bowl and pulled it away from me. Still on my knees I looked up at her.

"All men love it when they can shoot their load on your face."

As she said this Natalie poured the rest of the bowl all over my face, coating my lips. She then grabbed my leash and pulled me towards a mirror.

"This is how all dirty little whores look after pleasing their man."

Looking at myself in the mirror I wanted to cry tears of joy, my red lips covered in cum, dark massacre streaks from the facial. I had taking a huge cock and loved every minute of it. My only regret, I wish it had lasted longer, but I was so excited I'm surprised I lasted as long as I did.

"Next time we may have to find a real man for you to please."

Perhaps Lady Natalie thought I was just another guy signing up for a good time a few hours at a time, but I knew from that moment that I was destined to become famous in the city as the sexiest little t-girl slut it at ever seen.

I had so much fun with Lady Natalie as the years went on we would set up a weekly session, and she became one of my best friends and teachers in my transformations, but those are tales for later in our story. Today she had set me on an irreversible path, and I was so eager to fulfill this dream, I raced home with visions of what to do next.

I had so much to do...