tagTransgender & CrossdressersTurning into His Toy Ch.02

Turning into His Toy Ch.02


I couldn't believe what was happening. I am on a plane flying from my home state of Ohio to Los Angeles to meet my new owner. It started when I met him on a gay chat room and told him I wanted to become a feminized sissy slut. We talked and before I knew it he sent me tickets to fly to California. I left my home in the middle of the night and left my parents a letter. They probably wouldn't understand at first but in time I know they would want me to be happy.

I grabbed my luggage which wasn't much, just a change of clothes and some other basic necessities. I texted my owner that I had landed and he told me to meet him outside in the terminal pickup area. At first I was afraid I wouldn't be able to find him, but as soon as I stepped outside I could see him, the man I would now call daddy.

He had this feeling to him I couldn't put my finger on. There was just something about him that made me want to submit to him. Maybe it was the fact he was much taller than me probably about 6'3 while I was under 6'0, or maybe it was because he was much bigger than me. He wore a pair of tan cargo shorts, a black t shirt, and sandals, but I could see he was very muscular and well built.

To be quite frank I had kind of fantasied about a much bigger and stronger man taking advantage of me. I try to hide my obvious erection by walking like a dumbass to him and he smiled. He knew I was turned on just by seeing him. I blush as I walk up to him as he is leaning against his cherry red ford torino.

"Hello my sissy boy how was your flight?" He asked raising his voice a bit so people nearby could hear. My face goes bright red with embarrassment.

"It was fine." I said quietly.

"Good to hear did you bring the paperwork like I asked?" He asked me. He was talking about copies of my birth certificate and medical records.

"Yes it's in my bag." I answer him still red faced. The smile disappears from his face and almost turns into a scowl.

"Yes what bitch?" He asked annoyed. I realized I spoke without using his proper title.

"Yes daddy I have all the paperwork in my bag." I answered again.

"Good now give me your bag and get in." He orders me sternly.

"Yes daddy." I answer submissively and give him my bag. He opens the door to his ford torino and gives my ass a quick smack before I sit down. I felt so turned on by the smack and calling another man daddy that I wish I could whip out my dick and jerk myself off right then and there. He opens the trunk and throws my luggage in and then sits in the driver seat and starts the car.

"My place is about an hour and a half away from here so we can talk a bit until we get there." He explained.

"Yes daddy." I simply answered.

We drove further away from the city and more into the country side as we talked.

"I think it's time I explain to you what I do for a living." He said not looking at me and focusing on the road.

"What I'm doing for you is a part of my business. You see I run an escort business and all of my escorts are shemales. Sissies are becoming more popular than regular women because there is no fear of pregnancy or menstruation. Now when we begin your feminization it will be both physical and mental. The hormones, clothes, surgeries, they cost a shit ton of money. You pay that money back by being one of my whores." He explained.

"Your body will change in shape and size. You'll get hips and a nice ass. Over time you will also get a nice pair of tits and lips too. The hormones will stop your facial hair from growing, the hair on your head will grow much faster, and will cause your voice to become more lighter and feminine." He continued.

"Now once you pay me back you are free to go or you can continue to work for me and make a pretty good living, but while you are in debt to me you are my property. You will be my whore and doll to play with and dress up however I feel like and if you fuck up or cross me I will punish you. You will be a sexual plaything to me and many others when we begin." He told me as I listened trying to process it all.

We come to a t junction in the country side. He stops the car and pulls out an envelope from the center console.

"Inside this envelope is two grand. This is a choice I give all my pets before they go through training. Now if we go right we will be in a town in about twenty minutes and then I will let you go and you can get a cab, board a plane back to Ohio, and still have enough for a cab to get back to your home. Or if we turn left we will go to my home and I will train you to be my sissy toy. Now is the time to choose, but choose wisely, because either choice you make there is no going back from here." He said making sure I was understanding everything in detail.

I thought very hard about this. My next decision will change my life forever. I pondered over every pro and con of both choices. Eventually I settled it and made my decision.

"Daddy I want you to go left. I to be a girly girl and learn to please men and become your tranny whore. Please turn me into your toy daddy pretty please!" I pleaded with him.

Daddy smiled and put the car into drive and turned left.

"Excellent choice and trust me you are going to love your new life sissy." He told me grinning.

"Also start thinking of a new name for yourself. If you want I can give you one." He offered.

"I always liked the name Lilly, its really cute and feminine." I stated.

"Agreed, alright then Lilly it is." He said.

We pulled up to his home and it was rather astonishing. It wasn't a mansion, it was very large and spacious. Lots of open land in every direction, it was quite peaceful out here.

Daddy pulled up to the driveway, got out, grabbed my bag from the trunk, and opened my door.

"Come on out your training begins today Lilly." He ordered me. I only just came up with the name and he is already calling me that, I really liked it.

We walked up the steps and entered through the large front door. When he opened the door we were greeted by two maids. One was white with red hair and blue eyes. The other was black with straight long black hair and brown eyes. Both had their hair tied back in ponytails. They had very sexy maid uniforms including black five inch heels, black stockings, very short skirts with white aprons, they also each had a black leather collar on with a tag.

"Welcome home daddy." They said at the same time while doing a curtsy.

"Ladies this is Lilly, our newest trainee. Lilly the redhead is named Ashley, and the one with black hair is named Brittney." He explained pointing to each of them.

"Ashley go get me some education tools and meet me in the study, and Brittney take Lilly's bag please." He ordered them both.

"Yes daddy." They both answered before Brittney takes my bag and Ashley runs off.

"You follow me." He ordered pointing to me.

"Yes daddy." I answer submissively.

We walk through the house until we reach the study . Its fairly large with some book shelves a leather couch and some leather chairs, and a fire place. Daddy sits down in the leather chair and looks me over.

"Strip." He commands.

I was a bit reluctant at first, but not wanting to anger him I take of my shoes, socks, shirt, and jeans.

"Boxers too." He said impatiently. I then take my boxers off. I cover my groin instinctively.

"Take your hands off your cock." He orders.

"I'm sorry daddy i'm just a little embarrassed." I Explained blushing again. Daddy is now angry. He jumps up out of his chair walks over and grabs me by the ear and pulls me over to the chair.

"Ow, ow, ow!" I yell as he pulls my ear. He then puts me over his knee and then begins to spank me, not playful spanks, he wants this to hurt. He hits each cheek with his hand as hard as he can. I squeal and squirm as another has me over his knee and is spanking me. He continues with his barrage of hands on my bare ass even when I cry and beg for him to stop. It isn't until my ass feels red and hot that he finally stops.

"You do not disobey me bitch, ever!" He exclaimed giving my ass a final swat before pushing me off his knee onto the floor. I stand up and rub my red ass cheeks. I was definitely going to be bruised for a few days.

"Daddy I brought the tools." The redheaded maid named Ashley quietly came into the room holding a tray, on it were a pair of nipple clamps, a ball gag, a pair of handcuffs, a wooden paddle, and a pair of white cotton panties.

"Ah good Ashley is here with the education tools. Now we can have some real fun." Daddy said smiling wickedly.

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