Rose Meets Her Master

I didn't need the money, but I made a profile on the sugar daddy website anyway. In the about me section, I wrote "Young female slave looking for master. Inexperienced, needs training". It wasn't long before I got a message in my inbox from a tall, attractive man with an incredible smile.

"Saw your post. I'd be interested training you, and I'll pay you $100 per training session. I'd like to meet for dinner with you tomorrow. Fill out this questionnaire and bring it with you. Wear a dress that shows your cleavage and heels. If I'm pleased, we will begin tomorrow." The pages listed sexual acts, and next to each act it had the numbers 1 through 10. 1 meant it was beyond my limits, 10 meant it was beyond my wildest dreams. There was also a section for comments.

Deepthroating: 8. But I need more training. It doesn't take much to make me gag.

Swallowing cum: 1.

Having cum in your mouth: 2. I really hate cum, but if I could spit it out fast it could be okay.

Anal: 4. I'm unsure. I've never done it, but it could be okay.

Bondage: 7.

Electric shocks: 3. I haven't tried this, so I don't know what my opinion is.

Being urinated on: 2. I can't see being into this.

Swallowing urine: 1.

Being watched while urinating: 2.

Gagging: 3.

Vomiting: 1.

The list went on. Spanking (6), whipping (3), pussy-whipping (2), nipple clamps (7)-on and on for seven pages. I finally finished it and went to sleep.

The next day, I put the papers into a portfolio and put on my sluttiest dress and heels. My sluttiest dress wasn't too slutty by any means, but it was the only one that showed any cleavage. I hoped he would like it. It was a small black dress I had used in college when my best friend wanted to go clubbing for her birthday. I hadn't worn it since, and couldn't believe I was going to go out dressed for the club for dinner. The heels made my legs look long and exposed. My pussy felt like it was vibrating on the drive to the restaurant.

As soon as I pulled up to the restaurant, I realized the man must be rich. The exterior of the building was beautiful-deep red brick interspersed with huge crystal windows. Inside, the room had a flawless wood floor, chandeliers hung from the ceiling, and each table had a beautiful rose arrangement surrounded by candles.

"Welcome to Risetti's. Um... how can I help you?" the server asked. She seemed distracted by my breasts. It probably wasn't too common for women to dress this way in such an upscale restaurant. In fact, a quick glance around confirmed it. My dress would be modest in a club, but here I looked like a hooker.

"Oh, I'm... meeting someone here," I stammered.

She glanced down at my cleavage again. I pulled the portfolio, holding the questionnaire, over my breasts protectively. "Is your name Rose? I think the gentleman this way is waiting for you." She led me into another room to the table where the man was sitting. I still didn't know his name. I sat down and said hello. He didn't say anything. He slowly looked me up and down, and then took the portfolio.

"Wine?" he asked.

"Yes. I'm Rose. Hi. What's your name?"

"That's not for you to know," he said.

His food had already arrived and he had finished most of it. While he was reading through the pages, I ordered my dinner. He didn't speak a word to me while he was reading it. I shuffled uncomfortably in my seat. Why was he reading so slowly? My food came before he was finished. Finally there was at least something to do while he wasn't talking to me.

"Don't eat that."

"What?" I asked.

"You're feeling ill and you'll take it to go." He put the papers back into the portfolio and smiled. "You're coming home with me tonight." I could feel a grin coming on my face. He must have liked what I wrote in the questionnaire. As the waitress came by, I stopped smiling and tried to look ill.

"I'm not feeling well, can I have a box for this?" I asked. Once my dinner was packed up, we were ready to leave. I thought it was odd that he invited me to dinner and we didn't even eat, but I was excited to see how the night would unfold. It excited me that he was too impatient to play with me to even let me eat. The man gave me his address and we drove separately to his house. He told me to wait until he was inside and then to knock on the door, and to make sure that I was wet when I got there. The drive was short but getting wet was no issue. I was excited. As soon as he had gone in, I walked up to his door and knocked. He opened the door.

"Come in, Rose." I came inside and he shut the door. He led me to another door. "I want you to walk into this room, undress completely, and get onto the table. Make sure your feet are in the stirrups and your knees are far apart so I can properly examine you. I'll be in in a minute."

I walked into the room where a gynecological table waited for me. I got undressed and laid back, my pussy and asshole completely exposed. The examination table was even less comfortable than at a real gynecologist. It was cold, hard metal. My heart was beating fast as I waited for him.

The door opened. My new master was wearing gloves. "You're not allergic to latex, are you?"

"No."

He grabbed my face. "That's no, sir."

"Yes, sir," I said.

"Good." He let go of my face and stood up.

"Open your mouth as wide as you can," he said.

"Yes, sir." I opened my mouth and he took a light and looked inside. He stuck his fingers into my mouth, prodding my tongue, my cheeks, and the back of my throat. I gagged.

"Is that as far as you can open your mouth?"

"Yes, sir."

"You're going to take more training than I thought. There's no way my cock could fit in your tiny mouth." He got on his knees to look closer at my pussy. I could feel him pulling apart my pussy lips to look closer. "You're wet. Good job." He stuck a finger in my pussy, then two, and then three. "Hmmm." I moaned. "Be quiet," he said. "I didn't ask you to speak." He then started rubbing my asshole. Now my heart really started racing. "So you're a bit apprehensive about anal, huh? That's not gonna do." He slowly started pushing his finger in. I clenched up. "Relax. You're never going to be able to take my cock like that." I relaxed, and he pushed his finger all the way in. My heart was beating fast. I had never had anything in my asshole before. "Your asshole is microscopic. It's going to take some training to get in there. I'm going to put a butt plug in there to start you on that. Now let me know if this hurts." He slid a very small butt plug into my asshole.

"It doesn't hurt, sir."

"All right, we'll try something a little bigger then." At first, the bigger plug didn't hurt, but as it got to the thickest part I started feeling pain. I whimpered. "Relax," he said. "If it hurts too much we'll go with the first one". I exhaled, trying to relax, and the plug slid in the rest of the way. "Good," he said. That's what you're going to wear while you eat dinner. Now get on the floor, on all fours." I obeyed. He latched a collar around my neck and then led me out of the room on a leash into the kitchen. On the floor next to the table was a plate with the food I had ordered earlier along with a shallow bowl of water.

"Eat, and don't use your hands," he said. I looked up at him, confused. I had never been treated this way, and I wasn't sure what to make of it. "Come on, it's okay, girl," he said, rubbing my hair. "You can eat." I apprehensively lowered my head to the plate and began to eat. I had gotten a fish filet and it was difficult to eat without my hands. I was making a huge mess. There was food all over my face. I felt my master's feet on my back. He was using me as a foot rest. I kept eating.

"Make sure to get some water, too. You're going to need it." I lapped up some water out of the bowl. I hadn't realized how thirsty I was until then. I probably had lost a lot of water from how wet I was. I felt his feet leave my back and then I felt his fingers rubbing up and down my clit. I moaned.

"Be quiet. If you make a sound without being asked again, there will be consequences."

"Yes, sir."

I tried to ignore him touching me as I lapped up the rest of the water but it was nearly impossible. He had hardly touched me all night and his small caresses were driving me crazy.

"I'm finished, sir."

"Good girl." He led me on the leash to the bathroom where he cleaned off my face, and then back into the first room, the one with the examination table. He removed the leash. "Get on your knees." I got on my knees. "Now, since we both agree on deepthroating I want to start training your jaw for that. For that, I have what is called an o-ring gag. This metal ring will force your mouth open, and over time I will force your mouth wider and wider, until I can fit my cock in it. Do you understand?"

"Yes, sir." I said.

"Now be a good girl and open your mouth as wide as you can." I did as I was told. He took a ruler out of a drawer and measured the distance between my teeth. Then he selected a ring and attached it to a leather gag and put it on me. I had to open my mouth even wider because it barely fit. Now my mouth was trapped open. I moved my tongue around, exploring this new feeling. My breathing sounded different like this.

"Get on all fours again and look at the floor. I want to see you drool. You're going to wear this for 30 minutes every day until I notify you otherwise, do you understand?"

"Ess, suh," I said. Drool was already dripping from my lips as I stared at the ground. I heard him walk behind me. "During your jaw session tonight, I'm going to fuck your ass with this butt plug. You will be required to wear this butt plug for at least two hours each day. You must tell me when you wear it and ask for permission to take it out, with the exception of using the bathroom." He slowly pulled the butt plug in and out of my asshole. My breathing got heavier, but I refused to moan, knowing that I would be punished. My drool was hanging from my lips and had almost reached the ground. I was panting. Suddenly, he jammed the butt plug into my asshole and I cried out in pleasure. I couldn't help it. "I thought I told you not to make a sound," he said. "You're going to have to be punished, you little slut."