Babysitter Turned Sugar Baby

After I agreed to be Mr. Connel's sugar baby, he took my hand and led me up the stairs. Right before we entered the door into the master bedroom he looked at me seriously, with the hint of a glimmer in his severe eyes, and told me that "once we get in there, Vanessa, you have no say. Inside that bedroom you will do anything I tell you to do," I gulped nervously.

"Yes, sir." I replied, hesitantly.

He opened the door and sat on the bed, while I stood in front of him.

"Undress," he ordered sternly.

"Yes, Mr. Connel," and I began to remove my jeans and blouse. I stood a bit awkwardly in my white lacy underwear and bra.

"Take those off too," he reached into the nightstand and grabbed his phone. He put the phone up to film me.

That made me hesitate. What would he do with the footage? I waited too long, and in one move Mr. Connel grabbed my tiny waist and bent me over his knee, and spanked my ass as loud as possible.

"I said undress, and you will do what I say right away," he quietly said to me, with anger in his voice.

I gasped. "Yes, Mr. Connel, I am very sorry sir," he liked this, and roughly shoved me up.

"Clothes off. Now," he ordered.

I removed my bra and my panties, while he filmed it. He got up, and still holding his phone camera, filmed every inch of my body. He grabbed my large breasts, lifting them and watching them jiggle when he dropped them.

"What are you doing, sir?" I asked, a bit regretful of being his sugar baby.

"You are my sexual property now. With my business or with real estate, I always inspect my property. Now I am inspecting you. I want to make sure that $2,000 a week is the right price," he said nonchalantly.

"One day I will be using you as payment, and I want potential receivers to know your worth," he added. I didn't know what this meant, but the intensity of the interaction turned me on. I could feel warm dampness between my legs.

He stood to my side and told me to jump up and down slowly, and watched. He moved behind me.

"Open your legs wide," he told me, and I immediately did as told.

He placed his phone under and spread my vulva lips, revealing my vagina. He began to softly touch my pussy, then inserted a finger into me, his phone on the ground recording. It hurt, I never even used tampons before much less put my fingers in. At the same time, it felt incredible. I was unbelievably wet.

He got up, and told me to touch my toes. I did as told, and he opened up my already- sore ass cheeks. To my horror, he began to touch my asshole and using the slickness of my vagina, he inserted a finger there. That hurt too, but also felt naughtily good. He put his phone back on the nightstand.

"Kneel, and open your mouth so I can see your tongue," he told me.

I did as told, and he moved in front of me. He took his pants and shirt off, revealing his toned, ripped physique.

"This is why I agreed to this," I thought with desire.

He put his penis close to my face and said "suck my cock". I did as told, taking his cock as deep as I could into my mouth, as far as it would go. I moved back and forth, going faster and faster, trying to remember all the tips that I learned from experienced friends and magazines.

He put his hands on my head, and helped push my head, giving me a faster tempo. "You're so innocent but such a little slut for me," he said admiringly. The praise and his moaning made me determined and more turned on. His moaning began to pick up and get loader, and I felt his cock twitching in my mouth as globs of semen filled my throat.

"Swallow," he commanded.

I did, licking every bit of him off my lips and opening my mouth to show.

"You are so sexy, Vanessa," he said to me.

"Now get on the bed." I laid down onto his massive bed, while he stroked his cock to an erection again. Spreading my legs, he lined up his cock with the entrance to my vagina, and began to slowly enter my tight hole. It hurt horribly, but once he began thrusting at a beat the pain began to give way to pleasure. His thrusts got harder and faster until he was fucking me at full force. I could feel his massive, 11 inch erect cock hitting my cervix and stretching out my pussy, and his balls slapped against my extremely wet pussy.

"Your pussy is so fucking tight," he told me between pumps. Finally he came in me; I could feel my womb lined with his warm seed.

"Get onto your hands and knees," he said.

I did, and from behind I heard something squirting from a bottle. I felt fingers putting cool gel onto my asshole, and I felt scared for a moment. He began to finger my asshole, one at first, then adding a second and a third. The pain quickly subsided into a new form of pleasure. The fingers disappeared and I felt the pressure of a cock entering my asshole.

He began to fuck my asshole, slower and more gentle than my pussy. It hurt when he first entered, but the pain subsided. It was the most intense and pleasurable feeling I've ever felt. It was like an ocean wave of sensual bliss washed over me. He went faster and harder slightly, until I heard him grunt and finish in me. I flipped over and laid on the bed, dripping and exhausted. He stroked my body approvingly.

He turned back to his nightstand and got out his wallet. He took out $500, and rolled it up.

"The 2k will be in your bank account this afternoon. This," he held up the roll of bills, "is for being such a good sugar baby. Consider it a slut tip," with that he inserted it into my dripping pussy.

He thought for a moment, then asked me if I was on birth control. I replied that I wasn't, and he got out another $50.

"This is for Plan B. You can get it at a pharmacy or the store. You need to take it today so you don't get pregnant. I will have my secretary make an appointment for a gynecologist for you, who can put you on birth control and do checkups," then he rolled up those bills and tucked them into my red and glistening pussy.

"Go shower and get cleaned up, and we will figure out dinner. Did I mention that you are staying the night?" he said, turning out of the room.