Babysitter Turned Sugar Baby

When I was in high school and college, I worked as a party host at a kid's birthday party venue. It was only minimum wage, but the tips were good, and I needed the money for college. I had just turned 18 weeks before, and was tiny: a size 4 with large DD breasts, a cute butt, bright blue eyes and dirty blonde hair. I got lots of male attention, but I didn't know what to do with it. I had only ever kissed a boy at this point!

At one of these parties, the parents of the children stayed. It was mostly moms who talked at the tables, but towards the back of the room sat a dad. He was a bit on the younger side, early 30s maybe, but he didn't speak to the other parents. Instead he watched me, a look in his eye that my innocent self couldn't identify. I went through my tasks, and took the payment from the host parents. They were very complimentary of how I worked with the children, and tipped me generously. I had stepped out into the hall to grab something, and the dad came up behind me, startling me. He was close to me, and he was tall. Even with winter layers on, you could tell he was fit. His brown eyes sparkled; he was honestly quite handsome.

"You were really great with the kids in there. I need a new babysitter for my 10 year-old daughter. Is that something you'd be interested in?" he asked me, his warm breath close to my face.

"Absolutely, Mr. -,"

"Connel. My name is Jack Connel, but you can call me Mr. Connel."

We swapped numbers, and arranged for me to meet at his house the following week. Following introductions and checks for my CPR and first aid certifications, I met his daughter, Anna. We got along very well and I became his regular babysitter on Tuesday and Thursday afternoons. For several weeks, everything was professional. He paid in cash, left, and I took care of Anna.

A month in, everything changed. I went to my regular Thursday babysitting appointment, but when I arrived, Anna wasn't there.

"I am so sorry, Anna is at her mother's place, there's a long weekend for her school!", Mr. Connel explained.

Mr. Connel was very apologetic, and offered to compensate me for the babysitting. As I turned around to leave, he called me back in, saying he had another possible way for me to make money. I had just graduated high school, and was desperate for money.

"Vanessa," he said, patting the couch next to him for me to sit, "have you ever heard of a sugar daddy?".

"No, what's that?" I asked, innocently.

He didn't answer my question. Instead, he asked a different one.

"Vanessa, are you a virgin?".

At this I turned bright red, embarrassed. I hadn't had my first time yet, and I was nervous and embarrassed at my inexperience compared to my friends.

I didn't answer.

"Vanessa, have you seen a penis?". I looked down, ashamed.

He smiled at me, moving closer to me. He gently lifted my chin so l could look into his eyes.

"Vanessa, a sugar daddy is a man who will give a younger woman gifts and money in exchange for favors and companionship. A sugar baby supplies that relationship with a sugar daddy for money. My businesses are growing, and I don't have time for a relationship, but I do miss a woman's touch. You are a very beautiful girl, Vanessa. I was hoping you would be my sugar baby."

I was overwhelmed, and my eyes started to water. "But Mr. Connel," I blurted, "I'm a virgin, I won't be any good!"

At this he smiled. "Your innocence is why I want you. You need the money, try being my sugar baby for a month? I will pay you $2000 a week."

At this my jaw dropped. It took me two months to make that!

What would you want me to do?

At this he stood up, and unbuckled his pants. Out sprang a huge cock, at least 8 inches flaccid and three inches diameter. I was petrified. He told me to take it in my hand and jerk him. I was curious, and did as told.

With each hand motion, I got more confident, more turned on, more excited. He groaned, and finally warm semen spurted out all over my hand and shirt.

He tucked his cock away in his pants, and looked at me.

"If you are my sugar baby, I have strict expectations if you want 2k a week. First, you will only refer to me as 'Sir' or 'Mr. Connel'. Second, you will do whatever I want, however I want, whenever I want. I understand that you are a virgin, and I will not hurt you. I promise. However, once you get more experience with me, the sexual expectations will increase. I will take whatever photos and videos I want, and I will share them to whoever I want. Sometimes I will loan you out to friends and acquaintances, and you will please them however they wish. You will fuck whoever I say, however I tell you to. I will buy you clothes to wear, and you will wear them. From this point, your body belongs to me, and I get say in everything. If you don't want this, you will continue to babysit Anna and i will continue to pay you. My daughter adores you, and she is my everything. If you decline, we will proceed as normal, and never mention this again. However, I think you want this very much."

I was petrified. But maybe it was the heat between my legs, my curiosity, or my new adulthood, but I decided to say yes.

My life as a sugar baby had begun.