Chapter 2: Stephano the Super Student

After only 3 months, my personal and shower assistant Kerry moved away to get her Business degree. My nanny-monster Gretta and tutor Dan moved away too. Dan had a family and only came to the mansion part of the day to teach me. I didn’t really miss them that much, but I desperately missed playing with Kerry’s body. I heard Gretta quit as my nanny because she was bored after I started behaving well. It wouldn’t surprise me at all if she were a soldier or prison guard now. Wait, my tutor’s name was really Don, or maybe David, but anyway...

My new tutor Brenda would have a room at the far end of the mansion, like several of the other staff. Brenda taught me that the staff were people too and had feelings. It was old-fashioned and rude to call them “servants” instead of “staff”. Until then, I had no idea they had lives that didn’t involve cleaning up after me.

When I met Brenda, I didn’t like her at first. She wore a very formal outfit and all I could see of her were her hands and face. Her dark hair was in a tight bun and she wore thick glasses. I thought she looked about age 40, a little older than my mom. She had some wrinkles on her neck and at the corners of her eyes.

On our first day of school, I kept getting distracted. I looked out the windows, listened to other people talking in the next room, and went to the bathroom often. In the middle of Math an aroma distracted me and I walked to the kitchen to see what was for lunch. The rest of the week was about the same. I didn’t pay attention half the time, and barely learned anything.

The next Monday, Brenda tried a different approach. Instead of the ugly bun, she let her long hair down. I thought it was pretty. She wore a purple dress instead of her usual pantsuit. I could see a little of her cleavage and her lower legs. I thought her nylons were very sexy. We started the day in my bedroom. She set her laptop on the desk and said, “You’re not paying attention or learning very much. If I don’t teach you well enough, I’ll lose my job. I think we need to try something else. I’m going to show you something exciting, but it needs to stay our secret, okay? Can you keep a secret, if it’s something fun?”

“Sure.”

She played a porn video! A nude woman took a man’s pants off him, pulled his underwear down, then gave him a hand job! I started to feel my boxers shrink. My eyes widened, and my attention was firmly fixed on the screen.

She paused it and told me, “If your average grade for the week is at least a ‘C’, I’ll do that for you on Fridays.” She rested her hand on my crotch gently.

She started the video again and the woman licked and sucked his cock, stroking it until semen shot into her mouth!

“If your average for the week is at least a ‘B’, you get that on Friday.”

“Uh, wow!”

She played another video of a woman rolling a condom onto a guy, then riding him cowgirl style. She played two more, of couples doing missionary and doggy style. My boxers had never felt tighter.

“If your average is an ‘A minus’, you can have one of those on Friday.”

I was shocked and tremendously happy. “Wow! Really?”

“Really.”

“And what if I get all ‘A’s?”

She giggled a little. “It’ll be a big challenge but if you can really get all ‘A’s, I’ll do those with you three nights a week.”

She pulled the top of her dress and bra down, showing me her nipples for a few seconds. Next she lifted her skirt and showed me her pussy. She was older than my mother, but looked pretty good for forty.

She handed me a condom and leaned over the desk. “Have a sample, then we start learning, ok?”

I shucked my pants and boxers quickly and rolled on the condom. I slid into her 40-year-old pussy, and it was great! I tried to hold out and enjoy it longer, but I probably came in only two or three minutes.

“That was SO GOOD! Thank you! Thank you, Brenda!”

“So, will you take school seriously now?”

My mind shifted gears quickly. “The other day in English, you were saying something about verbs and adverbs? Could you go over that again?”

In just a week, I went from ‘D student’ to ‘Blowjob’. I tried hard and within a month, Brenda started sleeping in my bed half the time. She set an alarm and would run back to her room before the staff started cleaning in the morning, to keep our secret.

The day before the year-end exam, she showed me an anal sex video! She said I could have her butt once a week, all summer long, if I could get a perfect score. I missed it by three points, 397 out of 400.

She was kind, letting me do anal with her once for trying so hard. It was so much tighter, and so terribly dirty and naughty! I loved it! I would have done nearly anything for more anal! She promised to let me do it again the day I got accepted to college.

We never kissed and never said anything about love, but Brenda made me very, very happy. We had the same deal the next year, and tests showed I went from 8th grade level to grade 11 in only two semesters. I’d be ready for college by the time I was 17! It was awful when Brenda moved away and I started taking classes online.

When I turned 16 instead of receiving gifts from my parents, I got a very upsetting surprise; they were getting divorced! My Dad explained on the phone that he caught my mother in bed with another man, and he couldn’t deal with her anymore. My mother explained over the phone that she was fed up with Dad having five other women in five countries, so she was leaving him for somebody better. I had a very unhappy birthday week.