Growing Up A Master - Cover

Growing Up A Master

Copyright© 2006 by MWTB

Chapter 6: Lessons in Dating, Part 1

BDSM Sex Story: Chapter 6: Lessons in Dating, Part 1 - A coming of age story about a boy, from childhood until college, discovering his inner Master. Golden Clitoride Winner, 2006, Best BDSM Story

Caution: This BDSM Sex Story contains strong sexual content, including mt/ft   mt/Fa   ft/ft   Fa/ft   Teenagers   Consensual   Slavery   Incest   Mother   Son   BDSM   DomSub   MaleDom   Spanking   Light Bond   Humiliation   Harem   First   Oral Sex   Anal Sex   Masturbation   Sex Toys   Water Sports  

Fortunately, not all of my friends were like Helen. Gemma was another girl that I hung out with. She was a cute blonde with a great personality. She was funny and always had a good comeback; while she wasn't in the best cliques, she was certainly well liked.

Ken and Helen started going out, and after seeing them together for a while, it made me realize that I wanted to ask Gemma out. However, before I did, I decided to ask my mother about it.

"Mom, how do I ask a girl out?" I asked her.

"Are you interested in someone in particular, or is this a hypothetical question?" she asked.

"Gemma," I told her.

My mother had met Gemma when she had been over. I sometimes, though not often, had a group of friends over. We had a nice house and a pool, so my friends enjoyed it, but I wasn't always comfortable, because I felt it impinged on my domain. When my friends came over, which I always announced beforehand, my mother made sure that she and Girl were dressed in a much less revealing fashion and Girl behaved quite differently. It wasn't that I minded the style of dress or the behavior, just that it felt dishonest, as if we were putting on a show. As a result, I didn't have them over often, but on occasion, they did visit.

"Gemma's very nice," Mom told me. "When did you decide you wanted to start dating?"

"Well, Ken has been dating Helen for a while, and he seems to like it, so I thought it was about time for me to start dating," I replied.

"Ken and Helen?" Mom exclaimed. "That seems like a weird couple."

"I know," I said darkly.

"So now that your friends are dating, you feel you need to as well?" she asked.

"Well, I'd like to see what it's like, and I do like Gemma a lot," I told her uncomfortably.

"That's nice," she said with a smile. "I think the best thing to do is to just tell her that you like her and that it would make you happy to go out with her."

"OK," I said. It made sense, and I thought that Gemma would say yes.

"Before you ask her, though, you should talk to your father," my mother told me.

"Why?" I asked.

"Well, I think he wants to give you some advice," she explained.

Later that night, after my father came home, I told him my plans to ask Gemma out.

"My son is growing up," he said with a smile.

"Dad!" I complained.

"That's OK," he told me. "But I'd ask that you wait a month or so to ask her out."

"Why?" I asked. I didn't think that I was patient enough to put this off a month, now that I had decided to do it!

"Well, I gave you access to Girl so that you'd feel more comfortable around women," he explained. "Girl, however, is not a good model to base a dating experience on. You will find, as I'm sure you know, that she is not at all representative of the girls that you will be dating. What I'd like to do is set you up on a few dates, let's call them practice runs, with a woman who will behave more like a real date would behave."

"I guess," I said, though I was disappointed that I would have to wait to ask out Gemma. "Why do I need to do that? Will it be someone my age?"

My dad smiled and shook his head. "For my purposes, an eight grader would be totally inappropriate. No, the girl that you will be dating is a friend of mine named Katherine, and she is eighteen years old."

"Eighteen?" I asked in surprise.

"Yes," he told me. "The person needs to be of legal age to make decisions for herself, and the perfect girl is a little older than you. However, she will try and act like an eighth grader. You know - immature."

"Dad!" I whined again.

"As to whether you need to do this, the answer is no," Dad said. "However, my advice to you is to take me up on this offer. You will be asking Gemma out for the first time. You will be dating for the first time. Certainly, it can be fun and interesting to experience the dating experience as a novice, but I think that you'll find that if you do this dry run in a non-threatening environment, when you do finally ask Gemma out, things will go much more smoothly. You'll be confident, because you will know what to expect, and as a result, Gemma will have a better time."

I rolled this around my mind. Certainly, an eighteen year old would be very sexy. However I wasn't sure that it would really be the same as dating someone in my class. Nevertheless, my father's ideas had been quite satisfying in the past, so I agreed.

"Let me just warn you," my father told me. "After each date, Katherine will provide me with a critique. Don't be offended; just think of it as a learning experience. She'll tell you what you did right, and what you did wrong, and you'll be able to correct for the next time."

"Great," I thought. "Another class."


That weekend, my Mom drove me to meet Katherine. Though Katherine probably knew how to drive, she was playing a girl my age, so Mom was driving us to the movies. We stopped at her apartment and I went to the door. I knocked on the door, and a girl opened it.

"Katherine?" I asked.

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