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It is a pretty long story so sit back and relax. I'll spare you all the minute details since that would turn this into a short novel, but here goes. When I was at around 16, a neighbor lady that I was constantly helping take out trash and things like that, took a liking to me. She became really close friends with my mom. The reason I use to help her was because my mom wanted me to learn to help others expecting nothing in return, help your community, blah blah blah. That and her husband had left her a couple years before we even moved into the area and her son was a lazy ass and spent most of his time with his dad. At first it was a pain in the ass, until I found out she liked to walk around barely clothed in her house. Next thing you know, I'm helping her out as much as I can (obviously). I'd get boners and even jerked off in her restroom a few times. Once, I was damn sure she heard me cumming, which she would later confirm. Since that day I began to notice that she would insinuate things and make double entendres quite a bit, and I really enjoyed it. I wasn't sure whether it was my wishful thinking or real, so I assumed I was reading too much into it and put those crazy thoughts out of my mind. Or, at least, I tried to. I didn't know why, but one day she flat out asked if I thought she was hot. After mumbling like an idiot and stuttering my ass off, I finally said "Yeah". Then she asked, "Would you fuck me?" I didn't know how to answer and just remained quiet. She asked again and I froze. Right then the phone rang and interrupted that so I let out this shaky breath that I had been holding in apparently. So here I am, 16 and horny, thinking I had lost my chance. To be entirely honest, it actually seemed like the things I enjoyed and turned me on so much began happening less and less often, which made me think I had ruined my one shot and pulling off the golden milf(just made that up). So the summer comes around and my parents are going out of town and I refused to go(boring family trip). They decide to let me stay home with my older sister. My lady neighbor's son, who was rarely home and usually with her ex-husband, decided to spend the entire summer with his dad as well. Before he left, she had bought him a Nintendo 64 (or maybe it was a playstation? He had several consoles over the course of our time together so don't remember which it was first). I see now that was an attempt to buy his affection, which did not work at all. That dude was a grade-A asshole. I used the console as an excuse to spend a lot of time at her place, even late at night. My sister really didn't give a shit anyway. So the second day my parents were gone, I'm over there playing games and she goes in her room for a pretty long while and comes out in pretty much undies, or "workout clothes". I'm sitting on the couch (that sitting where you slide your body halfway off the couch) and she sits next to me. I keep glancing at her and it gives me a boner. The BDSM gods must have been smiling down on me because on this day of all, I chose to wear basketball shorts which I didn't normally use unless actually playing basketball. Today though, I wore them and they were these really cheap ones the school gave us for the team so they were really thin. My boner was as prominent as it could be. She saw it and said, "so I guess that means you would fuck me?" I said no at first but she seemed hurt. What followed was a back and forth of myself letting her know she was smoking hot but that I didn't want to get in trouble and her trying to pry out of me what that meant. I guess she just wanted to hear me say it. Have you ever had such an adrenaline rush that you start getting dizzy and can feel everything? I mean everything like even the slightest breeze on your skin? That was me in this moment. I was freaking out, afraid of saying I wanted to fuck her. I was sure this was some secret plan by my mom to catch me being a horny SOB. Finally, I figured the risk was worth the reward, and said it. "I've wanted to fuck you for a long time." She took the first step and we kissed. That day we fucked for the first time. Not my first time, but it was my first time with a woman as hot as her and a milf. It was nothing special, I must confess. No super gifted love guru here. Don't get me wrong, this was awesome for a guy my age but that is not the important part, at least not for now. After a few encounters like that which didn't last long, she began to introduce me into being a submissive. Nothing to sudden just firm orders here, a slight spanking there. It started with subtle things which I passed off as her just teaching me "adult sex". I didn't know anything about BDSM so how was I supposed to know? She then told me about it. About submission and what it meant. She said she was a switch and wanted to dominate me. At first, it did freak me out a bit. It was something I had never heard of before. This was the 90's so I hopped on that dial up AOL and searched the crap out of BDSM. I read all I found and learned everything I could about it. By the end of the summer, I knew enough to start searching for more information on my own on Yahoo! (those were the days!) and in chat rooms. I decided to try it out and let her be my Domme. She gave it a shot but it quickly became clear that I wasn't the submissive type. It felt wrong and uncomfortable. When she would ask me to kneel, I couldn't bring myself to do it and she could tell right then that I was not enjoying it. What she did next, changed my life. She took a tie (not mine), wrapped it safely around her neck and bent over. She told me to fuck her while pulling on the tie. I did so and it just felt right. I learned as much as I could, as fast as I could. The motivation behind it was at first my fear of losing her attention and not getting lucky anymore. After a while, I began to learn so much about the lifestyle that I began to feel like it was where I belonged. I learned from others and, eventually, talked to her. Like I said, she was older so I thought she was going to shoot down the idea of me being her Master, if only to learn. She hesitated but ultimately agreed. That was the beginning of what would be an awesome relationship that ended abruptly after I lost her in a car accident a couple years later. That's it. That is how I got my start in BDSM. freddicusthegreat