I had thought about it a lot. It would start crossing my mind at random times during the day and I would dwell on it, and play it out in my head. I had always turned away his advances, but I wasn't about to anymore. I started to want it, began to actually crave it. It was worth every second.
We had known each other since our junior year or so in high school. I mean, we'd always been at school together, but never really talked until then. We started to hang out more frequently, go to shows downtown on the weekend, and hang out for a few hours afterwards with the same group of people every time. I had even spent the night at his house a couple of nights, and back massages from him were frequent, and always the best. His feelings became known to me very quickly, but I always looked away. I was with different girls through high school, and he was always in my life in a certain way ever since we met.
After high school was over, we maintained contact on and off over the years. Social networking played a key roll. I went off and started my life, he started his, and we stopped talking for a few years. All of a sudden, after what seemed like an instant, 3 years had gone by, and my life had taken a very bad turn. I moved back home and started over again. We started talking on and off from time to time more often, and slowly worked back up to actually hanging out at late hours of the night, smoking cigarettes and talking. Then the back massages started back up, and I was hooked.
I would start coming over more frequently, and always received an amazing massage in return. Not that I was using him for that at all, I very much enjoyed having someone to talk to, hang out with when the lights went out. We were both always night owls, and having someone to talk with when you could have intellectual conversations was nice. The back massages were simply more of just something to do really, but weren't in any way expected. He never pushed his limits too much, but still managed to make his intentions known. I respected that a lot. It was eventually a main reason I chose to.
I had gotten off work, knowing full well what I was going to do that night. I wasn't going to let anything stop me. I stopped by some bars with some other friends, had a few drinks and went home to play some video games and wait. Around midnight, I got in touch with him. We made plans to meet at his place and hang out. I got on my sweatpants, a hoodie, and made my way over. We stood outside for a little while, smoked a couple of cigarettes, and talked. It was fucking freezing outside. The middle of February and we had just gotten a hell of a snow storm. We were both cold as hell when we finally made our way inside and to your living room.
We watched T.V. for maybe an hour or so, keeping light random conversation. I start to yawn and stretch and he asked me if I wanted a massage. I nodded my head and asked him where he wanted me to lay down, and he had me follow him to his room and pointed at the floor. I obeyed, and took off my hoodie, and lay on my stomach, on a towel he had lain down for the oil he was going to use. He was prepared, and so was I. He began how he always did, at the shoulders, working his way down and back up my back. Then he would spend a bit of time on my lower back, pushing at the top of my pants, which was where I usually made known I wasn't ready. This time, as his hands pushed down on the back of my pants, to the top of my ass, I lifted my hips into his hands. He got the idea, and slowly pushed his hands under my sweatpants and started massaging my ass. I helped him push my sweatpants down a bit, exposing my entire ass to him.
