The first time my sister came into thoughts during masturbation was around ten years ago. I was 23 which would have made my sister, Trudy 20. At first I would be in the middle of the whole process and she would pop into my head. Then, after a while she became the reason I started masturbating in the first place. Before too long I was wanking off to photos of my own sister and imagining myself fucking her.
This became a regular thing and as the urges got stronger I would start to wonder how it would be to actually do it. I mean to actually cross that line and fuck my little sister. Once, after a night out on the drink I bumped into Trudy on my way home. We had a small chat and I started to feel my cock get hard. Before we went our separate ways I remember leaning in and kissing her on the lips. I was very nervous and I'm sorry to say that although I let the kiss linger slightly longer than a brother should kiss his sister, I wasn't brave enough to push my tongue into her mouth. I really wanted to and I've always regretted not taking that extra step. Would I ever get the chance again?
Some years later we had a falling out. I hadn't spoken to her in nearly 3 years but after I had some trauma in my life which I won't bore you with, we began talking again. I started to wonder whether I would again get close enough to her to attempt to kiss her again. Well, I have a story to tell you.
Trudy had come to see me and we didn't waste any time at all in opening one of the many bottles of wine I had got in and beginning to reminisce. I needed the wine to give me the courage to make the impossible move over this large taboo and I needed her to be nice and relaxed so she would let me. Time started to get away from us, the hour was getting very late and although I was still excited at the idea of seeing my sister naked I was getting very tired and I could see that she was as well. I offered her my bedroom and said I would take the couch and we went upstairs so I could loan her a t-shirt to wear in bed. I gave her the shirt and then I went off to brush my teeth. I was also using the time to psyche myself up.