Some of My Best Experiences

It's not too often that I write about masturbating by myself. Usually my stories involve someone else, but I thought I might share some of my favourite masturbation sessions that I can remember in the past.

The first one that I can remember vividly happened when I was about 13. We had some guests staying with us that lived quite far away, so they were staying overnight too. The family had three daughters, one that was 13. The other two were much younger, but the daughter, Tegan, was very good looking and I was interested in her from the start.

After a few days of her being there, we hadn't really talked much since I was too shy. It was just me, her and my sister there for a few hours since the others had gone out for a while. We'd decided to go swimming. While we were swimming, I got a good look at her in her swimming outfit, which showed off her body. Needless to say it gave me a rather obvious erection. I tried to inconspicuously relieve myself under the rippling of the water by lightly rubbing my dick through my swimming shorts while watching her, but I became too self-conscious. I quickly ducked back inside without Tegan or my sister really noticing. I dried off and went into my room and locked the door.

My room faced the pool at the back of the house, so I could see her swimming through the window. Luckily my windows were tinted so she couldn't see into my room with the sun shining directly on it. Now this was when I was 13, so I hadn't learned how to masturbate with my hand at that point. I was masturbating regularly by humping my pillow. So as was my habit, I opened my curtains up so I could see Tegan and picked up my pillow. I layed it on the side of my bed, took off my still-damp swimmers and started humping the pillow. I imagined that it was really Tegan beneath me as I thrust into the pillow. It only took a few blissful minutes before I was ready to cum. With a final thrust I moaned out her name as I came onto my pillow, all the time watching her through the window.

After that I quickly wiped my cum off my pillow and dick with some tissues, put my swimmers back on and went back out to swim in the pool. Tegan was none-the-wiser, but like most people I wish I'd had the courage to express my interest in her while she stayed with us. Maybe that masturbation session could've turned out different.

Another memorable incident for me was a couple of years later when I was 15. I'd moved to a new city and was starting to get confident with talking to girls. I had a crush on this girl named Chloe who was in my Maths class at high school. After she became my girlfriend, I remember a phone call that we had that lasted for a few hours as we shared some personal information to each other. We started talking about the difference between boys and girls. She started talking about Wet Dreams and how she wished she could experience them. She asked me if I'd had any and I, honestly, told her that I'd had one a few weeks prior. She started pressing me for details about how it felt and what I did after I realised. I told her that I didn't really feel anything, just woke up feeling relaxed with a mess in my bed.

I eventually started skirting around the topic of masturbation with her. I wanted to ask her whether or not she masturbated, but couldn't quite come out and say it. She kept pressing me with more than a giggle in her voice until finally I asked her directly. She told me she'd never done and never really saw the need. She asked me if I masturbated, whic shouldn't even really be a question to a 15-year-old male. I told her that I did, and after already having an erection for the good part of an hour while talking to her, telling her about my masturbation secrets only made me more horny than I'd ever been to that point.

She eventually had to hang up the phone, and before she did she told me to 'enjoy myself' and quickly hung up. Of course she knew what I was going to do afterwards. At this point I'd learned how to masturbate with my hand and lube. So after I hung up, I pulled off my shorts, got my lube out and layed back on my bed. As I replayed the conversation I'd had with Chloe in my head, I took my dick in my hand and started stroking it slowly. Despite being incredibly horny for such a long time, I managed to make the session last for quite a while. The feeling was euphoric as I slowly stroked myself with my eyes closed, imagining it was Chloe. I didn't even really feel a need to cum, it was this constant nice feeling as I stroked away. Eventually I decided that I wanted to cum, so I stroked a little faster and within a minute I was having one of the best orgasms of my life as my cum spurted out onto my stomach and hand.

I laid there for a little while just enjoying the relaxing sensation and eventually dozed off with my hand still on my dick and cum still on my stomach. When I woke up a few hours later it'd dried and I had an awful time trying to scrub it all off. I was lucky nobody walked in on me like that.

When I went to school the next day, When Chloe saw me, she gave me a knowing smile and I just winked back to her. She knew what I'd done, and it remains one of the most memorable masturbation sessions I'd had.

Well, those are a couple of my best experiences. I have some more which I'll write out at another time. Writing about these experiences has been more than enough to make me want to masturbate over them again. So I'll go do that and hope you all enjoyed reading about them.