Chapter 3: In for a Penny, in for a Pound

When I was sixteen I still hadn’t been with anyone other than my brother, but we did it nearly every day. Several times most days. I would never have considered it excessive, although I have since found out my sex drive is well above average.

In fact my sexual desires only became stronger over the years. I would become noticeably wound up if I missed sex for one day. Once a month I’d even experience a day or two when, if given the choice, I would have a penis inside me all day long.

Most of my life I have had sex at least three times per day on average. I’ve been very lucky in always having one or more partners who could cope with this. I guess I tended to seek out people with compatible sex drives.

Despite my strong sexual appetite, I really never felt the need for anyone else in those early days. I had a penis ten paces from my bed that I could almost have any time. He could never turn me down. I could get him hard just by licking my lips, cupping my boobs, or stroking a finger across myself suggestively. I was never left wanting for an erect penis.

I would say I learned a lot about my body, and about his. But then, to be fair We both had a lot to learn. I especially had to teach him how to touch me because he had been completely clueless.

That was when I learned the single most important lesson I’d ever learn about sex. Communication was EVERYTHING. Neither Matt nor myself knew virtually anything all about sex.

The problem was neither of us had the first clue how little we really knew. What we did know to some extent was our own bodies. When we shared what we liked it always made everything better.

Quickly we learned more about each other and our experiences got continually better. There was still so much to learn and we really knew next to nothing.

He was fairly adventurous though, and once surprised me by putting a finger in my ass. I had been riding him facing his feet, because he really liked to see my butt while we fucked. It had felt really great having his finger up there while his cock was also in me. I think it probably got me there a lot faster too.

For my part, I never would have suspected that his reaction would be so much more profound. It had been awkward to reach, but a few days later I tried to reciprocate. I was leaning way back on his cock, bracing myself with hands on his knees. I had been finding I liked the way this made his cock touch me inside. Barely able to reach, I spat on my fingers and reached for his ass.

He really resisted it at first, but I pushed into him. It was hot inside. It was like a vagina but tighter. I think I got to a little past my second knuckle when he went crazy. He gasped every time I moved my finger even slightly. That’s when I began to move it real fast.

The noises he made were bestial. He came in me about fifteen seconds later. From that point on I made sure to always use that trick anytime he was taking too long. It never failed to make him come fast.

It was a few months after my sixteenth birthday that I finally had sex with another boy. There were several cute boys at school and they were really friendly with me. I would fantasize about convoluted circumstances where they would discover they found me attractive. Then they would get hard and need to give it to me.

There was one boy in particular I’d often seen at the library while Matt and I used the bathroom. I daydreamed that I would help him find a book he wanted and he’d fuck me in a corner while I tried desperately to keep quiet.

One day with Matt’s semen soaking my panties I walked in there and picked a random book. My post orgasm high had driven away all anxiety and apprehension. I sat directly across the table from him and smiled what I considered a coy smile. He glanced at me and I said “Hi.”

He merely repeated it back to me and went right back to reading his book. Fifteen minutes I sat there getting horny despite the come dripping from me. I never got another response. Eventually the silence made me feel acutely self conscious and I departed. If only I had thought to ask him what he was reading.

That evening and the next few days I masturbated imagining him fucking me on those books. I was possibly getting a little too worked up. It would have been fine if a few days later my live-in penis wasn’t about to abandon me.

Matt was away the rest of the week at camp, I’d been wanking every day but I already missed his cock. I thought I was alone in the house. I’d been using my toothbrush for about five minutes when the battery ran out. Frustrated I lay there catching my breath cursing the world for conspiring against me.

I’d been stalking my library boy and had already found his phone number in the book. I was seriously considering calling him at that moment, my pussy was desperate. I was already walking towards the phone when I convinced myself it was insane. I decided instead I needed a glass of water, perhaps even a bucket. My mind was weighing every possible option, seeking a way to make him fuck me.

I heard some noise and discovered Luke was drinking beers and watching a horror movie. He had broken up with his girlfriend a couple of months back and had since been drinking a lot.