The Babysitter

It was the summer I turned eighteen and it was unforgettable. My parents separated before I can even remember. My mom remarried and moved to London. My dad would not allow her to take me with her...and smart lady that she is she did not want me caught in the middle of a very nasty custody battle. Instead they compromised. And I got the best of both worlds, Los Angeles during the school year and a much cooler English summer.

It became my escape after working my ass off to be what my dad expected; it was really nice to go there and not be expected to do anything, absolutely nothing. So even though I was eighteen now and an adult; I did not have to go, but when mom offered, I could not wait for one more escape before I faced the challenges of university in the fall.

Now things were not all glamorous there. My mom had had another child, but my baby sister was special needs. Her marriage fell apart and things were not always easy. But she made the most of those summers with me. She always found money and time to spend with me too.

That summer though was different for one reason: Kate. She was my little sister's babysitter. She was a couple of years older than me and finishing up university that year. She was studying to be a teacher and worked after school to give my mom a break. With my sister life was so crazy that mom usually had really exciting things to do when Kate came; things like the bank or shopping or another appointment to do with my sister. She always asked if I wanted to come too. But I was eighteen and gaming was way cooler than grocery shopping.

I got to know Kate during those times. I discovered that she was that rarest of creatures...a female gamer. Hell, she could even beat me at a couple of them. She even got me to go with her occasionally to take my sister swimming or the park. We would talk about games or school or life...which was pretty much gaming when you are a geek likes us. I really liked her.

Don't get me wrong, Kate was no super model or even all that pretty. She was a bit overweight and had skin problems. Like me (and most kids like us) she was not even into showers; let alone make-up and girlie crap. She was more like a friend...a female version of me. And that was cool.

Eventually, we got around to talking about what everyone our age does...sex. We discovered that we were both still virgins. And neither of us was too happy about that. That is when we came up with the plan: it was simple...have sex with one another.

The other thing that was amazing about my mom was how open minded she was. She, not my dad, had been the one to explain the facts of life to me. And she always took the time to listen to everything I said. So it might seem weird, but it was the most natural thing to talk to her about our crazy plan. She listened carefully without passing judgment. She asked a few questions: was I sure that I was ready, didn't I want to wait for someone 'special.' Then, of course, she had the condom talk with me again. She proceeded to go out and buy three boxes...and lube. That's my mom.

Kate and I waited until mom had taken my little sister to the park for a few hours. My baby sister was always kidding me about liking Kate anyway. But mom just told her that we were going to play games for a bit...with a wink at us as they closed the door.

My stomach got all knotty then. I mean in theory it had sounded awesome...have sex with my friend. But when you are both virgins, neither of you really knows how to get things started. Thankfully, Kate knew what she wanted. She started to strip off her old sweat pants and oversized t-shirt. Her tits were not that big so she did not bother wearing a bra. It was the first time I had seen breasts (other than my mom's when she breastfed my sister...and that don't count). I was fascinated with them, but she wanted to get on to other things.

She was the director on this set. She wanted to me to finger her. So I did. She was tight but wet too. She wanted to try a blow job. She was not the best, but how was I to know that? She was certainly enthusiastic enough. She probably formed my preference for wet, sloppy blow jobs that summer.

Getting the condom on was hilarious. We broke two. Good thing that mom had bought almost five dozen. One thing she had made clear: she was way too young to be a grandmother. We finally managed it though, getting that thing on my cock. It certainly was not because the condom was the wrong size; I have never and never will be a magnum guy.

Then it was time for the big moment. I admit it; I hesitated. Losing your virginity is a serious thing. Mom's words echoed in my head. Was I ready? Was this how I wanted to lose it? Did I want to wait for someone special? Two seconds later, I took the plunge.

I don't know what I expected but this was it. Better than Fifa World Cup, but not as good as the best game of Grand Theft Auto. To be fair, it was better than an average game of GTA. Just not as good as the 'best' one.

Kate seemed to like it. Better than me even. At least from all the noise she was making. She even told me so while we were playing GTA afterwards. I kicked her ass in that game too.

Of course, I was so nervous that first time that I did not manage to come at all. We went at it for over an hour, off and on, but I never managed to get off. Only when I was alone later on, thinking back on it and jerking off. But that orgasm was mind blowing. Like I had saved it all up.

That was just the start though. Kate and I had weeks to practice. The other thing that the Internet rocks at...besides gaming codes...is porn. Kate and I both had a bit of a porn addiction and got loads of ideas. There was not much we did not try that summer...feet jobs, anal, you name it. I learned to eat pussy too, but only right after swimming when she was really clean.

I got busy with my life after that summer. I never again spent a whole summer with mom. Sometimes I went a couple of years without visiting at all. But once or twice when I did visit I ran into Kate. Like me she had gone on with her life. Finished university, taken a teaching job, had a couple of relationships. We never did hook up again after that summer but we would laugh about the way we fumbled around as friends.

I took my wife and new baby to see mom again this summer. One afternoon we sat on the bench in that same park where she used to take my little sister so Kate and I could get it on. She looked over at me with tears in her eyes as she watched her granddaughter take her first step to her teenage aunt. "Do you have any regrets? You know? About Kate?"

That's my mom. Although it was my dad that raised me most of the time, it was my mom that I pattern my own parenting after...everything she ever did was about us. She thought everything through and put us first; right down to 'losing' me rather than put me through a nasty court fight. And that is how I want to raise my children...putting their needs first and worrying about every decision I make for them.

But she had nothing to worry about on that one. I put my arm around her and squeezed, "You always taught me: no regrets, Mom. And I believe that." The damned sun got in my eyes then because they started to get all watery. But that is my mom. And my wonderful summer with the babysitter.