Encounter #1

For reasons I will eventually describe on the blog, my first Craig's List encounter was EXTREMELY lucky. Basically the equivalent of your hot high school teacher asking you to stay after class, and then fucking you on her desk. Well, in that neighborhood at least.

So what made this encounter so lucky? Very simple....I was actually responding to a post made by a real woman!! Yes, I'm serious. How rare is this? It deserves its own post, let's put it that way. Anyway, it was a post made by a 42 year old female, saying that her husband was away, and she needed a quickie that afternoon. Preferred a younger guy (raises hand!). Didn't leave a name, and I didn't need one....anonymous was good. I read it at the right time. Responded I was interested (more on how I responded in later posts....but very important). She responded back. Exchanged pics. She looked very MILF-y. We were at the hotel together about 3 hours later.

Now, I didn't know what to expect by any means. Anyone can send a bullshit picture. Was I meeting a woman far less attractive than her photo? Was I meeting a woman at all?? Would anyone show up?? Leap of faith, my friends. But then she arrived...knocked on the hotel room door....and she was just as her picture promised. 42, curvy in all the right places, wearing a sexy, short skirt and tank top. I began to attempt fumbling through some small talk, but she spared me. She had no interests in chit chat.

She walked up to me and kissed me...forcefully. We kissed passionately for what seemed like hours, before we made it to the bed. Taking each others' clothes off as fast as we could, and tossing them randomly around the room like you see in movies. I kissed down her body slowly....up and down her thighs. Finally, I began to taste her (something I LOVE to do). My oral assault lasted quite a long time. She was very responsive....moaning loudly, and even squealing at times. And that was all before I slid a finger inside her.

She then reciprocated. Her skills were amazing (alternating slow and fast, short and deep), and I had to stop her before ending things too quickly in her mouth. I wanted more.....I needed to be inside her. I quickly ripped open the condom and put it on, and then slid myself inside her. In and out. Slowly at first....gradually faster and harder. Her moaning was making it impossible to hold back. Eventually she began a loud crescendo of moans, and I lost it....cumming as hard as I've ever cum. She laid next to me....still breathing heavy, sweating slightly. She grinned at me seductively and kissed me lightly on the lips. "Thanks". With that, she got up, got dressed, and with a last wink and smile, promptly left the room.

I was left to myself. As I laid on the bed reflecting on the experience, I only had one thought in my mind......what the fuck took me so long to use Craig's List? Could getting laid actually be any easier??

You see, I didn't realize how lucky I was then. But before long, I would learn.