It was the summer after highschool. One of my friends parents had just bought a big beautiful house around the corner from where I lived and we were all excited because she was the cool mom. She let us drink and party all through highschool and now most of us we turning 19 and we could legally drink (up here in Toronto).

We had a few parties and she bought us alcohol, gave us weed when we needed it and even gave us condoms and let us bring girls over to fuck in the basement if we didn't have a place to go. I guess it was her way if keeping an eye on us making sure we didn't get too fucked up or anyone pregnant. Either way we could almost do anything under her supervision. It was great LOL.

I grew really fond of her. She kinda grew really fond of me. She was short, probably 4'11'', with a slim build. Really small tits but a fantastic ass for a 44 year old. She always had glasses on, which gave her the hot librarian vibe but she drank and swore like a sailor so as soon as she opened her mouth you were stunned by how powerful and dominant such a small woman could be. It was hot. She wasn't the MOST attractive woman but when you're 19 years old even a breeze will get your cock hard.

As the summer went on I kinda noticed that she was into me. I would come over to swim and she would check me out. Or our conversations would always somehow end up turning sexual. She would usually join in on the drinking so it wasn't hard to take the conversations there. I was dating a girl at the time but she wanted to take things slow. I was a late bloomers and had not had sex yet. So I decided the next chance I got alone with my friends mom I would try to push things to see if she was interested in fucking.

One night I got my perfect opportunity. We were all drinking at her house, and my friends decided to take the party to another friend's house because he had a hot tub. We all agreed but one the MILFs son (my friend at the time) was too drunk to leave. So I told everyone I would stay back to make sure he got to bed safely and everyone left.

My friends mom was upstairs watching TV alone. So when I got my friend to bed I got went upstairs and found her sitting alone in the couch with a beer in her hand. She was wearing black sweats and wrapped up in a cozy blanket. I told her that her son had gone to bed and that I didn't want to leave with the rest of them. She got up, sat with me at the kitchen table and offered me a beer.

We got to talking, about what I was going to do now that I was out of highschool. I told her I had been working with my dad for a year and I was thinking of becoming his apprentice. Once the conversation slowed down she asked why I didn't go with my friends to the hot tub party. I saw the opportunity to take things where I wanted them to go so I told her that the friend who has the hot tub has a super hot mom with huge tits and I was embarrassed to get a hard on with my swimming shorts on. She laughed for a bit and then stopped, glared at me and asked if I would ever fuck an older woman. I replied "of course" as MILFs are and always will be my favorite.

She grinned and asked if I had already turned 18. I pulled out my license and showed her that I was in fact of age. She smiled, and told me that we could most likely have a really fun end of the summer together but, that she was tierd and wanted to go to bed. She showed me to the door and opened it. As I went to walk away with a big frown of disappointment she turned me around. Grabbed my cock and balls and started making out with me. She had the scent of liquor and cigarettes on her breath which to this day instantly gets my cock hard.

Before I could do anything else, she pushed me away and said "that's a enough for now, have a good night" and pushed me out the door. My heart was beating at 1000 miles per second as I stumbled home with a rock hard cock.

That was the start of the best summer of my young life. Let me know it I should continue this series....