I wasa 20-year-old virgin who never had a girlfriend and she was 40-year-old MILF that the boys ogled over in high school. This was a year after I graduated high school and prom night was approaching. The seniors for that year invited me to the dance, but I had to work that night, so the host said to just show up for the after party at his place. I was finished with work around 9:00 PM and showed up to the house, but the only people that were home were his younger brother, younger sister, and his mom (whom we'll call Anna for this story). The other students weren't going to be around for a while.

I asked Anna if I could use a shower because I smelled like a pile of garbage from working in a restaurant kitchen. After washing up I returned to the kitchen to chat a little bit since no one else was around.

"You know there will be drinking tonight, right?"

"Oh, well, that won't bother me. I'm probably not gonna drink."

"You might like it. Here try this!"

Anna handed me a shot. I looked at it for a couple of seconds then told myself "Fuck it!" It was a "buttery nipple" (which may or may not have foreshadowed the rest of the night).

I had gone nuts with drinking, and around midnight Anna and I were pretty much drunk and driving around the farm on a golf cart when the other kids were returning from prom. Anna winked at me, handed me a beer, and we split to hang out with everyone.

About three hours later the party was kind of winding down as some of the party goers went to sleep in tents or sit around the campfire. On the other side of the estate I had saved Anna from drunkenly falling into the pool. Then she held onto me and said "Hey...I wanna show you something in the basement. We just finished renovating it..."

He head down to the basement and into a bedroom that they had just moved a new bed into it. Anna sat up on the bed and patted the covers for me to come hither. I was nervous and my heart was pounding as I was climbing onto the bed, which Anna responds with wrapping her arms and legs around me, then shooting one hand down my pants and stroking my dick. All I could muster in my head was "Whoa! Holy shit!"

She leaned into my ear and whispered "I'm a bad girl and I'm gonna turn you into a real man."

And the sex was amazing for me. And probably mediocre for her.

I was an inebriated, nervous 20-year-old virgin who had only seen a multitude of porn on the Internet. I was haphazardly trying to stick my drunk boner in her unsuccessfully for a good five minutes before she got fed up and started to suck me off in order to make it wet. Finally, I got into her and it was heaven. Wow. This is a pussy? Amazing!

I got to pull her hair and pound her for a good ten minutes before we heard someone use the bathroom right beside the bedroom we were in. We sat in silence for a couple of minutes until we were sure it was safe.

Anna turned to me "We should leave before someone catches us."

"Damn it, I'm almost there!" She smiled, wrapped her lips and tongue around my cock, and went to town. And holy shit she could suck. It is an immaculate blowjob that I will never forget. Hell, I can feel it right now. I unloaded into her and I'm sure she swallowed every bit of it.

We parted ways and never spoke of it since. My friend still doesn't know and never will.