I was 18yo at the time. My best friend was Jeff and we used to hang out together. His mom was a single parent, she had mental health issues he told me. Her name was Anna and she was very attractive.

Sometimes she wanted Jeff and I to have a few glasses of wine with her, we could always tell when she and her boyfriend were on the outs. Anna would get buzzed big time, Jeff said she took her meds and drank too, a big no no!

One night I went over to Jeff's house we were supposed to go see a band play. His mom opened the door and told me Jeff wasn't home, which surprised me because Jeff and I talked about going to see this band for days.

I was going to call Jeff but his mom practically dragged me into the house. She offered me a glass of wine but I declined because I was going to be driving and I didn't want any problems with the law.

Anna told me that her and Jeff had an argument and he stormed out the door. Then she started telling me her boyfriend was pissed with her as well. Now Anna was walking around with a glass of wine and a cigarette talking about all of this, the weird part was it was like she was just talking to the room she wasn't even looking at me.

So I decided it was time to go and I walked to the door and said goodbye. Anna literally ran to me and grabbed my arm begging me not to go. Her eyes were glazed, Anna was buzzing hard for sure.

She pulled me to the sofa and we sat down and she began to cry, I'm sitting there like I have no clue what to do. She said nobody loved her, etc, etc. She took a sip of wine and offered her glass to me.

Anna took a sip of wine and then she looked almost through me and asked if I thought she was attractive. I was shocked and even though Anna was very attractive, I had trouble saying she was. She stood up and twirled around in her dress. She apologized saying she looked like hell but Anna looked pretty hot to me.

I told Anna I needed to go but she grabbed my arm and held me on the sofa, she slid close to me quickly. Anna wore a lot of eye makeup and honestly I thought that was very attractive on a woman, not just Anna. She had on pink lipstick but it was faded now slightly.

I told Anna I really needed to go because I wanted to see the band. Anna jumped up and said she wanted to go with me. My mouth just dropped open, she jumped up and ran to the closet and pulled out a pair of heels and almost fell trying to put them on. I'm freaking out and don't know what to do?

She disappeared down the hall and I tried calling Jeff on the phone, there was no answer from Jeff. Anna appeared again and I could see she had put on a fresh coat of lipstick. She walked into the kitchen and I'm thinking about running out the door. Suddenly she turns around and the excitement that had been on her face was gone, tears suddenly ran down her cheek.

I asked what happened and she just walked over to me and put her arms around my neck and her head on my shoulder. We just stood there and her arms wrapped around me like tentacles, there was no way I was going to pull away like this.

We stood there for quite a while, I finally put my arms around Anna just to be nice. Her body pressed against mine and suddenly I felt the stirring of my young cock in my jeans. We stood there until Anna felt the bulge in my jeans, she pushed away just enough to be able to look down and see it.

She smiled and took my hand and led me to her bedroom. She reached behind and fumbled with the zipper of her dress. She was buzzing and couldn't get the zipper down. Anna turned her back to me, I knew what she wanted me to do. I unzipped her dress and she slid her arms out and the dress fell to her feet.

She was wearing a bustier with matching panties and black stockings and of course her heels she had just put on. She took my hand and pulled me to the bed. Anna lay in the center of the bed and God did she look good. She lay her head on a bunch of pillows with her head propped up and held out her arms to me.

I sat down on the bed and looked at her, my cock was steel hard. Anna mumbled something to me with this goofy smile on her face. I just sat there, Anna'a eyes seemed to be closing as I sat there deciding on what to do.

Thankfully Anna made the decision for us both, she lay there a few more moments and her eyes were closed and she began to breathe softly. I got up and looked down at her body. She was very attractive and I would have fucked her, but I wouldn't fuck her like this.

I reached down and pulled her heels off and took a blanket and covered Anna up. I backed out of the room and turned off the light. I called Jeff again once I was outside his house, this time he answered. He would meet me at the club as scheduled.

I never said anything to Jeff even though I told him I was at his house to pick him up. Anna never said a word but she always looks into my eyes deeply and smiles every time she sees me.