Tales of a Driver: Social Security
Working at the Chicago style grill was great and I made friends with all the workers including the owner and his son. I was allowed to make whatever I wanted I would even take my own orders, make them then deliver them. It was Friday and I received my cash and was about fifteen minutes from leaving when I got a call.
“Chicago style grill J.A. speaking”.
“You haven’t forgotten that you own me have you young man”? Maggie’s voice pierced though me. “No Mrs. Uh Maggie I have not what can I get you?” I stuttered out. “I just want some company don’t worry” she said softly. “Bring me a small cheese pizza and yourself”
Often at the end of the night, I would pay for the delivery out of my own money so I could deliver the food then just go home so this is what I did.
On the way to Maggie’s apartment a queasy feeling came over me, she was pretty attractive for a mid-40 year old but this was to weird. I arrived at her door and she opened it, to my surprise, there was no one else there and she was wearing a housedress, nothing kinky, all normal.
“I’m glad you came, I bet you thought I wanted something else” Maggie chuckled. “I just wanted someone to share my pizza with that’s all” she then got up and grabbed some wine. “What I want to teach you is how to really treat a girl” “Women like to be treated well and they like an adult not a child, someone they can talk to and be with” She then poured me a glass of wine.
I am sure now that I drink wine myself it was a really good wine but at that age it was bitter but strong. “Thank you Mrs. Maggie” sounding like a scared little boy. She told me that she has always been a flirt and that during the war she would meet sailors and such and show them a good time.
The war?! Wait a sec how old is this lady? She then told me that when she moved to Chicago she joined a swingers club and it was fun at first but was a bit to public for her likes. She then started her own “club” with a few select members. She told me she has been doing this for twelve years.
I didn’t even realize we had drunk the whole bottle of wine and finished the pizza. “Do you want to see some pictures” she asked. Then lead me to her bedroom. She showed me pictures of her with all types of different guys and locations, this lady was well traveled.
She put her hand around me and kissed me and told me “I was a good listener” I know I was drunk because I really couldn’t move. She began to make out with me and I was in no condition to stop her, I guess I didn’t really want to either.
She had a good body for her age, again if you have ever seen Christmas with the Kranks think of Jamie Lee Curtis’s body in that movie. I didn’t feel scared anymore, while the term MILF wasn’t used at the time I was in an encounter with one. This is a good thing right?
Then she told me to hold on for a second and grabbed a condom out of the dresser, come to think of it she had tons in there.
Then she took her teeth out.
The war she spoke of was World War 2 meaning she was not 40 something more like 60 something. No matter how much my mind wanted to leave my body could not. I don’t wish to go into any other details and I am sure most don’t want to hear them but needless to say she had her way with me.
She told me I did well but she could help me in a few areas. I told her that I had to go. She then gave me another hundred for the food and told me not to be a stranger. I never heard from her again and was too afraid to look her up. I don’t even want to think what number I was in the line of guys she has “pleasured” but it did happen and I did learn something, never get drunk with a sex crazed old lady.
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