This story is a work of fiction. All characters are over the age of 18.
*
My name is Jack, I'm 23 years old, and my nickname among my friends is "Grandson." It's their way of teasing me for being a "granny chaser" as they like to put it. I don't have a problem with it at all. I love mature women. I have been obsessed with them ever since I saw a spread of pictures of older women in a porn magazine when I was 14 years old.
I hang around a local bar that is a known haunt for the older crowd. I started going there as soon as I turned 21 and could legally drink. It has a U shaped bar that can seat about 25 people, and some tables and booths along the back wall. I would sit at the bar and wait for a chance to chat up an older woman. I stuck out like a sore thumb, but after a while they got used to me.
I've had some success over the past two years. I dated a few different ladies, had some hot make out sessions in cars, brought home for sex, that kind of stuff. To me it's a gold mine, and my regular hangout.
From the first week I started going there I would see an older couple. They would come in a few times a month to eat and have a few drinks. They always sat in a booth against the wall. I figured they were both in their 50's, maybe lower 60's. He had white hair and usually wore a suit. She always wore a dress, and always just above the knee. Her hair was white also. She wore lots of jewelry and always had a string of pearls around her neck that hung down between her breasts, which were always showing some cleavage to one degree or another.
Needless to say I would watch her like a hawk every time she came in. Any time she looked over at me I would smile, usually not getting one in return. She would look, I would smile, and she would look away. I made it a point to walk by her booth every time she was there, and stare at those pearls hanging between her breasts. Some days the cleavage was nice and wide, other days not so much. It was always a nice sight no matter how much she was showing on any given night.
I had not seen them in the bar for over two weeks. Then a few nights ago she came in alone. I was sitting at the bar with my drink. It was a quiet night, maybe 15 people in the place, most of them sitting at the bar, with a few couples at the tables having a bite to eat. She was dressed as usual, with a nice amount of cleavage on display, and my eyes were glued to her as she crossed the room and pulled up a stool at the bar, right across from me.
I looked back at the door a few times, waiting for her husband to come in, but he never did. She ordered a drink and drank it down rather quickly. She waved the bartender over and ordered another one. She looked across the bar to see me staring at her, and I smiled. She gave me a slight hint of a smile, and then looked away as the bartender approached with her drink.
She sipped her drink a few times, and then drank the rest of it in one gulp. I watched her as she stared off into space for a few minutes. All of a sudden it looked like she was starting to cry. She pulled some money out of her purse, dropped it on the bar, and got up and walked out the door.
I followed her outside and walked up behind her just as she was opening the door to her car.
"Excuse me," I called as she turned abruptly to look at me. "Um, are you ok?" I asked.
"No, I'm not ok!" she blurted out, and burst into tears. "My asshole husband is fucking his secretary and I kicked him out of our house!"
"Oh man, I'm sorry," I said, as I stepped closer, reaching out to rub her arm.
She started crying harder. "Yeah, me too," she said between sobs. I stepped closer and hugged her. She was holding her purse and keys in her hands and did not hug me back, as she cried and said, "I shouldn't have come here. I thought a drink in the bar would distract me, but it didn't."
I held her and said, "I'm sorry he did that to you. He's a jerk."
"Yes he is!" she cried out, and pushed away from me. "I have to go, goodbye!" Then she got in her car and slammed the door and drove off.
I went home too, feeling bad for her, but also wondering if this would be an opportunity for me. While I felt bad on one hand, I was still horny just thinking about her and fantasizing what might be. I got in the shower and had a hot stroke session while I fantasized about having sex with her. I fell asleep wondering if and when I would see her in the bar again.
Two nights later (last night) I was in the bar at my usual seat. She walked in, looked over at me, and walked up to the stool beside me.
She smiled as she indicated the stool. "Do you mind if I sit?" she asked?
"Of course not!" I said, smiling as I jumped off my stool, pulling her stool out to help her sit.
"Thank you young man," she said, smiling and extending her hand. "I'm Marie, and I want to apologize for being nasty the other night and thank you for being so sweet."
"It's ok, you don't have to apologize," I said, taking her hand in mine, bending down to kiss the back of her hand. "I'm Jack, and it's very nice to meet you Miss Marie."
"Oh my," she said, smiling as I kissed her hand. "Aren't you a gentleman, and it's nice to meet you as well Jack."
I took my seat and let my eyes take her in. She had on a little more makeup than she usually wore and no dress tonight. She wore a tight red skirt, about mid thigh, stockings and high heels, and a semi-sheer white blouse that I could see a lacy black bra through. Her pearls were resting between ample cleavage, and if she went through all this to impress me or turn me on, she succeeded in spades. I was smitten!
She was very aware of me staring, and she smiled, apparently pleased with herself for the reaction she caused. "Do I look ok Jack?" she asked, grinning at me.
"You look stunning!" I blurted out, smiling back as my eyes dropped to her ample cleavage. I looked back up in her eyes and said "I'd love to buy you a drink."
She stared in my eyes and spoke softly. "I'd love for you to finish your drink and come home with me. I have what I want to drink there."
