This story is a work of fiction. All characters are over the age of 18.
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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."
I was too stunned to comment. I almost pinched myself to make sure I wasn't dreaming. Still staring at her, I picked up my drink and finished it in one gulp. I threw some cash on the bar, got up and helped her off her stool, and out the door we went.
I walked her to her car and opened the door for her. She thanked me, kissed me on the cheek, and said "follow me young man," then she got in the car, giving me an incredible view of her inner thighs and stockings as her skirt rode up while she slid into her seat.
I had to take a few deep breaths to calm down as I followed her to her house. When I parked behind her in the driveway, I rushed out to open her door for her. She smiled and I was rewarded with another great view between her legs as she took her time climbing out of her seat. She knew what she was doing and she did it well, giving me a glimpse of matching lacy black panties.
She led me in and had me take a seat in the living room while she went to the kitchen to fix us drinks. I sat there waiting, looking around at a very expensive home. Rich leather couches, plush wingback chairs, mahogany furniture, and expensive looking paintings and collectables all over the place.
She walked in with drinks, handed one to me, and placed hers on the coffee table. She smiled at me as she slowly took her high heels off and sat down on the couch beside me. She picked up her drink and crossed her legs while looking at me. "Are you wondering why you're here Jack?" she asked me.
"Well," I replied nervously, not sure exactly what to say. "I'm hoping to have sex, and I think you want that too, for your own reasons though."
"You're cute AND smart," she said while staring at me. "I'll be honest with you Jack. I'm pissed off at my husband, and I want you to fuck me. Then I'm going to tell him about it," she said, watching me and waiting for a reaction.
I didn't reply, so she went on. "I've seen how you look at me in the bar, and I've seen the women you've hooked up with, so I know you're interested. I just need to know if it bothers you that I want to, uh, well, use you I guess."
I just smiled as she talked. This was turning out better than I could have imagined. I wasn't worried about her husband physically, but I didn't want to get killed either. "Does he own a gun?" I asked, being serious but smiling at her.
"Oh God no," she said, and laughed. "He's as meek as they come. He just got lucky his young secretary is fucking him and he thinks he's cock of the walk. I'm going to tell him everything you do to me, and everything I do to you," she said as she sipped her drink. "So, what do you say Jack?"
Letting my eyes drop to her cleavage again, I smiled and said," I say show me your tits and let's get this party started!"
She burst out laughing as she stood up and put her drink on the table, and proceeded to unbutton her blouse and take it off. "I like your attitude young man," she said, as she unhooked her bra and took it off. She dropped it on the table and stood in front of me with her hands on her hips.
Her tits sagged with age, but were still full and round (38D-I checked her bra later) with large areola and nice nipples. I stood up and held them with my hands, squeezing and massaging them as she watched me. "You like them Jack?" she asked, holding my head as I leaned down to suck her hardening nipple.
"Oh yeah, very much Marie," I said, as I sucked one, then the other, feeling them get hard in my mouth as I squeezed and kneaded her big tits, causing her to moan and reach for my shirt, pulling it up over my head and off.
