Girl Scout Cookies

Walking up to the entrance of the supermarket, there were a half dozen Girl Scouts, and two tables loaded with Girl Scout Cookies. There was an older woman standing behind them, and when I got close to the tables to check it out, she smiled at me and said they were going to pack things up in few minutes. I knew a Girl Scout leader who once told me that the troop made more on a one-dollar donation than selling a box of cookies. When I mentioned it to the woman, she smiled and agreed with me. I told her I had no cash but would make a donation when I came out. She reminded me that they were shutting down in a few minutes before I walked into the supermarket.

Knowing time was short, I bought a bottle of water and asked for cash back when I was paying for my purchase, the machine offered options of $5, $10, $20 or $50. I chose $20, thinking I would get smaller bills. A $20 dollar bill was spit out of the machine, and I walked outside with it. Things were being packed up and put into boxes. The older woman recognized me, and, joking around, I told her that I only had the twenty-dollar bill and said I suppose I would have to give it to her. She immediately told me she had change, but I said it was a good cause and would donate it all. She thanked me, and asked if I wanted a receipt for tax purposes.

I went back inside to finish my shopping. There was a wine bar there, and while walking around I saw the same woman sitting at the bar by herself with a glass of wine. After introductions, we spoke for a bit, and then I sat down next to her to order a wine for myself. We chatted, and eventually ordered another round. I learned that she was a grandmother helping out, and the troop had been taken out for ice cream after everything was packed up. She had had enough of being around the girls and opted for wine instead. Although carrying a few extra pounds, her curves were nice, and her face always seemed to be smiling. She was a widow, and lived with her daughter, the Girl Scout leader. She was in her late 50s.

It was late afternoon by then, and there was a pizza parlor next to the supermarket. We walked over and ordered a pizza, and another glass of wine. It was a nice conversation that just flowed. When most of the pizza was gone, we exchanged phone numbers and agreed to meet again. I called her a few days later, and we met at the same supermarket wine bar after work. We ate some appetizers with the wine, and as we were leaving, she asked me if she could consider our meeting today to be a date. I told her it could be, and then she asked about the previous time also being a date, after the Girl Scout cookies.

Now I was curious why she was asking, and she told me that she was old fashioned and kissing on the first date was not something nice girls did. It took me a bit to figure out why she was asking that, but arriving at her car I understood. As she was opening her car door, I said that this was probably a second date. As soon as I said that, she gave me a kiss on the lips and climbed into her car. Before she shut the door, she told me that there were no more rules by the third date.

The next time I called her, she offered to come to my place and provide dinner. The “no more rules by the third date” was not mentioned again, but it was lurking in my mind, and we made plans for a third date at my place. She showed up wearing a dress and carrying a bag of take-out food. After I opened a bottle of wine, she served the food, and we enjoyed a nice meal. After, we took our wine to my couch, but were making out before we drank any more wine. I must’ve been too slow, because she took my hand and put in on her chest. Again, I was too slow, and after some squeezing, she took the hand and moved it down between her open legs. As soon as I moved her panties aside and inserted a finger, her kissing became much more demanding.

At that point I said we should move to the bedroom. “Finally!” was the only word she spoke as she was standing up and taking my hand. Once in the bedroom we began kissing again, and our clothes were undone and removed without any interruptions in the kissing. I pulled the covers down, and we both slipped into the bed. More kissing, and this time she didn’t need to direct my hands to where she wanted them. She did, however, stop the kissing in order to push my mouth down to suck on a nipple. Then to the other one for more of the same. It was time to move on to the logical conclusion, and she was more than ready.

She pulled my head back up for more kissing as she wiggled underneath me. Once we were lined up, she wrapped her hand around me and started to guide me in. “It’s been a long time for me, you’ll have to start slow”. It took a bit to get inside because she was not very lubricated at first, and it was a tight fit. But little by little I made my way in, and we began to move against each other. We were no longer kissing, her chin was up, and she began a whimpering sound that slowly built up. Now pumping against each other, I was pushing in and out of her harder, and her whimpering turned into moaning. Her tightness shortened my time thrusting, and as I was emptying into her, she gave out a long “Ahhh” sound.

After a short time, I began to pull out, but she grabbed me from behind and held me inside her until I softened and slipped out. We were on our sides, with our arms around each other, and she thanked me, telling me that it was not easy at her age to find a partner. We chatted a little, but were content to just cuddle with a few kisses. I was not ready for round two by the time she reluctantly said she needed to go home. The reason she gave to her daughter for going out after work was to go to the library, something she had done at lunchtime so she could bring a couple books home. Her daughter was very conservative and would’ve been appalled to learn that her mother was “shacking up with some guy”.

We set up a standing date for every Wednesday night. She brought dinner, and I supplied the wine and the bed. Because she couldn’t stay out too late, dinner time was shortened in order for sex time to be lengthened. Although she was much older, I was the one who was teaching new things. She had never received oral sex, and immediately became a fan. On the giving part of oral sex, her experience was limited to helping her husband get ready occasionally, and it had never been taken to the end. Although she didn’t become a total fan, she finished me off a few times to show her appreciation.

Her sexual experience had been limited to missionary or her on top, although that was rare. I introduced her to doggie style and that became her favorite. I took her bent over the counter once, and another time on the floor in front of the couch. She was reluctant at first to take a shower together, but once we were all lathered up and slippery, the sex that followed turned her into a screamer. This arrangement continued almost every week for a couple years.

Sadly, all good things must come to an end. She retired and moved to Florida to escape the snow. We called each other from time to time, and I visited once, but things kinda faded away. I still think of her from time to time.