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Date night

I started doing date night about 10 or so years ago when I was in my 20's. There have been multiple variations since then. But as always you never forget your first time.

I just broke up with my girlfriend but had tickets to various events we planned to go to. Sporting events, concerts, and the theatre. Not wanting to waste the tickets I would go to the event and usually invite a buddy to join.

The only event I could not find someone to go with was the Broadway show at the theatre. I asked a few of my female friends and the ones that wanted to go couldn't due to the date/time of the show. The others wanted the tickets for themselves. I've never been and wanted to go for the experience.

I was just about ready to give up and give the tickets away when I remembered a conversation I had with a neighborhood gentleman I always ran into when walking our dogs. The story was of the first time he met his wife and how she was an actress who did the smaller theatre shows.

I walked my dogs a lot that week in hopes of bumping into him. One walk I saw him and told him I needed a date for the show and if it would be ok to take his wife. At first it looked like he was going to punch me then he said it wasn't up to him if I could take her out it was up to her, but he was fine with it as long as I had her back by breakfast the next morning.

We walked back to his house and I asked his wife if she would accompany me to the show that weekend. Her husband said no she can't accompany you, you asked me if she could be your date. So I rephrased and asked if she would be my date for the night.

She smiled and graciously accepted but had a few conditions. I had to bring her flowers, take her to dinner, and compliment her on her looks. Her husband chimed in and again told me to have her back by breakfast the next day. I took this as a joke since it was a later show and we probably wouldn't get home until after midnight.

The night arrived and I picked up Claire. I almost didn't recognize her. She did not look 60 at all she looked a lot younger. She got her hair done, a knockout red dress that showed off she was hiding a body under her normal sweats and baggy shirts.

I gave her a bouquet of flowers and complimented her on how stunning she looked. I opened the car door for her and we left for dinner. Dinner was good we went to a restaurant near the theatre and had a great meal and conversation.

On our way to the theatre she told me a lot of people were staring and felt selfconscious and thought it was because they didn't approve of her wearing that dress and being so old. I told her they that it was most likely how did this average looking chubby guy get a knockout date like her. We left and went to the show.

We watched the show and had a great time. As we were walking back to the car she said she was cold and I gave her my sports coat. We were just about to head back when she said lets go get a drink and she wanted to dance. I told her to call her husband so he's not worried. She texted him and all he said was to have her back by breakfast, and he wasn't going to eat breakfast until 10am tomorrow.

We went to a salsa club she had a few drinks and danced a couple dances then she decided we should head home. I pulled up in front of her house and she asked what I was doing she didn't need to be home until 10am. I told her I didn't want to do anything either one of use would regret later. Just as I did that she plays a video for me her husband sent saying that I was hers til 10am and she could do anything she wanted.

Our first stop was a make out point that she used to frequent when her and her husband were kids. We made out in the car and a female officer broke up the fun but had a laugh when she say we weren't some high school kids.

We went back to my place and had sex.

The next day during my walk her husband thanks me for showing her a great time and being respectful to her wishes.

Over the next 5 years we had date night once a month. Each time the experiences got wilder and wilder.

One night we had sex before we went out, she lifted up her dress put her panties to the side and told me to cum as quick as possible. That night she danced to her hearts content with her pussy full of vim.

The last date night we ever had was when she introduced me to my future wife, the female cop that caught us making out. We went out had a great time and when we got to my place she said she had a surprise. It was a 3some. It was a great bookend and amazing time had by all.