Yesterday morning, I received the following email from Mommy.

We are going out tonight,
We will arrive together, but enter separately. You will sit on the opposite side of the bar. You will order a drink for me and have the bartender bring it to me. I will sit and enjoy my surroundings. I may find a man to flirt with. If so you will sit and watch, tormented, knowing that I love you, but enjoy the company of real men. If I can’t find someone I want to flirt with, I will text you and tell you to join me. We can make it look as though we are strangers, who meet at the bar…Then we leave together.
Do you understand?

I responded as usual: “Yes ma’am.” She texted me throughout the day saying how excited she was for the evening, which was reassuring to me, as I’m not sure she is entirely comfortable with the idea of cuckolding. Yet.

When I came home that night and showered, Mommy was dressing in new clothes and heels she bought earlier in the day for our night out. She had a navy blue blouse that along with her new bra made her breasts look very prominent. She had a tight skirt cut above the knee and very tall heels. Normally, Mommy is several inches shorter than me, but with these heals, we were just about the same height. She was well made up and her long, curly red hair looked stunning.

On our way to the bar, we stopped at a local winery that was on the way. Mommy said she wanted a drink before going to the bar to calm her nerves. We did a tasting and then ordered two glasses of wine. Although it had been raining much of the day, it was sunny now, and we sipped our wine while listening to a small band play, and looking out over the valley below.

Then we went to one of my favorite bars that is on the ground floor of a mansion converted into an upscale hotel. The bar has a great atmosphere, with antique furniture, and old timey cocktails. I entered first, and Mommy followed maybe five minutes later. I stood at the end of the bar and she sat near the opposite end.

I ordered a fancy cocktail and told the woman bar-tending to make a second for “the woman with the red hair.” This is the first time in my life I have ever ordered a drink for another woman and had it sent to her, as I would never go to a bar by myself, and even if I did, I would never have the courage to send a drink to an attractive woman I didn’t know. As the bartender turned to make the drink, I thought I saw the barest whisper of a smirk on her face.

The planned flirting didn’t happen–the crowd that night was a lot of couples, some significantly younger than us, and the others significantly older than us. So after a bit, when it was clear that there would be no flirting, Mommy bit her lower lip, which was our prearranged signal for me to join her. I approached her and asked if the seat next to her was taken, and then we enjoyed our cocktails together and ordered a few more drinks. Sometimes pretending we had just met, for the benefit of the bartenders, and sometimes just acting as we normally would.

It hadn’t occurred to me before that point, but as I wondered what people around us might be noticing and thinking, I realized that the outward picture might be of a man confident enough to order a drink for a woman, approach her, sit next to her and make her laugh, and then leave with her, like a real man. That gave me a feeling that I am not familiar with.

It was a fun adventure even if the flirting didn’t happen. In fact, it may have worked out better that way, as this is new to both of us, and just getting out and getting our feet wet doing this sort of thing may have been plenty for one evening. Next time, we won’t feel as awkward.

There was a gourmet food truck parked behind the building, so we went out and ordered some food and ate outdoors, enjoying the cool night. We then went home and Mommy unlocked my cage and let me cum for the first time in two weeks. She left me out so that in the morning I could thoroughly clean and shave, and then I was locked up once again.

This morning, Mommy wasn’t feeling all that well, so I did what I could to comfort her and do some chores around the house. Then I had an idea: this was the first rain-free day in quite some time, and I knew this would be her first opportunity to ride her new motorcycle. I knew of a spa, about a 50-minute drive away, in a hillside resort, and I told her she should go there, and that I would buy her a spa treatment. The ride would be one that I knew she would like, through back country roads and small towns, and the length of the ride would be perfect. Mommy was excited looking at all the treatments available, and she finally decided on an aromatherapy massage and time in a “salt cave” after. I called and made the appointment and paid.

It’s so nice to see Mommy happy, and it makes me feel good to know that I can do things that make her happy.

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