It was a summer weekend, I was between serious ladies in my life and I was bored. I decided to try a new venue and went onto one of those phone services where people can hook up. I left a simple message, would someone like to dress up, go for dinner and dancing and without any obligations, nil, nada? A few replied within the next hour and one sounded better so I called her. Turns out her daughter was having a birthday party that night, girls only and mom needed a night out. Now this was a rather sexual service so she was obviously looking for something.

Around 7 pm I drove up to her building, a highrise, working class area. She was standing outside and wearing the dress she had told me about. I got out and kissed her on the cheek and held her door open. She was hesitant not because of me but because I was driving a brand new Cadillac at that time and she got in and said she had never been a new Cadillac.

She was a somewhat plain woman. She had worked hard all of her life and that was reflected in her mannerisms and character. Not an edge but more of a submission to life. She was dressed in her best which was lacking in many ways. Yes, I live a somewhat affluent lifestyle, although I am not rich and I was dressed in a blazer, tie, summer styling and I felt good that night. I was maybe 40 at the time.

She was used to less than fancy restaurants and then and there I made a decision, I was going to make her Queen for a Day (if you remember that show, which my mom watched). I drove to a better restaurant than I was going to and she said that she had rarely been to such a nice place. She lacked great conversation skills so dinner was not exciting. She was one of those women who was not attractive but not unattractive. You would pass her on the street and not notice her but she had a decent figure, a gentle face and sad eyes. I guess the eyes got to me.

After dinner I took her to a club and even at 40 we were the oldest people there and the best dressed and I just didn’t care. She lacked dance skills but she said she liked to move to the music so I just let her do her thing on the dancefloor. One thing, I can dance. When I was 19, I was actually a go-go boy in a disco. Love to dance and when friends of mine go through a divorce I encourage them to go for dance lessons. Guys who dance well never lack for a good time (I am now into salsa, a new passion, but I digress).

I took her to a nice little place for a glass of wine and then she used my cellphone to phone her friends who were expecting her for the night due to the daughter’s party. Well it was late, she woke them and they were upset and told her not to come over. She had promised her daughter not to come home that night. What could she do?

I smiled and told her not to worry. She had a small overnight bag that she had brought so she was fine in that regard. I took her to an area not far from where she lived and pulled into a motel. She told me that she could not afford it and I again just smiled and said it was my treat. She cautioned me that she was not the type to sleep with a man the first time they met and I said I had no intention of staying, just would relax until she got settled.

By now it was around 1:30 am. We got into the room and I told her that I would leave right after tucking her in. I told her to take a shower, then get into the bed. She did just that. She had forgot her nightgown, made me promise not to look as she got under the covers in the nude.

I lay, fully dressed on top of the covers and talked to her. She was not a stimulating conversationalist.

I recapped our evening and asked her if she had a good time. I told her that I had one more surprise for her and not to worry, except my tie and blazer, nothing else was coming off.

I told her to trust me but to shut her eyes. I got up, shut the lights and then pulled back the covers. She was naked and with a rather decent body. Not fat, attractive. I started to suck on her breasts and nipples and she sighed. I told her I was not going to kiss her.

Slowly I moved down, kissing her stomach, then sliding down and kissing her thighs until I slid the tip of my tongue into her pussy. For the next 20 minutes I enjoyed the pleasure of her pussy. She hardly moved but she would thrust her hips up when excited.

When she eventually had what I thought was a small orgasm I got up, never said a word and just let myself out.

When she was in the shower I had written her a note, left her $20 and told her to take a cab home in the morning not a bus.

Never did anything like that again, taking a working class lady out for a good time to places she would never or could never go to.

Have thought about doing something like this again but I got lucky. The lady was not unattractive nor dangerous.

My “Queen for a Day” evening.