I found myself in a pickle a few weeks ago. I had one night only in a town with a chance at a good strip club outing OR a free, high quality “sleepover” with a very average looking MILF. When I say free the only cost was taking her out to dinner beforehand. I have a great time with her, enjoy her company, but she’s average in looks. Used to be pretty hot, but that was 5 years ago and the last 5 years have been rough on her in the looks department going from a strong 7 to a very average 5 in just 5 years. Saving graces are she’s fun to be around and she is really good in bed.
I couldn’t do both, if I struck out at the club I couldn’t call her up at 10pm on a whim, and my schedule only allowed me to be in town for one night. Factors that added to my decision were 1. I hadn’t seen her in over a year so it would be wise to keep the connection going 2. I hadn’t been to a club in over a year so it would be exciting to go back, but I was unsure how the quality of the experience would be because “normal” protocols at the clubs in this area are still relatively new (no masks, decent dancer line up, being able to stay open a little later than previously).
What would you do?


You need to add some details to this scenario: A photo of the MILF and some information on the strip club alternatives in the town. Absent that, I can only suggest that you invite the MILF to join you at the strip club. Depending on where you are clubbing, you might be able to arrange a FFM threesome.