We have known Rob and Flora for many years. They were good friends. I golf often with Rob. I had always found Flora to be very attractive. She is not a classic beauty. She wears no makeup. But I've always thought she was hot. When we were younger Lindsey had a real crush on Rob. Rob and Lindsey share the same birthday. Rob and Flora were married a couple of years after us. We've been married for 42 years and are in our mid-60s. To me, Lindsey is still a knockout and has kept her body in good shape.
Rob is one of those emailers who sends out multiple emails a day. Generally, Rob's emails have to do with women and breasts. One day when I was playing golf with Rob I said, "Why don't the two of you come over for drinks and a grill-out and some skinny dipping?" We have a pool in our backyard that is rather secluded. Although we have neighbors who live not far away, most of the neighbors are shielded from our pool and the others do not have a direct line of sight, unless they are driving by. But we have a fence around the pool area that shields most of the pool activity.
Rob's response to my inquiry was that Flora would never get naked in front of others. When we go on vacation Lindsey often goes topless at the resort. She's never had a problem going naked, except for those times when she has put on a little too much weight. But she had been on a diet for a while and therefore felt good about her body. I had no concern as to whether she would be willing to skinny dip.
So I told Rob that if Flora didn't want to skinny dip, that was fine, the rest of us would do so and she could bring a bathing suit. He said he didn't think she would ever be willing to strip down naked. But I always had hopes. As I said before I think Flora is hot; she has nice full breasts and I have often fantasized about playing with them and kissing her nipples. So it was worth a try.
Thursday evening came and Rob and Flora showed up for drinks. I gave Rob a beer and Flora a glass of wine. Lindsey brought out guacamole, hamous, chips, Pita bread and cheese and crackers.
We have lots of things in common, so conversation was not a problem and we talked for a good while. I figured it was time to push the button and see what would happen. So I said to Rob, "Rob, I'll give you five dollars if you take all your clothes off."
Rob said, "You're on, but only if you do it first."
So I stood up, removed my shoes, pulled off my shirt, unbuckled my belt, unzipped my pants and dropped my shorts. I then removed my boxers, and there I was, stark naked in front of my friends, Rob and Flora and my wife Lindsey.
I took five dollars out of the pocket of my shorts, which were now on the floor, and handed it to Rob. Rob smiled, took the five dollars and removed his clothes as well.