At the bottom of page 27 I posted a story about a friend stopping by our pool one afternoon with one of his friends. This is how we started our relationship with him.
I don't think I have ever told this story about how Mike became our first FWB. He was the first man we had ever thought about having sex with that we had known as a friend for several years. He had even worked for me a couple of summers while in college. We had gone out on a couple of dinner dates and to the movies with him and his date. He did not have a long term relationship with any of these girls. One evening while I was talking to Elaine about trying to find someone to fuck she said "What about Mike?" I was surprised because she had always wanted to do people she did not know or were not considered good friends. I said "Are you sure?" She said he was everything she liked in a man, tall, good looking, had recently broke up with his GF and we were already good friends. I agreed but just wanted to make sure she was okay with it. He was 25 and we were about 40. We had never tried to seduce someone we knew this well and were a bit uncertain of what approach to use. Many men actually get nervous and hesitant about 3 way sex so we finally decided to just surprise him and hope for the best.
We invited him to our house for dinner and drinks. I cooked steaks outside on the grill and we enjoyed the food and wine. After dinner and some small talk I said we had a surprise present for him. I told Elaine to go get it for him. We had obviously discussed this and set it up in advance. She had her lingerie already set out along with her lipstick for a quick freshen up. While she was upstairs changing he looked at me kind of funny and said "What's the deal?" I said we had done this before and always liked it and thought we should share our fun with him. He just looked at me like what the hell are you talking about. I smiled and said you will know in a minute or two. We were in our living room and I had sat in the chair next to the couch making sure he sat there. I set our drinks on the coffee table. When I heard Elaine walking down the stairs I told him to close his eyes for a few seconds. When he opened them Elaine was standing in front of him dressed in this outfit. He was speechless. These pics are not from that evening but are the outfit she was wearing