My wife was 34. I was 39. Shes 5'3 with a total milf bod. It was in the middle of Covid. We wanted to live our life and decided to go Florida because everything was open. We ended up a nice resort with a bar and music venue on the beach. On the 2nd night we went to the bar and we drinking and listening to some live music. We noticed this 30 to 40 something black guy in a cowboy hat dancing and having a good time. He was the guy having most fun. My wife likes those guys. He was fit, wearing tight blue jeans and cowboy boots. After a few drinks I told her to go dance with him.

My wife knows about my wife sharing/cuckold obsession but to this point hadnt done anything to entertain the idea. I could tell she was attracted to him cause she was watching him like a hawk and making comments to me about him. When I told her to go dance with him she didn't need much of a push.

As they danced, i watched. Thats when this mature woman approached me and asked if i was a cuck. I couldnt believe it. She had seen the situation. She knew what was going on. She told me her ex-husband was a cuck. Then told me to have a nice night as she smiled and walked away.

My wife and this black cowboy danced and laughed and were having fun. They hit it off and after awhile she introduced him to me. She then whispered in my ear that she told him I was into watching her get fucked. I was surprised cause to this point I wasn't sure if it would ever happen. He was cool with it though. We went to the bar, and when it was my turn to order I told the bar tender our drink order and pointed to where they were standing at the end of the bar. It was then I saw it. They were making out. The bartender gave me this funny look. He knew. When the drinks came they took there drink and said they were going for a walk on the beach.

They disappeared for 15 min or so. When they came back she said we were all going back to the room. At the elevator to the room, the guy said he was going to run to his truck to grab some condoms. While we were waiting for him, my wife was visibly intoxicated. She said she didn't feel good. I let him down easy and explained she wasn't feeling good when he returned. He was bummed. We went back to the room. She got sick and passed out. I jerked off thinking about what could of been.

The next day she told me when they went to the beach they continued making out and she put her hand in his pants and felt his cock. She said it was big. She said "way bigger than you".

I was so bummed that my cuckold dream didn't become a reality. I've jerked off to this memory many times now.