It all started in early high school with my best friend who was more sexually experienced than me. He ended up challenging me to a size contest and the winner got to slap the loser in the face with his cock. I was still confident at that point and brought out my 5 incher first and he goes “oh man, now I feel bad.” He pulled out his and it was legitimately 7.5 inches. He said “a bet is a bet” so I got on my knees and he slapped my cheek with his heavy cock.

Later that night, he was messaging my gf at the time on AIM and she didn’t know I was over at his house. He asked her if she’d ever considered taking two guys at once and she said YES! My mind immediately went to how she could possibly handle his cock. I knew she couldn’t but the thought consumed me.

Fast forward to today. I’m still best friends with him. His wife has expressed interest in watching him with another girl. I’d love to see him with a future girlfriend of mine. Is this an absolutely terrible idea? I know he could give her pleasure that I couldn’t. What do you guys think? Should I bring it up if the opportunity presents itself?