Helping a friend [MMF]

I have a friend from school, lets call him Freddie, now Freddie is a nice guy, around 25, but he didn’t really talk to much girls and It kinda showed. He was a bit on the nerdy side but he was pretty cool. I had been hanging around him a lot recently since we had a class together and we were at a kickback at my house one day with me (21), my girlfriend (21), Freddie (23), and a few other friends when the topic of sex came up while everyone was talking, everyone was sharing their silly stories about almost getting caught fucking or some shit like that when some asked freddie if he had any stories. That’s when Freddie laughed and said he doesn’t have any stories but he’ll tell us when he finally does. By this point it’s pretty obvious to me that Freddie has never been laid, I never see him worth any girls or anything and he’s just that type of guy, this is when all types of ideas get into my head.