Its not a generational thing, its an ugly thing. I don't know anyone my age(20's) actually fuckable who has to brag. Ive hooked up a lot, but I don't tell people that, and Ive never had any guy I fucked brag about it or their conquests either. Ive dated ugly guys (trying to not be superficial lol) and they are the insecure braggers. Most my friends are pretty open sexually, and we don't act trashy about it. We also do really well, so theres no reason to overcompensate. Its always either in my group, or out socially, the ugly people who boast about their sex life. Its almost like "Despite the fact that Im physically hideous, and you probably believe Im completely unfuckable youre dead wrong. Ive had over 2 consensual sexual acts this year alone, my friend!!!!!"