Dude -
Speaking here as "an old fat guy", you don't have to do anything to justify what you drive. Quit worrying that you'll be a cliché and do something for yourself that makes YOU happy. When I'm too old and fat to climb in and out of my Boxsters, I'll get a Cayenne GTS.
No need to keep it secret either. The 20 year old girlfriend? That's what you keep secret. The Boxster you take out and drive. The 20 year old girlfriend you can hide with in the garage.
And just three cars? You're a rookie...
Go find yourself a nice 986 and enjoy your life!
2002 Porsche Boxter S
2001 Porsche Boxster S
1999 Porsche Boxster
1999 Porsche Boxster
1999 Porsche Boxster
1999 Porsche Boxster
2000 Porsche Boxster
1999 Porsche 996 C4
1972 Porsche 914
1984 Porsche 928S
1984 Porsche 928S
1985 BMW 635 Csi
Hybrid Mode
