Playing on both sides
Having anal sex along with regular f*cking, similar to DP
"Jim, I hate playing on both sides, it really hurts."
Playing for Both Sides
To be bisexual. You're sexually attracted to both males and females. You don't care which gender they are, because love is love after all.
Same as 'batting for both teams'
Same as 'batting for both teams'
Person A: I play for the guys, what about you?
Person B: I am playing for both sides
Person B: I am playing for both sides
play both sides of the ball
to swing both ways
dude i fucked her then i fucked him, i play both sides of the ball