First and foremost congrats on the cougar/ milf. I have fucked a cougar before (38 year old woman) and a mother (23 years old), and they were both fun. Before I give you my advice I have to tell (or claim) my story.
Few weeks ago my family went to to miami for thanksgiving, I met a 38 year old down there, hung out with her on the beach the whole day on thanksgiving, fucked her back at her place, and finally turned my phone back on at 5 to see these text messages from various family members
"you have been gone since 8 am, where the hell are you?"
"don't show up to thanksgiving drunk"
"We are going to be eating at (insert resturant), you better be there"
"at least let us know you are alive"
5pm "you missed thanksgiving dinner"
Well, I call them back, tell them I am alive and did not think they would have dinner that obscenely early. Tammy and I go outside to find her car had been towed while we were banging. We try to get her car back, we couldnt, all of this shit is going wrong, and then I have one of my greatest strokes of brilliance/stupidity ever. I know that if I go see my parents alone they will be absolutely livid with me, so I tell them I am with this girl that I met the night before (I told them about her wednesday, but I just said she was older, not how much), and that she was alone on thanksgiving in her brand new empty condo and I was keeping her company. So here comes the dumbest/smartest thing I could have done. They are having a second late dinner at like 9 o clock and I ask my dad if I can bring her along (still havent seen my family all day). I introduce her to the family and things go surprisingly smooth at the restaurant until we get back to the condo and her and my mom get in a small argument.
Pic of said cougar
/claim
Anyways, I would say fuck it, bring her to dinner. The worst that happens is that there is an awkward encounter that will eventually turn into a really funny story. I can promise you that my grandpa (who was at the dinner) will not stop singing "Mrs. Robinson" to me anytime soon.