I Would Give Lisa Ann The Best Night Of Her Life

Out And About released a special Valentine's Day episode today with Lisa Ann where me, Jetski, and Meek Phil all pitched ourselves for a chance to win a date with her. Jetski and Meek Phil laid out the very nice evenings they'd have with her. Jetski wanted to take her to a fancy dinner. Meek Phil wanted to talk fantasy football with her. But not me. I went with the negging approach. The best way to feel better about yourself is to bring down those around you. Lower her self esteem so that I can feel better about myself. It's brilliant. 

With that in mind, here is my plan for an evening with Lisa Ann.

-I tell her we'll meet at a cocktail bar at 8 PM. I show up fashionably late between 8:15-8:30 so she has time to sit there all nervous  I'll stand her up. She immediately realizes I have better things to do with my life than be on a date with her. It will make her want me more. 

-I order myself 2 or 3 pink cocktails. Ideally Malibu Bay Breezes or whatever the closest equivalent they have is. I ask what drink she'll be ordering and regardless of her response, I let out a scoff and whisper "Interesting."

-The night goes well. I'm providing her incredible entertainment. Jokes, stories, relatable observations, you name it. She's falling in love more and more with every word I say. 

-Eventually she tries to break the touch barrier by putting her hand on my thigh underneath the table. I instantly shoo it away. "Not yet, sweetheart. It's cold and flu season." 

-The night continues to go well and eventually the check arrives. I put my card down immediately. I'm not paying for all of it though. I have an American Express Delta Reserve card and I need to get those SkyMiles. I whip out my calculator app to figure out how much she owes me for her share and then pull up my Venmo QR code. 

-As we're leaving the bar, she wants to get a drink somewhere else. I say, "Sorry honey. It's 10 PM in New York City. Everything is closed. I guess we have to go back to my place."

-We get back to my apartment and can't decide what to watch. So there's only one option. Classic Tommy videos. We're watching smash hit after smash hit and she's in tears laughing. She can't take it anymore and immediately starts kissing me. We then have missionary sex for about 4-6 minutes. I cum. She doesn't. (Women aren't able to cum, biologically speaking). 

And that's it. The best fucking night of Lisa Ann's life. I'm in bed by 11 PM and can still get a solid 8 hours of sleep. Watch the full Out And About to see who won.