Cherry (2010)

Younger than everyone else because he skipped a few grades college freshman Aaron Milton (Kyle Gallner) gets an unexpected education in MILFology when he falls for a 34 year-old back-to-school mom (Laura Allen) in the comedy-drama Cherry (2010). Aaron's a seventeen year old virgin who's majoring in engineering since his family doesn't support his dreams of becoming an artist. While at college, he feels a bit weird about being younger than everyone else, which leads him to fall for Linda, his MILFtastic fellow student who is actually way older than all his classmates. But she's got a cop boyfriend (Esai Morales) and doesn't seem all that interested in being more than friends. Her 14 year-old daughter Beth (Brittany Robertson) sure has the hots for him, though. She tries to seduce mom’s new boy-toy, while somehow Aaron also has a cute girl (Zosia Mamet) lusting after him in the dorm hallways. With all those options at his disposal, the uncertain of himself Aaron has to figure out exactly what he's going to do in a situation most men can only dream of. Date the college girl, stay friends with the mom and wait four years for the teen to become legal? Ignore the college girl and wait for the MILF to ditch the cop, so in her sadness she'll reach for her closest male friend and hop on top? Date the college girl, but, oh heck! It's like a sex filled riddle with no wrong answers! To better assess the pieces of ass he's choosing between, take a peek at Laura Allen jiggling her giant jugs in a tight black bra lying in bed after opting not to have sex with Aaron. Zosia Mamet lies back in her black bra to seduce Aaron, but doesn't quite fill it out with her funbags the way Laura does. And Britt Robertson is in a bra too, but she's too young for Aaron to screw. Ironically, the only nudity comes from a woman Aaron has no chance with. The super nailable Aleah Nalewick is a naked model for an art class Aaron is taking, who we see lie naked in bed with her hand between her legs while posing for a sketch. That'll have you pleasuring your pencil! Three hotties to choose from and a naked chick to spend your time staring at. That's the Cherry on top of this sex sundae!