When Don’s gorgeous new friend Vanessa muses about being swept off her feet in some grand romantic gesture, he sees an opportunity to escape the friend zone once and for all. Valentine’s Day is coming up, the perfect time to woo this stunning blonde college girl. But it doesn’t all go exactly to plan. Vanessa might not have room in her life for a partner, but she does have space for a “little helper” – someone to clean her house, rub her feet and… maybe more.

Donnie made his move on his gorgeous college friend Vanessa on Valentine’s Day, finding that she was more than willing to use him for her pleasure even if she wasn't ready to be his girlfriend. He hopes that going to a 4th of July party together will be a chance for them to come out as a couple, helping him get upgraded from “little helper” to boyfriend. But when Vanessa starts flirting with the hunky athletics captain, Donnie soon realizes he will be facing an emotional and sexual maelstrom. Tonight he is going to experience the peak moment of his sexual life, and the rock bottom.

It’s music festival season, which means desperate Donnie and his free-spirited obsession Vanessa will be dancing and camping together all weekend long. He wants it to move them from FWBs to a real relationship but, as usual, he’ll be dancing to her beat.

Vanessa is treating Donnie more and more like a real boyfriend, aside from all the kinky games and sleeping around. She even invites him to spend the holidays at her family home. A normal relationship seems almost within reach, until he gets on his dominant goddess’s bad side. He soon finds himself on the receiving end of a Spanksgiving punishment, trussed up and more stuffed than the turkey.

Desperate Donnie is delighted when bad weather means he gets to spend Christmas all alone with his dominant, promiscuous girlfriend Vanessa. An exchange of kinky presents guarantees a day full of sexy shenanigans, and she even surprises him with the greatest gift of all— an offer to move in with her! There’s a catch, though. Vanessa isn’t ready for monogamy and wants Donnie to prove to her that he isn’t the jealous type. He soon finds himself chastized and locked up, watching as another man takes his gorgeous girlfriend. Can he handle the conflicted emotions? Can he reclaim her as his own?

Donnie soon finds out that there’s more to Edinburgh than just the tourist sights. Vanessa’s friends are professional dommes, and are preparing to throw a NYE party like no other. Donnie, like all the other men in attendance, is going to have to make himself useful to the sexy Scottish women at the party.

Halloween is an excuse for cross-dressing, debauched parties, and slutty costumes. Even better, Donnie feels like he has finally graduated from the friend-with-benefits to proper boyfriend, now that Vanessa is taking him to a Halloween party as the other half of her costume. She’s even promised to stay away from other men, for tonight.

When Donnie bets against his sadistic domme and her pissed-off friend, he learns that sometimes there’s more to play for than pride! Vanessa’s old friend Rachel is joining the kinky couple for the big game. She needs cheering up after a bad breakup, so Vanessa suggests a sexy bet— if Donnie’s team wins he gets a sexy sapphic show, but if they win he will serve them both for the rest of the day. Donnie soon learns that this sexy nerd’s breakup has left her with a lot of rage to work out on him.