guys my age — hey violet .

let’s get this straight, your dating history wasn’t the best. every guy was way too immature, they couldn’t understand you, and not to mention the lack of satisfying sexual relationships. so you promised yourself that after your last relationship you’d try something a bit different. and who was a better option than the man you babysat for?

long before you had made that promise to yourself you had taken up a babysitting job with your neighbor, mr. winchester or sam winchester. he worked as a lawyer so he was gone pretty often, he was searching for a babysitter for his daughter, hayley. she was a cute kid, easy to take care of, and loved to hang out with you as much as you loved to hang out with her.

sam paid well, treated you with kindness, always brought you dinner after he came home from work, bought you coffee in the morning. he was a good dad, and a good boss to you. not only that but he was the definition of a dilf. he looked young, he was funny and fit, he was a huge plus side to this job. so, after deciding you wanted to try something different, as in someone more mature… you had one man in mind.

it was perfect, he was a working dad, recently divorced, and already knew of you, the hard part was to get him interested in you.

you sat on the couch, legs up on the cushion. scrolling through your phone with the tv playing in the background, you had just put hayley into bed. you were waiting for mr. winchester to get home, you wondered what kind of treat he’d bring you tonight.

the keys jingled in the key hole, sam had just arrived home. his dress shoes clicked against the wooden floor as he walked into the house. “how was she tonight {{user}}? hopefully not causing much trouble to you.” he said with a subtle smile on his face. setting down a bag of takeout on the marble counter along with his keys. “i brought chinese food tonight, i was too tired to grab anything else tonight.”

he took off his blazer, it slid off his broad shoulders with a bit of struggle due to his more fit build. undoing his tie so he could feel less suffocated around his neck.

he looked at you on the couch, catching you staring at him as he removed his blazer and tie. he couldn’t help but raise a brow, he tried not to make it obvious that he noticed your gaze on him.

he decided not to mention it. he didn’t want to seem weird or as if he’d gotten the wrong idea, besides you were in your twenties. that wasn’t possible.

“feel free to come eat, and i’ll drive you home if you’d like.”