:GxG Pairing Ahead:
You had worked for Jenna since she had turned 18 and she needed someone to manage her schedule better then her previous assistant could. You had no issues and enjoyed working alongside her, So much so that the two of you had started spending time together outside of actual work.
You two started having sleepovers when she had to stay in hotels because she didn't like being alone. They started out friendly and fun where you talked a lot, shared memories and got to know one another better ECT.
It had slowly blossomed into more where you would play with her hair while she fell asleep with her head in your lap. You would paint each other's nails to match and watch romantic and horror movies cuddling on the couch or the bed under fuzzy blankets.
You two started sharing a bed just a month ago no longer booking two hotel rooms and nobody ever really assumed anything because you worked for her and they figured she wanted you closer so you could work easier.
But only you and her knew the truth because you two had bloomed into a relationship neither had confirmed it yet, but it was your intention to do so tonight. You had set up the hotel room with dinner and flowers a blanket and pillows on the floor for a little indoor picnic with her favorite horror movie waiting on the TV to watch while you ate.
You also had a dessert that had "Be My Girlfriend?" Written across it and you really hoped that she would agree to it.
*Once She Arrives*
You greet her with a sweet kiss on the lips and smile.
"Surprise" You say softly.
She giggles and looks at the set up.
"This is really sweet Y/N, You always make the best dated" She says in a cheery tone.
You blush and lead her over
"I picked out our matching PJs figured we could wear them during dinner and the movie" You suggest
"I love that idea!" She says and you both change into the PJs before you rejoin on the blanket with the pillows and you play the movie while you two enjoy the dinner room service had brought.
It was actually pretty delicious, but you were excited for dessert.
Once you finished dinner you brought out the dessert and set it in front of her.
"Another little surprise" You say
She smiled wide and takes off the cover on the cupcakes and reads what it says her smile growing more if possible.
"Definitely!" She agrees and pounced on you in a tight hug.
You giggle and lock your arms around her hugging back quick.
Her lips find yours in a soft sweet kiss that you eagerly return and slowly deepen rubbing her back while you two share in the passion filled kiss as the horror movie plays in the background making the perfect atmosphere in your opinions.
She breaks the kiss and giggles softly.
"Let's enjoy dessert" She suggests.
"Always beautiful" You reply and pass her a cupcake cheersing them together both giggling again.
