Wait for him here.

You wait patiently as he rifles around the in the coat room for for a minute, then hear an 'aha!', after which he rejoins you. He leads you up the back staircase and you climb several flights, coming out on a rooftop parking deck. It's not exactly a rooftop bar or romantic patio, but you're immediately struck by what a perfect evening it is, with crystal skies and twinkling stars. You can see out across the city, and the glow of its myriad lights rivals that of the firmament. Isaac guides you to a corner and sits on the edge of a large planter tucked behind a nice BMW. There's still a good view, but you notice it's a bit more private.

Isaac pulls out a little bag with a few joints in it and lights one. He offers it to you and you smile a little shyly and blush, 'I haven't since college', but you take it anyway and inhale. The harsh smoke instantly makes you cough. Isaac smiles, 'here, let me help.' He takes the joint from you and inhales deeply, then holds his hand up to his mouth to shotgun it to you. You put your mouth on his hand and inhale the pungent smoke. It's more mellow this way, and you both enjoy the intimacy of your mouth on his hand. The two of you start talking again and enjoying the evening, starting to feel a different kind of buzz on top of your tipsiness and horniness. You're feeling pretty uninhibited, and you're starting to feel pretty aroused. You start playing with the hem of your skirt as you chat, lifting it up your legs just a little, and then you catch Isaac staring down at the lacy tops of your stockings that you realize are showing. Your eyes meet and you both start laughing. He takes another hit from the joint and brings his hand up to pass it to you, but you pull it down, then lean forward and kiss him deeply, the smoke filling you mouth as your lips meet and tongues intertwine.

You both break the kiss and you giggle a little. You haven't had such a fun and relaxing night in ages, in fact you can't remember feeling so carefree since college. It's a wonderful feeling to recapture for a night. You lean back in and kiss Isaac again, then feel his large, strong hand on your knee, slowly sliding up and under your dress. His hand caresses you and sends a shiver through your body. You let out a breathy little moan, and hump your hips forward against his hand as your lips part and tongues meet. You're sure Isaac can feel how excited you're getting from the dampness in your thong. He's clearly ready to move things to the next level when he kneels in front of you and starts sliding your underwear down you legs.

Making out and smoking on the roof is one thing, but is this where you want the evening to go next?