Cassandra and Jay

You and Cassie make your way to the third floor of the building where your apartment is located, both excited and in disbelief that what’s about to follow is going to happen. As you reach the third floor, a realization hits you so hard that you can’t believe that both of you didn’t even consider it until now.

“Cassie, how do we…” you try to ask her how you’ll deal with the whole situation of Stella also being in the apartment, but you stop as you see Cassie placing a finger above her lips, signaling you to shush.

“Your keys, Mr. Craig” she says, and you hand over the keys to your apartment to her.

“Okay, Jay, wait here. I’ll just go see if my roommate is already asleep.” She tells you.

You’re surprised at how committed she is to this roleplaying, but you decide to follow her lead and nod that you’ll do as she says. Cassie opens the door and you can see the lights of the apartment are turned off. She closes the door behind her, and you can hear her call out for Stella from the inside.

It doesn’t seem like Stella’s home from the looks of it, so you decide to text her.

‘Hey baby, Cassie and I just got back to the apartment. Don’t stay out too late. Call me if I need to pick you up. Love you’

After sending the text, you look at the door of Tanya’s apartment across the hall from yours, and flashbacks from last night appear in your mind. You can’t believe how quickly things are changing for you in just the two days since Stella and Cassie came back from college; but maybe more importantly, since you acquired the Affection Multiplier app.

As the app crossed your mind, you wanted to check it just to see if the date improved anything with Cassie, but she opens the door to the apartment once more and you decide to pocket your phone.

“Lucky for us, my roommate’s out. Come in.” She tells you. You enter your apartment and don’t really go that far from the doorway, not wanting to act like you actually own the place and stick with Cassie’s roleplaying.

“Your apartment’s nice” you say awkwardly, not really knowing what to say.

“My bedroom’s even nicer.” She replies seductively, as she hugs you from behind and slowly raises both her hands to your chest. You turn around and give Cassie a kiss. You continue your kiss from where you left off downstairs, and wrestle Cassie’s tongue with yours.

She doesn’t hold back her moans as she knows that it’s only the two of you in the apartment right now. She places her hands on the back of your head and lifts her leg to wrap it around one of your thighs, not allowing you to break away from her as she hungrily makes out with you. You place a hand on one of her asscheeks and squeeze it gently. To your surprise, she does the same and brings a hand down to squeeze one of your asscheeks too.

“Your lips feel incredible, Jay” she compliments you, taking a breather from the make out session. You kiss her again so she can feel your lips against hers once more. She moans into your lips, and proceeds to take one of your hands and place it over one of her breasts.

“Yes! Squeeze my tits, Jay!” she shouts in pleasure as you knead her right breast with your left hand, and you feel she might not be wearing a bra underneath her dress. Her breathing is getting heavier as the make out session keeps going, until she literally pushes you away from her.

“Not here. My roommate can come back any minute.” Cassie tells you and proceeds to open the door to your bedroom. It’s here that you come to another sudden realization. You’re about to have sex in your ex-marital bed. You haven’t even slept in that bed in months, opting for the couch every night.

Now, you’re about to have sex with your daughter’s best friend on that bed. Not just your daughter’s best friend, a girl you used to babysit. The realization makes you freeze on the spot where Cassie left you, unsure how to proceed, as thoughts of guilt and doubt start ringing in your head.

You try to shake it off, reminding yourself of the wonderful date you just had with Cassie. You remind yourself of the kiss you had downstairs, and how excited you were to finally break free from any doubt that this relationship with her could work. Then you look at the open door in front of you and you just can’t shake off the fact that there’s just too many memories inside that doorway that you’d rather forget right now.

“Jay? This is my apartment. My room. My bed. You haven’t been here before. This is the first time you've been to this apartment.” She tells you, reminding you of her roleplay that you’re not in ‘your’ apartment, but hers. You wonder if she knew this would happen, and that’s why she started this roleplay to help you get over your anxieties and irrational thoughts.

“Cassie—” you try to say, but she cuts you off. “It’s Cassandra. Cassie’s for little girls who still need babysitting,” she says with an air of faux sophistication. You rub the back of your neck, embarrassed that you’re being a baby about this. Cassie breaks character for a moment and gets closer to you, resting her head on your chest as she gives you a hug.

“Mr. Craig, I know you have a hard time sleeping in your room. When I was cleaning the apartment yesterday, I noticed it almost looked untouched. I don’t want to **** you to do something you’re not comfortable with tonight, but it’s not exactly a smart idea to do it anywhere else in the apartment.” she says, chuckling at the idea. You laugh a little too, as you imagine Stella walking in on the both of you.

“I don’t want to **** you, but I also want us to try. That’s why I thought we could forget who we are for a while. We’re just Jay and Cassandra now. Two adult friends who only just met tonight and had a wonderful date together.” she adds.

“No history. No baggage. Just…”