29. Jess
Kennedi:
All right, everyone, Paul and I are going to start at Retrograde at 9:00 and then head to Cooper Lounge after that. Text me when you’re here and we’ll come find you since it’ll be busy.
Ben:
Matt and I are stopping by another party on our way down so we’ll catch you at Cooper Lounge.
Sammie:
I’ve got a friend who bar tends for Retrograde so I’ll see if he can get us VIP. And I have another friend who DJs at Candlelight, there’s a big thing happening there for the countdown. You guys can join us after you hit up Cooper, I’ll be there with my group.
Jess:
Aw man, you guys, I hate to do this but I think I’m coming down with something. I can’t make it.
Kennedi:
Are you kidding me right now?
Ben:
I’m sure Kennedi means “sorry you’re sick Jess, we sure will miss you.”
Sammie:
And Hot Connor.
Ben:
And Hot Connor.
Kennedi:
Yes, yes, we’ll miss you, Jess. Feel better.
Jess:
Thanks, everyone—Happy New Year!
Jess:
All right, Phase One is complete, I’ve cleared the schedule so it can just be me and Connor tonight.
Anna:
Perfect! And Phase Two is a go?
Jess:
I have the red sweater on as we speak. Over the red lacy contraption you made me buy.
Anna:
It’s called a bustier and trust me, that baby will pay for itself here in a few hours.
Jess:
If you say so.
Anna:
And you have the cards?
Jess:
Printed, folded, placed in an envelope.
Anna:
Then you’re ready. Fly, little bird. Fly and get laid.
Jess:
That doesn’t work but also somehow it does…
Anna:
Whatever, just go seduce your boyfriend.
Despite the grief I gave her, Anna was right about the bustier being a good purchase. I thought a strapless bra would have worked with the infamous red sweater, but she said lingerie would give me a confidence boost—and she was not wrong.
I felt so sexy when I put it on, I pretended to be in a photo shoot for like five minutes.
Fine, it was fifteen.
Paired now with tight jeans and a pair of red heels, and I’m basically ready to conquer the world.
But that doesn’t stop the nerves from creeping up more and more the closer I get to Connor’s place. He has no idea I’ve cancelled our plans for the night in favor of something a little…cozier. Anna promised that keeping him in the dark is a crucial part of the plan and, like the bustier, would be worth it. The inside of my car smells like the bag of Chinese takeout on the passenger seat, and I spend the rest of the drive convincing myself that this is a good idea.
“He’s not going to laugh at you,” I swear to myself. “Normal guys love when their girlfriend shows up in sexy clothes with lo mein. Normal guys love when their girlfriend wants to have sex with them. He is definitely going to have sex with you. He is definitely not going to tell you he changed his mind.”
My pep talks could probably use some work.
By the time I’m standing outside of his condo, my affirmations have been slightly effective, but when he opens the door, they fly out the window.
After seeing him as many times as I have, you’d think I’d be used to how good looking he is.
But no. No, it’s always still a surprise somehow.
A sexy, sexy surprise.
Wearing sparkly gold sneakers.
Because of course he wore them.
He flashes a bright smile to me before it falters a little when he sees the takeout I’m holding.
“Hey,” he says. “Come on in. What’s the bag there?”
“I, uh, I cancelled our plans,” I stammer as I walk in and stand by the kitchen counter, taking in my surroundings. I’ve never actually been here before, he always comes to my place. “I hope that’s okay. I, um, just…you know, I figured we could, uh, stay in instead. So I brought us some dinner. Lo mein?” I hold up the bag.
He’s still confused. But hopefully not disappointed. I set the bag down on the kitchen bar and go to take off the black wool coat I have wrapped around me.
His expression changes again when he takes in what I’m wearing. I smile in relief; his is not the look of a man who isn’t interested in me. He walks up to take my coat and brushes his hand gently over my exposed shoulder, sending chills down my spine.
“I am a big fan of this sweater.”
“You know, I got that impression,” I grin.
“Really? What gave me away?” he asks, stroking his hand up my neck.
“I mean, when you reorganized my closet and hung it front and center, that was a pretty big hint.”
“Mmm, glad you finally took it,” he leans in and kisses me on the lips, but it’s over too quick. “Hi,” he smiles.
“Hi,” I smile back.
“I’ll get us some plates, we can eat here at the counter.”
The time passes easily after that. Gone are the days of awkward conversation; we fill the hours laughing and joking, telling stories from years before, asking questions about the years to come. He tells me all about this huge account he’s got going at work that he’s eager to get back to. I tell him about my schooling for animation and how I’m looking forward to the next semester starting.
I don’t tell him about the internship I applied for yet…I’m afraid if I talk about it too much, then I won’t get it.
But as the clock inches towards midnight, I can hear Anna’s voice in my head encouraging me to move on to Phase Three.
Connor’s condo is unsurprisingly sleek and well organized. From the front door, the modern kitchen and large living room are in full view. There’s a small bathroom to the right and across the living room is a closed door I assume leads to his bedroom. We’re seated on an absurdly plush suede couch, the TV tuned into the New York City ball drop with the volume down low, when he offers me another glass of water (I am purposely staying away from alcohol and he said he was fine doing the same. Because he’s the perfect man).
“I’d love another glass, thank you,” I say and stand up.
“No, sit, I’ll get it for you.”
“Actually, I’m getting something out of my purse.”
I dumped my red heels over by the door a long time ago, so I pad in my bare feet over to my bag and dig out the envelope. We both walk to the couch together, but before I have a chance to sit down, he grabs me by the waist and pulls me in for another quick kiss. “I’m glad you decided we should stay in tonight,” he tells me.
“I’m glad you weren’t disappointed.”
“What? What are you talking about?”
“Well, I know how much you were looking forward to wearing those sneakers,” I tease.
“I can go put them on right now.”
“Come on, I brought something fun,” I grab his hand and lead him to sit on the couch next to me. “These,” I hold up the envelope, “are ‘Tell Me Something’ cards. But they’re not just any ‘Tell Me Something’ cards.”
“Ooo, that sounds promising.”
“Oh yes, sir, these are special. These are made for two people who are definitely in a real and not at all fake relationship.
“Ah,” he chuckles. “That sounds like a niche market.”
“Respect the cards,” I instruct.
He holds his hands in surrender. “I wouldn’t dream of disrespecting this very important part of your life.”
“Glad to hear it. Now the rules are simple: we each take turns drawing a card out of the envelope and reading it out loud. The other person has to answer and the cards have to be read in order.”
“I’m starting to see where Gemma inherited her board game intensity.”
“Darn straight! Now shush, I’ll go first.” I draw the first card. “Tell me something about your first kiss.”
He shifts a little bit, leaning back and moving my legs to rest over his. “Hmm,” he thinks. “It was with Madeline Steinberg.”
I stare and wait for him to elaborate. But nothing comes. “And?” I prompt.
He shrugs. “And nothing. The card just says tell you something. I told you something.”
I gasp. “Semantics! You threaten the sanctity of the game!”
“Then make better rules!” he counters,
“Fine,” I pout, and hold the envelope out to him.
The smile that crosses his lips is devilish as he draws his card and reads it to himself before reading it aloud. “Tell me something that you would do on a first date.”
“Eat dinner,” I state simply. I already knew what the question would be, and I had a much better answer lined up. But he ruined my ploy to get him to talk about kissing, and I’m pouting about it.
He laughs. “Okay, okay, fine. My first kiss was with Madeline Steinberg in sophomore year. And before you say anything, I know that seems really late for a first kiss, but you remember how scrawny and awkward I was. Madeline was the first person who ever really noticed me.”
“No, she wasn’t,” I murmur. I readjust my position on the couch, which prompts him to rub his hand over the tops of my feet. I begrudgingly offer my original answer. “Something I might do on a first date would be to bring over Chinese food and ask him to play a game I made up.”
He grins. “Are you saying you’ve done this before?”
“Yeah, obviously, it’s my signature move.” And just like that, we’re back on track. I grab the next card. “Tell me something that you would take with you to a deserted island.”
His massage on my feet continues, and it’s hard to focus because his hands are amazing. His thoughts are clearly on the question at hand, though, as he stares at the ceiling. “I’d bring my coffee machine.”
“To a deserted island?”
“That machine is amazing, you don’t understand.”
“Connor. De-ser-ted is-land.”
“I would never go anywhere that didn’t have Wi-Fi or electricity. I stand by my choice.”
I laugh and hand the envelope back to him. He stops rubbing my feet to take it from me and I feel the absence immediately. I run my palms along my jeans…I’m still not sure I’m ready for the next card.
Just like before, he reads it to himself first and I see his eyebrows go up. A smile creeps across his face and he looks at me, eliciting a giggle from my lips. “Tell me something,” he goes back to touching my feet, “that your partner does that turns you on.”
I draw in a deep breath and make eye contact with him—Anna said it’s important to make that connection even if it’s tough at first—and reply, “I mean, you’re already doing a pretty good job right now.”
He intensifies his massage and moves his powerful hands up my calves, alternating between massage and gentle strokes. I let my head fall back on the couch, relishing his touch as it works its way up to my thighs. “There’s just one more question,” I mumble incoherently. “But I don’t need the card.” I gather my thoughts and sit up, moving closer to him. I lay my palms on his strong biceps and glide them along his arms, intoxicated by whatever this is between us and letting it give me the confidence to ask him. “Tell me something you’d like to do to me.”
Connor plays with the broad neck of my sweater. “I think I’d like to start by taking this off.” His voice is deep and his eyes are dark.
Knowing that he’s as affected as I am emboldens me to grab his hands and place them at the hem of my sweater before raising my arms so he can remove it. Slowly, he lifts it over my head and leans in close, setting it behind me. The prickle of goosebumps raises all over my shoulders and arms as I watch his eyes drink in the red lace of the bustier. I’ll never doubt Anna’s seduction advice again. His breath gets a little more ragged, and he grips my hips, running his thumbs over where the lace met the waist of my jeans.
“Jess,” he growls.
“Yes?”
“I think I want to play a game that’s less telling and more showing.”
I nod. “Okay.”
“Are you sure?”
It’s scary how sure I am. “Absolutely,” I promise.
He doesn’t wait for any further invitation, and a bolt of electricity shoots through me as soon as his lips are on mine. I curl one hand around his neck and run the other through his hair as his fingers explore the lace over my stomach and breasts.
His mouth moves down my jaw and neck and I clutch his sweater in my fists. I pull at it frantically because I need to feel his skin. He responds without hesitation and I stare at his toned torso as long as I can before he dives back in to kiss my lips again.
He shifts himself to the side, his free hand sending heat through my body as it moves down my torso and to the waistband of my jeans. His knuckles move over my abdomen and I realize he’s undoing the button on my jeans. A brief wave of panic hits me; it’s been so long since another man has touched me like this…but even then, it had never felt so good. I run my hands over the smooth skin on his jaw as we kiss and just as quickly as the panic struck, it’s gone. He is cherishing me, he wants me, he…
Is he still trying to unbutton my pants?
“Can I help you there?” I ask against his lips. We both start chuckling.
“Fuck,” he mumbles. “I should have done that before I started leaning on one arm.”
“Open sesame,” I reply, popping the button and lowering the zipper. And also cursing myself for saying the words open sesame in reference to accessing my vagina.
But whatever, my high school fantasies are coming to life. Lying on a couch, making out with Connor Price, feeling his skin under my palms and his hand between my legs. I can’t even speak, I’m so lost in the sensations building up at my core already. I squirm beside him to give him better access, his fingers pulsing in and out, the pressure on my clit just right.
My voice comes back as the waves of a long overdue orgasm rush through me. I moan into his mouth as he presses the heel of his hand right where I need it most.
Somewhere in the distance over the rush in my head, I can hear the crowd of people at Madison Square Garden counting down. And as they all cheer for the new year, I’m being picked up and carried into the other room.