Kelly & Cassandra Ch. 01

"Is this the part where I find out you're a serial killer and you're going to chop me up and put me through a meat grinder?"

She looped her arm through mine. "No, honey. And that's fucking dark. See, that's one of the lovely benefits of dating women. Not that I really need to pitch the concept to someone who's on a date with me, but still, we tend to be a lot lighter on the violence and murder. No, I'm not going to kill you. I'm going to kiss you under this streetlight," she said, pointing a gloved finger to the yellow halogen bulb above, "And then I'm going to take you to the second-coolest bar in Chicago."

"Second-coolest?"

"Darling, I own the coolest bar in Chicago. Think of this one as my place with one hundred percent less Prohibition vibe but one hundred percent more gay-as-hell vibe. You in?"

"In," I said. "But, uh, can we do that kiss first?"

"Ah, we can."

It was a repeat of the one atop the tower. The fevered lips, tongue, the hand position, the desperation. Her gloved fingers teased the belted waist of my coat before taking a firm grip.

I felt a warm rush from the top of my scalp all the way down to the pavement. Her tongue teased mine, then traced my lips, and the rush traveled all the way back to my center. My fingers traced the bare skin above her collar and for once I was glad we were both the type of people who were negligent enough to leave a few square inches of skin bare in a Chicago winter.

As her lips parted mine and her tongue explored my mouth, I began to wish that we were indoors. In private. Someplace that would allow me to kick off my boots and then just take off layers until those fingers and lips were on bare skin all over my body.

She broke the kiss for a moment and took my hand to twirl me around in a full 360-degree rotation. It was like dancing with no music. I felt Cassandra's eyes drink me in, and it was the first time I'd felt someone undress me with their gaze and not been offended in the least.

I smiled and returned the favor. Her hair flew wildly from under the wool cap, matched by a beautiful twirl from the hemline of her coat. Cassandra's eyes, though, never left mine.

"Well," she said, her feet landing precisely where they began, just as mine had. "Seems we've got our footwork down, so would you care for a drink, dear?"

"Oh, right," I said. "I guess we have a date to finish."

"I know," she replied, opening the blank grey door to a blank concrete stairwell. "Tough work, going on a date with you, but I'll take one for the team."

--

She remembered my drink order. I didn't have to ask; she just planted us at a round high-top table with a heat lamp buzzing above it and came back with two Dark and Stormys.

The "second-coolest bar in Chicago" turned out not to be a normal drinking establishment as much as a temporary-looking set of walls set up around what was clearly designed to be a summer rooftop bar.

There was a bar whose entire top was a rainbow flag, around then tiny tables packed into the quasi-tent. Around half the tables were occupied, all by same-sex couples.

But despite the flimsy-looking walls and plastic-sheeted windows, it was warm both literally and in spirit.

"So," Cassandra said. "Aside from all the kissing - and trust me, we can back to that later - I promised you a date, and in my world that at least includes drinks. And for you, that's a Dark and Stormy, I believe?"

"I'm impressed you remembered."

"I'm a bartender. It's what I do. By the way, you look amazing."

"Thank you. You do, too."

"No, really. I'm always jealous of women who can look hot in a sweater and jeans. That was never me."

"I doubt that. You literally have a model's frame."

I sipped the drink. The ginger beer went down so smoothly that I hardly worried about the alcohol.

"Exactly. And that looks like shit in a sweater and jeans. But weren't you wearing something that was rather far from a sweater and jeans the last time I saw you?"

The blush spread crimson across my cheeks. The night Alex gave Cassandra my number, I'd been wearing a classic flapper-style dress and had even given it a full twirl in the middle of the bar.

"Yes, I..."

"And that looked really good too," she said. "Totally up my alley." Her top teeth were perfect and pearly white behind red lips and she smiled wistfully.

"And I'm glad that I'm apparently up yours too," Cassandra continued. "But I have to say, I'm not typically the introductory course to dating women, so I'm curious as to your journey up to this point, if it's not too rude." She paused. "Most women start with awkward makeouts with friends and stuff. You're on a legit date with someone who's been told she's intimidating, 'a little scary,' and has the worst RBF anyone's ever seen."

"You've probably noticed that my neutral expression tends to verge on a resting bitch face as well."

She placed her index finger on her nose and winked. "Secret?"

"Secret. Tell me?"

"I think that expression is sexy. On you, especially."

"And on you too," I said. And meant it.

She sat back, eyeing the tumbler of amber liquid, then leaned forward again. Our hands met atop the table, fingers playing until they found their fit again.

"Alright," I managed. "So, Cassandra Vann, who are you? You own a bar, I sense you're a bit of a math genius, you have this absolutely amazing 1920s style game, and for some crazy reason you're into me. Let's fill in some blanks."

"Oooh, interrogation-style?"

"Wouldn't an interrogation require that I actually ask a question?"

"You just did, darling." She squeezed my hand. "But okay. Yes, I'm a math nerd. It's one of my degrees, actually. Math and Comp Sci."

"And you own a bar?"

"I call it my retirement gig." She looked around us. Everyone else was still engrossed in conversations that looked a lot like ours: hands held, heads huddled over drinks. "Okay, so don't judge. I'm from Chicago - well, Winnetka - and I was always fascinated by flapper culture. So I've always been a bit offbeat."

I took another sip, letting her talk.

"Went to MIT for college. Should have gone to Stanford."

"Nice choice to have," I said. Another sip, my eyes locked on her.

"You?"

"I went to the University of Michigan and rarely feel inadequate about it."

"You shouldn't. Michigan's a great school, even if Ann Arbor winters are the same shit they are here. And Boston." She closed her lips around the rim of the glass and took a deep drink, eyes closed. "Pretty good. Sorry, where were we?"

"Boston. MIT."

"Right. So I majored in math and Comp Sci and then worked at a start-up. We sold the start up to a big tech company. Invested the proceeds. Worked there for a while. And then - poof! - I was thirty."

"And then?" The alcohol was starting to hit me, and my mind was backwards, telling me that since I had pretty much already decided to sleep with this woman, I better learn something about her.

"And then I stopped talking about myself and drank some while you told me what inspired you to wear a flapper dress to my bar."

Fuck. Well, no reason to lie.

"I was trying to catch your attention."

She raised her glass in toast. "It worked. I'd even give you half credit for making the first move."

"Nonsense."

"Sense," she said. "Are we going to bicker like an old married couple?"

"No. Definitely not."

"Yes, we are. We already are!"

"Nuh-uh," I said.

"Yuh-huh."

"Shut up, MIT girl. You're clearly way too smart for this nonsense."

"Sense, Kelly. I can do this all night."

I stopped. I wondered what else Cassandra might have in mind for doing all night.

She squeezed my hand. "The vintage thing drew you in, didn't it?"

If I was blushing before, I was out of control now. I took a deep breath.

"Honestly?"

"I don't like liars."

"I like it a lot. The aesthetic, the overt feminism, the confidence. And seeing you was just like..."

"It's what gives me confidence. This is how I look good, feel like myself."

I looked down at my own outfit. Was this me? Was it a uniform I was wearing for someone else? Why had I never thought about this stuff before?

"This is how I look like I just moved into the city from the suburbs."

Cassandra raised her eyebrow. "Are you unaware of what the lighting here does to that sweater?"

I looked down. In the bright direct light from above the tiny table, the loose weave of my sweater became apparent.

I found myself gasping and covering my mouth in horror. I'd known I was pushing my luck wearing a black bra under a cream-colored top, but...

"Well, um...I'm glad we're getting along?"

Cassandra raised her glass in toast to me, and somehow I managed to stifle stunned laughter long enough to clink it.

"To unintentionally shooting your shot," she said, our free hands still tightly clinging to one another.

We toasted and each sipped, eyes locked on one another.

"You know if we were somewhere private now, I'd just take it off, right?"

She kissed me on the lips. Quick, but purposeful.

"I think I'll be quite happy when we get there, seeing what I'm seeing now," she said.

"I can't wait."

A wide grin spread across her face. From a normal distance Cassandra was attractive, alluring, beautiful even. From up close, she put my body into a different gear. And she knew it.

"Michigan girls aren't so shy once you get to know them, are they?"

"I don't know about Michigan girls writ large. Me, though? Accurate. And," I said, tipping the mostly-empty glass, "A little slut fuel never hurt."

She pretended to gasp now, hiding her mouth with her glass.

"So I'm gonna finish that story now," she said. "In one final attempt to scare you off."

"Doubtful."

"Short version or long version?"

"Short. I doubt it's going to work," I replied.

"Fine. I'm your landlord."

Now that stopped me.

"I'm sorry, what?"

"See, I told you you'd want the longer version. You write your rent checks to CSV Properties, right?"

"That's right." The light went on.

"Cassandra Sara Vann at your service. So, now that I've creeped you out..."

"Wait, just to be clear, you own my apartment? Like, the whole building?"

"I own that building. I own this one too, the one we're sitting atop right now. I also own the one my bar is in. Used to own one more up on the North Side along the Blue Line, but the price was right to sell. Plus some other investment assets. So, scared you off yet?"

I leaned back and thought for a moment. "Is it supposed to?"

"No. But it has once or twice in the past. Just understand that if you think you're dating a bartender or bar owner, that's only part of the picture."

"Noted."

"Money fucks with people," she said. "I try to not let it do so with me. I grew up as an only child of parents who didn't have a lot of money. I don't really know how to use money except to make more money, so I pretty much don't. Spend it, that is. But it does open doors to power."

She tilted her head toward a couple near the far wall. "Those two gentlemen are married. Not to one another, of course, and one of them is a city alderman and the other a state legislator. Nice people to rub elbows with occasionally, but I try to leave it there. But money's fucked with both of them, let's say that."

"I'll keep that in mind next time Alex tries to leave you a tip," I said.

"Oh, we pool them anyway, and I never take a share. So rest assured that Alex's tip didn't go into my pockets."

She gestured to her dress, pulling open an empty pocket.

"One advantage of sewing one's own clothes is that my dresses actually have pockets." She tilted back her drink and savored it, crunching an ice cube between her teeth. "So now that you know I'm a bit of an oddball..."

"Wait, you really make your own clothes?"

"Yeah. Why?"

"It's just..."

"I know. Nobody makes their own clothes. But I have the time to do it, enjoy it, and besides, how the hell else am I going to get a closet full of clothes that suit my preferred style and don't look like they were made for a costume party?"

She had a point there. I'm not exactly sure where to find the flapper dresses at Nordstrom or J. Crew.

I swallowed. "If this, like, becomes a thing, would you be willing to make me a dress or two?"

"Darling, I'd make you a dress or two even if you don't want to date me. But then you might need to at least pay me a nominal amount, plus you wouldn't have the benefit of me taking it off you."

"Don't tease." There it was again, that tingling anticipation. I leaned forward again, face inches from hers. "I'm just a nice girl from the suburbs. Teasing me is mean."

"I'm not teasing, I'm promising. And I think I'd like to see pretty soon if that nice girl from the suburbs has something else under that exterior."

I swallowed again. My throat was parched despite the drink. This was happening. Yes, my girl crush from my building lobby was actually sitting across from me and directly propositioning me. Yes, we had been kissing passionately before. Yes, I had loved it and it had turned me on incredibly. Oh well. There was no backing out now.

"I think I'd like you to find out," I said.

--

My sweater lasted approximately two seconds longer than my jacket and shoes, and none of them made it past the entranceway of Cassandra's home. She didn't bother hanging her jacket, either.

I swept my eyes around the dark apartment. The kitchen was to my right, and the living room ahead, with tall, velvet-curtained windows and antique-looking wooden furniture. A leather sofa sat opposite a tall cabinet that I assumed concealed the television.

"I'd show you the place," she said, "But let's be honest. It's the same layout as yours, just with a massive bed/bath suite added. I use the other bedroom as an office. Same kitchen..."

"I don't take much notice of kitchens. Bedrooms, though..."

There was surprising strength in her lithe figure. It was a contest of whether she could pull me down the hall faster than I could push her.

"Why don't you live in the penthouse, if you own the building?"

She stopped at the closed bedroom door, brushed aside my hair and kissed the side of my neck. "Because it rents for seven grand a month, and remember what I said about money. What the fuck would a girl like me do in a penthouse?"

"Me," I said. "You'd do me in a penthouse."

"For someone who hasn't been on a first date in quite some time, you do have some good slut game."

I smiled at her as she opened the bedroom door. "I hope that opinion will still stand tomorrow morning."

"Well, darling, there's only one way to find out."

I gasped when her hands traced my sides. This, of all the moments, was when it finally clicked that there was no turning back. My shirt was off, her hands were on me, and I knew that the next time that sweater went over my head I'd have wiped away the "bi-curious" label and replaced it with something new.

"Just let me know if anything feels uncomfortable," Cassandra said, her nails tracing the waistline of my jeans.

"I will." My own hands had risen again to the nape of her neck, pulling her lips to me. "But otherwise, just do this, okay? Forget that it's my first time, or our first time. I want this. I want you."

"Mmm," she said. Her hands were in my hair again now, gently tugging on it as our lips met and parted. I could taste the Dark and Stormy on her lips and the whole thing was delectable. Our tongues teased each other again and my body eased automatically down onto her queen-sized bed.

Cassandra slid on top of me, hiking up her dress.

"Or would you rather it come off?"

"Off," I said.

My jaw literally dropped as she undid a button and slid the long A-line over her head. The red-shaded lamp cast a dim glow, but it still reflected off her pale, slender torso. A black lacy bra not unlike my own and a matching pair of hipster-cut underwear wre all that interrupted the view.

"I know," she said. "We do kinda match, don't we? Dark hair, pale skin, black bra..."

"Come here," I said.

She traced a red-painted fingernail down my centerline, all the way to my waist, circling my navel. Then back up, over my bra, between my breasts, and then past my neck. She lifted my chin and held my gaze.

"Gladly, darling."

Cassandra's lips met mine, and instead of going in for a deeper kiss she pulled gently on my lower lip. My hands wrapped her narrow frame, fingers tracing her spine. I didn't mean for them to slide all the way down, but soon one had slipped inside her underwear.

She'd delicately pushed my chin further up. Now she brushed my hair aside, kisses moving from my lips to my jaw to the side of my neck.

My breath caught, then released as her tongue began to trace my neck tendon down to my collarbone.

My legs curled around hers, holding her in place. Her smooth torso brushed against mine and the sensation was divine. Heat spread everywhere across my skin.

Cassandra raised her eyes to mine again. I pulled her to me, hands twisted into her short bob, and kissed her. This time it was my teeth on her lip, my tongue probing her mouth; me exploring her. I felt her hands squeeze between us, unfastening the button on my jeans.

"They clash with the bedspread, darling." She pulled them off me, sliding them deftly down my legs and tossing them into the dark room. "There. Now we're even."

I half-tackled her, tossing her onto the hunter green quilted covers - she was right, though, they did clash a little with my jeans - and reaching behind her.

The two hooks - benefits of small tits, right? - came undone immediately and I flung the bra in the same direction my jeans had gone.

Cassandra purred. "In case I didn't mention it, I think I like you."

I pounced on her and kissed her again. The taste of the drink was gone. Now it was just her and me: us. And by now there was so much kissing that here was only one flavor. My jaw worked up and down as we furiously made out, my hands back in her hair and tugging gently.

I let one hand drift down, circling her nipple with my fingertip.

"Mine now," I growled, loving the sound of my own voice.

Somehow my bra fell away. I didn't notice her do it, but it sent a huge rush through me.

"Fine then. Mine," she said, my C-cups finding themselves quickly in her expert hands.

I heard myself moan as she rolled one nipple between thumb and forefinger, then the other.

My head dropped to her neck, kissing up the side and nibbling on her ear. The hands - her hands - massaged my tits. She was delicate and firm at the same time and whatever she was doing was working for me. Specifically, for my pussy.

"May I?" I slid down her, inch after inch of her pale skin rubbing against mine. As my nipples grazed her stomach, I felt my knees go weak and I thanked the heavens that I wasn't trying to stand right now. No fucking chance.

I took a deep breath. My face was inches from her chest, her nipples firm in the middle of the pale pink areolae.

"You may." She sounded like a fucking queen bestowing a gift upon a royal subject.

Maybe she was. My mouth closed around her left nipple, my tongue sliding from the tip around its circumference. She sighed and I raised my eyes to her face. Her eyes were closed and a smile crossed her lips, her hands resting behind my shoulders.

I don't know what I expected, but I didn't expect the instant rush of wetness in my already-soaked pubic area. As my mouth and hand combined to work on Cassandra's breasts, my own body was catching fire.

The quilt was no longer cool under my free hand. Everything was the same body heat, the smell of sex beginning to fill the air.

Cassandra bit her lip. Her nails, short though they were, were digging into my back. I wanted her to dig harder.

With no warning, she flipped me onto my back.