A Little Bit Cupid: A Collection of Short Stories

by Lady Boss Press

  “You didn’t,” she coos. “You were perfect. The Rileys are ever so grateful. Should we Venmo you, or do you want cash? I can take up a collection.”

  And, oh. Oh, ho. Ho, no, no. What I thought was anger before turns out was a mere flicker of annoyance. But now? A bottomless well of all-caps RAGE turns my vision tunneled and red at the same time. I wasn’t the hooker in my Pretty Woman scenario. He was. And my sisters, those traitors, went in together to gift me some dick in the same way we typically go in on graduation gifts and nice things for our parents at Christmas. I’m not totally sure the shriek I hear is coming from my own mouth but judging from the look of horror Judd is giving me, it’s a safe bet.

  “Aw shit,” says Drunk Darby. “I looked away from you and forgot you could still hear me.” As though that excuses it.

  I close my eyes and think what would Jana do until clarity comes to me. She wouldn’t engage. She would give this party/nest of snakes an Irish goodbye. And so shall I. New year be damned. I’ll go home and kiss my reflection in a mirror at midnight for luck. Surely that’s a Thing. Even if I just had to invent it. I’ve just pulled out my phone to order a car when a juniper-and-sandalwood scented arm steers me into a corner.

  “Kiera,” its owner says, brown eyes locked on mine like intensity will drive out the words I just heard my least favorite sister say. Well firstly, they won’t. But secondly, I’m closing mine so his sheer attractiveness won’t sway me. “Can you open your eyes and look at me?”

  “Nope.”

  Just like he said when I asked him about his career in the bathroom. I hope he appreciates the mirroring, and how annoying it is when someone doesn’t elaborate. Because it is. It is super annoying.

  “Stop—just stop calling a ride. I’ll take you home and explain.” Now that makes me open my eyes. Long enough to look down and confirm a—sweet Mother Mary—two hundred-dollar fare for a fifteen-block trip.

  “I’m good,” I tell him coolly, before chancing a glance up. His eyes are wider than I’ve ever seen another person that isn’t a cartoon character and he’s looking at my confirmation screen.

  “You are not,” he says in a tone much higher than anything I’ve heard from him yet. “That is an ungodly number.”

  I must agree. And yet, I have no other choice. Because walking away from every single one of these assholes, even if I have to stop paying my utility bills as a result, is the energy I need to take into the new year. So I close my eyes again as to avoid temptation, and feel my way on out of the bar proper into the full waiting area before I open them.

  “Listen, children,” I say. Everyone waiting to get let in is absolutely at least ten years older than me. But I am the wise one. “My babies, I must warn you. There is a tall, dark, and handsome man inside. I do not know his name, but you will know him when you see him. He has a weird kink. He really, really, really loves wedgies. If you give him one every time you walk by, he’ll have the best night of his life, and aren’t we all here to spread happiness?”

  With that, I sweep into the night, and the most expensive trolling of my life.

  Everyone is dead to me.

  Fucking Jana Aston.

  Bargaining

  The good news is, I definitely don’t have scurvy. The bad news is, I do have a hangover. I suppose I didn’t need another gin when I got home last night, but something had to wash the taste of that fare out of my mouth. And then I got prompted to tip, and I felt shamed into it because after all, this guy gave up his holiday to help other people enjoy theirs, and I was still feeling vaguely guilty about not recognizing that about Dave last night.

  So then I needed another gin after I realized that I spent the equivalent of an entire spa weekend on a single hour. Despite the fact that the sex I managed to accomplish during that hour was pretty good. Okay, really good.

  The group chat, predictably, has been popping while I slept it off.

  Kiera

  Kiera

  Kiera

  Kiera

  All from different sisters. In between those are reports on the levels of everyone else’s headaches, and a couple vague plans for brunching. There’s another text from a number I don’t recognize:

  Kiera

  Hmm. That one I’ll answer, since it isn’t from a Riley. Probably a co-worker who got a new phone over the holidays or something.

  You got her

  Then I abandon my phone in favor of a really long shower. And a really strong bloody. In the shower. I have a little cupholder in there that was the most useful White Elephant gift I’ve ever gotten from a shitty office party. Feeling far more human, if still a tad sore downstairs, I change into fresh pajamas to enjoy my day off.

  It’s Vitamin D. You still pissed?

  I most certainly am. But less so at him than at my family. After all, he might be a prostitute—excuse me, sex worker—but who am I to argue with anyone’s career choice? It’s honestly sort of nice that he’s following up with me. I wonder if he needs a Yelp review. I’d probably give him a solid 4 stars. 5 for the sexing, minus 1 for the deception. Although the true crime was a nice touch. He did his research. So maybe 4 ½ stars.

  Nope.

  I see why he likes that word. It’s vaguely mysterious, and yet final in a way that makes it hard for people to come back at you.

  Wanna grab a coffee?

  Holy Mary, he’s seriously hustling for that good review. I wonder if this means he has otherwise bad ratings.

  Nope.

  Honestly, coffee sounds fantastic, but I’m already in clean pajamas and there’s always the chance that Netflix has added more true crime programming since it’s the first of the month. Also, this is my new favorite word. I wonder if I have any coffee beans to make my own.

  Oops.

  Oops? What does oops mean?

  Look outside

  Oh my god, no. I peek through two slats of the blinds. Yep. That’s him all right. Leaning against a sporty-looking car, holding up two paper cups, looking far more edible than anyone has a right to on New Year’s Day. I cannot believe he got my address.

  DRUNK DARBY, YOU ARE DEAD TO ME I send to the group chat.

  Then I make a quick assessment. Sex workers are historically the victims, not the perpetrators of crimes. Except for Eileen Wournos, but there were a lot of extenuating circumstances happening there. Plus, again, all my sisters clearly know he’s with me, so he wouldn’t be able to get away with much. No one, and I do mean even the most hardened axe murderer, would relish the idea of facing down my seven sisters when they’re on the warpath.

  The next two assessments involve how clean the apartment is (always a danger when one is depressed) and how my face looks. I feel fine about both. After all, I’m the one with the power here. If he wants a good review, he won’t be judgey about toothpaste in the sink or how dark the circles under my eyes are.

  I buzz him up and wait at the door to receive my coffee. I hope it’s good and foofy. This is not the time for a cold-brew. I need the sort of comfort that is exclusively found in heavy cream and sugar.

  After all, I’ve just discovered I’m the type of girl who sleeps with gigolos.

  His smell of juniper and sandalwood mixes with the sweet scent of a latte and precedes him up the stairs. Wow, I must really have a vitamin deficiency, because I’m already ready to throw all my scruples away for a second round even before he appears and hands me a cup of something that appears to be caramel-flavored.

  Okay, 5 stars, but I’m not telling him that yet.

  He follows me into my living room without a word. Two can play that game. I think I’m getting better at it, anyway. I turn on the tv and offer him a blanket. My luck must have returned, because there’s a whole new documentary just waiting for my attention, so I turn it on. If Vitamin D wants to chat, he’ll have to work for it.

  But he doesn’t. He just watches silently with me. After he finishes his coffee, he transfers one hand to my leg. And just leaves it there, heavy and warm, not roaming at all.


  I really, really like how gentlemanly he’s being. And yet, having his hand so close to other parts of me is reminding me just how much I would prefer the roaming. So I grab his hand and move it up.

  “Here’s the deal,” I say, and then gasp as his fingers start gently moving over my flannel pants. “The deal is that we can continue to do this, but I will not be paying you.” He keeps sliding his fingers up and down for a moment before answering.

  “Okay.”

  Okay, indeed. I slide my pajamas down so he can really touch me and the skin on skin contact is almost too much. Wow, I really haven’t been getting laid enough. Or maybe I haven’t had anyone this talented between my legs before. Coin toss. He swirls his finger directly over my clit and I almost hit the ceiling.

  “You don’t happen to have another condom on you, do you?” I ask, slightly breathless. He doesn’t answer, of course, but rather uses his other hand to extract his wallet, not stopping the strokes on me until the little foil packet is out and ready.

  Then, in a fit of absolute genius, I finish taking my pants off and move to the floor as he rolls it down his hard, thick length. This way, as he lines up behind me, we can both still watch true crime.

  I know.

  I’ve won this year already, on day one.

  I know.

  I have to shut my eyes briefly when he pushes in slowly, filling me up completely, and snaking his hand back around to keep playing with me. It takes a second to adjust, and then I’m eagerly rocking back to meet him again and again until he presses down hard with his thumb and I come even harder than I did last night. It only takes a moment until he joins me, predictably not making any noise beyond a sharp intake of breath as he thickens and pulses.

  Afterwards, we cuddle on the couch and finish the doc in silence. This is by far the best deal I have ever made. I’m getting the benefits of all his professional experience, and not even paying for the privilege. Something tells me that somewhere, Jana Aston is smiling.

  Depression

  Kiera, Kiera, Kiera.

  It never ends. My sisters are absolutely insatiable. Much like me these days, I have to admit. It’s been a month now, and I’m still taking vitamins a couple times a week. I haven’t forgiven Darby so much as I have accepted that sometimes good people do bad things that have unexpectedly pleasant consequences.

  She keeps trying to talk to me about it, but I refuse. I don’t want to know. This winter has been bearable as a result of my newfound sex life, but that doesn’t mean I’m going to name the puppy. He’s still Vitamin D in my phone, and so he shall remain.

  Also, I did get a sun lamp, and that might be helpful too.

  But probably the sexing is the most important part of my regimen. I’m slightly concerned now that my sisters aren’t getting as much as I am, because they continue asking for gory details. Well, Maggie and Darby do. Bridget and her accidental husband seem to have a real active sex life, and the others don’t chime in too much either way. I worry most about Maggie, because she very recently started a torrid fling with her boss. And if she’s this interested in me, it can only be because she hasn’t been getting enough of her own.

  WHAT I finally answer. Listen, I am happy to rub it in that I’m having more and better sex than Darb, but it’s getting slightly tiresome doing the recaps all the time. Especially when I know Judd would be delighted to give her a vitamin of his own.

  Look outside

  Dammit. I peer through the blinds, and yep. There she is, leaning against her ten-year old Jeep, holding a bottle of gin.

  The next time I move, I’m leaving no forwarding address, I swear.

  I buzz her in and leave the door open as I head to the kitchen to collect tonic and limes while she crashes her way into the living room. It’s beyond me how one person can make so much noise doing so little, but she’s been this way as long as I can remember. Her feet are the stompiest, she bumps into everything, doors never shut around her when they can slam… Maybe it’s her way of making up for being on the younger end of the eight of us.

  “Wanna watch TV?” I ask hopefully. It would be nice to get at least one of my sisters on the bandwagon, and I’ve got several episodes of Dateline recorded.

  “No, I want to get you drunk and have a heart-to-heart.” I was afraid of that. And yet she went to all the trouble of bringing the gin, and I already sliced the limes so at this point it would just be pretty rude of me to kick her out.

  “Nope.” She can get me drunk, but I’m in no mood for real talk.

  “Fine, we can do it sober.” I should have known you can’t nope a Sister. “You’re making Dylan sad and it’s affecting me in the following ways—”

  “La la la!” I jam my fingers into my ears and sing. His name is Dylan? I didn’t want to know that! And now I can’t un-know it. I’m not changing his name in my phone though. She pulls my fingers out.

  “In the following ways. He’s stopped overlooking my tardiness like he did at the beginning of the year. He no longer brings me coffees. Yesterday he told me to stop making unofficial gossip newsletters and circulating them at lunchtime. And now I have nothing to do for the hour before lunch.”

  “Except… work. Wait, the D’s your boss?” Darby works at a local television station. Social media. She’s really good at it too. Whereas most of the channels just transcribe headlines to their Twitter feeds, Darby always manages to come up with funny or clever alternatives.

  “He’s a producer, so basically yeah.”

  Hmm. That’s interesting. A news producer probably has a lot of good stories about local crime. Maybe I’m not furious to know this after all. But I still have questions.

  “Why is he sad?”

  “Well, Keira, you’ve been sleeping with him for a month now, and I just told you his name. You’re treating him like a booty call, but he deserves better than that. He’s relationship material.”

  “Oh my God, Darby.” Now I really need that drink. “He is my booty call, why are you intervention-ing me over it? And also, why did you pay your boss to sleep with me? That’s just weird, and probably a real HR concern as well.”

  “Oh my God, Kiera. I didn’t pay him, that was a joke. You know when I’m drunk I think I’m real funny. I invited him out—and maybe mentioned you in particular—because he just moved here and didn’t know anyone. Also, his podcast.”

  Shoot, now I feel slightly bad. I didn’t know I was his only friend. Although it’s a relief to find out he isn’t a professional sex worker. I guess that explains a few things, for example why he so easily agreed to sleep with me for free.

  “Wait, podcast?” I am continually a step behind here.

  “Over the Kill? True crime all the time? I guess if you didn’t know his name or his job, there’s no reason you would have known that either.” But I’ve already stopped listening.

  Podcasts. Of course! It’s the next logical place to get my true crime fix. I can’t believe the D has a true crime podcast. He just keeps on spreading that happiness. Suddenly, there’s a screeching of tires in the parking lot. I peer between the blinds yet again, and of course, there’s Maggie jogging towards my building.

  “Don’t let her—” Darby barely gets out before I’ve hit the buzzer. Then Maggie flings open my door, panting, and any possible hope I had of a quiet Saturday is dead.

  “Kiera! Your booty call is affecting me positively in the following ways! Jana Aston pays so much more attention to me when I tell her all your stories. And once she finishes stealing the good parts, she said she’ll dedicate the book to me. Oh, I’d have a gin.”

  “That’s so typical of you, only thinking about yourself, Maggie,” says Darby, apparently having forgotten her own list of grievances. “What about Dylan’s feelings?”

  “Wait a minute. You’ve been forwarding all my sex stories to your writer friend? I thought you were living vicariously.” I hand her a gin.

  “Oh, no, she is. You know Jana.” I actually don’t, though. “Anyways, it
behooves me for you to keep on having anonymous sex with the D.”

  I have to sit down for a minute and process all of this.

  The D has never required a Yelp review for his services, he was just interested enough to call the next day. It’s entirely possible, knowing this, that my objectifying nickname for him is a little rude. And maybe all of my behavior, actually. Darby has an excellent point that I haven’t thought much about him in any of this, except for the parts about how I really like my booty call bringing me coffee and always letting me pick what to watch.

  I’d been extremely reluctant to date this winter. But when I think about what I was thinking when I made that decision, it had a lot to do with not having any energy. When you can’t clean your house or wash your hair, you probably aren’t going to make a good impression on any potential suitors. Assuming you even show up to make your bad impression at all.

  The D—Dylan—already knows what a mess I can be, because it didn’t occur to me that he was a real person.

  The devil on my shoulder, Maggie, isn’t even really dissuading me here. She doesn’t care if he gets humanized to me, as long as I keep sending her the highlights to pass along. Humanizing is the process, as all true crime fans know, by which you try to get a potential murderer to see you as a person and not a victim.

  Which is how I know I’ve been wrong all along.

  I have been the psychopath, not Dylan.

  All this time. And I have been the bad guy. I heave myself down on the couch, but it isn’t enough so I melt down and flip until I am upside-down with my head on the carpet. How could I have been so wrong about everything? I guess pretty easily. I’ve never been known for my great choices. But still, this feels like a new low.

  “Wait, what do you mean Jana Aston likes to live vicariously?” I ask Maggie.

  “Well, she hates parties and going out and most things that aren’t cats or coffee. So it works out nicely for her that I have so many weird stories about us doing what we do.”