The Date Dare

by Tara Sue Me

It’ll be okay.

  I hope.

  “You know what your problem is?” she asks.

  “No,” I reply because now I’m thinking it’ll be better if she says it first.

  “You’ve been dating the wrong type of woman.”

  Of course I am, because none of them are you.

  I don’t say it, but I think it. In fact, I don’t open my mouth at all for fear those exact words will come spilling out on their own.

  “Well?” She asks proudly and crosses her arms over her chest like she’s waiting for me to give her a round of applause.

  “I don’t think I’d describe the arrangement Alice and I had as dating.”

  “You’re right,” she says. “Let me rephrase. You need to start dating the right type of woman.”

  There is no way I can argue that. She’s absolutely correct. Unfortunately, it’s not about finding the right type of woman, because there’s only one woman for me. Except she doesn’t know that. So for now, I play along with her.

  I sit back in my seat. “And I suppose you know the right type of woman that I should date?”

  “Of course I do,” she says with the confident smile I love so much. “I know everything about you. I know you better than you know yourself.”

  I didn’t doubt her, but I want to mess with her a little bit. “Oh you do, do you?”

  “Oh, yes, absolutely.”

  She looks so sure of herself, and I shouldn’t do what I’m getting ready to do. Unfortunately, I can’t help myself. “Okay Miss smarty-pants, when I’m eating pussy, do I prefer the woman to be laying down, sitting on my face, or ewww gross, people do that?”

  She tries to cover her surprise at my question but she’s not completely able to. Although I have to hand it to her, she recovers pretty quickly and answers, “It better not be the last one.”

  I nod. “I’ll give you that much, it’s not. But tell me, which of the others is it?”

  She’s actually thinking about it and I can’t help but wonder if she’s imagining me between her parted thighs. “Lying down?”

  “No.” I lean forward. I don’t think anyone’s listening, but I need to ensure they can’t hear what I’m about to say. “I want you on my face. I’ve found that’s the best way to both taste you and to get my tongue inside you the deepest. Although, granted, I’m not really picky and I’ll eat your pussy anyway you give it to me.”

  Her mouth still open when I continue, “Next question. When you take me in your mouth do I let you lead or do I hold your head still while I fuck your face?”

  Her cheeks grow red and I can she’s picturing herself on her knees in front of me. I shift in my seat because suddenly my dick is doing all it can to bust out of my jeans and flag her down.

  “Ummm.” She looks everywhere except me. “You’ll let me lead.”

  “No. I’m pretty much fifty, fifty on that one. Could go either way, depending on the day and my mood.”

  She looks ready to slink into the seat and she’s completely stopped eating. I think about stopping, but decide to keep going.

  “Next one,” I say.

  She holds up her hand. “I think that’s enough. I said date you, not fulfill all your sexual needs.”

  “If she’s the right woman for me, they’re one and the same.”

  “This entire line of questioning is stupid. I said I could find the right type of woman for you to date. I wasn’t talking about knowing you like that. Besides, I doubt you know my sexual preferences.”

  I should take her at her word and shut up. I should stop while I’m ahead, and let it die. If I was smart, if I had a brain in my head, I would. But I can’t. Looking in her eyes, I tell her, “I know you won’t sleep with anybody before the fifth date. I know you like a lot of foreplay because you think it’s hard for you to come. But in reality, I don’t think you’ve ever been with a man who turned you on that much. I know you like dirty talk while you’re fucking and you like to cuddle and kiss afterward. And I think somewhere deep inside you fear you’ll never find a man who can satisfy you.”

  By the time I finish talking, her mouth is wide open in utter and complete shock. All I can think is how badly I’ve fucked up because I just showed her my cards and now she knows how I really feel about her. I’m doing my very best not to let on how petrified I am when she closes her mouth with a, “Haha!”

  “What?” I ask.

  She shakes her head with a knowing glare. “That’s like, eighty percent of women. I bet you got that from reading a magazine O2 left at your place.”

  I can’t tell if she really believes that or if she only wants to believe it because it makes her feel better. But, for right now, I’m not going to push it. I’ve already said enough about both of our sex lives for one evening and I don’t want to push her away.

  “I’m sure I did,” is all I say.

  We both drop it then, allowing some of the tension to leave the table. In fact, we don’t talk about anything having to do with relationships until we’re finishing up dessert and she brings it up again.

  “Like I said earlier, you really should let me set you up with someone.”

  I roll my eyes. “Really Darc? Back to that? You really think you can find someone for me better than I can find myself?”

  “I’m sure of it,” she says and then pops the last bite of her double mocha cake in her mouth.

  I almost tell her she’s on just so it’ll hopefully wipe that smirky grin off her face before I’m tempted to kiss it off. “That’s okay,” I say instead. “I’ll pass.”

  But it appears as if in remembering everything about how Darcy likes sex, I forgot one thing: she likes to play dirty. Therefore, I’m not at all prepared when her grin goes from smirky to downright evil.

  “Come on,” she says, proving once and for all how well she does know me because the next three words are my own personal kryptonite. “I dare you.”

  Chapter Three: Darcy

  “The only thing worse than a boy who hates you: a boy that loves you.” Markus Zusak

  It’s a prick move on my part. Before the words even leave my mouth, I know I’m stooping low.

  Across the table, he’s looking at me with those intense eyes of his. “You’re playing with fire, Darc.”

  Darc. There he goes with the nickname again. Honestly, I don't know what has gotten into him. It has been months since he last used that nickname for me. The entire evening with him has been one surprise after another. From him showing up alone, to the admission about O2. The sex talk about what he likes. Not to mention, his long discourse on what he thinks I wants from a man in bed.

  No. I will not think about how right he was or try to figure out how he knows.

  “Why?” I ask him. “You can’t honestly think I can do worse than you can. Seriously, let’s take a few minutes to look over your last few dates. Or, wait…what do you call a person like O2? I’m not sure date fits? Maybe the ‘scratcher of my libido itch’?”

  No answer from him. He continues to stare at me with those intense eyes.

  Finally he speaks, but his voice is much more coarse than normal. “You know I can’t turn down a dare," he says. “But, instead of getting mad at you for using that against me, I’ll make you a deal.”

  “What kind of a deal?” Normally I would never bother asking, because normally no matter what deal he came up with it would benefit us both. But tonight, I’m not so sure. Not now. Not with this new, definitely not normal Elliott that I can’t quite grasp.

  I try very hard not to fidget as I wait for him to answer my question.

  “I agree to take you up on the dare,” he says. “But in return, I dare you to let me set you up.”

  “We get to set each other up?” I ask. “Will we double date, too?”

  “No,” he’s quick to answer. “I don’t think that would be a good idea. You and I would probably spend the entire time talking to each other.”

  I laugh because I can totally see that happening. Elliott gives me a
big smile, and for this one perfect moment, we’re back to where we’ve always been.

  * * *

  Later, after we say our goodbyes, when I’m back at my house alone, in bed, and not able to go to sleep, I give myself the freedom to think. I can’t lie and say I have never thought about Elliott that way before, in a sexual way. Seriously, he is a fine looking man with a fine looking body, and he knows how to use it. But earlier tonight, when he asked those questions about his preferences, I had a strange feeling he wasn’t talking about a date. I think he was talking about me.

  No matter how many times I might have fantasized about Elliott that way, it had never been as vivid as it had been listening to him vocalize it. Even now, as I let my hand drift between my legs, I hear his whispering that he’ll take my pussy anyway I give it to him. And though I’m sure he meant it hypothetically, I close my eyes and it’s the realest thing I’ve ever felt.

  I’ve held his hand before, I know what his fingers feel like and it doesn’t take much to imagine them sliding up my thighs and his hands parting them so he can slide in-between them. I don’t know how he tastes, but I know the feel of his lips and just the thought of those lips nibbling along my inner thigh is nearly enough to send me over the edge. But I hold out until I’m almost positive I can feel his warm breath teasing about how wet I am for him. His growl of masculine approval at how much he turns me on is music to my ears as he makes good on his promise about his tongue.

  After my climax passes, I wait for an icky feeling to come over me. It should, shouldn’t it? He’s my closest friend, and even though I think that should make him feel like a brother, it doesn’t. Instead he feels exactly like what he is - a guy I’ve been friends with forever, who also happens to be hot as hell.

  It doesn’t make me strange or a pervert. It makes me a normal female. The fact that hearing him talk about the way he’d pleasure me was a turn on? Again, normal female reaction. Getting aroused as he described the various ways he might use me if I went to my knees in front of him? Seriously? What other reaction could I possibly have?

  This does not mean, however, that I will ever tell him any of this. Not that hearing him talk about sex turned me on and definitely not that I got myself off while thinking about him.

  Hell to the no, underline, bold, and extra exclamation points.

  Because as soon as Elliott sees me as someone other than his best friend, that’s when I’ll become whatever thing he sees. I can’t stand the thought of not being his best friend anymore. Lovers came and went. Heck, I’d personally seen Elliott with at least two different women each month. They were nothing to him. Likewise I’m sure, he was nothing to them.

  But I’m not like O2, nor do I want to be. As wonderful and mind-blowing as I’m sure it is to be in his bed, I’d never exchange that for our friendship. Elliott has been the one constant in my life that has never left me. My parents divorced when I was eleven. My dad died five years ago. Only Elliott has been my steady support through it all.

  So if I had to pick between sex with Elliott and Elliott my friend, friend Elliott wins every time. I can give myself orgasms. I can’t give myself a new Elliott.

  Chapter Four: Elliott

  "God gave men both a penis and a brain, but unfortunately not enough blood supply to run both at the same time.” Robin Williams

  I arrive at work the next day at an ungodly early hour at our administrative offices. The admin looks up at surprise when I walk in, but I only nod and continue toward the back where I work during the off season. Before heading to my office, I stop in the break room and make the strongest pot of coffee I can both stand and get away with.

  I realized the deep shit I was in once I got home the night before. I’m still running on much too little sleep, but fortified by the obnoxiously strong coffee that I’m making the right decision.

  When I agreed to Darcy’s ridiculous dare last night and made the condition that I would also pick a date for her, I’ll admit, my initial plan had been to get back at her. Don’t get me wrong, I would never set her up with a jerk or anyone who would be less than respectful of her. But a self absorbed jock who could only talk about himself? Yes, and that would serve her right for suggesting the dare in the first place.

  But I can’t do that to her.

  I take a sip of the coffee and burn the roof of my mouth, but it doesn’t distract me from my main goal. I pull the box of business cards I’ve collected over the years and look for the one belonging to one of the few men I’m acquainted with who is good enough for Darcy. I half hope I can’t find it and will have to fall back on my plan of egotistical athlete, but within seconds my fingers wrap around the innocent cardstock that will both bring my damnation and serve as my salvation.

  Tate Maddox.

  Most people won’t recognize the name and that’s okay because that’s what Tate wanted when he left behind the world of professional sports and the name everyone does know - Tommy Maddox. After a wildly successful five years in baseball, Tommy did the unthinkable and walked away from everything, claiming he didn’t like what fame was making him into and stating he didn’t need any more money.

  Yes, he actually said that.

  Now he runs a sports camp for underprivileged children. It’s the exact kind of thing Darcy loves and I can see her getting into. I can use one hand to count the number of guys I think might be worthy of Darcy. Tate is the only one who is her age and also single.

  I tell myself I’m doing the right thing. If I can’t have her, I need her to be with someone who will respect her and love her for who she is. Who can appreciate the woman underneath the gorgeous exterior. And, frankly, someone who is so much better for her than I will ever be.

  It’s probably the most painful thing I’ve ever done, but I call and speak with Tate. He’s shocked to say the least. Plus he remembers Darcy. Apparently, she was my date at an event we all went to several years ago. I don’t have any memory of it, but Tate certainly does. He mentions several times that he always thought Darcy and I would get together. I remind him that she’s my best friend and I don’t think about her like that.

  Yes, I lied.

  Before we hang up, I give him her number. I ask him to wait until tomorrow to call her because I want to give her a head’s up. Actually, what I want to do is to give her a chance to call this whole thing off, but he doesn’t need to know that.

  Unable to put off the inevitable, I call Darcy and of course, she picks up on the first ring.

  “Hey, Elliott,” she almost sings.

  “Someone must have gotten some sleep last night,” I tease back. I’m glad one us did. It for damn sure wasn’t me.

  “Not really,” she says. “But I’m sitting here thinking about you and trying to decide who would be the best person to set you up with.”

  She’s so excited about this and I tell myself that I’ll act the same, even if it kills me.

  “Funny,” I say. “I was just doing the same. However, I’ve already decided who your perfect match is and called him. He’ll be calling you tomorrow.”

  “Wow. That was quick.”

  “There are only a handful of men I think worthy of you, Darc.”

  “That’s so sweet of you,” she says, and I know her cheeks are now that delicate pink shade they get when she’s embarrassed.

  “It’s the truth,” I tell her and forge ahead and tell her the rest. “You’ve actually met this guy before. Though I didn’t remember until he told me he remembered you.”

  “I know him?” She asks with unmasked excitement.

  “Yes,” I say, and even though I love to tease her, I’m not going to about this. “Tate Maddox. You probably remember him as Tommy Maddox.”

  “Oh, my God,” she says, and I know she is aware of exactly who he is. “That’s the guy who walked away from that huge contract because he said all the money in the world wasn’t worth losing his soul over.”

  “Yes.”

  She squeals. Fucking squeals.

  For
the record, Darcy has never squealed. Ever. I hold the phone away from my ear in shock. When I put it back in place so I can hear what she’s saying, I rather wish I hadn’t.

  “Oh my God,” she repeats. “I was so floored by him and what he said and that he actually followed through. Do you know how rare that is? What does he do now? And I really met him once? How is it I don’t remember? When was it? And he remembers me? Really? What did he say about me? Tell me, Elliott. Tell me every single word of your conversation and don’t leave anything out.”

  Fuck my life.

  Chapter Five: Darcy

  “Don't look for a partner who is eye candy. Look for a partner who is soul food.” Karen Salmansohn

  I end my phone call with Elliott wearing a stupid grin. I’m still in shock he’s set me up with Tommy - Tate - I correct myself, Maddox. It never even occurred to me he could possibly be someone Elliott might pick. Not because I’m not interested, but because Tate has been out of the spotlight for so long. I hate to admit it, but to be honest, I forgot about him until Elliott said his name.

  I search his name from my computer at work and wonder how he’s changed since I last saw his picture. Most of what populates my screen are old news stories from when he turned down the eight figure contract New York offered him. I skip over those, hoping to find something more recent, but I take a few seconds to appreciate the images my search returns.

  The Golden Son, the news outlets delighted in calling him and even now as I look over the pictures from years ago, it’s easy to see why. The images highlight his all natural good looks - his sun kissed hair and deep blue eyes, paired with a heartwarming smile showing perfect white teeth. Wrap that together with the way he can hit a ball and how he always says ‘ma’am’ and ‘sir’, and you have every woman’s dream date who is also the dream son-in-law of both her mother and father.