Brielle

 

Nice, normal girls don’t do things like this. They don’t hire a man for sex lessons to help them seduce their crush. What’s wrong with me?

I take another sip of chardonnay and give myself a mental slap on the ass. Game face, Brie. Kirby and I would be perfect together, and I know it.

I narrow my eyes at the online ad I came across when browsing the dating sites. It’s titled “The Gentleman Mentor,” but it’s the ad itself that has my heart kicking up speed.

 

Fit, masculine, educated male, late 20s. Discreet and forthcoming.

Under my direction and guidance, women learn seduction techniques, how to achieve climax with and without a partner, explore physical gratification, and more.

Dominant, but don’t be scared, kitten, I’m not into pain.

Do not be misled. I am pure mischief. But I’m the best kind of trouble.

So, what do you say? Do you feel like being naughty?

If you’re ready to reach new levels of pleasure, contact me at @thedominantgentleman. Serious inquiries only.

 

My pulse pounds in my ears as my cursor hovers over the message link, willing me to do something. Taunting me, mocking me.

I don’t know why this is so hard for me. It’s a simple message sent from the safety of my own home. I can just throw caution to the wind. If he’s a creep or an asshole, which he probably is, I can delete the message and pretend this never happened. And move on with my all-too-depressing life. Oh, joy.

I decided to take action after my last date from hell. I’m the poster child for bad first dates. You name it; I’ve lived it. From online dating disasters where the man who showed up wasn’t the guy in the photo, but instead someone’s grandfather, to a man whose wife crashed our date and threw a drink in my face. It was a coffee drink too, and freaking hot.

I’m tired of all the games. Especially since Kirby and I would be perfect together, if he’d just get his head out of his ass. After my last bad date, I met up with Kirby for a cocktail since he’s my best guy friend. He listened while I complained about men, supplying me with chocolate martinis and his comforting presence.

My take-no-prisoners attitude was born when Kirby, who I’d been secretly in love with for the better part of five years, looked at me solemnly and told me, “Someday I’m going to need to find a good girl like you, Brie, and settle down once and for all.”

I wanted to scream, I’m right here!

Instead, I nodded and mumbled, “Uh-huh.”

Which leads me to tonight. I created a generic profile specifically for this purpose. Fittingly, I’m Bookworm92.

 

Dear Gentleman Mentor,

 

As I type the first line, I realize I haven’t felt this alive in months. There’s something exciting and taboo about this, and apparently that gets my blood pumping. My fingers fly across the keyboard, typing quickly, before I can change my mind. It’s like they know something I don’t.

 

I am responding to your ad for lessons in seduction. I’d like your help in attracting a man. A little bit about me—I’m twenty-six, currently single, and I work as a real estate agent. I enjoy reading, yoga, and baking. I guess I’m just a regular girl who needs some extra help. I’ve never been good at the whole dating thing.

—Potential Client

 

With my heart pounding out of my chest, my finger hovers over the Send button. My mouth is bone dry, and my pulse is rioting in my throat. I know this is a big moment, but I can’t explain why. I click Send and take a deep gulp of air.

Leaning against the mountain of pillows piled at my headboard, I allow myself to daydream a little. What if this actually works? I picture myself with Kirby and a fond smile dances on my lips. The advice from my friends is to move on, to find another man who is as passionate about me as I am about him. But the thing is, I’ve tried. I’ve been on forty-three first dates and only three second dates. My track record is awful.

How do you even know if you’re dating, anyway? It’s all texting and meeting up for drinks on neutral ground and then waiting, hoping he’ll call. It’s casual sex and drunken hookups that you hope lead to more. It’s online dating profiles where you try to be witty and charming, and irresistibly sexy and cute. Achieving that perfect combination of girl-next-door and bombshell.

And it’s exhausting. I’m not any good at it. I’ve never been aggressive or flirty, or even very good at making conversation. I’m boring. A bookworm. A dedicated and loyal friend and employee. This is why I need help.

His help.

I glance at my e-mail again and almost shriek when I see his response. I sit up straighter and adjust my laptop screen.

 

Bookworm92,

Your e-mail bored me to tears. No wonder you need help attracting a man. Tell me about yourself. Hold nothing back. I’m a busy and demanding man. Dig deep. Why are you really single, and what do you need me for? Make me believe it, and I will give you the same candor.

—X

 

What a prick. I’m about to delete his e-mail and forget the entire failed experiment when a little voice whispers inside me, He’s right. My e-mail was boring and surface level. It didn’t tell him anything about me, or why he should work with me, if he’s as busy as his e-mail suggests he is.

I go to my kitchen, pour a shot of vodka, and down it in a single fiery gulp. Damn, that burns. I’m not some weak woman who doesn’t know what she wants. I let the fire fuel me.

Feeling determined, I return to my bedroom, set my laptop across my legs, and type out a response.

 

Gentleman Mentor,

I’ve had two sexual partners. Both were long-term relationships. One in college, one after. Jake had a small dick and Drew was decently sized, but didn’t know what to do with it. So I guess you could say my sexual experience is lacking.

I’m height and weight proportionate, and have played sports most of my life, but my small breasts and trim frame make me self-conscious. I’m never going to be described as voluptuous or womanly. I’ve been told I’m pretty, but I’ve never felt sexy.

There is a man I’m interested in, a male friend of mine who I’ve known for five years. I’ve had a crush on him all that time, but I’ve never acted on it. Pathetic, huh? But I guess I’m old-fashioned in that I believe a man should make the first move.

I’ve decided to contact you as a last-ditch effort. It’s time for me to let my feelings be known and pursue him, or move on for good. Five years is a long time, and I don’t want to waste any more of my life. And, if I’m being honest, the idea of a sexual mentor, a man who knows what he’s doing, excites me. Let’s just say, I could use the help. It would be reassuring to pursue a man and actually feel like I know what I’m doing when we got between the sheets.

Is that honest enough for you? Your turn…

—Bookworm92

 

His reply comes almost immediately, and I hold my breath while I read it, somehow hoping I’ve pleased him.

 

Bookworm92,

Much better, my little bookworm. Your body type is one coveted by many men. You’re called a spinner. A petite girl who can be sat down on my cock and used to my liking. You should never feel self-conscious about that.

I think I could help you with a few things, the first of which is self-confidence. Tell me what you want. It is only through open communication and trust that I can take you there.

—X

 

A warm shudder passes through me. His message is so blunt, it’s almost arrogant. But my body’s response is even more intriguing. I’ve never had a man be quite so direct with me before, and I’m intrigued and slightly frustrated. I have no idea what comes next, but I want to find out.

 

Gentleman Mentor,

I have no idea how this works, and I feel crazy for even considering it. But I need your help. I want to be better at all of this, attracting someone, the whole dating thing, and sex.

So, what happens now?

—Bookworm92

P.S. I noticed your ad said that you’re a Dominant, and while I don’t know much about it, it does make me a little nervous. Plus, I’m not a submissive, so…?

 

A small ding signals his quick reply.

 

Bookworm92,

You’re not crazy. I applaud you for taking the first step in contacting me. It shows me how dedicated you are. You’re demonstrating your willingness to learn and in turn, proving your dedication to succeeding. I’m not looking for a weekend fuck. I can get that at any corner bar. I take my work seriously, and I would expect you to do the same.

Regarding my dominant nature—when you hire me to be your mentor, I am in charge. I decide your lessons, your rewards, and your punishments. There will be no negotiation, which is why it’s very important that I learn your goals, fears, desires, and hard limits.

It takes an incredible amount of courage to submit, and I’m aware that you’re putting your faith in me. Despite how direct all this may seem, I live up to the word “gentleman” in my e-mail. You will be safe with me and treated with firm respect.

However, your boundaries will be pushed, limits tested, and the woman who emerges will know more about who she is and what she can offer a partner. You may not think you are a submissive, but contacting me for help is quite telling, yes? You’re willing to put yourself aside and let me take the lead. That’s good enough for me.

I’ve done this many times, and I can likely anticipate what some of your questions might be. We can cover those at our first session.

The next step is to meet in person and make sure this will work for us both. In the meantime, tell me one thing you’re scared of—what you think is holding you back. And also your schedule. I’m fairly open next week—I’m free on both Thursday evening and Sunday afternoon.

Speak soon,

—X

 

I stare blankly at his response. While I appreciate his lengthy e-mail—which helps me understand a lot more, both about this process and him being a Dom—doubt creeps into my mind. I have only a general idea of BDSM, and it’s not something I’ve ever felt the urge to explore. Honestly, I don’t know if I can do this.

I read his words again. He’s going to explore and learn my deepest fears and desires. He’s asking too much and I don’t even know him, so how can I be expected to share these most intimate parts of me?

A bubble of laughter rises up my throat at the irony. I’ll be sharing a lot more of my intimate parts with him if I pursue this.

I close my computer and pace my bedroom, realizing I’m stressed out and I haven’t even met the guy yet. Pulling a deep breath into my lungs, I decide I’ll sleep on it. I’ll wait a day or two to respond, give myself time to think about this. Having made that one small decision, I immediately feel better.

I head into the bathroom. Turning the faucet to hot, I let the tub fill. Sinking down into water that’s almost too warm, I sigh deeply. With my eyes closed and my body in a state of relaxation, I let my mind wander.

Almost immediately, I picture Kirby. With his broad shoulders, messy blond hair, and striking blue eyes, he is my warmth. My comfort blanket. He has been for a long time. He’s been a constant in my life, the man who has supported me emotionally through many ups and downs, loaning me money after graduation when the real estate market dropped, helping me move into my first apartment, and sending me my favorite flowers—peonies—on my birthday every year.

With a newfound sense of purpose, I rise from the tub, suddenly feeling silly for questioning myself. I don’t want to miss my only shot at getting actual help. This arrangement with the Gentleman Mentor—whoever he is—may be unconventional, but it might be just the thing I need to help move me from friend zone to girlfriend material where Kirby is concerned. And I’d be lying if I didn’t admit that e-mailing back and forth with my mentor has me feeling intrigued and slightly turned on.

Tossing on my cotton robe, I head for my laptop and open my e-mail. Glancing at his last message, I recall that he’s asked what I’m most scared of, along with my schedule. I fidget for a few minutes before typing out a hasty response, leaving out the part I don’t know how to answer.

 

Gentleman Mentor,

I would prefer to meet on Thursday. I’m supposed to go to my parents’ house on Sunday, and if I have to miss it, I don’t want my mom asking why. ;)

But can I ask you something? Has a woman ever backed out after meeting you in person?

—Bookworm92

 

Bookworm92,

Thursday would be fine. And no, a woman has never backed out after meeting me.

—X

 

I read his message with a growing sense of comfort. That’s good to know. Perhaps it’s simple curiosity because I have no idea what he looks like, but I’m afraid that he’s unattractive. I haven’t seen a picture after all. I know it’s terribly shallow, but I couldn’t go through with it if I’m not attracted to him.

Another thought flits through my brain and my nerves are back. My next e-mail flies from my fingers.

 

Have you ever refused services after meeting a woman?

 

His reply comes right away.

 

Bookworm92,

Yes, twice.

—X

 

I read his message and worry that he could refuse me if he doesn’t like what he sees. It’s not a comforting thought. I chew on my lip, unsure what to write back next when another message comes through. It’s as if he knows I’m hesitating and takes the decision from my hands.

 

Bookworm92,

We will meet Thursday at 8 p.m. at the Dakota. You will order one drink and wait for me at the bar. Dress in all black, wear something sexy, and underneath, your panties and bra will be red.

—X