The Gentleman Mentor(2)
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.