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.