The Gentleman Mentor

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by Kendall Ryan


  “Not so much time together that, what?” I ask.

  “I don’t like to do more sessions than that because women tend to get attached to me.”

  I laugh despite his serious expression. There’s no way I’ll get attached to him. I’m still trying to wrap my head around how being with a Dom will work, even for this short period, and have no interest in pursuing that lifestyle long term.

  “You can take some time to think about it. I know for some it’s expensive—”

  “I want to do it,” I blurt.

  “Okay then. I’ll e-mail you the nondisclosure documents, a few local clinics that offer STD testing, and the pricing sheet for my services.”

  “I understand.” Nothing worthwhile is free, and I’m prepared to pay for his help. I can tell in our one short conversation that he is the real deal. As nice as it is to have a savings account, the money is doing me no good just sitting there. This is about me taking charge of my life and going after what I want. And right now, I want this unabashed man to teach me what he knows.

  “I want you to make a list of all the sexual things you’ve wanted to try, but never been brave enough to ask for.”

  “I—okay.” The idea of the task makes me a little uncomfortable, but maybe that’s the idea. I’m here to grow. To learn.

  “We need to delve into your past. Specifically, have you ever pleasured yourself? If so, how, when, the frequency, et cetera. I will need you to describe in detail a couple of fantasies. I want to understand your wants and desires, Brielle. It’s the only way I can help you.”

  I take a deep breath. I understand now, watching him, he doesn’t just want inside my body, he wants inside my head. It’s a big leap of faith on my part.

  “All right,” I whisper.

  He leans closer, his mouth twitching with a smile. “Do you touch yourself?”

  My breath lodges in my throat. He wants me to answer now? I thought he meant later—through the anonymity of e-mail. “S-sometimes.”

  “With a toy or with your fingers in your pussy?” He leans closer, close enough that I can smell his expensive cologne.

  I had a toy, but it broke from overuse. Somehow, I’m sure that would only make him laugh. “With my fingers,” I whisper.

  He reaches across the table and lifts my hand, studying it. Soulful jazz floats through the air, creating a sexy atmospheric pressure all around us as the gorgeous singer’s voice flirts with us from across the room. Hot and bothered in a way I’ve never experienced, I realize I’m flushed and warm from head to toe.

  “You have small, delicate fingers.” His finger glides along my index and middle fingers, inspecting me and tickling my skin with his light touch. “It will feel much different when I fuck you with my hand, but you’ll tell me everything you like and how to make you come. Won’t you, Brielle?”

  I swallow. “Yes.” My voice is a tiny whisper, and I know my cheeks are bright red.

  “And what about limits? Is there anything you’d rather not try?”

  He’s right; I have to take control of my life, my sex life included, if I want to succeed. I’m determined to be confident in this exchange.

  My eyes meet his. “Oral sex.”

  He makes a small sound of surprise in his throat. “Tell me why.”

  “My gag reflex—” I stop myself. I don’t want to sound like an idiot to someone who’s obviously much more sexually experienced than me. I don’t want him to know that I gagged and sputtered like an idiot the first and last time I tried it. “It’s just not something I enjoy.”

  He leans close, his voice dropping low, and his entire presence dominates every inch of my personal space. My inner muscles clench.

  “I can teach you how to suck cock like a fucking pro. How to deep-throat so well that no man will ever leave your bed. Would you like that, Brielle, my cock buried deep in your throat while my voice coaches you through? My thick shaft pumping in and out of your mouth while my hands massage your throat until you relax and take me?”

  Between my thighs grows damp, and I drop my gaze from his to the table. It’s too intense between us. God, we’ve only just met. Surely he understands I can’t go from zero to dirty talk in thirty minutes? The best I can do is to mumble unintelligible replies.

  I nod. “I could try, if you wanted me to.”

  His mouth curls into a devilish grin. “Are you wet, peach?” he asks, out of the blue.

  Dear God, it’s like this man can read my mind. I need a better poker face if I hope to survive my encounters with him.

  As I look down, averting my eyes, I hear him chuckle softly. My reticence is the only answer he needs.

  Chapter Five

  Hale

  Her responses have all been perfect in their delicate submission. The slight dip of her chin, the lowering of her eyes, the pink flush of her cheeks at my vulgar language. Things are going better than anticipated, and I’m a happy man at the moment, though my expression remains cool and neutral, so as not to give anything away.

  I pushed her to make a decision, told her that I had droves of women waiting in line, which is true, but I’d clear my schedule in a heartbeat for the chance to work with her. There’s something about her that draws me in, makes me want a taste of the sweet submission she has buried away.

  “Aren’t you going to order a drink?” she asks, noting the plain water in front of me.

  I rarely drink alcohol; I don’t like to give up control. But this beautiful creature before me doesn’t need to know such a personal detail. “I’m fine. Is there anything else you want to know?”

  She nods, and a little crease appears between her brows while she thinks about what to ask me. “Why do you do this? This mentoring thing?”

  “You want to know if I’m a normal guy and what I get out of this, right?”

  She nods. “Yes, basically.”

  I tilt my head to the side, considering her quizzical look. “Trust me, it’s a question I get often. I understand.”

  I take a moment, glancing around at our surroundings before responding. Even for men not involved in the lifestyle, I’ve found that by and large, men are attracted to women who are able to submit. Not weak, timid women without opinions and original thought. No, we want a strong woman who can match our wit, intellect, and stamina in and out of the bedroom. A woman who is confident enough in herself and her sexuality that she’s not afraid to leave her ego at the door and let me push all her boundaries. A woman who will drop to her knees at my command and trust me to handle every detail. I find that sexy as fuck. And that’s what I aim to teach the women I mentor.

  “I have a high-powered, stressful corporate job. I found BDSM a few years ago, and it felt like home.” I won’t tell her about the personal tragedy that led me there. “Many Doms have a single sub—a partner to explore this lifestyle with, and since I haven’t found that one right fit yet, this is my way of staying active in the community. And, honestly, I enjoy teaching. It’s very gratifying to me to see a woman reach her potential, to watch her let go of all her insecurities and blossom under my guidance.”

  Brielle looks at me with a sort of awe. “That’s beautiful, actually,” she says, surprising the shit out of me. I’m no saint; I teach women how to fuck like porn stars for my own personal benefit, as well as their own, but I nod at the compliment.

  “Tell me something about this man you want to win over.”

  A smile transforms her face, and she lets out a happy little sigh. “Kirby is…” She slaps a hand over her mouth. “Sorry. No names. He’s been my best guy friend for about five years now. We met in college and have always been just friends. He’s sweet and thoughtful and kind, everything I want in a man.”

  “What does he do? Professional-type job, or something with his hands?”

  She stifles a laugh. “Kirby? Do something with his hands? God, no. He’s a lawyer.”

  Feeling nauseated, I nod. “Got it.” I don’t need to know much about her Prince Charming, only that he’s male and
straight. After I’m done with her, the dickhead won’t be able to resist her.

  “You said you’d be able to anticipate questions I might have.”

  I nod.

  “I want to see how good you are.” She smirks as if she’s waiting for me to enlighten her.

  “I’m the best. Don’t doubt that for a second.”

  She chews on her lip and lets the silence engulf us before continuing.

  Watching her, I realize there’s something I’m enjoying about her reactions, and there’s no reason to rush this. I’ll just be heading home alone to an empty house after, or perhaps stopping and paying a visit to Chrissy if I’m in the mood.

  “You’ve been wondering what type of women generally come to me for help.”

  She smirks. “Yes, actually.”

  I nod. I told you I’m the fucking best.

  “They’re regular women. Your girlfriends, coworkers, and acquaintances. They are women who never reached orgasm. Women whose partner has strayed, and they want to learn how to satisfy their man, women who want to take control of their lives.”

  She nods along as I speak, seemingly enchanted by my words. Although there have been a few times when a woman has requested my help in winning over a man she already knows, like Brielle, I don’t tell her that. I’ve never seen this scenario successfully play out. If a man hasn’t taken notice, there’s a reason. There is truth in that old saying, “He’s just not that into you.” If he were, you wouldn’t be in my bed.

  But I won’t burst her pretty little bubble today. Because something tells me it would be fun to see her ride my dick and learn to be the seductress I see lurking inside her.

  Chapter Six

  Brielle

  I’m lost in his eyes, in his deep, watchful stare, wondering what will happen next. He’s in no hurry to rush our first meeting, and I appreciate that. This is all so new for me; I want to soak up every detail.

  “Did you do what I asked?” His voice is soft and controlled. It’s the kind of voice that washes over you, making you feel warm and desirable. I could listen to him speak for hours.

  “What do you mean?” My heart begins to hammer as if it knows something I don’t.

  He leans in closer, and my pulse pounds in my ears as he draws near. His gaze never wavers. Never strays from mine. Being in his presence is overwhelming. He’s so strong and sure, as I suppose a Dom is, but I had no idea it would feel like this.

  My body heats up, growing warm for him. He hasn’t even touched me, hasn’t spoken a single word. He simply studies me from across the table, and it’s as if he owns me. He could do anything he wanted, and I’d mold to his wishes.

  His eyes remain on mine, and though my natural response is to look away, I don’t. This is a test, and one that I very much want to pass. It’s as though he can read me with a single look. Those warm, mocha-colored eyes just dismantled me like a bomb.

  “Your panties,” he says coolly after several minutes. “Go into the bathroom and take them off. Place them into your purse and bring them to me.”

  Say what now?

  In his e-mail he asked me to wear red panties, and it was a point I fought with myself over. I didn’t own a red panty-and-bra set. And I knew he’d never see them anyway—this being the first time we’ve met, and my general sense of modesty. So why, for the love of God, I rushed out to Victoria’s Secret at the last minute last night and bought a red G-string and push-up bra, I can’t explain. Maybe my subconscious anticipated this moment.

  “I can’t just go take off my panties in a public restroom.” I meet his icy stare with an incredulous look of my own.

  He raises his chin. “The choice is yours. I need to know you’re dedicated to this. To me.”

  This is apparently my first test. And my stupid type-A personality not only wants to pass, I want to ace it.

  I rise from the table on shaky legs. He watches me while I lift my purse from the seat beside me and exit the booth. I feel wicked and dangerous, and suppress a naughty giggle at the thought. I like this side of me that so rarely comes out to play. This feeling could become addictive.

  When I enter the ladies’ room, I glance into the mirror to see a smirk slashed across my face. My cheeks are stained with two splotches of pink, and there’s a mischievous glint in my eyes. We’ve hardly begun working together, and I feel like a different woman already. Funny how taking control of your life will do that to you.

  Alone in the bathroom, I slip into the first stall and latch the door behind me. A moment later, the outer door opens and two sets of high-heeled shoes click across the tile floor.

  “Did you see who that was? He was sitting with a woman, but now he’s alone,” a woman’s voice says.

  “How could I miss him? Six foot three of sexy with a bedroom stare powerful enough to knock you up from across the room,” the second woman answers, and they share a wave of polite laughter.

  I can’t explain how I know, but I’m sure they’re talking about my date. With my skirt bunched up around my hips, I wait and listen.

  “It’s good to see him out. That was so sad what happened to him.”

  “It was devastating,” the second woman agrees.

  The water from the faucet drowns out their voices and I can’t make out their words, but I’m trembling. They implied that something tragic happened to him, and now that I think about it, there has to be more to his story.

  He’s a handsome, successful bachelor. Why is he single? Why does he do this?

  Unease churns inside me. I’m not sure if it’s wise to get involved in something I don’t understand. But what choice do I have? The thought of returning to my lonely single existence sounds miserable. Tonight is the most successful date I’ve had in a long time. Sure, it’s probably just because I’m paying him, but still, I feel different. Calmer, more graceful, in control.

  When the women exit the bathroom, I force myself back into the present. There’s no way I’m giving up now. I need to see what happens next. I push my fingers into the strings at my hips and slide the panties down my thighs. Depositing the tiny scrap of red lace into my purse, I exit the restroom with my shoulders squared.

  In my absence, the waitress has removed my salad plate and our glasses, and left the check. I slide back into my spot in the booth, sitting directly across from him. His mouth twitches with a smile as if he wants to ask me how it went, but he remains ever silent and watchful. It’s as if he knows I’m moments away from handing over the evidence, and doesn’t need to fill the silence with senseless chatter. His confidence is addictive.

  I match his self-assured posture and reach inside my small black handbag, balling the panties in my fist. Swallowing a sudden blip of nerves, I reach across the table, extending my hand toward him. Discreetly, he reaches out and takes my offering, immediately moving his hand to his jacket pocket and placing them safely inside.

  He’s going to keep them? I figured this was an assessment, designed to make sure I could follow basic instructions. I didn’t imagine him pocketing my underwear to inspect later.

  Geez.

  “If there’s nothing else, I suppose we’re finished for tonight,” he says, watching me coolly.

  My head is clouded by what I overheard in the restroom and I’m desperate for answers. Unsure what else to do, I nod my consent.

  He stands and watches as I grab my purse and exit the booth. He insisted on paying the bill, which was generous, considering all he had was water, and I had cocktails as well as a meal.

  When we reach the front of the jazz club, he holds the door and I step out into the night. The crisp Chicago fall demands to be noticed, and I wrap my arms around myself, wondering why I hadn’t worn a coat.

  “Will you be okay getting home?” he asks.

  “I’ll be fine. I don’t live too far.” I hardly touched my second drink, and the buzz I had has worn off.

  Lifting my hand to his mouth, he presses a kiss to the back of it. The gesture is so unexpected, so intimate, th
at I flinch.

  His eyes flash on mine, noting my uneasiness. “I need you to be comfortable with me, Brielle,” he says in a low voice, his mouth still on my hand.

  I nod. “I know. This is just all so new to me.”

  “How long has it been since you’ve been intimate with a man?” he asks, studying me.

  I consider lying, because, damn, the truth is embarrassing. But he’s been honest with me in everything so far, at least I think he has, so I decide to treat him with the same courtesy. “Four years.”

  His throat works up and down, the only indication of his surprise. “I promise I will make it good for you. You have nothing to be scared of. We’ll decide on a safe word, and all play will stop when you use it. Do you understand?”

  “Yes.” I blink up at him, fighting off the shiver tickling my spine.

  “What else is bothering you?”

  His ability to read me like a book, despite us having just met, is staggering. “It’s just that I’m not used to a man paying me such focused attention, and you’re a very attractive man, and you said women have gotten attached to you, and I don’t want that to happen.”

  Oh God, I’m babbling. Someone shut me up! Was there truth serum in that second drink?

  His mouth draws into a tight line. “That would be a very bad idea.”

  I swallow and nod.

  He draws closer, and I can smell mint on his breath. “I know you think this is about Kirby, but this is about you. I’m going to help you become the woman you want to be. One that no man can resist.”

  He’s right. That’s what I want, regardless of what happens with Kirby. I’m tired of dating dickheads. I want a shot with a good guy, and if it’s not meant to be with Kirby, well, then at least the Gentleman Mentor will have taught me some new tricks for winning over my real Mr. Right. I deserve love, and I will work hard to make it happen.

  “You have to trust me. Trust in this process. It’s going to be fun, I promise.” He gives me a flirty wink and treats me to that dazzling white smile.

  Dizzy, I’m not sure how to respond.

 

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