The Venture Capitalist

by EnRose, LaVie

  She removes the first card from the deck and brings it back to me. “This card gives me permission to truss you up in whatever manner I see fit and suspend you over the wooden horse.”

  I go to the highboy and return with everything I’ll need to exact my punishment. In my hands are two metal nipple clamps, a length of chain, and a small metal lock.

  I snap another order. “Remove your bra.” Now she’s only wearing the garter belt, hose, and shoes. I approach her with the clamps.

  I cup her breasts roughly. “These are so perfect, I almost hate to clamp you.”

  She does not speak, and it’s good that she keeps quiet, because any speaking out of turn will just earn her another trip to the card pile. She flinches at the pinch of the tiny metal clamp.

  She remains quiet but her breathing becomes audible. When I clamp the other one, she’s ready so her reaction isn’t quite as noticeable.

  I attach the chain to the clamps and allow the small lock to dangle between them. The pull from the chain is extra torture, but she remains quiet throughout.

  I lead her to the horse, which is a wide, triangular wooden plank covered in soft black leather set sharp end up, mounted on a sawhorse-like support. I will suspend her until she is astride it. Then leave her to ride it while the suspension puts more and more weight on her genitals until her full body weight is on that tender area.

  I hand her a single die.

  “Roll it,” I say.

  Keisha shakes the die in her hand, the lock tugging on the clamps, causing her breasts to jiggle. She releases the die. It rolls slowly, teeters, and finally stops on three.

  “Three minutes it is,” I say. Keisha looks disappointed, as she should rightfully be. This contraption will hurt.

  I put the harness around her body then attach the intricate ropes and pulleys that hang from the ceiling. When she is airborne I lower her over the horse until she’s on her tiptoes astride it. I bend and attach each cuff at her ankle with a chain across the back of the wooden horse. Then I do the same with the cuffs at her wrists and extend her arms up high over her head.

  “Does this hurt?”

  “No, Sir.”

  “Is it uncomfortable?”

  “Yes, Sir.”

  “Good. Punishment isn’t meant to be pleasant.”

  I lower her until the cold leather rests between her legs. “What are your safewords, Keisha?”

  “Jungle and Fever,” she says.

  “Your three minutes begin now,” I say then I lower her onto the horse and rest her weight onto the horse edge, which is blunt only because of the leather that surrounds it. “You may not make any noise.”

  I circle around her keeping my eye on the second hand of my watch. “One minute.”

  The pressure on her genitalia and the pinching of her breasts is likely one protracted, connected pain by now. When I call two minutes, I’m sure she’s on the way to numbness. Her legs are likely prickling as if she’s being stung with tiny needles. Tears begin to run down her face.

  For an infinitesimal moment, I think of relenting, but then I glance at my watch again to prevent caving. “Thirty seconds.” I turn away from her and walk back over to the highboy, and return with creams and ointments for aftercare and lay them on the bed. Immediately, I go back to the pulley wheel and release her, slowly. I carry her to the bed where I sit cradling her in my arms.

  As her circulation is restored, her tender areas will hurt. Without a word, I apply some cream to her nipples and massage ointment onto her wrists and ankles. I go into the ensuite and return with a bowl of warm water and soft towels. I clean her face with the already damp towel and wipe away her tears and runny mascara. Then I take the other cloth, soak it in the clean warm water, wring it out, and lay it gently between her legs.

  “We’re done here,” I say, and Keisha is surprised, but does not protest.

  Later, we lay in my bed facing one another, eyes closed, but neither of us is asleep.

  “Why did you stop?” she musters the courage to ask.

  In the ambient light, I open my eyes to see she is looking at me now. “Because your punishment was complete,” I say.

  “But you didn’t do everything you said you would do.”

  “Is this a complaint?”

  “No. Just trying to understand.”

  “A wise Dom once told me you can see in your submissive’s eyes when she’s had enough. I want you to keep coming back, Keisha.”

  “And I want to keep coming back.”

  “Then, why didn’t you just show up at six?” All of this could’ve been avoided if she’d just kept to the letter of our agreement.

  She sighs. “I was upset because you threatened to find new backers for KSR.”

  “You were more upset about that than being told to fire Jorge?”

  “Well, both.”

  “I see.” I cup her cheek urging her face up to look into my eyes. “You know punishment is necessary when you’re willfully disobedient, right? I punished you for not showing up at our appointed time, not for refusing to fire Jorge.” Although I learned that she would sacrifice herself for her blood. Jorge was a lucky bastard. I will likely never have anyone who would do such a thing for me. I won’t ask her to fire anyone so close to her again, because I know now, she will fight me tooth and nail to save someone she loves.

  “Yes, and I should have begged your forgiveness for being late when I arrived, but my impending punishment was all I could think about.”

  “And I should have explained that when a punishment session is over and all is forgiven, it must be forgotten, too. It’s toxic to dwell on the negative.”

  “I’ll remember that.”

  I hope she will, because I don’t want her to hate me. Although punishment is necessary in D/s relationships, I need her to dwell more on the pleasure than the punishment aspect.

  We lay quiet another few seconds before she says, “Why do you think you prefer this arrangement over a more conventional relationship?”

  “My therapist says I view BDSM on some level as a defense against abandonment due to the loss of my mother when I was young. Apparently, intimacy and trust are too difficult for me because I have been too severely wounded, and BDSM serves as a conduit for intimacy on my terms. It’s very hard to build a mature relationship of mutual respect if you are so fucked up that you’re constantly on guard.”

  “I don’t want the clinical answer. I’d rather know how you feel.”

  I take my time crafting my response because I am tempted to tell her something I’ve never told another submissive.

  As the silence borders on awkward, I sigh. “I watched my father lose my mother to ovarian cancer. He’s a strong man, but Nathan and I saw him brought to his knees. I don’t want to care that much only to lose the person I care for most in the world.”

  “Tristan, life is full of pain, heartache, and loss. All those emotions are inevitable. We don’t get to choose what we experience. Whatever happens, we just have to endure and learn the lesson.”

  “I paid a psychiatrist a small fortune to tell me exactly what you just said, but even he couldn’t convince me to change my mind about the way I choose to conduct my personal entanglements.”

  She lifts her hand to her eyes and clears her throat. I hope to God she isn’t crying again. I simply cannot abide tears. They remind me too much of the loss of my mother.

  She speaks again. “You could have a balance—a compromise, can’t you?”

  “Some people do,” I say. “Nathan wants to but I never have. I don’t think I ever will. I know you want a committed relationship someday, and I won’t stand in your way when you decide to go.”

  “I’m not in any hurry. I have about five years to find Mr. Happily Ever After.”

  “Until then, you’re mine,” I say and take her into my arms and kiss her until she fumbles to get my pajama bottoms off.

  “Are you sure you’re not too sore?” I say, incredulous that she would want me after the pai
n I just put her through.

  “No, I just feel like I came down too hard on a bicycle seat. I’m good to go.”

  “Well then,” I say.

  Sex after a misunderstanding is always bitter sweet. I am feeling so magnanimous within short order I rescind the withheld orgasm mandate.

  CHAPTER SEVENTEEN

  Keisha and I begin again and settle into a semblance of routine. Through the week she stays at her place with Ms. Jameson, but on weekends my condo is her home. She’s managed to avoid any harsh punishments since the Jorge debacle. Before we know it, we’re six months into running KSR. I host the second quarterly meeting in the conference room at White Enterprises, Inc. headquarters.

  “Financial update, Ms. Jameson,” I say.

  Jada starts when I change things up and request her report first this time. However, she finesses a fine recovery and says, “We should surpass the break-even point in a few weeks. Payables however, will be up around the same time as the north side location is scheduled to open within a couple of weeks. If performance and our projections hold steady, we should be able to cut White Enterprises and the Nathan White Brand a check in nine months.”

  I skim the financial reports as she’s speaking, and it’s true. The figures do bear this out. “Thank you,” I say. “When it gets closer to that time, I’ll have Randall in Finance contact you with a preference for how we’d like to handle that.”

  “What? Are you going to insist we pay you in cash?” Jada laughs, as do Nathan and Keisha, but I don’t.

  “An infusion of profit without any corresponding expenditures to balance it could wreak havoc on my tax bracket, Ms. Jameson. DePaul has an exceptional accounting program. Your response is surprising.”

  “Just kidding,” Jada says, shaking her head.

  “You need to lighten up, brother,” Nathan says, punching me in the arm.

  I glare at him. Keisha takes my hand in a quiet show of support under the table. “Stop it, you guys. You know Tristan never jokes about money.”

  “Operations?” I say, gracing Keisha with the smile I don’t have for my brother and his harlot.

  “We’ve signed fourteen acts, to date,” Keisha says. “When the north side location is fully operational, we hope to sign fourteen additional acts. We’ll evaluate each of them for profitability and replace any who don’t perform within six months. We have a steady stream of downloads for KSRs clients, and there is now a new receivable line item in the form of royalties for yours truly via Princess Danai’s new album.”

  “Congratulations, Keisha,” Nathan says. “I’ve been listening to ‘Champion Lover’ before we hit the courts every game. We haven’t lost yet.”

  “Congratulations,” I say, squeezing Keisha’s hand.

  “Thank you, Nathan…Tristan,” she says, her cheeks turning rosy with that uncharacteristic shyness that hits her sometimes.

  I have to bust Nathan’s balls over his superstitions. “What are you going to listen to when you finally lose a game?”

  “Keisha’s next album,” he says, as if he was waiting for that question.

  Keisha holds both hands up. “Wait a minute, now. Who says I’m going to do an album. I’ve got my hands full managing all our acts and selling good music to the masses.”

  “You decide for yourself if you want to do it,” I say. “Don’t let Nathan’s superstitions drive anything.”

  “She wouldn’t do that anyway,” Jada says. “She doesn’t need any of us to help her decide what’s best for her.”

  “What are you implying, Ms. Jameson?” I pin her with my eyes.

  “Hey, hey,” Keisha says. “Please let’s not argue over something that is clearly not even a blip on my radar right now. If I were to ever do an album, it would be planned out more thoroughly than dropping something out there because I got a compliment on a few background vocals.”

  “Please continue your report,” I say.

  “Anyway, we are scheduled to go worldwide six months from now, which will be a year from the time we opened our doors.”

  “Will there be any brick and mortar stores involved, or just online presence?” I ask.

  “You know, we haven’t thought about that,” Keisha says.

  Jada raises her hand, sheepishly. “I have.”

  Keisha laughs, but I can tell she is just a bit blindsided by her friend’s revelation. “When were you going to tell me?”

  “Now,” Jada says with a shrug. “It was just me dreaming, and kicking the idea around with Nate one night.”

  “Were you high?” Keisha says. “Because we haven’t paid back the loans we took out to start the business here in Chicago, yet.”

  “Clearly, you partners need to have a conversation about strategic development,” I say. Then I have to take a jab at the smug Senator’s daughter. “Keisha and I never discuss KSR business outside of these meetings, or conference calls I have with the both of you. You would be wise to do the same, Ms. Jameson.”

  “Why don’t we all have another meeting in a couple of days to discuss options,” Nathan says.

  “That’s going to be a bit difficult,” I say. “Ms. Beale and I will be in Milan.”

  “What?” Keisha says.

  “Not only is your business six months old, but so is our partnership.”

  “Oh!” Keisha is still dumbfounded by my announcement.

  “I ran it by Ms. Jameson and Mr. Cisneros, who were willing to hold the fort down while you’re gone.”

  “Okay, then. I guess I’d better pack my bags,” Keisha says. “Thanks, roomie.”

  “You’re welcome,” Jada says with a smile. “Despite having to be subjected to your traveling companion, I’m happy you’re going to Milan. Bring me back a souvenir.”

  Unlike other trips I’ve taken with Ms. Beale for business, this one is longer and distinctly for pleasure. We check into a suite at the Hotel Principe Di Savoia Milano where every amenity one is able to afford is available to us.

  Something about being on vacation with Keisha puts me in a tranquil state. By day we behave as tourists. By night we brave the club scene. I take Keisha out to dinner and dancing—then we hit the fetish clubs.

  As we patronize these clubs I’ve visited with other submissives on more than one occasion, Keisha and I are given red-carpet treatment, she is such a hit with the owners. The manager of my favorite luxury fetish club called The White Whip, is so happy to see us, he rents me his best dungeon for the weekend for a song.

  Keisha and I share a night of intense role-play with her in her most daring bondage gear yet. She wears a black patent leather dickey and patent leather thigh-high boots that make her toned legs look fabulous.

  I’m not sure if it’s the atmosphere which has thoroughly loosened up her inhibitions, or the liquor I gave her permission to imbibe before we arrived, but she makes a bold decision.

  “I’m ready for you to pop my anal cherry tonight, Sir,” she says after a thorough cropping on the St. Andrews Cross.

  I grin wickedly. “Here and now?”

  “Yes, Sir.”

  “You do amaze me, Ms. Beale,” I say.

  I take her hand and lead her to ensuite in the rented dungeon. “Let’s get you prepped,” I say with unabashed glee.

  When we are both clean from our shared shower, we move on to the red satin bed in our rented dungeon. I insert a spreader bar between her legs, locking her ankles open. I prop a pillow underneath her hips, presenting her ass to me at just the right angle. Keisha trembles like your average virgin might in anticipation of her first time, and I massage her briefly to calm her.

  I work her over with my mouth and fingers until she is completely relaxed before I constrain her wrists with leather cuffs to the headboard posts. I am so hard doing all this to her, I want to skip ahead and claim her, but that would be a foolhardy move. I prep her backside more by kneeling behind her, opening her butt cheeks and licking her clean anus.

  Keisha gasps, enjoying the attention I lavish on this often
ignored erogenous zone. I then massage her buttocks and thighs while continuing to kiss her in this most intimate place. Finally, I insert two fingers into her sex, and a moan escapes her lips.

  I hiss with excitement “Yes! It’s going to feel even better than that, you just wait.”

  I get carried away and bite down on her left ass cheek, making her gasp again, this time in surprise. She keeps quiet like a good little submissive save the panting, as I continue stimulate her in concert—licking her ass, and massaging her G-spot with my fingers. When I feel the constrictions signaling her imminent orgasm, I stop.

  “You have no idea how much I like this ass of yours. I’m going to bite it several times tonight.”

  “Yes, Sir,” she says through another gasp.

  My submissive has truly spread her wings, because she’s mastering a brand of kink that was heretofore distasteful to her. I am honored to be the one to introduce her to this. I can tell she has groomed herself well before this experience, because when my tongue lances her sphincter, all I taste is Keisha.

  I stop again, not to torture, but to prepare her to receive me. I slather her with warmed lube, taking globs of it onto my fingers and inserting them inside her. As I push fingers slick with lube deep within her with one hand, I massage her back, bottom, and thighs with the other. I murmur words of encouragement as she opens up to me.

  “Good girl.”

  She squirms and moans, clutching the sheet with her fingers, since she can’t move her hands or feet in earnest. I remove my fingers and quickly replace them with a warm, lubed butt plug. It is roughly my size and fits snugly where I’m going to be very soon.

  I unbuckle her ankles from the spreader bar.

  “I’m going to flog you now, Ms. Beale.”

  She moves her legs in a restless motion.

  “I took your legs out of the bar for my purposes alone. Did I tell you to move?” I say with a stern voice.

  “Sorry, Sir.” Her apology is swift and profuse. As I’m sure she thought better of pulling a punishment card.

  “As I was saying, I’m going to flog you because like virginal vaginal intercourse, virginal anal intercourse can be painful if not executed properly. Endorphins from the flogging will negate pain. Cancel it out, so to speak.”