The World of Cherry

Kay Brandt
7 mins read
Published over 2 years ago
Chapter 16

The World of Cherry (Chapter 16)

Chapter 16: Cougars and Wolves

Escorting a statuesque woman has a strange circus act quality for me. I am short, and there's no hiding it. I mean, short, like 5 foot even, as in 5 feet no inches to add. I used to pray at night for god to hear my wishes for wanting to be taller. Then came the time to accept my lack of altitude and own it. I'm comfortable messing around with girls of all sizes, but Devon is like a skyscraper to me at nearly 6 feet in heels. Am I walking her or is she walking me is the question, as I take her to a small room with a laptop, desk and chair. I've had a few rendezvous in here, usually a sneaky quickie, nothing substantial. “I'm going to stand outside the door while you fill out the application. Cool?” I tell Devon, handing her a file of paperwork.

“Why? I don't mind you being in here with me.” Devon opens the file, looking over what's inside.

“I appreciate it, but I want you to have privacy.”

“Even though you're going to strip me of it with these forms?”

“Sorry, it's just the way business is run. Most of the papers are questions to answer. Cherry likes to make sure your head is in the right place before joining.”

“I hope she's not expecting an essay on why I prefer pussy to cock.”

“Not an essay, rather an honest statement.” I'm almost out the door before being called back in.

“Do you have a pen? How about a drink from the bar?” Devon inquires.

“Here's a pen, and the drink will have to wait. It's best if you are sober, well, at least sober-ish, while filling out the papers.”

“Try 'far from'.” Devon is totally beyond her limits.

“I'll check on you in a few.”

Stepping out, I steal a few minutes of “me time,” checking out my possibly-soon-to-be girlfriend hanging by her ankles from silks. Besides height, I wanted flexibility, and I didn't get that either. I can hardly sit crisscross apple sauce, but man, Kristin can spread her legs, spinning and twisting, doing splits in the air. This show she gives feels like it's only for me. The strength she has to do aerial tricks is awesome. Cherry and I share the same fascination with dancers. Maybe it's because they offer something we will never have or be able to do? The art of acrobatics and chair and pole dancing is simply spellbinding. Kristin lowers her body down to hover over a table of members, letting them touch her like giddy schoolgirls, not wealthy society women. As she slowly rolls herself back up towards the aerial perch, a few pangs of neediness hit me. I wonder how I will keep my hands off of her tonight if she's not into it when we get home. Her performance transcends raw lust, and I can go with the situation of rubbing her sore muscles till she gently falls asleep on my bed. I've become a spooning champion, and many sleepless nights were sacrificed while earning the title. One thing I was blessed with is a clit big enough to resemble a small penis. If she falls asleep without panties, I might be able to penetrate her with the tip. I have a feeling she'll want more once I do.

Just then, I hear a thud from inside the room. I check it out to make sure Devon is okay. On the floor she lays, passed out cold, a large and empty flask loosely held in her hand. She may have hit her head on the way down, considering the tight quarters. I check her pulse and she's alive, just drunk. The girl got a little carried away on her first night at the club, which is common and forgivable. I can't put her in a car at this point, and I know she drove here with Winterlynn. I leave Devon where she lays for now, while I put together another plan. 

Cherry is deadly serious about no one leaving her club intoxicated if they are driving. Most members travel by chauffeured vehicles, and some prefer to have their affairs in them and not in a room at the club. The vehicles must be parked in our special zone behind the building, where we can keep the cars supervised and hidden from view as much as possible. When members have our girls in their possession, we insist on keeping them on our premises. The situation with Nixie tonight is different. Cherry owns the hotel where Marina is staying. When members invite out of town guests, we often suggest they stay at the hotel to ensure the affair happens smoothly, if it is to happen there. The other thing is we don't like chauffeurs to be in the cars while affairs are in full bloom and we have a nice waiting room for them to relax without having to witness the wild throes of female love making. As open as some might seem, very few can be mature about the sounds and sights of two women passionately taking each other. It can be overwhelming, to say the least, and those not partaking, unless invited to voyeur in, need to stay out.

Winterlynn is feeling no pain as well. Lindsey, a member who enjoys her spirits without limitations, has been feeding the new dancer a steady flow of drinks for the past hour. The situation was under control until Winterlynn took the dare of getting undressed at Lindsey's booth, which although understandable, was not prearranged or paid for, and freestyle nudity is strictly prohibited. It's not that the members would mind or complain, but when the performers get naked, or any employee for that matter, it must be done with Cherry's approval—not because a frisky lady got too playful and forgot proper etiquette. I wag my finger at Lindsey, reminding her that she's pushing her good times into trouble territory. She snorts out a laugh as Winterlynn babbles incoherently, being scooped off the floor by me. 

“Good job, Lindsey. What was the liquor?” I ask.

“I don't remember. Something sweet. Champagne, maybe?” Lindsey tries to stand, but it's not happening.

“Don't move. I'll be back to help you as soon as I get this one in a car.” I practically carry Winterlynn out to the parking lot. Putting her in Cherry's car is really my only option. I can't just leave the girl at a bus stop and we don't like calling taxis. When I say car, it's really a massive downgrade because Cherry's car is a luxury performance machine. I've begged to drive it, but Cherry is the only one allowed behind the wheel. Somehow I manage to get Winterlynn situated in the backseat. “Stay! Got it? I'll be right back with your girlfriend.”

Cherry sees me assisting Devon out, asking, “Where are you going with her? What happened?”

“Oh, you know, the usual routine for first timers. Winterlynn is already in your car.” 

“You're kidding? No, no no.”

“Sorry, boss, we have no other choice.” I don't wait for an answer. Cherry's hotel is booked full tonight. We do our best to keep the location of Cherry's home a secret, however we've run out of options. Schlepping six feet of legs and hair out back is a massive struggle with no way of being graceful. Cherry follows behind me, catching a flash of Nixie and Marina leaving together as well.

“Oh look, Dusty, Nixie is on top of things as usual.” Cherry waves to a few members as we exit, and then double checks, “Did you get Viviana with Avery?”

“Of course, of course. The situation has probably caught fire by now, just like my back.” I stagger towards Cherry's car. The Boss Lady is kind enough to help me out, getting Devon in the car next to Winterlynn.

“You got this?” I never assume Cherry isn't constantly in need of my assistance. Better to be on high alert at all times than to be seen as slacking off. Slackers do not live long in Cherry's realm.

“Sure. Please call the house and have a room set up and ready for them.” Cherry's being a good sport but I can tell the drunk chicks are like bad children to her right now. She had a much simpler plan in mind—a beeline from car to house to bedroom to naked time with hot lover keeping her bed warm. I was in full support of her plan, and mine, until it had to be altered. Such is life and the perils of working with newbie club party girls.

“Be safe,” I tell her, closing her car door and watching them drive off. Immediately I make a call to Sandra, the housekeeper, who's been working for Cherry longer than I have. “Sandra, sorry to call so late. Cherish is on her way home with two girls in tow. No, put them in their own room. They're strays.”

It's still fairly early, just fifteen minutes after midnight. Time to check on the performance schedule. I have to stay until the club closes and tonight it appears we will be open until 3 a.m., after the last affairs have come to a close and the members have reluctantly gone. We only have one day off before our next night at this location. I'm going to spend it putting all of my energy into being the perfect rebound girl for Kristin as soon as this night is done.

Viviana teeters on her platform heels as I lead her to Avery and Katherine's private room. We cross the dance floor and her body reacts to the sick beats, booty shaking side to side. “I want to dance,” she proclaims.

“Later. You've been assigned to Avery for the next hour.” I give the instructions for the second time.

“But, I want to dance.”

“Listen, Viv, all of Cherry's girls are thrown to the wolves eventually. You've been cocktailing for a few months and now your ticket has been bid upon. Come along, it's getting late and Avery is waiting.”

“Thrown to the wolves?” Viviana questions in her dazzlingly hot Hispanic accent. Not much between the ears but everything else is in ample supply. I'm thinking sending her on stage for a naked salsa cha-cha could be flipping insane, but then she says, “That doesn't sound pleasant,” and I wrap an understanding arm around her.

“I mean, never mind. You'll understand shortly.” 

It takes some effort, but I manage to get her dancing limbs past the stage to the other side of the club in one staggered swoop.