Weeks pass. Anna settles into her new roles both professionally and sexually. Her body adjusts to new experiences and new pleasures. Her mind adjusts to having her needs thought of and satisfied. She concerns herself less and less with her husband as she dives fully into the life of an on call slut, determined to satisfy all of her master’s desires.
One night she is at home. It’s late. She is in bed with her husband. Her phone vibrates. It’s him. He has never contacted her after business hours before, knowing her husband might see and ask questions. What could be so urgent that he would cross that line? Surely he can’t be expecting her to come service him at this time of night? Though the thought of sneaking out for a late night rendezvous excites Anna enough to get her wet and blushing.
Anna gets out of bed and leaves the room, hiding her phone as if it is something she shouldn’t have. When she is sure the coast is clear she reads. “Anna, be sure to wear something that can easily be removed tomorrow. Have a good night.”
So cryptic. Anna didn’t think she had worn anything that he couldn’t take off of her if he desired. But she know better than to ask questions. Just to follow orders. She texts back immediately, “Yes, sir. See you tomorrow”.
She returns to bed, going over every item in her wardrobe in her mind. She couldn’t look through the closet without raising suspicions. She drifts off to sleep thinking about what outfit could be easily removed while still looking professional.
In the morning she all but runs to her closet as soon as her husband has left the bedroom. She pulls out several options before deciding on a light blue wrap dress that accentuates her waist and has a good deep V to show her breasts well. A chunky white belt and a pair of black ankle boots complete the look. She hurries to the bathroom to shower, shave, do her hair and makeup, and continue wondering what he could possibly have I store for her. She doesn’t kiss her husband or even say goodbye as she leaves, too preoccupied with what might lie ahead.
As usual she arrives before he does and gets to work putting things in order for the day. He walks in nearly two hours late. Walking with him is a very tall, thin black man. The two of them are a model of contrast, the boss in his usual tailored black business suit, his beard shaped yet bushy, obscuring his neck. The stranger is draped in outlandish colors and patters, a carefully manicured goatee ringing his taught lips. Trailing behind them are half a dozen men carrying boxes, hanging racks, fabrics, and more.
“Good morning, Anna,” the boss stops at her desk and says with a smile. “I will be calling for you shortly.”
The crowd enters his office. Moments later the carriers come out empty handed. Each one of the five men tips their hat to her as they pass by. A half hour passes by. No call. Anna goes about her duties for the day.
Another half hour. Nothing. Last night’s cryptic message combined with today’s odd occurrences has her mind racing.
Finally his phone extension rings.
“Anna, please come in.”
As she enters and hears the now familiar click of the lock she see fabrics, measuring tapes, and clothing racks spread all over the office. Anna’s eyes go wide when sees the boss near his desk standing completely naked with his arms out and legs spread. The tall outlandishly dressed black man is on his knees taking measurements.
“Good morning again, Anna. This is Rod.” The man grabs the boss’s flaccid penis and says, “Looks more like a flop to me.” He lets go of it with a laugh and walks over to Anna, smiling. “But I’m Rod!”
He doesn’t hesitate and hugs her as if they were old friends. Then in one movement he lets her go he spins on his heel back to the boss and yells at him, “Did I tell you to move? Christ almighty, if you weren’t so rich and handsome…”
Anna stutters, “Yeah, hi… I’m Anna…” her reaction a beat behind the action.
Rod kneels before the nude man and goes back to measuring. He turns around and yells up at Anna, “Why are you still standing there? Get naked! Prepare to be fabulous!”
The boss rolls his eyes. “This is why I told you to wear something easy to take off.”
She looks at him with an eye brow raised and takes her belt off, starting to untie her dress and open it exposing her bra and her now normal lack of panties. She stands with her dress open, looking at Rod inquisitively. “What am I doing naked in my bosses office, Rod?”
“I’m getting fitted for my suit for an event next month. And you…” the boss says, before getting cut off.
“Are going to be a motherfucking princess, you silly bitch!” Rod yells.
The boss takes a breath and says, “You’re going to be my date for this event, Anna. So I flew my tailor, Rod, in to take your measurements and get to work on something for you as well.”
“And don’t even pretend you haven’t been naked in your boss’s office before,” Rod says, wiggling his eyebrows at her. “I’ve heard all about you, Miss Magic Mouth.”
A visible wave of embarrassment and shock comes over Anna and she starts to close her dress again.
“Frank Sinatra said a woman tells her hairdresser everything but a man tells his tailor,” the boss says with a chuckle and a shrug.
“Sinatra never said that. You just wanted to tell me you were getting historically incredible blowjobs,” Rod rattles. “Which you could have had all along if you just switched teams, Mr. Businessman…” Rod flutters his eyelashes at the boss.
“Nope. Still too big a fan of pussy for that, Rod.”
Rod pouts for a second. “Fine. You can have him. He’s a bit small for this queen anyway. But you, baby girl, still need to take your clothes off for me to be your fairy godmother and turn you into a princess. It sounds like he owes you.”
“What event, sir?” Anna says, trying to keep up with their rapid fire patter. “It can’t be the big charity event in L.A. is it? That’s a huge event for famous people, isn’t it?”
“No, not LA. Europe. It’s a private event. I thought it was about time you met some of our international clients,” he says as if jetting off to European galas was routine. “Would you like to go to Europe, Anna? All on the company dime, of course.”
Anna’s mouth drops open. “I… yes… of course,” she stammers.
Rod snaps her out of her daze by shouting, “Hey! You! Naked! Now! Don’t make me tell you again!”
Anna giggles and sighs, “I guess you’re right, Rod. Maybe he does owe me something nice I can wear out in public.”
She takes her dress off and folds it over his desk chair, unclasping her bra and letting her double D’s bounce slightly as she frees them. She stands, nervous and naked, waiting for her turn. She bites her lip as she sees her boss’s cock start to go rigid as he stares at her body.
“You need to put that away unless you brought enough for everybody!” Rod says, slapping the half hard cock.
The boss flinches. Anna can’t help but giggle. She has never seen anyone but her boss in his place before.
“I’m almost done here, Mr. Can’t Keep It In His Pants,” Rod snaps.
“I’m not wearing pants to keep it in,” the boss snipes back at him.
“Don’t you bring semantics into it, rich boy!” Rod snaps back as he stands. He is nearly 6 inches taller than the boss. “Now put a robe on or something. Your averageness down there is distracting.”
Rod turns to Anna. “Now you on the other hand, I will enjoy to no end! Look at you!” He walks over and stands next to her, putting his smooth hands on her bare skin.
“I am thinking we need something that shows off your yes yes’s,” he says, jiggling her breasts. “ And accentuates this uh huh,” he smacks her ass, “And makes every man in the room wish he was getting some of your mmmmmhm,” he slaps her pussy. “Does that sound about right?”
Anna goes into silent shock as he touches her body. She feels a little uncomfortable, not just because someone she has just met is touching her but also of what he is implying.
She stands silent and blushing. “Speak, princess! Don’t you die on me now!” Rod shouts, putting his ear to her chest, mock listening for a heartbeat.
Anna giggles and takes a deep breath before saying, “Rod, I don’t know what kind of women you have dressed for my boss before but I’d prefer to look classy and sexy rather than like a certified prostitute.”
“That’s more like it! Oh babygirl, we are going to make you look so sexy, ScarJo is gonna be a straight up jealous whore!” Rod squeals.
As he gathers his measuring tapes to begin measuring Anna he calls over his shoulder to the boss, ” Speaking of… Who pleases the meat better, international playboy? ScarJo or this one here?” He squeezes Anna’s thigh.
Anna concentrates on not letting her jaw drop again. She’s both afraid of the answer and shocked that someone who has been with Hollywood women has chosen her to be his personal and sexual assistant.
“You know, sometimes I regret telling you who I’ve been with, you old hag,” the boss mutters.
“Oh please. Your dick has seen more stars than Netflix. You loving dishing to me. Now answer the question,” Rod retorts, not missing a beat. Turning to Anna he says, “Arms up, legs out, honey. I’ll be gentle since it’s your first time.”
“I told you this one gives the best blowjob I’ve ever had. Period. No competition,” the boss answers back.
Anna blushes, unable to wrap her mind around what has just been said. “I doubt I’m the best he’s ever had Rod, he’s just saying that to make me feel good.”
“Oh honey he told me you were the best the first time you swallow his man pole,” Rod says. “He means it.” Rod clicks his tongue as he measures. “And how many blowjobs have you had, mister?”
“Fuck, I don’t know. I got my first one when I was 13. So twenty five years of head. You do the math,” the boss says, somewhat annoyed with this line of questioning.
“Only if I get to watch, you whore,” Rod claps. “Princess Magic Mouth, how do you want this thing to fit? Tight and sexy? Loose and flowing? Tell me what makes you feel like a fucking goddess!”
“I want to be able to move but I also want to feel like a million bucks. So not super tight, but not super loose, if that makes sense. I think floor length sounds stunning, but I’m not sure what the occasion is, black tie or cocktail attire?”
Rod nods and thinks then yells over his shoulder, “Who is the worst you’ve ever had? Who absolutely sucks at sucking?” He cackles.
The boss doesn’t even take time to think and tosses off casually, “None of the Kardashians can suck cock worth a damn. Kim is the worst. Khloe is a little better. Kylie is decent but not great. Their mother uses her fucking teeth.”
“Some days I don’t know how his cock hasn’t just fallen off,” Ray whispers to Anna, making her giggle. Then at full volume, “Because a bitch with money doesn’t need to suck dick!” He smiles wide, “Unless they’re me. I’m a rich bitch but I suck cock because I love it!” Then his face is all business. “Hm… Floor length. Deep neckline. Sleek. Classic. Royal blue. Silk and chiffon. Yes? Say yes. Say yes!”
Over his shoulder, “What’s your budget?”
“Six, eight, ten thousand?” the boss volleys back. “How about you just make it and I’ll just pay for it?”
“Music to my adorable gay ears!” Then back to Anna. “So… Yes? Yes, yes, yes!”
Anna speaks up, “Wait… Wait… Ten thousand dollars?!” She looks to her boss, “Sir. You don’t need to spend that on me. Seriously, I’m flattered, but I’ve never spent ten thousand on anything, let alone a dress that I’ll wear once.”
“Bitch, please!” Rod cuts her off, shaking his long index finger. “I have seen this man spend more than that on a coffee table.” Then he reaches out and bounces Anna’s tits with his hands. “And that didn’t have these inside of it.”
“Anna, it’s not a worry at all. As long as you are my assistant, Rod is your tailor as well,” the boss says calmly.
Rod plants an enthusiastic kiss on Anna’s lips. “Oh and I have so many ideas for you, my little love cake.”
“I’ll also be bringing in my jeweler later this week to accessorize you properly.”
“Jennifer? You’re bringing in Jennifer?!” Rod screams, his eyes popping.
The boss shoots him a look that tells him to be quiet. For the first time Anna has seen, Rod listens.
“This is the world I live in, Anna,” the boss says. “I’m bringing you into it after all you’ve done for me.”
“And all you’ve done for his little wiener,” Rod giggles.
Anna musters a quiet, “Thank you, sir.” Mentally she hopes she has done more for him than give “historically incredible blowjobs.”
Rod wraps a hug her again and she says, “I’m anxious to see what you have in store for me. Even if I’m not sure how to feel about the price tag.”
“You let Mr Fortune 500 worry about the price tag for this old hag,” he says. “I may have to find out what the best blowjob in the world feels like someday.”
Anna’s is unable to hide her shock this time.
“Yes, honey, I am as gay as a unicorn farting rainbows. But game recognizes game! If you know some tricks I don’t, I gotta know!” he giggles.
Anna looks over at her boss.
“If you want to suck Rod’s rod, you have my permission. But he can’t fuck you,” the boss chuckles.
“Honey, I don’t want any of that. Besides I’ve heard you’re not ready for the hole I’m used to,” he says sticking his tongue out at Anna.
“He may be a little bigger than you’re used to as well.”
“A little? A little bigger?” Rod says with a mock look of shock. In one swift move he drops his pants. “I may not know much about how y’all straight people fuck. But I know what a big dick looks like. It looks like this.” He points to his extensive length as he says it.
Anna’s eyes go wide. She’s never seen cock that big in person before.
“Don’t worry, babgirl. It doesn’t bite. It just spits,” he giggles again.
Anna covers her eyes in embarrassment and giggles. “Rod, I appreciate your enthusiasm, but I don’t know how I’d feel sucking the cock of my boss’s tailor right now. No offense, you are quite impressive, and I’m sure I could handle every bit of you… But …” she giggles again and blushes.
“Did you just say you could handle every bit of this?” He grabs his cock and points it at her. “I got a good mind to stick this chocolate love stick right down your throat!”
He looks at the boss.
“I’m not going to stop you. But you’d be better off letting her take control,” he says.
Rod fakes surprise again. “You dirty little pervert! You want her to do it so you can watch!
“I just want you to see I wasn’t lying about her skills.”
Rod clicks his tongue. Thinking. Considering. ”
Alright, babygirl. Show me what you got. If you’re as good as he says you are I’ll make the damn dress for free.”
Anna gulps and look at her boss. Is this really happening? Is he really letting someone else have her?
“Are you sure, sir?” she asks.
The boss nods.
“Rod? Do you really want me to do this?”
Rod nods.
Anna feels slightly set up. But also excited that someone thinks so much of her abilities to want to show her off. She sighs and accepts the challenge.
She gets on her knees in front of Rod and takes his cock in her hand and starts to jerk it slowly, adjusting to the size of it before flicking her tongue over his tip. She looks up at him to see how he reacts to her initial touch.
“Baby girl, I am a pro when it comes to making men cum. So don’t feel bad if you can’t get me there,” Rod giggles, clearly daring her not comforting her.
“Show him, Anna. Shut him up,” the boss calls encouragement.
That’s all Anna needed to hear.
She takes Rod’s shaft and lick his entire length, sucks on his balls, and jerks him faster before taking his shaft and pushing it into her mouth sucking just the top half, adjusting to his size slowly before gradually pushing him down her throat, gagging slightly. As he goes deeper she breathes through her nose deeply and lets drool run down her chin onto her tits. Eventually, she takes him completely in her throat before pulling her head off and saying to him, playfully, still jerking him, “You were saying?”
Before he can answer she pushes him down her throat again and fuck him with her throat quickly. He is so big she can tell she may have trouble speaking the rest of the day. But she has been challenged.
“Goddamn baby girl you do got some talent,” Rod says, slightly out of breath, his voice lower than before.
Out of the corner of her eye Anna sees the boss open his robe and start to jerk myself.
“I told you, you old queen,” the boss chuckles.
“You shut your mouth and let the girl work,” Rod snaps back before moaning loudly as Anna squeezes him with her throat.
She continues to fuck him with her throat, moaning slightly and run her fingernails up his thighs trying to increase stimulation. She reaches a hand up and massages his balls before pulling him out of her throat to suck on him, flicking her tongue over his shaft to give her mouth a break. She looks at her boss and winks, glad to know his enjoying watching her suck a big black cock just as much as Rod is loving her mouth, tongue, and throat
The boss continues stroking himself. He wants so badly to come up behind her and fuck that tight pussy. He has become more addicted to her than he would like to admit. But this is her chance to be the main attraction.
He can see Rod straining, trying to pretend he isn’t enjoying himself.
“Rod, just accept a good time. A mouth is a mouth, isn’t that what you always say?” he calls out.
“Didn’t I tell you to shut up, white boy?” Rod growls in a way that tells Anna that she has him. She knows what a growl like that means.
She looks up at Rod with tears running down her cheeks from his shaft in her throat. She pulls him out and strokes him with both hands, silently shocked that both hands fit with room to spare, and tries to get both of his balls into her mouth to suck on them. Releasing his balls, she keeps pumping his cock with both hands and sucks on his tip, moaning playfully and enjoying every minute of this.
“Rod I’ve never heard you this quiet before? Problem over there?” the boss chuckles.
“If you don’t shut your mouth I am going to make you finish what she started,” he growls again but in a higher pitch. He’s getting close.
The boss walks over, his cock sticking out from his robe. He smacks Anna’s ass. He couldn’t resist touching her any longer but didn’t want to interfere. Anna moans, shoves Rod back down her throat and reaches a hand up to her boss’s cock and starts to jerk you gently. She starts making more noise, moaning and gagging as the drool runs down her chin and finding she loves the feeling of pleasing two men at once. She hopes it pleases her boss to see how talented his little slut can be.
The boss pulls his cock away from her.
“Focus on sucking this man’s soul out,” he says patting Anna’s head. “You already know you’re getting this today.”
Anna smiles and moans at her boss’s reassurance and continues the task at hand.
He retakes his seat.
“Finish him!” the boss commands.
Anna giggles and fucks Rod with her throat faster than before, massaging his balls with both hands.
Rods body starts to jerk.
“Oh don’t you do it Roderick. Don’t you do it,” he mutters to himself.
He tries to pull out of her mouth but Anna pushes him back in. Her boss demanded she finish him. She will not be denied.
“Oh no no no no,” Rod says, his skinny body jerking faster.
“Oh goddamn it!” he yells before exploding into her mouth. He may be bigger but Anna notices immediately that he doesn’t cum as hard or as much as her boss does. She swallows every drop.
“Did I lie?” the boss chuckles.
“You did not lie. Goddamn,” Rod says, trying to catch his breath. “Baby girl, if you ever grow a dick, I’m gonna marry your ass.”
The boss walks over and helps Anna to her feet and displaying your body like it’s his prized possession. “If you try to voodoo change any part of this, I may have to kill you, my friend. It’s already perfect.”
Rod mock pouts. “Alright, baby girl. You are going to look spectacular for Europe. And I ain’t even gonna get paid. Because if I let you do that again, they gonna take my gay card away.”
Anna laughs. “Rod, you said it yourself, game respects game. I’m just glad I could prove you wrong. Saving him some money makes it even better.” Her voice is hoarse from the intense abuse she just put it through.
She wraps her arms around her boss’s neck and kisses his cheek sweetly, feeling his rough hand grab her ass and playfully squeeze.
“Oh my god don’t make it worse by being all cute with this guy!” Rod screeches.
He reaches into one of his bags and pulls out a small bottle of mouthwash.
“Baby girl, put your clothes on and go use this.”
He pulls his pants back on and starts collecting his things.
“I have got to go do so many gay things. Reorient myself. Goddamn baby girl, you’re gonna ruin me!”
“Suit and dress will be ready when?” the boss inquires.
“When I goddamn tell you they are ready!” Rod yells. “Don’t rush my art! When you met me you were still buying suits at the mall! I made you!”
He comes close to use and puts a hand to Ann’s face. “Don’t you worry, baby girl. I will have you ready in plenty of time to give all of Europe a boner.”
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Source: reddit.com/r/eroticliterature/comments/gc4w8t/the_pleasure_of_business_an_erotic_novel_chapter