The Boss Lady Part III-Rewrite

Author’s Note: This is a rewrite of a story that I wrote some time ago. It was my first multipart story, in fact so, before you start reading, there’s some things that I’d like for you to know. First, this story is not meant to be racist in any way. As you read, you will notice that there is some mention of color, but this story was not written with the intention to be derogatory towards either character when it comes to their race. This story, like all of my stories, serves to assuage certain stresses and anxieties within my life. It is fictitious closure for me. In this case, my boss, who is quite similar to Anita, is the topic of frustration that I’m fictionalizing. This story is not based on truth. It is merely a “what if” scenario. Please enjoy, comment, and vote. I’d love to hear your feedback! Thank you…

–NL

P.S. I do not yet know how this story ends, and for that, I apologize.

The Boss Lady: Part III
Jack looked down at Anita. She was completely covered in his cum. He watched as she scooped up his seed from her face and greedily lick it off of her fingers. She seemed to love the taste of his it. She moaned pleasantly as she cleaned her face off. She looked up into Jack’s eyes. He could still see desire in them. He could see that she was still not yet fully satisfied and that she desperately needed his cock in her tight cunt.

“Thank you for all of that cum sir! You taste so fucking good! I just might need you to give me some more later!” She said to him submissively.

“How long are you gonna keep up this submissive attitude towards me? Are you gonna be like this at work?” Jack chuckled.

“You’re out of your fucking mind white boy!” Anita was laughing as well, still cleaning cum off of her face. “I just might call you “white boy” though.”

“You wouldn’t dare!” Jack replied.

“Watch me, white boy!”

“So, what do we do now?” Jack asked, helping Anita get off of her knees. He pulled her into his arms and they kissed passionately; he could still taste his cum on her lips. Anita quickly pulled away, almost seeming to be uncomfortable now with the idea of kissing Jack.

“I don’t know about you, but I need a shower! I smell like your cum and my pussy juices,” she said, walking out of the room.

“You say it like it’s a bad thing! I kinda like the smell!” Jack yelled, following her out of the kitchen, and back upstairs.

Once they were both upstairs, and in the master bathroom, Anita turned on the water and stripped off her heels and stockings. Jack was still nude, so he hopped into the shower first. The water felt good on his sweaty skin. Anita quickly jumped in after him and they both washed the sweat, cum and pussy juices from their tired bodies. Jack watched Anita as she lazily rubbed a soapy loofah all over her cocoa-brown skin. He grabbed the loofah from her and began to wash her, taking his time to get every nook and cranny of her perfect body. She accepted his gesture of appreciation, and closed her eyes as she let her employee clean his cum off of her body.

“You know that you really don’t have to do that, and don’t expect me to do it to you,” Anita said, her defensive wall coming back up again.

“Why are you always like that? Why do you always become such a bitch when someone actually tries to help you?! Seriously, I want to know!” Jack threw the loofah onto the floor and turned her around to look her square in the eyes.

“I don’t fucking know! Anita shot back. I’m just not used to favors; especially from the people who work for me! And don’t think that I am going to be treating you differently now. You are still my employee and you will act accordingly at the office, and that means acting like none of this ever happened,” she said wagging her finger between the two of them. Anita picked up the loofah and finished washing herself off. She gave it to Jack when she was done, and he started to scrub himself down, but received no help from Anita. She got out of the shower, grabbed two towels from linen closet and threw one over the shower curtain for Jack. She dried herself off, and walked out of the bathroom. Jack finished washing and got out of the shower. He hurriedly dried himself off and followed her into the bedroom.

“I think that you should leave,” Anita said, turning around to look at Jack. The look on her face was a mixture of hurt, and guilt.

“What the fuck is your problem?” Jack asked, dumbfounded by her sudden change in attitude, and frustrated at how the night was turning out. “I thought we were having a good time and now all of a sudden you just want to throw me out! What have I done wrong?!”

“Please just go! I need to process what the fuck just happened! I just fucked someone that works for me!”

“We didn’t fuck!” Jack said in a light tone, trying to resurrect the situation. “We gave each other some really good head, but we did not fuck!”

“You know what I meant, smart ass! Please just go and let me think about this! I will see you at work on Monday, but for now please just go!”

“Fine,” Jack said, snatching up the clothes he had left on Anita’s bedroom floor and stormed down the stairs. He picked up and put on his slacks that were left at the door earlier, slammed the door leading into the garage as he walked out, and then got into his car and left. After he got on the road, he realized that he was still a little drunk, but he figured that he could probably make it home as his apartment was not too far from Anita’s home.

Jack was fuming mad by the time he unlocked his apartment door. ‘How could she use me like this,’ he asked himself. ‘And why in the hell was he not surprised?!’ That was the type of person she was. She used people to get what she wanted and when she got it, she discarded them like trash. ‘At least now I’m not just an employee to her,’ he said to himself, pulling a beer from his dinky little fridge. He popped the top and guzzled it down. ‘I’m an employee with a big dick.’ He chuckled and took a deep, relaxing breath. He was glad that he didn’t have to go to work the next morning. He didn’t want to see her face, and it was probably a good idea that he didn’t have to for these next two days.

Two Weeks Later

Work had been relatively uneventful since he and Anita had their first sexual encounter. The two of them had barely spoken to each other, but that was not unusual for them. He had had time to dissect the events of that night, and he was no longer angry with Anita. He had even reached the point where he was beginning to feel sorry for her. She was going through so much, and that night was just nothing more than a moment of weakness for her. It didn’t exactly make it ok but… There was nothing they could do to change it now.

“Jack, can you come into my office please?” Anita called to him from her office.

Jack got up and walked back to her office. He looked at Anita, and saw a look of hurt on her face, similar to the one he saw shortly before he left her house that night. Jack got the feeling that he was about to be sucked back into her little world, and he was tempted to just walk back to his desk and refuse to come into her office at all. But in spite of all that; in spite of all the emotion, and the frustration, and the bullshit that was going on between the two of them, he took a moment to just look at her, and she looked damn sexy. Today she was wearing a black pencil skirt with a crimson blouse that had only one button unbuttoned. Her legs were covered in sheer stockings, or pantyhose, and she was also wearing a pair of pumps that were the color of crimson. They were far more sensible than the five inch chunk heels she was wearing on the night of their encounter, Jack thought.

“What’s up?” Jack asked, trying to mask his anxiety, even though he knew that she could see right through him, and knew that he was freaking out a little.

“Jack… For one minute, please… Stop being so fucking paranoid! Not everything is about you,” she said. “I called you in her to tell you that my husband and I officially separated the night after we did what we did.” She looked down at the floor, keeping the sullen look on her face. “We are divorcing as soon as possible.” She grabbed a folder from her desktop and showed it to Jack. He opened it and flipped through the pages. Sure enough, the file contained papers indicating that the two were separating. She was claiming reason for separation as adultery, so there was a good chance that she was going to get the opportunity to take him to the proverbial cleaners.

“I’m sorry to hear that Anita… I am… And I’m not trying to be an asshole when I say this, but what do you want from me? I mean… The last time you and I “talked” about you and your husband’s problems, I ended up storming out of your house after the two of us engaged in one of the hottest sessions of oral sex, both giving and receiving, that I have ever experienced in my entire life. And since then, I’ve been worrying almost constantly that you’ve been trying to get me fired!”

Anita almost laughed out loud and said, “I’m not going to fire you Jack, or even try to get you fired, for that matter! I can’t! I would lose my job too because you’d probably drop the dime on me! The reason I called you back here was because I need a favor.

“Oh yeah? And what kind of favor do you need,” Jack asked, crossing his arms.

With a sheepish grin she asked, “Do you think that you could give me a ride home?”

Jack wasn’t sure what to think. He wanted to help her out, but look where it got him last time. He felt the growing erection in his pants, and he thought about giving her a ride home because well, look where it got him last time. “I don’t know if that is such a good idea,” he said. “It didn’t exactly end up working out the last time I gave you a ride home, so… Maybe you should—”

She interrupted Jack and said, “Look, just give me a ride home, and if you want to stay you can stay, and if not then don’t, but I do need a ride home, and I would really appreciate it if you gave me one.”

“Fine,” Jack said, still somewhat reluctant.

The rest of the day passed like molasses rolling uphill in January for the both of them. Thoughts of the “ride” he was going to give his boss, and all of the possibilities that came with it ran through his head so much, that he was having trouble concentrating on any his work. ‘Did she want a repeat of the last time, or did she really just want a ride home?’ That question plagued Jack until it was time to go home.

Anita was having trouble concentrating on anything other than the ride home as well, unbeknownst to Jack. She wasn’t sure what was going to happen either. She just knew that the last time he gave her a ride home, she ended up having one of the most sexually stimulating, and satisfying nights of her life—that is, until she kicked him out of her house, and spent the rest of the night crying over her broken relationship, and wishing that Jack would come back to drink with her and keep her company.

Finally, at five in the evening, Jack heard the sound of high-heeled shoes approaching him. “Are you ready to go,” Anita asked, her brief case and purse already in her hands.

“I’m ready if you are,” Jack replied, shutting down his computer and grabbing his own bag. The hesitation was very clear in his voice and he was still wondering if this was such a good idea. He looked up at Anita who, and he almost couldn’t believe it, looked just as apprehensive as he did.

“Ok, then let’s go.”

They walked to his car in silence and when they reached it Anita could see that it was still messy, and he apologized for that once more. She too, once again said that she didn’t really care, and that it was ok. Neither one of them said another word for the entire duration of the ride to Anita’s house.

When his car finally pulled into the driveway, she asked him the question that his mind had been dreading to hear, but his cock had been hoping to hear. “Do you want to come inside for a drink?” She asked him hesitantly, not knowing what his answer was going to be this time. She just hoped that it wasn’t going to be, “no.”

“I don’t know if I should,” he said. “What if we—”

“Then we do, Jack…” she interjected. “We’re adults, and if you’re worried about my husband, it’s safe to say that he’s out of the picture for good at this point, so I am going to ask you again… Do you want to come in?”

“Fuck it,” Jack said, shaking his head. “Open the garage door.”

With his car safely within the confines of her two car garage, Jack and Anita got out. They both walked to the door leading into the house, and Jack watched Anita saunter up the small set of wooden stairs that led from the garage and into the kitchen. The minute he closed the door and walked into the kitchen, he immediately thought back to the last time he was in there. He pictured vividly the way she looked in front of him, on her knees, her face coated in his cum, and the look that was plastered across it. It was a look of a woman so turned on that she could barely contain the lust she was feeling. Her almond-shaped eyes were ablaze with passion, and everything about her at that moment screamed twisted, femininity. His cock started to twitch, and he wondered if there would be a repeat of some sorts tonight after the drinks started to flow.

Just like the last time he was there, the first thing Anita did was put her things on the kitchen table, and then walked over to the fridge to grab the wine, the beer, and the vodka. Jack walked over to the cupboard and grabbed the glasses. She pulled the cork from the wine bottle, and Jack pulled the cork from the vodka bottle. He popped the top off of the beer and she poured her first glass of wine for the evening. Clearly, they both mean business. Before they started to drink their wine and their beer, Jack picked up the two shot glasses and filled them both with the high end vodka. He handed her a shot glass, and he kept the other. He raised his glass, and she responded in kind.

“To whatever happens,” he toasted.

“To whatever happens,” she replied.

They downed the vodka and slammed the glasses on the table. She poured two more shots, and they downed those as well. Anita looked up at Jack, and she felt her pussy tingle at the memory of their last encounter. She thought of how good it felt to ride his face; to grind her hard clit against his masterful tongue, and then to have him blow his load all over her face. Her mouth watered when she thought about the way he tasted, and how much of his cum she had scooped into her thirsty mouth. She felt like such a whore when she showed him the load of cum that he had given her just before swallowing it all. She thought of how badly she wanted it all to happen again, but this time, she wanted him inside of her.

“So, what’s up?” Jack asked, bringing her back from her carnal reverie, and for a split second it made her angry.

“I don’t know. You tell me,” she said, sipping from her glass of wine.

“What do you want to know?” He asked, drinking his own drink and trying to lighten the mood.

“Stop playing games!” She said, cracking a smile.

He smiled in return and said, “I’m not playing any games.”

The alcohol was working on the both of them already as they began to loosen up. Jack contemplated making the first move but was afraid of rejection. Anita thoughts drifted back to the filthy things that he made her do. She wanted to do it again; but like Jack, she was hesitant to make a move. They were both thinking about that night, and neither one know that they were each thinking the exact same thing.

“So how do you feel about your separation?” Jack asked, unsure of what else to say.

“I don’t know to be honest. I’m upset on one hand, but on the other, I’m relieved. It feels good to be free from him and to be free of the way he treated me.”

Jack didn’t push her any further because he could tell that the separation with her soon to be ex-husband was not what she wanted to talk about with him. There was yet another pregnant pause between the two. “So uh… What do you want to talk about,” he asked, looking at Anita to see if there were any expressions on her face that he could attempt to read.

“Did you want to fuck me the other night,” Anita asked him, shattering whatever ice there was left to break for the evening.

“I think you know the answer to that,” he replied.

“Tell me anyways, Jack. I want to hear you say it. I want to hear you say that you wanted to fuck me!”

“Of course I wanted to fuck you Anita,” Jack said with all the emphasis he could muster. I wanted to fuck you in the kitchen after I came on your face, and then I wanted to fuck you in the shower, and again on your bed! I wanted to get as much of your mouth, your cunt, and your ass that I could get! I wanted to get as much as I could because…,” Jack paused. “Because I didn’t know if I would ever get the opportunity to get it again, but we both saw how that worked out, didn’t we?”

He expected Anita to apologize, but she didn’t. She just stood there and looked at him until she that she had to go to the bathroom. She walked, nonchalantly out of the kitchen and Jack followed her into the living room to sit down on the couch while Anita made a right towards the hallway that would take her to the downstairs bathroom. Three minutes later, he heard the bathroom door open followed by Anita walking into the living room, still fully clothed to Jack’s absolute disappointment. “Hey, why don’t you go and get the booze while you’re up,” Jack asked, and Anita looked at him with disgust, but the look quickly softened. She nodded, and then made her way to the kitchen. She came back a couple minutes later with hands full with two empty glasses, a bottle of wine, and a bottle of vodka. She placed them gently on the glass coffee table, and then headed back towards the kitchen to get her glass of wine, and his beer.

She sat down next to him, leaving less than an inch between their knees as she turned towards him to reengage the conversation that they were having before she went to the bathroom. “Where were we,” she asked, reaching for her wine glass.

“We were talking about what would have happened had I stayed that night,” Jack reminded her, grabbing his own drink from the coffee table as well.

“Oh… Yeah… That’s right.” She took a large sip of her wine and said, “Truth be told, if you would’ve stayed that night…” She finished the rest of the contents of her wine glass and said, “I probably would have let you fuck my pussy, my mouth again, and then probably let you finish off in my ass. God, I was so fucking horny that night, but… While we were in the shower… Something in me just clicked, and I got emotional… I had a moment of weakness, I guess.”

“Mmhmm…,” Jack muttered. “And this, “moment of weakness,” he said, making quotation marks in the air with his fingers. “Did it suddenly make you regret everything we had done that night? Or did you just not want me in your house anymore?” He stopped himself when he looked at Anita, who had a mixed look of anger, and hurt on her face. “I’m sorry,” he said. “I’m just trying to piece all of this shit together. I mean… You hurt me too by just kicking me out for no reason at all. It’s just that…” He stopped again, looking through his mind for what he wanted to say. “You… You blindsided me twice that night. First, you come downstairs wearing what you were wearing, and with the obvious intentions, and then not two and a half hours later, you kick me out for no apparent reason!”

“Did you like the stockings and the heels that I wore for you that night?” Anita asked, trying to direct the subject away from her feelings.

Jack wasn’t sure how to respond. He wondered whether or not she had even heard him, or cared about the way he felt about the whole situation. So once again, he said to himself ‘Fuck it,’ and said to her with all the emphasis in the world, “Fuck yes I did! I almost asked you how you knew I had a thing for stockings and heels, but there’s no way you could’ve known, unless you had caught me looking at porn at work and never said anything.”

“You look at porn at work,” Anita asked, incredulously.

“Uhh… Yeah… Sometimes, when I’m bored and there’s no one around.”

Anita looked at him like he was a total pervert, but then remembered the current situation that she was in and said, “Ok… Whatever… That doesn’t matter now. Keep telling me what you were thinking when you saw me.”

There was a smile planted on Jack’s face. “Fuck Anita… When I saw you come down those stairs, I just… Mmmm,”Jack paused for a moment to relive the experience and collect his thoughts. “I just wanted to walk over to you, push you against the wall and take you right then and there! God damn you looked so fucking sexy!” Jack had to stop himself before he started to ramble.

“I’m glad you liked them. I love to dress up! I do it every chance I get! Sometimes, I’ll even wear some of my lingerie to work, but under my clothes of course. They just make me feel sexy. And a little naughty I guess… Does that sound weird to you,” she asked.

“Not at all,” he quickly replied. “I’ve got a thing for women in lingerie and when I saw you dressed like that, or rather, undressed like that well, all I can say is, god damn!”

Jack’s words made her blush and she said, “I have a lot of lingerie, you know? My husband liked thigh highs and stuff like that too, so I have quite a collection. It was one of the few things that we actually had in common,” Anita said.

The two went silent again for a few minutes, and Jack imagined the vast contents of Anita’s “collection.” He would love to see it, he thought to himself, picturing her in all manner of sexy undergarments, and his cock start to harden. He saw her look down at his bulge, and he watched her lick her lips.

“I could take you upstairs and model some of it for you if you’d like. I have all kinds of fun things that I can show you,” she said proudly. “Plus, it’ll make up for what I did to you the last time you were over here.”

“Oh, fuck yes!” Jack said, hopping up from his chair.

“Bring the beer, the vodka and the wine,” Anita said, and Jack quickly turned around, grabbed the requested items and ran back towards the steps.

Once they were in the master bedroom, Anita told Jack that they both should shower first. She handed him a towel, and told him to use the bathroom down the hall while she used the shower in the master bathroom. She told him that once he was finished to sit on the bed, and wait for her because she was going to be a few minutes.

He obeyed his supervisor, and went to the hallway bathroom to shower. He washed himself quickly. He looked down at his already rigid cock. There was some stubble growing around his pubic area, so he decided to clean it up before their encounter. He found a razor and quickly, but carefully shaved around his shaft and then took the razor to his ball sack. Once he was satisfied that he removed enough hair, he rinsed off and got out of the shower.

He dried off quickly, and walked naked back to Anita’s room. The shower was still going when he opened the bedroom door. He closed it and got onto the bed. He looked up at the ceiling as he waited, contemplating all of the things that were going to happen as soon as the bathroom door opened. He began to stroke his rock hard cock while thinking back to the last night they were together; how he fucked her mouth, and how she rode his face. He thought about the way her caramel colored face looked coated with his cum, and how slutty she looked sliding his cum into her mouth with her fingers.

His thoughts were interrupted by the water cutting off. ‘Oh shit, here we go,’ Jack said to himself as he continued to stroke his cock, but after about five minutes of waiting, and still no Anita he had to stop himself. ‘Ok, Jack just relax and be patient. Don’t make yourself cum before the fun starts!’ Jack got up off of the bed and grabbed his beer. He took a pull from it, hoping that the liquid would cool him down both mentally, and physically. He thought about another shot of vodka, but decided against it. He was buzzed enough as it is, and didn’t want to get a case of whiskey dick right before he was about to fuck his boss’ brains out. He took another sip of the beer. ‘How much longer is she gonna be?!’ He got his answer thirty seconds later when the door slowly opened.

It was history was repeating itself all over again. As soon as he saw Anita, his jaw dropped to the floor and his cock pulsated. She stepped out of the bathroom dressed in a full body stocking. It was black, see-through and it tightly hugged every curve that Anita Jensen had to offer up to Jack’s lusting eyes. Her perky, C cup tits, capped with pierced, rock-hard nipples were easily seen through the sheer, fishnet material. Jack managed with consternation, to make his unbelieving eyes move further down Anita’s lithe frame. Between her legs, he could see an opening in the body stocking exposing her bald, and already damp cunt. Thick thighs, also encased by fishnet, led to calves that were accentuated by yet another pair five inch heels. These were not like the pair she had worn the last time he was there. These were similar to Mary Jane’s in the front, and had a strap that went over the mid part of her small, shapely foot.

Anita’s face was painted heavily with makeup, including a very thick coat of eyeliner and mascara; just the way Jack liked his women. Her full, pouty lips were painted maroon, and around Anita’s long neck was a black choker, complete with about a three foot long chain that hung from it like a proper, high-class leash. A high-class leash for a high-class slut, Jack thought.

“What do you think,” she asked; her voice raspy, and low.

“There aren’t even words, Anita. You look so sexy,” Jack exclaimed. His mouth was dry, and he wanted to wet it with her sex.

“I am glad you like it, but there is more,” she said. “I have more lingerie; more outfits… Would you like to see more Jack?”

“More?” Jack words caught in his throat, and he wasn’t sure. He did want to see more… Then again… Curiosity got the best of him, and he muttered, “Ummmm… Yes please!”

Anita smiled, but just before she left she told him that she has something else to show him first. He said nothing and she turned around, exposing her plump, heart-shaped ass to Jack. Keeping her legs straight, she bent over at the waist, exposing a jewel-encrusted butt plug; below it, was a pair of thick, glistening pussy lips. Anita looked back at him and shot him a smile that said, “Come fuck me! I dare you!” He knew it was just a tease, but his cock still jerked in anticipation. Unable to control himself, he started to get up, but she quickly shook her index finger at him, and told him to stay where he was.

“I thought you would like that,” she said seductively.

“You thought right!” Jack replied.

“So white boy… You sure that you wanna see me in something else? Cuz’ it looks to me that you’re already really liking what you’re seeing me in now.” She eyed his cock, which was at full attention.

“Goddamn, that is a hard fucking question to answer,” he said, sounding exasperated. “You look so fucking sexy right now, and I can’t imagine that you could possibly look any sexier bu—but I’m just gonna have to say yes.”

“Very well,” Anita said, turning her back to him; the butt plug barely visible between her thick ass cheeks, and she walked back to the bathroom and closed the door.

Jack was still reeling from the way Anita looked, and the butt plug that she had in her ass. The thought of sinking his cock deep into her asshole, and emptying his balls into her bowels ran through his mind. His hand reached for his cock once more, and he started to stroke it in anticipatory agony. It was so hard that it almost hurt.

Five minutes had passed when the door opened again. Anita stepped out of the bathroom this time, dressed in a pair of tan stockings, no panties and a pair of tan, six inch heels. Jack liked the black on her, but the contrast of the tan stockings wrapped around her mocha-shaded skin looked incredible. She was wearing nothing on top and her pierced nipples were fully exposed, and still as hard as rocks. She brought her hands to them and pinched them for effect, and she bit her lip to keep herself from letting out a moan.

“How about this?”

“I like,” was all Jack could say.

“I’m glad,” she said, her voice smoky, and her tone low. “But would you mind pouring me a glass of wine? Changing in and out of these outfits can make a girl really thirsty!”

“Yes ma’am,” Jack replied, hopping off of the bed; his cock swinging freely as he walked over to the dresser to grab her wine glass, and the bottle of Red Moscato that he had brought up for her. He poured her a glassed, and brought it to her.

“Thank you,” she said, taking the glass from him. She took a sip of the wine, and with her free hand, she grabbed his cock and gave it a light squeeze. “I can’t wait to have this inside of me Jack,” she said looking straight into his eyes. “I can’t wait to have every inch of it deep inside of my wet pussy! You gonna give me this dick white boy?”

“You’re the boss lady,” Jack said with feigned humility while his supervisor gently stroked his manhood, occasionally stopping to rake her fingernails along the underside of his shaft, sending goose bumps all over his body.

“So,” she said, taking another sip of her wine, “the butt plug… What do you think,” she asked while continuing to stroke him.

“What do you mean, what do I think? I already told you that I really like it,” Jack said.

“I know you like it but… If the time comes, are you going to take it out in and replace it with that fat cock of yours?” She squeezed his shaft harder, and Jack almost lost his balance.

“Anita,” Jack swallowed hard, “I would love to put my fat cock up your tight ass!”

“I knew you would,” she said, taking another sip of her wine, “But first I have another outfit I want to put on for you!” She pushed Jack back onto the bed, and walked back into the bathroom and closed the door.

Jack’s hand had once again made its way back to his cock, but he only squeezed it occasionally, fearing that if he stroked it, he would not be able to stop himself from cumming. ‘I gotta settle the fuck down,’ he kept thinking. He got up to pour himself a shot. Finishing it quickly, he popped open another beer, and nursed it while he waited for Anita to come out of the bathroom.

“Are you ready for me to come out,” she asked, and Jack who had accidentally choked a little on his beer, managed to get out a “yes.” He hopped off the bed just as she was walking out of the bathroom.
Anita walked out, once again in the black, platform Mary Jane’s she had worn earlier, but instead of black fishnets above them, white, opaque stockings with bows at the top of each one, kind of like the stockings that a schoolgirl would wear covered her thighs, and a plaid skirt that barely covered her cunt lips was wrapped around her thin waist. Completing her slutty schoolgirl outfit was a pair of black suspenders that ran tightly up her midsection and over her shoulders, managing only to cover her nipples, but their hardened state was still clearly visible through the elastic material.

Jack walked over to her, and wrapped his arms around her before she could protest. He put his lips on hers, immediately opening his mouth. Their tongues danced and Jack’s hands quickly brushed each suspender from her chest, exposing each bar-belled nipple to his bare chest. She pulled away from him, and asked him if he wanted to see anything else but Jack did not speak, instead he picked up her up, and she wrapped her legs around him. He immediately felt her sopping cunt lips against his cock. He brought her over to the bed and dropped her onto her back and got on top of her. They’d each had enough with the teasing, and the games, so they began to attack each other’s lips, kissing like people, mad with lust. It was time…

“Put your cock inside of me, white boy! Put it in me now!” Anita demanded, spreading her legs as wide as she could; exposing her hairless, dripping twat to Jack’s lusting eyes. He quickly obliged, grabbing his rock hard cock and lined himself up with her. “Please put it inside of me Jack,” she begged, “Please!”

Jack rubbed the white head of his cock against Anita’s caramel-colored lips of Anita’s pussy, mixing his precum with her plentiful juices. He rubbed the head against her clitoris, causing Anita jerk involuntarily. She moaned and once more, renewed her pleas for penetration, begging Jack to fuck her. “Goddammit Jack put that big fucking white cock inside of me now!”

Jack brought the head of his cock to the entrance of her cunt, and pushed forward. With just the head in, Anita let out a low, satisfied groan. He pushed his cock in further, and the sensation of her tight cunt enveloping his rigid cock nearly made him fill her with his cum that very instant. He focused all of his energy on trying to calm down. He had about four inches of his cock buried inside of her when he pulled it back out, causing Anita to groan once more. “Put it back in me,” she begged, and Jack thrust back in, this time deeper, and harder than before. He pulled back out to repeat the motion and he looked into Anita’s eyes, seeing the deep, soul-searing lust within them. He could see the wanton desire for him to ravish her body. He pushed all 7 ½ inches of his cock inside of her and Anita convulsed as her first orgasm took over her body, eliciting waves of ecstasy from her abdomen, and forcing her toes to curl within her heels.

“Oh my God Jack,” she whimpered. “I’m cumming already! Your cock is making me fucking cum already!”

He felt her pussy grip him like a vice as it milked him. He leaned down, taking one of her nipples into his mouth. “Oh fuck yes, Jack! Suck on my pretty tits while you fuck my pussy! Please don’t stop,” she said with haste as he chewed, and sucked on her hard, stainless steel-adorned nipple. He continued to thrust as deep into her as he could, slowly fucking her as her cunt continued to spasm around his cock. He kept his mouth latched onto her tits, increasing the force of the waves of pleasures that were surging throughout her lithe form.

“Is this what you wanted,” Jack whispered, pulling his mouth from her tit. “Is this how you wanted me to fuck your tight cunt?! Nice and slow?”

“Yes, Jack but now I want you to beat it up! Beat this black pussy up for me Jack, and make me cum again all over your white cock!”

Jack smiled, loving every word coming from her filthy mouth. He got off of her and pushed her onto her stomach; manhandling her as he lifter her up by the hips until she was on her hands and knees. He got behind her and lined his cock up with her inviting pussy. Wasting no time, he thrust every inch of himself back into Anita. “Oooohhhhh Fuuuuckkkkk Jack! Your cock feels so fucking good in my pussy!”

As he started to get into a rhythm, Jack briefly looked around to see if there were any open windows in her bedroom. ‘I hope her neighbors aren’t home,’ he said to himself as he looked over at the open window that shown straight into the house next to hers. He smiled at the thought of someone listening to him pound his boss’ pussy, and then he started to fuck her even harder.

“Fuck me Jack,” she yelled. “Fuck my sweet pussy! Beat it up white boy!” She started to push back, trying to force more of his cock into her insatiable cunt. Jack looked down at Anita’s heart-shaped ass; he loved how it narrowed so much at her waist. He ran his hands up and down her back, occasionally bringing them under her to grab onto her tits as he thrust into her. He brought his gaze back to his white cock as it disappeared in between her thick, black cunt lips, loving the contrast that the colors of their skin created. He felt his cum start to well up within but he wanted to keep fucking her. He looked for something to take his mind off of what he was doing. He looked at the butt plug that was lodged in her ass, and it gave him an idea. He grabbed onto it and started to pull it out. He pushed it back in swiftly, and started to fuck her ass with it.

“Does that feel good boss lady,” Jack asked, continuing to thrust the butt plug in and out of her tight, juicy ass.

“Yes,” She screamed. “Fuck my ass with it!! Get it ready for your big cock!”

“You’re gonna let me fuck that tight, black ass baby?”

“Yes Jack! Yes, I’m gonna let you fuck my fat ass!”

Jack was on the verge. He kept fucking her ass with the butt plug as he beat her pussy up with his cock as hard as he could for a few more seconds and then, abruptly, he pulled out, pushed Anita over and onto her back, not even giving her enough time to protest before his mouth was her clit, licking it furiously.

“Ooohhh Jack! Fuck! Oh, Fuck! Eat my cunt!” Anita’s body was jerking under Jack as he orally assaulted her hard clit, and he could hear her begging him to keep his mouth on her little button, but he had other ideas. He started licking the entirety of her pussy, starting at her clit first, and then dragging his tongue all the way down to her perineum with a pace so slow that it nearly drove Anita mad.

“Grab both of your legs and bring them back as far as you can,” he ordered, and she quickly brought each of her arms under her schoolgirl-stocking covered thighs, and brought her feet back almost to her head, giving Jack full view of the pink jewel-encrusted butt plug she had lodged in her ass hole. He grabbed it, and slowly started to pull the toy from her tight sphincter. She moaned, and groaned, and hollered, and begged for Jack to keep eating her cunt. She cursed and ranted, and even threatened to fire him, but he ignored her completely. He pulled the plug from her ass and set the sex toy onto the night stand. It was clean, which lead Jack to think that she had prepared to be fucked in the ass while she was in the bathroom taking her extra-long shower. Jack looked at her little star-shaped asshole; left slightly open by the toy that had been in it for the better part of an hour. Like her pussy, her ass was totally void of any hair, and Jack was thankful for this; he loved a bald pussy and ass. He leaned his face back in between her legs and started to lick gently at her tight pucker.

“Oh my God, Jack that feels really good,” she said, giggling, and with just a hint of nervousness in her voice. “No one has ever done this to me before.”

Jack had no intentions of telling her that this was his first time rimming someone, so he kept his mouth on her ass, slowly increasing the pressure of his tongue against her intimate flesh. Anita squirmed and took in deep gasps for breath. “It feels so good Jack,” she would keep telling him, and he would keep licking her tight asshole, getting it ready for his cock.

Anita could not believe that Jack was eating her ass. It was something that she had always hoped that her husband would do, but she knew that that would not have happened in a million years! She was ready for Jack’s cock though and between breaths, she managed to get out, “Jack please put your cock in my ass!”

He needed no further invitation. “Where is your lube at, Anita,” he asked and she directed him to the night stand. He opened the drawer and pulled out a large bottle of KY. He opened it, squirted some onto his hand and he covered his cock, and then her ass with it. “Are you sure you want my cock in your ass,” he asked her one last time while he aimed his cock at her puckered asshole.

“Fuck yes Jack,” she said without hesitation. “Please put your fat cock up my tight ass and fill it with your cum! I wanna feel that big, white dick swell, and explode in my tight ass!”

Jack felt his manhood twitch at her words, and he asked her how she wanted it. “However you want me Jack, but please put your cock in my ass!” Deciding to keep her in the position that she was in, he grabbed her by her thighs, and he brought her to the edge of the bed. The height of the mattress was perfect for him to be able to stand up while he plowed her ass. Anita was already moaning in anticipation for what was about to come. “Just go easy at first,” she cautioned. “Your cock is really big!”

He nodded, and pressed the spongy head of his cock between her fleshy, cocoa-brown ass cheeks, and against the puckered ring of her asshole. He rubbed up and down, sliding the head slightly into her pussy to ensure maximum lubrication. He slid his cock back down to her asshole, and pushed harder this time. His cock head started to disappear into Anita’s sphincter.

“Oh my god Anita! Your ass is so tight!”

“Easy Jack,” she winced. “Easy! I’ve never had a cock as big as yours in my ass.”

“Ok,” Jack said between heavy, nervous breaths.

He held his cock still with only about half of his cock head up his boss’ ass. He looked down at Anita in her slutty schoolgirl outfit, complete with white stockings and Mary Jane heels. The suspenders were hanging from her hips, exposing her pierced nipples to his hungry eyes. The way she looked to him, dressed like that, and with his cock at the entrance of her ass made something in him come alive, and he suddenly felt the urge to shove every inch of his cock up her tight ass, and fuck her with abandon; stopping only when he blew deep inside of her.

“Easy Jack,” she kept saying as he pushed more of himself inside of her. He felt her ass give just a little as the head of his cock entered her tight pucker. He looked up at Anita’s face. Her eyes were closed and her hands were on her tits; fingertips pinching her nipples. He pushed another inch of his cock inside of her. She gasped, and she opened her eyes and looked up at him. A mix of ecstasy and pain was on her face.

“Are you ok,” Jack asked.

“Yeah,” she said in a breathy voice. “Just be careful.”

Jack pushed another inch inside of her and then watched Anita’s right hand make its way to her protruding clit. She put it between her index and middle finger and started to move her hand in circular motions. “Push more in,” she said as she rubbed her clit. Jack obeyed, pushing another inch slower inside of Anita’s tight ass. He added another, and then another as she continued to loosen herself up with masturbation. After nearly five minutes of Jack pushing more and more of his cock inside of his boss’ ass, he finally had all 7 ½ inches of it inside of her. “Just hold still and let me get used to you,” she said.

“Ok,” Jack said, trying to be patient. “Just let me know.”

She took in a deep breath while she continued to rub her clit. “Ok… Pull it out and then push it back in, but just go slow!”

Jack pulled his cock out as slowly as he could; each inch reappeared to him, slick with lube, and in complete contrast to the caramel-shaded ass that it had been stuffed in. “I feel so empty now,” she said with an incredulous smile, and Jack wanted to tell her to make up her fucking mind. “Ok… Push it back in. Ohhhhhh,” she groaned as Jack’s cock disappeared once more, but this time, just a little faster. “Do it again,” she said. “Fuck that feels good!”

Anita’s ass started to relax more and more as Jack’s cock thrust in and out at a pace that was slowly gaining momentum. “Fuck me Jack,” she said finally. “Fuck my ass and make me cum again!” Jack wasted to time to obeying his superior. He pulled his cock almost all the way out of her ass and quickly pushed it back in, eliciting a moan from Anita. “Keep going Jack! Keep pushing it in harder! It feels good baby,” she said. “So fucking good!”

Jack continued to do as he was told, but he was not going to be able to do it for very long. He had been close to cumming for the better part of ten minutes now, and he couldn’t believe that he had managed to last this long. “Fuck my ass Jack! I’m close already,” she said to Jack’s relief. Her hand was furiously rubbing her clit as her left pinched her taut nipple as hard as she could stand it.

“Oh fuck Anita, your ass feel so good! I can’t hold out much longer,” Jack said, pumping his cock in and out of her ass as fast as he could without worrying about hurting.

“It’s ok Jack! I’m close too! I’m so close to cumming! It feel so good in my ass! Cum for me Jack! Please! Fill my ass with your hot load!”

Jack couldn’t stop himself. He started to pummel Anita’s ass as hard as he could, feeling his balls begin to swell. He was getting so close, and her words were only bringing him that much closer. “I’m gonna cum Anita! I’m gonna fill your tight ass with my cum!”

“Do it Jack! I’m cumming to,” she yelled, and Jack could feel her asshole tighten around the base of his cock as the muscles in her body started to contract. It was more than he could handle.

The first jet of his load came out of him as if it were being shot out by a cannon, and the second was just as forceful. They were followed by what felt like at least five more jets of cream that must’ve filled Anita’s ass to the brim.

“I can feel it,” Anita screamed as her own orgasm rocked her body. Juices flowed from her cunt as wave after pulsating wave shot from her clit and pulsated to every nook, cranny, crevice and hole that she had. “Oh my god Jack, I can feel you cumming inside of my ass! It feels so good! You’re cock feels so big! Ohhhhhhhh fuuuuucckkkkkkk,” she yelled as yet another orgasm took over her body.

When the last ounce of semen that Jack possessed within him was pumped into Anita’s tight, muscular ass, he felt a sense of sexual satisfaction that he had never felt before. It was as if his whole body felt empty, and full at the same time. His cock began to soften, and he slowly pulled it from Anita’s rectum. There was a “plop” sound when the head of his cock left the airtight confines of her ass, and cum began to flow out of her.

“Goddammit Jack,” she said almost completely out of breath. “That felt so fucking good! I wish I would’ve known that you were this fucking good in bed a long time ago because… Oh fuck that felt so good!” She stopped talking and started focusing on regaining her breath.

“Thank you,” was all Jack could muster. He was wiped out. His body was exhausted from the booze, the anticipation, and then the sheer hotness and taboo of what had just happened between him, and the women that, on Monday, will be telling him what to do because it was her job.

“So, what now?” He asked, collapsing next to her onto the bed.

“A shower,” she quickly replied.

She pulled off her heels and then her stockings, as she made her way to the bathroom. She grabbed two towels and yelled for Jack to join her from the bathroom. He obliged and made his way through the door. Anita had already gotten the water running and hopped in the shower. She was under the spray before the water had even had time to warm up, washing off all of the sex that had accumulated on her. Jack joined her but he did not try to touch her.

“Well, that was fun,” Jack said smiling, and trying to gauge her mood, and how she felt about what had just happened.

“Yes it was!” She said, washing herself off. She looked over at Jack, who looked hesitant. “Don’t worry Jack… I’m not going to kick you out this time. She grabbed his hand and pulled him towards her. Their lips met in a passionate kiss. An audible sigh of relief escaped Jack lips while he kissed her, and he wrapped his arms around her wet body.

Their shower lasted another ten or so minutes; each taking their time to wash the other’s body as thoroughly as they could. When they finally finished, they got out, toweled off, and then went back into the bedroom.

“So, you’re sure that you’re ok?” Jack asked, grabbing the bottle of vodka and drinking straight from the bottle.

“For fuck’s sake Jack… Yes, I’m fine,” Anita replied, grabbing the bottle from him and taking a long pull from it herself.

“Thank you for the fashion show. You looked absolutely incredible.”

“It wasn’t really much of one,” Anita scoffed. “I have plenty more outfits that I could show you! But it’ll have to be some other time because I’m really sore right now!”

Anita handed the bottle back to Jack and he took another swig. He put the bottle on the dresser and looked for his slacks so he could get his phone when heard Anita’s head hit the pillow. He heard a light snore coming from her.

Jack was still reeling from the events of the evening and wasn’t particularly tired at the moment. He waited a few minutes to make sure that Anita was going to stay asleep and decided to do a little exploring. He slowly got up off of the bed and went to the bathroom. He relieved himself, and then went to the walk-in closet that was connected to the bathroom. The closet was large but it didn’t take him long to find what he was looking for. In the corner towards the back, there was a large chest. There was no lock on it, so he opened it quietly. It was full of sex toys of all shapes and sizes. He ruffled through them until he got to the bottom of the chest. There was a small box. Jack pulled it out and opened it.

In the box was a collection of pictures and DVD’s. He pulled out some of the pictures and went through them. Most of them were of Anita in various nude poses. There was a man in some of them and Jack guessed to be Anita’s husband. Jack smiled in satisfaction when he saw Anita’s husband’s cock. “Mine is definitely bigger,” he thought to himself. He continued to shuffle through the photos until he finally reached something that peaked his interest. They were pictures of Anita, but in these, she was not alone. She was with another woman, and she was white! She was similar to Anita’s build but had much larger tits, maybe a D cup, or a DD. There were pictures of the two of them in a sixty nine position, pictures of the two them sharing Anita’s husband’s cock and there were some of the two of them sharing his cum. Jack looked closely at the white woman. She looked familiar but he couldn’t really tell for sure. Most of the photos were close ups, and poor quality, but Jack swore that he had seen the woman somewhere.

He put the pictures back into the box and placed back where he had found it. This was all too much for him! If someone had told him that in less than a month, he would be in his boss’ house late at night going through her closet after having just fucked her, he would have called them crazy. Yet here we was doing exactly that. He walked back out of the closet. Before he turned the light out he made sure that everything was exactly the way he found it. Satisfied that it was, he shut the light off and walked back to the bedroom. He still wasn’t tired and he really didn’t feel like staying, so he decided to leave. He walked up to the bed and looked at her once more. She was laying on her stomach and was dead to the world.

Jack stayed as quiet as he could as he dressed, and then made his way down the stairs. He looked around to make sure that he wasn’t forgetting anything. He walked through the kitchen door and into to the garage. “Fuck,” he said in a whisper. “How am I going to get my car out of here without her hearing the garage door open?” He fought with himself for a minute, and then decided that she was probably too dead to the world to hear anything, so he took a chance. He hit the button by the door that opened the garage door. It was one of the more quiet ones, and the he thanked god for that.

After he pulled his car out, we waited a moment to see if the door would close on its own, but while he waited, he saw a car pull up in the house that was next to Anita’s; the house her open window was facing. A car door opened, and out of the car came a buxom redhead who was maybe in her 40s. She looked over at Jack, who was still waiting outside of his car for the door to close. He looked back at him, and then he smiled. Ten seconds later, the garage door closed and he left, thinking to himself, ‘What a night…”

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