Meeting the boss

Note: Wrote this some time ago, unhappy with it, probably gonna cannibalize it for parts and rewrite it for proper submission on literotica but might as well post it here.

The now routine sensation of my vision dimming and coming back hits me again. When my vision cleared, I found myself at work in my shared office space at the marketing firm. I knew exactly what I wanted to do. My boss Diana was all I was thinking about, it wasn’t because she was hot, I mean she was a smoking 40 something but it was mainly the fact I just wanted to get some kind of ****, even if it wasn’t real. She treated everyone like dirt, made the entire team miserable and practically no one could stand her including the senior partners. The only reason anyone tolerated her was the money she made the company, she really was a genius when it came to marketing and she did actually have a thing or two to teach the guys working under her. But it’d been getting worse lately, she’d gotten another pay rise and seemed to rub it in all our faces, driving around in a new car worth more than what I’d make in a year or two, wearing designer everything and generally acting all superior, I desperately wanted to take her down a peg.

I immediately made my way over to Diana’s office, let myself in and locked the door behind me which immediately got an annoyed look out of her, saying “Jacobs, did you just lock the door? This better be good.”

“Oh it is. Diana, I want you to hike up your skirt, take off whatever you’re wearing under there and masturbate while you suck me off.”

Complete shock overtook her face before being replaced by disgust and anger before she replied “Jacobs I don’t know if you’ve just had a mental break or what but I’m going to give you 3 seconds be-“ but before she could finish her sentence, she found herself getting off her chair and kneeling down in front of me before hiking up her skirt and and pulling down the stockings and stylish black lace panties she wore, all while wearing a completely uncomprehending expression. The sight was enough to get me going and I pulled out my hardening cock right in front of her face.

“I d-don’t, what’s happening? I-I” Diana stammered.

“Simple really, you have to do what I tell you to. Like this, suck.” And just like that she took my offered cock into her mouth and dutifully began bobbing her head, swirling her tongue around my shaft and expertly blowing me while reaching her other hand between her legs and masturbating. Kinda doubted the real Diana would actually be this good but hey I wasn’t complaining.

She continued blowing me for about a quarter of an hour before I finally felt myself starting to cum so I gave her a quick command “When I cum on your face, you’re going to cum as well, now stick out your tongue.” Eh, I was feeling generous. I pulled my cock out and started jerking off onto her face as she opened her mouth and stuck out her tongue obediently while wearing a dumbfounded expression. Seeing her like that was hilarious and hot at the same time and really made it fun shooting my load onto her tongue, into her mouth and all over her face. As I did I noticed her groaning and twitching with her eyes shut, eyes she would have trouble opening later since one of them was glued shut with my cum. Before Diana could exercise free will and scream or something now that’d she completed my last command I quickly told her stay put and keep her tongue out like that. Taking out my cellphone, I snapped a few shots of her like that, with a puddle of cum on her tongue and splattering her face before switching it to video mode and telling her “Now Diana, I want you to scoop that cum off your face, into your mouth and eat it like a good girl. When you’re done, I don’t want you to do anything I wouldn’t like.” Despite the shock, rage, confusion and more playing out over her face, she still obeyed and delicately shoveled the rest of my cum into her mouth before swallowing it down. The footage looked weird since she seemed to be freaking out but whatever, it would work well enough and there was always another chance to get better film.

Diana didn’t scream but did ask me in an angry tone “What was that, how did you make me do that? You little shit, do you know how much trouble you’re going to get in? I’m calling the police.”

But instead of reaching for her phone she stood still. “I don’t think so Diana, I don’t think you’re going to do that. I think you’re going to do whatever I say, and look good doing it otherwise I’ll post those pictures and video on the internet along with a whole lot more I’ll make you do.”

“Fuck you.”

“That attitude’ll get you nowhere except trouble, look.” I took out one of the remote cocks I had and activated it, turning it into a rather realistic looking 8” dildo and handed it over to Diana, telling her with a wicked smile “I want you to jam that up your asshole right now, down to the base and don’t scream, take your time if you need it.” Diana’s eyebrows shot up as she took the dildo from me and moved it to her rear, I didn’t think her eyes could get any wider but they somehow did when she finally started trying to work the dildo up her ass. Her hand shot up to cover her mouth as she worked it up deeper. It took her quite a while considering the dildos size and the fact I didn’t lube her up. Long minutes passed and she eventually started tearing up slightly causing the mascara she was wearing to run, something I always liked the look of. Eventually, her hands dropped away from her mouth and ass, signaling she had finally done it. She was panting hard and her expression was pained, I think she was starting to get the picture. “See? Trouble. I think you’re going to want to be a whole lot nicer to me now Diana.”

Quietly and desperately she replied “Fuck, that hurt… Jacobs, you can’t do this, you have to stop.”

“I’m sorry Diana, but we’re really only just getting started. Think of this as long overdue for the way you treat me and everyone else” I said and enjoyed the mounting look of despair on her face. “Diana, I want you to masturbate with that dildo, using just your asshole, every day until you only have a little trouble sliding it up your ass. And when that happens, I want you to come over to my apartment. Oh, and leave it in your ass for the rest of the work day. See you later,” I told her and left her office without bothering to close the door behind me, I heard her scramble to shut it as I walked off. This was gonna be so fun.

***

For the next 2 weeks, I felt her use my remote cock to sodomize herself daily, gradually speeding up until she was able to slide almost the whole thing up her ass at a decent pace though still hesitatingly. And predictably, she was a whole lot nicer to both me and the rest of the creative team during those weeks. Halfway through though Diana came to me at work saying “Jacobs, please, I’ve learned my lesson, but please this has gone too far, I can’t keep doing… that thing you told me to do, it hurts, and it’s so awful I can’t get used to it.”

“Sorry Diana, no can do. And it’d be a good idea to learn to like it because truth be told, it’s pretty much all I’m going to have you do; I’m gonna be making you a real anal only whore, so that’s something you can look forward to,” I say with a mean smirk.

“Please, no, please you can’t,” she says with rising panic.

I stop her before she gets any further, “Diana, if you keep going on like this, I’m going to have to punish you for it. Do you want that?”

Shaking her head, she gives up and leaves me to it. I felt a bit mean but this was all just fun and games.

Finally after those 2 weeks, I hear a knock at my door and when I answer it, I see Diana wearing probably the ugliest, most unflattering clothes she had, it was a nice try. I don’t mess around and just get straight to the point. I lead her into the living room, get her to strip and lay down with her face on the floor and ass up, she quietly obeys the whole time.

I tell her simply, “Diana, I’m going to assfuck you now.” Despite positively knowing what was going to happen, she still whimpers. “That’s not all though. From now on Diana, you’re going to be addicted to being assfucked by me. You’ll hate it though, hate how it makes you feel, humiliated and like a dirty whore but you won’t be able to get enough of it, you’re going to crave the pain and humiliation. You can resist but the desire will just keep growing stronger and stronger until your begging me to fuck you up the ass. Do you like the sound of that?”

Diana whimpers again and exhales sharply at hearing me before simply replying “Yes Mr. Jacobs.”

Feeling slightly sorry for how pitiful she seems now I add, “But hey I’m not all bad, I’ll give you this. Rough, abusive anal sex is now the only way you can cum, in fact, the more degraded you feel the harder you’ll cum. The good news is, rough abusive anal is all you’re going to get from now on.”

I stripped down and lined my cock up with her asshole, noticing it looked heavily lubed, she was smart to do that. Skipping all foreplay, I just slammed my cock into her ass, bottoming out in one thrust and eliciting a muffled scream from Diana. I immediately start jackhammering into her ass without remorse. The prior 2 weeks had helped but they certainly didn’t completely prepare her for the assfucking she was receiving, she was squirming all over the place as I pounded into her ass and looked miserable, yet at the same time, my commands **** her to enjoy it. She was spreading both her cheeks open for me despite not telling her to. She wanted to give me better access, wanted me to sink deeper into her despite how awful it made her feel.

I suddenly pulled out of her ass and backed off, she mewled when I did and thrust her ass back, desperately trying to impale it on cock that wasn’t there. I went over to her pile of clothes and picked out her cellphone. “Unlock it” I told her, throwing the phone over. She got to her knees and only hesitated for a moment before obeying, looking scared and excited at the same time. I turned on the camera and set it to record her, then went to sit down on my couch and told Diana “You can go now if you want. If you don’t want to get assfucked anymore, you can just get dressed and go.”

She didn’t get up to leave, she stayed kneeling on the ground and fought against herself. I could see her straining to just get up but in the end, her shoulders just slumped and she shook her head.

“You want to stay? You want me to fuck you up the ass some more? My my, you’re such an anal whore aren’t you.”

“Only because you made me,” She snapped back.

Chuckling I say, “Touche, well, it’s all yours, fuck yourself on my cock then if you want it so bad.”

Slowly making her way over to me, she starts to turn around but I stop her, “Ah ah, I want you to face me when you’re riding me.”

She turns back around to face me, giving me a look of disgust and loathing before she climbs onto the couch with me, planting her feet to either side. She grabs my cock, aims it at her asshole and sits down on it, she starts off slow and tries to seem disinterested now that there’s a camera recording but soon drops the act and begins bouncing up and down as fast as she can manage, not once touching her pussy. She keeps it up for a few minutes before her legs get tired and she leans forward into me and starts levering her ass up and down my cock, while hugging me instead of bouncing her whole body. I can’t really film in this angle so I turn off the recording but get an idea. While she’s busy jerking me off with her ass, I go to Pornhub and go to upload the video, I do everything except press submit. I hand the phone over to her and tell her to take a look at it then turn my focus back to her asshole. I start pumping into her for the first time now with deep, long strokes. I fuck her far faster than she could lever down onto me, so fast that I occasionally slip out of her asshole and whenever I do, I make sure to hook open her ass with 4 fingers and pull it open wide so I can easily slide back inside. The first time I do, she suddenly hugs me tighter and shivers. I take the hint and keep her asshole gaped open with my 4 fingers and fuck her hole like that, slamming my whole cock in all at once repeatedly. While doing that, I tell her “I want you to upload that video, but only if you want the whole world to see you sodomize yourself, you can say no if you want.” I can’t see her face since its buried in my shoulder, but I do hear the phone clatter to the ground followed by a groan and feel her suddenly start spasming as she cums with my cock and 4 fingers buried in her ass. It’s enough to get me off too and I start spraying my load into her ass. As we both finish cumming, Diana leans back and looks at me, she looks completely miserable and mutters out “I hate you. Everyone’s going to see that. It’s going to get out and ruin my reputation.”

I give her a lopsided smile and reply by giving her another command, “You now love the taste of my cock after it’s been up your ass, in fact sucking on any cock after its been in your ass will cheer you up.” Diana looks crestfallen at this, and doubly so when I start recording again, but pulls herself off my cock nevertheless, gets to her knees and starts blowing me. She starts off delicately at first but soon she’s hungrily slobbering all over it, running her tongue up and down my length, noisily sucking and licking off every drop of cum, and when it’s completely clean, she gets back up on the couch and presses my still hard cock back into her asshole and bounces a few times before getting back to her knees and blowing me. She repeats the process several more times before I’m too soft for her to get it into her ass, it’s great how disappointed she seems when she can’t anymore.

“If you’re a good girl, I’ll let you post that one on your Facebook,” I tell her. She chokes suddenly and looks like she’s about to cry but I see her literally start dripping grool, it must be turning her on like nothing else.

“Please, please don’t make me do that, that’s too far.”

“You can say no if you want, it’s like with the last video, you could’ve said no.”

“You know as well as I do I couldn’t. I… I needed it too bad.”

“Well that’s on you. You can go now,” I tell her simply. Then getting another idea, I add, “Oh actually, when we aren’t having these little sessions, here’s what I want you to get up to. I want you to call up a bunch of guys, guys you really don’t like and organize a gangbang where you’ll only take it up the ass bareback, tell them they can invite as many friends as they want, that you don’t mind, in fact you’d want as many to join in as possible. Every time someone shoots a load up your ass, you’re going to push it onto a plate and lap it up while the next guy takes his turn. You’re going to do this say, once every week and you’ll do it for as long as it takes for two guys to fit in your ass at the same time, and when they do, you’re going to pay them for it. Oh and remember to record it all, you might feel like posting it online as well.”

At that, Diana did start crying lightly but also started masturbating at the same time. It was a good start to things.