Spend the night with Goodbye as she convinces you to stay with Washington

You sat upon your bed in the Rowntree, pondering how strange it was that all of the world's CEDIT leaders were in one place and, stranger still, that a good number of them intended to offer you a highly indecent proposal to sway your loyalties towards their CEDIT division. You had to imagine that none of them would present this as a one-time deal; you clearly weren't so desperate for sex that a single fling would sway your opinion one way or another. On the contrary, each of them probably had ideas for all kinds of perks they planned to roll out for you, many of them illicit. The thought that you were the center of attention for each of them tonight made you feel powerful, which, in turn, made you feel horny. It was time to go do something about those feelings.

Were you actually thinking of leaving CEDIT Washington, after all of the time you'd put into getting a handle on the Goodbye Girls there and establishing mission control? You weren't quite sure, but either way, there was no need for Goodbye to think she already had this in the bag. If you made her sweat a little bit, you knew you'd get a more appetizing proposal tonight... and making Goodbye sweat was, traditionally, an extremely easy thing to do. You felt a bit bad taking advantage of her in this way, but you were turning down some very tasty alternate proposals to be with her tonight. You hoped she'd make it worth your while and held onto that hope as you left your single room at the Rowntree for her accommodation on the fourth floor.

You paused in front of her room-- 410-- then reached out your knuckles and gave a polite knock upon her door. "C-C-Ciao! You came! One second!" you heard your boss babbling, followed by the raucous noises of someone jumping out of bed, running to the bathroom to check their hair, and then nearly slamming into the door in their attempt to run to it. After that heavy door unbolted and then slowly opened, you were met by the view of your boss dressed in a lengthy bath-robe, wearing her brown, frizzy hair down in an unusually casual do. That seductive look was undone a bit both by her short stature and her thick, librarian's glasses, which she adjusted slightly as she spotted you standing in the hallway. "Come inside, Ciao. Quickly!" Obviously, she didn't want anyone seeing her welcoming you in while she was dressed this way.

Once inside, you reflected that she hadn't been in the least covert about her intentions. Her face was already red with expectation-- along with her lipstick-- and the bathrobe made the atmosphere immediately flirtatious. As you walked further in, feeling overdressed, she fidgeted near the doorway and watched you expectantly. You thought she was waiting for you to confirm that you'd come here to hear her scandalous proposal, or otherwise, only to celebrate.

Her eyes widened behind her glasses as you told her that she'd dressed appropriately. You were here to celebrate the successes of the past months and at the hearing today in the way that two well-acquainted CEDIT agents with Rabbit Badges would.

"O-Oh? Oh! Yes. I'm flattered that you decided to hear me out. I know you have a lot of options available to you right now. I overheard some of the others talking and, well, it was obvious someone was going to try to poach you. It really is a relief that you chose to come to me first," she responded, although she didn't sound relieved at all. She sounded nervous as hell. This was probably the first time she'd used her feminine wiles to try to manipulate an underling into doing something for her... you could sense she was an equal mix of nervous about the precedent it set and celebratory that the attempt had worked out for her.

You watched quietly as she poured champagne into two crystalline glasses, making a bit of a mess of her robe's sleeves in the process. Once she was finished and the two of you had clinked glasses, you reminded her that you hadn't actually made your decision yet. You needed to hear some thorough convincing.

The timing of that statement had been pretty rude; she ended up doing a spit-take with her champagne as her face went red. "R-Right! I haven't forgotten. Um... {if LARP with Goodbye > 999}Th-The usual in this kind of setting out to be pretty salacious, right? I-I think if we got up to something like that here... in a hotel room, with the others so close by... that really would be something, wouldn't it?{endif}"

You asked her if she wanted to try mixing it up with something unusual. Basically, you were interested in anal. This seemed like the perfect situation where you might get away with something like that.

"A-Anal?! I... I guess if that's something you're interested in... I wouldn't be opposed... B-But doesn't it hurt?" she questioned, looking a bit squeamish.

You chuckled, then told Goodbye frankly: you thought it might be the sort of thing she'd enjoyed.{if Goodbye's Kink > 999} You had ample experience with your boss by this point to prove that her sexual preferences trended towards the masochistic.{endif}

"I-If you're sure... but don't we need um... don't we need lube?" she questioned, gulping and watching you through her foggy glasses.

She did have a point, but you knew something that would at least get you close.

Soon enough, the two of you had relocated to the hotel's shower and turned it on to a steamy heat. You'd left your suit on the bed, while she hung her bathrobe up close at hand on a hook. You politely ignored her gratuitous make-up kit on the counter, as the two of you stepped inside together. It was lucky this was a VIP suite... Goodbye was not exactly thin, and her chubby body would have made it hard to maneuver as two inside a smaller shower. As it was now-- with this wide, glass box structure-- the hotel shower provided a perfect venue for a scandalous fling with your boss. "N-Now listen, Nathaniel... I'm not committing to do butt-stuff with you all the time, if it turns out I don't like it. I know you're thinking of this as a package deal, but we're just trying it this one time! If I don't like it, then remember, my offer is just normal stuff... Understand?" she asked, looking back at you with worry in her pale eyes. Her glasses had been left by the sink and were uselessly fogged; you'd probably need to help her with that later.

You nodded, while again reassuring her that she was nearly guaranteed to like this sort of thing.

"B-But you do have lubricant, right? I don't think just being wet is enough..."

At first, you thought she was referring to how wet her pussy had already gotten-- and it was sopping-- but she'd probably actually meant to refer to the shower's moisture. You told her that this hotel was equipped with something that'd work in a pinch: aloe gel, inside the shower. As she questioned that choice, you'd already begun to moisten up your hands with the stuff behind her back.

"S-S-So... How do I get it in there? Do I- eep! Nathaniel!"

You silenced the questions by giving her an answer, sticking a finger between the massive mounds of her pinkish flesh and into her waiting hole. As you began to move your finger and and out, while massaging one of her heavy, moist breasts with the free hand, you reassured her of the aloe gel's desirable qualities as a safe anal lubricant.

"Okay... I'll trust you," she spoke in a breathy voice, resting one hand against the shower's wall to stabilize herself while her hips began to wiggle at your touch. The softness of her body, always impressive, was made even more tantalizing by wetness; her whole body jiggled obviously and you found yourself playing with the curves, running your hand from her breast to her stomach, then down to massage her pussy. "Mmmm... I thought we were going to do anal...?"

You laughed, telling her that maybe you'd fit in two rounds-- one for each hole. With that, you began to eagerly rub your member up and down between the soapy surface of her gigantic ass-cheeks. They were honestly almost too voluminous and slick for this task; you found yourself sliding upon the quivering surface almost comically. When you finally failed to keep your straight-face and ended up chuckling, she turned her head to look over her shoulder, pouting. "You were thinking they're chubby just now, weren't you? Does that mean you don't want to do it? You do, don't you? Y-Your dick's pretty fat too, you know..." she grumbled, batting back and forth your penis's length in a way that seemed playful and horny rather than scolding.

Her words had only encouraged you. Instead of pulling away, you finally began to push yourself in, submerging first the head into the slick hole, followed by the rest of the spear behind it. It was a tight fit, but you had done a good job with lubrication; you managed to slide yourself a good way in.

"O-Oh! Oh God! It feels weird having something in that one!" she gasped out loud, narrating her thoughts as she clung one hand onto the shower's head and rested the other upon the wall. Pressing forward, you began to thrust, pushing her round body against the shower's wall and enjoying the feeling of smushing yourself into that softness of hers.

You asked her: weird and good?

"I-I haven't decided yet!" she returned, but the way she was affectionately returning your gesture by bucking back upon you with her hips seemed to make her body's answer clear. You eagerly clasped both hands around her hips and went hard, feeling her feet slip once or twice as the two of you went at it beneath the steamy shower. Soon enough, the two of you exited genial conversation, instead transferring to the grunts of sex: Goodbye was a moaner and you grunted along the way, feeling the tightness of her hole, at odds with the soft invitation of the rest of her body. Whenever she began to quiet down, you slapped the jiggling mass of her ass until she began to shout again. There was absolutely no way that whoever her neighboring CEDIT bigwig could get any sleep or fail to notice these noises of hers, but neither you nor she did anything to quiet down. You only made things louder, thrusting harder, squeezing harder, and reveling in the reactions of your submissive boss.

"I decided... I-I decided I like it!" Goodbye announced, wearing a goofy grin as she moved her hips in a circular motion against your groin. "Are you going to do it inside...?"

For now, you decided against it; when the two of you were ready to finish, you brought your dick out instead, resting it into the curve of her buttocks and stroking yourself against her until you got a good amount of cum out, leaving it upon the shelf of her ass. You allowed yourself to be as thorough as possible, seeing as the shower would get rid of any uncleanliness.

Wasting no time, Goodbye turned now to boldly wrap her arms around your chest, her short stature causing her to smile up into your face as she rubbed her groin against yours. "Hmm... Do you think it's going to come up for a second round?" she questioned. When you told her that was a distinct possibility, she beamed, spreading her legs to stand in an inverted Y position. "... Th-This was actually a pretty fun way to persuade you to do something for me. I may try it again some time. But, for now, can I count on you to stay in Washington...?" You told her that she'd made it pretty hard to say no. Feeling silly, you added the revelation: you'd never intended to go anywhere. You just wanted to have some hotel sex with her. "You're so bad sometimes, Ciao... Maybe I need to hire a second handler for you."

The two of you spent a while longer, embracing inappropriately as boss and subordinate inside the shower, before you finally actually cleaned yourself. When she finally bid you goodnight, looking pleased as she reclined, nude save her bathroom, you were forced to exit like a thief in the night, waiting for a silent moment. You couldn't let the other CEDIT leaders see you exiting the room like this, with damp hair in the dead of night. Of course, there'd be no hiding the night's events fully... whoever was in the room next to the bath had certainly heard you two going at it.

The exertion had been a nice workout before bed. You ended up sleeping peacefully, once you made it back to your room.