Pleasing Juliette Ch 03

Disclaimer: I do not own Nashville and have no association with anyone involved in the show. I do not make any money from the writing of this story.

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Juliette should have fucked her assistant years ago. Actually she had, back during the dark days when she was going through assistance like nobody's business, either making them quit or firing them, Juliette somehow thinking it would be a good idea to fuck one under those circumstances, and her manager somehow thinking she would have the self-restraint not to jump her assistance if he hired a good-looking man for the job.

Somehow she had never considered fucking her female assistants, who were all mostly pretty, not even the always eager to please Emily who looking back obviously had a thing for her right from the start.

Although it was probably a good thing Juliette hadn't fucked any of the others, because it was hard to imagine anyone could be better at pleasing her than her dear sweet Emily.

She certainly couldn't imagine anyone kissing her better, Juliette pretty much locking lips with the other woman the second her manager finally took the hint and left, the two lovers continuing that kiss as Juliette slowly manoeuvred them slowly away from the main room and into her bedroom, the only thing ruining her mood being that she was beginning to worry Glenn was getting suspicious that might be something going on between her and Emily. Well, that and something else, but she was fairly confident Emily would say yes given her previous track record.

"Can, can I ask you something?" Juliette asked after she finally broke the kiss.

"Of course." Emily smiled.

"Well..." Juliette hesitated, her nervousness coming back full force, "I guess it's more of a favour. I mean, you don't have to do it. It's a big ask. But, I... I'd really like it if you said yes."

"Well, I am your assistant." Emily grinned mischievously and pulled Juliette closer, "It is my job to please you in anyway."

"I'm serious." Juliette huffed.

"So am I." Emily insisted, "I would do anything for you."

"Oh, thanks. In that case... since you've already licked every other part of my body, would you... will you lick my ass!" Juliette blurted out, then when Emily looked surprised quickly added, "It's clean. I gave myself an enema and everything. But you don't have to if you don't want too."

There was a long pause, and then Emily said, "Okay."

"Okay?" Juliette pushed.

"Yeah, I'll do it." Emily promised, "Would you like me to use my fingers too?"

"That would be great." Juliette grinned, then pushing her luck added, "And later, if you're up for it, maybe a toy? I bought a couple just in case you said yes."

Emily raised an eyebrow, "A couple?"

"Yeah..." Juliette blushed before admitting, "I'm kind of a massive ass whore. Hadn't you heard?"

"I assume they were just rumours." Emily admitted.

"Well, you should know by now to assume everything you heard about me is true." Juliette said bitterly, a brief silence falling over them before she double-checked, "Ya sure you're up for this? Cause I'm really starting to like you-like you, and the last thing I want to do is push you away."

"It's fine. It's not like this is the first time we'd be doing something new for me." Emily quickly pointed out, before asking, "So... how do you wanna do this?"

Grinning happily Juliette pressed her lips to Emily's for a brief kiss, pulled back and scurried to the bed, where she grabbed one of her pillows and put it in the centre of the sheets.

She then quickly stripped off her clothes and strategically got in the centre of the bed with the pillow resting on her lower back, lifting her butt up and providing all the access Emily would need.

Just to be sure Juliette spread her legs as wide as possible, after of course, making sure there are a couple of pillows under her head so she was comfortable and would get a good view of what was about to happen.

"I'd love to be on my hands and knees for this, but... you know." Juliette murmured, rubbing a hand over her swollen stomach.

"I know." Emily said, slowly stripping herself of her clothes before asking, "Do you mind if I don't just go straight in?"

"Actually, a little more foreplay would be great." Juliette admitted.

This admission had Emily smiling softly, and then joining her on the bed for another make out session, which Juliette genuinely enjoyed. Sometimes she wanted to get right to the fucking, as she constantly thought about sex and after hours of forcing herself to act professional it wasn't like she needed much warm-up.

But now she was feeling kind of nervous, and Emily definitely was, and that was exactly the right time for a nice long smooching session. Besides, Juliette liked kissing Emily a lot more than pretty much all of the men she had shared her bed with over the years.

In fact, she liked Emily in general more than pretty much all the men she had been with, thankfully Juliette did not have to analyse that now as she was lost in making out with her oh so precious assistant.

Emily really, really loved making out with Juliette. She had always enjoyed making out with her lovers in general, but she especially loved it when it was with someone she truly, deeply wanted, and she had never wanted anyone like she wanted Juliette.

Revelling in the chance to show Juliette that again Emily continued kissing the other woman while her hands slid across her pregnancy enhanced curves, without thinking Emily squeezing Juliette's ass, which although enjoyable made her nervous for what was to come.

So while she didn't completely avoid that area she mostly stuck to caressing Juliette's swollen belly and milk filled tits for the next few minutes.

Even when she broke the kiss she didn't move far, Emily simply switching to kissing Juliette's neck while her hands continued playing with that big belly and those wonderful boobs.

Of course kissing around Juliette's neck just reminded Emily that she was forbidden to leave a mark, because no one could know she and Juliette were kind of, sort of together, and while she had previously romanticised and even fantasised about sneaking around behind other people's backs the reality very quickly lost its appeal.

So it wasn't long before she was going lower, which she just needed to hear Juliette's happy moan to know that the impatient girl was in favour of this.

Nevertheless Emily was determined to draw the foreplay out a little longer, so she kissed her way down Juliette's chest as slowly as possible, and when she found herself working her way up a boob she ignored the nipple for almost a full minute.

It would have been longer but Juliette let out a little whine of complaint and not wanting to get an ear full Emily wrapped her mouth around the nipple she had been deliberately ignoring and gave it a nice long sucking.

She then repeated the process, kissing her way down one breast and up the other and then kissing around the nipple before finally taking it into her mouth, although this time she licked it first before she sucked it.

Back and forth Emily went, again mostly using her hands to caress Juliette's swollen stomach and milk filled tits, although in the case of the latter she also tweaked the nipple she wasn't working on and pushed the nipple she was working on more firmly into her mouth, which unsurprisingly got a very positive response from her boss.

However eventually, and perhaps inevitably, her hand slid down to Juliette's juicy butt, caressing the cheeks with first one and then both hands while literally burying her face in the country/pop star's cleavage and started licking and sucking her nipples pretty much as hard as she'd ever dared.

Juliette of course moaned loudly at this treatment. The only time she stopped in the next few minutes was when Emily motor-boated her boobs, which made her giggle a little, but mostly she just relaxed and moaned happily.

Sex had always been a great way to take Juliette's mind off her troubles. Sex with another girl, or at least sex with Emily, was the best way.

Even when it came to foreplay like this Emily was just better at it than all her other lovers combined, and Juliette still wasn't sure if that said more about herself than it did Emily or not.

Either way Juliette tried not to dwell on it right now and just enjoy the moment, especially when Emily started licking and sucking her nipples, which was hopefully assigned they were getting closer to what Juliette really wanted.

While Juliette had been very much in favour of some foreplay she was now warmed up and very ready to get her ass fucked. She initially told Emily she wanted an ass licking, but that was just because she was hoping she could start out with that and then work her way up until Emily was ramming her rectum with a nice big dildo.

Well, she definitely wanted an ass licking too, it's just that receiving only that would have been a terrible tease, as it had been months since her ass had been fucked, and Juliette was more desperate for it than ever. Still, she forced herself to remain silent for a few long minutes and just enjoy Emily's mouth and tongue worshipping her boobs.

Eventually though Juliette whimpered, "Emily, can ohhhhhhhh, can we please get to the ass licking now?"

"Sure." Emily quickly replied, pulling back and then biting her lip, "Would you mind rolling onto your side? Unless you'd rather be in another position?"

"No, no, that's fine." Juliette said, slowly rolling over and then after a brief pause told her assistant, "Thanks so much for this."

Emily smiled softly and then quipped, "Well, it is my job to please you."

That was a strain on their relationship, and while her tone made it clear that Emily was joking the look on her face made it clear she didn't find it funny.

There was an awkward moment that followed which said the same thing, then to try and get rid of the tension between them Emily quickly lowered her head and literally started kissing Juliette's ass.

So the blonde easily benefited from the verbal misstep, Juliette finding it easy to forget about that when she was pretty much getting everything she wanted. Or at least a wonderful appetiser to it, and what followed was very, very promising.

Instead of being repulsed by what Juliette was manipulating her into doing Emily seemed to really get into it. Even with this initial stage she eagerly covered Juliette's well rounded ass in kisses before pulling her cheeks apart and just as eagerly sliding her tongue up and down her ass crack before concentrating on where she needed her most, her needy little hole.

The needy little butt hole which hadn't had any real attention from another human being in months, just those first few gentle licks causing Juliette to cry out in a mixture of relief and joy. And soon after that Juliette began giving Emily some real encouragement.

"Oooooooh yessssssss, lick me! Lick my ass!" Juliette moaned shamelessly, "Mmmmmmm, oh Emily, you're so good for doing this for me. Ohhhhhhhh, I really don't deserve you."

Emily blushed at that last comment. Well, she blushed throughout the rim job, but even through all the dirty talk, and of course the act itself, that compliment made her blush the most.

Partly because it made her heart flutter, and partly because she had just been so focused on pleasing Juliette that she forgot to be embarrassed when she started rapidly lapping away at Juliette's butt hole and then literally pushed her tongue through it.

Emily was shocked that she was able to do that. Clearly Juliette really was an ass whore after all. Something that the world-famous country/pop singer was only too happy to confirm once Emily's tongue slipped past Juliette's anal ring.

"Mmmmmm yeahhhhhhhh, that's it Emily, become my butt licker. Mmmmmmm, lick my butt hole just like that, oooooooooh, you have no idea how good this feels. But I'll be happy to show you. Mmmmmmm yeah, I'll be happy to toss your salad like you're tossing mine. I wouldn't do that for just anyone Emily, but I'll do it for you. Mmmmmm, I'll even kiss your ass. Ohhhhhhhh yeahhhhhhhhh, most of my day people either want to tear me down or kiss my ass, but I love it when they actually do. Mmmmmmm yeahhhhhh, I love having my ass kissed, especially by you, oh yes, and I'll be your ass kisser if you'll be mine. I'll ooooooooohhhhhhhhhh Goooooooooodddddddddddd!" Juliette cried out as her ass was invaded by something wet and soft, "Oh God yes, fuck me! Fuck my ass! Mmmmmmmm fuck. Fuck my ass with your tongue Ems! Fuck it! Oooooooooohhhhhhhhhhhhh yeahhhhhhhhhhhhh, tongue fuck my ass, oh fuck! Fuck! Fuck me, that feels so good, mmmmmmmm, I love it up the ass! I love it up my ass sooooooo God damn much, ooooooooooh Emily, fuck me! Fuck me like the ass whore I am! Oh God Emily, I am such an ass whore!"

Pushed on by those words Emily not only pushed her tongue as deep as it would go into Juliette's ass but started hammering it in and out.

The ease at which she was able to do this more clearly prove that Juliette was an ass whore more than words ever could, Emily finding herself happily proving that as she spent the next few minutes with her face buried in between Juliette's butt cheeks.

Then without warning she slipped a finger into Juliette's butt hole, that finger sliding in as easily as her tongue, if not more so. Which of course got a long, loud happy moan from Juliette, followed by yet more encouragement.

"Oooooooooooh yessssssssssss!" Juliette moaned before crying out, "Fuck me! Yes, finger fuck my slutty little ass hole! Mmmmmmm fuck, that feel so good. Give me more! Mmmmmm yeahhhhhhhh, shove another finger up my ass. Come on Emily, stretch me out and make me ready for ohhhhhhhhhhhh yeahhhhhhhhh, that's it, mmmmmmmm, good girl."

That cute little bubble butt was so crushingly tight around her finger Emily was shocked that Juliette wasn't an anal virgin, let alone that she wanted more than a finger up her butt.

Yet despite her concern for the other girl's well-being Emily couldn't deny there was something erotic about pushing first one and then two fingers into the tight little ass of the world-famous country singer Juliette Barnes.

She even wanted to give her more. Oh yes, Emily wanted to give Juliette the kind of butt fucking that her boss was making it so clear that she desperately wanted, so it was no surprise she obeyed the next command without hesitation, if a little awkwardly.

"More, more, more! Mmmmmm, I want more! Oh Emily, your fingers feel so good, but they're just not enough for me. I want a cock." Juliette confessed, "I want you to go to that bag over there, pull out the strap-on I bought for you, strap it around your waist and fuck me with it. Fuck my ass! Ooooooooh please Emily, fuck my slutty little ass hole. Ohhhhhhhh fuck, I order you to fuck me up the butt."

Even though Juliette said more, a lot more, Emily didn't stick around to hear the rest. No, she scrambled to do as she was told, and even though there was part of her which seriously panicked when she pulled out the sex toy, particularly at the size of the dildo attached to the harness, Emily quickly took off her clothes and strapped on the dick. She then rubbed in a generous portion of the lube which was thankfully in the bag, otherwise Emily wasn't sure she could do this.

Although Juliette was helping out by immediately replacing those fingers with her own and hammering her back hole, Emily watching with fascination as her boss abused her own butt until she was called back.

"Emily! What the fuck are you waiting for? Get over here and fuck my ass!" Juliette yelled at her assistant, "I want that dick up my ass NOW! Do it! Fuck me! Please? I want it. I need it. Please give it to me. Come on Emily, please just give it to me. Yessssss, get over here and give me your cock. Mmmmmm, I want every single inch of it up my butt. Give it to me Emily, give it to me hard. I'm not some delicate flower. I'm an ass whore. And you know what else? I'm your boss, so when I say fuck my ass that means you fuck my ass. Oh God yes, mmmmmmmm, give it to me. Oh Emily, fuck me. Fuck me like the ass whore I am, mmmmmmmm fuck yeah!"

Juliette practically moaned with anticipation when Emily finally placed the head of the dildo against her needy hole.

She then bit her lip to prevent herself from complaining again as Emily hesitated, then just as she was giving in and opening her mouth Juliette found that the only thing that came out was a loud moan of pleasure as Emily pushed forwards and finally began to really stretch out her ass hole.

She went frustratingly slowly, but that just meant Juliette got to savour the feeling of her slutty little back door opening up for a nice big dick.

There was another pause, Emily still clearly very nervous, but Juliette didn't mind. Her butt hole was being stretched, that was enough at that moment. She did open her mouth again, although it wasn't to complain this time but to offer encouragement.

From the way Emily's eyes went wide in the process she must've thought she was going to complain though, which worked out well for Juliette, her panicked assistant slamming forwards and sliding not only the head but a couple of extra inches of dildo up her butt, the sudden completion of the anal penetration actually making her cry out sharply in pain, although truth be told Juliette got off on that as well.

"I'm sorry Juliette." Emily squeaked before trying to pull the dildo out as slowly and as gently as possible.

"Don't you dare take that cock out of my ass!" Juliette snapped, quickly adding in a softer tone when it was clear she had frightened her assistant, "I'm sorry Emily, but you have no idea how good this feels. Mmmmmmmmmm, it's been way too long since I had a cock in my ass, and yours feels amazing. Mmmmmmmmm, but I bet it's going to feel even better when it's all the way in. Oh yes, oooooooohhhhhhhh Goooooooooddddddddd, I want every inch of that cock in my slutty little ass. Please Emily, give it to me! Give my tight little ass every inch of your big dick and make me your anal whore!"

For a few seconds Emily just stared like an idiot at her, Juliette tempted to point that out like she had done with countless men in this situation.

But again, Emily had proven she was worth being patient with, and sure enough she did so once again, as after those few seconds she grabbed a firm hold of the toy cock and began slowly yet steadily pushing it into her boss's butt, and Juliette loved her for it.

What she loved even more was that big dick sliding through her back hole and forcing the walls of her rectum to stretch wider than they had done in months. Years, if she was being honest.

Actually, if she was being honest this was the biggest dick she had ever taken in her ass. Well, the girth wasn't much different, but the length was at least three inches longer than anything she had previously taken, and while that hadn't seemed like much when she was purchasing the strap-on it felt like each inch was a mile by the time the last of it was disappearing into her butt hole.

For a horrifying moment Juliette thought she might burst, or the dildo to end up poking out of her mouth, or at the very least get stuck up there, then gloriously she felt Emily's thighs connect with her ass cheeks, announcing she had got what she had so desperately wanted and now every single inch of that dick was in her butt.

Emily was dumbstruck. Where had the dick gone? Juliette was tiny, how could she have possibly taken a dildo that size up her butt! Was it curled up in her stomach?

How had Juliette pulled off what was essentially a magic trick? And how could she possibly be moaning with pleasure from getting her ass hole invaded by such a monster cock?

Who could get off on being anally violated in such an obscene way that their ass hole was this widely stretched by the dildo now invading it? The dildo Juliette had brought with this in mind. Had begged Emily to use her. And Emily had not only done it, but was actually finding enjoyment out of it!