Ashley's Inner Circle

BY : MTL
Category: Individual Celebrities > Ashley Tisdale
Dragon prints: 2266
Disclaimer: This is a work of fiction. I do not know or own Ashley Tisdale or Vanessa Hudgens or any other celebrities. I do not make any money from the writing of this story.

When the E! Network contacted them about doing a special recapping their friendship both Ashley Tisdale and Vanessa Hudgens jumped at the chance. It was a great opportunity for some exposure, but more importantly it was getting paid to do what they'd do anyway, hangout in their free time and talk. Just because they would have a few scripted things to say, most of which they'd already discussed 1000 times, didn't really matter as at least some of it they would have talked about anyway, and they would have a chance to really talk whenever the cameras were off. Even if that might have to wait until the end of the day.

Ashley had been looking forward to that a lot, but... but Vanessa had been acting really weird all day, and she just couldn't put her finger on it. She... she just, seemed to be looking at her a lot more. Staring really. And smiling. Well, she had always been a smiley person, but something about this was different. Then there were these casual touches she gave her, like putting an arm around her when they were close or placing a hand on her need to emphasise a point, which might have been innocent if it wasn't for the looks and the smiles. They were innocent enough that everyone else dismissed them, but Ashley couldn't stop thinking about them.

She also couldn't stop thinking about something Vanessa had said, so once the cameras were off and everyone had gone home Ashley timidly asked her friend without looking at her, "So, did you mean what you said in the documentary?"

"About what?" Vanessa asked, before smiling and pointing out, "We both said a lot of things."

"About..." Ashley blushed, hesitating for a second before continuing, "About the threesome?"

Vanessa raised an eyebrow, and then smirked, "I meant every word I said in the documentary, especially that."

"Oh." Ashley blushed.

"Why?" Vanessa pushed, "Jealous?"

Ashley scoffed, "Of who? You? Please, I'm not that desperate to kiss James Franco."

"How about Ashley Benson?" Vanessa grinned.

"Erm, no." Ashley said flatly, "I'm not gay."

"You don't have to be gay to kiss a girl Ash." Vanessa pointed out.

"I know. But no, I'm not jealous of you for getting to kiss James or Ashley. The other Ashley." Ashley said, adding the last part because it sounded weird to say her own name, "Or pretending to have sex with them."

"It wasn't all pretend." Vanessa said softly.

"Oh my God!" Ashley exclaimed with a smile on her face, "You had sex with James Franco?"

"No." Vanessa smirked.

It took way longer than it should have for Ashley to figure out what her friend meant, but when she did her little frown turned into a wide-eyed expression of shock, "Oh."

There was long pause and then Vanessa looked apprehensive, "Is that... okay?"

"Huh? Oh, yes. Yes of course it's okay." Ashley said bringing her friend into a hug, "You're my best friend Vanessa. I don't care who you sleep with."

Trying not to be put off by that Vanessa quipped, "There wasn't much sleeping involved."

"I bet." Ashley grinned, pulling back, "Well, tell me all the details."

"Well..." Vanessa grinned wickedly.

"Not the sex you perv!" Ashley quickly added with a giggle, and a blush, "I mean how did you hook up? Was it your idea? Who seduced who?"

"She seduced me." Vanessa admitted, quickly continuing, "It was just before we started shooting, and she thought we should bond. Like, all four of us because we're playing friends, but especially the two of us because we ha such an intimate scene together."

"So you all had sex together?" Ashley teased.

"Not on the first day." Vanessa revealed.

"Oh my God you slut!" Ashley exclaimed, "You fucked all of them?"

"Oh yeah." Vanessa grinned, "But mostly I fucked Ashley since our characters were supposed to be in love. Besides, Rachel was married, and Selena only join the fun when her girlfriend Demi was around."

"Demi! As in Demi Lovato?" Ashley exclaimed, before frowning, "Oh my God... I didn't think they were friends anymore."

"Yeah, but they reconnected big time." Vanessa grinned widely again, this time wiggling her eyebrows, "But like I said, the orgies didn't happen until later. Much later. And at first it really was about PG bonding. Well, kind of romantic PG, but still PG, you know? Like, we went to the beach, hung out, had dinner together and just talked about everything and nothing. I suppose you could say at least she bought me dinner first. Then we went back to her hotel room exchanging secrets and she told me about how she was basically dating her Pretty Little Liars co-star Shay Mitchell but they had an open relationship and they had both basically fucked every girl, and half the guys, on that show."

"Oh my God!" Ashley exclaimed again, wondering just how many times she was going to say that tonight. Then she wondered about someone she'd met in passing, and would even consider a friend, "Even Lucy?"

"Lucy? Girl, she's like the biggest slut on that show. Ashley told me she'd hooked up with the woman playing her Mom, and had done some seriously twisted role-play with her." Vanessa confessed to scandalise her friend, before quickly adding, "Not that she mentioned it when she was seducing me. No, at first she was just talking about Shay and the other leads of Pretty Little Liars, telling me about all naughty things they did together in increasingly graphic detail until she noticed I was getting hot and bothered. Then she went in for the kill, asking if I'd ever thought about being with a girl, and when I said yes she asked if I wanted to hook up. I answered by shoving my tongue down her throat, and then she gave me like the best pussy licking ever. Well, there was this one time she and Selena licked my cunt while Rachel's tongue was up my ass, but trust me, you'll never forget your first time with a girl."

"Wow..." Ashley murmured, so overwhelmed by what her best friend had been telling her that it took a few long seconds for those final words sink in, "Wait, what you mean I'll never forget my first time with a girl?"

Smiling widely, and hopefully softly, Vanessa scooted forward on the hotel bed they had been sitting on, "Ash-"

"Wait, wait, wait!" Ashley scooted back, panicking a little, "Are... are you trying to seduce me?"

"Not if you don't want me too." Vanessa admitted, before quickly adding, "I really, really don't want to make you feel uncomfortable Ash, but I literally spent the past few months moaning your name while another blonde girl went down on me. How could I not think about you, and how much I love you, when the other Ashley was making me feel so good. Sex with a girl is so amazing Ash. Words just can't do it justice, and I just... I just want to show you how amazing it is. But if you are totally against it I understand. I just... I just really want to make you feel good, the exact same way the other Ashley made me feel good."

There was then a long silence, which felt like a lifetime, as Vanessa clearly gave Ashley a chance to think about it while the poor blonde ended up staring like an idiot at her best friend. Vanessa had just revealed so much, which totally overwhelmed Ashley. Which was probably the point. That, and trying to turn her on with all that talk about her fucking other girls. The thing was, it worked. Oh God, did it work, and Ashley was 99% sure that Vanessa knew that. But did she want to really risk her most important friendship just because she was overwhelmed and found a bunch of stories, which might not even be true, appealing?

As if reading her mind Vanessa added, "Obviously I don't want to ruin our friendship, because you're really important to me, but that's also why I'm doing this, and I think our friendship could be even more amazing if it came with sexy benefits."

Ashley let out a deep sigh and then asked, "What if I don't like it?"

"Then we'll stop. I promise." Vanessa said firmly, "But I really think you'd like it Ash."

"How can you be so sure?" Ashley asked softly.

"Because I did, even though I wasn't sure at first." Vanessa said softly, "And you didn't exactly seem grossed out when I was telling you about hooking up with the other Ashley and stuff."

"I wasn't." Ashley admitted.

"Then why not take the chance? Vanessa asked, "What's the worst that can happen? You don't like it, and then things are awkward between us for a few weeks? So what? We'll both get super busy, and next time we see each other it will be like nothing happened. If you don't like it, and I'm pretty sure you will."

"I..." Ashley began.

"And I'm not proposing here." Vanessa continued, "We don't have to treat this is a big deal. Well, it is, but there are no strings here. No commitments. Just two girls having fun."

"I'm..." Ashley tried to start again.

"You don't even have to do anything. I'll do all the work, I promise. Just-" Vanessa was suddenly cut off by a pair of soft lips.

The kiss was brief, but lasted long enough to take both girls breath away, the two of them just staring at each other for a minute or two before Ashley softly smiled, "What happened to us? We used to be Disney girls for God sakes. We made a living being sweet and innocent, And now... now we're talking about having sex."

"Don't Disney girls deserve to grow up? Have some fun?" Vanessa grinned.

In response Ashley smiled bashfully, which Vanessa returned and then kissed her again. This time it lasted not much longer than a minute or two, the entire world falling away and the only thing Ashley was aware of was Vanessa's lips, tongue, and her very feminine body pressed up against hers, which was different for her, and really weird, but also exciting and hot. Then what felt like hours later Vanessa moved her attention to Ashley's neck, and the blonde was amazed to learn that she was now lying on her back with her best friend on top of her, the realisation causing a soft whimper to escape her lips only for the brunette to move back up to kiss her again. Not that it was necessary, because Ashley was suddenly very, very on-board with this.

Vanessa thought that was the case, but she didn't want to take any chances. Not when she was so close to getting something she'd wanted for as long as she could remember. And yeah, she already had more than she thought she would ever have from Ashley, but Vanessa was greedy and wanted to make every last one of her dirty little fantasies about her best friend come true. Both the ones she'd had since pretty much the beginning, and the ones she never knew she wanted until the other Ashley introduced her to the wonderful world of lesbian sex, and turned her lifelong crush on her best friend into a burning need to make her hers.

Fucking all those other girls had given Vanessa the confidence she needed to make her dreams come true, however she had to play it cool. It had been hard to restrict herself and only tell Ashley half-truths, and sometimes flat out lies, as once she started she just wanted to tell her everything. But she had been holding back her whole life, and she would happily do it just a little longer if she could make every little part of Ashley hers. Besides, there was something to be said for taking her time and enjoying her conquest, Vanessa loving the way that Ashley was easy to seduce, and she loved kissing her even more, constantly switching between her friends lips and her neck for the next few minutes before making her way downwards.

To Vanessa's delight Ashley eagerly helped her take off her top and bra so she could have access to her perky little titties. Vanessa took full advantage of that by slowly kissing up one of those titties and then wrapping her mouth around one of Ashley's nipples. Ashley whimpered, gasped and moaned before Vanessa started sucking, and when she did her best friend let out the cutest little cry which made her grin around that nipple and slightly increased the suction. Then Vanessa kissed her way down that breast and up the other so she could repeat the process, soon afterwards going back and forth between Ashley's nipples and beginning to swirl her tongue around them, which got an extra positive sounds from the other girl.

As she continued getting those sounds, and Ashley seemed nice and ready for it, Vanessa did eventually move on. She lingered on the other girl's tits for maybe a little longer than necessary, but again she was just being cautious. Which seemed to pay off, as it seemed Ashley couldn't remove her shoes, socks, pants and panties fast enough. It was almost a shame, because Vanessa kind of wanted to remove Ashley's panties with her teeth, but hopefully there would be time for that later. Besides, it was hard to feel disappointed when Ashley Tisdale was naked in front of her, and unlike all those other times Vanessa didn't have to force herself not to stare and only give her friend the occasional longing glance. No, she got to look at her in all her glory.

Clearly Vanessa overdid it given that Ashley blushed and asked, "What?"

"Nothing." Vanessa murmured, shaking herself out of her thoughts, "It's just that, you're so beautiful."

"Thanks." Ashley blushed even more, "You too."

"Yeah?" Vanessa grinned.

"Yeah." Ashley smiled shyly, again blushing a little as she added, "But It's not exactly fair, you know? Here I am all naked, and you're... not."

"Yeah, that is unfair." Vanessa agreed with a nod, and then grinned, "Let's see what we can do about that shall we?"

Ashley hadn't really thought through her words, and momentarily regretted them when Vanessa pulled away from her. Well, she continued to regret it as she could have been getting her pussy licked right now if she'd have just stayed quiet, but she didn't complain, or indeed say anything, as she was too dumbstruck from watching as her best friend Vanessa Hudgins slowly stripped off her clothes in front of her. Which had happened before, many times, but Ashley had never really been paying attention before, which now seemed like a crime, because although she had always known that her friend was beautiful it felt like she was truly seeing her for the first time, and it literally took her breath away.

"Wow." Ashley murmured softly, then blushed as she hadn't meant to say that out loud.

She was then rewarded for her slip up with a happy smile, quickly followed by a soft kiss and became anything but as Vanessa gently pushed her back down onto the bed. They made out for a few long minutes, and then Vanessa began repeating what she'd done before, namely kissing her way down Ashley's body while lingering on her neck and particularly her boobs. The latter was particularly long, which made Ashley whimper pathetically, because she was more than ready for some attention else where, but she just couldn't say the words. She couldn't even think. Mostly because it was hard to think at all during this overwhelming experience, although she came very close just before Vanessa finally reached her final destination.

If all the previous teasing wasn't bad enough Vanessa pause when she reached that destination and looked up at her with a wicked little smile which for a second Ashley thought might make her cum by itself. Then Vanessa finally pressed her face in between Ashley's thighs, stuck out her tongue and slid it slowly over the blonde's pussy, causing Ashley to let out a cry of pure joy. That first lick was long, slow and travelled all the way from the bottom of her sex up to the top, Vanessa then repeating the process, making Ashley not only cry out but moan, groan, whimper and gasp in pleasure as for the first time in her life another girl went down on her.

Her best friend! Her best friend was going down on her! Her best friend who was a girl! A girl was going down on her! Vanessa! Oh God, her best female friend Vanessa Hudgens, a girl she grew up doing Disney movies with was now licking her pussy and Ashley was loving every second of it. God, she never wanted it to stop. She wanted Vanessa to lick her forever. Yes, regardless of the consequences Ashley desperately wanted her best female friend Vanessa Hudgins to lick her pussy just like this for all eternity. Well, maybe she could show her clit a little more attention, but right now that was a tiny nit-pick, otherwise Ashley felt like she was in heaven.

Vanessa also felt like she was in heaven. She also briefly thought it could be better, like if she and Ashley were in a 69 or the other Ashley was licking her pussy at the same time she worshipped her favourite Ashley's cunt, but that was just a sign that she had been spoilt with all the sex she'd been having lately. To her credit despite how tempting it was to get lost in those fantasies Vanessa was able to concentrate on the task at hand. Although she didn't deserve too much credit for that, as this was one of her biggest fantasies come true. And perhaps the most important one she was going to try to fulfilled tonight, because if she got this right she'd be able to talk Ashley into anything. Or at least that's what Vanessa was hoping.

It certainly helped that Ashley was responding so positively to all the gentle touches that Vanessa was giving her. It wasn't surprising considering her face was between her legs and she was now gently licking Ashley's pussy. And after all that positive reaction to the build-up it would have really hurt Vanessa's feelings if she was forced to stop now. Sadly that was a real possibility, as Ashley could freak out. But so far she had been more open to this than Vanessa had dared to dream back before she had met Ashley Benson. Now though Ashley Tisdale was naked before her and moaning, groaning, gasping and crying out in pure pleasure with every stroke of her tongue.

Which was good, because Vanessa never wanted to pull her face away from between Ashley's legs. Yes, screw her own selfish desires, Vanessa just wanted to spend the rest of her life making her best friend feel good. Well, maybe there was a little selfishness to it. See, ever since the other Ashley introduced her Vanessa had become a little bit addicted to licking pussy, and this was easily the tastiest twat she'd ever sampled. Sure, Vanessa was obviously biased, but hopefully she would be able to talk Ashley into letting her friends sampled this tasty treat for themselves so they could see just how yummy her best friend's pussy was. In the meantime, Vanessa was very much going to enjoy having Ashley all to herself.

Part of that was wrapping her mouth around Ashley's entrance so that she would be able to get every drop of that precious cream which was now flowing out of her friend. Yes, licking up that honey wasn't enough any more, Vanessa needed to make sure it went right down her throat and into her belly were it belonged. Of course the downside to this was she knew it would pushed them closer to the end of this wonderful act. Although that was also an upside, as Vanessa couldn't wait to taste Ashley's cum. Especially as she knew it would somehow be even more yummy than her regular pussy juice, if her experience with other girls was anything to go by. And of course, she was really, really looking forward to hearing Ashley begging her to make her cum.

Ashley was almost overwhelmed by the need for that, but everything she was feeling was so overwhelming she still didn't want it to end. And if that meant enduring some almost painful pleasure she was willing to do it, and more. Although it also meant she had to stare up at the ceiling and desperately try and prevent herself from closing her eyes, which only intensified her feelings of ecstasy, or looking down at her best friend nestled in between her legs which had the same results. Only that was more intense, because Ashley still couldn't believe Vanessa was doing this to her. That she could have done this to her before. That they could have been doing this all along.

It was almost painful to think she could have been experiencing this pleasure but hadn't because she was too afraid to try it, or because Vanessa was too chicken shit to seduce her. Yes, apparently Ashley was easy to seduce, at least for Vanessa, and in that moment Ashley dearly wished her best friend had done it much sooner. And yeah, this was on her too, because apparently Vanessa would have been equally easy to seduce for her. However Ashley hadn't known she liked girls. But now she knew, and she fully intended to make up for lost time. Yes, Ashley didn't care what she had to say or do, she would experience this again. And perhaps more importantly, at least for now, she would convince her best friend to make her cum.

Soon after the pleasure became literally painful Ashley whimpered, "Please Vanessa, make me cum. I need to cum. Please? Fuck me and make me cum. Please, mmmmm, I don't care what you have to do, just do it. Oooooooooh fuck, I'll do anything if you make me cum. Anything! Please Vanessa, I OH GOD! OH FUCK! OHHHHHHHHH YESSSSSSSSS, AAAAAAAAHHHHHHH FUCK ME VANESSA, FUCK ME! FUCK ME! AAAAAAAAAHHHHHHHHH GOOOOOOOOOODDDDDDD, OOOOOOOOOHHHHHHHHH SHIT!"

Perhaps Ashley should have been worried by the fact that as soon as she promised to do anything Vanessa gave her exactly what she wanted, but honestly she was too busy cumming to care about that or anything else. All that mattered was the incredible climax which shot through her body the second Vanessa slammed her tongue as deep inside her as it would go, Ashley's eyes going wide as she threw her head back to let out the loudest scream of the night. She then continued screaming incoherently as she was rocked by the most powerful orgasm of her life, which was somehow followed by another, and another, and another.

She'd heard women could have multiple orgasms, but Ashley hadn't thought it was actually possible until Vanessa proved it was. For that she would be forever grateful to her best friend, and in the few moments that she could actually think coherently, which were few and far between, Ashley promised herself she really would do anything Vanessa wanted. Because no matter what it was, it would be worth it, and she owed it to her wonderful best friend for making her feel like this. Yes, Ashley was determined to somehow return the favour, which was her last coherent thought for a while as she became completely mindless from the ecstasy she was feeling.

Vanessa was also mindless for a while as finally having Ashley Tisdale's girl cum hit her taste-buds completely overwhelmed her. Luckily she had plenty of experience now and as a result her body switched to autopilot, quickly removing her tongue from Ashley's cunt so she could concentrate on swallowing the heavenly liquid. Not that there was much swallowing required, as Ashley's cum pretty much squirted straight down her throat and into her belly were it belonged, and the only reason Vanessa got a good taste was because there was plenty of it. Then when Ashley's orgasm began to subside Vanessa's tongue pretty much shoved itself right back into Ashley's pussy and actually succeeded in fucking her briefly before repeating the process.

When Vanessa became accustomed to this heaven she smiled with blissful happiness at finally being able to make her best friend Ashley Tisdale cum in her mouth. And that somehow it was better than she'd ever dreamt. Although that wasn't that surprising, as previous experience with girls told her that was true, but still Ashley's responses to everything she was doing was just so positive, which was the best thing about this. No, the best thing about this was it almost guaranteed this wouldn't be a one time thing. That they would do this again. That she would be allowed to tongue fuck her favourite Ashley again. And maybe she would even be able to do anything to her, just like her friend had unwittingly promised.

Desperately wanting to ensure that Vanessa made Ashley cum as hard and as frequently as possible. She wanted to just stick to using her mouth and tongue for that, but they both got tired, and Vanessa knew that she had to pull out all the stops to make sure all her dreams came true. So reluctantly she moved her mouth upwards to wrap tightly around Ashley's clit and then pushed first one and then two fingers inside of her friend's welcoming twat. Vanessa then began switching between fingering and tongue fucking Ashley, getting at least the majority of the heavenly cream in the process, although a good amount ended up on her face, at least some of which she would get later, and would only make what they did next that much more fun.

Maybe Vanessa should have fucked Ashley into unconsciousness and called it a night. It would have been the selfless thing to do, and there was definitely something to be said for not pushing her luck. But Vanessa just couldn't help herself, there was one thing she desperately wanted, and she couldn't help at least try to get it. So when she sensed Ashley was nearing unconsciousness Vanessa slowly, and somewhat reluctantly, bought her friend down from her high and then pulled her way up her body to press her lips to hers. To her delight Ashley didn't hesitate to kiss back, even pushing her tongue into Vanessa's mouth so she could get a really good taste of her own cum and pussy cream. Which was definitely promising for the future, although it had little to do with what Vanessa wanted right now.

Ashley assumed that Vanessa would just want her to return the favour, so it seemed a good idea to test the waters by kissing Vanessa back. Besides, she desperately wanted to thank her for the ecstasy she had just given her, and kissing her seemed like such a small thing, even though it proved difficult given how exhausted she felt right now. The kissing somewhat helped with that, as did tasting herself, which Ashley had never done before but like with everything else she found it bizarrely enjoyable, at least in this context. Especially as Vanessa's equally naked body was pressing down on top of hers, and she could feel just how wet her best friend was from everything they had done, but probably particularly from eating her out, which was an incredibly thrilling thought.

When she finally broke the kiss Vanessa asked huskily, "Did you mean it?"

"Huh?" Ashley frowned, and hoarsely added, "What?"

"Did you mean it when you said you'd do anything?" Vanessa clarified.

"Oh." Ashley blushed slightly, "Yes."

Vanessa hesitated briefly, then asked, "Have you ever tried anal?"

"What? No, gross." Ashley replied automatically, before her eyes went wide, "What? Really?"

"Yeah." Vanessa replied sheepishly.

After a pause Ashley pushed, "With a finger or..."

"With a strap-on." Vanessa clarified, quickly adding when she saw the look on her friend's face, "I know that might sound scary, but nothing made Ashley Benson cum harder then when I fucked her up the butt with a strap-on. Or the other PLLs. And God Ash, have you seen your ass? It's like it was made to be fucked. It's... it's perfect. And like the most fuck-able thing ever. So please Ashley, give me your ass cherry. You didn't think you'd like girl on girl so much, and it totally just made you cum so hard you almost forgot your name. Don't lie, the proof of it is all over my face. And I think... I know I could do the same if you give me your ass. So please, do this for me Ash. I'll do anything if you just give this a try for me."

If she was being truly honest with herself Ashley figured she would always try anal, but it would be with her husband, or someone she was sure was the one. Even then only if they pushed her for it, but now she was genuinely considering doing something she had always considered gross and weird, and they weren't even dating. But this was more than that. This was her best friend, Vanessa. She couldn't imagine loving anyone more, especially after what Vanessa had just done for her, which definitely should be rewarded. And besides, she had promised Vanessa, and more importantly herself, that she would do anything her best friend wanted because of those incredible orgasms.

So against her better judgement Ashley cautiously murmured, "If, if I wanna stop-"

"We'll stop. I promise." Vanessa swore gleefully, "And I'll spend like an hour making sure you're totally ready for it."

 Ashley bit her lip and then blushed, "And, and you'll be gentle."

"Absolutely." Vanessa quickly agreed.

"And you won't tell anyone about this." Ashley pushed.

Vanessa hesitated, and then clarified, "If when I'm done with your cute little butt hole, you don't want me to tell anyone, I won't. But, the thing is Ash, I think you will. I think you'll want me to tell my friends all about the fun we had tonight, so they can fuck you too. Ooooooh yeah, when I'm done with you you're going to want to meet my new friends, and you'll want me to tell them all about what we did tonight, so they can do it to you."

Blushing even more at that Ashley admitted, "Maybe. I mean, I... I'd like them to eat my pussy, and maybe I'd even enjoy eating theirs, after some time eating yours. But, up the butt? I can't see myself doing that more than once. But I'd do just about anything for you, especially after making me cum like that."

"Oh Ashley, you don't have to worry, because I'm about to make you cum like that again.." Vanessa promised with a wicked grin, "Oh yeah, I'm going to make you cum so hard when I take your virgin ass that will become a total anal slut, desperate for cock in her tight little butt."

Again blushing Ashley slowly turned over onto all fours, grumbling as she did so, "Yeah, right. You're just lucky I love you."

"I love you too." Vanessa grinned, becoming a mindless statue for a few long seconds as Ashley presented her beautiful bubble butt to her and she became completely lost in the idea that she would finally get to butt fuck her best friend, eventually adding dreamily as she reached down to stroke those amazing cheeks, "And I love this ass."

If it wasn't for how giddily happy this was all making the woman who just made her cum so hard that Ashley would have probably protested. Hell, she would never have even considered giving up her butt cherry. But it did, and suddenly Ashley found herself on all fours, just waiting for her best friend Vanessa to take her anal virginity. God, how was this happening to her? Oh yeah, the incredible lesbian sex. Well, at least Vanessa had promised to take plenty of time to prepare her. Although maybe too much time, because there was a long pause between when she turned over and when Vanessa finally touched her, and when she did it was just to massage her butt cheeks like she was in some weird massage parlour. Then all of a sudden Vanessa leaned down and pressed a kiss to her ass.

"Oh my God!" Ashley exclaimed in surprise, and then giggled as Vanessa began covering both cheeks in kisses. She was just about to tease that her friend was now officially an ass kisser when Vanessa pulled her cheeks apart, pressed her tongue against her taint and then slowly push it upwards, sliding over her most private hole and working its way up her ass crack, before repeating the process, causing Ashley to cry out loudly, "Oh my God! OH GOD! Oh God. Vanessa? Oh fuck! You're licking my ass! I can't believe you're licking my little ass hole!"

"Shhhhhh, relax baby." Vanessa said softly, "Trust me, natural lube is always the best. And more fun."

Then Vanessa pushed her face deep in between her cheeks and then really started to go to town on her butt hole, causing Ashley to cry out and swear again. It certainly wasn't Ashley's idea of fun, at least when it came to giving a rim job. That was definitely something she'd never considered doing, and would have probably said no even if that's what Vanessa had asked for. But receiving one? Well, it wasn't her tongue touching an ass hole. And she had to admit, it felt kind of good. Twisted and really wrong, but good. And Vanessa clearly knew what she was doing, which was a good sign for things to come. But also a bad thing, because Ashley didn't want to be a anal slut, and she was now very worried that Vanessa was going to turn her into one with ease.

Vanessa had wanted that for a very long time, and was determined to get it. But she was also determined to give Ashley the best rim job possible. Partly so Ashley could embrace her destiny as an anal slut, and most importantly her anal slut, but mostly because she just loved eating ass and she wanted to make Ashley feel good. Which was why she slowly began zoning in on that tiny little hole, making her licks smaller and smaller until she was only licking Ashley's ass hole. She then swirled her tongue around that little hole, and wrapped her mouth around it so she could occasionally suck it as well as lick it. Finally, she began trying to push her tongue inside.

Even though Vanessa had doubted that Ashley was telling the truth earlier she was very grateful for confirmation in the form of her she yelling at the tip of her tongue into her best friend's tight little butt hole. It would have broken her heart if someone else had gotten to Ashley's tightest of holes first, and Vanessa was on cloud nine with the knowledge she was about to become the one to pop this precious cherry. But again she was determined to give a thorough rim job, so she let go of the butt cheeks she'd been holding apart throughout so she could spend a few glorious minutes smothering herself in Ashley's ass while getting down to some serious butt munching. As she did that Vanessa brought her hand up to rub Ashley's pussy, partly to increase her friends pleasure, but mostly to prepare her for what she did next.

Namely kind of take Ashley's anal cherry with her finger, both girls crying out as she pushed it into her, the difference being that Vanessa actually spoke some words, "Oh God Ash, you have no idea how long I've waited for this."

Which of course only made Ashley whimper, although as with the other sounds out of her mouth there was pleasure mixed in with the embarrassment, and she never told Vanessa to stop, but even when she started violating her with her finger. In fact she continued moaning in pure pleasure from the beginning of the rim job to the moment Vanessa pushed the tip of her finger into Ashley's ass hole, and even that was mostly pleasure, even when Vanessa pushed her finger up to the knuckle and her friend's tight little ass. Which definitely confirmed it, Ashley was an anal virgin, and Vanessa was about to introduce her to the joys of butt sex.

Of course to do that she had to retrieve her strap-on dildo from its hiding place, and despite her earlier words cover it with a little lube just to make absolutely sure Ashley would enjoy this. But then Vanessa quickly returned to her friend's side and that only reinserted her finger to a positive result but managed to add a second, pushing those fingers this way and that to make sure Ashley was nice and ready to be sodomised. Maybe Vanessa should have added a third, but at that point she just couldn't wait anymore. She physically needed to take Ashley's ass, otherwise she was going to do something she regretted, like shove her dick straight up her best friend's virgin butt the second she pulled her fingers out of her.

Still, Vanessa couldn't help but take advantage of this situation, and make sure she had the best view possible for this, "Ashley, could you do something for me? Spread your cheeks. I, I know how it sounds, but it really will help you relax, and it would be so hot for me. Oh God yes Ash, mmmmmm, show me that pretty little virgin butt. You really are the best friend ever for giving me this precious gift. And I promise, mmmmmm, I'm about to make you feel so good. Even better than I did before. In fact, I'm going to make you love this so much that not only will you be a total anal whore, but you'll want to be my total anal whore. Mmmmmm, that's it baby, relax for me. Relax and give me that sexy little ass of yours."

Ashley blushed but did what she was told, pressing her face down to the bed sheets and slowly reaching back to spread her ass cheeks. She couldn't believe that she was exposing herself in such a lewd way to her best friend. Then again Ashley couldn't believe she had willingly done half the things that she had done with Vanessa tonight. This was definitely on top of the list though, and when Vanessa pulled her fingers out of her butt and replace them with her strap-on dildo Ashley initially flinched in fear. But Vanessa immediately pausing and cooing softly reminded Ashley if she was going to do this with anyone she wanted it to be with her best friend, so she forced herself to relax and stay that way as the other girl began slowly stretching her ass hole.

Feeling something knocking on her back door and then beginning to force it's way inside was scary, but when the time came Ashley had to admit there was a certain thrill to doing something so perverse. That was especially true for when her virgin back hole stretched wide enough for Vanessa's dildo to slide through it and into her before now never violated butt, meaning that her best friend had officially taken her ass cherry. Which of course made her cry out and flinch in pain, but the pain faded surprisingly quickly and left only a perverted thrill behind it, mostly because her awesome best friend stayed perfectly still and allowed Ashley to get used to the feeling of having something in her ass.

The pain returned when Vanessa eventually pushed forward again, but it was nowhere near as strong as before. If anything it was more of a discomfort, which was more or less overwhelmed by the mental pleasure of having the most private hole on her body not only being violated, but by another girl with a strap-on. Her best friend, who she loved dearly, Vanessa Hudgens was stuffing a strap-on cock up her ass, and Ashley started desperately telling herself it was only who this was, and the fact that she was a girl, which was the reason why it was feeling so good. Because that reason was embarrassing enough, but the alternative was unthinkable.

However shortly after the sodomy officially started Ashley would realise the alternative was almost certainly true, which made her whimper and even cry into the bed sheets. Which she would have been mad at Vanessa for not noticing, but as they were drowned out by loud moans of pleasure she supposed it was forgivable. Besides, she was desperately trying to avoid any sound coming out of her mouth, because she feared it would be of enjoyment. Or worse she would beg for more, because her rectum relaxed embarrassingly quickly, which could only mean one thing. She was an up the butt girl. Oh God, she was a girl who actually liked it up the butt, and Ashley had no idea how she was going to live with the shame of that. Especially if she begged for more like she almost certainly would.

Vanessa vividly remembered anally violating Ashley Benson for the first time. For so long it had been her favourite memory, even over butt fucking all those other girls. It was special to her, and always would be. But that had been forever replaced as her favourite memory the second she had started pushing her cock into Ashley Tisdale's perfect ass. She knew it would be, but during the slow invasion, and the wonderful moment she officially took her best friend's butt cherry, Vanessa was terrified that Ashley would freak out and force it to stop, and she was no longer sure she could. No, she had to convince Ashley to let her finish, because she could no longer stand the idea of not literally owning Ashley Tisdale's ass. Simply popping her anal cherry wasn't enough, she needed to make this perfect ass hers, and Ashley her butt slut.

So Vanessa went slow, slower than with any other girl she'd ever anally taken, and perhaps slower than was necessary, and as a result Ashley didn't offer up a word of protest as Vanessa stuffed her rectum full of strap-on cock. Then something weird happened. The moment her thighs came to rest against Ashley's ass cheeks, meaning that she had buried her cock within her best friend's butt and without a shadow of a doubt robbed her of her anal virginity, Ashley let out a little cry of pleasure. Or maybe that was her? Yes, it had to be her. After all, this was the moment she had been waiting for, for months or maybe even her entire life, and the alternative was just absurd.

Then after a long pause Vanessa started slowly pulling her hips back and then pushing them forwards, pumping the dildo in and out of Ashley's ass hole for the first time. Which caused Ashley to whimper in disappointment as the dick left her rectum, and then moan loudly in approval as it was returned to her hot little ass. For a moment Vanessa just blinked in amazement, then she grinned wickedly and slowly repeated the process, officially beginning to give her best friend Ashley Tisdale her first ever butt fucking. Which would have been enough to be an easy highlight of her life, but it was better than she ever imagined because despite an obvious attempt to hide it Ashley started moaning in pleasure right from the beginning.

After their first time together the other Ashley had claimed she had loved anal right from the start, that the moment she lost her back door virginity she knew she was always meant to be a total ass whore. At the time Vanessa had rolled her eyes and laughed, because while it made for an incredibly hot story there could be no way it was true. But her Ashley clearly loved this that much. Her Ashley was a total ass whore! And she was totally going to be her ass whore. Vanessa promised herself that. Well, she had promised herself that before, because again Ashley's ass was made for fucking and should be rightfully hers, but now she was more determined than ever to make her dream of turning her best friend into her personal anal slave come true.

Ashley had actually given up on trying to hide just how much she was enjoying being ass fucked, because it obviously hadn't been working. She tried to tell herself that was just because Vanessa was an amazing ass fucker, however as much as she tried to believe it they both knew it wasn't true. Well, Vanessa was an amazing ass fucker, as proven by the way she effortlessly loosened Ashley's anal walls and had her desperate to beg for more. So Ashley liked to tell herself she had been screwed anyway. But the truth was Vanessa had been right, her butt was made for fucking. Ashley knew that now. There was no other way to explain her enjoying anal sex right from the start.

The reason she was still grinding her teeth and digging her fingernails into her butt cheeks was because she was desperate to cling onto an ounce of her dignity. Ideally by causing Vanessa just lose her patients and give her the deep hard anal pounding that Ashley desperately wanted to receive, and that Vanessa  obviously wanted to give her. Although honestly at this point Ashley would just settle for not begging like a total whore for as long as she possibly could. So she held back the urge until it became literally painful, then closed her eyes, tried to make peace with the fact that she really was an ass whore, and then started shamelessly begging for what she so desperately needed.

"Harder! Mmmmmm, please fuck me harder!" Ashley whimpered, before she really got into the begging, desperately trying to tell Vanessa what she thought she wanted to hear, "Fuck my ass! Fuck my tight little ass hole! Ass fuck me hard and make me a little ass whore. Please Vanessa, you promised! Mmmmm, you promised to turn me into a total anal slut, oooooooh, and I think you kind of have , but you need to finish the job. You need to make me cum. Ohhhhhhh fuck, if you make me cum we can totally do this again. Whenever you want! Oh yeah, fuck me hard and make me your little anal slut. Yeahhhhhh, don't just make me an ass whore, make me your ass whore. Please Vanessa, make me your personal ass whore. Fuck me in the ass hard and deep until I need it like need oxygen. Ooooooh, make me crave your cock baby. Make me crave it. Mmmmm, fuck my ass so good that I'm craving it night and day, until I'm nothing but your butt sex loving lesbian slave!"

"My bitch?" Vanessa pushed, "Will you be my bitch?"

"Yes!" Ashley quickly agreed, "I'll be your bitch! I'll so be your bitch! I'll be whatever you want me to be, just make me cum."

"Then prove it. Go on all fours and start riding this dick like the little anal loving bitch you are." Vanessa ordered sternly, and then when Ashley did as she was told grinned wickedly and told her, "Mmmmm yeahhhh, prove to me that you want to be my little lesbian ass whore, mmmmmm, with a butt that was made for fucking. Prove that you want to be my butt slut, my ass whore, anal slave and whatever else I want to call you, because you're just so desperate to cum like a bitch with a nice big dick up your sexy little ass! Mmmmmm yeahhhhhh, that's it Ashley, become mine. Oh Gosh Ash, you have no idea how long I've wanted this, and now I finally have you right where I want you. Now you're finally mine. Now I finally own your fucking ass hole bitch! Ooooooh, and I'm going to use it however, and whenever, and wherever I want! Because you are mine! Ohhhhhhhhh fuck! All mine!

Without hesitation Ashley lifted herself up onto all fours and started thrusting back against Vanessa's big ass taming cock. She had to start off with a slow and steady rhythm, but she quickly worked herself up to something much more powerful than Vanessa had been giving her and soon Ashley could feel her orgasm rushing towards her. It didn't matter that Vanessa was now completely still, or that she had totally humiliated her. All that mattered was she was finally going to cum, Ashley giving up what little was left of her dignity as she moaned, whimpered and gasped in pure pleasure as she got closer and closer to the edge of her climax.

Perhaps ironically the thing that finally triggered it was that Vanessa finally start to ass fucked her again, Ashley letting out her loudest cry so far as her best friend suddenly gave her ass a hard thrust which sent her crashing over the edge of the most powerful climax of her life. As it was raising through her Vanessa started picking up her pace, triggering equally powerful orgasms which introduced Ashley to a mindless animal, slamming herself back against the new owner of her ass hole. Ashley might not have meant her words before, because she was so desperate to cum she would have said anything, but now every word was the gospel truth, and her last coherent thought for a while was that she hoped that Vanessa meant it, and that now her ass belonged to her.

Vanessa had meant every word, because this was the plan all along. To make Ashley's ass hers. To make her inner circle hers. Oh yes, Vanessa thought with a smile, she like that, and planned to tell it to Ashley. She was also ashamed she hadn't thought of it sooner. After all, what better way than to celebrate the end of the filming of Inner Circle them by destroying Ashley's inner circle? Yes, Vanessa bet the camera crew which followed them around today, and the executives at E, would never in a million years think that after that documentary Vanessa Hudgens bent Ashley Tisdale over and popped her anal virginity, violating that tight little circle, ramming her inner depths like never before, and forever turning her best friend into her personal ass whore.

More importantly they wouldn't guess that after today this would be Ashley's life. Constantly bending over whenever Vanessa wanted. Being her little anal slut. Pimping out her most private hole to her friends, co-workers and maybe even her bodyguards just for fun. Oh yes, it might take a little convincing, but Vanessa like the idea of sitting back and watching as one by one her big musclebound bodyguards butt fucked her best friend and filled her rectum full of their cum. Maybe she'd even suck it out of Ashley's ass hole. Or make Ashley shit it out and then drink it. Perhaps that could be a new party trick, before letting her friends use her personal ass whore. Most of all, Vanessa wanted to let her Spring Breakers's co-stars, which had introduced her to this fun in the first place, have they're shot with her bitch's butt.

Before those fantasies could become a reality Vanessa needed to follow the plan through and make sure Ashley came so hard and frequently that there would never be a single doubt in her mind that she was hers. Luckily thanks to Ashley again having an ass which was literally made for fucking, her Spring Breakers's co-stars, and Ashley slamming back against her like a wild animal it was probably the easiest thing she'd ever had to do. The only problem was that all this mental stimulation combined with the stimulator inside the harness bashing against her clit ensured that Vanessa came a lot too, and while it wasn't as much or as hard as Ashley it was still incredibly satisfying, and incredibly draining.

Even though there was nothing Vanessa wanted more than to butt fuck her best friend Ashley Tisdale forever she just didn't have the strength or the stamina for that. No one did, and she had to be satisfied by simply giving a good attempt, and a lot of orgasms along the way. She also had Ashley collapsing faced down in exhaustion, the only thing keeping her lower half in the air being Vanessa holding tightly to her hips, which Vanessa chose to take as a good sign. Plus it meant in that moment Ashley was literally nothing but an ass for Vanessa to fuck, which allowed her to push them both into at least one more climax each before she finally stopped.

Ashley was barely aware of Vanessa stopping and then beginning to pull her dick out of her ass. When more than usual was removed Ashley whimpered as in her delirious state she thought Vanessa was about to deliver an extra powerful thrust. Instead the entire dildo was yanked from her brutalised butt hole, causing her to cry out and then whimper in a mixture of surprise and disappointment that the fun was over. She then whimpered yet again as Vanessa pulled her cheeks apart and exposed her gaped opened back hole. If she had more energy Ashley would have definitely complained, because her ass hole felt like it resembled the Grand Canyon right now and it was embarrassing. Although it had nothing compared to what came next.

"Wow, your butt hole looks so cute when it's gaped! Mmmmm, I knew it would." Vanessa giggled as she let go of her cheeks and shuffled down beside her. Then all of a sudden her face became uncharacteristically stern as she ordered, "Now be a good little ass whore and suck my cock clean."

That woke Ashley up, and she lifted her head out of the bed sheets and exclaimed, "Ewww..."

She was going to say more, about how ass to mouth was gross and disgusting, and she would never ever do something so vile. However that monster ass fucking and the fact that her ass was now gaping open made her feel so submissive and weak, and right now Vanessa looked so strong and dominant, and above all else Ashley desperately wanted to know the joy of having the other girl's big cock in her ass again. So to her disbelief she found herself initially opening her mouth to say something, but after a long pause she just closed it, lowered her gaze, and then lowered her head to Vanessa's crotch. She then screwed up her face, closed her eyes and leaned her head forward so she could wrap her lips around the strap-on cock which had just wrecked her rectum.

What was even more shocking than her actions was the fact that she almost instantly moaned in pure pleasure. She, she actually liked the taste of her own ass. And not just like it, she instantly loved it. Needed it. Craved it. Yes, Ashley instantly wanted more, and after a few long seconds of savouring the flavour began frantically bobbing her head up and down Vanessa's dildo. Which in turn made Vanessa laugh with wicked delight, reached down and started gently stroking Ashley's long blonde hair while giving her the type of verbal encouragement which made Ashley blushed furiously in embarrassment, and yet crave more, and tell Vanessa that by looking up at her lovingly.

"Oh God, you love it! Right from the start? Fuck Ash, you really were made for this. Mmmmmm, and now you're mine. Gosh, I can't believe you're mine. Finally!" Vanessa said, "Oh Gosh Ash, I'm going to take such good care of you. I swear. I'll butt fuck you every single day I can, oh Gosh, even move my schedule around if I have too, just so I can have some of that sweet ass again. And I'll teach you to eat pussy, and ass, mmmmmm, maybe spank you when you're naughty, and most of all just constantly fuck you up the ass. Oooooh yeah, I'm gonna pound your ass all the time, and make you suck my cock clean once I'm done thoroughly gaping you, and oh, pimp you out to all of my friends. Yeahhhhh, Selena has to get a piece of this ass! Mmmmm, Rachel too. Ohhhhh, and who knows, maybe even the other Ashley will strap on one for once just to get a piece of your hot butt. Ooooooohhhhhhh, whatever it takes to make sure you remember you're mine. That you're my personal ass whore and I own your sexy little ass!"

That shouldn't have been appealing, but Ashley was so broken in that moment she found herself hoping that Vanessa meant every word of it. From the look and sound of it she did, which was good, because in that moment Ashley was nothing but her good little ass whore. More importantly her good little ass to mouth whore, something Ashley felt she proved as she shoved more and more of the dildo down her windpipe, eventually deep throating the entire length. Which was impressive, as she never sucked a cock nearly this big before, making her amazed that it had all fit up her butt. Joyfully it was true, which she was reminded of soon afterwards as Vanessa proceeded to ass fuck her over and over again until they became completely unconscious.



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