Ashley's Inner Circle

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.