Enslaving Elliot Ch. 05

Elliot cried out softly as the finger pushed its way through the tight ring of her ass hole and slowly slid all the way inside her back door.

Just like when Jordan had fingered her ass earlier there was a small amount of pain as the finger entered her and pushed inside her, but like before the pain quickly faded. Unlike before after Jordan had spent a few moments gently sliding her finger in and out of Elliot's bottom and wriggled it around inside her rear hole the brunette pulled her finger out and then repeated this process with two fingers.

It was weird enough feeling her rectum being invaded and stretched by one finger but when the second finger was added it became so weird Elliot considered getting off the bed, grabbing her clothes and running out of here as fast as she could.

Elliot had always found the idea of anal sex gross and disgusting, and it would almost definitely hurt like hell and... well, that hole wasn't meant to be entered so it was just wrong.

Unfortunately for the blonde Jordan had made it very clear she intended to sodomise her, it had been one of the things that almost made Elliot not come here but her newly found submissive desires had been too much to resist and she had accepted this was just something she was going to have to do to get the domination she craved.

But how on earth was she going to take that giant cock in her tiny butt hole?

It had to be impossible. There was just no way it could possibly fit. Jordan would have to get a smaller toy, or better yet maybe Jordan would lick her pussy like she had done earlier. Elliot would like that. In fact she would love that.

But Jordan wasn't going to do that.

Jordan was going to be satisfied with nothing less than anal sex.

The brunette had taken a lot of anal cherries over the years and she knew just how to lube up a ass hole just right so that with enough force she could get even a dildo as big as her 12 incher up a girl's back passage. Elliot was about to suffer the same fate as many, many girls before her, not that she would suffer too much. As much has Jordan liked a little pain with her pleasure, especially when she was the one inflicting the pain, she much preferred the pleasure part, and she loved making someone take pleasure from such a perverted act, especially someone as repressed and uptight as this blonde seemed to be.

Everything was going well so far.

Jordan could easily slide her fingers around Elliot's ass hole as much as she wanted now without a negative response. In fact she seemed to get quite a positive response, the blonde moaning and groaning pleasurably as Jordan thrust her twirling fingers in and out of her back door at a steady pace, Elliot's reaction making it clear she was ready for the next step of this final act of submission.

Removing her fingers from Elliot's rectum Jordan grabbed her strap on by the base and pressed the tip against the blonde's slightly stretched out butt hole, the brunette smiling as Elliot tensed as expected before relaxing in acceptance of her fate.

Teasing her plaything like before Jordan lazily slid the tip of her fake cock up and down Elliot's ass crack for a few long moments before pressing the dildo firmly against the puckered opening.

"You haven't ever taken a cock up your ass before have you stick?" Jordan asked, already knowing the answer but wanting to hear it from the blonde's lips.

"N... no Mistress." Elliot whimpered.

"Good, I love popping anal cherries, and this way your first time taking it up the butt is even more special because it symbolises your submission to me." Jordan said, pausing for a moment to let that sink in before continuing, "Now, I want you to reach back and spread your butt cheeks for me stick. Open yourself up and offer me your ass hole. Make it easier for me to take your anal cherry."

Elliot whimpered, but did as she was told, pressing her face into the bed sheets as she reached back and spread her butt cheeks, offering her virgin ass hole up as a sacrifice to prove her submission.

Jordan smiled at this proof of submission, before pressing forward slowly but firmly, watching with glee as the tight puckered opening spread around the head of her dildo until it was finally slid through Elliot's tight back door, popping her anal cherry.

Elliot gasped in a combination of surprise and pain as Jordan robbed her of her anal virginity. She hadn't thought it was possible for something so big to fit inside her tiny butt hole and as pain shot through her body she wished she had been right.

Luckily the pain was given a chance to slowly fade away as Jordan stayed as still as a statue for a few moments before forcing an additional inch into Elliot's rectum.

With every additional inch Elliot either gasped or cried out, the blonde digging her fingernails into her buttocks and clenching her teeth as she endured one of the most painful experiences of her life.

"Oh don't be such a little cry baby stick." Jordan said, smacking Elliot on her half filled ass, "Suck it up and take it."

Wanting to complete this task so she could be officially Jordan's slave Elliot did as she was told, her teeth grinding together almost painfully and her fingernails digging so deeply into her butt cheeks they almost drew blood as she tried to remain quiet while having her ass forced open and stretched wide.

It seemed like it would never end, inch after inch going up Elliot's butt, with every inch Elliot swearing she couldn't possibly take any more only for Jordan to prove her wrong and force another inch into her back passage.

Just when she thought it would go on forever Elliot felt something press against her butt cheeks and after a few seconds she realised to her amazement it was Jordan's thighs meaning somehow that 12 inch dildo was now all the way inside her ass.

"Congratulations twinkie, that's 12 inches all the way up your butt." Jordan praised mockingly with a hard slap to Elliot's full to bursting behind, "How does it feel?"

"Gr... great Mistress." Elliot lied through her teeth.

"Ha, well don't you worry stick, I know your type. You say butt sex is disgusting and you'd never do it but one good session of ass fucking later and you're a little anal whore." Jordan said after the blonde's obvious lie.

"Hm." Elliot snorted, before quickly trying and failing to find the right words to apologise, "I mean if you say so Mistress... I mean whatever you say Mistress... I mean... I mean, yes Mistress."

As Elliot whimpered in anticipation of a beating for her little slip and the words following them Jordan briefly considered punishing her pet but decided to save it for later, right now she wanted to finish breaking in her new slave.

"You're right stick, I say so. I say you will end up loving it up your butt, and you will, but for now just try to relax. Your Mistress is going to start fucking your ass now and it will be easier for me if you try and stay as loose as possible." Jordan informed her little bitch as she tightened her grip on Elliot's thighs and began slowly pulling her strap on from the blonde's butt.

Elliot cried out as she felt the truly bizarre sensation of Jordan's dildo slowly being removed inch by inch from her rectum until it was about halfway out at which point the brunette stopped and began pushing her strap on back inside Elliot's ass.

Jordan repeated this, beginning a slow rhythm, her dildo moving steadily through the blonde's back passage, stretching it out for what would come later.

Elliot's mind wasn't focused on what was going to happen later, it was very much focused on what was happening right now.

Having something moving in and out of her butt was by far the weirdest sensation of Elliot's life, although surprisingly not the most painful.

Elliot had expected this to be like pure agony, but even during the initial entry it wasn't anywhere near as painful as she had been expecting and surprisingly the pain she felt quickly deteriorated into a dull, uncomfortable ache. It was still far from pleasant but it wasn't unbearable either. If this was as bad as it got the blonde could definitely take it if it meant she could be Jordan's slave and know the sweet submission she had felt with this dominating woman everyday.

Just as Elliot began to think she could put up with this something amazing happened.

She felt a spark... a little spark of pleasure... coming from her ass hole!

But that was impossible. It had to be impossible.

Sure Elliot had thought she had felt pleasure from her butt hole before when Jordan had fingered her ass in one of the patient rooms, but over the last couple of hours she had concluded that she had to be imagining things because there was no possible way she could ever feel pleasure from that hole.

Nearly the exact same moment Elliot thought that she felt it again, and then a short time later again, and then again, and then again, and then again.

Soon the sparks came quicker and got stronger, Elliot's body filling with pleasure which shouldn't be possible but apparently it was.

As those little sparks became bigger, stronger and faster Elliot's ass hole slowly seemed to loosen around the invader until even the uncomfortableness disappeared, leaving only the sparks of pleasure which eventually became so strong Elliot couldn't stop herself from moaning in pleasure.

Elliot's eyes almost burst from her head when the first unmistakable moan of pleasure fell from her lips. It couldn't possibly be feeling that good, could it? Apparently it could as moan after moan escaped her mouth.

Soon much like earlier when the butt sex began Elliot gritted her teeth and buried her face into the covers, only this time it wasn't to try and drown out her cries of pain but to cover up her moans of pleasure.

The feeling of humiliation for enjoying something so gross and disgusting was so overwhelming tears of shame filled Elliot's eyes and stained the bed sheets but she didn't complain, instead she just stayed there on her knees with her face down and ass up, her hands submissively spreading her butt cheeks for her new owner as she wept, cried and moaned as her body betrayed her.

Jordan smirked as her new little pet began moaning for her, a clear sign the blonde was beginning to like it up her butt.

The brunette had meant what she said before, she had seen Elliot's type and knew it wouldn't take a lot to make this uptight little bitch an anal loving whore.

Sexually repressed people like Elliot were easy to pervert, because without a steady dose of good old fashioned sex their minds were left to wonder and more often than not some of the more kinkier sides of sex became all they could think about. Things such as same sex fun, anal pleasure and fun with toys were the most common, all of which would then be repressed by the uptight person who thought about them during lonely nights.

There was a very good chance that Elliot had thought about girl on girl fun and anal sex during her alone time but then had been so ashamed about it that she repressed it. If that was true then Jordan was doing Elliot a favour by showing her there was no need to be ashamed of things which felt so good.

Of course there was the chance Elliot was just a straight girl who was genuinely disgusted by butt sex, but if that was true Jordan really didn't care. In fact Jordan liked the idea that maybe Elliot was an anal hating straight girl who she was turning into an anal loving dyke. Well, technically a anal loving bisexual, but anal loving dyke seemed hotter for the situation.

Whatever the case Jordan was having a lot of fun introducing Elliot to the joys of anal sex.

There was just something about butt fucking another woman which really turned Jordan on, especially in this position.

It just made Jordan feel so powerful, so dominant, so in control.

At this moment she had another woman in one of the most submissive positions possible, face down and ass up on her bed, the blonde still spreading her butt cheeks because Jordan hadn't told her to stop, the brunette kneeling behind Elliot and gently thrusting her strap on in and out of her ass.

From this position there could be no doubt who was in control, no doubt who was in charge, no doubt who was the mistress and who was the slave.

The position also gave Jordan a great view to look at while she butt fucked her slave, that being of course her little bitch bent over and spreading her ass cheeks for her, exposing her cute little butt hole as it was being destroyed by her strap on.

To Jordan the blonde's ass hole looked beautiful, stretched wide open by her toy in total submission to her, that busted up butt hole letting Jordan know it understood she was it's new mistress, she owned it and could do this to it whenever she wanted.

Elliot herself was being just as submissive as her ass hole, the blonde exposing her wrecked rectum to the woman who owned her butt hole and every other hole on her body.

The moaning and crying was another nice sign of Elliot's submission, but Jordan found herself wanting more, and sliding one of her hands from the blonde's thigh down to her pussy Jordan found the more she wanted.

"Looks like I was right about you doesn't it stick?" Jordan said as she lazily stroked her fingers up and down the lips of Elliot's soaking wet pussy only to pinch the blonde's clit tightly when she didn't get a response, "Doesn't it?"

"Yes Mistress!" Elliot yelped in pain, pulling her face from the covers and turning it so she could speak to her mistress, "You were right about me."

"So what does that make you twinkie?" Jordan asked.

Elliot thought about this for a few moments and then whimpered once she realised what she'd have to say.

"A... a little anal whore Mistress. It... it makes me a little anal whore." Elliot mumbled.

"That's right, good girl." Jordan said, letting go of Elliot's clit and going back to gently stroking the blonde's pussy, "You're a little anal whore. My little anal whore. What are you?"

"Your... your little anal whore Mistress... owww!" Elliot exclaimed as Jordan smacked her spread ass cheeks, connecting mostly with the soft flesh of her bottom.

"Again, but this time without the annoying hesitation, what are you?" Jordan demanded.

"Your little anal whore Mistress, I'm your little anal whore." Elliot replied quickly.

"Good girl." Jordan said as Elliot whimpered again, "Oh, why are you crying stick? Does it still hurt? No, your moaning too much and your pussy is too wet for it to still hurt. I know, you're crying because you can't believe how good it feels, and you're a little ashamed for liking it so much, isn't that right stick?"

"Yes Mistress." Elliot said in a voice barely above a whisper.

"Why do you feel ashamed to like it stick? Tell me." Jordan ordered.

"Because it's gross, and disgusting, and wrong, and... and... it shouldn't feel this good." Elliot blurted out, a fresh batch of tears falling from her eyes.

"Oh don't worry about that twinkie, what you're feeling is natural for a girl like you." Jordan said, comforting Elliot in her own unique way as the blonde continued to whine, "Do you know what your problem is stick? It's that you think of yourself as a woman, when the truth is you're not, not really. A woman has dignity, self-respect, and power. You have none of these things, because you're not really a woman. You're a weak, pathetic little slut. But don't feel too bad about it twinkie, it's just your place in life. You exist so real women like me have something to compare ourselves too, something to try not to be, and most of all something to use for our pleasure. You see stick, you were born to be the sexual plaything of real women and your entire life you've just been waiting for someone like me to take you, break you, and turn you into the little slut you were always meant to be. Deep down you know that I'm right, that whenever you tried being a strong woman, a real woman, it just never felt right and you just ended up failing and being a disgrace to our gender. But today when I dominated you it felt right didn't it stick? It felt right, natural even, because you were where you were supposed to be. You had been put in your place and you loved it."

Jordan paused in her little speech so Elliot could whimper and take that in before continuing, "I'm not saying this to be mean stick, I'm just stating the facts, and if you search your heart you'll realise it's true. You don't have too admit it right now, you just have to think about it while I'm enjoying your ass. Speaking of which, let go of your butt cheeks and lift yourself up onto all fours, it's time for me to show you just how good a nice hard ass fucking can be for a little slut like you."

Elliot whimpered but didn't hesitate to obey, letting go of her ass cheeks and pushing her upper body upwards so she was on all fours. She then braced herself, deeply fearing what would come next, although it wasn't what she was expecting.

From Jordan's tone of voice Elliot had been expecting her new mistress to start jack-hammering her poor ass hole with all her might but instead Jordan just ever so slightly increased the pace, waited a while and then slightly increased the pace a little more, and then another pause followed by another increase in pace, Jordan repeating this process until finally she was jack-hammering in and out of Elliot's ass hole.

If Jordan had immediately started pounding away at Elliot's pooper then it would probably have torn the poor blonde's butt hole apart. Considering the power Jordan was now using to butt fuck the blonde doctor Elliot's ass hole should have been torn to shreds, and maybe it was being torn to shreds, but if it was Elliot couldn't feel it, she couldn't even feel any uncomfortableness, all she felt was pure pleasure coming from her butt.

This wasn't like before either because instead of little sparks rocket seemed to be exploding inside her caboodle and then shooting straight from it to her brain and then threw out her body, driving her crazy.

Elliot had heard it was possible to receive stimulation from her butt hole. She had always dismissed it as impossible but as her mind melted from anal pleasure there was no way she could possibly deny it now.

It felt so good Elliot wasn't even sure stimulation did it justice.

It was so amazing it actually felt as good as when her pussy was being fucked... maybe even better, which just made Elliot even more disgusted with herself.

It wasn't natural, it didn't feel natural, but at the same time it did. It was a paradox Elliot struggled to understand, part of her hating herself for getting such unbelievable pleasure from something she had always considered so disgusting and yet another part of her too deliriously happy to care.

The part of her that was deliriously happy tried to ignore the other part, Elliot wanting to just shut off her brain and enjoy the pleasure she was feeling but there was a thousand different thoughts screeching through her head like a deafening siren, taking away from her enjoyment until finally she had an epiphany, a moment of perfect clarity which set her free, not just to enjoy anal sex but to accept who she really was.

She was a slut. She wasn't a woman, not a real one. She was just a slut.

She didn't deserve to be called a woman. She was a disgrace to her gender. She should publicly apologise to every woman in the world for trying to impersonate one of them when the truth was she was nothing but a little slut who should be bowing down to the real women of the world. Real women like Jordan Sullivan.

Oh Jordan. Her wonderful mistress. A real woman who had seen her pathetic attempt to impersonate a woman and had put her in her place.

Jordan had shown Elliot what she truly was, a slut.

A woman wouldn't enjoy something so revolting as anal sex. A real woman would be disgusted by it, think it was unnatural, and not enjoy it in any way if she had to endure it.