Dawn’s Anal Awakening

A/N: Hi to all my beloved readers! Surprise! I’m alive! (Actually, I’m surprised I’m alive too, didn’t expect to make it this far in a pandemic)

Some people have asked and yes I do intend to finish this story but between losing one of my jobs, sudden onset of a hereditary disease, and being unable to graduate cause the university is an ass, I’ve been unable to find time to really sit down and write so I’m not sure when the next installment will be. But I’m glad that y’all are sticking around! Your comments are what keeps me writing!

As always, proper communication is key in any relationship, don’t try to stuff your partner’s peehole without asking. This is fiction so it doesn’t matter but in real life, please discuss these things with your horizontal tango partner.. :>

Also, remember to hydrate and stay safe, pornossieurs!

8=====D ( );( )

Dawn moaned around the gag in her mouth, writhing on the bed as Kennedy, her girlfriend, lovingly worked her fist into Dawn’s anus. Try as she might, she couldn’t make Kennedy go faster, not when Dawn’s wrists were secured to her ankles with leather cuffs.

Ever since the first time Kennedy pushed her whole hand into Dawn’s ass, Dawn had been hooked on the sensation of having her shithole split wide open by a fist. If you told her a year ago that she would swiftly turn into an anal-loving slut who cherished the feeling of cock pumping sperm into her young shithole, she would have laughed in disbelief.

But here she was, just a week shy of 19, a fully-fledged cock-loving anal slut in a loving relationship with a lesbian who loved to make Dawn scream with anal pleasure.

After her hot older neighbour had fucked multiple orgasms out of Dawn’s teen asshole, something in her had changed. Or rather, something in her had been revealed. It took some time, but she was now completely secure in her identity as an anal whore.

Dawn loved it. She loved who she was, who she had become – a young girl who would stop at nothing to get her rectal passage filled and stretched and pounded by all sorts of cocks and toys.

“I love watching you like this,” Kennedy said with a fond smile. Her forearm was buried inside Dawn’s pert backside, all the way up to the elbow. The fluid coating her arm wasn’t lube, but rather Dawn’s cunt cream. There was so much of it that Kennedy had barely needed to add a couple of pumps of commercial lube before sliding her fist into Dawn’s hole.

The orifice in question had been pink and puffy, but was steadily turning red from the friction of Kennedy’s arm sliding in and out. It stung a little, but the depths of Dawn’s anal depravity were much deeper than most. She loved the ache of being stretched too far and she loved the soreness of a chafed asshole. It made her feel submissive and well-used.

It was just as well, because her girlfriend, Kennedy Harper, loved ruining the assholes of young girls, forcing them open, fucking them raw, gaping them, watching the girls cry from the pleasure and pain of being anally destroyed. Her previous girlfriends had never been able to fulfill that sadistic part of her, but Dawn could.

Dawn was an anal sadist’s dream come true, a girl who would willingly spread her asscheeks, beg for a rough drilling, then obediently slide her training plugs back into her abused hole for a good stretch. She loved being reminded of her slutty ways by the ache in her shitter.

Kennedy delighted in making sure the reminder was refreshed every single day, either by herself, or the many boys willing to double, triple, quadruple team Dawn’s eager holes.

In the past, Kennedy might have gotten jealous if her girlfriend wanted to fuck other men. But Kennedy knew that Dawn had certain needs that a girl couldn’t fulfill. Needs like a shot of hot cum deep inside her holes, or on her beautiful face and tits. The extent of Dawn’s anal cravings wasn’t something that Kennedy wanted to keep to herself. She particularly loved watching her blonde girlfriend get anal gangbanged and pumped full of cum, because then Kennedy could take her home and then fuck all the cum back out of her using her largest strapon. Dawn would take it, she loved it. She loved getting cum fucked into her, and she loved getting the cum fucked out of her. And since Dawn’s body had already associated rectal pain with pleasure, it would cum again, and again, and again, whether Dawn’s mind wanted to or not.

“Mmmmmph,” Dawn moaned around the gag. She strained against her restraints, wanting to caress the bulge in her flat stomach that came from Kennedy’s fist, but to no avail. Kennedy wished she could take off the gag and let Dawn squeal and moan as she pleased, but there had been one too many noise complaints and Kennedy didn’t want to risk getting kicked out of the dorms.

Now, Kennedy refused to give Dawn any orgasms unless the blonde was well and truly gagged.

Their collection of gags had started with the one that Eric, Dawn’s neighbour, had sent as a present. It then expanded to several sizes of penis-gags, and O-rings for skull fucking.

“Mmm Mmmm mmmmm!” Dawn whimpered as Kennedy roughly punched her arm in and out of the abused hole. She watched in fascination as the rim of Dawn’s anus was pulled slightly outwards by her arm. Her asshole was starting to develop lips, the mark of a true anal-whore. Kennedy felt a strange sense of pride because she had been the one responsible for Dawn’s ruined asshole!

Kennedy pulled her arm out all the way just as Dawn was about to have an analgasm.

“Nuh uh,” Kennedy tutted “Not yet,” she smiled at Dawn’s moan of frustration. It was a Saturday and they had nothing to do except push Dawn’s masochistic and submissive limits.

Kennedy reached for their toy box. She had been talking to Eric here and there, informing him of Dawn’s sexual developments. He had sent along even more toys, addressed to Kennedy this time, telling her to use them on Dawn. Kennedy had been jealous of Eric at the start, the older man having been the one to fuck Dawn’s inner anal slut out of her. As time passed, she realized that they weren’t rivals, but rather allies whose only goal was satisfying Dawn’s anal needs and expanding her sexual horizons. One of the avenues that Kennedy was intent on exploring was how much Dawn really trusted her, and how far Dawn was willing to go.

The brunette pulled out a few toys and set them on the floor so that Dawn wouldn’t be able to see what was happening.

First, she took a piece of twine and wound it around Dawn’s clit. The little love nub had been subject to a lot of abuse throughout their relationship, though not as much as Dawn’s ass. While clit-torture alone didn’t do much to make Dawn cum, having her clit pulled, twisted, pinched, or spanked while Dawn was being pounded in the rear made her cum harder and longer. It was as if her clit was a switch connected to her shithole that made her cumgates open!

The rough twine scraped across the sensitive flesh, making Dawn whimper in pain. Kennedy wound it around her clit several times and then tied a little bunny knot on top of it with a giggle. It looked like a precious pink pearl that invited fingers to flick it and tease it.

Then, Kennedy took out a silver case. This was one of her late-night purchases that she made when Dawn was all cummed out. She opened the case to reveal six pink silicone rods of varying thickness.

Vibrating urethral sounds. Kennedy had always wanted to try it, but her exes had never dared. With Dawn, Kennedy wanted to know if her little girlfriend was as much of a slut as she thought, if her young holes were all wired for pleasure like Kennedy suspected.

Kennedy lubed up the thinnest rod and tugged on the string on Dawn’s clit, lifting it up and out of the way. Dawn squealed as the string tightened, cutting off blood flow to her sensitive glans, making it swell into an angry red colour. Kennedy grinned at her and gave it a flick, laughing when Dawn yelped in aroused pain.

“Take a deep breath and relax, slut,” Kennedy said affectionately. Dawn did as she was told. Kennedy pressed the slim sound into her peehole. Dawn made a sound of surprise, but her pisshole, like her other holes, could not resist being penetrated and stretched. The sound made its way in slowly but surely. Dawn moaned in pain and arousal, her urethral muscles twitching as Kennedy forced it open with her silicone toy.

Kennedy fucked Dawn’s smallest hole gently, pushing the toy inwards a little at a time.

As she suspected, Dawn was the kind of slut who welcomed penetration no matter the hole. She moaned and sighed and whimpered as the sound was forced deeper and deeper and deeper until… the wide base nudged up against her pisshole.

All six inches of the sound was buried inside Dawn’s urethra, reaching far back into her bladder.

Kennedy switched on the toy, watching it come to life in Dawn’s pisshole.

“Mmph, mmmmpph!” Dawn screamed behind her gag, hips thrusting back and forth. Kennedy yanked on the string attached to her clit in warning. Dawn screamed louder as her clit was abused, but then managed to still her hips. She lay there, helplessly restrained, as the sound massaged the insides of her urethra.

Kennedy grinned at the sight of the squirming girl. She grabbed some electrical tape and secured the vibrator to Dawn’s inner thigh, then sat back to watch.

Dawn squirmed and moaned and whined and whimpered as her previously untouched pisshole was stretched and vibrated to the point of breaking. It was made worse by the fact that she hadn’t been to the toilet for hours. Not to mention her clit had swollen up from the string Kennedy had tied around it. The vibrations from the toy in her urethra felt as if they were placed directly on her aching clit, making it twice as painful.

Most people would not have been able to become aroused when they were being tortured like this. But Dawn was not most people. Her masochistic side was being teased out more and more under Kennedy’s tutelage. The pain in her most sensitive area was, logically speaking, a turn off. However, her body didn’t follow that logic. Kennedy loved to twist and pinch and pull her little clit when Dawn was on the brink of analgasm. Her body had long since began to associate clittoral pain with powerful orgasms, so it was no wonder her young cunt interpreted it as pleasure and pushed out waves of slick in response to the torture meted out on her pisshole and her clit.

Kennedy grabbed a vibrator and sat down next to Dawn. She pushed her vibrator into her own drenched cunt, letting Dawn see just how it parted her pussy lips and disappeared into her nether regions. Then she slid it back out, slowly.

Dawn moaned. She loved watching Kennedy fuck herself as well. She desperately needed a cock in her asshole or her cunt but Kennedy wasn’t going to let her have that satisfaction just yet! No, Kennedy toyed with her own bald pussy at a torturously slow pace, reaching over to flick Dawn’s tortured clit from time to time to make sure Dawn was feeling the burn in her hole.

“You look absolutely gorgeous like this,” Kennedy told Dawn, relishing the sight of Dawn’s curvy body writing on the bed, “Clit all tied up like a present, just begging for a little pinch!”

She punctuated her words with a rough twist to Dawn’s poor clit.

“MMMMPRHPH!” Dawn squealed behind her gag, shaking violently all over as the pain ripped through her sensitive nub! Slick gushed from her well-trained cunt.

“Pwese, pwese!” Dawn begged. At this point, she didn’t know if she was begging for more or for Kennedy to stop. Each pinch of her clit was like a stabbing pain between her legs but it was swiftly followed by wave after wave of arousal, stoking the heat in Dawn’s belly. She was pretty sure that if her pisshole wasn’t plugged up with the vibrator, she would have pissed herself by now.

As it was currently stuffed full with a silicone sound, Dawn couldn’t pee even if she tried! Instead, she was forced to endure the fullness of her bladder, made worse by the way the sound was massaging every inch of her tightest hole.

“How does it feel?” Kennedy asked with a pleased grin. Dawn could only moan in response.

“I’m going to stretch your pisshole too, I’m going to stretch it nice and wide until it can take my fingers, maybe even a strapon. What do you think about that?”

Dawn shivered in arousal and fear. Her peehole was definitely not meant to take something of that size, but the same could be said of her asshole and it had been swiftly trained into taking massive toys, not to mention Kennedy’s entire arm. With practice and persistence, it was possible that Kennedy could do exactly as she said and teach Dawn to enjoy peehole fucking as well.

“Look at you, you’re such a slut,” Kennedy said affectionately. She flicked Dawn’s love nub again, drawing a muffled squeal from the younger girl. “I mentioned sounding to my ex once and she broke up with me the next day. But you? You didn’t even try to close your legs when I slid all six inches of it into your pisshole on the first go. And you didn’t even flinch when I said I wanted to put my strap in it eventually.”

Dawn blushed, unable to deny the fact that the idea of being trained to take cock in every single hole was making her pussy twitch and tremble. What would it be like? To have Eric press his hips against hers and feel all 10 inches of him filling her pisser? What would it feel like to have his hot cum pumped into her bladder.

She let out a soft moan at the thought. He had always been supportive of her slutty adventures, as evidenced by the many toys he sent her and Kennedy. Would he be proud that she had dedicated her last remaining hole to taking cock too? Maybe he would make love to her pisshole the way he did to her ass.

Her empty pussy and shithole twitched hungrily in response to her fantasies.

“Pweeease!” Dawn begged. Her teen cunt was soaked with her juices and she was teetering on the edge of orgasm but there was something missing still.

Kennedy took pity on her poor anal-loving slut of a girlfriend. She slipped the vibrator out of her own bald pussy and then pushed it all the way into Dawn’s twitching cunt in one swift stroke, stretching out Dawn’s tight hole.

Then, with one hand on the Dawn’s clit and the other poised at Dawn’s shitter, Kennedy pinched and twisted Dawn’s poor abused nub as she slowly and surely forced her fist into Dawn’s aching asshole!

“MMMPH! MMMPGH!!!!” Dawn all but screamed behind her gag.

Pain and pleasure crashed through her body at the same time, the waves of each threatening to drown out the other.

On one hand, the twine around her clit and the constant pinching had made it incredibly sensitive and sore. But on the other hand, her lonely asshole was finally being filled by her beautiful girlfriend’s arm!

The neglected walls of Dawn’s rectum sang with joy, welcoming Kennedy’s forearm eagerly as the brunette pushed her hand and wrist inside. The pressure of being filled felt like the final piece of a puzzle sliding into place. This was what she missed, the constant fullness of being anally filled!

“Go on, cum!” Kennedy crowed gleefully, yanking the twine off of Dawn’s sore nub.

“MMMMMRPH!”

The bite of the rough material on Dawn’s most sensitive organ and the sensation of Kennedy’s arm buried in her asshole sent Dawn crashing into a powerful orgasm. Her hips trashed from side to side as waves of pleasure swept over her and zapped every nerve with zings of electricity.

Her pussy clamped down on the vibrator, milking it as if it were a real cock, begging for a dose of hot cum. Her ass clenched on Kennedy’s arm, her velvet insides squeezing and convulsing repeatedly.

Kennedy bent her head to Dawn’s poor abused clit and sucked on it hard, using her lips to nibble the flesh there.

“NMph Mmpgh!” Dawn shook her head wildly as a second orgasm took her whole body hostage.

The sharp agony from Dawn’s sore organ made her muscles clamp down harder on Kennedy’s arm and the vibrators in her holes, which in turn made every single sensation intensify into blinding waves of pleasure.

All of her holes were filled. Her mouth with the gag, her pisshole with a vibrating sound, her pussy with a vibrator, and her ass with Kennedy’s arm. Any other person might have been alarmed, shocked, or fearful, but Dawn was none of those things.

Instead, Dawn was overcome with bliss and enlightenment. This was how she was supposed to be – a set of holes to be stuffed full of cock, a toy to amuse Kennedy!

Dawn’s helplessness, suffering, and pleasure at the hands of her dominant girlfriend didn’t just feel good, it felt right.

Dawn wasn’t just an anal slut, she was a masochistic submissive anal slut and she loved it.

She moaned at the realization, the knowledge that Kennedy could suggest anything and Dawn would go along with it because she was a masochistic submissive anal slut who loved being stuffed airtight and creamed repeatedly until she was a sloppy, oozing mess of cock-and-cunt juice.

The electricity that zinged through Dawn’s limbs slowly ebbed. The aftershocks of her two powerful orgasms made her twitch and tremble helplessly in her restraints.

Kennedy tenderly slipped her arm and the pussy vibrator out, setting the toy on the ground. She turned the vibrating sound off, but left it buried in Dawn’s peehole. It wouldn’t do to remove it this early if her goal was to get Dawn used to urethral penetration. Instead, Kennedy set about releasing Dawn’s from the leather cuffs.

Dawn’s limbs were jelly from how hard she had cum. She could only lie limp on the bed as Kennedy wiped the both of them down.

“Turn over,” Kennedy instructed.

Dawn flopped onto her belly with a soft ‘oof’, knowing what was going to happen next.

She reached back and spread her asscheeks wide, showing off her puffy rim.

“Good girl,” Kennedy praised her, “That’s my good little anal whore.”

There was the sound of a buckle, a moan from Kennedy, then the blunt head of Kennedy’s favourite strap nudging up against Dawn’s stretched out asshole.

Dawn whimpered, her body quivering with anticipation.

Their recent fucks had all been like this, Kennedy edging Dawn in many different ways until Dawn was nothing more than a shivering wreck, followed by Kennedy roughly fucking Dawn’s asshole with her strap until she was satisfied.

“What do you say?” Kennedy teased her.

“Psh fk mah assh,” Dawn begged obediently, her tongue working around the gag.

Orgasm or not, sore or not, it never felt right to have her shithole empty.

“Good girl,” Kennedy praised as she pressed the tip of her strap against the red and puffy hole.

It slipped in with only the barest resistance since Dawn had been fisted earlier. Kennedy wasted no time in slamming her hips forwards and burying the entire thing in Dawn’s eager hole.

“Moh!” Dawn let out a muffled, aroused, yelp as her hole was filled yet again.

“Your slutty hole is sucking the strap in, Dawn. If only you can see the way it’s begging for cock. Your shithole was meant to take cock, wasn’t it?” Kennedy said, a huge grin on her face as she started to fuck Dawn’s ass in earnest.

Dawn, exhausted from her earlier orgasms, could only whimper her agreement.

“Ysh imma hore, a tnnaged cck lvin anal swut!” Dawn panted as Kennedy railed her anal passage roughly.

Despite her tiredness, Dawn still managed to grip her plump asscheeks tightly and spread them wide apart so that Kennedy could drill into her rectum.

Each slap of Kennedy’s hips against Dawn’s was accompanied by a loud squelch. Dawn’s pussy never seemed to run out of slick, which suited her just well. It meant that anyone could fuck her no matter the time or location because her cunt cream provided more than enough lube.

“You’re so wet, always so wet,” Kennedy marveled, pleased at knowing Dawn loved having her asshole drilled in such a callous manner. Seeing the younger girl so fucked out like this, yet still doing her best to hold her ass wide open so that Kennedy could abuse that puffy hole, it filled Kennedy’s heart with warmth and happiness.