Dawn's Anal Awakening Ch. 05

Dawn was very pleased with herself.

Her first semester at Wheaton College was progressing very nicely. Her classes were all introductory and with a bit of time in the library, it wasn't difficult for her to get decent grades. She got along with her coursemates, and she enjoyed the newfound freedom of living away from her parents.

Particularly the freedom to fuck as many cocks as she wanted, whenever she wanted.

Dawn, 18 year-old anal slut extraordinaire, was insatiable when it came to ass-fucking. Her roommate, Kennedy the dominant lesbian, was more than happy to indulge the blonde teen's anal desires.

The fateful first meeting had set the tone for their future interactions, which was to say that Kennedy had no holds barred access to Dawn's rectal passage and was in charge of Dawn's anal wellbeing. It was a duty that Kennedy took very seriously.

Every morning, Dawn would get up at 7 and then start eating out Kennedy's pussy while the older girl slept. She would lick and suck and lap until Kennedy woke with a squirting orgasm. Dawn would swallow every single drop of Kennedy's girl cum, sealing her lips over Kennedy's piss hole until the older girl finished her orgasm.

Kennedy, awake and rejuvenated from a good morning cum, would then pull out her strapon and bend Dawn over the side of the bed for a good anal reaming.

To think, Dawn had been worried that she wouldn't get good anal sex in college! She was living with a lesbian brunette who loved to inflict hardcore and intense ass-fucking on the assholes of young girls like Dawn!

Kennedy was living a real-life fantasy. She had been hurt, angry when her ex had suddenly broken up with her and moved out to fulfill her dreams of becoming a star. But then, the teenaged Dawn Simmons, with her perky tits, bouncy ass, and deep-seated love of anal had moved in.

Somewhere, somehow, the stars had all aligned and whatever deities out there had seen fit to provide Kennedy with a younger roommate whose anal lust far outstripped Kennedy's own. While the brunette did enjoy a nice hard anal drilling from time to time, she much preferred being the one doing the drilling instead.

The sight of Dawn, panting as she spread her buttcheeks and struggling to take Kennedy's strap-on, would forever be burned into Kennedy's psyche.

And that was just the beginning.

Dawn had taken Kennedy's instructions easily, obeying the brunette with little to no complaints. Kennedy forbade her from anal for three days, and Dawn had obeyed, albeit reluctantly. When Kennedy ordered her to show up to an unknown location, Dawn had also obeyed quickly.

The blonde girl had dropped to her knees for two strangers' cocks without a moment's hesitation, based purely on Kennedy's instructions.

That was an intense power trip for the older girl. None of her exes liked being ordered around but Dawn seemed to welcome it. Kennedy thought she might have pushed past Dawn's limits by torturing the poor girl's clit while she was still cumming from the rough double penetration of both nether holes by Maxwell and Winston's hard cocks, but Dawn had blown Kennedy's expectations out of the water by cumming even harder! She wasn't just an anal slut, Kennedy was coming to realize, even though anal made Dawn cum the hardest, Dawn just liked fucking. She loved cock, she loved being split open, and pain on her clit, or her tits, or her shithole, it all made her cum harder.

Dawn loved to be used, and used hard.

It didn't matter whether the cock was silicone or otherwise, as long as it was fucking into one of her holes, the blonde girl was happy.

Kennedy pondered this, wondering how to work this into their future shared sex life. The younger girl wasn't going to be satisfied with just Kennedy, and the twins weren't always going to be available.

The brunette tapped her lips with her fingers. Well, the twins were throwing a party this weekend...

RAP RAP RAP!

Kennedy blinked, surprised by the knocking at the door.

"Delivery for Miss Simmons!"

Kennedy opened the door. The delivery man gave her a bored look and handed her a fairly large package.

"Here."

"I'm not-"

"I don't care, you're her roommate right? Just sign." The delivery man shoved the pen and clipboard into Kennedy's face.

Kennedy scowled, but signed it and shoved it back anyway.

She brought the package in and closed the door behind her.

"Who was it?" Dawn asked, coming out of the shower. She was damp, her hair up in a bun, towel held loosely around her waist, her 32C tits bare in the cold air.

"Delivery for you," Kennedy said, setting the package down on Dawn's bed.

"Oooo!" Dawn squealed. She bounced over, her tits bouncing as well, Kennedy was mesmerized by the way her flesh jiggled and quavered.

"It's from Eric!" Dawn exclaimed. She started ripping open the paper.

Kennedy couldn't help but feel a spike of jealousy. Eric had been the one to awaken the anal slut in Dawn. He had been the one to introduce Dawn to the joys of cock and the pleasures of being fucked silly over and over and over and over again. Kennedy wished she could have been there to see the first expression of wonder on Dawn's face as the blonde girl had her very first intense orgasm.

"Oh my god!" Dawn said softly in shock and awe. She reached into the box and pulled out ...

... two double headed dildos

... bejeweled anal plugs

... anal beads

... two remote-controlled vibrators

... leather cuffs

... a blindfold

... a penis shaped gag

... three suction cup dildos of different shapes and colours

... and a bottle of lube.

"There's a note!" Dawn breathed, pulling out the piece of paper and reading it aloud.

"Dear Dawn, I've been missing the feel of your tight holes on my cock. I must thank you for telling me all about your lesbian encounter and the double penetration experience you had. I wish I had been there to witness it. I'm relieved to know that you've found someone who can give you the anal drilling you so truly need while you're in college. Although I can't be there for you, I still want to make sure you're sexually satisfied in every way. These are gifts for you and your roommate to enjoy. I've included a gag because I know you are really loud. I hope that you're being considerate about the neighbours. Much love, Eric."

Kennedy couldn't help but stare open-mouthed at the multitude of sex-toys that had just been delivered to their room. Eric was really invested in Dawn!

"I've never had a chance to try this," Dawn said slowly, picking out the double-headed dildo. She gave Kennedy a shy look from under her lashes.

Despite reaming Dawn's ass on a daily basis, despite seeing the blonde undressed and screaming from orgasm after orgasm, Kennedy still felt flustered at being propositioned for a double dildo session with Dawn.

They hadn't scissored yet, even if they had eaten each other out. It was one of the most intimate things lesbians did, and Kennedy didn't often do it with her exes.

Dawn pushed all the toys aside and leaned back on her elbows, spreading her legs. Her hairless cunt and inner thighs were already slick with juice, proof of her excitement and arousal.

Wordlessly, Dawn brought one head of that 20 inch long double dildo to her pink pussy lips, rubbing it up and down, spreading herself open for Kennedy to see.

"Ooooh," Dawn whispered, sliding the purple coloured dildo into her pussy. Her pink hole opened up beautifully, fulfilling its intended purpose of being a cocksheath, and swallowing the silicone slab of meat.

The blonde girl pumped that purple cock in and out of her pussy slowly, sliding it in and out of her squelching pussy.

"Kennedy, please, I wanna share a dildo with you!" she begged, spreading her legs wider.

How could Kennedy resist those pleading blue eyes? Of course she couldn't.

And to be frank, she didn't want to resist, her own cunt was starting to gush, pushing out a wave of slick in anticipation of grinding up against Dawn's pornstar cunt. Kennedy wasted no time in crawling over to Dawn and spreading her legs as well. She scooted closer to Dawn, lining up their cunts, then grabbed ahold of the other purple head.

It was thick, a decent size for a good stretch. Kennedy threw back her head and moaned softly as she eased the dildo into her sopping wet pussy. She rocked herself forwards and backwards, her cunt greedily slurping the silicone cock into her body inch by inch.

Dawn was looking down between their bodies, open-mouthed in naked admiration of how Kennedy's bald pussy slid so easily onto the faux dick, and how their pussies got closer, and closer, and closer until -

-their cunts kissed with a loud, wet, smack!

Kennedy reached for Dawn's hips, pulling her forward and mashing their pussy lips together completely around the double dildo buried deep inside both of them.

"Oh gosh," Dawn whispered, eyes fixated on where their bodies were connected by the purple dildo. Every time Kennedy rolled her hips, their cunts would separate for a few seconds, allowing a glimpse of that thick, massive slab of silicone piercing both of their cores at the same time. Then in the next instance, it would disappear, completely tucked away out of sight in each of their front holes.

Dawn caught on quickly, even if she had never scissored before, she was a natural at fucking and this was no different. She swayed her hips side to side, moving one leg over Kennedy's so that they could get even closer together. She rocked forwards roughly, driving the dildo deep into their cunts at the same time, and moaned loudly. Kennedy's cunt was slick with their shared juices and her clit slid against Dawn's own, stimulating both of them at the same time. Her cunt walls were also stretched out, forced wide apart by the new invader. It was long enough to press up against her cervix, the slight discomfort making Dawn hotter than ever. Dawn moaned again, rolling her hips to grind her slick pussy against Kennedy's slit.

Kennedy couldn't help but grin. She pinched Dawn's nipples and twisted hard, making the younger girl yelp in pain, but Dawn didn't protest or try to get away. She just stared up at Kennedy with wide blue eyes, panting as her pussy was invaded by the purple monster.

"Look at us, our cunts are french kissing," Kennedy purred. She canted her hips at an angle until her pussy lips were pressed down diagonally over Dawn's pussy lips. With each clench of her cunt, her nether lips would twitch, making it seem as if her cunt was really french kissing Dawn's nether lips.

Dawn was completely mesmerized. She clenched her hole as well, and moaned as her pussy walls were rubbed by the dildo in her. But Dawn, teen slut extraordinaire, didn't let that distract her from 'french kissing' back using her pussy lips.

The combined slick from both their cunts made obscene wet slapping sounds as the two girls rolled their hips in unison, intent on chasing their cum peaks.

"C'mon Dawn, let's come together!" Kennedy goaded the younger girl. She leaned over the blonde, their tits mashing up against each other, jiggling and swaying to and fro as they continued to hump onto the dildo between them.

Dawn pushed herself up and kissed Kennedy roughly, twining their tongues together. She pulled back for a breath.

"Let's french kiss on both ends," she said mischievously.

Kennedy laughed and nodded, leaning forward for another kiss.

They kissed with both their mouths, and their pussies, all making the same wet slurping noises. The double dildo in their holes stimulating their inner walls with glorious friction, stretching out their sensitive insides. Their holes were so open, so receptive to cock that every time their hips slapped together, the purple dildo would disappear completely from sight, forming a solid internal bridge from one young cunt to another, linking them from inside to out. Although Kennedy had lots of lesbian experience, she couldn't recall having ever done something quite like this. They were grinding, cunt to cunt, mouth to mouth, tit to tit, skin sliding against each other as they scissored frantically towards their mutual orgasm.

Kennedy was so attuned to the lust of the girl under her, that she knew when Dawn was about to cum. She reached between their bodies and gave Dawn's clit a hard pinch, at the same time hissing 'Cum, you little slut, cum!'

The blonde yelped in pain, her young body tensing up on the double-headed dildo. Whether she knew it or not, Dawn had subconsciously started to associate pain in her love nub with an orgasm. With a few twists and flicks of Kennedy's expert fingers combined with the horny ache in Dawn's cunt, it was easy for her to cum, and cum hard!

"Oh oh oh!" she moaned, grinding her cunt down on the dildo inside her, forcing it deeper.

"That's it, slut, cum for me, cum like the slut you are!" Kennedy kept up a litany of slutty affirmations, assuring Dawn that she was a young, teen, whore who loved getting her pussy and ass fucked, and that she could and would cum on any cock.

Dawn, flustered and aroused at having her true nature repeated over and over again, could only listen and moan, her holes twitching with every affirmation.

"I love cock, I love cock," Dawn panted as she rode out her orgasm on the dildo.

Kennedy started to pump her hips again, slamming their bodies together on the monster inside them.

SLAP! SLAP SLAP! SQUELCH! SLURP SLAP

Their cunts squelched loudly at the rough fucking, each full of arousal and love for getting dicked hard.

"I'm cumming too!" Kennedy gasped, she leaned back and let her pussy squirt its juice all over Dawn's hole and nether region. The younger girl made no protest, only watched wide-eyed as liquid spurted out from Kennedy's pink little pisshole, drenching Dawn in girl juice!

Kennedy moaned loudly and then slammed herself down a few more times until her cunt had stopped throbbing.

Then she slowly eased herself off the purple dildo. Dawn made as if to take it out but Kennedy stopped her. She bent the dildo back on itself, backwards to touch it's cum-slick head to Dawn's asshole.

The younger girl's eyes widened in realization and enlightenment immediately, understanding what Kennedy wanted her to do.

Dawn raised her legs higher, spread them wider, then moaned as Kennedy forced the other tip of the dildo into Dawn's asshole.

"That's it, slut, you can do it, you can take this!" Kennedy praised as Dawn's sphincter opened up. It, like Dawn's pussy, was meant to be a cock sheath, and it took to its job eagerly, slurping up the purple dildo with practiced ease. Dawn moaned as the purple monster was slowly forced into her anus, expanding her sphincter.

Kennedy admired the stretch of the pink rosebud, puffy and red as always with the amount of anal Dawn did each day.

Dawn's rocked back and forth slowly until at long last, the only thing left of the double ended dildo was a bridge connecting her cunt to her ass.

Kennedy couldn't resist pulling out her phone and snapping multiple pictures of her blonde roommate, legs spread and a long silicone cock penetrating both front and rear holes at the same time.

"Fuck me please," Dawn begged. Kennedy obliged, setting her phone down and using her hand to manipulate the dildo in and out of Dawn's young cunt, pulling it halfway out and shoving it back in completely again and again and again.

It didn't take long for Dawn to cum again, her anal desires winning out every time. She went into another orgasm, her large chest heaving as her cunt and asshole squeezed their occupants happily, massaging and milking like the holes of a true slut.

"I hope you enjoyed that, Dawn, because you're not getting any more anal for the next four days." Kennedy remarked with an evil grin.

Dawn, who had been relaxing in her post-orgasmic bliss, was instantly shocked into sitting up straight, the dildo still buried inside her.

"What, why?" Dawn protested, gesturing at all of the toys.

"Well, the twins have been inviting people to their boys party on Friday night. There are going to be about 15 hot men there, and they asked if you could be the star of the night." Kennedy said, getting up in search of a cloth. She came back and shoved Dawn back onto her back, easing the toy from her well-fucked holes and wiping Dawn down with the cloth.

"Star?" Dawn asked, still not quite understanding, what was she starring in?

"Yes, the star of the anal train."

Dawn's mouth dropped open, pink lips parting in surprise.

"15 men?" she squeaked "In my asshole?"

Kennedy shoved three fingers into Dawn's pussy and curled them forwards. Dawn's pussy was starting to juice again.

"You like the idea, don't you? You want a night of anal depravity, a night of non-stop anal drilling by 15 men. Your little shithole will be used for its intended purpose - a cock sheath and a cum dump!"

Kennedy punctuated each word with a wiggle of her fingers. Dawn moaned out loud.

She couldn't deny that the idea of being passed around, cock after cock slamming into her rear hole was incredibly arousing. These men would use her hole relentlessly. She wouldn't be able to stop them if she wanted to! Well, not that she wanted to. If one man could fuck her through three or four mindblowing orgasms, then 15 men could give her 15 times as many!

"What do you say, Dawn?" Kennedy asked.

There was only one answer Dawn could give.

"Hell Yeah!"

--

The four days leading up to Friday were not pleasant for young Dawn Simmons. The 18 year old loved having her shitter filled. After months of frequent anal, it was strange to leave her asshole empty. Like the previous anal ban, Kennedy tried to make up for it by giving Dawn's pussy a lot of attention.

And just like the previous anal ban, it wasn't quite enough. There was still an ache in Dawn's bottom, a yearning to have a thick cock shove its way inside and ream her pert ass out.

When Friday night rolled around, Dawn dressed in her sluttiest outfit - no bra, no panties, her shirt knotted just under her large tits, and a skirt that barely skimmed the bottom of her asscheeks. She headed to the twins' apartment, full of nervous anticipation of getting reamed in the ass by 15 different young men.

Kennedy opened the door for Dawn, pulling her into a filthy kiss to the catcalls of Maxwell and Winston.

The older girl wasted no time in pulling Dawn into the spare bedroom and then yanking Dawn's shirt open to expose her perky tits.

"You look so good like this," Kennedy whispered against Dawn's lips. She slid one hand down and frigged Dawn's pussy hard, making the blonde girl gasp.

"Now, before they start arriving, I think we're going to put these few toys to good use."

Kennedy held up the leather cuffs and the blindfold.

Dawn looked at her doubtfully.

"Are those, really necessary? You know I'm going to be a good little anal slut, right?" she asked, feeling a little insecure.

Kennedy patted her hair and kissed her gently.

"Of course, I do. I just love the idea of you restrained, blindfolded, not knowing the identities of the cocks you're taking up the ass. Wouldn't it be exciting? Walking around campus and not knowing which of the boys had taken your shithole and pumped it full of their sperm? It would be interesting, wouldn't it?"

Dawn couldn't argue with that. How would it feel like to be so helpless at the mercy of so many men? Each of them would know that they fucked her ass, fucked her mouth, came inside her little bottom. But she wouldn't know them, wouldn't recognize their faces.

At any given time, the men she was talking to on campus could have been the one to ram their dicks deep inside her rectal cavity. They would know how her hole felt, clenching on their cocks, know how she looked as she came helplessly from anal sex.