Desperate Times Ch. 03

Story Info
Rebecca get her first TP, and loses her anal cherry.
5k words
4.49
36.6k
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Part 3 of the 6 part series

Updated 06/10/2023
Created 02/13/2021
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After being royally fucked by all six men in the beginning hours of tonight's 5 hour gang bang, Rebecca lay sweaty and limp in a huge wet spot in the bed, made up of hers and 6 other men's bodily fluids, and tried to un-jumble her thoughts. She had just enjoyed the best sex of her life, and had 7 or more orgasms to prove it to herself, and everyone else.

But she also felt horribly used. She knew they didn't care about her, really, they were just taking advantage of her desperate financial situation to get their rocks off.

But. she also caught herself rubbing her clit while she was thinking these confused thoughts. God, WAS she turning into a whore, a slut, a skank? Being about half drunk, with a hormone besotted mind, she decided to put off making that decision until some later point in time, and rolled off the bed onto her very unsteady legs, and began to make her way carefully downstairs....

As she appeared at the top of the stairs, Carl saw her and started clapping. Everyone else joined in the applause, and they started chanting, "The slut is back, the slut is back, through the door, through the door, she's wanting more, she's wanting more!"

Rebecca wobbled unsteadily over to where she had last left her Amaretto Sour, picked it up, and went to the bar for some fresh ice, blushing to her toes as they slapped her on the butt, tweaked her tits, and kept asking her how her "new broken in" pussy felt? She glanced at the clock over the bar, and was surprised to see that it was only 10:00.

Unbelievably, everything that had just happened to her had only taken a couple of hours! 6 dicks, 7+ orgasms, a tit whipping, 6 loads of cum, and a serious cunt stretching fuck from a monster dick, and she had still 3 more hours to go yet tonight! Knowing it was too late to stop now, she put on her game face, looked at Whimper and said, "What's next, boys?"

Whimper said to her and the guys, "Girly (why did he keep calling her that?) our next order of business is to relieve you of your anal virginity. There are six of us here now, and more will be here tomorrow, and we will need all the holes you got to keep us occupied."

"We have discussed how we are going to do this, and since we have never had a anal virgin before, we decided that we would teach you to really like anal before we show you that it is always possible to get too much of a good thing." He smiled wickedly and winked at her as he finished this little speech.

Carl jumped in and said, "We are going to start you out with some small butt plugs, and then since Ballless is the smallest dick here, he will get the honor of taking your ass cherry. You will work your way up to the "big boys', all the while pleasuring as many of us as you can with your other, uh, assets. In other words, mommy slut, we are about to fill all your holes with cock and cum."

Without being told to, Rebecca downs the last of her sour quickly, and goes to the center of the room, bends over and places her hands on the coffee table, and waggles her big ass at the men, saying, "I'm ready." As she looks back over her shoulder at them, she can't help but notice the line of one-eyed willies pointing right at her ass, and she feels a moment of panic.

But as soon as Carl inserts a lubed-up finger into her bum, and starts wiggling it around, then in and out, in and out, her panic is soon replaced by a bit of pleasure. He inserts a second lubed finger, and then a third, and once again her ass is getting a finger fucking. Somebody comments that if Carl keeps that up, that pussy is liable to start running a river again.

Carl says, "well, we better put a plug in it then." He removes his fingers, and slides a medium sized butt plug into her ass, and then tells Leaky to go lay down on the couch, and instructs Rebecca to ride his cock like a cowboy.

As soon as she straddled him and gets Leaky's cock in her wet pussy, Force is right there standing next to the couch, and grabbing her chin, turns her head towards his dick which he forces past her lips down into her throat as far as he can push it as she gags.

Leakey complains that her pussy ain't near as tight as it was a while ago, and they all have a laugh at this and say "Thanks a lot Whimper!"

Carl speaks up and says, "I can help with that," and he bends Rebecca down to kiss Leakey, and removes her butt plug and replaces it with one that is considerably larger. Rebecca yelps as he pushes it past her sphincter, but it is soon in and she is back to riding Leaky's rod like a cowgirl. Leaky tells the crowd that this is a big improvement, and to get the next larger thing ready. Carl says the next larger thing is Ballless, and is she ready to have all three holes filled at once like the good little whore she is?

Rebecca couldn't speak since her mouth was full of Force's invading cock, so she nodded as best she could, and Ballless removes her plug with a popping sound, and takes his position behind her on his knees. He lubes up his wanker, top to bottom, and begins pushing gently into her asshole. Leaky says he can feel her cunt getting tighter already, and to keep on pushing.

As soon as the head of his dick passes her ring of muscle, he slides all the way in and buries his cock totally in her virgin ass! Rebecca actually squealed like a little girl around Force's cock, as for the first time in her life, she not only had a cock in her ass, but one in her other two holes simultaneously! Ballless then tells her to start fucking Leaky again, and he will just stay put for the moment. She concentrates on moving her body up and down on the cock that is underneath her, feeling her ass filled with another throbbing penis, and tries to keep Force from choking her to death.

As she fully realizes she has all her holes filled with rock hard cock, the whore/slut dialog begins all over again in her mind. The dialog doesn't last long though, because Ballless starts moving his cock into and out of her ass in time with her thrusts on Leakey's cock, and this produces a whole new version of pleasure coming from the nerve endings in her ass.

As she shamelessly revels in these new feelings, she feels yet another orgasm building inside of her, but where it's coming from this time, she can't be sure. (When ALL your holes are full of cock, she thought to herself how the hell are you supposed to know what is producing the orgasm?) All she knew is that it felt REALLY good, and that she WAS going to cum, and cum VERY hard if she knew her own body like she was just beginning to. She pushes Force out of her mouth long enough to say, "Don't anybody stop, I'm gonna cum again!" (#8)

She picked up the speed of her cock riding, and Force and Ballless matched her more frenzied tempo. When she reviewed the video days later, the only description she could come up with that did this scene justice was "Frenzied Fucking!" Ballless began slapping her ass with his hands and yelling, "cum bitch, cum slut, cum whore." He kept bragging to her how she was about to get her first load of man cum in her ass, and that she was going to have his ass baby, etc. etc....

As soon as he shot his load into her virgin ass, Rebecca exploded into her own orgasm, but never stopped fucking the three dicks inside of her. She could only moan around the edges of the cock in her mouth, and was surprised to realize that her own right hand was yanking at her clit prior to and after her orgasm.... Ballless backed up and pulled out of her ass, and spread her ass cheeks so that all could see her newly christened asshole gaping wide open. Carl took the opportunity to pour in a bunch of lube into her gaped open hole to mix with Ballless's cum...

Whimper uses a Sharpie this time to write on the small of her back with an arrow pointing to her asshole: "Virgin no more, this hole now officially "opened for business."

Ballless pushes Force out of the way, and presents his softening cock to Rebecca's lips. She looks up at him with wide and questioning eyes. (Surely, he doesn't think...? That thing just came out of my ass!) He said to her, "clean me up slut, it's the least you can do to thank me for popping your ass cherry."

Reluctantly, she opens her mouth, and he slides his nasty cock over her tongue until it is all in her mouth. It's not as repugnant a taste as she thought it would be, but it isn't exactly a peppermint lollipop either, and, he smells like shit. She sighs silently to herself, and sucks him clean all the same, knowing for certain that his wouldn't be the last ass to mouth cock she cleaned up this weekend.

Small price to pay for the pleasure received, she idly wondered? As she was in the middle of this wool gathering, she felt another cock forcefully rammed balls deep into her ass again! She knew without looking that solely by the violent insertion that it had to be Force who was now in her non-virgin asshole.

Force was being anything but gentle with her asshole, and it was all she could do to stay on top of Leaky's cock and not get pushed off the couch. It was a good thing there was plenty of lube and cum in her ass, because Force wasn't about to slow down his tempo for anything. He too delighted in slapping her ass, and calling her names, except he hit her a lot of harder than Ballless, and her ass was soon hurting, burning, stinging, and red with his hand-prints. The more she jumped and yelped when he hit her, the faster his thrusts became, and the harder his dick got. (Funny how she could tell that from her asshole) She knew now without a doubt that Force had a mean streak in him, and began dreading her 12-hour time slot with him.

He called out: "Somebody stick a dick in this loud bitch's mouth, I'm tired of hearing her yell." Next thing she knew, Stubby's enormous cock had spread her jaws and lips wide open again. She liked this dick, even if it was so huge and stretched out her jaw. She could get his entire short member in his mouth, and enjoyed the feel of her nose and lips in his pubic hair. He smelled good, too, unlike the ass to mouth cock she had just smelled.

She didn't have to move to suck on him, Force's ramming of her ass provided all the back and forth motion she could use, in fact, she had to grab Stubby's butt cheeks to keep her balance while her ass was being fucked so violently. Stubby leaned forward and told her to stick her finger in his ass, that it would feel good to him. (Really? That felt good to guys too? She was learning a lot this evening!) When she did this, she could feel the cock in her mouth twitch and stiffen, so she had to assume he did indeed like it.

Force slapped her ass twice more, much harder than ever before, and then shot his load deep inside her ass. He couldn't wait to pull out, and pushing Stubby aside, grinned wickedly as he presented his dirty dick to Rebecca, and said: "you know what to do Whore, clean it up!!" After she licked him clean and swallowed all the mess, Leaky pushed her off of him, and announced that it was his turn and that he was about ready to cum anyway, and that she probably needed him to wash out her asshole with his fire hose of cum.

Stubby took his place on the couch, and Rebecca grinned as she straddled her favorite cock, and worked diligently to get that fat cock entirely in her pussy once more. It wouldn't go in, so she spit on it a few times and tried again, meeting with success this time. She sighed a small sigh of pleasure as she enjoyed the way his beer can stretched out her lips and made her feel even fuller than Big Daddy, or Whimper. (Yep, this cock was her favorite, she decided. But then again, it hadn't been in her asshole yet...)

With her cunt stretched as wide as it would go by Stubby, Rebecca leaned over and presented her recently twice fucked asshole to Leaky. He slid easily into that assailed back door, and began slow, methodical thrusts. All the way in, all the way out. This was different from the previous two fucks, as Leaky was forcing her sphincter open and closed with each penetration. At first it was uncomfortable, but it soon became pleasurable, and she began grinding her hips down onto Stubby's rod and let Leakey fuck her ass. She felt very full, very sexy, and very happy at this particular moment. She leaned down and locked lips with Stubby, and stopped her movement and just enjoyed the feelings generated by Leaky's gentle ass fucking.

She felt another orgasm building, and whispered to Stubby that she was going to cum. In a voice loud enough for everyone to hear, he said, "Let me feel you cum on my cock. Make love to me baby!" This unexpected tenderness from him sent her over the edge, and she tried to watch his eyes as her pussy convulsed and contracted on his member. Leaky never stopped his anal administrations while she was cumming, and this particular orgasm seemed to last a very long time to her. When she came back from her out of body experience (#9) , Stubby was grinning widely, and she could feel Leaky's voluminous jism running out of her ass and down her left leg. Leaky crawled off the couch and went to clean off his own dick, telling Big Daddy it must be his turn. It was pretty obvious that Stubby was happy right where he was....

Rebecca's arm muscles were trembling by this time from supporting herself during the last three ass fucks, so she asked if they could change up the positions somehow. Big Daddy told her to get off of Stubby and that he would take his place on the bottom. He had her lube up his big tool with some Astroglide, and then told her to straddle him, with her back to his face. He guided the tip of his big pecker to her gaping asshole, and told her to sit on it.

She tried to comply, and quickly discovered how much bigger his cock was than the last three that had just used her shit hole. It hurt like hell as she tried to take him in! She knew enough by now to go slowly, so she asked if she could bend over the couch like before, at least until he got inside of her, and then they could resume the current position. (She didn't have enough strength in her legs to support her above his long rod while she tried to get it in.)

This plan was put into place, and after several "Ow's, and Oh Shit's," Big Daddy got at least the head of his cock past her ring. They both waddled backward to the couch, and Rebecca slowly let herself slide down about halfway onto his long prick before she had to just hold that position for a minute and let her asshole and insides adjust to this new bigger invasion. She cracked everyone up when she said, "OK, I could really use a drink right about now!" Stubby fixed her one and held it up to her lips, while she supported her whole body weight with her hands on Carl's thighs.

Big Daddy told her to "quit screwing around and take that cock up your whore's ass," and reaching up to her waist, he began pulling her down onto his long and thick member. Rebecca was breathless and shaky by the time she was fully sitting on Carl's lap, and he had his tool now completely buried in her ass.

"Oh my God," she said, "Somebody fill my pussy to take my mind off of this, please!" Stubby was only too happy to oblige her, and hopped up on the couch between Carl's legs, and grabbing hold of her calves, he began to push his bigness into her slick cunt. With her ass being stretched by Big Daddy, there wasn't much room left in her pussy, and Stubby had to push like hell to get his fat dick inside of her.

Almost as soon as he got it in though, they all could see Rebecca tremble and shake through yet another small orgasm, which was #10 if everyone was counting correctly. As soon as Stubby was totally inside her opening, he began fucking it, while Carl did the best he could to fuck her ass from down below.

Truly double stuffed now, Rebecca's eyes were tightly closed, and she had her fingers dug into Carl's thighs. Her mouth was slightly open, and they could all hear her breathing beginning to get faster and heavier as she was subjected to this double penetration by two really big dicks. They all agreed that she apparently liked this gig pretty well. Force, of course, said that all she needed now was a cock in her mouth, and it would be a picture-perfect moment. Whimper agreed and told them to get the cameras out, and he walked over and stood by the couch and turned Rebecca's head to the side, saying, "I've got something for you girly!"

She opened her mouth as wide as she could, taking him in her mouth, and he told her that this was her first triple penetration, but that it certainly wasn't going to be the last, and how did she like it? Well, it's hard to answer a question with a mouth full of the biggest cock in the room, so she just leaned backwards down onto Carl's chest, and motioned with her hands in the universal signal of "come here." Whimper had to get down on his knees by the couch to fuck her face now, and Stubby was giving her pussy all that he had to give.

It was fast, furious and sweaty for a moment, until Carl announced he was gonna fill up her ass, and the other two men stopped to watch her reaction as Carl spewed his spunk very deep into her asshole. He bucked and thrashed underneath her, groaning with the power of his orgasm, and she egged him on, telling him to "give it to, give it to me, fill my virgin ass up!"

When he had finished, he told her to get off of him, and turn around and clean him up with her tongue. Stubby backed out of her pussy, and as Rebecca turned around and bent at the waist to comply with this direction, Stubby told her it was his turn, and he began the job of getting his wide cock past her abused and gaping sphincter.

He first poured more lube into her opened asshole, telling everyone he could see Carl's cum way down inside of there, and of course they had to have a picture or two of her red, gaping bum hole. He wiped some more lube onto his own cock, and told Rebecca to keep working on Carl's flaccid penis, and that he would try to be gentle, but she was taking all of him if it ripped her apart.

He also told her that he had never ass fucked anyone, that he was simply too big for anyone to handle, but he thought that she was just enough woman to be the first. "You mean just enough slutty whore, don't you?" was her response. Everyone agreed that was more precise terminology....

It took a whole 15 minutes, and a lot of crying out in pain from Rebecca, but neither of them gave up, and finally Stubby's super fat cock slid all the way into Rebecca's ass! She literally stopped breathing when he slid past her ring, and they wondered for a minute if she had passed out.

Their question was soon answered when she began her OMG, OMG, OMG routine, and thrust herself back into Stubby, asking non-verbally to be fucked. She sounded like she had just run a marathon, she was breathing so heavily. Stubby fucked that ass good for 3 or 4 minutes, and when he could tell she was working up to an orgasm again, he suddenly stopped.

She whimpered, "Don't stop, please, Stubby?" He backed them both around together, sat on the couch, and told her that she could have some more just as soon as Whimper got his tool in her pussy! "OMG, Hell no, I can't take that too!" she said.

"We think you can, girly, and you will, won't you?" said Whimper. She wearily nodded yes, and he crawled up between their legs, and with a total lack of gentleness, forced his huge one-eyed willie between the swollen red lips of her fucked out cunt. From her reaction, you'd have thought they had shot her son; the wail that came from her throat was unearthly! She stopped breathing again, and Whimper just waited out the moment.

Once she opened her eyes again, and started breathing again, he wasted no time starting his thrusting. It was still amazing for all the bystanders to see those 11 inches disappear totally into her tiny pussy, especially knowing how tight it had to be with Stubby's beer can up inside her ass! The cries coming from Rebecca were both painful to hear, and thrilling at the same time. All wondered if she was being hurt, but they all also suspected that this little slut was going to eventually like it.

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