Jessica, Anal Bitch Ch. 03

Jessica slept in her own bed that night. It had been a mind-blowing weekend, started off with getting fucked by a guy who could have doubled as her father—a beer-gutted guy in his 50s with graying hair and a penchant for anal and bondage. Then, he'd invited over a crew of nerds and church-goers to tag-team her in a 5-on-1 gangbang with Jessica at the center of attention. The sum of the two experiences had been incredible for Jessica who had experienced more orgasms in less than 24 hours than she'd had in the last year (at least those induced by another man).

She would take a few days to recover being stretched beyond her previous limits, both vaginally and anally. Despite being exhausted from biting off more than she could chew previously, she looked back on the experience in her mind reverently. "Jesus, that was incredible," she thought out loud. "I wonder if Tom would have me back or if he goes through girls like me on a weekly basis..." She resolved that as soon as her body had 75% recovered, she would explore getting invited back for another session.

She hated to admit to herself that perhaps she really was a sub slut like Tom had suggested in the first place...that she might truly be happiest pleasing men's cocks, being lusted after by all kinds of men, the more at one time the better, and that one cock might never truly be enough for her again. It began to make her doubt what love truly is, or why you might need love after you've realized that you can no longer limit yourself to one man...or at least one penis.

She decided to text Tom to thank her for the good time:

"Tom, thanks for today, and last night"

Tom replied back before too long:

"I told you you're a sub slut cock pleaser"

Tom then sent her a series of pictures and short video clips of Jessica surrounded by cock and getting fucked good. At least one of the videos exhibited Jessica clearly shouting, "Fuck my ass!" really loudly. All were quite graphic, and she couldn't help but be impressed by how hot the scenarios came off. If it had been any other woman, she'd have thought it was incredible; however, since it was herself, she still had that sinking feeling that she had crossed a bridge of no return, pics and footage of her now "out there," irretrievable, much like her sexuality, never to be the same, boring, one-man woman that she used to be.

Her hand reached down to the spot between her legs that had gotten rubbed raw earlier, and unsurprisingly it was already wet again thanks to the visuals provided by her new dom. "What am I gonna do?" she wondered, half worried. She was too quickly becoming a one-track minded party bitch with a new love for getting anally thrashed that she wasn't sure where this lifestyle would lead. She just knew she was eager to get back in the saddle for more, and that to wait until the next weekend might not be soon enough to satisfy her urges. "I'm so fucked," she muttered to herself.

...

Wednesday that week while working from home, Jessica's mother called. Her mother lived upstate about four hours away, so their main method of communication was over the phone. Jessica had been dwelling on her predicament, being turned out and yearning for cock for what seemed like all of her waking hours, and decided to ask her mom related questions while they were chatting:

"Mom?"

"Yes, Jessie?" her mother replied.

"Was Daddy your first, or did you date around before you met him?" Jessica asked.

"You know your father and I met in college. We've been together ever since," her mother replied.

"So there was no one else? You never, you know, fooled around in high school or in college before you met Daddy?" she persisted.

"Why do you ask, Baby?" her mother asked, unsure where this was coming from.

"Well," Jessica replied, "I've just been going through some stuff lately, with my recent break up, and wondering in general what it's all about. I guess I've kind of lost faith in love a little, and I wonder if I even see myself ever truly falling in love with anyone. On the other hand, I still desire sex... just not with attachments, at least I think. I don't know. I'm really confused."

"I see," her mother replied. "Don't be too worried about that. Love has its ups and downs in a person's life. To be sure, your father and I have had ours. Still, we love each other very much, and it's natural to go through such cycles... Getting back to your question, however, in fact I did date around both in high school and college. You know I was a cheerleader, but what I never told you, as it would have been inappropriate had I told you at a younger age, was that I experimented quite a bit in high school, less so in college."

"Oh my gosh! Really?" Jessica asked, surprised. "Like what?"

"Well, again, as a cheerleader, my friends and I were always getting hit on by ALL of the guys...the athletes were the most forward, and we were the center of attention at all the big parties and events. It seems I must have dated several of the varsity guys at various points throughout high school," her mother mused.

"Oh shit!" Jessica blurted out. "Sorry, I mean, I had no idea. I should have figured this out knowing you were a cheerleader. I guess I've always known you as my father's wife, as my mother, and it never once occurred to me."

"That's true. I am your mother, and I'm your father's wife. Still, to be quite honest, and I've never told your father this, but I have dated more boys than I'd care to admit," her mother offered.

"Really? Like how many?" Jessica asked in disbelief.

"I don't think I could put a real number on it, but it's probably somewhere in the twenties," she replied.

"Twenty boyfriends?!?" Jessica asked.

"At least, Honey," Jessica's mother replied. "Not to shock you, but since you're old enough, you might as well hear about it... I'm sure I dated at least 20 boys, and slept with almost double that amount. (Of course, i was already 18 by the time I'd started having sex.)"

"WHAT?!?!" Jessica asked. "Are you serious?!"

"I know it sounds like a lot. But it was a different time then, and again, this was the way it was with the cheerleader crowd," she replied. "When i was 18 during my senior year, It felt like every weekend I'd be at a big party with the girls and I'd end up sleeping with my boyfriend or some random jock, partly because we were all doing it, and partly because of all the beer that was expected to be drank at the parties."

"You screwed random guys?!?!" Jessica asked. She couldn't believe her ears. But it all started to make sense. Her newfound libido and appreciation for cock now had a basis that went beyond herself. Perhaps it was a trait inherited from her mother.

"They weren't totally random. I knew all of them to some level, well, at least most of them. Again, they were mainly varsity guys. They all had a lot of confidence and didn't take 'no' for an answer. Anyway, once I graduated high school, I mostly left that life behind, sticking to mainly sleeping with men I dated seriously with an occasional one-night stand, and these numbers were all very limited by that point," she said, qualifying her previous statements about promiscuous sex.

"I see," Jessica replied. Thinking to herself, "So I'm not the only slut in the family after all," she told her mother, "I've wondered lately why I have been inclined to just want men for their sex and not so much their heart. I suppose it's a phase..."

"Perhaps," her mother replied. "When I met your father, I knew almost right away that he was the one, that I could see myself living with him for the rest of my life. I anticipate eventually you'll meet Mr. Right, too. Probably not without looking for him though, but who knows?"

"Thanks, Mom," Jessica said. She now had a better idea of what was going on. She didn't get all the answers she needed, but to persist in asking her mom more questions would only raise unwanted questions from her mother. Jessica's mom was a cock whore, just like Jessica was now. No reason to fight it at this point, and hope that when it's time, she'll meet a good guy and mature out of it all.

...

Sure enough, all Jessica could think about the rest of the day was her mom on all fours barking like a dog for varsity cock while blitzed out on cheap beer, being passed around like a party slut. The thought turned her on more than she could bear as her hand was on her twat more often than it wasn't, pushing herself to several orgasms that afternoon and evening. It was in this moment of sexual frustration that she texted Tom:

"When can we get together again?" she texted.

Not long after: "How's tomorrow sound? 12:00 noon?" Tom replied.

"I work from home. I can probably get away with 3:30pm," she replied.

"3:30pm works," he replied.

Jessica's pussy and asshole were still a little sore from Sunday, but at the rate she was going and the urge for more cock she'd been feeling, she would just have to fuck it and take a chance that her body would be ready. She couldn't get cock off her mind, and the thought of cock in her mouth, pussy, and ass, the taste of their semen, the musky smell of their balls and body odor, she needed it now more than ever.

The night would be difficult as Jessica lay awake, images of Sunday as well as that of her mother getting fucked incessantly by a room full of cock with her cheerleader sisters... Did her mother do anal? Had she gotten into any gangbangs? Regardless, this was Jessica's new reality, and she planned on capitalizing on it while the urge still resonated within her.

...

At last, Wenesday afternoon came, and Jessica left her home around 3:05, checking out of work having worked from home during the whole social distancing thing. When she pulled up to Tom's house, she was surprised by the number of vehicles parked outside. Had Tom rallied the guys again? It seemed clear he must have, and by the looks of it, there could be as many as double the number of guys from before. Apparently Jessica had not yet outlasted her usefulness for Tom yet, she mused. She was excited and grateful for what Tom had done, and she wore this excitement on her face as she stepped through the open front door of Tom's country home.

"Hi Guys!" Jessica said as she walked into the living room with what looked like about twelve guys, most of which were standing or leaning on something, most drinking a beer or a bottle of water.

"Jessica!" called Tom, "You made it! Here's a beer!" He handed her an opened beer, and she got busy drinking it. If things played out the way they were supposed to, she wouldn't have much opportunity to keep drinking it.

"Jessica, you remember Mike, Bill, Ron, and Jake, right?" Tom asked Jessica.

"Hey Guys!" Jessica called out, smiling.

"The word got out on what a little cock pleaser you are, so what you see around you is some extra family and trusted friends that were interested in sampling your wares," Tom said. "I figured from your texts that it was on."

"You're such a people pleaser, Tom," Jessica joked. "The more the merrier! That's what I always say!" she returned.

And like that, clothes started popping off as Jessica kneeled in the center of the room, and one cock after another was freed from its pants while Jessica's eyes beamed, glancing happily into the faces of the men that began to surround her. While some of the guys tried to help her off with her shirt, it was slightly challenging at first because her mouth and hands were really busy getting the crowd going with her cock-pleasing skills. But within a minute her shirt and bra were off, and she was able to get back to her mission of feasting on cock.

Like an octopus bartending in a boner bar, she went to work, stroking cocks, sucking from cock to cock, and before you knew it the better part of what was at least 12 cocks were all standing at attention, waiting for their turn to get off.

Jessica had mostly come prepared. She had applied garish make-up to give off the look for a common Times Square whore. Her clothing was all pretty loose to facilitate easy removal. And her hair had been put in a pony tail to keep the hair out of her mouth and enable some easy hair pulling for the guys. It need hardly be said she did her best to clean herself, both all over her body, but also the inside. After all, nobody likes shit-dick, especially when it involves ass-to-mouth action.

The sight was something to behold for any newby to the gangbang experience. Here was this southern blonde eagerly sucking and jerking off all these guys as if she was in her happy place. She truly wanted it, and it was happening.

What happened next was unexpected... Tom gave a signal and without notice, the men, as if previously assigned, proceeded to give Jessica an oral experience unlike any she'd had before. The men all grab a part of her body and began to tongue the shit out of it. Naturally, one guy was on her twat, another on her asshole, tonguing away just like she deserved, returning the pleasure she'd been so generous to provide moments before. One guy per breast. Men sucked her toes, others her fingers. All these sensitive spots were getting licked and sucked, sending her senses into overdrive. To be sure, she got to feast on a cock while all this went down...after all, that's really what she came for.

Jessica didn't last very long. It must have been seven minutes when she climaxed from all the oral attention she received. Much as she hoped, this was only the beginning of what would be non-stop cock. Tom announced some ground rules before the guys started dicking her up:

"All right Boys, here's the deal," Tom started. "I've invited all of you here to fuck my bitch Jessica good. But don't forget your gangbang etiquette. If you can't blow your load inside of about seven minutes, you need to pull out and let someone else in. Pretty much everybody here is expected home for dinner, and Jessica will get really worn out for those of you holding your load forever. Everybody tracking?"

Without any further ado, Tom beckoned to Jessica to straddle him on the large ottoman that he had in front of the couch. As much as he liked to fuck ass, he wanted first dibs on her pussy. Without hesitation, she climbed up on her love connection and slipped his cock easily into her pussy. She'd been waiting too long for the sensation of cock inside of her, so she was happy to oblige. She started riding his cock nice and steady, her slender and fit figure a sight for sore eyes. All the men in the room had a hand on their cock as they watched Tom get reacquainted with his willing slut.

"What are you guys waiting for?" Tom asked. "She's got at least two other holes here. Help yourselves!"

Bill was always down to fuck a tight ass. He was prepared with lube and stepped up to insert his cock inside Jessica's newly broken in hole.

Again, the pause while Tom and Jessica let Bill stretch her asshole with his cock as he inched it past her anal sphincter. Jessica's head went backward as she experienced that electric thrill that only anal veterans know, a slick, warm, firm cock filling her rectum, resting for a moment as Bill's cock continued to fill with blood, and then slowly rocking back and forth.

Jessica was catapulted back to Heaven as these two men rode her like the fuck meat she now identified as. "Yes, fuck me, Boys! Fuck me like that!" she exclaimed.

Jake, the big guy from Sunday, got in front of Jessica's face and offered his big tool once more. Jessica couldn't speak for the satisfaction of Tom and Bill going to town on her two holes, but she had no trouble opening her mouth to accommodate her friend's manhood.

And there she was again, being used like a true attention-loving party slut. Jessica's eyes closed as she went to her happy place, her sexual wonderland where her senses were stimulated, but her brain was on overdrive, reeling in ecstasy as she harnessed the attention of all these sex-starved men with their hard cocks all waiting their turn for a poke.

Bill was the first to drop a load, right in Jessica's ass. "Agh!" he shouted as he went balls deep one last time, trying to leave every drop in her anal cavity. After he pulled out, Jessica's asshole was left agape as all the men stared at Jessica's ass in all its glory. Ron took the initiative, pulled his cock out of Jessica's mouth, walked around the ottoman and put it in her ass for the second time in a week.

Jessica's head went back again as she was filled to the brim with cock. "Oooohh!" she moaned as the two men stretched her to her limit, pushing as deep as they could, eliciting mutual pleasure among the threesome.

One of the new guys came up and offered his rock hard erection to Jessica's free mouth, which she gladly accepted...she didn't like to be left without something to suck on. She busily went to work on getting this stranger off, fucking his cock with her mouth fast and wet while her two lovers continued to penetrate her with abandon.

It didn't take two minutes for the guy in her mouth to erupt, sending ropes of jizz into Jessica's waiting mouth. She had grown to enjoy the taste of cum, and she was pleasantly surprised by the freshness of this young man's hot load on her tongue and in her throat. "Mmmm, yummy!" she let out, stroking his ego and encouraging any other would-be volunteers for getting sucked.

Tom got close, beginning his final approach on climax. He started banging his hips up and down like a jack hammer into Jessica's twat, BAM BAM BAM BAM BAM!! The thrill of getting fucked hard put Jessica over the edge, causing her to emit her pussy juice from her cunt as it dripped out all splashy getting her pussy and asshole that much more wet and easy to ram while Tom and suddenly Jake both committed to cumming inside of her. She held firm with her hands planted on the ottoman just north of Tom's shoulders as they bucked their hips fast and furious into her jutted ass until they both erupted their semen deeply inside her pussy and rectum.

Jessica's face was a combination of pain, pleasure, and finally relief during this onslaught of passion. She was covered in sweat from the rough fucking and the warm Wednesday afternoon. She took a much needed break sandwiched between these two hung men, reveling in the contact and attention she recently discovered she so needed.

After a few moments, Tom and Jake detached from Jessica. She moved onto her back on the ottoman while Mike proceeded to mount her missionary style. He fucked her solo for a good two minutes, and heeding Tom's ground rules, eventually stood up while holding onto Jessica, offering up a man to take her ass while he fucked her pussy standing. Another newby stepped up and pointed his penis at her asshole. It was already ready to receive after the fucking she'd gotten from Jake. The two men before long started fucking Jessica standing, her body sandwiched between them, her arms around Mike's neck, the new guy gently biting her trapezius muscles while he buried his cock in and out, in and out of her loose hole. If it wasn't for his inexperience, he would have had a tough time reaching climax, her ass was so loose. Sure enough, the new guy was spent inside of five minutes, finishing with his jaw firmly locked onto Jessica's shoulder, leaving a steady stream of cum pouring out of her ass when he finally removed his asspipe.

Getting tired, Mike went ahead and laid down on the ottoman with Jessica on top. He continued to fuck into her cunt until the situation demanded a change. Ron stepped up to fuck Jessica's ass. He was able to stand on top of the ottoman while he rammed his cock in and out of her ass. Jessica was able to position her ass just right for maximum friction enjoyment as the three got into a steady fuck rhythm.

Jessica yelled out, "Fuck my ass, Ron, fuck me!" Ron couldn't believe it. He was trying to bang her good, but it seemed his cock couldn't quite fill her well after Jake's large cock. Tom gave one of the other guys a gentle shove to go and join in. Not sure what to do, he simply got behind Ron who was already fucking Jessica's ass, and he pointed his dick in the general area between Ron and Mike's cocks.