The Chubby Bully and her Himbo Ch. 03

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Jessica fucks a bunch of people before Spring Break.
8.1k words
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Part 3 of the 7 part series

Updated 06/12/2023
Created 11/16/2021
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"Miss Hill, did you not hear my question?"

"Huh?" Jessica snapped back to reality. The bald wrinkled dean sitting across the desk was giving her a concerned look. "I'm sorry, could you repeat it please."

"I asked you if you had any passion in your chosen field. You should have graduated two years ago, but here you still are. You've taken some of your classes up to three times."

Jessica nodded and looked down. She didn't really have an answer.

She had dressed up in what looked like the most proper clothes she owned, a blue turtleneck sweater and a loose pair of jeans. She was wearing natural makeup, an unusual look for her who preferred gaudier looks and bright colors.

"I have not asked you here to reprimand you or denigrate you, Miss Hill. As the dean of this establishment, I care deeply about the success of all of my students and that includes you."

The dean grabbed a folder from his desk and placed it between them.

"I have read some of your high school essays. Remarkable. So remarkable that we had them checked for plagiarism, but no results came back. These texts - your texts - are wholly originals. They can rival the prose of even our average English literature graduates. Which is why I am baffled to see you taking a degree in archiving."

"If archiving is so bad, why is your distinguished establishment even wasting time giving degrees for it?"

The dean took off his glasses to rub the bridge of his nose. "There is nothing wrong with archiving, Miss Hill, but you could do so much more. It would be like if you had the capacity to be a doctor but chose instead to become a nurse. Both are necessary and both are distinguished career path, but not everyone can-"

Jessica tuned out the rest of his sentence. It took everything from her not to grab him by the scruff of the neck and shove him out the window. Fucking haughty prick piece of shit. As if a fucking dean is in any position to denigrate other people's professions.

"... you have the capacity to do so much more. And obviously, your passion for archiving must not be infallible, or else you would have graduated already, wouldn't you agree, Miss Hill?"

"I like archiving. My academic missteps are due to circumstances related to my personal life which I do not wish to share with you at the moment."

"Our health center has a therapist, if you wish I could refer you to her. It might help you to meet with her." He produced a card and passed it to her.

"I will consider it." Fuck your therapist.

She barely listened to the rest of what he had to say, agreeing and nodding to make him move along, then she shook his hand while mentally viewing him getting shoved into a garbage container, before taking her leave from his office.

As soon as she was out, she pulled down her nose ring from her nostrils. Her septum was still pretty sore from having been pierced two days ago.

Not five minutes after leaving the Dean's office, she heard her name called.

"Jessica," a calm low voice called.

"Mister Dick," she quipped when she recognized her interlocutor.

Professor Johnson laughed. "What a pleasant surprise to meet you. Oh, I see you have a new piercing."

"Don't you have a class to prepare, mister?"

"I just finished the last correction for my students' midterms, my schedule is wide open." He looked around to make sure no one else was close enough to hear. "At least, for the next hour or so."

Jessica considered his untold proposition. She was feeling pretty shitty at the moment and could use the moral booster.

"I got some edibles in my office."

Am I really this easy?

Jessica knew the answer to that question, of course, and thirty minutes later her jeans were on the floor of the professor's office and she was getting her pussy eaten on his desk, waiting for the buzz to kick in. He hadn't gotten any better at cunilingus in the last year. At least he's handsome. And I do have a bit of a teacher kink.

Once his half-assed pussy-eating was done, he got up and flipped her over on the desk. He was one of those guys that saw cunilingus as nothing but a mean to get the girl wet for sex. Jessica didn't care, even if he didn't make her climax, she had already had her treat. After putting on a condom, he started pounding into her.

"Jessica, oh, Jessica," he kept murmuring in her ears, completely entranced by her cunt. Jessica was enjoying the act, but she felt like somehow it had been more enjoyable last time, when she was still in his reference class. Maybe the idea that he was putting his job on the line by fucking her made it feel better. Not that he wouldn't be in big trouble right now if they got caught, he was still a professor at the university and she, a student. Jessica let out a loud moan.

"Hey, shhhhh! These walls aren't sound-proof!"

"Then... better make surrre I do... not noise too much," she slurred. The edibles were definitely kicking in. She looked back at him with a smirk, waiting for his next move.

She weakly whined in protest when he stuffed her own panties in her mouth like a gag, but then dropped her head back on the desk like a docile pet. Considering her waistline, the gag was quite large.

The panty gag did make it hotter and he continued to fuck her while whispering her name. She wanted him to be rougher, to pull her hair and choke her, but part of her was hesitant to tell her about her darker tendencies. This is good enough, she tried to convince herself. But during the whole act, she could only think of having sex with someone else. She had a specific person in mind for that. Or rather, two specific people.

He came, then put the wrapped-up condom in a tissue and threw it in the trash. She spat out her large pair if underwear.

"Can... get another for th' road?" she pleaded, pointing at the box of edibles.

"Well, you know, they aren't cheap."

Jessica let out the beginning of a lewd moan, which was stopped by the professor's hand suddenly covering her mouth.

"Fuck, Jessica, are you crazy?"

She angled her head forward slightly and raised her eyebrows. Haven't I been a good girl? Don't I deserve another treat? Fuck, I do sound like a dumb little pet... I wonder if Scott is into pet play. Josie definitely is. No, don't think about her.

"Alright, sure, whatever." He gave her another weed gummy before urging her to get dressed and leave his office furtively.

-----

Jessica groaned in her bed. She still felt like shit after her morning meeting with the dean. Fucking her old professor had not raised her mood nearly as much as she had hoped and she had spent most of the day napping, eating and masturbating. Her fluffy black cat sleeping and purring by her side did make her feel a tad less like a bloated trash bag.

She wanted to feel better, so she went to the ol' reliable; scouring her contact list for someone that was available and willing.

Me: Can I come to your place tonight? *peach emoji*

-sent 9h25 P.M.

Scott (Tarzan): i rly gotta study tonite jess, exam tomorow n day after. can see u friday? finish @3

-sent 9h30 P.M.

-----

Me: Wanna Netflix and chill? *peach emoji*

-sent 9h30 P.M.

Big Dick Bill: Raquel and I are back together, I can't see you again.

-received 9h33 P.M.

Me: When she breaks up with you again, you got my number *kiss emoji*

-sent 9h33 P.M.

Big Dick Bill: It's not going to happen, Raquel and I are in love. You mean nothing to me.

-received 9h35 P.M.

Me: Wow, ok, rude. I'm changing your name in my phone.

-sent 9h37 P.M.

Tiny Dick Bill: I don't care.

-received 9h40 P.M.

Me: When you text me in two weeks for a blowjob because she broke your heart for the eleventh time, I'll be expecting an apology for that mean comment.

-sent 9h43 P.M.

-----

Me: Hey, are you doing anything tonight?

-sent 9h35 P.M.

Gym Stud 2 (blond): Yeah, not you.

-received 9h45 P.M.

-----

Me: Hey, are you free tonight? *peach emoji*

-sent 9h40 P.M.

Library Cutie: Please stop texting me, Jess.

-received 9h50 P.M.

-----

Me: Hey, wanna hangout tonight? *peach emoji*

-sent 9h51 P.M.

Pete Davidson Lookalike: I'm not really into fat chicks anymore.

-received 9h56 P.M.

-----

Me: Hey, wanna hangout tonight? *peach emoji*

-sent 9h57 P.M.

Ponytail (girl): I'm sorry Jess, but I can't tonight.

-received 10h17 P.M.

-----

Me: Hey, wanna hangout tonight? *peach emoji*

-sent 10h10 P.M.

Ponytail (guy): Busy tonight, but I wouldn't say no to some good head tomorrow morning.

-received 10h14 P.M.

-----

Me: Hey Al, does any of your guys wanna have a threesome, like, tonight? I could use the company.

-sent 10h20 P.M.

Allison: Jess, I don't think that's a good idea.

-received 10h21 P.M.

Me: Al, you don't have to worry, I'm not going to kiss you or anything, I know you don't want to do any girl-on-girl stuff. We'll just both focus on the guy! It'll be fun.

-sent 10h23 P.M.

Allison: No it's not that. I think I got a flu or something, my head is killing me and I'm going through all my tissue boxes because my nose is all gooey and stuff.

-received 10h25 P.M.

Me: Ewwww TMI stop.

-sent 10h25 P.M.

Allison: But you can come chill in my room and watch Gilmore Girls with me. My dorm-mate is at her boyfriend's place, I'm sure she won't mind if you use her bed, you'll be all comfy and at the other end of the room from me.

-received 10h29 P.M.

Me: I'm good, thanks.

-sent 10h33 P.M.

Jessica looked through her contact list and sighed. There was one number she had promised herself she wouldn't text...

Me: Fuck you.

-sent 10h36 P.M.

Evil Bitch: That's a weird way to formulate a booty call.

-received 10h37 P.M.

Me: You down or not?

-sent 10h37 P.M.

-----

Jessica hesitated in front of Josephine's door for almost a minute, before knocking strongly. She did a double-take when the door opened and it wasn't Josephine, but rather a short, shy-looking redhead. Classical music played softly in the background.

"Are you the pig?" she asked. There was something unhinged in her eyes.

Jessica rolled her eyes, then pushed past her to get into the room. Josephine was sitting at her desk, writing on a notepad. Even in gym shorts and a tank top she managed to look sophisticated. In the dim light of the room, Jessica could see the silhouette of Josephine's head; her hair was much shorter. It looked good on her. Everything looks good on her dammit.

"Mistress!" the small girl squeaked. "The pig is here."

Josephine, without even looking in their direction, dismissed the other girl with a wave. She silently went and sat on a bed, looking in turn at either of the other two women in the room, at Josephine with adoration and at Jessica with disdain. Or jealousy. She's hard to read.

Jessica went up to Josephine and asked in a low whisper, "is that your dorm-mate?"

"Oh, do not feel the need to be coy with my pet," she answered at full volume. "This little kitten is completely devoted to me; you may talk freely in front of her. I like your new nose ring, Jess. It suits you."

"Oh, thanks. I like your hair like that." Jessica looked at the kitten, who glared back at her. "I don't think she likes me very much."

"Of course not, because tonight I'm giving my attention to you rather than her." She dropped her pencil and stood up, attracting the attention of the other two.

She turned her gaze to the pet, who looked back in awe.

"Kitten, in the hierarchy of my bedfellows, Jessica here is above you. You may not call her Pig unless she permits you and you will answer any and all of her orders as if they came from me."

"Oh... Y-yes, mistress. I'm sorry for calling you a pig, Jessica."

"What the fuck," Jessica muttered towards Josephine.

"I know, I am amazing. But not all the glory goes to me. Kitten is a rather natural sub." She walked up to her, grabbed her harshly by the scruff of the neck and pulled her up to make her stand. When she opened her mouth, it was her domme voice. "Undress."

Jessica almost obeyed, even though the order wasn't for her. Josephine's pet took off her pants and undid the buttons on her shirt. Underneath, her body was covered in ropes, digging into her skin in diamond patterns. She had bruises on her thighs and breasts. The only piece of clothing left was a pair of white panties, worn under the ropes.

"Turn around."

Again, Jessica almost followed the order. There was no logical reason for her to turn around, but there was something in that voice that made her want to please. The kitten turned and bent down on the bed, revealing a hole in the back of her panties and showing off the base of a large buttplug.

"She's a virgin," Josephine explained, her voice back to casual. "Her pussy had never been touched by another person before she met me." She grabbed the base of the plug, which made the kitten yelp. "As you can probably guess, her pussy is still untouched."

There was something devious in her eyes as she showed her pet's ass. Jessica had been very neutral about anal before meeting Josephine. Now, it was almost a physical craving.

This is messed up. It's all wrong. This girl is what, nineteen? eighteen? She had her whole life ahead of her and now she's going to be turned into an anal-obsessed fucktoy and she'll end up as a fat pathetic mess... Alright, calm down Jess, you might be projecting a little on that one.

"You're going to ruin her," Jessica uttered. She wanted to be angry about it, but the more she tried to think about the situation, the wetter she got. Just like you ruined me.

She pulled the plug out, making her pet yelp. The plug was a lot longer and bigger than Jessica had expected.

"Holy shit, that's- I didn't think she was up to this size already." Josephine wasn't losing any time training her. She had not been particularly patient with her either, back when they had been together.

"Do you want to wear it?" Josephine extended her arm towards Jessica, holding the thick lubed-up warm plug.

Jessica hesitated. "What about her, your kitten, is she going to... participate tonight?"

"Only if you want. She's quite good at eating ass, I made sure of it."

"Then... Make her push the plug inside me."

-----

Jessica was sprawled over Lucy's bed while her friend was busy setting up their afternoon activity.

"I messed up last night."

"What did you do now?"

She put her hand over her face to hide the shame before uttering, "her."

"You didn't!" Lucy carefully placed her bong back on her computer desk before stomping over to the bed to slap Jessica on the arms. "You big horny dummy, you gotta stop thinking with your vagina!"

"I know, I'm sorry! I just, yesterday was a really shitty day and she was available and next thing I knew I was having sex with her and... and her pet."

"Her pet?"

"Yeah, her dorm-mate is a cute little gay sub. She reminds me of me at her age." Even though I've never been that thin.

"Me at her age, okay you old, wizened crone."

"Well, nine years is still like a third of my life. I was a vastly different person back then." I was probably like a third lighter too.

"She's eighteen? That's messed up. Jess, your ex is a toxic bitch."

"She is."

Lucy punched her on the shoulder. "Then stop having sex with her!"

"I'm sorry!" She rubbed her painful shoulder. "I can't help myself..."

"Yes, you can. Think positive thoughts. Think about Scott, he's kind and handsome and I'm pretty sure he's not mentally wrecking teenagers as we speak."

"Jesus Christ, what's up with you and Scott?"

"What's up is that he's a really sweet guy and you're always happy when you're around him."

"Yeah, when I am around him."

"What does that mean?"

"I mean, the sex is great, sure, but we're not, like, relationship-compatible, you know? He doesn't want to date me and I don't want to date him, that's it and I'm not looking for anything more with him."

"Jess."

"He's a good friend with a good dick, that's it. We're friends that hookup sometimes, it's not like I can rely on him to always be there for me."

"Jess."

"Stop it, okay, you don't know what you're talking about!"

"Jess."

"I don't- he's not-" Jess couldn't finish her sentence. Words struggled to leave her throat.

Lucy climbed onto the bed with her and gave her a hug.

"I know what you're going through, Jess. I had a friend with benefits once. We agreed to not bring any feelings into the friendship, that it would only be physical. But damn it, I fell in love with him. I crushed hard, I thought about him every day and it became harder and harder to hookup, because being so physically close to someone while wishing you could be closer emotionally... it's painful."

"But then you ended up telling him the truth and everything worked out for the best, congratulations, I'm very happy things worked out well for you and Kim," she said sarcastically.

"Actually... he professed his love to me first, but that's not the point. Have you tried telling Scott that you might want more than what you have now?"

"I never said I wanted more..."

"Okay then, you big mule. If, and I say if, you had feelings for Scott, would you try telling him about it?"

"Hypothetically, I probably wouldn't want to tell him because I would be scared to lose what we already have."

"Huh-uh. Hypothetically, I could task Kim with asking Scott in a subtle way what he thinks of you."

"That hypothetical would only work if they knew each other."

"Well, they are gym buddies."

"Since when!?"

"Since a month ago? You invited Scott to our five years anniversary party."

"And they met there?"

"They talked for like an hour about those stupid Marvel movies. But, inviting him was actually a good move on your part because Kim wanted to try going to the gym, but he didn't want to go alone, so I thought Scott would be great as a gym partner for him. You know, since your fuck-buddy's abs have their own abs, I assumed he was knowledgeable about gym stuff."

"... I don't remember them meeting." Although, I was stoned for most of that night.

"Yeah, you keep bringing Scott to our events, he's kinda our friend too now, it makes sense that he would meet Kim."

"I don't keep bringing him..."

"Allison's Fall Semester's Send Off."

"That was an open party organized by her Sorority, not by her. Plus, he had already received an invitation before I told him to come."

"The Winter Picknick."

"That's a university event, it doesn't count."

"The Back to the Future Marathon."

"Kayla invited like seven people! I'm allowed to invite one!"

"And the one person you invited was Scott."

"I- Yeah, I guess I see it."

"Kayla's Saint-Patrick's Party."

"I already agreed with you! Stop listing, jeez! Plus, he didn't even come to that party, he claimed he had to study or something."