Kelly Asks Shaun Out (Week 3)

As Monday rolled in, Kelly’s heart was all flutters. As she made her way into the community college in one of her newly bought jeans and a yellow t-shirt, her new girl gang waved at her excitedly. She was wearing the heels from previous week. She still carried the scarf, but instead of its ‘modest’ purpose from last week, she tied it to her handbag. Her boobs and ass were bouncing with every step even with the restrictive, old granny underwear inside.

As she sat on her desk in the back, the girls surrounded her. All three had the same question – what did she decide? Kelly took a deep breath, and said, “Ok, I’ve made up my mind. I don’t want to be bullied like Amanda. I’ll get a boyfriend. I’ll take Shaun as my boyfriend”.

The girls shrieked in excitement, exchanged lewd glances among them. Sharon, ever the sadist, was the first to respond. “But have you asked Shaun about it?”

“Wh… What do you mean? Didn’t you say Shaun was single and available?”

“Yes, but I never said Shaun was interested in you or asked about you. Who’s to say he doesn’t like some other girl already?”, smirked Sharon. Bullying this naïve housewife was starting to become the highlight of her day, and she was going to milk every drop out of it.

Kelly’s heart sank. The only reason she even agreed to this was because she found Shaun to be really thoughtful and considerate, not to mention mind-numbingly attractive. She hadn’t even considered the possibility that he might be interested in some other girl. Other than Shaun, being the girlfriend to a random weirdo was a repulsive thought to her at that point.

“I… I don’t know, Sharon. I… I didn’t even think about it”, came the stammered reply.

“That’s because you’re a stupid slut, babe”, said Sharon with a mischievous smile. The two other girls seemed to nod in agreement.

“What should I do now, Sharon? I don’t even know any other guys!” Kelly was panicking at this point.

“I might have an idea. But first, you’d have to get bullied to earn that”, replied the sadistic blonde.

... ... ...

Kelly had protested the bullying, but when the girls pointed out that she was still single, she had to give up.

Sharon was acting as the ringmaster now, while Olivia and Carol went to work on Kelly’s body. The housewife was thinking it would be something horrifying like they did to Amanda, but she was surprised to hear Sharon call for sharpies. “How bad could it be?” she thought to herself.

She got her answer soon enough. The girls had folded her t-shirt up to her midriff, exposing her milky while tummy, and tied a knot on the side so it would stay that way. Kelly squirmed at being exposed liked that. This was the first time she showed off her midriff in public, willingly or not.

Kelly felt the dull sensation of the sharpies writing on her bare skin – on her tummy, arms, and back. When Olivia and Carol were done, they took a step back and admired their handywork. Sharon opened the front camera on her phone and handed it to Kelly so she could get a good look at the writings.

When Kelly saw the words, she almost fainted. On her tummy, it said “Cumdump”. They wrote “whore” on the right arm and “slut” on the left. On her back, which Sharon was kind enough to take a picture of and show to Kelly, was written “$2 BJs”.

Kelly was appalled. She looked at the girls with pleading eyes, “I look horrible!”

“Nonsense! You look fucking sexy. We might have to get you some actual tattoos soon”, winked Olivia.

“You guys think I look… Sexy?” asked Kelly, looking plenty surprised at this turn of events.

“Of course. Why do you think we wrote those? So that you’d look better for Shaun, you silly slut”. Sharon’s manipulative mind was working in full gear again.

“Oh… Do you think he’d approve of these?” asked a sheepish Kelly.

“I fucking KNOW it bitch. Now go and ask him. Remember, if you don’t get a boyfriend by today, we’d have more bullying in store for you”, Sharon winked at the naïve woman.

And with a slap on Kelly’s ass, she sent her over to Shaun’s desk.

... ... ...

Seeing Kelly stand near his desk, Shaun looked up from his phone. He had been getting regular updates from Sharon including pictures, but seeing Kelly in person, he could not but laugh.

The formerly modest girl was showing off her midriff with lewd writings all over her, looking laughably awkward. With a shorter top, her ass was accentuated even more. Shaun had already seen her back from the photo Sharon said, but he decided to have some fun anyway.

“Hey Kelly, the tats look hot! You look gorgeous with those”.

“Aww, you really think so, Shaun?” she was blushing profusely.

“Of course. I love tattoos. I think you should get some permanent ones. They’d really suit you”, Shaun said with as much fake honestly as he could muster, laughing internally. In truth, Kelly looked like a trailer trash whore. First step in the right direction, he chuckled to himself.

“Thank you, Shaun. You’re really sweet”, came Kelly’s genuine reply.

“Did you get one on your back too? Why don’t you let me get a better look at that?” winked the huge black guy.

“Oh, it’s nothing, just…”, Kelly started to protest, but she remembered that she was supposed to ask Shaun the big question, so she thought better not to decline his offer. “OK OK, have a look and tell me what do you think”.

As Kelly turned around, Shaun almost laughed out loud. Here was the modest housewife, showing off her fake tattoo to a guy nearly half her age that said “$2 BJs” on her back while her huge ass jiggled with every movement. She looked awkward and trashy at the same time.

“That tattoo looks even hotter than the ones on the front. Why don’t you bend over and let me take a better look?”

Kelly thought about protesting, but remembering she had to ask Shaun to be her ‘school boyfriend’, she complied, bending over a little that made Shaun’s eyes bulge out.

“God damn, the ass on this bitch is a total moneymaker. Fucking jackpot!”, Shaun thought to himself. Seeing the lewd display from the oblivious housewife, he couldn’t help snap a couple of pictures. “Jerk-off material for later”, he smirked silently.

After Shaun was done ogling the brunette, he told her to turn around.

“So, what was it you wanted to talk to me about, Kelly?”

... ... ...

Kelly swallowed hard, her nerves tingling all over her body. Gathering all her courage, she asked him, “Shaun, I wanted to ask you something really important. Would you… Would you… Would you be my school boyfriend?”

Shaun was laughing inside at her awkward attempts to find the right words. “Damn, this bitch really is fucking gullible”, he thought.

“Your school boyfriend?” came a blank stare from Shaun. “I’m sorry Kelly, I only think of you as a friend”.

Panic consumed Kelly as she tried to process what she just heard. ‘Just a friend?’ Shit. Shit shit shit. She had to make this work, no matter what. Or else her new girlfriends would make her life a living hell.

As Kelly was trying to find the right words for a situation she had never been in her life, her phone pinged. It was a text from Sharon, who, along with the other members of the gang, were enjoying the scene unfolding before their eyes from afar.

“Act ****. Make him interested in you bitch.”

“****?” replied a confused a Kelly.

“Yes, tell him how you look better than other girls he might be interested in. If you blow this, be ready for bullying all week and more, you useless cunt.”

“Something the matter?” asked Shaun, fully knowing what was happening.

“No, it’s just a text…”. The next words coming out of a panicked Kelly’s mouth surprised even herself.

“Come on Shaun, don’t you think I look better than any of your other female friends?” She tried flirting clumsily, swallowing her shame. But Shaun just looked at her, uninterested.

“It’s not that, Kelly. It’s just that… I’m seeing another girl. She’s this real looker, very open-minded. I don’t think you could compare to her” Shaun said matter-of-factly.

This hurt Kelly’s ego more than anything. Was she not good enough? Who was this bitch Shaun was seeing?

“Here, I’ll show you”. Shaun pulled up a random Instagram account he had carefully chosen, letting Kelly have a look.

As she scrolled through the profile, she saw why she stood no chance. The girl was a gorgeous blonde, with a killer body, perfect skin and hair. In most of her pics, she wore bikinis, and the rest were shorts or miniskirts. In reality, Shaun was bamboozling the naïve housewife with the profile of a random Instagram model he didn’t even know.

As Kelly’s eyes darted from picture to picture, she felt her heart sink. There was no way this could work between her and Shaun. Why would he choose her over that skanky blonde? She was almost in tears by that point.

“Gotcha, bitch”, smirked Shaun internally. But he made a show of showing fake sympathy nonetheless. Consoling her by hugging and feeling her sizable boobs on his chest. “Fuck, this bitch is stacked”, he thought to himself.

“Come on, Kelly. Don’t be so hard on yourself. You’re still pretty, but I don’t think you can compete with that girl”, he said nonchalantly to the crying girl.

“However, here’s an idea. How about you give it a try for the next week?”

“Give it a try?” Kelly looked at Shaun through her tear-soaked doe-eyes.

“Yes. take a look at what she wears. Maybe not the bikinis, because I don’t think that would be appropriate for the classroom. But how about the miniskirts and the shorts? Maybe the cute, sexy tops too. And I’ll decide if you look better than her. What do you say?”

It was as if Kelly was drowning and someone offered her a lifeboat. “You’d do that for me, Shaun? Really? Thank you, thank you so much”, came her reply. She was genuinely grateful to him. As her spirits were lifting, she realized she was in an embrace with another guy who wasn’t her husband. She quickly moved away, trying to regain whatever modesty and dignity she had left. At least she still had a chance.

She thanked Shaun again and went back to the girls, still showing off her lewd writings and sexy midriff.