In the Midst of Callousness 8 (NSFW) (Patreon)

In the Midst of Callousness
Chapter 8 (NSFW)

-VB-

She knew that she wasn’t exactly the smartest woman.

If she was, then she wouldn’t have married an asshole and then divorce him later.

It was, however, what exactly happened.

If she was smarter, then she would have gotten more out of the divorce, but she didn’t and only had custody of her toddler daughter. The judge was very understanding of her plight. He understood, perhaps even sympathized, with her situation to the point where he put a restraining order on her ex-husband.

It was also odd.

Shelly’s situation was exactly the opposite of her parent’s situation; her abusive mother got caught using drugs and cheating on dad, and dad filed divorce and got custody of her and her siblings as well as getting a restraining order on her abusive mother.

Just like she did, dad got proposed by her step-mom, and dad complained about how his parents had the exact same situation.

Was it a repeating fate for them?

Maybe that was a good thing then, because Alan was a nice man. She wasn’t sure whether it was alright for her to ask him about his situation - everything from where he lived, where he graduated, what kind of work he did, and what hobbies he had - because this was just their first date!

… But then again, that’s what she thought exactly on her first date with her ex-husband, and look where that got her? At the same time, her ex brought her to Fugly Bob’s while Alan brought her to Jeannettu, a high end restaurant she’s only had glimpses during her commute through downtown.

He’d asked her to wear her best dress, but even her best felt cheap compared to what she was seeing in here.

As far Alan, he looked … dashing.

He stood tall with broad shoulders. His dress pants looked tight but not overly so from how developed his muscles were (everywhere). He had a simple short side and high fade haircut that went well with his strong jaws and high cheek bone.

‘You know, he might be a model,’ Shelly thought to herself as she and he followed the usher to a table. ‘It would explain how good he looks at the very least. Or is it the other way around? “He looks good, so he’s very likely to be a model”?’

He smiled at her. “Ladies first.”

She smiled at him as she sat down and he followed suit across from her.

A waitress came over soon after, and handed them each a menu.

Shelly opened the menu, took one look at the prices, and nearly stood up to run out.

‘One hundred dollars for a drink?!’ she hissed in panic.

The waitress left and Alan gently tapped her hand. She looked up and saw Alan.

“Don’t worry. I’m paying for it.”

She wanted to shriek at him in her current blind panic. ‘It’s not about having you pay for it! It’s about how -!’

---

Shelly stared at the dish in front of her, harissa quinoa with shrimp and chickpeas.

It was one of the cheaper dishes on the menu, though it still cost her- Alan - fifty dollars for this single dish.

At the same time, she couldn’t … deny that the dish deserved to be expensive.

It tasted great and, supposedly, healthy as well.

“To have taste and health. That’s what money is for, huh?” she muttered to herself.

The best she could provide for little Sophy was a mixed salad with chicken. This was so much more than what she could provide.

“It is,” Alan replied to what she thought she’d mumbled under her breath.

She blushed. “Well, what do you do anyway? I’ve seen you a lot, but, you know.”

He grinned smugly. “Oh, curious about your boyfriend’s job now, eh? I mean, that’s nature,” he chortled. “What if I told you that I worked in cape investment management?”

“Investment… management?” It sounded like something rich people would be involved in.

“Yes. There are many heroes and villains who are rich, especially those among the likes of the Elite.”

She nodded cautiously.

“However, money doesn’t do much when it’s sitting in a vault somewhere. That’s where I come in. It’s my job to turn a consistent profit for the capes who trust their money with me.”

“D-Doesn’t that get dangerous?” she asked him quietly while looking around.

“That’s the thing about my boss,” he hummed. “He’s a cape. A rogue. He also has a lot of … helpers, if you will. No one will mess with us, not when doing so will trigger all other capes and organizations using our services.”

She nodded because it made sense.

“Now, how about you? Last I saw you, you were working in that office.”

She winced.

“Um. Yeah. I kind of left…?”

He blinked.

“What happened?”

“My ex-boss was kind of my ex’s friend.”

Alan grimaced. “I assume he doesn’t give a shit about your side of the story?”

She shook her head.

“... Well, that’s shitty. Want me to go and have a talk with them?”

“No no no! It’s alright,” she giggled. “Besides, I just want to move on.”

He nodded. “Got it. I assume you’re still jogging like you always do?”

“I am! You won’t believe what I saw.”

The conversation and the meal came to an end, and she found herself satisfied with everything. She might have been a little overwhelmed initially by the grandness of the location, but the food was good, the talk was good (and informative), and she … she liked Alan.

Always have, actually, though it certainly started with her liking him as a friend.

Now that he’s shown interest and she saw how … good he looked when he got cleaned up…

“Hey,” Alan called her from where he stood by her side. She looked up and saw him staring down at her. A pleasant shiver ran up and down her spine when she saw his half-lidded suggestive look. “Wanna do it tonight?”

She looked away and almost squirmed in place.

T-This was very different from how it was with her ex.

And despite herself thinking that she shouldn’t be agreeing to sex on the first date, she found herself nodding briefly.

-VB-

Shelly gulped as she slowly pulled down on the straps of her one-piece dark blue dress.

Behind her, she could hear Alan unbuttoning and shrugging off his suit.

When she heard him stop, she turned around, her arms around her breasts and a hand covering herself below.

He, on the other hand, was perfectly fine with showing him.

She saw, momentarily, and gulped as a blush creeped up her neck and burned her ears.

H-He was big.

And thick.

Alan walked up to her and tilted her chin up, and then leaned down for a kiss.

She closed her eyes, expecting him to be rough with her.

But he wasn’t.

His tongue gently probed for an invitation, and she let him in.

He didn’t try to dominate her in her own mouth, and instead coaxed her out.

The kiss ended far quicker than she wanted it to end, and she found herself letting her lips part from him while open and realized that she must have looked like a total slut with her tongue out and a spit bridge forming between the two of them.

Then he scooped her up!

She squeaked in surprise before he set her down on her side on her bed and -.

He sat down on his side behind her.

His hand came up behind her and grabbed a handful of her breast while another went down and start rubbing her.

She bit her lips and moaned as he hastened his fingers. She felt a climax coming and couldn’t stop herself.

She came to his fingers and laid there in embarrassment.

“Can I?” he asked her as he pulled her left leg up.

Half-dazed, she responded with a “yes.”

She felt his thick member brushing under her and along her thighs before he pushed into her and -.

She moaned.

Oh God, I’m a fucking slut.

He started pumping her slolwly, and she grabbed his arms and wrapped her leg around as best as she could.

She felt his dick throb in her, and her own climax started climbing again.

“W-Wait, I’m not s-sure if t-t-today’s a safe d-day-!” she whimpered as he picked up pace and said nothing to her besides his own deep grunting. “A-Alan-!”

She squeezed her eyes close as tears gathered and fell.

She came to his dick on her first date and moaned like a slut when she felt him cum inside of her and fill her up.

Oh no. oh no no no …!

“A-Alan, wait-!”

She felt him move and make face down with how he turned her.

And started pummeling into her.

She mewled as he spread her legs and drive her sensitive vagina inside with the twists and turns while one of his hand not holding her waist vibrated like a drill on her clit.

Her eyes rolled over into her head as she came, her vision whiting out during her hypersensitive orgasm.

When she came to, she found herself still getting railed from above.

Then he pulled her up a little and slammed into her.

Shelly laid there, trembling, as Alan’s dick throbbed and spurted cum in her from above.

She was too weak to ask him to stop when he turned her flat on her back and started fucking her. No, instead, she let herself fall deeper into the drowning euphoria.

-VB-

“Oh no…!” she moaned as she woke up the next morning and found herself in bed with Alan.

Alan smirked at her.

With a blush, she let her hands down from her face and glared at him.

“What if I get pregnant!” she shrieked with few tears in her eyes.

“Then I’ll take responsibility,” he replied casually as he brought her back down flat onto her back and started-.

“Eek!” she yelped when his finger started pumping her. “W-Wait, it’s morning, I gott-!”

He didn’t let her talk. Just kissed her.

And fucked her.

And called her boss and told her she couldn’t work today.

Then fucked her again.

S-She was in over her head with Alan.