Simpin’ Aint Easy Pt. 01 – Embracing a Forbidden Fetish

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This was originally written in response to a prompt on Reddit.

Your HS crush has just messaged you, congratulating you for getting your degree in engineering and asks for a favor. She wants you create her fuck machine for her Only Fans.

Transferring it here in hopes of making it a full series. Enjoy

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It didn’t look like a den of depravity. He’d looked over her account countless times since he’d gotten the message. “Celeste’s Den of Depravity” she described her account, her brand. He knew her as Jennifer Waters, Softball player and surprisingly famous with most of their graduating class. He’d first met her in his physics class. She struggled, he excelled. So, when she caught him staring one afternoon, it was easy enough for Jen to ask him to help tutor her. What ended up was lots of late night chats and Rob doing most the homework for her. He Aced the class, she passed with a C.

*At least my grade matches my bra size.* she said with a sigh and a hint of laughter. Rob had wondered about that opinion for years. At the time, he wasn’t sure if she was flirting with him or not. To this day, he still wasn’t.

The two quickly fell out after that, drifted aside as people do after highschool isn’t the driving force to put them together. Until today, where she arrived at the home of Celeste. The home looked like he was told the American dream would look like. Green lawn, back yard, smack in the middle of the most boring stretch of suburbia. Where people become boring and raise children.

This is where the den of depravity was hidden.

A familiar face answered the door with a smile. She was glad he could make it. If she were asked, she wasn’t sure he would show up. It was an odd request, to be sure. It enough to make anyone in their right mind block her outright.

Rob didn’t, and he had shown up early.

He wore a sweatshirt and jeans, she wore a blue, polka-dotted top with a plunging neckline and a pair of shorts that showed off her thighs. From outside appearances they were just a ordinary suburban couple.

She brought him to the kitchen table where he set down his bag. It was full of contents he brought for demos, the contents you’d have a really hard time explaining to a cop if he were pulled over on the way here. Straps, bondage, gags, phallic objects, clamps.

“Can I get you anything to drink?” she cooed as she made her way to the fridge. Despite outside appearances, the house inside was under furnished. She’d recently moved in after her first year on the site. She was able to afford a home, but just barely. The fridge was dented and loud, clearly second hand.

Like a teen buying an oversized bra on sale, she was hoping to grow in to the space. Or, at least, make it look like she had.

This is what brought Rob here today, she explained as she brought him a diet coke, the only thing to drink she had on hand despite her earlier offer. “So, let’s just get this out here. I’m looking for a fuck machine. Something automated to put on a show, and possibly letting fans control portions remotely. I can afford the first part, and if I’m successful, we can get you working on the second part.” She said this all rapidly and sighed. Her company had been easy enough to process mentally when all of the buyers were faceless.

Telling this to a man she used to know in her kitchen was a different atmosphere.

“Well, okay. Jumping right in to it.” Rob said after a pregnant pause. “A fuck machine. Didn’t the football team used to call you that?”

“They wish.” She smiled, welcoming the joke. “I left highschool a virgin.”

Rob hadn’t realized how much he missed that smile. It brought him back to all those times in her room, in his room, talking about acceleration and how it was distinctly different than velocity. Something he never quite managed to convey.

“But yes, a machine to fuck me and make a spectacle of it. For the fans.” she sighed.

“It’s okay, this is something I’ve never done before, as you could imagine”

She let out a playful “Oh really?”

He waved her off. “But I think it’s doable. but there are questions I have. Questions I need to know for your safety. People joke about wanting to be ruined, but this really has the potential to ruin you. Badly. I need you to understand that risk.” Rob was serious, and he needed her to figure out the risks.

“Sure. I understand. If you need me to sign a waiver or something…”

Rob brought out his phone, and indicated that he’d been recording their conversation. “Just say that you understand the risks and you know I’m working in good faith to make this for you.”

“Oh Rob, I usually charge for a recording.” She smiled, but her face turned somber. “Yes, I, Jennifer Leigh Waters, understand the risks and wish to proceed, Robert Matthews.”

“Never knew your middle name was Leigh, huh.” He couldn’t help but make a opinion.

“There’s clearly a lot you never knew about me, Rob.”

He felt his cheeks go red as he broke eye contact. “Ok, lets get to it. Addressing the elephants in the room.”

Rob produced a number of rubber and silicone toys, ranging from 3″ to over a foot long.

“You have some decisions to make. I wont be offended by your choices, but the larger ones take a little more work, and cost, to ensure safety.”

Now it was Jen’s turn to blush. She wasn’t expecting to need to answer what her preferred cock size was, but it’s something now felt she should have prepared for.

“Wow. Just like that, okay. I was sort of hoping to just use my existing guys. some were gifts from donors and they *really* like when I use theirs.”

“I’m sure you take very good care of your toys, and your pussy is at a perfect PH level, but I would insist on new toys for safety.”

“What if I say I accept the risk, would that be okay?”

“Normally, yes, but as someone who I used to consider a friend, I would really advise against it due to the risk.”

His words hit her harder than she expected. used to consider a friend?. Another thing that felt unexpected, but she should have prepared for. Did he need to be so cold, so clinical about all this? Sex is, by definition, warm and messy.

“Okay, fine, Mr. Matthews. Could I take the day to try them? Make sure they vibe with my “PH levels”?”

She picked up the largest toy and let it dangle. Is this the kind of woman he thinks she is now? Or, she smirked, is this him telling me what he’d like to see?

“Yes, that’s fine. It’s not my wheelhouse after all.” As her eyes were glue to the oversized member, his eyes went down her chest. It certainly looked like time had been kind to her figure. He’d seen her in bathing suits a few times back in school, and those images had been burned in to his spank bank. They were practically founding members. This body now was different.

She caught him staring, just like in physics class all those years ago.

“Yes?” She shot across the table.

“How big are they now?” his tone was less clinical, small hints of desperation snuck in to his voice. He shifted in his seat.

“Robert, really?” She answered his question with a question. She was amused and taken back by the audacity.

He cocked his head to the side, not matching her amusement. “For the machine, Jen.” His tone trying to hide the fact that he was undressing her with his eyes moments ago. What it be like to slide his cock between that cleavage, as he imagined on so many lonely nights before.

“Oh, right. I didn’t think you needed that for this. I wondered it was just for the *wheelhouse.*” She made a gesture to her shorts.

“I wondered maybe you’d like some nipple clamps.” He lied. “Or something like a milking machine.”

She sat there, stunned for a moment. This guy had done his homework on the potential of a fuck machine. Or maybe he just had fantasies of his own.

“It is Celeste’s Den of Depravity, after all, and not Jen’s sad handies behind the Walmart.” Rob smirked.

Jen shifted in her seat, leaning forward. “I didn’t think you had it in you Rob. And they’re Double Ds now.”

“Very unlike that physics grade.” he quickly pretended to wright something down, trying to hide the joy and satisfaction on his place. He’d been sitting on that comeback for a long, long time.

That caught her off guard. “My physics grade?”

“You know, you said it matched your bra size.” He offered.

Her eyebrows furrowed, and then raised with a smile. “Oh, I really did say that back then. I’d forgotten how bad I was at flirting back then. Just announcing my bra size, like come on in boys, Jen’s packing some B cups.”

She was testing him. Had he really kept that fact to himself all this time? Something like that comment would fall off most men’s memories. Had he been crushing on her back then? Was he still? Maybe, she thought, maybe she’d be able to get this whole machine for cheap. Hell, she might get it for free if she played her cards right.

“C cups.” He corrected.

Somewhere, a mousetrap snapped.

Celeste smiled back at him. “Tell me about what other ideas you have for me, Rob.”

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