Making Your Problems Clear

“Thanks for all this, guys, I really mean it.” You take another gulp of beer as you sit across from Marcus and Jennifer in their living room, letting the evening wind down together. But you still had a little more work to do.

“No problem, bud.” Marcus said smiling, swigging another draught down as well.

Jennifer just huffed, seemingly in frustration at still being up with you and not alone with her husband. She followed her husband and took a drink as well.

You felt nervous trying this, but you needed to see if you could have her. And you think you figured out a way to do it. “So, um, guys… this is kind of awkward, but I have a favor to ask.”

“What’s up?” Marcus asked, his voice genuine as ever.

“Well, part of what’s getting me down so much is that—especially since losing my job and my apartment—I haven’t been able to get a steady girlfriend since our college days.”

Jennifer reined coughing and looked away from Marcus to hide her chuckle. To her, this probably wouldn’t be seen as surprising. And you were counting on that, to some extent.

“Yeah… That’s rough, buddy. But, uh, what are we supposed to do about that? I mean, maybe Jen could try set you up with one of her friends—”

Jennifer snapped back to glare at Marcus for a moment, which he caught out the corner of his eye and course-corrected by cutting the thought off and chugging down the last of his beer. Of course Jennifer wouldn’t want you to bang one of her friends. Which opened things up for you to make your suggestion.

“Actually, I had a more… approachable idea. I think I’m just really out of practice in the dating scene. I was wondering if maybe Jennifer would help me out as a stand-in on a few ‘practice dates’ to get my feet back in the water.”

Marcus’ eyes narrowed while Jennifer’s exploded open. She spoke first, finally injecting herself into the conversation. “Absolutely not.”

Marcus opened his mouth, but you cut in quickly. “C’mon, guys. You always want to help me when I’m in a difficult situation, no matter what, right?”

Their eyes glazed over again, their minds soaking up your words and rearranging their thoughts. After a few seconds, their eyes went back to normal. Marcus shifted uncomfortably, but spoke up a few moments later. “I don’t know man, it seems kind of weird… but we do want to help you out here.”

You pushed on before Jennifer could speak up too. “C’mon, guys, you want to see me happy, and Jennifer helping me out when I need her makes me very happy. And it makes you happy too, Marcus.”

Their eyes clouded for even longer this time. Just like in the restaurant, Marcus’ cleared first. “Well… ok. If Jen’s up for it, she can help you through a few practice dates, I guess. So long as it helps you out and makes you happy.”

Jennifer’s brow furrowed as she looked at you with disdain. But she turned back to Marcus, then back to you. She sighed with a look of defeat before saying, “Fine. I’ll help you with a couple of practice dates. But no funny business.” The last sentence came out with an edge of hostility, but her assent was what mattered. You’d got her.

You smiled and raised your glass in a mock toast. “Thank you so much, guys! This makes me so, so happy.”

Marcus looked very pleased hearing that, and even Jennifer’s stony expression softened for a moment.

“How about we do a lunch date tomorrow then?” You continued. Marcus would be at work, so it would be the perfect time to lay some more commands out for Jennifer.

Jennifer pursed her pillowy lips as she seemed to consider actually spending more time with you. “Sure. Lunch is fine.”

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“Dustin, you ready?”

The knock at your door pulls you into the waking world with a heavy feeling of sleepiness still bearing down on your head. You turn to look at your phone, and see that it’s 10:13 AM. Marcus will already be at work, so it must be—

“Dustin! Wake up. Don’t be such a slob sleeping all day.”

You swing yourself out of bed and walk to the door. You open it with a yawn, and are greeted by a view of Jennifer wearing a standard sweatpants and hoodie fit. “Morning, Jennifer. Why the rush?”

She scowls at you, apparently hoping you would shrink away and leave her sightline. “Because I want to get these practice dates out of the way as soon as possible. I’m doing this because Marcus loves you like a brother for some reason, but I would still rather not do it. So hurry it up and get dressed.”

God, for such a beautiful girl she really didn’t spare words with you. But that was fine. You’d get her slobbering on your cock soon enough. “Wait, are you going to wear that on our date?”

She let out a short, cold laugh at that. “You’re not my husband, so you’re not getting me into a fancy dress for brunch.”

You’re right, you’ll be lucky if you’re wearing that much, you thought. “Jennifer, you need to dress for the occasion if you want to really make me happy. Otherwise this won’t feel like a date simulation.”

Her eyes glazed over. She huffed in frustration. “Whatever.”

“Go put on something else for me. Something better for a date than this.”

She turned around and walked back to her room, almost slamming the door in your face.

______________________

It was better, you decided, but still not good enough. She’d changed out of her baggy pants into bell-bottom jeans, a decent shirt, and shawl that obscured a bit more of her figure. This was progress. But she would go further.

“Much better! But it’s not typically the kind of outfit a girl I’d date would go for.”

Jennifer just stares daggers back at you and replies with her usual venom when you’re alone, “Excuse me? You’re not exactly overburdened with choice, Dustin.”

You take it this time. Because now you have an edge. “Maybe so, but I normally go for girls with a kind of ‘gym girl’ aesthetic. Go put on some leggings and a matching sports bra. Then we’ll go get something to eat together.”

Her eyes muddied and she shook her head. “Dustin, I’m not going to be your gym bunny. I—”

You pushed on. You weren’t going to lose her now. “Go put it on, Jennifer. Make the date good for me.”

Her eyes practically rolled up in her head for a moment before snapping back to you. She turned to walk away and you knew you still had her. “Fine, you fucking weirdo.”

You watched her walk away with a massive smile on your face.

______________________

“This better?” Jennifer said walking back into the living room.

“Much better.” You replied. And it really was, honestly. Jennifer’s delicious curves were wrapped in the thin synthetic covering of her tight pink leggings and a matching sports bra that showed off more cleavage than you’d ever seen her show before. She was absolutely stunning. Her ass looked incredible, and her massive tits squeezed into her sports bra were worth dying for. But, once again, you wanted more. “There’s just one problem though…”

“WHAT?” She shouted, her cheeks red with anger and discomfort at wearing such a relatively showy outfit. She looked so cute like that.

“Turn around and I’ll tell you.”

She obeyed much more quickly this time, turning to let you gawk at her ass. The app really did build off previous orders, you decided. “Yup, I can see your panty lines. Would def not work for me on a date. Go put on a thong for me.”

She whirled back around, opening and closing her mouth in unspeakable rage as her eyes fogged. As the fog cleared she muttered in frustration and anger while she walked to her room once more. “Fucking pervert.”

You stayed smiling. You might be a pervert, but Jennifer was now just a pervert’s plaything.