The Double Date: Part 1 (Patreon)

Author's Note:  So this is the first part of a multi-part short story (less than 10 parts).  It's a format I've used before, but not much recently.  I've wanted to write a WG story with this premise for years.  Kinda flips the script on typical WG stories, and I really want to explore that.  This will kind of fill the one-off story slot this month, although I might or might not be able to finish it before the end of the month.  This first part is about 2,300 words so I'll be posting something else tonight to hit that 4,000 word weekly goal.

Enjoy!  Feedback as always is appreciated.  Thanks for all the support!  Have a great night!

-Polaris

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The Double Date

By Polarisdreamer

Part 1

After our double date with Joe and Caleb, two cute brothers we knew and liked from working at the hospital, Grace, my older sister, took it upon herself to acquire some additional information about them. While we were sitting in the back seat of Joe’s car, as they were driving us home from our flirty night of bowling, beer, and buffalo wings, she muted her phone, asked for mine, muted mine, and then used my phone to call her phone.

I wanted to ask what she was doing, but she just shushed me, and sneakily stashed her phone in the gap between the front passenger seat and the center console of Joe’s car, right between Joe and Caleb. Then, once they dropped us off, and left, she informed me of her intention for us to listen in on the guy’s conversation with each other while they drove home.

“This feels wrong.” I couldn’t help admitting, as Grace checked to make sure the receiver was muted, so the two handsome men couldn’t hear us eavesdropping, and then put it on speaker so we could hear them perfectly.

“You said you wanted my help getting Caleb to like you. This is what it looks like. If you’re not okay with that, you can walk right now before we listen to this.” Grace snapped back without a hint of remorse, “Otherwise, just shut up and listen. We can’t read their minds; this is the next best thing.”

I felt dirty. It was immoral listening to whatever Joe and Caleb talked about while they didn’t know we could hear them, but then again, I’d been crushing on Caleb for the last sixth months and was desperate to hear his impression of me after our first date, “How are you going to get your phone back?”

“Once we’re done, you’re going to call Caleb and tell him that silly old me forgot my phone in their car. They’ll drive back and return it to me or give it back to me at work tomorrow without being none the wiser.” Grace explained without sounding worried.

“You’ve done this before, haven’t you? Is this why you were pushing for a double date?” I muttered looking at my older sister with new eyes. Grace had always been a little nosey, but now she looked more to me like an evil genius.

“Yes, and yes. I learned this trick in college ten years ago. It helped me avoid some serious red flags. Now shut up and listen.” Grace barked, finally fed up with my resistance.

I was going to say something to my older and clearly wiser sister, but the air vanished from my windpipe the second I heard Joe’s voice casually echoing out of my phone…

“You know that they found a ship over in the Middle-East that supposedly has the same dimensions as Noah's ark? It's further evidence of the Biblical flood.” Joe’s voice was gruff sounding but earnest. He was two years older than Grace and had only recently quit smoking.

"I don't understand how the flood could work at all.  Like, how did all the fish survive?" Caleb responded. At 27 years old, Caleb was five years younger than his brother, but sounded far more mature.

"Huh? Fish can swim dude.  A flood isn’t exactly a problem for stuff that can breathe underwater. You sound high.” Joe chuckled to himself clearly amused with Caleb’s statement.

Defending himself, Caleb continued, "Wouldn't the changes in pressure and salinity disrupt if not destroy massive swaths of sea life?  And wouldn't a flood like that leave all bodies of water with similar enough compositions, which is very different from what we see now? Also, why aren't there deep-sea fish fossils on the top of mountains? The flood story really doesn't make any sense to me as an actual event."

A moment of silence followed after Caleb’s little rant. Before Joe sighed and huffed, "Well, I guess it's all in what you believe."

“This is what guy’s talk about after a double date?” I muttered to Grace, as she shrugged her shoulders.

Then without speaking in reply, she tilted her head and motioned for me to follow her into our apartment complex. While Caleb and Joe continued talking about nothing particularly important to us, Grace welcomed me into the apartment we shared and motioned for me to take a seat on her couch, before she proceeded to open up a bottle of wine for us to share while we continued eavesdropping.

After a few sips of wine, the moment we were waiting for finally arrived…

“So, what did you think of Anna?” Joe wondered. He’d clearly been beating around the bush until now.

“She’s great at bowling.” Caleb replied without sparing a second to think about it.

I couldn’t help but smile in response to Caleb’s praise. My family had routinely gone out bowling weekend after weekend growing up. I’d hated it back then, but I did appreciate the skill now that Caleb was admiring me for.

“I mean how do you like her? She seems really into you.” Joe elaborated, as my trim stomach started swirling with nerves. I looked to Grace for help, and she just motioned for me to drink more wine, so that’s exactly what I did.

“I like her a lot. She’s really cool. You know I’ve always wanted to date a Brunette.” Caleb admitted sounding cheery, much to my delight.

“You gonna take her out again?” Joe wanted to know, as I internally praised his line of questioning right now.

“I… I don’t know.” Caleb admitted, as I nearly coughed up wine. My face started burning with embarrassment and fear.

‘We had so much fun though! What went wrong??’ I worriedly thought to myself, as I tilted my head closer to the phone.

“Well you better know! I’m planning on taking Grace out again, and I bet she’ll be none too pleased if you break her little sister’s heart. What’s the problem? She’s not your type, huh?” Joe teased, “Give her time, she could be one day.”

‘What does he mean by that??’ My thoughts continued racing.

“I think she’s attractive. As is.” Caleb argued, keeping the dwindling ember of hope alive within me, “She’s got a great ass.”

“Yeah, but I bet the problem is… you prefer Grace. Don’t you? She’s a lot thicker.” Joe continued teasing.

‘Oh no… Is Caleb a chubby-chaser or something?” I worried since at 5’5 and 120lbs, I was pretty skinny, aside from my fuller butt cheeks. Thanks mom.

I looked to see how Grace was handling these revelations. She was four inches taller than me, but at about 220lbs, she also had to weigh at least 90 or 100 pounds more than I did. After making eye contact with me, she just raised her eyebrows and took a sip of wine, appearing unphased.

“No, I prefer Anna. Definitely. Anna’s a little shy, but she’s really kind, and that laugh is super cute. Grace is nice, but she’s a little too loud and extraverted for my tastes.” Caleb explained.

“Well good. I wasn’t offering to trade. I’m not a chubby chaser, but Grace is just plain hot. Did you check out her tits?” Joe replied, “Anna’s got nothing on them.”

‘Grace’s tits are only bigger than mine because she’s way fat!’ I couldn’t help, but instinctively think feeling a little boob envy toward my bustier sister.

“No. I only have eyes for Anna.” Caleb replied, much to my relief.

“So, if you like her so much, what’s your hang up with her?” Joe questioned.

I was all ears.

“It’s not Anna, it’s just… when I told my ex about my weird preference, she freaked out… And you know how things devolved from there.”

‘Weird preference?’ I couldn’t help but wonder as I noticed Grace was reaching over to refill my glass of wine. I’d already drank the whole thing. I hadn’t even realized!

“Liking bigger girls isn’t weird dude. I like Grace. She’s a bigger girl. I’m not weird for liking her. You’re not weird because you exclusively like bigger girls. Everybody’s got their preferences. No shame in that.” The big brother replied sounding like he was trying to console Caleb.

“My preference isn’t for bigger girls, it’s not that simple, I get turned on by the idea of someone like Anna, a thin girl, gaining weight and getting chubby or even… pretty fat. Imagining her clothes getting tighter, thinking of her overindulging in public… Society forces women to accept the idea that they are supposed to be skinny. The idea of a conventionally attractive girl giving in to her cravings, letting go, and letting their body grow into the opposite of what society says is ideal is just so sexy to me.”

I couldn’t even breathe. All my body could do was continue listening in the purest of fascinations while Caleb continued spilling his feelings out to his brother…

“So, I’m not like in love with overweight people, for whatever reason I’m drawn to someone in the process of going from a socially acceptable weight to a socially unacceptable weight. That transitionary phase is what gets me off. I’m addicted to it. To see Anna’s body go from tight and fit, to round and smooth, to soft and squishy, would be a dream come true. To see her cravings for food, and enjoyment of eating escalate with every pound, would be a dream come true. I think about this stuff constantly. Every time I’ve ever had sex. But I know my fantasy is unrealistic. I’m not sure I’d ever want to encourage someone to actually even do that for me, even if they consented to it, because it just feels… I don’t know, shameful?”

“So, this isn’t about Anna. You sound pretty mixed-up dude. Maybe consider seeing a therapist. I don’t think I’m qualified to help you with a moral f*cking quandary like that. With my sh*t, I can ask a girl if I can tie her up, and if she says yes, then boom, fantasy fulfilled, I can go back to focusing on my day job and sh*t, but yeah with you, I can see how that might drive you crazy. If someone gets fat to please you, there are consequences. It’s like a scratch you can’t itch, isn’t it?”

“You mean an itch I can’t scratch. Yeah. You said it. I’m just realizing, I’m probably going to have to settle for less than what I truly want. And I don’t know if I’m ready to give up hope just yet. I’m attracted to Anna the way she is now, her gaining weight would turn me on to no end, but I’d feel so guilt starting a relationship with someone, knowing deep down, I’d want them to change just for my sexual satisfaction.”

“You sound like you need a beer. Wanna come back to my place? Keep talking it out?” Joe replied, still trying to consol his dejected sounding brother.

“I’d like that.” Caleb responded, as I couldn’t stand listening any longer.

I quickly reached out and ended the phone call.

“Hey what the f*ck Anna! It was really getting good!” My big sister blurted out.

“We shouldn’t have listened to that. It was wrong.” I snapped back, shaking my head, “I feel dirty!”

“Wrong or right doesn’t matter. What matters is we learned some very important sh*t about these cute brothers. Joe’s into me, he’s into bondage, and he’s even into me even though I’ve got a weight problem. That’s three green flags if I’ve ever seen them. Caleb, on the other hand, red flags.” Grace insisted on blurting out her opinion.

“I wouldn’t say that. It’s not his fault if he’s got a weird sexual fetish. People don’t choose those. He seems really guilty about it.” I countered.

“Sounds like he doesn’t want to date you unless you put on weight.” Grace replied doubtfully with a slap to her own thick belly.

“Then maybe I’ll put on some weight. It’s not a big deal.” I snapped, not really even realizing what I was saying.

“You wouldn’t.” Grace giggled. Being fit and thin was something I prided myself on as a college athlete, but since graduation two years ago, the only reason I was really motivated to stay in shape was because I wanted to attract someone I liked into a serious relationship. Was it really so weird to do the opposite to attract someone if you knew they liked it?

“I… I might…” I stumbled thinking about it some more, “I… I will.”

“Wow, this I gotta see. Miss health-nut never-missed-a-spin-class-in-her-life is going to purposefully gain weight?? For some guy you’ve been on one date with!” Grace doubted.

“It was a great date. There were sparks! You were there! You know!” I argued.

“Ha! No way! I call bullsh*t.” Grace laughed, leaning back onto her sofa and finishing off her glass of wine.

“I’ll prove it to you. I’ll have a slice of cake. Right now.” I proclaimed, as I quickly arose from the couch and hurried over to the fridge.

“That’s my cake!” Grace complained to me, too lazy to heave her fat backside off the couch to follow me.

“You can afford to let me have one piece.” I shot back, opening the fridge and pulling out Grace’s chocolate cake that she’d purchased for no particular reason other than the fact she couldn’t resist.

“One piece isn’t gonna help you gain weight. You better eat a lot more than that, every day, if you want Caleb to notice!” Grace bellowed clearly, trying to dissuade me.

“Then that’s what I’m going to do, starting from this moment on.” I vowed, as I pulled out a fork, stuck it into the cake and thrust it into my mouth. I didn’t often partake in sweets like my sister did, but even I had to admit. It tasted pretty d*mn good…