Care to Take a Lady Out on a Date?

by MisterEdd


Family Dinner

You sat next to the bed watching Rarity sleep, the rising and falling of her chest almost hypnotic. You found some stray hair lying over her cheek and, pinching it between your fingers, lightly tucked it back over her ear. This was your marefriend. This was a pony that, just a few hours ago, cut her parents out of her life because they didn't approve of you. She chose you over her own family, a fact that brought you some shred of pride but mostly a metric ton of shame.

When you and Rarity agreed to be exclusive, you never in your wildest dreams expected this to happen. No, it shouldn't have happened. She never should've been placed in that position in the first place and it made you sick to your stomach that she had. Rarity was the Element of Generosity and you? You were a smart-ass drunk that wasn't even supposed to be here. Watching her sleep peacefully made your heart ache and you knew damn well why. You were in love with her.

When you first arrived in this crazy bass-ackwards world, Rarity was a little wary of you but still selflessly made you clothing free of charge just so you weren't stuck in the same outfit. Following the stuck-in-Equestria-forever revelation, you spent the next few weeks in an almost constant state of inebriation, thanks to "compensation" Princess Celestia gave you. She subsequently found out about your drinking problem and now ensures you have a monthly allowance sufficient enough for pay for food and utilities. The rest you earn through various odd jobs, including as an assistant to Mayor Mare. Seriously, did her parents see the future and name her that or was it somehow some gigantic coincidence?

Anyway, one night, Rarity found you drunkenly crying in the rain and not only let you crash on her couch but made you breakfast the next morning. That was when your feelings for her truly blossomed. The fact was, she was always there for you when you needed her but what have you ever done for her? You foalsat her little sister and did some chores. Real boyfriend material here.

Back on Earth, you were a shitty boyfriend and this led to ninety-seven percent of your break ups. Your girlfriends accused you of being lazy, unreliable, and emotionally unavailable, dumping your sorry ass for someone better. The truth was, your relationships consisted of hot sex, fast food and the occasional dinner date. You briefly jettisoned your thoughts when Rarity rolled and mumbled in her sleep, producing a stupid grin from you. Rarity was...special, a rare-cut diamond in the shape of a small talking horse with a heart of gold.

And she loved you.

You weren't stupid. When Rarity's parents interrupted your post-sex talk, your marefriend was nervous about something and sounded like she had a truth bomb to drop on you. You were mostly certain that it was the three magic words and booting her own mother and father out of her life for not accepting you was proof of this theory. Giving Rarity a peck on the check, you witnessed her smile in her sleep before getting your jacket and shoes on and walking out the boutique. Today was a new day, not just in terms of your relationship but your life as well. You were going to be a good boyfriend for a change because the mare sleeping upstairs deserved your full attention.

It was a quiet morning and only a few ponies were out and about, likely due to it being a hour after dawn. You considered going to Sugarcube Corner for a take-out breakfast but quickly decided against it, feeling that it was too damn early for any Pinknanigans. It wasn't that you disliked Pinkie Pie; in fact, she was quick to befriend you, even throwing you a welcoming party just a couple of hours after meeting you. You admired how she made it her life goal to make everypony smile and found her funny at times but you also liked her in small doses. She was loud, random and had difficulties with personal boundaries so you interacted with her at tiny intervals.

Instead, you chose that diner you liked and ordered coffee, four bagels, cream cheese packets and a side of baked potatoes. You paid and stepped out with your bags, excited at the thought of having Rarity wake up to find you'd prepared breakfast in bed. Oh, that dazzling smile and those sapphire eyes. Was there any better kind of payment? Well, aside from gold bars or a blowjob.

Heh, maybe she'd be so touched, she'd be willing to-

No! This was about doing something nice for your marefriend, not sexual rewards for basic kindness!

The whole walk back to the boutique was spent imagining those velvety lips sucking you off. Did you mention that you were kind of a prick?

Rarity was still asleep by the time you sat back down beside her, everything laid out on a wooden serving tray. You leaned forward and kissed the end of her snout, one finger stroking her cheek. She moaned, eyes fluttering open and then squinted up at you. You'd had girlfriends that were smoking hot but woke up looking like trolls, some of whom you didn't even want to look at. Yet in Rarity's case, aside from a frizzy mane, was just as perfect as usual.

Damn, you had it bad.

"Morning beautiful."

Rarity stretched, a sleepy grin forming. "Good morning, Anon." She then sniffed. "What's that smell?"

"Coffee, bagels, baked potatoes. You know, the major food groups," you joked as she sat up.

"You...got me breakfast?"

You moved the tray onto her lap. "Correction: I got you breakfast so you could eat in bed."

Fully waking up, Rarity peered down at the food in front of her. "You didn't have to do this."

"I know. I wanted to."

Rarity smiled, her eyes filling up with moisture. "You are such a sweetheart." Pecking your cheek, she lifted up a bagel with her magic, slathered it with a healthy dose of strawberry jam, and took a dainty bite. You dug into your potatoes only to catch a familiar pair of blue eyes staring at you.

You stopped yourself from speaking with your mouth full, swallowing your food before asking, "What's up?"

Rarity sighed dreamily. "You. You're just...so good to me."

"Well, you're my g-marefriend, right? Besides, I kind of like you."

She rolled her eyes. "Only 'kind of'? Honestly darling, I was expecting a full-like."

"Okay, okay, fine. I one-hundred-percent like you."

"No, no, no, it's too late." Rarity turned her head up in mock-indignation. "You can't just change your answer like that. It goes against proper etiquette. I'm afraid we'll have to go our separate ways."

"Fine. Then I guess I'm not obligated to give you a special surprise."

One ivory ear swiveled around. "'Special surprise'?"

You crossed your arms. "Well, I was planning on giving it to my marefriend, who I am absolutely crazy about but it seems as though she's kicked me to the curb. Oh well..."

Rarity began to panic and you weren't sure how much of it was acting. "No, no, no, no! I was only kidding. It-it was a joke. Heh heh. So, um, what was that about a special surprise?"

You gently poked the tip of her snout, causing Rarity to emit a little squeak. "Well dear, it wouldn't be a surprise if I told you, would it?" Shit, now she was doing the pouty-lip. "Okay, all I can tell you is that I realized that we haven't even been on a first date yet and I wanted to do something to rectify that."

"Oh Darling!" Rarity flung herself at you, peppering your face with kisses. "So thoughtful! Where are we going? What are we doing? No wait, don't tell me! Could you give me a hint? No don't!"

This mare...

"I was thinking that you and..."-You were about to fall back on your terrible grammar when you stopped yourself in the nick of time-"...I could dress up nice and go to Canterlot. What do you think?"

You were suddenly stricken by the most sultry pair of bedroom eyes you'd ever seen.

"I think...I'm hungry for something a bit more...rich in protein."

Boi-oi-oi-oing!

~*~

Stopping by your place, you flipped open your mailbox and collected three pieces of mail, which was two more than you were used to. The first two were a coupon for a free super-deluxe daisy sandwich from Hayburger Princess and a flyer for Bulk Biceps' Fitness Course. As for the third, it was in an envelope that read, "FOR MY SWEET ANON" in green ink and carried with it the scent of mint-tea. There was only one mare who fit both of those. Tearing the envelope open, you unfurled a tri-folded piece of pink paper, which read:

Bipedal Beloved,

Yours are the arms that I want to hold me tight
Those lips, how I wish, would brush against mine
Our passions would last all throughout the night
The love we'd share would be the greatest of all time

My marehood quivers at just the thought of you
Filling me with your love-cream until I burst
My brains would melt from how hard we'd screw
I would even swallow your seed, quenching my thirst

My human, oh my homo sapien amore
I wish that my womb could bear your foals
Make me your little cock-hungry whore
Unlike other mares, I'll even let you put it in my tail-hole

Yours, obedient and ever-horny,
Lyra


To be fair, her skills had improved considerably since the first time she'd sent you a love poem:

Roses are red, Violets are blue, come over to my house so I can fuck you.

After that, her material became more creative, even thoughtful at times. Sure, about ninety-nine percent of it pertained to hot sex between the two of you but at least there was actual effort put into it. Most guys would've found it extremely creepy...and it was, but it was oddly endearing in a way and at the very least she never took it too far. There were times where you were actually afraid that she'd roofie your drink or sneak into your house and tie you up while you were sleeping but she respected your boundaries. Well, almost. There was that one time that you came home to find her sleeping in your bed, a pair of your underwear covered in her love nectar but at least she apologized and promised to never do something like that again.

It probably helped that you let her keep the underwear.

Inspecting the mail, you decided that since you were already in a relationship and you were too lazy for weight-lifting, the coupon was going to be the only thing not going in the trash. Maybe Rainbow Dash would want it? For a mare obsessed with staying fit, she sure enjoyed her fast food. It was just kind of a shame that it did nothing for her hindquarters, which were flatter than day-old soda. Hell, for how petite Fluttershy was, even she had more junk in her yellow trunk than Dashie did.

Speaking of Fluttershy, you saw the pegasus just the other day buying bird seed and had a nice little chat. It felt so much like old times that you'd almost forgotten about the whole possible dating/herd stuff. That is, until it was time to part and she gave you a peck on the cheek. Now, such public displays of affection were common amongst ponykind and normally you wouldn't have a batted an eye. Except this was a prolonged, wet kiss that, coupled with a dainty wave, made it clear that she most certainly retained her feelings for you. She even gave her rear an extra shake as she walked away.

And your eyes followed that ass like sailors follow the North Star.

Now that you thought about it, would it really be so bad to be in a relationship with two mares? Not only was it the norm here but there were a lot of added benefits. Aside from the mating process, herds were also a family and that meant love and support from all participants, from housework to finances, everypony chipped in. You'd have another special pony to turn to in case Rarity was indisposed and, not to sound like a horn dog, an extra vagina to stuff should Rarity be unable to fulfill that oh-so-sweet role. You weren't blind; Fluttershy was quite a lovely young mare and such a sweetheart too.

If it hadn't been for Rarity, you were fairly certain that Fluttershy would've been the one you'd fallen for.

You unlocked the door and immediately got to work preparing dinner. With how often you've spent time at the boutique, you made the offer to invite Rarity over for a home-cooked dinner, a prospect that she was absolutely giddy about. As you chopped up the onions, a warm fuzziness filled your chest at the anticipation of tonight. Rarity would come over, enjoy a nice meal you yourself prepared and flash you one of her signature smiles. You just wanted to show her that being with you was the right call and to ensure that you kept your promise about being a good boyfriend. Plus it was a really awesome blowjob that she gave you and you were honor-bound to repay her.

It was a little after five when the doorbell rang, which was funny since the agreed-upon time was six and Rarity was the type to either arrive on time or be "fashionably late," never early. Setting aside your salad tongs, you answered the door, only to find Sweetie Belle sitting patiently on your welcome mat. Yes, you were happy to see her but thrown off considering what happened between you, her parents and her sister the other day. How was it that she was even here? Considering the conversation with Hondo and Cookie, there was no way they'd allow Sweetie here.

"Hi Anon!"

"Um, hi Sweetie. What are you doing here?"

The filly's grin became cartoonishly wide. "I came here to see you!"

"Okay...do your parents know that you're here?"

Sweetie's smile vanished. "C-could I come inside? Please?"

Nodding, you stepped aside and she sluggishly entered, her bubbly sweetness having vacated the premises. Shutting the door behind you, you watched as Sweetie clambered on top of your couch and took a seat, her tail wrapped around her. Seeing her like this hurt; she may not have been your actual sister but she felt close enough to it and you wanted to do nothing more than cheer her up. You soon joined her on the couch, sitting down slowly so that she didn't go flying. Some awkward silence passed before Sweetie finally spoke, every word drenched in sorrow.

"After Mom and Dad got in yesterday, they were really upset, like really upset. They sat me down and told me about how you and Rarity were a couple-which I already knew-and how that was...wrong. I mean, what's wrong about that? You love Rarity and Rarity loves you, so what's the big deal? Anyway, they said that...that..."

At this point, Sweetie's eyes were watery, her nose sniffling lightly. "I'm not allowed to see you anymore. You or Rarity." She scrunched up her face, tears racing down to her chin.

"Sweetie..."

The dam broke, the filly shoving her face into your chest and sobbing uncontrollably. Gingerly, you brought your arms up and pulled her into your embrace, a gesture that she welcomed without contest. A mix of sadness and anger filled your heart, giving you the urge to storm over to her house and give Hondo Flanks a good punch to the muzzle. As for Cookie Crumbles, you would never hit a mare but drop-kicking her over a fence wouldn't be as egregious. But instead, you shifted so that Sweetie Belle laid on your chest, your hand gently stroking her mane.

Once the filly cried herself silly, Sweetie lifted her head up. "Why would they say that? What's the big deal? They always taught me to be nice to others but then they..." She sniffled and rubbed her face, her eyes bloodshot from all of the weeping. "So what if you're not a pony? It shouldn't matter if you're in love, right?"

You exhaled through your nostrils. "It's...difficult to explain. Your folks think that because I'm not a pony, things will be hard for Rarity. I can't give her foals and not only that, but since not everypony's fine with me, they might not treat Rarity so well if they learned that she was in a relationship with a human."

"That's so stupid! It doesn't make any sense!" She shouted through gritted teeth. Normally, you would've enjoyed how cute she looked while enraged but all you could think about was how much you hated seeing her upset.

"I know, Sweetie. It's complicated. Some ponies think that only ponies can date each other and unfortunately, your parents are those ponies. But I think it's because they love your sister and only want the best for her."

"If they really loved her, then they would stop being so dumb and realize that the best thing for Rarity is you!"

You shrugged. "I can't change your parents' minds. All I can do is, well, do the best that I can with the situation."

Sweetie placed a hoof on your chest. "You're like my brother and I love you."

You smiled. "I love you too, Sweets. If I did have sister, I'd want her to be exactly like you."

A gentle grin spread across her lips, a grin that you were more than happy to mimic. She softly laid her head on your chest and sighed. You rubbed her back, neither one of you saying a word. These past two and a half years had seen you being bombarded by bump after bump on one hell of an emotional roller coaster. You'd been blasted to another world, transformed into a depressed alcoholic, developed feelings for your pony friend, engaged in a night of hot drunken sex with said friend, formed a romantic relationship with her, created a divide between your friends with the news, unintentionally caused your new girlfriend to basically tell her parents to go fuck themselves for disapproving your relationship, and are now having a heart-to-heart with someone you considered family. You weren't an emotional person before coming to Equestria and that wasn't such a bad thing.

"Anon?" You looked down at Sweetie Belle. "Could I stay a little longer? I don't want to go home."

Reluctantly, you nodded and gave her a kiss on the scalp, making the filly giggle. You returned to the kitchen and just put the finishing touches on dinner when the doorbell rang once again. You glanced at the clock, discovering to your surprise that it was six on the dot. Had Sweetie really been here that long? You placed Sweetie back onto the couch and went to answer the door, finding Rarity on the other side, the widest smile on her face.

"Hello Anon," she crooned in a seductive manner, adding in an eye flutter for added flavor.

"Hey Rares." You bent down and kissed her, delighting once more on the feel of her lips against yours. "Come on in. I hope you don't mind buuuut I kind of have a guest over at the moment."

"Oh? Who..." She caught a glimpse of the filly on the couch. "S-sweetie Belle? What are you doing here?"

"Hi Rarity! Anon and me were just hanging out."

"I see." Rarity then turned back to you. "Anon, what happened?"

You leaned down close. "Your parents told her to not see me so she got upset and came here."

Rarity shook her head, muttering something under her breath. "Of all of the...I'm going to give them a serious talking-to tomorrow. This is unacceptable."

"I know. Seriously, I'm two seconds away from kicking your dad's flank."

She placed a hoof on your leg, rubbing it gently. "And that's why you're my boyfriend. But all jokes aside, please don't. It'll just make things worse."

You nodded and showed her to the kitchen, followed closely by Sweetie Belle.

Rarity took an appreciative whiff. "Mmm, what is that delectable smell I'm picking up on?"

"Blue cheese salad with deviled eggs and shredded beets."

"Aw, beets! I hate beets," Sweetie grumbled.

"Now Sweetie Belle," Rarity lightly admonished. "Anon spent all of this time making this and it's only right if you eat it all. Besides, you want to have pudding afterwards, don't you?"

Rarity's parents were too liberal when it came to Sweetie's diet restrictions, letting her stuff her face with cookies and chocolate bars. When in Rarity's care, the fashionista been trying her best to ensure that Sweetie ate healthy, discouraging the consumption of sugary sweets and instead fed her peanut butter crackers and celery sticks. It was only on occasion, such as Nightmare Night or birthdays, that she allowed her little sister to consume candy and ice cream. You had a fondness for pudding and after giving her some during one of your early foalsitting sessions, Rarity took inspiration, buying packs of pudding as a snack for Sweetie. Still, you couldn't let this opportunity pass.

"And how can you get any pudding if you don't eat your beets?"

The reference was, of course, lost on the two but it made you satisfied and that made it worth it.

Sweetie Belle begrudgingly agreed and the three of you sat down to supper. You were surprised at how well the meal turned out, given your own piss-poor culinary skills but then again, how could you possibly fuck up making salad? Despite the presence of beets, Sweetie greedily gobbled down her food, washing it down with grape juice between inflating her little cheeks like a chipmunk. Taking dainty bites, Rarity showed her appreciation with little mmm's, her eyes alight with happiness at the meal. It was halfway through the meal when you took note of the mare and filly sitting across from you and it finally dawned on you why this scene made your heart race.

It was like having dinner with a family of your own.

You smiled, the thought bringing you immense pleasure.