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"Yes, Madam Rarity."
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>You sip the irish coffee slowly, letting the warmth seep through you
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>"Do make sure not to take off your underwear for this one - she's a newcomer, and we want her to come back for more."
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"Does that include my undershirt?
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>"What is it today?"
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"Tuesday - so a neckless."
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>Neckless. Rarity found that term more tasteful than 'wifebeater'. Of course, she thought the concept of a wife-beater was hilarious - who ever heard of a husband beating his wife?
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>"I think not, dear. It's not even fluffed yet shows your collarbone, so..."
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>She trails off, looking out the window
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>You follow her gaze; the lit streets of Canterlot shine below your madame's apartment
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>Rain beats softly against the glass, providing a gentle backdrop to your conversation
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>You detect a sniffle
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"Madam? Madam Rar-"
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>"Rarity. Please, Anon... just Rarity. I'm....so sorry that I asked you to do this..."
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>She turns to look at you, her face calm, but her eyes a maelstrom of emotions
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"Rarara, it's -"
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>"I don't deserve that pet name, and I don't deserve your friendship! If I was better at business, then I could've kept the boutique afloat withou-"
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"Rarity."
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>She stops her self-pity and looks at you again, swallowing hard
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"It's alright. I-I don't mind. This isn't the worst thing that could happen to me, ok? And it's only temporary, right?"
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>She nods, her lower lip quivering - fighting the urge to sob, trying to stay composed for you
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>These pones never could hide their emotions well
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"Rara-"
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>"Don't."
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>You smile and reach forward, petting her head gently
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"Rara. My cli- our client will be here soon. Please make sure you're ready."
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>Rarity nods wordlessly and hops out of the chair, making her way out of the suite
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>This... seems to be getting harder for her
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>You are Anon
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>And for the past 6 months, under the management of your Madam
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>you were the highest-paid, most desirable hooker in Canterlot
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>You thumb through your Jane's file
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>Rarity may have second thoughts about being a Madam, but damn it if she wasn't good at it
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>Let's see
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>Once again, a typical newcomer
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>Is it a bad thing that you're starting to be a little jaded?
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>Good family, 'proper' breeding, used a fake name but didn't cover her cutiemark for the screening photo
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>Hm. No kinks listed, nothing on file...
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>Marked wanting a "romantic" encounter - that's typical as well. Don't want to show your true colors and be branded a weirdo...
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>Probably a mare that wants to 'just try it out'
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>They never showed up just once, though. 
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>A light chime snaps you out of your thoughts, and you slide the file into your messenger bag
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>Or as they call it, a coltpurse
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>Ugh. Sex innuendos and horse puns everywhere
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>Standing up, you make sure your hair is mussed up "properly", your shirt unbuttoned down to your mid-chest, and your demeanor relaxed
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>You clear the table of your coffee, replacing it with a bottle of red and two glasses
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>You sit down, facing the door, and wait
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>That was the 5-minute notice, so at any time you sh-
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>*knockknock*
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"Come in~"
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>You use your deepest, huskiest voice
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>You cross your legs and lean back into the chair, smiling warmly
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>After all, first impressions are important
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>The door handle is wrapped in Rarity's magic, and opens
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>Your Jane stands in the doorway, eyes wide
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>Yes, little girl. You did just pay a few thousand bits for this.
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>She swallows hard, her polished hoof stepping timidly into your parlor
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>You smile and open your arms slightly
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"Love, do come in out of the rain~"
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>No, little girl. You can't leave now.
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>She keeps her eyes locked onto your frame, drinking in your form in all the ways her father told her not to
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>As soon as her tail clears the threshold, the door silently closes on her, an all-but-inaudible click signalling her time has begun
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>She keeps walking towards you - slowly at first, but soon she adopts a more natural gait
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>"U-uhm... G-good evening, sir."
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>Proper breeding still coming out
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>Cute
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"Good evening, M'lady. Please, sit - I promise I won't bite."
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>You smile, making sure not to show any teeth
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>She nods and does so - and you lean forward, pouring her a glass of red
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"It's a horrid night out tonight. Did you have a good trip over?"
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>"Mmhmm...."
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>She stares at the drink you poured - or is it your hands? - and you chuckle
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"It's just a normal, red wine. Or would you prefer a port...?"
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>"Oh! Ah-n-no, this is fine. I just..."
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>You don't fill the silence
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>"...I-I don't typically do this kind of stuff, you know? I'm just, just try-"
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"Love."
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>She quiets up so fast you're sure you hear her teeth clack together
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>You won't get a tip if she stays this stressed out
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"No one knows your name, no one knows you're here. You're trying something exotic in a safe place with no judgement from anyone, so..."
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>As you speak, you see her visibly relax
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"Don't judge yourself."
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>She takes the glass in her magic and sips it, a soft smile playing on her lips
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>"So... so how do we do this, Anon?"
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>Your lip twitches
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"It's bad form to use real names..."
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>"O-oh! S-sorry"
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>You hold up your hand
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"First time, so it's alright. And, this all depends on if you want me to lead, or if you want to."
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>Considering it's her first time, traditional stereotypes will come out so she'll-
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>"I'd like to lead, if that's ok?"
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>You nod and stand up slowly
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>Her ears flat as she realizes just how /tall/ you are
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>You bow slightly
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"So, what would M'lady want to do with me? Or... is the better question..."
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>You drop your voice again
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"What would she like to do to me~"
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>Your jane blushes hard, putting the glass down on the table with a forceful *tok*
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>"Let's...the bed?"
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>She gives you another order-question
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>Less and less you're sure she's ever been with anyone before...
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>You'll bring that up on her next visit. Or the one after that
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>She wraps your hand in her magic, and it fizzles out
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>"O-oh! I uh-"
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>You recover for her, placing your hand on her withers
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>She clears her throat and 'leads' you to the bed
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>Looking up at you, you nod softly and turn around, sitting on the bed
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>You pat the spot next to you, and she hops up as well
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>Your arms wrap around her barrel, pulling her tightly against your chest
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>You hear her inhale deeply and feel her shudder
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>....this is her first time
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>Your leg shouldn't be that wet
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>She stays still, like a spooked deer, just breathing in deep
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>Whelp. So much for her leading
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>You cup her chin in your hand, raising it up to look her in the eyes
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"Take off my shirt."
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>Her horn lights up, and you shake your head
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"Mouth."
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>"O-oh..."
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>Her horn powers down, but glows softly - she is really turned on, poor dear
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>Her lips find your buttons, kissing them open
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>As her muzzle trails lower, you lean back, giving her plenty of access
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>Soon your shirt is fully open, her breath hot on your belly
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>You slide out of your overshirt, tossing it onto the chair
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>She moves down to open your pants, but you stop her with a hand on her neck
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"Lay beside me."
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>She nods, wordlessly stretching out beside your body
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>You she stares into your eyes as you slide out of your pants
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>Alright, time for the... hard conversation
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"Now...Miss...You wanted a romantic encounter?"
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>She moves her mouth wordlessly, nodding as her blush threatens to turn her permanently red
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"It's only 20% extra to be the small spoon... would you like that?"
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>You trail your fingers along her side, and she shudders
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>"y...yes-"
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>You nod - not at her, but at the enchanted lamp in the corner
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>Your Madam will upcharge appropriately
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"Turn around, love."
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>She does so, her tail flicking madly from side to side
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>Your arm drapes over her barrel, the other sliding under her neck to provide some comfort
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>"Oooh....s-so warm..."
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>You pull her tightly against your body, and she squirms
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"Hey."
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>"Mmm?"
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"I like you, so don't tell Madam..."
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>"T-tell her wh-Oooooh~"
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>You start to gently rub her belly, letting your fingers drag along her fur
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>Bellyrubs weren't usually extra, but you don't need to tell her that now
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>"Mmmm~"
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>She leans her head back, and you nuzzle her cheek, your arm squeezing her slightly
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>You grip her hoof in your hand, rubbing it in time with her bellyrubs
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>Time to make her a regular
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"You're such a pretty pony..."
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>"Aahn~?"
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>You nod against her neck, and she wickers softly
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"So pretty. And nice, too~"
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>She mewls against your touch
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>You lift your hand from her belly for only a moment, and she whines
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>You place it back down, confident in her repeat-customer status
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>It feels....interesting, being a drug to this little mare
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>You keep whispering sweet nothings in her ear as the lights automatically begin to dim
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>She sighs deeply, and you curl up around her, completing the spoon
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"...such a pretty pony...."
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* * *
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>The lamp flashes dimly, twice in the dark room
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>Your signal to leave - her 2 hours were up
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>Maybe you need two cups of coffee before an appointment - this mare was actually pretty comfy
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>Slowly, you slide your arm out from under her, replacing it with the pillow you were resting your head on
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>She inhales deeply, your scent and warmpth still there - so she suspects nothing
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>Standing up, you begin to sneak out of the room - she has it for the night, but not you
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>But a sharp inhale makes you sigh internally
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>"Mmm... Ano-em... sir? Please..."
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>5 more minutes, hmm?
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>"Please....don't leave me alone."
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>oh
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>You walk back to the mare, reaching down to pet her mane
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"Sorry, love. My time is up..."
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>She sighs - sadness and contentment intermingled. "You... you were my-"
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>You silence her by doingthe one thing that you have never, EVER done
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>You kiss her gently
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>Sweetly
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>Like a first kiss should be
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>You break it off, and the silence could deafen you both
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"...next time. Maybe...we'll go for coffee?"
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>"I'd.... I'd like that." she sleepily responds
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>You close the door on her sleeping form and make your way down the hall
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>You knock twice on an unassuming door, and Rarity's magic opens it for you
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>Your Madam sits behind a low desk, an assembly of mirrors and small pools off to the side, showing various views and angles of your room
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>"A 20% upcharge. Very well done, Anon."
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"Hmm. Thanks, Rarity."
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>"I'll....not raise her rates for the next time. I don't think she's like the others."
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>You sit down on the opposite side of the desk - not like an employee, but more as a partner
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>A long silence sits between the two of you, only the sound of the rain and magically-enhanced breathing coming from the mirrors to disturb it
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>"Was that your first?"
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>You start at the bluntness of the question, your mind racing
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"My first what?"
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>Rarity turns to look at you, her eyes betraying concern
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>"Was that... your first kiss?"
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>Oh, uh.
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"With a pony... yes."
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>She closes her eyes, seeming to will back some pain
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>Ugh. That's right, this is a hyper-romantic horse boss you've got here
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>"I-I'm sorry fo-"
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"For what, Rara? For me kissing a mare who just wanted to be held on Hearts and Hooves weekend? Please."
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>"But I'm forcing you into this life! You were an innocent colt-"
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"I wouldn't say innocent, per se"
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>"-before I degraded you! And now look! You're giving away what should go to your Wives to just... anyone who can pay the price!"
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>You roll your eyes, but the sound of Rarity's hoof hitting the desk makes you quirk an eyebrow
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>"I-I'm serious! Anon... Anon this ends tonight. I'm not going to force you into this anymore - if I have to move back in with my parents, so be it, bu-"
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"Rara."
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>Your tone wasn't that of a friend
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>It was that of a predator
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"Rara, you can't force me to do a damn thing. I'm three times your weight-"
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>"Yes, bu-"
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"-your magic doesn't work on me-"
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>"But th-"
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>You lean over the table, and she stops speaking, your face filling her vision
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"-and if you think I'm so stupid as to be taken in by a gorgeous mare..."
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>"Ah-anon..."
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"...and if you haven't figured out why I'm still doing this for you..."
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>Her eyes close softly, a smile spreading across her face
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"...then you really are a silly pony."
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>Rarity leans forward and you don't stop her
229
>her lips press against yours, and you open your mouth just so - letting her tongue in
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>Your hand reaches around to grip her mane, holding her into the kiss for just a little while longer
231
>Breaking the kiss, you're both breathing heavily
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>You grin widely, and she returns it
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>"W-well... if that's the case, I better make sure I take the rest of your firsts - to make sure you remain a proper colt, of course."
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>Her hoof sweeps off the mirrors and paperwork on her desk
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"Yes, it would be untoward if we mixed business with pleasure."
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>You respond, pulling your shirt up and over your head
237
>"Quite, quite." Rarity's magic glows on the light switch, and you reach out, gripping her horn between your fingers
238
>She moans
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"No."
240
>"Oohhh~?"
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"The lights stay on."
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[spoiler]
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>From that night forward, her desk always did have a bit of a wobble.
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[/spoiler]