Hooker Anon [RGRE] [Cuddles] [>Implying]

"Yes, Madam Rarity."
>You sip the irish coffee slowly, letting the warmth seep through you
>"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."
"Does that include my undershirt?
>"What is it today?"
"Tuesday - so a neckless."
>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?
>"I think not, dear. It's not even fluffed yet shows your collarbone, so..."
>She trails off, looking out the window
>You follow her gaze; the lit streets of Canterlot shine below your madame's apartment
>Rain beats softly against the glass, providing a gentle backdrop to your conversation
>You detect a sniffle
"Madam? Madam Rar-"
>"Rarity. Please, Anon... just Rarity. I'm....so sorry that I asked you to do this..."
>She turns to look at you, her face calm, but her eyes a maelstrom of emotions
"Rarara, it's -"
>"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-"
"Rarity."
>She stops her self-pity and looks at you again, swallowing hard
"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?"
>She nods, her lower lip quivering - fighting the urge to sob, trying to stay composed for you
>These pones never could hide their emotions well
"Rara-"
>"Don't."
>You smile and reach forward, petting her head gently
"Rara. My cli- our client will be here soon. Please make sure you're ready."
>Rarity nods wordlessly and hops out of the chair, making her way out of the suite
>This... seems to be getting harder for her
>You are Anon
>And for the past 6 months, under the management of your Madam
>you were the highest-paid, most desirable hooker in Canterlot

>You thumb through your Jane's file
>Rarity may have second thoughts about being a Madam, but damn it if she wasn't good at it
>Let's see
>Once again, a typical newcomer
>Is it a bad thing that you're starting to be a little jaded?
>Good family, 'proper' breeding, used a fake name but didn't cover her cutiemark for the screening photo
>Hm. No kinks listed, nothing on file...
>Marked wanting a "romantic" encounter - that's typical as well. Don't want to show your true colors and be branded a weirdo...
>Probably a mare that wants to 'just try it out'
>They never showed up just once, though.
>A light chime snaps you out of your thoughts, and you slide the file into your messenger bag
>Or as they call it, a coltpurse
>Ugh. Sex innuendos and horse puns everywhere
>Standing up, you make sure your hair is mussed up "properly", your shirt unbuttoned down to your mid-chest, and your demeanor relaxed
>You clear the table of your coffee, replacing it with a bottle of red and two glasses
>You sit down, facing the door, and wait
>That was the 5-minute notice, so at any time you sh-
>*knockknock*
"Come in~"
>You use your deepest, huskiest voice
>You cross your legs and lean back into the chair, smiling warmly
>After all, first impressions are important
>The door handle is wrapped in Rarity's magic, and opens
>Your Jane stands in the doorway, eyes wide
>Yes, little girl. You did just pay a few thousand bits for this.
>She swallows hard, her polished hoof stepping timidly into your parlor
>You smile and open your arms slightly
"Love, do come in out of the rain~"
>No, little girl. You can't leave now.
>She keeps her eyes locked onto your frame, drinking in your form in all the ways her father told her not to
>As soon as her tail clears the threshold, the door silently closes on her, an all-but-inaudible click signalling her time has begun

>She keeps walking towards you - slowly at first, but soon she adopts a more natural gait
>"U-uhm... G-good evening, sir."
>Proper breeding still coming out
>Cute
"Good evening, M'lady. Please, sit - I promise I won't bite."
>You smile, making sure not to show any teeth
>She nods and does so - and you lean forward, pouring her a glass of red
"It's a horrid night out tonight. Did you have a good trip over?"
>"Mmhmm...."
>She stares at the drink you poured - or is it your hands? - and you chuckle
"It's just a normal, red wine. Or would you prefer a port...?"
>"Oh! Ah-n-no, this is fine. I just..."
>You don't fill the silence
>"...I-I don't typically do this kind of stuff, you know? I'm just, just try-"
"Love."
>She quiets up so fast you're sure you hear her teeth clack together
>You won't get a tip if she stays this stressed out
"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..."
>As you speak, you see her visibly relax
"Don't judge yourself."
>She takes the glass in her magic and sips it, a soft smile playing on her lips
>"So... so how do we do this, Anon?"
>Your lip twitches
"It's bad form to use real names..."
>"O-oh! S-sorry"
>You hold up your hand
"First time, so it's alright. And, this all depends on if you want me to lead, or if you want to."
>Considering it's her first time, traditional stereotypes will come out so she'll-
>"I'd like to lead, if that's ok?"
>You nod and stand up slowly
>Her ears flat as she realizes just how /tall/ you are
>You bow slightly
"So, what would M'lady want to do with me? Or... is the better question..."
>You drop your voice again
"What would she like to do to me~"
>Your jane blushes hard, putting the glass down on the table with a forceful *tok*
>"Let's...the bed?"
>She gives you another order-question
>Less and less you're sure she's ever been with anyone before...
>You'll bring that up on her next visit. Or the one after that

>She wraps your hand in her magic, and it fizzles out
>"O-oh! I uh-"
>You recover for her, placing your hand on her withers
>She clears her throat and 'leads' you to the bed
>Looking up at you, you nod softly and turn around, sitting on the bed
>You pat the spot next to you, and she hops up as well
>Your arms wrap around her barrel, pulling her tightly against your chest
>You hear her inhale deeply and feel her shudder
>....this is her first time
>Your leg shouldn't be that wet
>She stays still, like a spooked deer, just breathing in deep
>Whelp. So much for her leading
>You cup her chin in your hand, raising it up to look her in the eyes
"Take off my shirt."
>Her horn lights up, and you shake your head
"Mouth."
>"O-oh..."
>Her horn powers down, but glows softly - she is really turned on, poor dear
>Her lips find your buttons, kissing them open
>As her muzzle trails lower, you lean back, giving her plenty of access
>Soon your shirt is fully open, her breath hot on your belly
>You slide out of your overshirt, tossing it onto the chair
>She moves down to open your pants, but you stop her with a hand on her neck
"Lay beside me."
>She nods, wordlessly stretching out beside your body
>You she stares into your eyes as you slide out of your pants
>Alright, time for the... hard conversation
"Now...Miss...You wanted a romantic encounter?"
>She moves her mouth wordlessly, nodding as her blush threatens to turn her permanently red
"It's only 20% extra to be the small spoon... would you like that?"
>You trail your fingers along her side, and she shudders
>"y...yes-"
>You nod - not at her, but at the enchanted lamp in the corner
>Your Madam will upcharge appropriately
"Turn around, love."
>She does so, her tail flicking madly from side to side
>Your arm drapes over her barrel, the other sliding under her neck to provide some comfort
>"Oooh....s-so warm..."
>You pull her tightly against your body, and she squirms
"Hey."
>"Mmm?"

"I like you, so don't tell Madam..."
>"T-tell her wh-Oooooh~"
>You start to gently rub her belly, letting your fingers drag along her fur
>Bellyrubs weren't usually extra, but you don't need to tell her that now
>"Mmmm~"
>She leans her head back, and you nuzzle her cheek, your arm squeezing her slightly
>You grip her hoof in your hand, rubbing it in time with her bellyrubs
>Time to make her a regular
"You're such a pretty pony..."
>"Aahn~?"
>You nod against her neck, and she wickers softly
"So pretty. And nice, too~"
>She mewls against your touch
>You lift your hand from her belly for only a moment, and she whines
>You place it back down, confident in her repeat-customer status
>It feels....interesting, being a drug to this little mare
>You keep whispering sweet nothings in her ear as the lights automatically begin to dim
>She sighs deeply, and you curl up around her, completing the spoon
"...such a pretty pony...."
* * *
>The lamp flashes dimly, twice in the dark room
>Your signal to leave - her 2 hours were up
>Maybe you need two cups of coffee before an appointment - this mare was actually pretty comfy
>Slowly, you slide your arm out from under her, replacing it with the pillow you were resting your head on
>She inhales deeply, your scent and warmpth still there - so she suspects nothing
>Standing up, you begin to sneak out of the room - she has it for the night, but not you
>But a sharp inhale makes you sigh internally
>"Mmm... Ano-em... sir? Please..."
>5 more minutes, hmm?
>"Please....don't leave me alone."
>oh
>You walk back to the mare, reaching down to pet her mane
"Sorry, love. My time is up..."
>She sighs - sadness and contentment intermingled. "You... you were my-"
>You silence her by doingthe one thing that you have never, EVER done
>You kiss her gently
>Sweetly
>Like a first kiss should be
>You break it off, and the silence could deafen you both
"...next time. Maybe...we'll go for coffee?"
>"I'd.... I'd like that." she sleepily responds

>You close the door on her sleeping form and make your way down the hall
>You knock twice on an unassuming door, and Rarity's magic opens it for you
>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
>"A 20% upcharge. Very well done, Anon."
"Hmm. Thanks, Rarity."
>"I'll....not raise her rates for the next time. I don't think she's like the others."
>You sit down on the opposite side of the desk - not like an employee, but more as a partner
>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
>"Was that your first?"
>You start at the bluntness of the question, your mind racing
"My first what?"
>Rarity turns to look at you, her eyes betraying concern
>"Was that... your first kiss?"
>Oh, uh.
"With a pony... yes."
>She closes her eyes, seeming to will back some pain
>Ugh. That's right, this is a hyper-romantic horse boss you've got here
>"I-I'm sorry fo-"
"For what, Rara? For me kissing a mare who just wanted to be held on Hearts and Hooves weekend? Please."
>"But I'm forcing you into this life! You were an innocent colt-"
"I wouldn't say innocent, per se"
>"-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!"
>You roll your eyes, but the sound of Rarity's hoof hitting the desk makes you quirk an eyebrow
>"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-"
"Rara."
>Your tone wasn't that of a friend
>It was that of a predator
"Rara, you can't force me to do a damn thing. I'm three times your weight-"
>"Yes, bu-"
"-your magic doesn't work on me-"
>"But th-"
>You lean over the table, and she stops speaking, your face filling her vision
"-and if you think I'm so stupid as to be taken in by a gorgeous mare..."

>"Ah-anon..."
"...and if you haven't figured out why I'm still doing this for you..."
>Her eyes close softly, a smile spreading across her face
"...then you really are a silly pony."
>Rarity leans forward and you don't stop her
>her lips press against yours, and you open your mouth just so - letting her tongue in
>Your hand reaches around to grip her mane, holding her into the kiss for just a little while longer
>Breaking the kiss, you're both breathing heavily
>You grin widely, and she returns it
>"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."
>Her hoof sweeps off the mirrors and paperwork on her desk
"Yes, it would be untoward if we mixed business with pleasure."
>You respond, pulling your shirt up and over your head
>"Quite, quite." Rarity's magic glows on the light switch, and you reach out, gripping her horn between your fingers
>She moans
"No."
>"Oohhh~?"
"The lights stay on."


[spoiler]
>From that night forward, her desk always did have a bit of a wobble.

[/spoiler]