Caption Picture: Pauline's New Position

A request that caught my eye today. They wanted a washed up and drunken Pauline who was disgraced out of becoming mayor and ended up becoming a desperate prostitute. Like to think it has a happy ending, but that's up to the reader I suppose.

“Oh! H-hey! Hey there. C’mon in. Yea! No! I’m uh… for sale. Looking for a good time, handsome? I promise I’ll make you feel real… (hic) real good. I don’t even charge that much… oh? I do? Yea, well… you’re right. I did used to be the mayor of New Donk City. Glad to meet an old fan.

“I know I’m not as classy as I use’ta be. My makeup’s shit and I haven’t been shaving and my clothes are dirty… this dumb hat’s the only thing I have left from my time in office. Then there was that scandal with the giant monkey and everything so… well, here I am flashing my tits at strangers for pay… fuck me… er, yea! I mean, you ready to come on in and fuck me, tiger? Great! Just move some of those bottles out of the way for me while I strip down… did you want a strip tease? That’s ten coins extra… no? Okay. Good. I’m not the best at balancing these days...

“Th-that good, baby? You like having that big sweet cock between the washed up mayor’s fat titties? Urp! Scuse me… These jugs are the one thing that’s still worth a damn about me. It’s why your famous, sexy mayor is is on her knees tittyfucking you like you’re some scandalous secretary. Mmmwa~! How’s that? You like having a washed up public official’s lipstick on your dick? The papers would have had a field day with that a couple months ago… now it’s just my fuggin’ job… (sniffle). From a mayor to a filthy street cunt. Hell of a change in careers, huh? Ugh! I’m sorry! You don’t want to hear me talk. Gimme that cock and I’ll shut myself up. Let’s keep these lips busy… 

*SHLUCKKK SHLURRP MMMMPHH… MMMPOP?*

“What? You really think I’m sexy? I mean, I’m a whore. That’s my job to look like a fuckable piece of meat. No more musical numbers or public speeches… it used to be ‘Yes, Miss Pauline!’ or ‘That was a lovely song, Miss Pauline!’ Now it’s just ‘Face down, ass up, slut’ or ‘S-suck it harder, c-cunt.’ (sniff)

“I’m so sorry! I just… haven’t had an actual compliment in a long time now. That means… (urp) a lot to a dirty slut like me. But you didn’t pay good money just to hear me bitch and moan… well, maybe moan. Heehee! God, I feel like I haven’t laughed in ages… but come on. Panties off, legs open, you know what to do. Come on now. Don’t be scared...

“Nnng!! Ohhh you’re a big boy, aren’t you!? Wha… no! It’s okay! You don’t have to slow down! I’ve had my share of cocks in me lately, but you… uhnnnn… you’re something special. You call me sexy and treat me with respect… it’s been a long time, thazz all. Sorry if I’m staring (unnf!)! I just can’t take my eyes off you! I… no! I’m not crying! What makes you say that!? Keep… ahn… keep going! Use your slutty mayor like your 1-Up whore! Grab these dirty tits and just squeeze while you fuck me harder than anyone else! Yessss, baby! Make your mayor whore sing again!

“Yes! YES! I’m about to… oh my… quick! Hurry! Cum with me! I want to make my number one fan sooooo AAAAAHYES! FUCK! OH FUCK! Ohhhh my god! I've been such a gutter whore for so long that almost forgot what an orgasm felt like, let alone cumming at the same time as someone else. You were amazing!

“What? Oh. The time. Your time is up already? Wow, where did it all go? It went by so fast but it felt like forever, huh?

“WAIT! Please! Puh… please don’t go! I hate this! I can’t stand being a useless slut like this! I was famous once! It’s… it’s really killing me… I hate it in the New Donk ghetto. I need a man like you in my life more than anything. I don’t expect you to have to come to my shitty rundown apartment every day or anything… but I could come with you! Please don’t leave me like the drunk old cow I am! I’m begging you! I’ll give you everything! My money, my clothes, my body… you’d never have to pay for sex again! I’ll be your slave just to get some love and affection for once! I… I need you! Please don’t go! Please, oh god please don’t!! I’m naked and on my knees, the laughing stock of all the whites in town! I just met you and you’re the one good thing in my life, and I really could use an extra life right now. Just please...

“Let me be your one up girl.”