Your first day as a hooker

You’re early at your meeting place – the outdoor area of an ice cream parlour in a busy park not too close to your place but easily reachable. It’s hardly after noon, apparently he has plans for the evening – whether with his family of in is function for the party. He doesn't let that stop him from meeting you earlier. You smirk.

You're dressed relatively modest. Which doesn't mean too much, the clothes you bought for yourself since you’re a woman all emphasize your new body the most flattering way. None of them are not made to make you looks sexy. But some would be appropriate if you offered your body to drunks in a back alley at night instead of in a public park in broad daylight to a leading politician. You wouldn't mind showing off your body like that here, you bought the clothes after all, but you feel your first – client prefers to be publicly seen with women he can justify to his voters.

You smile and take sip of your milk shake. You got here early, could not sleep much and did nothing productive all morning. You took your day of from all other liabilities. There's no way you could have focused on work or anything else productive right before your first job as a call girl.

You sit in the warm midday sun and enjoy enjoy the breeze, musing about where you are and what you're doing, It’s surprisingly comforting train of thoughts. You only sense a vague hint of your old self objecting to you selling your new body. Let alone to a man you can't say you ever found sympathetic. But you’re new self has settled into doing whatever you feel like. And it likes sex - in a way you couldn't even understand when you were still a man, this new body has so much more to offer than when you were so damn focused on your dick – you like money and you like the power your body gives you over men so that they give you sex and money. And it does. The gem around your neck warms your chest. You remember believing you were in control when you gave a woman money, but you were wrong So wrong. The men paying you are weak and pathetic and fully under your thumb…

Speaking of the devil.

You smile reservedly at your john as he arrives at your table. He looks a bit flushed, slightly sweaty, his bald head glistens in the sun and he’s out of breath. You stand up leaving the decision of how intimate your greeting shall can be to him – he shakes your hand.

“Good morning, Miss... “

You giggle.

“Gypsy will do.”

He looks around and you smile to calm him.

“Nobody will hear you call me that, were’ just having a harmless conversation in the a café.”

He nods and sits down. Not losing much of his obvious nervousness.

He orders a coffee, milk and two sugars. Classical. No latte or cappuccino experiments.

You talk in a low voice to reassure him you’re not being overheard.

“This isn’t your first time with an escort, is it?”

“No... I mean... yes… I mean.. I’ve had girls in the red-light district, brothels, even street hookers. All very anonymous and behind closed doors…..”

You have to hold yourself back to not ask him what his conservative Christian voters would think about that.

“I see. May I ask what made you – change your habits and ask for my company eve it it means being a bit more – public?”

He just looks at you. For a long time.

“You’re so… I don't even know. Beautiful, of course the prettiest dancer in hat club. If not in the whole town….”

You smile and try to suppress a blush. The curse really did give you a body to impress. Or let you pick one.

“But that's not it. You're confident, strong, you're not like those other women who hear who I am and just start flattering me. I felt your strength on the stage, how you were in control of everything and I was… stunned. And the way you talked to me afterwards…”

You tense a little. You’ve been thinking back to that all night, quite daring for your first contact with a paying customer. Apparently it didn't scare him of, and yet...

“That was...exhilarating. Nobody talks to me like that. Not in may party, and especially not girls I pay.”

His eyes glaze over dreamily. Apparently it didn't just not scare him off, it seems it was the major turn on. You raise an eyebrow. That changes a couple of things as to the way you planned to service this little man. How would you even start with… you take a breath. Maybe just let your female instincts take over. You have some good experiences with that.

You smirk at him.

“Hmmm. So you liked that, huh?”

He fiddles with his spoon.

“Uh,.. uh... yes, Gypsy… I reall..”

“That’s Madam Gypsy to you!”

“Huh?”

“You apparently need someone to show you your place. And if you want to warn a chance to earn the honour that that someone is me - you’ll show me some proper respect and call me ‘Madam Gypsy!”

“But you said…”

“Don’t tell me what I said, just do what I tell you! Or do you want me to make you?”

You take your spoon and let I slap on his hand, not hard but enough to make him drop his.

”No… I mean, yes.. I...”

You chuckle.

”You seem a bit confused, little man. Do I have to keep my instructions more simple? I thought you were smart, given your position and job, but apparently being smart was not required for your career, huh? Probably all just connections.”

“I… I guess so.”

He takes a second to add:

“Madam Gypsy.”

You nod.

“Makes sense. You’re a bit stupid. Morally bankrupt, obviously, whore-mongering moraliser that you are. Not charismatic either, you sad little man. And it sure wasn't your good looks that got you were you are.”

You dare to take a leap.

“You look and act like a little pig.”

He blushes. Hard. And doesn’t say a word. Seems you judged him right and got him hook, line and sinker. You chuckle.

“Ah, don't feel to bad, little piggy. You got money and you got power, for some reason. That speaks for you. Well… hm... The only thing, actually as far as I know. But still that can go a long way.”

You pat his hand.

“And maybe we find some other qualities in you, that are hidden a little deeper. There's still a chance. You know what I like in a man? Other than him being rich and generous?”

“N… no, Madam Gypsy…”

“Humility. Obedience. Submissiveness. Honestly, not character traits you show to the public, little man, but maybe we can find some hidden gems in you!”

“Y… yes, Madam Gypsy.”

You smile. Time to bring in the catch.

“You ma also call me Mistress. It's a bit more convenient, right?”

“Yes. Mistress.”

“Excellent. Tell me, how much time yo you have?”

”I… have to be at a ceremony at 8. I'm getting an award from ‘Concerned Mothers United’ for my form stance on traditional gender roles…”

You laugh out loud. You have no idea why he felt the need to blabber about this right at this moment. Maybe to assure himself he's still one of the good conservative guys.

“Alright then…."

You take his tie and pull him towards you.

“Looks like I got my traditional man until about seven, huh. IF I decide to let you go then. You better be good boy and get me into a generous mood. That’s about 5 hours, give or take. That'll be 1000 bucks. In advance, of course and cash.”

He's looking at you dazed. You really enjoyed that, determining the next hours for him, not bothering to ask but just present your decisions.

He nods.

“And we're going to a good hotel, not a cheap fleabag.”

“Yes, Mistress.”

“Alright, pay the bill, we're not wasting any more time.”

He does so, cash, adding a 5 % tip until you intervene.

“Make that a 50% tip, honey.”

He blinks, then nods and adds a banknote the bill as the waitress smiles at you warmly.

“Thanks a lot, Ma’am.”

You drive some minutes in his fancy car- really fancy - to one of the better hotels in town. One he’s actually known in, which makes him sweat profusely.

“Relax, little piggy, they're professionals here, they know to keep their guests' secrets.”

“Of course, Ma’am. Don't worry, Mr. Chairman, what happens in our hotel stays in our hotel.”

The receptionist smiles – which could also be interpreted as a mean smirk as she addresses him by title, making it clear that she recognised him and hands you the key. Making it clear she also understands the power dynamics at play.

“Will you stay for the night?”

You shake your head.

“I don't think he'll last a whole night. Until when do we need the room, piggy?”

He blushes hard enough to make his head seems to explode.

“Only until seven... at best.”

You take the elevator to your floor, open the door with the key card and enter the room.

You stand still and look at him expectantly. He’s staring back, trembling. Doesn't get it. You cough.

“The only reason I'm bothering with you so far?”

Dumbfounded stares.

“Gee, you’re REALLY not the smartest. The money!”

“Oh. Right. Sorry, Mistress.”

He jumps and take his wallet out of his pocket, counts five votes of 200. You nod.

“On the dresser!”

Meanwhile you send a text to your boss the strip club – you don't think you need backup, this little man is no danger to anyone but his own dignity, but you won’t want him to worry.

You take your extra time with the message, letting your john stand in the room lost and waiting. Let him get used to who’s in charge.

You check our other messages, go to twitter and eventually put the phone down. You smile at the the thought that you're on his paid time now.

"OK, then. Get undressed!”

He’s hesitating, Despite being aroused, this is a lot different than his previous experiences with paid women, he’s clinging to the procedure he knows. Which didn’t include HIM getting naked first

“Alright, let me me lay own the rules. Just this once. I don't intend to repeat myself!”

“Y.. yes, Mistress.”

"You will do what I say, when I say it! No ‘buts’, no ‘maybes’. And I will decide what you get out of this meeting. And let me be frank, I don't like you. I never liked you when I only knew you from the news - your politics are appalling, your ‘values’ are medieval. But now that I know you’re also a creepy little hypocrite and don't even adhere to your own 'values', I like you even less. So I have zero interest to make you happy. What I care for is to give you what you deserve, what you need. And I alone decide what that is. Clear?”

He trembles, but then nods.

“Y.. yes, Mistress.”

“Excellent. That gives you a little benefit - you may chose a safeword.”

You grin. Of course you would have given him a safeword either way. Your old male self would maybe have gone into a BDSM session carelessly and stupid, as a woman you’re in total control and never lose your ratio over to your lust. Women are just much more in control of their emotions. But let the small man believe this emergency exit only exists due to your generosity.

“Safew…”

“You know. I won't care much if you beg me to stop or cry or say 'no' until I'm done with you. But if you really really want to stop, use your safeword and I will. I will also never see you again, because you'd be even weaker and more pathetic than I thought, but it you'd save your ass from my wrath."

He sweats.

“I…”

“Pick something you won't forget and that you wouldn’t ever say when you get exited.”

He blurts out a name – the name of the current head of government. You chuckle.

“That’s a statement. OK, get on with it.”

He looks at you questioningly

“I told you I don't like to repeat myself!”

He wrecks his brain for another second. Really not smart. But eventually he remembers your last order it and takes off his suit jacket and tie.

“Nice and slow, little piggy.”

You sit down on the bed.

“You saw me strip for you, it’s time you return the favour. Not that your fat, ugly body excites me ONE bit, but it’s just fair, don't you think?"

“Y.. yes Mistress.”

He slowly drops his jacket, and starts to open his shirt.

His movements are clumsy, trembling, as unsexy as possible, but you do feel you're getting aroused. Not from the body or the man. You could ignore the body if the attitude was confident and strong, not as weak and pathetic as this “man”. But sitting here having full and total control over a man feels - exhilarating. Teaching him humility is is better than sex. and he really reminds you of your old male self. Which makes it weirdly better.

He takes his shirt off, revealing a white undershirt, fitting tightly over his belly. Clumsily takes of his shoes and in a parody of sexiness opens and drops his pants and stands in front of you in his blacks socks white briefs and undershirt. A pitiful sight, made to kill every erotic mood. For most women. But you feel you're immensely enjoying his humiliation, his shame. This is great. You could do this all day.

“All of it, sexy!”

He takes off the short and resentfully drops the underpants in front of you and stand there like a bump on a log. Struggling not to cover himself.

You look at him with a smirk. For a long time. Longer than you feel like, personally, but you know every second you intensely, judgingly eye him deepens his humiliation.

He’s not impressive under his clothes. His belly, his thin legs, his hairy chest. Looking his age and having nothing in terms of personality to make up for it.

His cock… hangs limp between his legs like a tiny shrimp. Might be a grower, but even then your increasing experience in cocks since you're a woman lets you doubt it'll grow to more than an average size. IF he even gets it up.

Eventually you let out a sigh.

“That’s embarrassing. I had been hoping you at least have a cock to make up for any of… that….”

You gesture into his general direction.

“But that's as limp and unimpressive as the rest of you, little man."

“I… I'm sorry, Mistress.”

“You better be. Your little dick is just as much a disgrace to mankind as your little mind and your little morals. Your sheer existence is making humanity worse by a notable amount!”

He blushes and lowers his eyes.

“On your knees, worm!”

He does it immediately, obviously glad the time of just standing and being observed is over and he gets a clear command to take his mind off his humiliation.

“Crawl over here!”

He does.

“Kiss my shoes!”

You're wearing simple flat ballerinas. Wish you'd put on boots and heels, but they'll have to do. Next time. He kisses them as you look down on him smiling.

"Are you sorry for burdening us with your existence?”

“I’m sorry, Mistress.”

“You do realize, you’re hindering strong women like me to achieve our best with your stupid ‘traditional values’?”

“Yes, Mistress.”

“Will you do everything I tell you to do to repent?”

“Yes, Mistress!”

You slip off your shoes.

“Carry on!”, making him kiss your bare feet, the soles, lick between your toes. You giggle. That actually feels nice, you could get used to a man grovelling at your feet. Eventually, after a long time, you let him kiss up your legs, even your knees, but there it ends, with a slap on his cheeks you show him his limits.

“That's as close as you'll get to my sanctum, little man!”

You tease him by rubbing your crotch through your shorts.

“Get up!”

He does, standing in front of you and you snicker as you see his cock now erect and hard. Not big, though. You’re not surprised to find it way below average of what you experienced so far in your days as a woman.

“Pathetic!”

That it is pretty much the size of your dick when you were a man doesn't stop you from saying that. On the contrary. It kinda feels good to be able to be so honest to yourself and call the cock you had what I really was.

“That’s all, huh? Does it get any bigger?”

He shakes his head.

“No, mistress.”

You snicker.

"No wonder you made it far in your job, you have SO many things to compensate for. No brains, no personalty, no moral compass. And no dick to speak of…”

You slap the hard cock in front of you, making its owner wince.

“But unimpressive as this showing is, it does mean you enjoyed what I did, huh?”

He remains silent.

“DID you?”

You grab his Wiener and grip it firmly.

”YES. Yes, Mistress I enjoyed it!”

“Why?”

“Be...because I’m a pathetic worthless little man who deserves to be punished by a... strong.. beautiful woman!”

You smile and let go a little.

“Indeed. Well said. Self awareness. Good first step!”

You slap his balls now, hanging below the tiny cock like a shrivelled bag of grapes. You giggle as he winces. This is fun. You lick your lips. Take a look inside of you. What the thing {first_name-male} would have feared most in this situation? You smirk. Cruelly. The thought of your old male self in this situation is in no way unpleasant. For some reason you really enjoy it actually. You wonder if that's because you fully consider him a different person by now or if you actually would have enjoyed this as a man? Did you harbour such urges? You never admitted them to yourself that much is certain. Either way. Now you're on the other side and THIS you will enjoy.

You grab the small balls firmly and squeeze them hard. His wincing turns into a groan then a scream as his knees weaken and he falls down in front of you.

“Imagine you men considering yourself the stronger sex, huh? Just one tiny little pull on the right lever. That really didn't take any strength at all. ANYONE can do it. And you're a grovelling, crying peace of dirt in our hands.”

You laugh as he groans at your feet.

“Get back up, maggot, I’m not done with you!”

He does, hesitantly, shakily.

“Bend over. Hand against he wall. Spread your legs, ass out!”

“Please… Mistress…”

“NOW!”

He turns around and spreads his legs, bent over. His flabby hairy, pale ass is facing you, but that's not what you care about, between his legs his balls dangle and he cock, turned limp swinging. Easy target.

You make a fist and take a punch at the dangling balls. He howls and tenses.

“Please, Mistress. Mercy…!”

You chuckle. No safeword. You take aim, and now kick with full ****. His scream is blood curdling, high pitched like a girl and now choked with tears. He’s crying.

“Pl.. pl... please. Stop. I… hu... hurts so bad, I can’t…”

Still no safeword, that guy can take a beating, gotta give him that.

You kneel behind him and punch his balls gain, this time from below. His scream is choked as he falls to the floor, rolling into a ball of pain. You listen closely, but none of his sobbing pleas sound like his safeword, so you wait a few moments, turn him to his back and spread his legs. Put your foot on his limp dick in his belly and pout your whole weight on it.

He groans and wriggles, screams as you take another kick between his spread legs. When you kneel down and take his now swollen black and blue balls into you hand, he winces, even though you just caress them gently in way he would have very much appreciated just few minutes earlier. You snicker. Ho easy men can be brought down. Such pathetic creatures.

You take his cock into your hands, also black and blue now, feel it. No abnormal swelling, noting burst or broken. He'll be fine. Eventually. You start rubbing it, massaging his balls, making him groan and moan and grunt in pain more than in pleasure. As it should be.

“You were an obedient little piggy. Not bad. Took the punishment yo deserve like – well not a man, more like a crying little boy, but that's all I can expect from a loser like you, right? You deserve a little reward.”

You keep rubbing his cock until it gets hard again.

“I think it looks better in black and blue. Suits you!”

You grab it hard, with one hand, firmly kneading his tortured balls in the other. It must be agony, his groans definitely sounds tortured more than lustful, but he better get used to that.

“Please, Mistress… it hurts…”

“Of ours it does. You don’t think you deserve pleasure without pain?”

“No, Mistress.”

"Then be a bit more grateful, you worm”

You grip his balls firmer, making him scream. And cum. You hadn't expected that, but apparently the pain pushed him over the edge, not the kind rubs you had for him. You’ll keep it in mind.

A little stream of thin cum – well it doesn't exactly eject, rather drip out of his brusied cock and trickles down your hand.

“Your orgasm is just as pathetic as everything else abut you. At least you’re consistent...”

You let him lick of his watery cum from your fingers and thank you for your kindness in letting him cum.

He spends about another hour on his knees licking your feet thanking you for the deserved punishment you gave him while casually spanking his ass with his own belt. It'll leave some marks, but it's not too severe. You'll save a proper spanking for another day when he's not used to pain from Cock and Ball **** .

Eventually you get bored and order him to get dressed.

It’s not even four, but he doesn't object as you put he whole 1000 he paid for the session until seven into your purse. You decide how long he is granted the honour of your presence and he knows it.

“Can… can I… would you.. allow me to…”

You look at him.

“Stop wasting my time, piggy. Are you trying to ask me if I'll let you serve me again?”

“Yes, Mistress..”

“You were - adequate. Leave me your number, I’ll inform you when I feel like teaching you another lesson. Don't try to contact me, understood?

“Yes, Mistress.”

He eagerly hands you his business card.

“But you can earn yourself some of my good will if you can tell me he name of someone next time who you think deserves my punishment as much as you do and would be willing to take it. And pay for it, of course. You’ll get me some contacts into your circles, I feel there's a LOT of need for some discipline!”

“Uh… yes, mistress.”

You see the gears in his head turn… You're sure he knows a lot of perverts like himself in his conservative party. Church. Rich neighbourhood. Lots of weak pathetic men who yearn to give you their money to get humiliated.

You leave the hotel, giving a nod to the receptionist smirking as she sees you. You decide to frequent this place regularly if this business proves profitable. Maybe give her a share. Good connections matter.

He's walking hunched over, wincing every few steps. His balls will remind him of you when he takes his award from the Concerned Mothers.

You let him drop you off at he strip club. You won’t dance here any more. Or ever really, as much as you enjoyed that it was no match for the rush of power and excitement you felt today. You have found your calling, your place in the world as woman. As for your former boss - he can keep getting you clients for his share. Special clients that pay extra for your special service. Until word of mouth has made you independent from this not quite pimp.

As you enter the club, it only briefly occurs to you that all your grant plans leave no room for you becoming a man again on Sunday… You shrug. Maybe you don't want to any more.... You never felt so good as a man as you do now. Never been so financially well off, either. Is getting that tiny cock back really worth losing any of this… you'll need to think on that very hard. But you can make preparations for this new life anyway. No harm done.