Before the lights went dark, she took one last look around. The room was still filled with designer clothes, all prepared for tomorrow’s event at the New York Fashion Week. It was only a short glimpse, but enough to tell she would never forget this night.

He was mid-forties, typical New York banker by the looks, and she was prepared for a one-night stay with him. What she was about to do wasn’t exactly legal. After seeing other students serve as escorts, making tons of money in one night, Alyssia thought she could do the same.

Of course, everyone knows what it means to be an ‘escort’. The rules are clear, payment is for time, anything beyond that is between two consenting adults. And to make a client come back, he had to be a very happy person when the night was over. If others could do it, why not Alyssia?

He arrived at the hotel a few minutes ahead of the agreed time to check in. Nothing unusual. Quite to the contrary, he was well known at the hotel. As a Wall Street fund manager, he frequently spent the night in the city. Sometimes over at the Meatdistrict, and when there was a bit more time, he preferred the East Village.

It was a good week on Wall Street and he deserved a reward. The girl on his go-to escort page was new. Blonde, tall, and an amazing body. There wasn’t much of a description, except that she was European and like dates ranging from tender to rough. Her fees per hour were higher than the other girls, but nothing Jack couldn’t afford. A night would set him back a few grand, no more than a day’s work.

The room was his usual one. His assistant had brought the suitcase earlier in the day. Now all he had to do was wait for her.

The phone rings, “Ms. Alyssia is at the reception for you, Sir?” Swapping millions of dollars between different investments in a single day is a piece of cake for him, meeting a new girl not. He is nervous.

A knock at the door. He opens quickly.

‘Fuck, she’s hot!’ His brain temporarily freezes up. She is more than he had ever expected. Totally out of his league, but money can buy anything in this town. He looks at her for a while.

Blonde hair, some curls, a light coat, beige, and an expensive designer label. Her boots are to die for. Tall heels and the top disappearing below her coat. Her smile is a bit shy but focused. Nothing fake about it. She just looks at him and seems more than pleased with what she sees. Jack tries to stay in good shape, and for his age, he has had no complaints yet. But then again, for the money he’s paying, any woman would be nice to him.

While Jack still tries to unscramble his brain, Alyssia takes off her coat. She intended to make a statement. A blue latex catsuit, together with the knee-high black stiletto boots. For her, she couldn’t waste any time establishing herself among the high-rolling clients. The competition was fierce and she was the new girl.

It was more than obvious that Jack had temporarily lost his voice. Good for Alyssia. She wasted no time to get right down to business. That meant counting the money on the nightstand first. He wasn’t very discreet. Neither was Alyssia. She counted right in front of him. One thousand, two thousand, three thousand, four thousand, and five thousand.

She looks disappointed. Her smile gone and Jack embarrassed. That was his regular rate, but then he had never been with someone like Alyssia. “I’ll make you happy if you make me happy, isn’t that what we both want?” She quietly whispers in his ear.

Jack got the message, he really needed to have sex with her. If she was anywhere near as good in bed as she looked in her amazing outfit, then this was going to be a night for the ages. ‘Fuck it’, he thought, he was going to pull out whatever she wanted. Fortunately, he had some extra money with him just in case.

Alyssia falls back onto the bed, her legs spread, arms behind her head. She looks like a goddess. The sparkling skin, the perfect body, breasts that looked almost to perfect to be natural. Everything Jack had hoped for and then some.

He pulls another $1000 out of his wallet and places it by the nightstand. “Are you happier now?” Alyssia has him wrapped around her little finger. This was going to be a good night for her.

She grabs his tie, pulls him down onto the bed, and starts massaging his cock. The bulge in his pants had been rock hard from the moment he saw her. She was his type and more than eager to keep her happy.

“Well, I’d be happier if I could see what’s behind door number one, but your wallet is still way too thick.” She plays him like a toy. Not long and he has another $1000 on the nightstand. Now Alyssia is happy.

Her smile lights up the room and Jack relaxes. She unbuckles his belt, takes off his shoes, and pulls down his suit like a cheap pair of underwear. Those were probably part of a super expensive designer suit, but cost no more than he was going to spend on her this evening.

“Let’s order a drink, while I get a few items ready.” Jack picks up the phone, half-naked, and orders a bottle of Dom Perignon. “Two glasses, please.” As if the front desk didn’t know. He always gets the same drink. Always for two.

While Jack was busy, Alyssia placed her items within easy reach. She walks over to Jack as he hangs up the phone and gently pushes him against the floor to ceiling window. Some lube in her hand and she begins to stroke his cock. The phone call was an unfortunate interruption.

She goes down on her knees, continuing to massage his cock until it is nice and hard again. Two hands are her specialty. One around his shaft, the other gently tugging on his balls. During the entire time, she never loses eye contact with him.

She has no intention of letting him come this early in the evening. Her stroking is slow, her tongue just barely touches the tip of his dick. His balls are nice and plumb. If Alyssia has her way, they won’t be for long. But not before he empties his wallet.

Jack still can’t believe his luck. There is this gorgeous woman, treating him like he’s the only thing in her life that matters. Her eyes are a deep blue, with a soft edge to them. Just a little make-up, nothing that distracts from her natural beauty.

And her hands are soft as silk. He would normally close his eyes and just enjoy the moment, but she keeps looking at him. Almost pleading with him. She wants more. More of his cash. Not even an hour into their evening and her price tag had gone from $5000 to $8000. But something told him it was going to be so worth it.

He wanted her. So badly, he didn’t care about the money. What he cared about was leaving her wanting him. “Wait, I have an idea.” This will make you very happy.

He picks up the phone again, Alyssia couldn’t hear what he was saying. His grin suggests he got what he wanted. Now Alyssia is curious.

“Do you like fashion? I mean really expensive fashion?” She plays along. What girl doesn’t like expensive designer clothes. It was not lost on her that Fashion Week was in full swing, though most of the action was in SoHo. “Let’s go up to the Penthouse.” Jack is still trying to impress her.

The elevator door opens to a dark room. Jack takes her by the hand and leads the way. Then he finds the light switch.

Alyssia is absolutely blown away! She would never have expected a Wall Street guy like Jack to have any interest in fashion, let alone know where the tucked away shows are held across the city. And yet, she found herself in a perfectly displayed haute couture collection worth millions.

Money turns Alyssia on. Anything that is expensive turns her on. Forgotten is the wallet that he so conveniently brought along. Instead, now she wants him to fuck her. Yes, right in the middle of all this luxury, she wants to be his whore. No more games, just plain lust.

Jack looks a lot better now. And his body is hot. She opens the zipper between her legs and makes him touch her. She is dripping wet. There are few words exchanged, just enough to make it clear that now Jack is the one in charge.

His cock gets harder by the second. Alyssia is now completely overwhelmed; Jack pushes her to the ground. His cock feels good inside her. He is rough, just like she wants him to be. The hard stone floor feels like velvet to her. Harder. Alyssia is no longer herself. She’s now given up all control and Jack has turned into a sexual monster.

She is on her back, legs spread. “Fuck me, Jack, fuck me hard!” He doesn’t need any invitation. He’s found her soft spot. Pounding his cock deep into her, he pins her to the ground, slaps her around just because he can. He’s stronger than she is, she would stand a chance trying to get away.

“Do it again, slap me, hard!” He can’t believe she likes what he does. As if he’s on drugs, he keeps fucking her cunt and hitting her cheeks hard. He doesn’t want to hurt her, although the thought of leaving a bruise behind turns him on. He’s usually not like this.

Alyssia is so engrossed in the moment, she wants more. More money, more sex, more abuse. She hits him back, not thinking what this would do to him. Jack had never fucked any of his escort so hard before. Alyssia wanted it to hurt, and he wasn’t going to disappoint her.

She stands up, like a doll, hands against the wall. Now he wants to have it his way. He has never fisted a woman before, but tonight was going to be different. One of those dreams he always had but never dared to ask. Alyssia, though, took all his inhibitions away. She was going to take his fist up her cunt one way of the other.

Alyssia is delirious. She loved every minute of his cock inside her, his pounding and slapping. Now that his fist pushes hard into her pussy, she collapses. Her body is worn out. She doesn’t realize was how far his fist has already entered her. There was no collapse, just a final push before his fist deeply penetrates her worn-out cunt.

He dictates what happens next. Alyssia has no other clients. This is her first time and she can afford to be careless with her body. “That’s all you’ve got?” She begs him to fuck her in the ass, or better yet, double fist her. She wanted it all, no matter the consequences.

“Your wallet for my body, deal?” She says in a rambling tone, more confused than thinking. Jack is nowhere near done with her. She wants to be abused, hit hard, fisted, double-fisted! There’s no turning back. He gives her everything she wants.

Alyssia’s body rocks under an amazing orgasm. Jack’s hands deep inside her. He feels her body fighting against his fists, her muscles gripping around him until they grip and release by themselves with her body lying limp on the floor.

Alyssia was in heaven. She looked happy, satisfied. Jack was busy jerking off and unloading his cum over her body. It was a massive load. He did have a good time. And he made her happy.

Before leaving the scene, Jack pulled out the remaining $100 dollar bills. “Here, clean yourself up. We wouldn’t want anyone to think your just an expensive whore.” She looked around one last time before Jack turned off the lights.

Wicked Wednesday
Masturbation Monday