Lily was a good girl. At least if you asked any of her family and closest friends, that is what they would say. Lily would have said that about herself too, until recently that is. She never had a one-night stand, had only had a few boyfriends, and did not sleep with any of them right away – they all had to wait a “respectable” amount of time before she would let them between her legs. But, Lily had a secret, a secret no one knew … no one except him.

The woman sitting in the back of the taxi was certainly not dressed like a good girl. She wore a sexy black cocktail dress. It was short, leaving plenty of the long legs from Lily’s lithe 5'9" frame exposed. The dress was backless, so no bra. Strappy velvet heels completed the “sex on legs” look.

It was a hot summer evening by London standards so her legs were bare, no stockings. Definitely not the look of a good girl. She could pass for a young London model out for a night of partying, sure. Or, maybe a high-class escort. This last thought brought a noticeable wetness between those long legs, which was a problem because she was not wearing underwear; no panties, because that was what he requested. Definitely not a good girl. Her pussy leaked some more. How did he do that to her even when he’s not here? Lily thought to herself reaching up to touch the discreet gold choker chain around her neck with the “O” ring at her throat. It’s a symbol he had said. Since they had started their “arrangement,” mere thoughts of him – and what they did together – made her wet in a way that was completely new to her.

Oh, and there were many things that were new to her. Besides the dress, the sexy shoes, the choker, and the small clutch she carried, Lily wore only one more adornment: a bejewelled butt plug carefully inserted into her bum. Definitely, not a good girl. He had taken her anal virginity soon after they had met. They had built up to it, but it was still difficult. He’s large in a way that feels great in her mouth and in her pussy, but they had to go very slowly in her ass. It hurt, a lot, but Lily didn’t stop him. He was barely able to fuck her there, but she still came. She came very hard. Yes, he had opened her to many new things and she liked it. Lily liked it because deep down, she's a slut. This was Lily’s secret.

Lily had always fantasised about being taken, owned, degraded, and dominated by a man. She knew she was not the only woman with these feelings. The desire that made her feel most guilty, however, was the idea of being paid for sex. But, how does a good girl ask for this?

The idea was a huge turn-on for her, but being an escort was completely out of the question. So, Lily was left with sneakily searching for “rough” and “BDSM” porn, and reading erotic stories of girls who reluctantly prostituted themselves – all of which made her wetter and gave her more intense orgasms than any of the fumbling around with past boyfriends. She assumed these feelings would remain just fantasies, never to be realised in real life, until one day when she learned about “sugar dating.”

The idea was simple: a dating app, but for older wealthy men – the sugar daddies – to meet younger attractive women – the sugar babies. The “sugar” was sex for the daddies and money for the babies. You started out with PPM – pay per meets, and then moved to an “allowance” if the relationship was successful. It was not strictly prostitution since it could be exclusive and you mutually choose each other, but it was close enough to make Lily moist at the thought of actually doing it. Although, she doubted at the time she would actually do it. She was a good girl after all. Still, it was free to set up a profile and you didn’t have to go through with it if you chickened out.

But, Lily did go through with it.

None of the requests to connect on the app interested her and she was close to deleting her profile when she got a request from a daddy to mutually share their private photos. Like her, he had hidden his face in his public profile, but, also like her, he had a private folder that could be shared. He was a bit old for her, but she was attracted to older men. He looked fit even in the photos hiding his face. You could tell he was good looking, but it was one line in his profile in particular that convinced her to click the share button: “…a Dom in the bedroom.”

He was handsome in his private photos, and looked much younger than his stated age. A full head of hair that looked lush. Lily found the grey on the sides sexy. She knew she looked good in her photos: model-tall, an athlete’s body, long dark hair and deep blue eyes. She never had trouble attracting interest from men, so was not surprised when he messaged her almost right away.

When they first started messaging through the dating app, she still assumed nothing would come of it. Then, they moved to regular phone messaging and kept the conversation going. It went on for so long and Lily asked so many questions. She thought for sure he would give up out of sheer annoyance. But, he was patient and his answers were sincere, not just telling her things he thought she would want to hear – including things that might scare her away. It was in these exchanges that there was the inkling that there were some common kinky interests. He made Lily a proposition: take this online sexual personality test and show him the results; he promised to share his results.

They were a near-perfect match. He was dominant, she, submissive. He was a rigger, she a rope bunny. He leaned sadist, she was a masochist. He quizzed her about her expressed preferences for humiliation and degradation, which were new for him, but he still understood completely. At this point, they had to meet.

Lily was beyond nervous for the first meeting. They met for a drink in a public place. They agreed either could back out, no hard feelings. But, if they clicked, they would go back to his place for sex. Lily had never had sex with someone she had just met – he was a stranger after all! And, she was a good girl. How was this even possible? But, they did click, they did go back to his place, and, in spite of the nerves, the sex was…amazing. She had to do it again. 

All of her fantasies were being fulfilled; the money in the envelope discreetly left on the coffee table for her to take – just the idea of being “paid to fuck” making her wet. Learning how to play, “I say, you do” – being his submissive. Gagging on a cock for the first time. Being tied up and teased. Having an anal orgasm for the first time from his fingers. Oh, his fingers! His fingers had given her deep orgasms, more intense than she had ever had before. And, Lily’s favourite, riding him on his couch, his long thick cock stimulating her in just the best way possible. Eventually, Lily gladly gave him her anal virginity, and she can’t wait to do it again. Maybe tonight, he told her to wear her butt plug after all? She had never wanted to please someone this much before.

The taxi pulled up to one of London’s chicest hotels. The dinning room is a Michelin starred restaurant where they are meeting to celebrate their new arrangement. The doorman opened the door of the taxi and helped her out, but not before getting a good look at her legs. She was suddenly very conscious again of the fact she was not wearing any underwear and that she was sporting a shiny butt plug – did he see anything? She couldn’t be sure. The doorman then raced ahead to open the door to the hotel for her.

The dining room was enormous, but the tables were few and spread out. He was seated at the table in the furthest corner. Did he do it on purpose to make her walk across the entire room for all to see? Normally, it would have been the length of the little black dress that would have made her self-conscious exposing so much leg. But, the shyness of exposing her long legs was trumped by the realisation that if the butt plug fell out now – in the middle of this very fancy restaurant – she was sure it would be the most embarrassing moment of her life. The plug held, however, and she was keenly aware that her pussy was dripping wetness down her leg.

He looked good. Classic blue suit, crisp white shirt rakishly opened at the collar, that hair she loved a bit tousled. In her “higher-than-she ever-wore-before” heels, she was slightly taller than his 6’ frame. They kissed on both cheeks and he told her how beautiful and sexy she was. More moisture ran down her leg. Why were they wasting time with dinner? She thought. She wanted him now.

They sat next to each other at the square table and looked out over the dining room. Surprisingly, there were not many people for a Saturday night, but Lily was still conscious of the fact she was the most provocatively dressed woman here. She was sure the few others that were here must have thought she was an escort. Of course, that idea only excited her more.

They toasted with champagne. They were celebrating the next stage in their relationship. No more PPMs. They had agreed to move to an allowance – she liked to think he owned her completely and exclusively now.

Lily is sure dinner was fabulous, but she couldn’t tell you what either one of them ordered. She was so sexually charged by the entire situation that she couldn’t think straight. Why don’t they just go back to his flat and give her the release she needed? It didn’t help that he was discreetly running the fingers of his left hand along her bare thigh sending shock waves directly to her pleasure centres.

After the second course, while caressing her thigh again, he said, “Did you do as I asked?” referring to the instructions to not wear panties and to insert the plug.

She nodded yes.

“Good. Now carefully lift the hem of your dress so your bare ass is pressed against the chair.”

"What? I can’t do that! Someone will see! Besides, I am very wet…” she pleaded in a whisper.

“The tablecloth will hide you. No one is looking. The waiter is far away. Now, do it,” he insisted.

And, she did it. Rising slightly and moving the hem of the dress to just over her buttocks. She could feel her sopping pussy press against the plush fabric of the chair. Lily was sure there would be a stain. She clenched the plug to make sure it didn’t come out. She must have been blushing red in humiliation.

“Good girl. How does it feel?”

“It’s too much. I need you. Let’s go back to your place,” Lily tried to negotiate.

“No need. We have a room here. Let’s skip desert,” he surprised her.

While he called for the check, Lily discretely pulled the hem of the dress back down praying nobody noticed. When they stood up to leave, she used her napkin to hide where she was certain there must have been a large wet spot on the chair, although she didn’t have the courage to look. Despite the embarrassment, she could not think of a time in her life when she was more turned on. She practically jumped him when the elevator doors closed, kissing him with a ferocity she didn’t know she had. He kissed her back and squeezed her breasts. She had one hand holding her clutch behind his head and the other rubbing his cock through his suit. He was hard as steel and felt good in the grip of her hand. She was happy it was not just her that was so aroused by the situation.

They exited the elevator on their floor which was completely deserted, with long corridors stretching in both directions. He guided her to the right with his hand on her back, then he it slip slip to squeeze her ass. He brought his other hand to the front of her dress and rubbed her pussy through the fabric.

“Someone will see!” she worried.

“There’s no one,” he reassured her as he continued driving her wild.

Why were they walking so slowly? Lily thought. She was thankful that the lighting was dim and got darker as you moved further down the corridor away from the elevators. It was darker still in the alcoves of the windows that lined the left side looking at the street below. It was into one of these that he pushed her, grabbing the clutch out of her hand and throwing it on the windowsill so they could make out.

“Did you receive the funds I transferred today?” he asked between kisses.

“Yes,” Lily said.

“Then, I own you. You’re mine. Your holes are mine to use as I please,” he snarled.

This was part of their game. He knew the dirty talk and the idea of money for sex was a big turn-on for her.

“Say it, say I bought and paid for your holes.”

The good girl hesitated, but then the slut moaned, “Yes, you bought and paid for my holes.”

“I own this mouth,” as he plunged his tongue into her.

Suddenly, he lifted the dress to her waist exposing her. She panicked, being naked from the waist down in a public place, but there was no one and they were hidden by the alcove.

“I own this pussy,” he said as his hand rubbed her. She was so slick he easily slipped two fingers inside. She was close to cumming. “I own this ass,” as his other hand tapped the plug in her bottom. His fingers kept thrusting, twirling around her cervix. She was almost there…“I have to got to have you now!” he hissed.

“Then, let’s go to the room,” Lily said.

“No, here… assume the position!”

The position? Here? “Positions” were part of their game. There were three positions. “The” position, position number one, was kneeling, legs spread, hands behind her back. She liked the submissiveness of doing this for him, but not here! In the corridor of a luxury hotel. But, she did it. She slid down, kneeling on the carpeting of the hotel corridor. Her dress bunched around her waist, naked from the waist down, her legs spread, displaying herself for anyone who might walk by.

He pulled her arms over her head and held both wrists in a one-hand vice. With the other hand, he unzipped his suit trousers and fished out his cock. He seemed bigger than normal. Thicker. The foreskin already stretched back and the head a dark red as if it were angry. It was slick with precum.

“Suck it, make me cum,” the command came.

And Lily did. Using only her mouth because he still held her arms above her head by the wrists. She licked and sucked him. She liked giving him blowjobs; she missed it when they weren’t together, but this quickly devolved from a blowjob to a face fucking. He roughly thrust into her mouth. Her head hurt when it banged into the windowsill, but then he moved his free hand behind her head to absorb the impact and also to hold her in place as he sought her throat.

Lily loved the rough treatment. His thrusts were becoming more urgent trying to shove more of his cock into her throat. She had learned to take all of him, but not in this position. The best was lying with her head hanging over the side of the bed; she could take all of him then, but like this, she couldn’t. Not that it stopped him from trying. He would hit the back of her throat and then shove hard. She knew from experience her throat would be sore tomorrow. His movements became frantic. He was close. Then, suddenly, they heard from down the corridor the elevator doors opening.

They heard voices in the corridor and they both froze. He let go of her wrists but grabbed a fist full of her hair with the hand behind her head. When she tried to stand up to pull her dress down and maybe reclaim some dignity that might be left, he held her firmly in place with his cock still in her mouth. If anything, he pushed his cock further into her throat as he shuffled more into the alcove so as not to be seen.

Lily feared she would choke and the sound would give them away. However, the voices grew fainter, not louder. Soon there was silence again.

He peeked into the hallway. “They must have gone the other way.” He started thrusting his hips again, keeping a fist in her hair, as he resumed fucking her mouth. “Now, play with yourself while you finish what you started,” he ordered.

She immediately dipped two fingers from her right hand into her sodden pussy and began making short thrusts. All the built-up excitement was about to come gushing forth. She reached for his cock with her left hand, but he slapped it away.

“Just your mouth, pet,” he said.

The rough treatment was too much for her and she realised she was going to cum. She fell off his cock and tried not to moan too loudly as she finally came; convulsing there on her knees, half-naked, legs lewdly spread in a hotel hallway. Lily felt it in her whole body. How does he do this to her?

He waited for her to calm down, then squeezed the fist of hair, pulled her head back, and dove in for a kiss, tongue first. Then he pulled back and spit on her face. Then slapped her with his cock hard enough that it stung.

“You’re the sexiest thing I have ever met. But, you came without permission."

Another part of their game. He controlled her orgasms; she could only cum with his permission. She knew this lapse meant a punishment.

"Now, make me cum!” he ordered as he shoved his cock back into her mouth.

She sucked him with all she had. She hoped he wouldn’t last long. Her right hand returned to her pussy – the degrading treatment made it so she would need to cum again soon.

He gasped, “I am close. Take it.”

She normally like to suck the cum out of the head of his cock as he came, but this evening he would have none of it. He shoved himself all the way to the back of her throat and came. It pained her as his cock contracted and expanded four times with each spurt going directly into her throat. Yes, her throat was going to be sore tomorrow.

He pulled out and they both stopped – he resting his hands on the windowsill and crouched over her; her still in “position one” but with her arms by her side, breathing hard. She needed to cum again, but his spit and cum covered cock, still erect, was staring her in the face.

She slowly rose up a bit and started to lick him clean. This was also part of their game: she had to clean his cock every time after he came. When he told her, Lily wasn’t sure how she felt about this rule, but she had grown to like it. She liked his cock, she liked that the taste was uniquely them, and she liked taking care of him. His cock stayed hard as she tongue-bathed him.

He eventually pulled her up. She was unsteady on her feet in the high heels and sat back against the windowsill, cool against her bare ass. He started fingering her. It felt good.

“Does pet need to cum again?” he asked devilishly. Lily just nodded. “Turn around,” he said as he spun her around by her shoulders. She leaned over the window and without warning he thrust his still-hard cock into her.

She could see people out on the street, did they know what was happening just a few stories above? In this position, they clearly stuck out into the corridor in clear view of anyone who might pass by, but she did not care any longer, the need to cum more urgent.

“Cum on my cock,” he instructed.

It did not take long – she had reached the point where she was on a hair trigger – a few rapid thrusts and she was moaning on trembling legs.

He zipped himself back up still semi-erect and helped her up, grabbing the clutch for her. Lily leaned against him, unable to stand on her own. Two doors down, he pulled out a card key – this whole time they had been less than twenty feet from their room where they could have had complete privacy! In the room he let her go in the bathroom first while he found them some much-needed water to drink.

Lily’s face was a mess. Makeup ruined. All she could do was wipe it off as best she could. When she came out of the bathroom, he was sitting in a winged back chair that was near a large desk, suit jacket off, sleeves rolled up. Held out a glass of water to her, but remained seated. The water was cool and soothing for her throat. She hadn’t realised how thirsty she was. He looked up at her admiring her form in the dress and heels as she awkwardly stood in front of him.

He needed to see her body, “Take the dress off, leave the heels on.”

She was tired and needed a break. The large and high king-sized bed looked so inviting, but he was not to be denied.

Unzipping the back of the dress and letting it fall to the floor, she stood before him naked but for the velvet straps around her ankles.

“Gawd, you’re beautiful,” he said with lust in his eyes. “You need to be punished for cumming without permission and I still need to claim one more hole tonight, pet,” he announced.

She shivered at the thought.

“Spread your legs a little more,” and she did.

He jumped up quickly, and grabbed the back of her head with one hand and kissed her hard. He massaged her pussy with the other hand. In spite of everything, Lily responded to his touch. She could feel another orgasm building. Just as she was about to go over the edge again, he suddenly stopped.

“Too soon, my pet,” he teased her. “Bend off the desk and don’t move,” he commanded.

Lily hadn't seen the cuffs that were attached to the legs of the desk when she came in. He obviously had prepared the room. Before she had time to digest all this new information, her legs were cuffed to the desk legs; spread wide and awkwardly balanced on her heels. It was uncomfortable; she had to hold on to the front of the desk to maintain the position. A position where she was very vulnerable, exposed, her "holes" available. She could feel moisture dripping from her pussy. She heard him walk away.

There she was, good girl Lily, wearing nothing but the sexiest heels she ever owned, a choker that signified her submission, bent over a desk displaying the jewel of the butt plug, waiting for him to come and take whatever he wanted. She tried to think who she knew that would believe this. There was no one.

He made her wait an interminably long time. She had been on the brink of orgasm and needed him to finish what he had begun. Lily could hear him moving around the room, it sounded like he was taking his clothes off but she dared not look. Then she heard the water running. Was he taking a shower? Does he not realise the state he left her in?

After too long, Lily could hear him walking around the room, but quietly, he was in bare feet. He came up behind her and set something down on the desk she couldn’t see. He started massaging her bum. Finally! He squeezed and caressed her, every now and then teasing her pussy. She needed him inside her! Suddenly, the sensation changed. It wasn’t his hand. Was that leather? His belt! He rubbed the belt along her pussy and she could feel her wetness drip onto it.

Suddenly, he smacked her ass with the belt. It stung but was not unpleasant. This was not the first time they had done this.

"I think 20 is a fair punishment. That was one. Count them off."

A few more smacks, alternating buttocks.

Lily called out the numbers, "Two! Three! Five!"

"Nice try!" He laughed as he rained a barrage of whips up and down her legs ending with a sharp smack directly on her pussy that made her jump and give a yelp.

Lily always tried to cheat when counting off her punishment. It had become part of their routine. She liked being the brat and she liked being put in her place.

"We're at four," he reminded as he started on her bum again.

She could feel her heat rising in her core and they continued.

“Spread your legs more,” he ordered.

She did and then felt the sting of the belt, from down to up, on her pussy again. It had the effect of driving her crazy. Then, just as suddenly, he stopped; twenty already.

He was fiddling with something.

“Put your hands behind your back,” was the next command.

She did and felt him looping her wrists one at a time through the belt. He pulled tight, and just like that her wrists were bound. How did he do that? Lily wondered.

The butt plug was rather unceremoniously and quickly pulled out of her. Weirdly, she had gotten used to it and now missed it that it was gone, feeling empty. Then, she felt his hand on her hip and his cock, hard again, rubbing along her pussy.

“Does pet need to cum?” he asked.

“Yes!” she cried out.

“OK. I am going to fuck you. Cum twice. No more, no less” and he lined up his cock with his fist and slid into her.

He fucked her with a steady rhythm, not with the violence like out in the corridor, but the effect was the same. Lily, the former good girl, now cums on command. Twice.

After her second orgasm, Lily’s legs gave out. She couldn’t steady herself since her hands were bound, but she was still impaled on his cock. Between dick and desk, she remained in place. He picked up the thing he had placed on the desk earlier and she felt the trickle of lube dribbling down her backside to her anus. He worked it around the opening before sliding first one, then two fingers into her rectum. This was still a relatively new sensation for her, but she liked it.

With his cock still inside her pussy, he could easily make her cum this way and she wished he would continue. That was not the plan for tonight, however. He finally removed his fingers and his cock from her pussy. She could tell he was lubing himself up. Then, the head of his cock was at the entrance to her ass. With one hand he got a firm grip on her bound wrists. With the other, he guided his penis into her. The pain was almost instantaneous as soon as the head spread her opening.

She cried out and he stopped, but only for a moment. He then continued inserting more of himself. She swore he was bigger than the last time. And harder. The pain was almost blinding. She wasn’t sure she was going to be able to do this.

Then, he pulled out a bit and there was some relief. Lily felt him adding more lube and then the pain again as he slid back in. Pain, yes, but less this time. He started a steady rhythm, in and out, but not going very deep. Every time it started to feel good, he would push a little deeper, always keeping her on the edge between pain and pleasure. Eventually, she felt his thighs against the back of her legs and pleasure starting winning. Soon, he was fucking her; she was being sodomised. It felt good. She could feel that new and different kind of orgasm building that she couldn’t quite explain – deeper, more full.

“I am going to cum,” Lily announced.

“Together, pet, you'll know when...” he responded picking up the pace, pulling her by the hips onto his cock.

After what seemed like ten minutes of strong thrusts, but was probably only seconds, he whispered in her ear, “Are you my whore, pet? My paid whore who lets me fuck her ass?”

At the second “whore,” she started convulsing with an orgasm she would never forget. He jerked a few times and she felt his cock expanding in her ass. Where those contractions hurt her throat earlier, now they only served to prolong her orgasm making her delirious. She felt him fall on her back, his weight trapping her arms and smashing her to the desk.

Lily had no idea how long they lay there like that breathing heavily. He was starting to feel heavy on her back and her arms ached from being trapped between them, but for some reason she didn’t move. Eventually, his cock softened and slipped from inside her. She could feel his cum start to leak out. He pushed himself up and freed her arms. She stood up and turned, and they kissed passionately.

When the kiss broke up, he said, “Let’s jump in the shower so you can clean me. Then let’s get some rest. We have all night.” He took her hand and led them to the bathroom.

Lily was already imagining waking him up in the middle of the night with a blowjob.

That is definitely not something a good girl would do.