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 these things?
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 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 dining room is a Michelin starred restaurant where they were 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 little electric shocks 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.
