Pussy Playmate
by Master Jonathan
Copyright© 2022 by Master Jonathan
BDSM Sex Story: Vivian was a "working girl" - a prostitute. But business was slow one rainy day and she was afraid she'd wasted the night until a nice looking car pulled up beside her. The woman inside the car was looking for a party girl and Vivian took the job...
Caution: This BDSM Sex Story contains strong sexual content, including Mult Consensual BiSexual Heterosexual Fiction Workplace Sharing Wife Watching BDSM MaleDom Light Bond Polygamy/Polyamory Anal Sex Double Penetration Masturbation Oral Sex Sex Toys Prostitution .
It was a cold and rainy night in April and she was tucked as far back into the deep doorway of the older, brick office building as she could get, trying to get out of the wind and rain. It was Friday night and the building was closed for the weekend. Despite people’s desire to enjoy themselves on Friday night and forget the toils of the week, it was a bad night to look for customers.
In reality, business hadn’t been “good” in some time. Between the wet, miserable 35 degree weather, and the fact that the economy in Cleveland was about as bad as anyone had ever seen it, there wasn’t a lot of opportunities for a “working girl” these days.
Unfortunately, Vivian Ryder wasn’t running over with options. She had lost her waitress job about four years ago when the small family restaurant she worked at folded. It wasn’t much of a job even then, but it did pay the rent and put food on the table. However now, at 35 years old, she wasn’t really in demand and had to compete with younger, more energetic girls.
Vivian was still an attractive woman, she took care of herself and she still could turn a man’s head when she got dolled up. But time and gravity are no friend of a woman, especially a woman who made a living from her looks and body. Yes, there were younger women in the workplace, women with firmer tits and smoother skin.
However, Vivian didn’t fit most people’s picture of the average street hooker. At five-foot seven with shoulder length reddish-brown hair, hazel eyes, and a fit 38DD-20-34 figure, she was in very good shape for a woman her age in her line of work.
She didn’t have a drug habit, she had never done drugs, except for a couple times trying weed just to see what all the fuss was about. She considered drugs to be a fool’s game. She wasn’t turning tricks to support her kids because she didn’t have any. Neither did she have some deadbeat man she had to work to support, or an abusive and demanding pimp to send her out to earn cash for.
Why did she do it then? Why did she degrade and humiliate herself by becoming a common street whore? Well, the answer wasn’t all that complicated. Vivian loved sex and what’s more, she liked it hard and dirty and rough.
She wasn’t a masochist, but she wasn’t a china doll either. She liked hard, sweaty, screaming and moaning sex – if you weren’t totally exhausted when you finished, you weren’t finished! And she made pretty good money doing what she did for her customers.
Vivian kind of fell into the whole prostitute thing a few years back when she one of her customers asked her out on a date. She didn’t ordinarily date her customers but he was a regular, stopping by the restaurant whenever he would come through town. She had waited on him many times, and they had built a friendly rapport with each other.
They chatted a bit as she worked and she made sure to give him plenty of attention while he ate, never letting his coffee get empty or wait too long for his meal. One day though, he made a request that she wasn’t expecting. He asked her if she would like to go to dinner with him after she got off work.
She accepted his dinner invitation and met him back at the restaurant later that evening. They went out to dinner and had a really nice time. So nice, in fact that she found herself at his hotel room the next morning.
He had already left because he had to get on the road but he left her a nice note saying how nice the evening had been and that he hoped they could get together again when he came back through town. Inside the folded note was a hundred dollars. Whether he thought she was a professional or not, she didn’t know. But she took the money – it would help with the rent.
A couple months later, when the restaurant closed its doors and she found herself without a job, she remembered her date with the truck driver. She saw how few options she had and came to terms with this as a way to make a living. At first she was horrified that she had been reduced to such a disgraceful lot as being a whore.
But her horror soon turned to enjoyment when she realized she could have all the sex she wanted with no strings attached and make damn good money at it, money she had only dreamed of when she was slinging food at the restaurant.
Now she could buy nicer clothes, she didn’t have to eat at the same little restaurants like the one she had worked in, and she could afford some of the things she had wanted for so long. Was it a risky job? Sure it could be if you weren’t careful.
But she was careful – she insisted that all her johns used condoms which she kept an ample supply of and she was also a very good judge of people. She could tell whether the guy propositioning her was someone she could go with or not. She turned down a lot of shady looking guys because she didn’t like the way they came off.
Vivian could handle most trouble without too much effort. It only got serious once with a john that was high on coke. One of her cardinal rules was not to mess with anyone who was drunk or high – they are too unstable and too unpredictable. She kicked him in the balls when he refused to take no for an answer.
Word got out after that incident, that it was not a good idea to fuck with a working girl. They have the right to refuse a prospective john’s advances. If you treat them right, you get a good time; but if you don’t, you get hurt.
It was really quiet that night – quieter even than usual and she began wondering if it was even worth being out that night. The streets were practically barren and she had only seen one other girl working that night and that was a couple blocks away. She was a skinny 18 year old cokehead who turned tricks to support her habit.
Drugs had not been kind to the young girl ... she was so skinny from the drugs and not eating right that she looked almost anorexic. her eyes were hollow and she went through her work in a zombie-like state of mind. Vivian seriously doubted if the girl would live to see 20 the way she was going, and it bothered her a little.
The rumor amongst the other girls is that this youngster would take a cock in any hole and if you threw a few extra bucks in the deal, she would do it with you without a condom. A lot of the john’s didn’t like wearing condoms because they liked seeing their cum shoot out onto their whore’s tits and face.
They liked to see them swallow, and they liked to see it dribbling out of their pussies and asses. These things don’t happen when you use a condom, so even though it was more dangerous, they paid extra to girls willing to run the risk.
Vivian wasn’t one of those girls, though. Even if it meant losing a trick, she wouldn’t do it without a condom. And it seemed to be working because for the ten plus years that she had been working the streets, she hadn’t picked up anything nasty. She planned on keeping it that way.
She had been out in the nasty weather for about four hours and it was around 1:00 am when she finally spotted a car in the distance cruising slowly along St. Claire Avenue towards her. She didn’t want to get her hopes up, but it was moving slower than traffic normally did on the busy street.
As it got closer, she hoped it was someone looking for some fun. She stepped out of her doorway refuge far enough to be seen and still have the protection of the doorway overhang to keep her from getting wet. The car pulled up about three car length’s away from where she stood.
This looks promising, she thought looking at the metallic silver Buick La Crosse. Obviously the owner of this ride wasn’t hurting for money too badly! The headlights flashed off and on in an accepted signal for her to come over, so she tied the belt of her old raincoat tightly around her waist and walked sexily down the sidewalk, her long legs scissoring within her short, tight, leather skirt.
As she reached the car, the passenger side front window rolled smoothly and silently down. She leaned inside. It was a woman driver. Shit! she thought to herself. She had probably got turned around and couldn’t find her way back to her hotel. It was far too late for a woman to be out on these streets ... unless like Vivian, you knew how to handle yourself. And this woman looked much too refined and elegant to be a street fighter! She spoke in a husky, cultured, voice.
“Are you available my dear?”
Her question surprised Vivian, after all there aren’t many ladies out cruising for prostitutes and fewer still that are as classy as she looked. She nodded and the woman unlocked the door so Vivian could get inside out of the rain. She slid inside onto the expensive leather seat, apologizing to the woman for getting her car seat all wet. The woman smiled and waved it off casually.
“Don’t worry dear, it’s a lease!” she said. She was wearing a butter soft exotic leather full length coat that Vivian wouldn’t know where to begin to look for, not that she possibly could afford it anyway. The coat was open in the front revealing a white silk and lace corset, with ruffled edges around the top and bottom, a lace up back, and a neckline that pushed up and revealed a very large bust.
She also wore sheer white thigh-top stockings held up by the corsets garter straps. Her small, neatly pedicured feet were shod in strappy high heel CFM shoes that matched the rest of her lingerie. Her long blonde hair is put into a perfect ponytail with a large red ribbon securing it.
“I’m Vivian and I don’t do S&M, but anything else is fine with me,” she said, once she was settled in the car seat.
She turned towards Vivian as she gazed into her big blue eyes, high cheek-boned features, and perfectly painted lips. The woman smiled and Vivian could see a set of perfect white teeth.
“I’m Kathleen. I hope you’re free for the night Vivian, because we are looking for a full night of fun,” she said. “We don’t want a quickie as you girls put it.”
The term we caught Vivian a bit off guard. “We?” she asked.
“Yes,” Kathleen explained, “You see, you will not only be playing with me but also with my husband. We have come to your city for a conference and we wanted to have some fun while we are here. I hope you are okay with ‘doing’ a couple.”
Vivian didn’t give a damn one way or the other. An all-nighter’s was fine by her and so was the three-way. She told her prospective employer what it would cost and Kathleen waved her elegantly manicured hand airily as if the money had no meaning.
Vivian clipped the seatbelt across her old raincoat as Kathleen eased the car into gear and started down the deserted Cleveland street. As she drove, Kathleen explained a bit more what Vivian was hired for.
“My husband is also my Master – we are a BDSM couple and I am his slave. He sent me out tonight to find a second slave slut to play with. We aren’t into S&M either, although I don’t mind a spanking or some other forms of slight pain like nipple clamps and such things. To be perfectly honest, I have very big tits and super sensitive nipples – I love it when my Master uses my tits!” she said, her voice wavering as the thought of it began to sink in.
“I have done a few bondage scenes before,” Vivian replied, “But I haven’t done the nipple clamps other than a pair of regular clothespins which weren’t very tight and didn’t do much for me.”
“Well, you are in for a treat, then my dear. Master is wonderfully creative and He never fails to bring me to an excruciatingly powerful orgasm. But He always makes me wait until I am half-crazed with lust before He allows me to cum and His rule is that I have to beg and plead and ask permission before I am allowed to cum. My orgasms are His gift to me and I have to show I earned them and am grateful for them – which I always am.”
As she spoke, Kathleen dropped her free hand onto Vivian’s left knee and slid it slowly up under her skirt. Vivian spread her thighs as wide as the tight skirt would permit to allow the woman’s fingers to find their target and rub against the taut, silky crotch of her panties. She laid her head back and reclined her seat a bit so Kathleen could access her better.
She bit her lip to prevent the sigh of pleasure from escaping as Kathleen’s talented finger began warming her up for the coming playtime. This should be fun Vivian thought to herself. She had done a few three-ways and it was always fun to be the center of two people’s attention – especially when one was a woman! Playing with another woman in bed with her was Vivian’s idea of pleasure and she’s getting paid well for it.
“Where are we headed Kathleen?”
“We are staying at a little hotel a few miles out that I have an arrangement with. We’ll be there in no time. Oh and by the way, my slave name is diamond. But Master calls me slut and whore and cunt too. You can call me diamond. Master will probably call you slut, whore, and cunt too, but he may give you a slave name as well.”
This was just fine with Vivian ... she loved to be talked dirty to and called names like that. It turned her on to be called a slut or whore or cunt. She loved it when her lovers told her she was filthy or that they were going to do this or that to her. Dirty talk always made it seem hotter and naughtier!
Vivian was sorry when they pulled into the parking lot of the small, but plush looking hotel because Kathleen knew what she was doing with her fingers. Vivian and her panties were soaked and she smelled of sex, Kathleen’s toying had definitely lit her fires and now she was to meet the Master! Kathleen turned off the ignition and stepped out of the car.
“Wait a moment please Vivian, I won’t be long,” Kathleen said, turning off the ignition and stepping out of the car.
Vivian watched her employers elegant legs as they strode across the parking lot and disappeared inside the hotel entrance. After a little bit Kathleen stepped back out and waved for Vivian to come on over. As she stepped out of the car and closed the door, Kathleen locked the doors with her remote key fob. Vivian crossed the parking lot and went into the hotel with Kathleen. Inside the hotel lobby it was thickly carpeted and handsomely decorated. This was definitely one of the better class of hotels!
Taking her hand Kathleen walked Vivian towards the elevator. They stepped into the open elevator once it reached the lobby and the elevator operator welcomed them in.
“Three, please,” Kathleen said to the operator. They rode to the third floor quietly smiling at each other and holding hands. Heaven knows what the poor elevator operator thought of the two beautiful women! Once they got out of the elevator they made their way down the hallway.
“Oops! I almost forgot one thing!” Kathleen said, stopping in her tracks. She looked up the hallway then back down and then she pulled Vivian back down the hallway to a restroom next to the elevator.
“I almost messed up – we just about went into the room wearing panties!” she said, quickly hiking up her skirt and pulling down her silky panties. “Master has a rule about his slaves not wearing panties! I almost got us both in trouble! He would have been lenient on you because you didn’t know, but I would have caught hell!”
Vivian stepped out of her soaked panties as well, putting them in her coat pocket. As Vivian tucked the soiled garment away in her pocket, Kathleen reached up and pulled Vivian’s head to her so she could kiss her new playmate hard on the mouth, her tongue forcing its way inside her mouth and one delicate hand cupping her tit under the coat. Vivian could feel her nipples harden as they kissed.
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