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Claudia Darrin was a forty-seven year old Manhattan socialite with the body of a twenty five year old, who had married and divorced her way to financial independence. Personal trainers, a talented plastic surgeon, and determination were the reasons that she could still turn heads and cause the occasional accident. Claudia believed in living well and looking good; no vacation or resort was too expensive, no clothing was too extravagant, no skirt too tight and no heel too high. Claudia loved to tease and she loved to shock.
Anders Standt both dreaded and looked forward to his next client. Anders was a 26 year old personal trainer who worked for one of Manhattan’s most tony gyms. Claudia was, he thought, somewhere between thirty eight and forty two years old, with a taught body, a heart shaped ass and a huge rack. She was also a word class cock tease. Though the workouts that Anders put her through were strenuous and sweat inducing Claudia Darrin never showed up or worked out in anything approaching ratty gym clothes. She usually wore a tube top with shorts or occasionally a one piece leotard. Her makeup was always perfect and professionally applied, her talon like nails always matching the color of her lips. She also was the only woman the Anders had ever seen who arrived ready to work- out wearing five inch come-fuck-me pumps and large hoop earrings that just screamed; SLUT.
He once asked her why she even insisted wearing her pumps on the stairmaster and she replied; “Anders, I ALWAYS wear high heels, even in the shower.” (Even though this was an exaggeration Claudia had thereafter kept her shoes on when she showered in the gym. She knew that the female members and employees would talk and word would filter back to Anders. It amused her to no end to see Anders’ cock straining in his shorts during their workouts.)
She was also an incurable flirt. Claudia never missed an opportunity to brush up against her personal trainer. They talked frequently and Claudia let it slip that she liked younger men. Anders immediately perked up and said, “You know Claudia, I am twenty six.” Claudia just laughed and sat up. (She had been doing crunches while Anders held her stiletto clad feet.) She gently placed her hand on his cheek and told him that while he was very attractive he was simply too old for her tastes. She then went back to her crunches while Anders though but did not say; Bitch. They had been working out together for a couple of years now and while Claudia was careful to never reveal anything of herself she knew quite a bit about Anders. She was aware that he had a younger brother who often came by at the end of the day.
Driving her personal trainer crazy was one of Claudia’s many pleasant diversions.
She saw Anders’ brother as another way to torture him.
Claudia had “forgotten” her purse and had asked Anders, “Do you thing your brother could swing by my building on his way here and drop my purse?”
“No problem, I am sure I can catch him before he leaves school.”
About an hour later Anders’ brother arrived. “Excuse me Claudia, Troy just came through the front door with your purse.”
“Great, we could stand to take a break sweetie.” Anders walked over to the juice bar in the center of the gym where his brother was waiting and Claudia followed.
“Troy this is Ms. Darrin, Ms Darin, my brother Troy.”
“Call me Claudia. Why don’t you sit with us Troy. We were just taking a break. By the way, thank you very much for picking up my purse.”
“No problem.” Troy smiled back.
“Anders would you mind getting me an iced tea?” she asked.
As Anders turned around and headed back for their table he saw that Claudia was sitting very close to his little brother and was touching his arm and hand frequently as they talked. Troy had just turned eighteen and was relating the story of his missing his senior prom due to work.
“YOU missed your Prom. Work is important but when you are young you need to make sure and not miss those milestone events. Anders YOU went to your prom did you not?” she said.
“Yea, I went but Troy has a stronger work ethic than I did back then.” Anders replied absent mindedly as he focused on Claudia’s tits. Troy’s heart was racing. Claudia had been touching him the whole time and now the toe of one of her high heels was gently caressing his calf as they continued to talk.
“Troy, do you have any plans for this Friday?” Both Anders and Troy were surprised and Troy said that he was free. “I appreciate you helping me out with my purse, why don’t you let me make it up to you and at the same time correct the mistake of you missing your prom by taking you out Saturday?” Troy was stunned that this incredibly sexy babe, whom he had just met, had asked him out but he stammered a yes.
Troy still lived at home and did not want his parents to know who his date was so he had asked bakırköy üniversiteli escort Anders if he could meet Claudia at his place. Anders had said, “Sure, no problem.” but inside he was seething. What was up with this chick anyway?
About seven o’clock a limo pulled up to Anders’ building. Both Anders and Troy were standing on the curb waiting. The driver got out and opened the passenger door. Troy and Anders both took in a breath as Claudia emerged. She had on pair of skin tight leather pants, and a long sleeve black satin top that looked way too small. The top was over her pants and a wide belt held everything in place. While Claudia was normally about 5’6″ in her heels she was now almost 5’9″, almost as tall as Anders and taller than Troy. She was wearing her platform stripper heels because they made her feel more powerful and she always liked to feel powerful when she took some kids virginity. Anders stood with his stomach churning as they drove off.
The divider was up as the car left the curb. Claudia had already moved so close to Troy she was almost on top of him. They talked this way for almost fifteen minutes until there was finally a lull in the conversation. Their faces were already very close together as Claudia leaned forward and kissed him softly on the lips three times. On the fourth kiss she forced her tongue into Troy’s mouth and they began a deep French kiss. Troy was in fact no virgin but he had not been with a real live woman either and his heart was pounding. After about ten minutes they came up for air and Claudia re-applied her lip liner as Troy caught his breath.
She handed him a drink and took one herself. Just then they hit a pothole and she spilled her drink all over Troy’s crotch.
“Oh, god! I am so sorry.” She exclaimed as she began to wipe it up with a small towel.
Troy just closed his eyes and steeled himself to maintain control as Claudia felt his cock grow. She had intended to tease him quite a bit longer but decided to shift her game plan.
She said softly, “Do you want me to suck it?” He nodded. She smiled a wicked smile and slowly opened his pants.
She got on her knees in front of him and went down on him, taking his penis all the way down her throat. She deep throated him three times and then came up to him, kissed him deeply once and said. “I don’t know, do you really want me to suck your cock?”
“Uh huh.” He weakly responded.
Softly she said. “That’s not good enough little boy Troy, tell me what you want.”
“Please suck it.” He replied a little louder.
“Suck what exactly?”
“My cock.” He replied, slightly stronger.
“I am loosing patience Troy. Say it all and say it with conviction.”
“Suck my cock!” he said as loudly as his modesty would allow. She smiled and moved to go down on him but then stopped and said.
“Who is it you want to suck what?”
“Please suck my cock Ms. Darrins.” She raised her eyebrow at that and he tentatively said “Mistress?” With that she cupped his chin in her hand and said firmly.
“Troy, look at me. Ms. Darrins is hardly appropriate. I would have accepted ‘suck my cock Claudia’ but not now. You have two choices. Mistress is fine. It suits your current inflection but know this: I have two distinct types of sexual partners, slaves and lovers. If you want to be a slave then call me mistress but be aware. Though I will suck you off tonight that will be all that happens and in the future you will worship my body, polish my shoes with your tongue and drink my piss. If, however, you want to be a lover you will have to be more forceful than you have yet demonstrated a propensity to be. In that case you should address me as no more than ‘Bitch’ and you should be prepared to take what you want. If you do so you will have to sound like you actually mean it and you will have to be prepared to make me do what you want.”
She then whispered in his ear, “Mommy likes it rough. So what is it going to be little boy, are you going to be a piss drinking sissy or a hair-pulling, slap-that-bitch-on-the-ass, man?” As she said it she ground her spiked heel into the top of his foot.
With as much authority as he could muster Troy blurted out; “Suck my cock you fucking bitch!”
She smiled and softly replied, “Make me, sissy boy.” When he did not react she slapped him across his face hard and said “Looks like sissy boy wants to drink mommy’s piss.”
At that moment Troy realized he did not want to be a sub and he grabbed a fistful of her hair and pulled her into his crotch. He grabbed his cock with his free hand and, aiming it at her perfect mouth, he said as forcefully as he had ever said anything, “I said suck it you fucking whore!” With that she opened her mouth wide and again deep throated him.
Troy was in heaven as he watched this forty-something bakırköy bdsm escort blonde in tight leather pants and stripper heels blowing him in the back of a limo. The limo took them right to her building where Claudia spent the next six and a half hours teaching Troy everything he would ever need to know about servicing a woman.
About 2a.m. she dropped Troy off in front of Anders’ building. She walked him to the door and while Anders’ watched, from his second floor walk up, she and a boy young enough to be her son kissed deeply on the front porch. “I will never see you again Troy but thank you for a wonderful evening. I want you to always remember tonight so I think you should have a souvenir.” With that she took a step back and ripped her blouse open, took it off and handed it to Troy. She then turned on her heel and unhurriedly walked back to the limo, her ample tits standing tall and firm.
Claudia was charged up on her way home. She slipped on a leather jacket but did not bother to zip it up. There were two items of business yet ahead. The limo driver was a 22yr old who three years ago had chosen the path that Troy did not take. Claudia grew wet thinking of how she was going to humiliate this particular kid tonight. The second item was a nineteen year old who worked at the Pierre. She had been alternatively teasing and scaring this kid for a year. She knew he worked the graveyard shift on Saturdays and she felt like this was the night to make the kill. Claudia smiled that same smile as earlier as she picked up her cell phone to reserve a suite.
The limo pulled into the underground VIP hotel entrance about 3a.m. Claudia was delighted to see that her quarry was actually working this door tonight. The front desk had already alerted the young bellboy and he was ready with a key to escort Ms. Darrens to her room. “You just can’t plan things better than that.” She said to herself as the limo rolled to a stop. Now, for the first item on her agenda……
Josh came forward and opened the car door.
“Good evening Ms. Darrens.” He said politely yet confidently. Claudia stepped out of the car and smiled. At this moment her driver was pulling the suitcase Claudia had carefully prepared out of the trunk. The handle broke free of its mounts and the case fell loudly to the floor and sprung open spilling a few panties.
Claudia had carefully cultivated the rich bitch image with young Josh and she sprung into action.
“What the FUCK is your problem Steven! First you swerve all over the road all night making it almost impossible for me to get laid and now you through my clothes on the stinking garage floor!”
“I am so sorry Ms. Darrens…” With that Claudia delivered her second stinging forehand of the evening.
“MISS DARRENS?!” She said curtly.
“I mean I am sorry Mistress.” He said sheepishly while looking at the floor.
“That’s better.” She said quietly but firmly. “Now pick up my shit before my patience runs out.”
As Steven bent over and began to pick up her panties and other garments she placed her spike heel on his shoulder and shoved him back to the floor. “With your teeth, asshole!” She said in a frustrated tone.
Josh was both horrified and terribly aroused. Ms. Darrens, a known bitch mind you, was standing there on one foot with a heel cocked up, her hands on her hips and an open leather jacket, which barely concealed her tits while she made her young driver grovel in front of her. As Steven got to the last pair of panties Claudia placed her heel on the filmy material just as he was trying to lift it up.
“That one is in a greasy puddle you dipshit.” She said. As he released it from his mouth she kicked the offending pair of panties away and placed her shoe square in the puddle before stepping back and tilting her shoe up, keeping the heel on the ground.
“Now clean my shoe off and I mean the soles first as swipe.” She said. As Steven started to lick the sole of her shoe clean she looked down at her footboy and told him he better be through but fast as she had to piss badly. After about thirty seconds of shoe worship Claudia loudly sighed and said. “Fuck it.” She then began pissing. The piss ran down both of her tightly clad legs and out over her feet and shoes. Steven started to pull back but she told him to not stop licking until both of her shoes were completely piss free. After they were clean she turned and walked away. “Joshua, be a dear and pick up my case.” With that Josh hurriedly followed her onto the elevator and Steven was left to his own devices.
Claudia stood right next to Josh on the way up. She suddenly turned and whispered into Josh’s ear, “Humiliating a man always makes me wet, did it make you hard?” Josh stammered but eventually shook his head no even though his cock was ready to rip through his dorky looking uniform. bakırköy elit escort “Really” She again whispered. Again the shaking head. Suddenly she reached out and cupped his crotch. “Feels hard to me. Do you usually LIE to important hotel guests you little twerp.”
“I….I uh” his confidence was gone. Claudia now shoved her well manicured hand down his pants and roughly grabbed his cock.
“Take your pants off right now.” She whispered harshly. When he failed to do anything she spun around while still holding his member, bent her leg at the knee and stabbed the emergency stop button with her stiletto heel. “Take them off and do everything that I say or I start screaming rape.” She said this in a normal tone and volume. He slowly complied, taking off first his shoes, then his pants. “Underwear too, and be quick about it.” She said softly but firmly. She made him take everything off below the waist and she stuffed his clothes into her purse.
As the elevator doors opened on the penthouse level Claudia calmly reached down and holding his cock firmly guided a pants less Josh out of the elevator toward her room. She made him open the door for her and carry her luggage into the room. Everything was as it would normally be except for the fact that he had no pants on. While he had been putting her suitcase in the bedroom she placed a upholstered, armless chair in the center of the room where it could clearly be seen from the still open door to the suite. Josh re-entered the room and quietly asked if he could have his clothes back.
“Sit down.” Was the only response that he received. Josh then sheepishly sat down while looking out the open door. Claudia took off her jacket and carelessly tossed it on the floor before straddling young Josh. His cock was pinned under her snatch as she rode slowly back and forth pressing her tits to his face.
“Suck my tits Josh. I know you like girls. I can tell by the way your cock is rubbing against my pussy.” She had said this in a normal volume but because of the open door it almost seemed like shouting. Josh kept looking back and forth between her magnificent breasts and the door so Claudia made his mind for him.
She cupped her left breast in her left hand, and grabbing Josh by his hair she fed him her tit and simply said. “Suck.” In spite of his fear he began suckling at her giant tit.
Claudia began to moan and said, “That’s it suck mommy’s big tits little Joshua.” She had him alternate between tits for several minutes and then pulled his head away and asked, “Do you want to fuck mommy little boy?”
Josh replied, “God Ms. Darrins yes.”
“Call me MOMMY.” She said pulling his hair hard. “Tell mommy you want to fuck her.”
“Okay, Okay… Please fuck me mommy.” With that Claudia stood up, unzipped the crotch of her tight black pants and sank back down, riding him hard.
Claudia used and abused him all night long and made him sleep on the couch. She called downstairs and told the night manager she was using him on a special project and would need him all night long. She asked the manager to get Josh’s street clothes out of his locker and have them sent upstairs.
The next morning Josh was instructed to dress in his own clothes. Jeans, sneakers and a T shirt made him look even younger. Claudia had changed into slacks and a conservative top but kept the platform heels on. She was out for some shock value.
Josh was only about 5’4″ and Claudia towered over him in her heels. At about ten the next morning they rode the crowded elevator to the lobby. Claudia had a real fetish for mother/son role plays and had instructed Josh to address her as mother or mom for this morning’s performance.
They walked down to the next hotel and she asked the doorman there to hail two cabs. She wanted to be somewhere where Josh would not be recognized. When their turn finally came there were about fifteen people waiting behind them. Immediately next to them was an older couple. As the second cab pulled up behind the first Claudia opened her purse and took out five twenties and placed them in Josh’s hand.
“Now go straight to the library to work on your paper.” She admonished.
“Yes mother.” He dutifully replied as he leaned in to hug his “mother”. As he had been instructed he dropped his hand down to her ass as the hug ended.
She suddenly slapped him across the face and said “How many times have I told you not to touch your mother that way.”
They now had everyone’s attention, which is exactly what Claudia wanted. “Now give mom a kiss before she goes off to work.” She commanded. Now was the moment Claudia had been waiting for. In front of this sixty something couple and a slew on New Yorkers this attractive woman bent down to the young man who was almost a head shorter than his “mother” wrapped her arms around him and began a deep French kiss. The crowd gasped and Claudia had an orgasm. They broke the kiss and quickly disappeared into their respective cabs.
Claudia was exhilarated but also terrified. Next week her son was returning from boarding school. She had had minimal contact with him as he had grown up. Claudia was just never interested in any male who was not of the age of consent.
To be continued.
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