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. Natalie Earns Her Money

Discussion in 'Cuckold Stories' started by EroticWriter, Feb 23, 2018.

. Natalie Earns Her Money 5 5 2votes
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  1. EroticWriter

    EroticWriter Well-Known Member Author!

    Natalie Earns Her Money

    by EroticWriter First publshed in 2010.

    Her eyes grew wide when his pants came down. This old man was already up and ready. Impressive, but she had seen men before, younger men, who were hard like that as soon as the pants came off. After all, Natalie was so lovely; almost all of them had that reaction upon seeing her nude. This man though, was bigger than just about all of them.

    The Madam opened the brothel door to see a frail, elderly gentleman. "Can I help you?" the madam asked.

    The old gentleman looked embarrassed as he removed his hat and said... "I hear that you have a gal working here named Natalie. I want to see Natalie."

    The madam hesitated. This old guy could never survive a round with Natalie. She began... "Sir, Natalie is one of our most expensive ladies, perhaps someone else..."

    No, I must see Natalie." Just then Natalie appeared, and his eyes widened at the sight of her.

    She was absolutely, positively the most beautiful woman he had ever seen.

    She was dressed in a tight fitting bright red dress that was low cut and revealed more then it covered. She was a full head taller than he was with a stunning full-breasted body and long black locks that reached almost to her beautifully rounded ass.

    "You're Natalie," he asked? She said that she was and announced to the old man that she charges $1,000 per visit.

    Without blinking, the man reached into his pocket and with his hand trembling handed her ten $100 bills that he peeled off a thick roll. Natalie and the madam exchanged glances. This old boy is loaded. He, we treat with respect. The Madam immediately reached out and Natalie turned the money over to her. The madam would take her 40% cut and place the the rest into her safe where it would be kept for Natalie.

    The two went up to a room and as he excitedly disrobed he asked Natalie how long of a session he would get for $1000. Natalie replied that normally it would be for an hour, but if they were in the middle of something when the hour was up, his time could be extended for a reasonable period 'until the deed is done'.

    As it would turn out, both would be surprised when they saw what awaited them. When Natalie removed her dress, his eyes bulged at the sight of her. His penis immediately began rising, the first time it had so readily done that in years. Dressed or naked, Natalie was lovely, absolutely stunning.

    Her upright breasts were the size of grapefruits, and were topped by pink nipples. Her waist was shaped like an hourglass, and her stomach was flat and hard. The trimmed pubic hair between her long and shapely legs was dark, just like her head.

    Her eyes grew wide when his pants came down. This old man was already up and ready. Impressive, but she had seen men before, younger men, who were hard like that as soon as the pants came off. After all, Natalie was so lovely; almost all of them had that reaction upon seeing her nude. This man though, was bigger than just about all of them.

    Because of his age, his penis pointed almost straight out to the front rather than up, but it appeared to be stiff enough to satisfy any woman. But, will it stay up like that or just go down and hang there like a lump? After all, he seemed so old. His balls even looked old, because they had loose skin all around and were hanging lower than younger men's ball do.

    "Mister, I can see that you're ready, so I guess we can be getting right to it. Which position would you like me in first?"

    "On your back first, Natalie, so I can do some kissing while I'm fucking. But first, I want you to put the red dress on again."

    "You want it on? It's an expensive dress and I don't want it stained."

    "Don't worry, I won't be staining it. You can just lift it up while I enjoy your lower half."

    She pulled the dress back over her head, and as it came down over her face, he reached out and had himself a good feel of her breasts. She paused, and when he seemed to have gotten his feel, she pulled the dress on down over her body and climbed onto the mattress.

    "Like this," Natalie asked as she tugged her dress up under her ass and leaving it up around her waist laid with her lovely legs opened wide for him?"

    "Yes. Exactly like that," he replied excitedly as trembling visibly, he climbed onto the mattress!

    When he climbed over her she reached out to "help" him. Holding his warm thick penis with her fingers and thumb, she told him to wait while she aims it for him. He did not seem impatient like the younger men so maybe she would be able to do one of her favorite things with men she likes.

    After asking if he was in a hurry and receiving a 'No', she used his penis to caress her vagina, running his head all over and getting it wet, then running it up and down over her clitoris. She had used her fingers, and men had used their fingers and tongues, and a couple of times women had used their fingers and tongues, but nothing seemed to match the feel of a nice penis, the head, being rubbed over her clit.

    Oh, she liked that so much and most men, if they were patient, enjoyed it as well. But all things must come to an end. When she sensed he might be getting anxious, she guided him within herself.

    The old man learned another reason why Natalie was so popular among the men who could afford her steep fees. Her youthful pussy, naturally tight, was trained by her to tighten even more around a penis no matter how slim. But there was no need for her to tighten herself for this man. Her natural snugness combined with his width, did all the work.

    Natalie sighed passionately as he spread her wide. She was acting as usual, but not acting as much as she usually had to. When he had worked it all the way in, oh so deep, she wrapped herself around him, arms, legs, even pulling his head down next to hers to let him know that all was well.

    Several minutes later she was smiling broadly as the man showed that he still had the old get up and go. It amazed her at one point. He seemed to have so much energy. Hell, when he took those long strokes, he even managed to get his dangly balls high enough that they would leave their position of resting on her ass and come up and then slam down against her ass.

    He had gotten that big penis of his up and had a go at Natalie in three different positions, reaching orgasm in two of them. Then he calmly left.

    Natalie was surprised. Before he had mounted her, he had said that he wanted her on her back first so they could do some kissing. But he had only kissed her once, as he was standing and getting ready to leave. It was like he wanted to kiss just her...rather than be kissing her while using her pussy.

    In a way, that made Natalie feel good about him, as his only kissing her after the fucking made her feel special, which she was.

    Before they had started, the old man had asked Natalie if they could pass on using a rubber. He had explained that since he had not been with a woman in several years, there was no way that he could have any disease.

    Natalie had hesitated, and then agreed. For some reason she believed him. He seemed so shy, so delicate, that he was probably telling the truth. It had been a while since a penis that was not capped had penetrated Natalie, and she had to admit to herself that it did indeed, feel better without the rubber. It wasn't often that she reached orgasm with a customer, and this one had brought her there twice.

    He wanted to walk down with her, so Natalie made him wait while she went into her bath.

    Having to sit on the commode afterwards and drain off juices was something Natalie rarely had to do, but it seemed worth it. After all, she had made an old man happy. Shit, the way he looked and sometimes trembled, he might not live that much longer. His heart must be strong though, considering how it managed to pump all that blood into his penis and keep it there.

    The next night he appeared again demanding to see Natalie. He had to wait almost 30 minutes as 'Natalie was currently engaged with a client.'

    There was a back stairwell to the upstairs corridor, and if a customer preferred, he could exit through the back rather than having to come back through the living room where other waiting customers might see them. So when Natalie, came down, she would come down alone, probably.

    She was alone. When Natalie, freshly showered, finally came downstairs she was surprised to see the old man waiting for her. She allowed him to give her a light kiss in greeting and then Natalie explained that no one had ever come back two consistent nights in a row and that there were no discounts...it was still $1,000 a visit.

    Again the old man took out the money and when he handed the ten $100 bills over to Natalie his hand no longer trembled. The madam took the money to hold for Natalie and the two went up to the room and this time he took Natalie in two different positions without cumming.

    Then he had Natalie give him her famous honey coated blowjob, during which she swallowed his entire stored up load, a trick she found easier to do if a man's load was honey flavored. Not soon after he was again on her and pumping away. Again Natalie allowed this man to do something she only did for special clients.

    Now he wanted to kiss while doing some fucking. When he placed his lips on hers, she responded, and with no acting because she sensed that he had strong feelings for her. Wanting another orgasm for herself, and liking this man, Natalie willingly extended his time.

    A little over an hour-and-a-half total, and another orgasm for both, he left, and just like the first night, he waited while she showered, then came down the stairs with her, as if to show the women below that he was still able to walk.

    As she escorted him to the door, one of the girls, one who was not as jealous of Natalie as some of the others yelled out..."Way to go Natalie!"

    The old man, grinning, turned to look, and Natalie, on impulse, raised his arm high in victory. Smiling broadly, he left.

    When he showed up the third consecutive night, several of the other girls came to see this customer they had been hearing about. They could not believe it, that he had returned a third night, but Natalie was not surprised. She had already had two sessions with this hot old man and he had told her that he might come back one more time.

    Because of ebbs in the stock market, business at the brothel had been a little slow lately so she was looking forward to another hour with him. The money of course was nice, but he was nice too and treated her just like a lady. Telling her this would be his last night with her because he had to return home, he again pulled out ten $100 bills.

    He seemed to prefer placing it into her hand so Natalie took it and immediately turned it over to the Madam. With a 'thank you' from the madam and a small cheer from the other girls watching, up to the room they went.

    This time he received her royal flush blowjob, followed by two sessions of bury the salami. During one of the fucks Natalie rode on top of him, and he let her go wild as she did her thing. She reached an orgasm of her own that was rather intense, to say the least.

    At the end of the hour Natalie was lying under the old man with her legs up around his waist. Her smooth golden tanned body was glistening with sweat and his large penis was still stiff and deep within her as he buried the salami for a third time. He was staying up on his knees at the moment while moving his ass slowly. He was thrusting deeply and enjoying the feel of her warm, snug pussy as he sucked on her lovely pink nipples.

    It didn't require much effort for him to reach her nipples with his lips while fucking since Natalie stood a full head taller, which placed his head in the vicinity of her luscious titties when they are fucking.

    Each stroke he took tugged tightly at her gorgeous inner lips. Natalie was famous not only for her knock out good looks, but also for how hot she performed in the bedroom, which of course was a demonstration of her acting ability.

    Men never knew that she was just performing and not actually enjoying them. Surprisingly, Natalie had climaxed more than once with this old man on each consecutive night, and had never had to act out her enjoyment of him.

    Natalie had serviced a few men, two or three, who were a little longer than him, but not by much. That increased length she preferred not to have to take. In thickness he was as big around as any she had ever had to deal with. Overall, when you combined his length with his width, he was probably the largest she had been with.

    Despite his size, Natalie had let him have her in the ass during his first bury the salami session tonight. This was something she only did for 'special' customers, customers with skinny dicks preferably. This old boy was the largest man she had ever allowed to enter her in that manner.

    Again, he wore no rubber, a risky venture for her, but she believed his story of only having been with her in recent years. They started out with her bending over on the bed, with him standing behind her. Using a little K-Y for lubrication, it was a struggle, but Natalie managed to take him while pretending to enjoy it.

    During the final minutes her feigned enjoyment became real, and as she reached under and rubbed her clitoris she said she wanted to lie down. They did, her inching forward carefully onto the mattress and guiding a pillow under her hips, and he managing to stay hard and buried.

    Now, with the two of them lying down, she turned her head so that if needed, they could be kissing, and he began once again.

    "You like this, don't you Natalie?"

    "Yes. Usually not, but with you, yes. Even though your penis is so large, I want this now."

    She sighed as his pumping started, and to show him she was sincere, she told him to take his time as she laid with her arms out to the front. Five minutes, more, and still more. Every once in a while, she would turn her head, and their tongues would touch.

    "Fuck me...ohh yesss."

    Then Natalie told him something that would boost his ego, big time, and she was being truthful. "I can tell that you're close, so I'm going to do something with you I've never done before with a man in the backside. I'm going to cum." She was on the edge, and all it would take would be to touch herself.

    As he throbbed into her ass, she reached under and brought her pussy to a raging orgasm that matched his in intensity.

    He saw a tear rolling down her left cheek when she said, "Kiss me."

    He did, and together, they tried to relax as their heightened heartbeats started to slow.

    She just laid there afterwards, barely able to breathe as the old man weakly climbed off of her and his softened penis slipped out of her asshole.

    The old man saw Natalie in a condition normally never viewed because with other customers Natalie would immediately turn over so the man whom had fucked her tight ass would not see it in a stretched and opened condition.

    Normally very small and pink in appearance, at the moment it was enlarged and because of her orgasm it was also a little red around the edges. In time, minutes, hours, her anus would return to normal, but for now, it looked well-fucked, or perhaps better described as fucked up as cum started to trickle out and down over her vagina.

    Usually very dignified in her manner and in control of the situation, for the first time Natalie seemed to be in a state of confusion. This had been her most intense ass fucking ever. Climaxing at the same time the man was cumming in her ass was a first for her.

    Usually she was the one receiving the compliments, but this time, she gave one.

    "Oooh that was good. That was my best fuck in the ass, ever."

    She just laid there, unable to move, with a pillow under her hips and her ass in the air. Her body shook as she laid flat upon her breasts and took deep breaths.

    If the old man is viewing me in this manner, so be it. Actually, he was. He was not only studying her upraised ass and opened anus with the dribbles starting to run down over her golden lips, but he was stroking his penis and wondering if perhaps, if he could get it up, he could return to that place he had just enjoyed so much.

    Her ass, standing and lying, was one of the finest he had ever seen or grabbed, and with it upraised like that, he had a view that was not to be believed.

    She panted, and he stroked and stared. Nothing was being said. The old man was enjoying the view and relishing in the fact that he had left this woman flat on her stomach and unable to move. He felt like one more orgasm should do it, but decided that it was going to be in her fine snatch, which he was now studying as his cum began running down between her lips.

    Finally, when Natalie rose to go to the bathroom, she provided him with a delightful view as she moved one leg to the side in order to crawl off the pillow and her snatch opened up a little. The old man was right there to catch her when she staggered and almost fell, and she thanked him.

    He replied with a smile; "No, I prefer to thank YOU!" She felt his penis touch her on the leg, and could not believe it when she looked down and saw that he was almost fully erect.

    For the first time, the normally dignified Natalie spent several minutes draining herself accompanied by embarrassing noises because this old man was the only one she had ever permitted to actually shoot into her anus. The few others had worn rubbers.

    Despite almost three years of working as a high class hooker, Natalie's face actually turned red with embarrassment when the old man entered the bathroom and bent over to kiss her as she was sitting on the commode.

    At the exact moment their lips touched, there was a huge "Pssssst" sound from below as more cum and air that the old man had pumped into her shot out of her ass. She giggled nervously and with a shaking voice tried to apologize:

    "I'm sorry..." she began.

    "No problem," he replied, laughing as he washed his penis over the edge of the sink. "That sound we hear is the sound of how happy you have made me." A few minutes later, Natalie joined him on the bed and appeared to have regained some of her dignity.

    Once again, Natalie was in control as she rolled onto her side and took his soft penis tenderly into her mouth. They had already passed the one hour point, but neither of them seemed concerned, most of all, Natalie.

    Down in the parlor, the girls who did not currently have a client were joking about Natalie and the old man with the huge cock that wouldn't go down. They were giggling and watching the stairs to see how much extended and free time Natalie would allow the old man this third night.

    The Madam was not concerned. The old boy had brought in some unexpected money over three normally slow nights and she was not about to go upstairs and call "Time!" Natalie was such a treasured girl for her, that she pretty much allowed Natalie to control the time she gave each customer. Besides, customers at one thousand a pop were not in great abundance during this depression.

    The hour was dragging out closer to two, and normally Natalie would have called an end to his time, but she was feeling lazy and enjoying his moves. She caressed his hair and back as he kept pumping away and was content to let this short old guy suckle on and rest his head between her lovely breasts.

    She had spent more time with this man, and he had been inside her longer than anyone else. All this combined with kissing and conversation, had made her feel very close to him.

    "Well old man, you sure surprised me. Not only can you get that barber's pole of yours up, you can keep it up about as well as any customer I've ever had. But actually in one way you've outdone them all. No one has ever used my services three nights in a row. Tell me, where are you from?"

    "Wait." He knew that his time was almost done. He got up onto his knees and started pumping harder, and Natalie giggled and sighed as his balls began slapping against her ass. As usual, Natalie felt his penis increase in size and as he neared another orgasm. Then he placed his lips on hers, kissed her, then groaned and filled her with juice one last time.

    Natalie moaned as she felt him throbbing and almost reached another orgasm of her own, but she was too tired. That prior ass fucking had really taken it out of her.

    She held onto his ass until his body had quit shaking and he had relaxed. Then, as the old man climbed off of her she again did something she usually never did for other customers. She used her mouth to "clean him up," draining what cum remained in his shaft down her throat.

    It was then that he replied to her question as to where he was from. "I'm from Philadelphia."

    "Really?" replied Natalie happily, as she stared at his dwindling cock, still looking so lovely. She leaned down and kissed it once last time. "I have family who lives there."

    "Yes, I know," said the old man as he climbed off the bed and prepared to dress. "Your father died, and I'm your sister's attorney. She asked me to give this $3,000 to you."

    (Some things in life are certain: death, taxes, and being screwed by an attorney.)
    Last edited: Jun 13, 2018
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