The Entertainer

Posted in: Encounters

Jack was desperate! He was down to his last c-note, and with no real job prospects, he was starting to get the feeling that he wasn’t long for his apartment and would soon be out on the street. Every day he walked to the library and poured over the classified ads looking for a job but it was becoming increasingly apparent that he probably would have to take a menial service job at a fast food restaurant. “Christ,” he thought to himself, “here he was a recent college graduate, and unable to find a job in his chosen field!” As he continued to scan the want ads, his eye suddenly caught and intriguing looking ad in the “entertainment wanted”, listings. It read, “Needed: Well Built Young Men To Perform For Female Stag Parties! High pay, steady work! Call Jill at 555-1313 from 8 to 4.” The key phrase was “high pay”, and Jack could certainly use a little bit of that! He scribbled the number on a piece of scratch paper and went off to find a pay phone! The number rang at least five times until it was answered by a female with a deep husky sexy voice. Jack got right down to it, and made an appointment for later that afternoon at Jill Hadley’s office in the Murchison Building down town.

The outer office was barren except for a a few straight back chairs and two year old sports and news magazines to pass the time. There was a sign on the desk that said “Ring Bell For Service”, so Jack poked it a couple of times, and a few minutes later a lady of about forty five or so came through the door to the rear of and extended her hand and said, “You must be Jack, I’m Jill, come on and follow me back to my office!” As spartan as the outer office had been, Jill Hadley’s private office was just the opposite, with a plush carpet, beautiful furniture, a cushy sofa along the wall, and expensive looking paintings hanging tastefully on two of the four walls. Motioning with her hand she said, “Please sit down and I’ll tell you all about it.” Jack settle down in a deep comfortable chair across from Jill’s desk and waited for her to begin. After taking a sip of coffee, she began, “As I’m sure you gathered from the ad, Jack, my company arranges entertainment for female clients in the, how shall I say this, well, the more mature vein, I’m happy to see that you look to be in tip top physical condition, because our young men are required to remove their clothing and put on a show for the women at their gatherings!” “Are you still interested,” she asked? Jack knew from the way the ad was worded that it probably involved something like this, so he shook his head yes and asked Jill Hadley to continue. “Well,” she intoned, “we get calls for batchelorette parties, business meetings, birthday parties, and a dozen other occasions that an exotic dancer might entertain at, we charge a set fee of anywhere from $500 on up, depending on how may dancers we send out, and out of that, you get $200 guaranteed!” “In most cases, you can pick up as much as $200 dollars in tips from the women at the parties so on an average night you can usually pick up anywhere from $200 to $500, not bad for three hours work!” “If you decide to take one of the ladies home, you’re on your own, we discourage it, but we don’t have a rule against it, that is entirely up to you!” “Finally, you can usually expect to work two to three gigs a week,” she summarized, “so you have a chance to make some really good money!” “Still interested,” she asked!?! “When do I start,” he replied quickly!?! “Good,” she answered enthusiastically, “let’s get down to business!!!”

Jill shoved a pile of forms for him to fill out, and he spent the next half hour completing them. When he was done, she glanced at them quickly and then said, “Okay, Jack, they look all right, good, now then, I have to check on one more thing, you’ll have to show me your body, I have to be sure that you measure up physically!” “Right here,” asked Jack rather meekly??? “It’s as good a place as any,” Jill shot back, “you might as well get used to it, because from now on you’re going to be stripping in front of a lot more than one woman!!!” Jack nodded in agreement and stood up and removed all of his clothing, exposing himself completely to the older woman. With a practiced eye, Jill walked around him, checking out every square inch of him, making sure that everything was just right! Jill Hadley was not an unattractive lady, and much to Jack’s discomfort, his penis began to stiffen uncontrollably under her steady gaze! “I’m sorry, ma’am,” he stammered, “but I can’t help it!!!” Jill just chuckled and reached out and took his member in her soft hand and began gently jerking him, causing his legs grow weak and rubbery! “You have to get used to this,” Jill said softly, “in the next few days a lot of women are going to be touching your pecker, and on more than one occasion you’ll more than likely shoot a load of cum!” Jack nodded dumbly, the sweat now breaking out on his forehead while Jill leaned over and whispered softly in his ear, “Do you want me to suck you off, I think you need it!?!” Through dry lips Jack replied unevenly, “Oh please, yes, suck me off!!!” Jill sat down on the edge of the couch and pulled the erect cock to her warm mouth and let it slip in, caressing the large head with her smooth tongue. Jack groaned as Jill expertly used her tongue and lips on his now straining member, until almost without warning, his nut bag tightened up, sending a hot torrent of sperm into the mouth of the hungry cocksucker!” She drank down every last drop, not letting even a drop slip away from greedy mouth!!!

Jill quickly stood up, and immediately removed her own clothing, exposing a body while not thin and supple, was ample and full, a woman’s body that begged to be used by a strong man! Large breasts jiggled as she moved, her already erect nipples begging to be sucked by a hungry mouth! A slight paunch on her belly did nothing to take away from her over powering feminine allure, and her wide full ass and unbelievably hairy cunt only turned Jack on even more! Jill arched her back, jutting her chest towards him as an open invitation to partake of her cherry sized nipples! Jack practically dove at them, sending them both tumbling back on the couch in a mixture of flying legs, arms, and huge breasts! Jill was now panting hard and her cunt was leaking like an old worn out faucet, she was definitely turned on to the max and was in dire need of a good hard fucking!!! She spread her legs wide apart and begged, “Do me, Jack, one way or the other, mouth or cock, but just do me!!!” Jack’s pecker was now hard as a piece of blue steel, but he put off the fuck and dropped his mouth onto her furry mound and let his tongue probe her wet crack. “Oh god,” she moaned loudly, “eat it for me, do mama’s clit for her!!!” Jack didn’t need to be asked again, and his tongue motored over Jill’s hard nub until she was convulsing in a huge orgasm, and flooding his mouth with a gallon of cunt juice!!! Before she had a chance to catch her breath, Jack got to his knees and lined up his swollen rod with her gaping hair pie, and in one hard thrust buried it deep inside her warm wet fuck hole! This time, she screamed out, unable to control herself under the vicious onslaught that Jack’s pecker was inflicting on her helpless cunt! Jill threw her legs around Jack’s back, locking him into place, and then begging him like a whore to fuck her harder! Jack was close to going over the edge, but he smiled to himself thinking that Jill was just like any other woman, confident and sure of herself until she was getting fucked, then she was just like any other little bitch to come down the pike, a beggar in need of sexual relief who would say or do anything to achieve it! Just before he blew his nut, Jack looked at Jill’s face and could see that she a slave to her sexual desire! For the second time in fifteen minutes, Jack was emptying his cum inside of his future employer, and loving every second of it!!!

Afterwards, Jill lit up a Lucky’s, stroked Jack’s flat belly, and commented, “The ladies are gonna love you, Jack, I just hope you save some of this for me!” With those words she dropped her cigarette and took Jack’s cock into her warm mouth! He leaned back and thought, “This is gonna be one great job!!!”

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  1. Anonymous

    left me wet!!!

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