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He seemed genuinely interested in her and her life. While he always treated her like a lady….she found herself listing all the things he had done to make her life better…He was paying her tuition for the graduate school courses she was taking evenings in business…Jennifer had a four year degree and a job as a dental hygienist …but regretted her career choice that required her to put her hands in people’s mouths everyday…She could talk to Bob about that and he had promised to help her find another job when she graduated…Of course, the allowance he paid her (which was now $1500 a month up from $1000) took a lot of the pressure off and allowed her to put a little money away for her daughter’s education. Bob had also provided her with a car…it’s in his name but she has the use of it…and he pays the insurance and has provided a credit card that covers her gas…

Jennifer and Bob went out 2-3 times a month…dinners at nice restaurants only at first…but they now mixed in some more casual evenings …Last month she just had him come over for a cookout. Jennifer found she actually enjoyed his company. He was 62 and almost 35 years her senior…but he was she had found a genuinely nice person…Of course, as he had pointed out more than once…she never would have given him a second look if they had met any other way. The sugar bowl made their relationship possible.

Jennifer checked her watch and noted he was ten minutes late. She smiled as she noted, that she had done much to make his life better too…mostly in the bedroom. Their first two meeting had been chaste evenings …dinner at two of the finer restaurants in town…Jen could see the lust in his eyes but soon realized he didn’t really know how to even broach the subject of sex…with a woman. He was a widower who lost his wife over a year ago…not really a player. After their second dinner and his awkwardness when he walked her to her car…she decided to take control. She called and invited him for coffee. While they shared coffee…she outlined the simple framework of an “arrangement”…She acknowledged his Friends first speech …and suggested it was time to get to the point…She outlined the things she needed a sugar daddy to take care of…a really modest list initially…and noted that there really was nothing she wouldn’t do in the bedroom for a man who provided those things…It was obvious he really didn’t know what to say…so she took him by the hand and walked him out to his car….and put him in his own back seat…pulled his pants down and blew him right there…She swallowed his load and smiled saying,..”You know what you need to do Bob if you want this to happen again.”

Bob had gotten the message…but he still didn’t really know how to handle her…He set up their next meeting at a local hotel…and conducted what felt like a closing presenting the cash and things she’s asked for…plus the car and credit card…on the desk in the room…then he looked at her longingly…Jen was still in her dental hygienist uniform…the timing had not allowed her to go home and change…She smiled at him and excused herself and went to the bathroom…She emerged wearing only the same heels she had worn all day and a necklace…

Bob had been seated in the one chair in the room…and Jen came over and sat in his lap….He had a look of childlike wonder on his face …as she leaned in and whispered in his ear…”Do with me as you will good sir”…and then he did. He lifted her up with a strength that surprised her and had kissed her deeply. She could smell his cologne and feel the urgency of his need. He stepped out of his clothes and exposed a serious erection…While his lust for her was obvious…she was impressed with his attentiveness to her needs …First fondling her breasts and nipples then slowly moving down to her pussy…He took his time and exhibited skills with his fingers and tongue that pleasantly surprised her… twice…She started a steady stream of slutty dialogue that she continued only after seeing the effect it had on him…She maneuvered around and took him in her mouth. While he writhed in pleasure…He pulled himself out of her mouth and stopped her saying only “please, I need to be inside you” She rolled over and spread her legs for him…and caught a glimpse of that little boy look again…In a flash it was gone and he was plunged deep inside her…They started in mish and then rolled over to doggy. Finally, he asked if she would take the top…and she did…all thye while telling him he wanted his cum…She found a rhythm and rocked her hips in such a way that she felt her orgasm building and when she came …she came hard and lost her breath…He came almost immediately thereafter…and she smiled when she realized he had waited for her…

She checked her watch again and he was now twenty minutes late and this wasn’t like him…particularly since this was the night she had agreed he could bring his handcuffs…

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Tales of a Hustler Caught in the Act PT 2

Tales of a Hustler---Caught in the Act—PT 2As we all just froze, and stared at Joey in the doorway, finally I managed to open my mouth. “Joey----how long you been there lil dawg”? Joey flashed a big grin and replied “just long enough to see homie there suckin up jizz off the floor and droppin it in dudes mouth. That's some sick shit yo”Sill nervous from our session being seen by someone u******e, I responded with “well, you should not have seen that.” Joey came back with another big grin, “Ya,...

Tales of a HustlerCaught in the Act PT 1

Tales of a Hustler---Caught in the Act—PT 1School zones were such a bitch. Ten miles an hour for what seems like an eternity. “Yo Matt—isn't that the dude from Jerry's that night we were all down there ? Hunter seemed excited with all the fresh young meat on display. “You mean the one getting his ass kicked”? “Ya, that's him”. “Yo jump out dawg, and grab him---and Hunter, don't hit none of those k I d s, they're minors”.Hunter jumped from the jeep and pulled off the bully from joey. A few bully...

Tales of a HustlerThick Black Cock

Tales of a Hustler---Thick Black CockThe orgy from the morning had been pretty epic—at least for my lil bro Dustin. I had never seen so much cum splashed on one dude. Literally from his head to his toes, lol. The twins had taken an instant liking to Dustin, which was awesome, cause like me he had a major fetish for twins. About half of us were finishing up some basic breakfast. Being Saturday, it was time to 'get to work'---enough had been wasted already on each other, and it was time ti hit...

Tales of a HustlerSat Mornin Gang Bang

Tales of a Hustler---Saturday Morning Gang BangAs I stood leaning into the door jamb, coffee in the right, cig in the left, Cole walked by and softly muttered “damm”. I turned my head and grinned “Aint that the most beautiful sight you ever seen”?Dustin had squirmed around so much in the bed that he had totally thrown the sheets off him—now flat on his belly, legs slightly spread, and that hairy ass on display for God and all the world. Two perfect mounds, rock hard muscle. No flab on this boi....

Tales of a HustlerBases Loaded

Tales of a Hustler---Bases LoadedIt had been one of the most intense games in recent history. The Cardinals were down by one, bottom of the ninth, and the picture—my lil bro, was up. A win would give the Cardinals a forth straight state championship. A loose—well you can only imagine. I had run up to the announcer box and borrowed the mic from Coach Wallace, as I as much as anybody was going nuts. The crowd was in a constant roar.“Aight ladies and gentlemen—here we are—the moment we all been...

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