Thanks to Robyn for the suggestion on the topic of this story. She's a wonderful friend. And of course to my niece Jennifer for the motivation to write.
*
My niece Jennifer was only 19, cute as a button, but over the last three months she'd learn that asking her uncle for help out of a jam was just something family does. What she also learned, though, was that blackmailing that uncle was a bad idea.
Mr. Hoffman, my boss, told me such the day after we'd both taught my niece a lesson in my office. A nasty, naughty lesson. She thought she had a hold over me, but turns out that hold was short lived and would not be the rule going forward.
"She had you over the barrel there, boy, didn't she?" asked the gruff man.
Nodding, I thanked him for his help.
"No need to thank me, we each got a nice piece of your niece's ass. She's such a hottie and once she saw the cards on the table she knew she had to play along. So, where do we take this? She's a nice filly, I think she's a good girl, but I didn't want you doing something you shouldn't or being put in the position you were," said the man. "We can let this go, or...."
"Excuse me, sir, but let her go or what?"
My boss looked at me and smiled. "I did you a good one here, turning this mess around. It would be nice if you could agree to help me do the same."
Totally lost, I mentioned I had no idea what he was speaking about. Turn what around.
Mr. Hoffman was sitting in my padded chair in my office, contemplating things.
Finally he spoke. "You know, we all have problems. Your niece had a problem, you and Will solved it. Then you had a problem, and, well, I solved it. Now here's the thing, I have a problem and you can help me solve it."
For a second I thought I'd have to do something really, really wrong. But it was nothing like that.
"Have you ever met Oscar?" asked my boss. There was only one Oscar, the patriarch of our dealership. Actually, he owned 12 dealerships in the tri-state area. Mr. Hoffman worked for him, I worked for Mr. Hoffman.
Shaking my head yes, I mentioned that several times Oscar Brewerton had visited my office to speak about the dealership, but he hasn't been by in a couple years.
"He's been a little off, he's 75 you know, and while he's in pretty good shape he's getting up there. He's been a little cranky lately, bitching about overall results. I want to keep on his good side, because when he retires....."
Ah, Mr. H wants to take over the kingdom!
"He loves his boat and he loves pinching women's ass. It's amazing we haven't had a harassment suit, but he's so nice, so generous, well, he's everyone's kind and generous, means no harm, uncle."
We each contemplated things, quietly, before Mr. Hoffman spoke. "How much would it help my chances at the big job if Oscar was taken care of in a very special way?"
"Boss, I get your drift. An asset like Jennifer would really help your cause, wouldn't it,"
We decided to take advantage of the opportunity, with my 19-year-old niece Jennifer as the bait. We weren't sure how, we weren't sure it would work, but even if it didn't Jennifer would receive a bit more deserved humiliation and there was nothing wrong with that.
For her part, Jennifer was the perfect young lady when I'd visit my sister's house. Sis would complain that the girl was still a wild one, and only if she knew the truth. But that would send me spiraling into my own hell, so it was a perfect secret between the young girl and myself.
"I guess she's at the age of wildness," said my sister one night after Jennifer left on a date. "I know she's having sex, I found a condom in her room, so at least she's being careful. But I really do hate a couple of the boys she's dating. But you know I can't say anything, she'd date them more or more often."
"She's a good girl, sis, you raised her well. She will be fine."
If only the truth was told. Her cute daughter was a conniving, dick sucking, ass fucked, near whore of a girl. But hey, that's all right by me!
The following week Mr. Hoffman stopped by the dealership and gave the outline of a plausible story. Oscar loved his boat and he loved pinching a girls' ass. He loved being the boss. Why not set up a scenario where he got what he wanted in spades.
"I said I wanted to take you on a spin on his boat on the lake as a reward for great work," said Mr. Hoffman, smiling. "Show you some love. It helped when I mentioned your niece would be invited, and she's a looker. His eyes smiled at that. He asked if she'd be in a bikini and I said she was caught once sunbathing nude. That sealed the deal."
Saturday couldn't come fast enough. It was a perfect morning when Jennifer and I arrived. She had on a pink bikini, but it wasn't completely obvious as she wore a bright blue cover-up skirt and top that left little to the imagination. Cute as a button, I told her today would be worth triple points against her bill.
At first, she was taken aback but that deal. "I'm not going to be gang-banged" emphatically said the girl.
Reminding her of her situation, I told her she didn't have to do anything she didn't want to, but we did want to treat our boss like sultan, that we wanted him happy. She nodded, "I've got the picture. The old guy needs a blow job, he needs what all guys need, their cock sucked."
I couldn't help smiling. The girl knew what was going on. And she didn't back away or complain about it, a good sign.
Once on the boat we were immediately comfortable. Oscar was charming, and he told us to make ourselves home. He was drawn to my pretty niece, letting her steer the boat once away from dock. Of course his hand was on her back, steadying her, and he brushed her hair several times as well.
It was lust at first sight for the old man. Soon we were out in the middle of the lake, far from prying eyes, and Oscar said we'd be at the back of the boat and that we were to give Jennifer privacy to sunbathe while we were "playing cards" in the back.
Jennifer went to the front, and I stayed in the rear with Mr. Hoffman while Oscar went below. What we didn't know was there was a perfect view of the front of the boat where Jennifer was sunbathing in the nude. After a bit Oscar came back with a big smile on her face. "She's beautiful. Nice full tits and damn, she trims around her pussy. Last one of those I saw had a bushy look, but your niece has trimmed a lot of the hair down there. Damn."
The three of us laughed at his discovery. We spoke for a while before Oscar asked if Jennifer was a little wild. "I think she likes me. When she was driving her hand accidentally brushed my leg, and she didn't pull away right away. I think she realized where it was and pulled away, like it was a hot range, and apologized. I told her it was perfectly fine and she just smiled. She's a hotty."
I mentioned that her mother had said she was worried that Jennifer liked playing with fire, and that once she was caught making out with the father of one of her friends. I made stuff up, but it was as if she had a thing for older guys. Oscar just smiled a knowing smile.
"Maybe she just has a thing for mature men," said the much older man. "Guys who know what they are doing, not slam bam, thank you mam men."
We all talked about the difference between teenage guys, and older men. We all talked about how sex with our wives had become further and further apart as years went my. "Hell, my first wife, and my second too, couldn't stop sucking my cock before we got married. Then they forgot how after marriage."
"You know the old joke," added Mr. Hoffman. "Do you know the one malady that will stop a woman from sucking cock? No? It's a wedding ring."
We all laughed at that one just as Jennifer, clad only in her pretty pink bikini, walked to out lair. "What's so funny, guys? I heard those nasty words you were saying, you know, blow something? A job? Whatever," she was smiling as she shook her head at us.
"Guys, you all think about the same things don't you?" said my pretty niece Jennifer with a big smile. "I know at school if I mentioned "job" some nerd will say blow? It's as if your wives never give them."
Caught, we just smiled. Oscar broke the silence by saying; "You are never too old to have a pretty lady honor you in that way, never too old. And, well, lots of times wives have other things on their mind."
Jennifer sat and smiled, grabbing a soda from the case. I couldn't help thinking how hot she looked. Her bikini bottom was tight on her body, and had this little frilly trim that almost had the look of little girl panties. Her top showed off her pert tits, and each of us couldn't help but stare at her wonderful outfit. When she bent over for the soda three sets of eyes were focused on that pretty ass.
Oscar took control, the boss he is. "I think Jennifer and I should go below, and I can show her the facilities and where everything is down there. It's quite confusing and quite cramped."
The two, separated in age by nearly 60 years, went below. Soon we were hearing giggling and laughter as the two were hitting it off just fine. While early on there was a consensual line that might have been crossed, she willingly went with our boss to his lair. Mr. Hoffman broke the ice when he said that Jennifer appeared to know the "deal" and was willing to make it happen with "the old guy." At least to tease or tantalize the old man, maybe more. In any event we both moved over toward the closed door in an attempt to hear what was happening in the room below.
We heard laughter inside and Jennifer coyly saying that Oscar's hands wandered like a teenager. The two laughed at that one, as the man complimented her on her choice of bikini ("It's adorable, it covers you but shows a lot. It's very sexy"). For her part, Jennifer giggled at his banter.
At first our eavesdropping was uneventful, as the two spoke about things they liked to do, school, and sailing, but soon Oscar steered conversation to boys and sex.
Jennifer admitted she'd had sex, and laughed at nearly being caught giving a blow job in the janitor's closet at school and actually being caught in the back seat of the car in a state of undress. "We were in our undies, but I had my skirt still on so I moved it down to cover up down there but the cops saw his pants on the floor. They told my mom and I was grounded."
