My Niece Jennifer Must Pay! Ch. 06

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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 canlı bahis şirketleri 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 canlı kaçak iddaa 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.”

Oscar asked how many guys she’d been with, and she calmly said she’d had sex with a handful of guys and had blown 10. I think he was aghast at that revelation, as he didn’t say anything for a minute. Then the quiet was broken by Jennifer cooing, “Oh, Oscar, that’s naughty.”

We wondered what was so naughty, but Jennifer quickly gave a description. I wondered if she knew we were listening.

“Oh, Oscar, your fingers are being naughty, playing with my breasts,” said the girl. “But it feels so good….and what’s this in your pants? I think you like me.”

“Oh girl, you have to suck it. Please. Get on your knees and take it out and suck my cock.”

Jennifer was to the point. “Oh can I? I’d love to suck your dick.”

Zippers were pulled and positions were shuffled, and Mr. Hoffman and I knew we had to get to a better viewing positions….the front of the boat where we could spy on the couple from the windows.

We slipped around to get a better view, and it was right in time. We spied Jennifer on her knees, in between Oscar’s knees, kissing all around his semi-erect cock. His head was back, enjoying the action, and Jennifer just kept kissing and nibbling his lengthening cock.

The man might be older, but with her coaxing his cock was soon hard and the girl began working her mouth all around his dick. She alternated licking with sucking….licking the base and around the middle, sucking the mushroom shaped tip. She didn’t rush, and he didn’t hurry her. It was quite an erotic site.

My niece bobbed her pretty head up and down the old man’s cock with a practiced flair, and I couldn’t help rubbing myself watching the action below. For his part, Oscar was rocking slightly and allowing the girl to have her way with his dick. He had a sly smile upon his face, and when he realized we were watching he made sure not to block our view.

We heard him direct the girl around his dick. “That’s it, lick my cock, lick it all over you cocksucker. Make it tingle. You are adorable.” The man obviously liked the blow job, especially when Jennifer’s intensity went from first to second gear. Soon she grasp his stem and jerked it while sucking the tip.

“Oh, that’s wonderful girl, don’t stop.”

Not that Jennifer had any intention of stopping, slowing or ending the action any time soon. She was clearly enjoying blowing the older man.

“So your wife doesn’t suck? She doesn’t lick your wonderful cock?” cooed the young girl, taking a break from the blowjob and talking to our big boss. “She should be ashamed, it’s a great cock and it deserves to be sucked.”

That brought a groan to the man, as he intently watched as the girl resumed her cock sucking actions.

Being a voyeur presented a great vision of my niece sucking cock. She obviously knew what she was doing, going fast then slow, licking and sucking. The man was obviously enjoying my niece, but didn’t look close to coming.

“You are so hot, girl, you are a beautiful sucking princess. Suck it girl,” exclaimed Oscar.

The two went at it for several minutes before Oscar dictated a second act.

“You are a bad girl,” said the man. “Bad girls should be spanked!”

Jennifer smiled as she pushed back from the man and rose off her knees. She admitted she’d been bad, and agreed that a spanking was appropriate. The girl should have been an actress as her words were entirely believable.

Draped over Oscar’s knees, the man slid down the bikini bottom, displaying the perfect teenage ass. Oscar rubbed the buttocks as he looked up at us watching intently from the window.

“So, you’ve been fucking your boyfriend? Sucking his cock too? And not just him? You are a Jezebel and need to be taught a lesson young lady,” exclaimed our boss. “I hate to do it, but you need a good spanking, and I am just the man to do it.”

With that Oscar sent his first crack of the hand down on my niece’s ass. That was followed by several more spanks as Jennifer cried out a few “ouch” and “I will be good” canlı kaçak bahis statements.

He issued several stern swats to her perfect ass. They weren’t too hard, but they did cause her to grimace and wiggle. That just made the man spank her more. It was awesome watching the action, and soon it was made even hotter when the man motioned with his head for us to join him below.

We weren’t stupid, if the man wanted help we’d give him help.

Entering the quarters we watched as Oscar spanked the girl. “She’s been a bad girl. She’s sucked a lot of dick for a 19-year-old, and now she’s making too much noise when I am spanking her. Could one of you shut her up?”

Mr. Hoffman had no hesitation in moving in front of my niece and slipping his cock out of his pants and into her mouth. Jennifer started sucking the man’s cock while Oscar spanked her ass. After a few minutes Mr. Hoffman directed me to take his place, and I replaced him in front of the girl.

Damn, my niece can suck a cock. I think she actually liked the spanking, as she ignored the pain and sucked my cock. I watched her work my cock, and it was a beautiful sight. Mr. Hoffman walked out while she was sucking me and came back with a ledge of butter…where he found it, who knows.

Mr. Hoffman rubbed the butter slap up and down her ass cheeks while Oscar continue to spank the girl. Soon he was rubbing the butter on his cock, and slipped that up and down her cheek.

“Oh no, not in my ass,” cried the girl, but without a lot of real emotion.

My boss rubbed the ass and then popped his dick into her ass, a little at first for her to get used to it, and then pushing to the max. I thought Oscar’s eyes were going to pop out of his face watching the ass action.

Oscar alternated his head back and forth, watching the ass fucking and then the blowjob. “Damn, this girl is taking it in both ends,” said the man, slowing his swats of her ass to watch the action.

Jennifer’s mouth action wasn’t as good as normal, but who could expect it to be as her ass was being ravished by my boss. He was pounding into it, groaning and moaning while telling her it was so very tight. Soon he couldn’t hold out, and he orgasmed in her pretty young behind.

“Oh my goodness, that ass is tight and hot,” said Mr. Hoffman. “You have to get some of this.”

I pulled my cock out of her mouth as Mr. Hoffman demounted her from behind. Oscar directed her around to his cock, and soon he was rubbing up and down her cum filled ass with her in the reverse cowgirl position. He centered his dick against her anus, pushing gently at first before pushing in full bore.

That last push moved his dick into her ass, and brought out a cry of pain from the girl. “Ouch! That hurts. Your big cock is splitting me open. Oh my.”

Mr. Hoffman and I watched as Oscar moved the girl’s ass up and down his dick. He did the guiding, but she was clearly fucking him. The old man was groaning as the girl fucked him, and it wasn’t long before he started bucking up into her ass.

“Oh, I am going to cum in your ass, I’m in your ass and I’m going to cum!” Not poetic, but it was the truth. Oscar shot his load, her second of the day, into her ass.

I swear the girl smiled, a conquer of two men in a span of a few minutes. But she wasn’t done by a long shot.

“Are you going to fuck her ass,” asked Oscar.

“What do you think, sir,” was my hearty reply. “You bet.”

Maneuvering the girl back across the man’s thighs, I moved behind her and began rubbing my dick up and down her ass crack. It was sticky with cum, and made my dick wet. Pushing inside her ass wasn’t too difficult, and soon I was thrusting in and out of her tight little ass.

Fucking the girl harder and harder, I reached around and grabbed her tits. Manhandling them, I couldn’t help myself. I needed to cum, and it didn’t take long for me to add a third load of man sauce to her tight little ass.

For the next few minutes the four of us sort of laid next to each other, exhausted. It was quite the experience, a gang-bang of my niece’s ass.

Jennifer broke the silence. “Guys that was awesome, my ass is killing me. I won’t be able to sit for a week. Damn you did me good,” said the girl. “That was so incredibly hot. I’ll never forget it. But I do need to get back to shore. Billy’s taking me to the movies tonight and I have to get cleaned up.”

Oscar smiled. “So, you are going out tonight. Are you going to fuck him?”

Jennifer said she didn’t think so, but maybe she’d give him a blowjob in a lover’s lane after the movie. “I mean, I’m thinking of you guys and I think I need a little more cock satisfaction.”

Oscar move topside to haul anchor and start back to land, but he told Mr. Hoffman and I to get her mouth ready for her date tonight. We knew exactly what he meant, as we fed her cock while she knelt beneath us and alternated between us.

What a day. What an experience. When she left the boat, she had two loads in her tummy and three in her ass. Not a bad afternoon of debauchery with my sexy niece.


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