[M4F] Blackmailing my Older Sister in Law During Family Vacation

NSFW

As I pull up the long driveway at 3 Schooner Drive, we have finally made it. I look over at my wife as she is sipping her ice coffee and say, “only four hours this time, not too bad if I say so myself.” I put the car in park, get out and stretch my legs. I watch Stacy walk towards the three bedroom house as she goes in and opens the place up.

It’s a smaller than average house but perfect for us, my in laws and my sister in law Monica. We each had our own bedroom, but the one tricky part is there was only one bathroom and one outside shower. The family has stayed at this place for more than 40 years and we will be joined by other family members who stay in different houses in town near the lake.

After 30 minutes pass, I hear the sound of a car approaching, as I see my father in law Steve pull up. I walk over and greet everyone, especially my sister in law who I give a big hug to as I feel her breasts against my chest. “How was the drive?” I ask. Monica replies, “not too bad, do you mind helping us with our stuff?”

I nod and begin unloading the car. I grab Monica’s bag and carry it to her bedroom. She quickly follows and shuts the door behind her. Standing there wearing tan shorts, a light blue shirt with her a tan bra strap visible, she begins to start to cry. “What’s up Monica?” I ask

“Jay I don’t know what to do? I owe my bookie $7 grand and you know that I don’t have that type of money. This is going to weigh on me the entire trip.”

“7 grand? I thought you stopped gambling.” Knowing that I’m in a financially sound position I offer to help. “I can transfer the money to you now if you want, but you are going to have to repay me somehow,”

“Thank you thank you,” she replies and hugs me again.

“There it is in your account. Stay tuned for the repayment plan details.” I say as we both leave the room.

—————

Monica is 53 years old and has been single for all I have known. Like most sisters, she is different from my wife. She is a more introverted, and she has a sneaky cute body. She has a nice olive complexion, black hair. She stands about 5’6 about 130lbs with 32c size tits with bigger than average hips with a nice ass.

Monica’s repayment plan will be sexually driven. It will start small, teasing, flirting, flashing, outfit control before I get to do whatever I want to her whenever I want.

Kinks: lingerie, bras/panties, cumplay, oral, anal, creampies, teasing, flirting, handjobs, risky, public, outfit control, blackmail.

Limits: bathroom stuff, gore, death.

Posted Jul 10, 2026, 5:50 PM UTC

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