House sitting and cherry picking with nieces lapdoggy

LupusDei

curious alien
Joined
Jul 3, 2017
Posts
4,246
TL;DR: setup for a fairly lame "stumbled into skinny dipping girls" trope.

No incest, although options remain open for a sequel. No bestiality although the doggy loves to sleep under the blanket.

Bro is a bachelor, likely a nerdy guy in his forties or so (perhaps even incel, or adjacent, but that may be too heavy).

Sis and family are going abroad for a vacation (or whatever) for like two weeks or more, but not much more.

She have a house, exurban or country house, perhaps, but not likely "off-grid" (not a farm, a modest residence even if with lots of land, or neighbors having lots of land and lax borders). This may still work with suburban or even urban neighborhoods, but I envisioned it mixed wild/ex-agricultural area taken over by sparse residential, holiday homes, distance work, etc.

Niece has a doggy, a lapdog plaything, but large enough she can't take it on the plane, etc.

House and the dog need a sitter for the duration. For whatever reason, or no reason, closest neighbors are not considered. Daughter's (nieces) best friend (who visits there often) promised to take it, but it fell through at the last minute due to her own change of plans that take precedence.

Sis calls a favor on the Bro, who can't come up with a rational reason to refuse... and ends up stuck, somewhat reluctantly, in an empty house that's not his, with a girl's dog... He is told to pick the cherries that are about to come ripe (there's lots).

The doggy needs walking. So our guy basically follows the dog where it takes him on the roads and trails... eventually leading him to a secluded swimming hole, apparently frequented by nieces local female friends to skinny dip.

The dog will also ensure he can't remain hidden and watch passively. And yes, there's different kind of ripe cherries to pick... if he plays it right by some miracle.
 
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That would be a decent lead in to for of my MILF stories. The young guy (in my version) chases the fool dog, not realizing he's now on someone else's land and runs into Gloria at the swimming hole. Maybe she's married, maybe she isn't but, she's lonely and neglected. The young guy is beyond embarrassed which she finds charming and sweet. She decides they are both going to have a hell of a weekend.
 
That would be a decent lead in to for of my MILF stories. The young guy (in my version) chases the fool dog, not realizing he's now on someone else's land and runs into Gloria at the swimming hole. Maybe she's married, maybe she isn't but, she's lonely and neglected. The young guy is beyond embarrassed which she finds charming and sweet. She decides they are both going to have a hell of a weekend.
If it works for you why not. The guy could then be the dog owner girl's cousin, homeowner's nephew. Or whomever you like. Could even be daughter's... friendzoned not-quite-boyfriend, roped into this somehow... but mostly of course by secret simmering lust for... indeed could be mom as well as daughter. He could be mom's student, or an intern at her job...

Anyhow, it's not like the doggy randomly ran into the swimming hole, although that could work too if you want to.

But what I was about... The guy will be intentionally led there at the right time by the dog, as that's one of places the dog (and by inference, the daughter, or possibly mother & daughter, together or separately) had visited frequently on those walks, a recurring destination he is dying to get to again at preset times, to greet whomever there's not just get wet although he may like that too. Dogs are creatures of strong habits, so there's certain inevitability in this. Even if the guy refuses to go there, or try to stay away after the first encounter, he will have to fight the dog over this, and the dog will run away to get there anyway.

In my version, there's potential interplay: does mother know daughter is skinny dipping? Or is it mother who's skinny dipping there? Does the girl know mom do, or know she does? Or is eiter trying to sneak around the other? Etc.
 
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