CHAPTER 1 - Jackson, Emily & the Jack-Shack
The house across the street from where I live on Peach Street, has become known as a party vacation rental. It must listed be on some underground site as the ultimate sex party house, because each week--almost nightly--it plays host to some of the craziest shit you'd ever hope to see on PornHub. And I am witness to it all.
The house wasn't always a rental. When I was in high school a married couple lived there; Jackson and Emily. And that's where our story starts.
Roll the flashback music...
Jackson and Emily moved into the house during fall of my freshman year of high school. My bedroom was in the front of the house, and from my desk I had the good view across the street. I watched with curiosity as they moved in; my teenage brain immediately fixating on the hot chick helping unload the moving truck; thinking wow, 'that's the hottest mover I've ever seen'; too stupid to release it was actually the woman that lived there.
Over time it became clear that she didn't work. He would be gone all day and she ran endless errands shopping and going to yoga class (my presumption based on her attire, though in truth she pretty much wore yoga pants 24/7). Every afternoon I'd actually look forward sitting at my desk doing homework, hoping I'd catch her coming or going. And course afterwards I would furiously jack-it to some twisted fantasy where she was the star. The seeds of my voyeur kink were planted in this formidable phase of young-adulthood.
On the weekends, like any well-adjusted teen, I was required to do chores which included yard-work. One Saturday, while pulling like a million fucking annoying weeds from the front yard, he came over and introduced himself and asked if I was interested in making some extra money. He said he needed a hand around the house doing odd jobs; his wife was useless when it came to this stuff, and if it was Ok with my parents he would pay me to help.
His wife was named Emily. They had been married three years. He did something in tech (either I can't remember, or probably wasn't paying attention when he told me), and Emily didn't have to work. They both had nice cars, he worn a nice watch; he must have made good money. He seemed to enjoy doing all the housework himself, though clearly he could have afforded to hire someone to do all this shit for him. And he was smart too, which I kind of assumed based on whatever tech-stuff he supposedly did, but he could literally fix anything. The funny part was that he talked like a moron; like a surfer-turned-frat-boy; everything was 'dude' and 'bro' and fist-bumps. But ok, whatever, he was paying me decent money to stand there and hand him screwdrivers, and I could ogle his wife from close up, and then go home and punch one out afterwards. I was living the teenage dream.
The summer between my junior and senior year they took three week trip to Italy. He gave me a key to the house and ask if I'd water 'Emily's stupid plants', while they were gone. He'd pay me when they got back and I could drink whatever beer was left in the fridge, so long as I didn't do anything stupid. "Sure," I said. Easy money, free beer and an empty house--count me in. Of course the moment they left for the airport I did what any healthy teenage guy would do, I let myself in, cracked a beer and raided her panty drawer. I had pretty much ransacked the place by the time they came back; looking for exactly what I wasn't sure--sex toys, more panties, pictures, who knows. That first afternoon I was satisfied with sticking my face into a pile of her underwear. Unfortunately there was nothing in the hamper; they were all clean. I eventually settled on a pink pair of bikinis and used them to stroke one out in their bathroom. I'm sure you're thinking: a thong is hotter, but there's not really enough material to properly wrap my johnson. I shot a massive load into their bathtub and then rinsed it down.
I really did water the plants--it was a legitimate excuse for going over there every day. It turned out Emily had an impressive stash of sex toys in the bottom drawer of her dresser, hidden under a pile of sweatshirts; a couple of rabbit vibrators, something called a 'clit-sucker', like five different butt plugs, several kinds of lube and some HUGE rubber dildos. I set them all out on the bed one afternoon, cracked a beer and just stared at them. Emily has been in the top five of my jackin' playbook for the entirety of high school. To contemplate her using any of these was almost too much. --I release I have yet properly described her: she's blond, tall; nearly 5' 8'. I think I've said she wears yoga pants like 24/7. She's got narrow hips--not boy hips, but narrow--and her ass is insane; full, high, tight. Fit as fuck. Her tits seems to be natural; c-cups (of course I checked out her bras, duh), but from what I've assessed they have a natural hang to them, a little swing. And she has the face of a model. Jackson did himself well. Anyway, before I put the toys back I'll admit I lubed up a couple of the butt plugs (don't lie guys, we all like a little finger in the ass). The butt plug seemed to short circuit the firing order and I came way faster then anticipated. I completely missed the fucking tub and had to clean up the mess on the bathroom floor.
By the time they returned from their vacation I had made it through the beer, taken complete inventory of her undergarments, masturbated in every room of the house--multiple times--and attempted to return all the toys to the drawer the same way I found them. Oh, and all the plants were still alive. Jackson didn't seem thrilled he had no beer left, but Emily was giddy that I hadn't killed any of her 'plant friends'.
It was the end of that summer, just before I started my senior year, when things got really interesting. Jackson texted me and asked if I'd help him install a new water heater. I loafed over at noon on Saturday. He was in the kitchen doing something on his laptop. "Finally dude, did you just get up," he ask. Dumb question; I'm barely 18 of course I just got up. "Bro, my water heater shit the bed two days ago. Emily told me that if she has to take one more cold shower the only thing I'll be fucking is my own hand."
Just then Emily walked in. "Thank's right!" she chimed in with a wink. She was wearing a bikini that struggled to cover her tits, and rode so far up her ass that you couldn't even see it. She grabbed a bottle of water and went out back to the pool. My head swiveled around like the in fucking Exorcist. I knew Jackson was standing right there, but I couldn't help it.
The hot water heater was located in this shed-thing on the side of the house. In all these years I'd never had reason to go in there. I always thought it looked weird, and wondered what was in it. It ran along the west side of the house--maybe 15 feet long, and stuck out about six feet. Really more of an extra room than a shed, but you had to enter from the outside. He unlocked the door with his house key. I never thought to try that--shame on me.
At one end was a bunch of utility shit; water heater, some kind of junction box with a bunch of wires going in and out; internet or phone, I guess. The other side was an assorted mess of household crap; some shelves with things like paper towels, an old lamp, some books. Furniture too: an old bean bag chair, futon and a small flat screen TV. Kind of felt like an emergency man cave.
As we got to work on the water heater Jackson said, "I noticed you like checking out Emily."
I stammered, "Oh, you mean earlier in the kitchen, hah, yeah, I guess." I sounded like an idiot.
He laughed, "Dude, a fucking blind guy would have had wood this morning. I mean, like always. You've had your eye on her for years."
Oh, shit.
"Brahh, it's ok man. She's fucking hot, huh?"
"Yeah, kind of hard not look, right. You're a lucky guy Jackson." I always figured I could get away with staring as a dopey teen, but it probably looks worse now that I'm older.
"You don't know the half of it man. She's fucking wild," he said.
Wait. What? "Really? Like...?" Please tell me.
"Like in the sack, bro. That shit's lit," his mix of slang was cringe-worthy. "Wasn't really cool to talk about it when you were younger, but now that you're like of-age...man, I gotta brag. She's wild." (I'm still 17 but OK, maybe he can't count.)
