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.)

“Really.”

“You want to see it?”

“What?”

“Like watch man, you want to watch me fuck her?”

“Ahhhh.” (Both my heads start to throb in tandem).

“She likes being watched. Check it out.”

He went over to a small metal door, maybe the size of a book, on the wall of the house. I thought it was an electrical panel or some shit, but he opened the little door and there was a hole in the wall. He climbed over the futon to the other end of the room and opened an identical panel.

“Look,” he said.

I stepped up to the near one and looked through the hole. I knew that on the other side of the wall was their bedroom. The peep hole looked directly at their bed.

“This one looks toward the bathroom door into into the Shower,” he said.

I was replaying their room in my head. I jacked off in there plenty of times, I never noticed any holes.

“They look through the big mirror. There are a couple spots where it’s two way. You can’t tell from inside. Wicked sweet, huh,” he seemed pretty proud of himself.

Holy shit. A few months ago, in Spring, he asked me to help him hang this fucking huge-Ass mirror. It weighed a ton. It took us all afternoon to figure out how to attached it to the wall so it wouldn’t fall and kill someone. We had to bolt it to a bunch of studs. It was like a permanent part of the house now.

“So, like, wait? Who’s watching?” I asked.

“We have some friends–couples–that like to party, if you know what I mean. I think you met one of them one. Ray and Sandra? Ring a bell? The guy with that purple Tesla.”

Oh, that guy. Who the fuck paints a Tesla purple! His Wife was smoking Hot though. “Yeah, I know who you mean.”

“Well sometimes they come over and watch us. Emily really gets off on it. I talked with her this morning and she said it was cool if I told you about it.”

“Ah, ok. So how does this work.” I moved down to look through the second peep-hole, mainly to hide the fact I had a massive hard-on. In all the slutty scenarios I had Emily play out in my head, this one takes the cake.

“I’ll text you before we get down to business. Like a code word: ‘Peep’.”

“Peep?”

“Yeah. Peep. Like peeping tom.”

No shit dude.

“You want to see anything special? Deep throat? Doggy? Dude, I’ve got some handcuffs,” he was really excited now.

Where were they hiding the handcuffs? “Ah, whatever man,” I replied, but then though, what the hell. “Hey can you fuck her with a giant dildo?” I cringed inside wondering if that was a little too specific.

“Dude, fuck yeah, she has like a bunch of ridiculous shit. All right then.” He put his fist up for a bump.

We finished installing the water heater and I left. I was dying to get home. I pulled out a pair of her panties, and proceeded to stroke a fucking volcano. (Oh yeah, I might have liberated a couple pairs of panties from her drawer. She’d never notice.)

That night about 9:30 I get the text, “Peep peep” with a binocular emoji. I told my dad Jackson needed help fixing the pool light and I was afraid he was going to electrocute himself; I’d be back in a while. I remembered to grab his house key to open the storage shed, but he had left it open for me, and even left me a beer–sweet.

I pulled the chain on the hanging light bulb and closed the door. Looking through the hole that faced the bed I saw the room was empty. I pressed my ear to the hole and could hear faint conversation. I wasn’t sure what to expect. I was sadly still a virgin, but smart enough to know real Sex was not likely to resemble anything I watched on Pornhub. I climbed across the futon and a bunch of boxes to get the other peep hole (someone needs to organize this shit). The doorway to the ensuite bathroom was on the same wall as the bed. From my vantage point I looked right into the Shower; the tub would be off to the right. Maybe she was taking a bath? My mind drifted to all the loads I shot standing at the edge of that tub.

I heard Emily come in the room and I moved back to the bed-view. She kicked off her shoes by the dresser and opened the bottom drawer that had the Sex toys. She dug around with both hands and pulled out two life-like rubber dildos. (Well, maybe lifelike if the dil-model was eight foot tall.) She stood waving them back and forth, “So which one did you want to use hun?” asking Jackson who was out of my view. “Either one babe, you pick. It just sound like fun. I’ve been thinking about it all day actually.” “Ok,” she said. “Go big or go home, isn’t that the saying?” She tossed the smaller one back in the drawer and shut it with her foot.

Standing by the nightstand he took off her shirt, and reach back and unleashed the girls. Finally seeing them untethered, my assumptions where correct. Nice and full, but a bit of natural hang and swing. Big dark nipples too. She pulled off the yoga pants and then her green thong–she wasn’t wasting anytime. I was shocked to see she had some bush. I had pegged her from being totally waxed.

I was already hard as a rock. I pushed my pants down around my knees, but then decided to just take everything off. Why not, I figured, go crazy. She opened a draw in her night stand point pulled out a pump bottle of lube as Jackson came into the picture, walking in front of the bed. He was already naked. This was weird. My pornhub-mind had learned to ignored the actual male body; guys in Porn were more like anonymous flesh-blobs with dicks. I felt a bit uncomfortable seeing someone I knew.

He stood in front of her while she sat on the left edge of the bed. Damn. Jackson had a pretty big dick, and it wasn’t even total hard yet. Who knew? Emily grabbed him without delay and started giving him head. She reached around with one hand and grabbed his Ass while her other hand cupped his balls. (Points to Emily for the ball-play, very thoughtful.)

I started to ponder the logistics of jacking off in this pigsty. I wanted to watch, but that meant standing the whole time, and I wasn’t really keen on ramming my Richard into the wall. I guess I can turn sideways? What am I going to make a mess on? Hummm.

Jackson grabbed the top of her head as she bobbed. Eventually she let his dick loose. Fully hard he was fucking huge. They climbed on the bed and she reached for the lube. She lay back while he knelt down on his heels at her side. Her tits flattened out a bit more than I expected and lulled to her sides, her nipples were big and hard. She pulled her knees up, heels to Ass, and he started rubbing her clit.

I expected some kind of foreplay or kissing or some shit. Maybe once you’re married you just get down to action? I wasn’t going to complain. I hadn’t thought to bring any lube, so I started to stroke it dry. Next time? Would there be a next time?

She lubed up the rubber cock, accidentally spilling some in the middle of her cleavage. “Here you go babe” she said, causal as fuck, handing him the shiny rubber wang. I had the perfect view right up her crotch. She was actually pretty hairy, I surprised that garden wasn’t spilling out her bikini. How did that work? She scooped up the lube off her chest and started stroking his cock. His back was to me. Maybe that was a good thing.

He took the dildo and rubbed it across her Pussy, sliming her up. “Little more,” he said. She pumped another glob right on to the tip. “You know how I like it, just go for it. I want my Pussy stuffed,” she said with an edge in her voice. He position the rubber dong back at opening and then just fucking shoved it right in. Holy shit. I mean the whole damn thing, right up to the rubber nuts. Impressive.

He let go of it and reach up to squeeze one of her tits, trying to coral it with one hand, eventually reaching the nipple and giving it a hard pinch. “Ouch, fucker. What did I tell you about that!” she snapped. “Sorry, babe, can’t help myself.” He let go and slide his hand down her stomach. With her Pussy stretched, her clit popped out of the top of her bush. He started to work it in circles.

She kept up a steady pace on his cock. I would have busted five nuts by that point. Maybe everything gets dull when you’re married? Reaching down with her other arm she swatted his hand off of her clit. “I got this. Pound me that beast,” she directed, taking over the clit duties. “Where do you want to cum to tonight? Face, tits?” she asked matter-of-fact. Really romantic stuff.

He started fucking her pretty roughly with the dildo. I was a bit shocked–this was like something from Pornhub. I had to give me own dick a rest. I was trying my best to last to the end, it wasn’t going to be easy. Looking around I decided I’d just fire with abandon against the side of the house. If I felt inclined I could clean up with the supply of paper towels (but probably not).

Her moans suddenly got loader. I smashed by face back against the hole. “Harder. Harder!” –she was almost shouting at him. Her hand was a blur on the top of her cunt, and her other arm was moving just as fast working his cock. I started to worry she was going to rip off his dick off. Her knees suddenly smashed together; he let go of the dildo; it hung half-way out of her box. He quickly got up on his knees and turned to his right, taking over control of his cock. (It looked even bigger now in profile. I looked down at mine with a grimace). I was jacking hard at this point, ready for launch.

His first load belted her across the check. She flinched, but didn’t seem to mind. It looked like he was intentionally working his way down her body; her neck, then two shots on her tits, and the one on her stomach (show-off). I started cuming now. Shooting into the wall I came so hard it bounced back onto my fist. I had a flash of guilt for making a mess, but I couldn’t take my eyes off the bodyshots Emily was taking, so I decided to just spray my load every which way in tribute.

Out of breath, I leaned my forehead against the wall, curious what happens next in the real world. Jackson got up and walked out. Emily appeared to look straight at the mirror. She ran her hand through the mess on chest. Sticking two fingers in her mouth she slowly sucked off Jackson’s cum. He walked back in and threw a couple Kleenex at her. “I need a Shower you idiot,” she snapped. Getting out of bed she walked right up close to the mirror inspecting the load that was running down her check (oh my god this chick is Hot). She flashed a devious little smile and gave a wave before walking off to the bathroom.

I was super tempted to watch her in the Shower, but I knew that would require rubbing another one out. I wasn’t really interested in Jackson showing up and asking what I thought of the show, mid-stroke, while I was all gooned-out. I threw on my clothes and left. The Shower scene would have to wait.

* * *

The next morning Jackson texted me. “What did you think bro?” (this guy was really something). How the fuck do I respond? “Yeah man, she’s Hot. Lucky you. Thx.” I should have texted the fist-bump emoji, he would have loved that.

Now that I knew exactly what was going on in that side-room-jack-shack, I upped my surveillance game (not that it would have taken much effort to notice a fucking purple Tesla). I definitely thought differently about the stream of friends that filed through there weekend-after-weekend.

Throughout my senior year there were indeed plenty of overnight guests; I witnessed quite a few couples sneak out of the jack-shack late at night. Jackson’s home improvement efforts seemed to slow, or at least he stopped asking for help–or maybe he had second thoughts about asking me to watch him fuck his Wife with a giant dildo and then cover her in bodyshots.