It was about midnight, the house was quiet, and I was bored out of my mind.  I was only a few months from eighteen, and I was still saddled with the while you’re under my roof thing.  So, out the window I went.  A quick walk across the laundry room roof to the clothesline pole and a drop to the ground set me free.

I didn’t have all that many options available to me.  One of my friends who lived within reasonable walking distance was at his dad’s place for the weekend.  The other was on a family camping trip.  Going anywhere near main street risked encountering a police officer, which wouldn’t end well.  That left Jason.

I don’t know what you would call him.  He was kind of annoying, so none of us really hung out with him all that much.  His only endearing qualities were that he had a pool table, an older brother who sometimes snuck him beer, and a mother who let him get away with murder.  He’d more or less bought his way into the fringes of our circle with that as currency.

Sneaking around by yourself was as boring as sitting at home, so I plotted a careful course through the alleys and side streets, avoiding outdoor dogs and busybodies who were known to be up late.  It was a bit nerve-wracking to walk down the road in the ritzier neighborhood where he lived, but I didn’t see any cops or signs of life.

When I arrived, the house looked dark, but that didn’t necessarily mean anything.  Jason’s room was on the back corner of the house, and the basement windows weren’t visible outside the privacy fence.  There was also no way to know if his mom was home without getting through the fence gate, because the garage door didn’t have any windows.

She rarely was.  Rumor had it she was kind of a slut, and most of her dates were overnighters.

Relief washed over me once I was inside the privacy fence.  As long as I was there, I was safe from police patrols – which were much more frequent in the richer neighborhood.  I walked to the back yard and across the patio to see no light coming from Jason’s room.  A quick look confirmed he wasn’t in bed or playing video games in the dark.

That only left one last hope.  A look around the corner of the house revealed light streaming from the basement windows.  I walked up to the first one, leaned down, and carefully peeked.  He wasn’t playing pool.  I moved to the next one, leaned down, and got the surprise of my life.

There on a couch below the window was Jason’s mom.  She was naked except for a pair of black stockings – and jamming a dildo into her hairy pussy.

I quickly leaned out of the window to avoid being seen.  My heart was racing.  The smart thing to do was get the hell out of there quickly and quietly.

My rapidly hardening dick overruled common sense.

I moved back a little and got down on one knee where I could see into the window.  She was facing away from me, her eyes were closed, and it was dark outside, so I hoped I wouldn’t be too obvious.  Even though I’d only seen her a few times, I already knew she had really nice tits.  The way she dressed called a lot of attention to them.  They certainly had my full attention bare and quivering from the motion of her hand.

She reached up and squeezed the left one as I watched in aroused wonder.  Fuck, she was hot.  I could have done without the hairy pussy, but it sure as hell didn’t bother me in that moment.  She pinched her nipple, and it looked like she was doing it hard.  Her back arched and her mouth dropped open.  I caught just the faintest sound of a whimper through the glass, and it made me really wish I could hear more.

She was writhing and obviously making sounds I couldn’t hear as she steadily buried that veiny plastic dick in her pussy.  It was like a porno come to life, but so much hotter because it was real and someone I knew – if only a little.  She must have been wet as fuck, because I could see her pussy juice all over that dildo.

I had to squeeze my dick because it was throbbing like mad.  I took a quick look around, thought about how far away the neighboring houses were from the privacy fence, and gave in to what my dick was screaming at me.  I pushed down my shorts, grabbed my hardon, and started stroking.

Jason’s mom pulled that dildo completely out of her pussy as I jerked and watched her.  She twisted something on the black base of it, and then pressed the head of it against her clit.  It was all I could do not to groan when I could hear the yelp she let out.  I’d seen enough porn to realize it was a vibrator and not just a dildo.  She was using it on her clit, and it was making her writhe even more.  Her other hand was busy squeezing her tits and pinching her nipples.  She even yanked the right one hard enough to make her tit stretch out and then snap back when she let go.

Right after that, she rammed that plastic dick back inside her and fucked herself faster.  More yelps and whimpers penetrated the glass to reach my ears, making me stroke faster.

I could see her face getting red, and mine was getting pretty hot as well.  I was starting to feel the itch, so I slowed down.  She certainly didn’t.  After a minute or so, she shifted position, scrunched up a little, and used both hands to ram that dick into her pussy.  It also pushed her tits together, making them look even bigger and really jiggle.

Not long after that, I saw her face tighten up and realized she was going to come.  I let loose, and the fap sound of my fist sliding over the head of my dick was almost as loud as her squeals and yelps coming through the glass.

Jason’s mom buried that plastic dick into her hairy snatch one last time, lurched, and let out a scream that I could hear as plain as day.  That was the point of no return for me.  A grunt stuck in my tight throat as I erupted and shot cum out into the grass.

Fuck, I came hard watching her flop like a fish out of water and hearing her scream.  It was easily the hottest thing I’d ever seen in my life.  She was still bucking and thrashing once I was dribbling cum down my fist, and I had to sit down on my butt to avoid falling over.

I couldn’t take my eyes off her, even though they were trying to drift closed.  She slowly settled and let her left arm fall limp at her side.  She pulled the vibrator out of her pussy and I shuddered violently when she put it in her mouth to suck her pussy juice off it.  When she pulled it from between her lips, she sat it at her side, and rocked forward as if she was going to get up.

That’s when post-nut clarity kicked in with a vengeance.  I scrambled back away from the window.  I realized I had cum on my shorts as I pulled them up.  I got more on them, my underwear, and my shirt from trying to cover my dick up.

I snapped my hand as I walked on wobbly legs toward the back yard, trying to fling the cum stuck to it off.  Most of it just ran down my fingers.  They were already a lost cause anyway, so I wiped the rest off on my shorts.

My anxiety was through the roof as I hurried – as best I could – across the back yard.  I made it to the gate without incident.  I felt relived for a fraction of a second once I was outside the gate.  Then I realized if I got stopped by the cops, not only was I going to get in trouble, they were going to see me with jizz all over my clothes.

My nerves were on edge the whole way home.  I didn’t really relax until after I’d grabbed some shorts and underwear with my left hand, washed my dick and hand in the sink, hid my jizz-covered clothing, and climbed into bed.

The fresh memory was vivid in my mind’s eye as I lay in my bed.  I ended up cranking out another one before drifting off to sleep.

****

She was pretty much my whole spank bank for a few days after that.  So, when she came walking toward me while I was outside taking a vape break at work, I absolutely froze.  The top she was wearing showed off a lot of her cleavage anyway, but in my mind’s eye, those tits were bare and bouncing as she walked toward me.  I could see them as plainly as if it was real.

I don’t even remember what she said as she greeted me, or how I responded.  I was fighting to keep my eyes away from her tits – and not doing a very good job of it.

I nearly died when she raised her phone in front of me and I saw a cropped, grainy picture of me staring through her basement window with wide eyes and a gaping mouth.

She chuckled and said, “I had to do some creative cropping of that video and delete the original because certain things that were on it could have gotten me arrested.”

Fuck.  She’d watched video of me jerking off to her through the window.

“Don’t worry.  I’m not going to say anything to anyone,” she said.  She then turned her phone back toward her, tapped a couple of times, and faced the display toward me again.  It said image deleted.  “I just thought I’d warn you that you’re not quite as sneaky as you think you are.  As strict as your parents are, you might want to be a little more careful until you turn eighteen.”

I swallowed hard and nodded.

“When is that, anyway?”

“September,” I answered.

“September what?”

“Fourteenth.”

She nodded, and gave me a crooked, sultry smile that made me break out into goosebumps.  She once again tapped away on her phone for a few seconds, and then slipped it into her purse.

“Glad you enjoyed the show,” she said.

With that, she turned and walked away.  My eyes dropped straight to her gorgeous ass in a tight skirt.  When her hand appeared in front of it and she waved her fingers, I snapped my eyes upward to see her looking knowingly over her shoulder.

I heard her chuckle as I stepped back out of sight and sat down to calm my nerves – and talk down my dick.

Needless to say, she dominated my sexual fantasies for a good while.