Now that the weather is getting cooler in the evenings, I have started opening my bedroom windows at night. Both windows are directly next to/over my bed, and I love the feeling of the cool breeze tickling my skin as I fall asleep, usually after edging and having a huge, full body, squirting orgasm. I masturbate most nights, usually playing for at least 90 minutes during which time I edge myself closer and closer to cumming. I love to toe the edge of an orgasm, hovering right before the first wave, and then push past it and do it all again. I also recently started playing with anal toys, and that’s added a whole new layer of intensity and excitement to my evenings. Ahem. Anyway, quarantine has been an interesting time.
A few weeks ago, I was lying in bed naked, scrolling through Reddit while one of my toys charged, and I noticed the smell of someone smoking wafting into my room. I peered out my little window… I live in a basement apartment and there are several balconies and patios that face into what is effectively my building’s back yard. I heard the familiar click of a lighter, and saw him — a youngish white guy, medium build, brown hair, wearing a light t shirt and jeans. He was standing on the balcony directly across the yard, leaning on the railing, facing me. A cold shiver ran through my body. Could he see me? Had he overheard any of the clips I had watched so far?
I decided in that moment to fantasize about him watching me. I figured there was no way he could actually see me… but imagining that he had noticed what I was up to turned me on.
I’ve always enjoyed being watched. In my previous job, I used to leave during my lunch breaks, drive to a busy parking lot, and masturbate in the car. I was always towards the back, with trees or a wall behind me, never in any real danger of getting caught. But imagining the “what ifs” was more than enough to get me off over and over and over again. I even started packing my dildo and vibrator in my work bag so I could fuck myself properly in the backseat, moaning as loudly as I dared out the cracked window, certain my car was rocking side to side conspicuously and caring exactly enough to make the whole exercise hot.
One time I went to a tea house and sat in a cozy nook in the back and journaled about a very specific fantasy of mine (will have to save it for another post, but it is related to [this story](https://www.reddit.com/r/SluttyConfessions/comments/i6v5pd/the_f25irst_time_i_fucked_a_guy_i_had_been_out_as/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)), and when I got up to leave I was so woozy from anticipation I did the whole cliché “pulled hard on the door even though it said push” thing on my way out of the shop. I staggered to my car, hopped in the driver’s seat, pulled down my leggings, and fingered my pussy so fast and full that I squirted all the way to the dashboard. It was about 6pm and I’m honestly shocked nobody walking by saw or said anything.
So yeah. When I notice this guy out my window, I think, this is an absolute fantasy. I start playing with my DDD tits, caressing them briefly and then going straight for my nipples, rolling them between my fingers and grazing over the sensitive points with the pads of my fingertips. My pussy was already tingling and I found myself pressing my thick thighs together, and rocking my hips backwards and forwards as my arousal built. I got greedy and reached a hand between my legs, cupping and pressing into my clit through the soft, waxed skin surrounding my pussy. I kept rocking my hips back and forth, writhing, naked, until I couldn’t stand it anymore. I paused and spread my legs wide, parted the wet folds of my pussy to expose my clit, and pressed my index and middle fingers around it. I pressed my thighs together again and resumed grinding my hips into my hand, this time the direct pressure on my clit making me gasp loudly in surprise and pleasure. I looked up out the window and saw my possible viewer had pulled a folding chair up to the balcony, and he was now sitting, leaning his elbows against the railing, his knees spread wide, his drug of choice dangling from his left hand. He was still directly facing me. I squinted but couldn’t quite make out his face… and then he coughed twice AND I HEARD IT. Soo hmm okay… he could probably hear my videos, huh? What about my gasps?
I propped myself up a little so I could see him more head-on (pun absolutely intended). I imagined his cock getting just a little stiffer as he watched me, pressing on the inside of his jeans just enough that he’d have to shift in his chair. I imagined him imagining me, imagining my wet pussy and how badly I needed to be fucked. I imagined him hearing my porn and getting turned on watching me watch a girl get fucked on a nude beach with a dozen people standing around her masturbating. And like I had willed it, he coughed again and sat back in his chair a little, crossing one leg over his other knee. He took another drag. I felt my pussy gush.
Needing more, I grabbed my glass dildo and pressed the tip into my clit, then slid it down so I could feel the pressure all the way down my pussy. The dildo was cold to the touch and the sensation was delicious. I started to tease myself by rubbing the dildo up and down my clit and pressing just the tip inside my dripping entrance, so wet I could hear my own desperation quite loudly. I imagined my neighbor hearing my wetness all the way across the yard and feeling his bulging cock press uncomfortably into his jeans. I imagined him unzipping his pants discretely and reaching for his hardening dick, stroking it hurriedly and trying not to be too obvious shout it.
And reader, I shit you not, this man unzipped his jeans, reached into his crotch, and without any of the discretion I had imagined leaned back and started boldly and decisively stroking his objectively huge cock.
He had to be watching me, right? What were the odds that this was merely a coincidence?? I had grabbed my dildo at some point and had shoved it deep inside my pussy. I paused to consider the thought that… maybe he had just come outside to masturbate, and had no idea I was even here. I shook my head and returned to my fantasy. He had seen me. There’s no way this was random. I started thrusting my dildo hard and deep. Fuck, he was HUGE. Even from a distance, I was absolutely sure of that. I pushed my dildo harder and faster and harder and I felt my g spot swell. I was going to squirt, and soon. I got a few more strokes in and then pulled out and started teasing my clit with the head of my realistic, and dripping wet dildo. I let out a loud, shaky, deep moan that turned into a shout-giggle as my pussy spasmed and gushed and squirted a foot down my bed. My legs shook as I came down from the sudden burst. And I immediately looked up to the balcony to see if there was a response. There wouldn’t be. Right? There’s no way he was actually watching.
But he was. He was standing now, still stroking his enormous cock (like, proportionally, this thing just didn’t make sense on his body!). His jeans were still on his hips but he had lifted his t shirt with his other hand to expose his taught chest. He slowed his deep, strong strokes for a brief moment and then, I’m SURE of it, he raised his hand towards me in a cute little wave. Oh my god. Oh my god he WAS watching, fuck! Fuck yes.
I shoved my dildo back inside my quivering pussy and began to rub my clit fast and hard. I was going to cum, I could feel it. It was too much to resist, living out this fantasy I had had since college, when I would lean against the side of the rec pool while I talked to my friends, letting a jet massage my clit, occasionally doing a lap or two to cool down. I would sit in the back of theaters and play with my nipples until I was close to cumming and then after the movie was over I would run to the bathroom and rub my clit until I squirted. One time I asked a girl I was dating to fuck me in a classroom, and I squirted so much the wet spot on the carpet was still there years later when I visited. And now it was happening. Someone I didn’t know was getting off to me getting off, and right in front of me, no less.
My voyeur friend was basically naked, pants at his ankles and t shirt entirely off now, stroking his cock and fucking his hand at once. I imagined him fucking my pussy that way. Maybe he’d show up at my door. We probably wouldn’t even talk that much. Just strip down and I’d bend him over and let him do…. that. Exactly that. I watched him thrust and I drooled and I felt my pussy starting to clench. I let out a low moan and I think I heard him moan, too. My clit was screaming and twitching and I shoved my dildo inside my pussy as far as it would go, and then picked up my still-dripping glass dildo. I reached behind me and pressed it into my tight but waiting asshole, filling me completely. I could feel the pressure all the way through my now-extremely-tight pussy to deep within my clit, and as my orgasm started to crest, I watched my neighbor lean his cock over the balcony railing, where everyone could see him cum for me. He kept thrusting like he was fucking his hand, and I think I heard him shout with desperation. I released into my orgasm, my pussy gushing again as I yelled out in pleasure and need. I gave my glass dildo one final push into my asshole, clenched very lightly to hold it inside me, reached back around to the big, lifelike dildo in my pussy. I couldn’t move it much with both holes plugged this way, but a little was all it took to send me screaming into a final round of convulsions. Every muscle in my body squeezed and spasmed, I moaned with every peak, and I thrust my dildo deeper every time the waves started to subside. I think I might’ve cum for several minutes.
As I came down and regained some awareness, I saw my neighbor pull his pants back up and heave himself back into his chair. He pulled out his lighter and puffed a few more times while we just breathed and enjoyed the post-orgasm high for a few minutes, and then he got up and went back inside.
I hope he comes back soon!
Source: reddit.com/r/gonewildstories/comments/iudso5/i_f_had_the_best_orgasm_of_my_life_watching_my
Good story can’t wait for the sequel
I wish I was on one of the other balconies
What a nice story