Peeping Tim

by Nicolo Parenti

Copyright© 2015 by Nicolo Parenti

Voyeurism Sex Story: Skulk along with Jamie and Tim as they wend their way from window to window. Their sexy neighbors unwittingly provide entertainment and inspiration for this kinky couple. Could they be watching you?

Caution: This Voyeurism Sex Story contains strong sexual content, including Ma/Fa   Mult   Consensual   Lesbian   BiSexual   Heterosexual   Fiction   Swinging   Gang Bang   Group Sex   Orgy   Interracial   Oral Sex   Anal Sex   Masturbation   Sex Toys   Cream Pie   Voyeurism   Double Penetration   Analingus   .

As a kid I was a looker, a watcher, interested in what goes on behind the closed door, what's in the locked box. When you're young everything is a mystery and any chance to penetrate those mysteries is a golden one. Every lighted window on a dark night is an invitation to the show. Most young people grow out of this. Some grow up to embrace it.

Jamie and I (I'm Tim) fall squarely in the latter camp. We've been together since college but only later discovered we'd both been drawn to the glow of a bedroom light from an early age. I don't think it shows. We're pretty normal, in our early thirties, well-spoken and pleasant enough to look at (Jamie more than me). I'm about five feet ten and 160 lbs with most of my brown hair intact. Jamie is five-four in sneakers, with medium length auburn hair, hazel eyes and a slim but womanly body. Really, except for the fact that we like to spy on our neighbors while they fuck, we're a lot like everyone we know.

Our current escapades started as a lark, inspired by the layout and landscaping of our condo complex and others in the area. I like to say it was her idea but really it sprouted organically from both of us. Since we shared a kink, acting together wasn't any kind of stretch. Plus, a single man on the prowl may seem suspicious where a couple wouldn't.

On a typical summer's eve, if the weather was fine and the moon in cloud or shadow, we'd stroll through the neighborhood like any other couple. The difference is we then ducked behind privet hedges and along back walls, places those inside assumed were safe from prying eyes. Nope. Our eyes pried. And the things we saw kept us entertained, occasionally surprised, and often sexually charged. Not every stroll bore fruit, but enough did to keep us going.

If you lived in our area we may have seen you fucking. Oh, sorry, making love. If you walked naked from the shower, assume we ogled your dangly bits. Did you like to be tied down and tickled or flogged? Yes, we know. We saw.

And maybe you were with your spouse, or by yourself, or with someone else's spouse of either gender. Maybe you groped in a group on a raunchy Saturday night, or snuck in a friend when mom and dad were away. Maybe you hid your drugs or your guns or your money in the closet. I say it now: You should have turned off the lights and closed the curtains all the way. A crack is all we need.

I can't begin to relate everything we saw and frankly much of it is mundane. But there are a select few tales I think are worth telling, of nights when the promise of our skulking was fulfilled. Don't worry, I won't name names. You may recognize yourself or your peccadilloes but no one can connect them to you. Well, Jamie and I can but we're discretion itself.

The Masturbators

One night was a three-fer. I know it's odd that something as ordinary as masturbation would rate a mention and yes, after nudity it was the most common sight in our wanderings, but bear with me. I won't recount the many scenes of guys fapping away to internet porn. It got to where unless there was an odd quirk or a huge dick we'd just move on. Jamie likes big cocks so she kept notes on where they could be found. It's like seeing the dealer's hole card - inside information stowed away for later.

A fine evening in early fall had us in a passageway alongside ... well I said no names didn't I, and that should go for addresses too. So let's call it Building M. The rear of three apartments faced us, each showing a light. There were no windows on the wall opposite so the occupants assumed they didn't need caution. Thank goodness.

On that night two of the rooms held single men. One of them was reading "The Hunt for Red October" (we were so close we saw the title), pantsless and diddling his semi-soft dick, either just starting or just finishing a yank. His cock was of ordinary size and girth so Jamie signaled me to bail. As I reflect on it the interesting thing is that he was getting off to a Tom Clancy novel. Ah, the endless variety of sexual experience.

Next door a guy in his late teens was furiously whacking to a video of two slender lesbians (what passes for lesbian in porn). Jamie paused us here because this guy sported an impressive tool. He was close to getting his nut so we waited until his knob purpled up and he spewed a hot cupful onto his chest. Jamie was rubbing herself at the sight and resolved to run into him at the supermarket or laundry. She got a cheap thrill from chatting with a guy when she secretly knew how he was hung, the volume of his spunk, his porn preferences and so on.

If only he'd known that just feet away two young women were engaged in some of the same play being simulated on his laptop. We'd seen each of them on earlier outings and knew their sexuality wasn't fixed on females. More than once they'd entertained men in their rooms, so this was probably just for convenience. No penis? No problem. It was sort of sad there was a hefty cock just beyond their shared wall that would have happily satisfied both of them, and no one knew it but us. We should be matchmakers.

One of the girls was cute and petite with breasts that suited her size and nipples she'd tweaked into prominence. Juices ran from her puffy labia through a wispy bush that showed she was a true blonde. Her friend in need was a redhead with perky tits just a bit too large (yeah I know) for her frame. We couldn't tell if she was a natural red because her pussy was as bald as Vin Diesel. Not that we could see much of it since it was covered by her palm. She seemed to be missing two fingers. Oh, wait.

They'd started out in facing chairs, turning each other on with the sight and scent of glistening pink. As things heated up a dildo came out and the hum of a vibrator mixed with moans of pleasure from Blondie. Red moved over to help out and soon had her pal panting as she plunged the buzz toy into her pussy and then worked it into her tiny puckered asshole.

Blondie came hard in a series of frozen shuddering orgasms that went on for about a minute. As she recovered Red took up the action, pressing her hand into her own crotch and stroking in mad circles. She located the discarded vibrator and nastily sucked it clean, savoring the taste of the holes it had just pleasured. Blondie repaid Red's favor by helping her aim for the places she couldn't see.

While this was going on Jamie and I weren't just passive observers. I haven't mentioned that on our nights out we dressed in loose black clothes with no underwear so we had easy access to each other's pleasure spots. Right then I was accessing one of Jamie's with mine.

As for these girls, I'm strictly hetero but Jamie will swing whatever way the situation dictates. I'm happy that men are her primary focus - because I am one - but equally pleased that we can share a lady when the occasion arises. Jamie would gladly watch two dudes blowing or boning each other, but aside from how hot that got Jamie it did nothing for me. However we both enjoyed watching two (or more) girls going at it.

Anyway, this wasn't so much lesbian action as mutual masturbation. Which is fine, it still turned us on. As Blondie guided the vibe into Red's rear, I'd already lowered both our slacks and was fingering Jamie's bunghole in turn. My hands stroked up her flanks to tweak her handfuls, leaving my stiffening cock to take over the job of teasing her with its twitches.

The feel of the night air and the knowledge that at any time someone could stumble upon us, unlikely as that was in this dark corridor, soon had Jamie squirming against me, her dripping pussy seeking penetration. With a twist and a hitch she lined us up and I sank deep into her hole. I grabbed her hips, fucking her silently and deliberately as she pressed against the wall, never closing her eyes to the spectacle that held us here.

Red was approaching orgasm, frigging her clit and pinching her nipples as Blondie pumped her holes with the humming probe. A flush spread to her chest and neck, signaling her impending climax and then she was there, her cries audible through the glass. Jamie couldn't hold back so neither did I. My bursting cock flooded her with more blasts than her pussy could hold and she bit down on her arm to keep from exclaiming her joy aloud. When I withdrew, my load ran down in strings from her gaping pussy. I had to brace her to keep her from collapsing.

We pulled up our soggy slacks and departed with a last look at our young muses. They'd retreated to their chairs and were lazily fingering themselves in afterglow. I sensed another session soon but we wouldn't be here to observe it. This was the end of a good night out.

I don't want to give the impression that this happened every time, far from it. Many times we caught nothing in our little excursions and even when we did get a hit it wasn't often with people as inspiring as these two lovely lasses. When it all comes together it definitely makes our week.

The Fuckers

Fat people fuck. Old people, ugly people, plain people - they lick and suck and fuck like everyone else. You may know this intellectually but we know it because we've seen it. Not everyone has the looks or stamina of porn stars nor can we all achieve the positions they get into. But there's enough variety and ingenuity out there to delight even veterans like us.

Now don't tune out: I'm not going to write about fat old ugly sex. I just want you to appreciate that when you take on an adventure like ours it's not the same as selecting the skinny-with-tits channel on a porn site. Often enough you take one look and mentally write a note begging them to draw the drapes. I never again want to watch an old lady sucking off her poodle. Once was too much: it was and remains a uniquely disturbing scene, one I'm stuck with forever. You can't unsee shit like that.

So let's talk about the good ones. Like Brent and Claire (not really), a handsome young couple whose bedroom window was a regular stop. We knew them from around town and the complex. We always had a smile for each other and would sometimes visit over coffee at a local cafe. Casual acquaintances, not exactly friends but friendly. He was a solid six feet, trim and fit with steel gray eyes and a square jaw. Early thirties like us. She was just as trim, a Nordic beauty of 5 feet 7 or so who filled out a sweater nicely. Her pale blond bangs and chiseled cheekbones gave a first impression of chilly aloofness that was countered by a warm grin and friendly green eyes.

It really is titillating to converse with people when they have no clue what you know about their sex lives and kinks. I noted earlier that Jamie gets a charge out of chatting up guys whose dicks she's catalogued and it's even more true for a couple.

Their best attribute was a refreshing lack of sexual inhibition at home. Jamie and I knew every inch of their unclothed bodies, and what they liked to do when they thought no one could see. Perhaps the most memorable night was when he took her ass for (what we assumed was) the first time.

That evening had offered only meh moments: a mousy woman and her little toy; an old man squeezing out a dribble of spunk with heart-straining effort; two frat boys in a sweaty sixty-nine. Nothing was riveting or worth describing, so we headed over to Claire's in a kind of 'Old Faithful' moment. Brent was often out of town but when he was home they were a good bet because they fucked a lot and never closed the blinds.

It was nearly ten thirty which is prime time for bedroom activity around here. From their window it was a straight shot through to the bath. Brent was on his back, nude and floppy, while Claire finished a shower. I started feeling up Jamie to get her motor revving and to pass the time until the action started.

Our timing was great: in a few minutes the bathroom door opened on a gloriously naked Claire, her blond bangs in a towel turban. She gave Brent a quick kiss, then laid down next to him with all her charms on display and shook off the towel. Her tits didn't sag and her spread legs showed she trimmed but didn't shave. As she fiddled with her pussy we got a good look at her freshly washed crotch, right down to her small tight asshole.

Her hand strayed to Brent's limp dick and started to tug and tweak. It's natural to wonder how he could be soft in the presence of a beauty like Claire who was plainly ready for sex, but if you don't get it you've never been in a long-term relationship. Even the finest of bodies will start to seem ordinary after a while. Steak every day, ya know?

But Claire was determined and Brent was receptive so with a little oral encouragement it wasn't long before it was long and hard. He rolled over and shifted to get his face in line. He knew this pussy and while his head blocked our view it seemed that at the very least her clit and lips were under expert assault. Her head fell back and she grabbed his ears. His efforts soon had her moaning and humping, and in just a few minutes she pulled his head up and told him, we could see it clearly, to fuck her now.

There must have been some negotiation because he didn't just jump up and hop on. She shook her head and we could lip-read the word 'pussy'. He wasn't in the mood for refusal. After a couple of rounds of yes/no please baby she gave in and grabbed some lube from her nightstand. Brent flipped her over and she buried her beautiful face in the pillow. He spread her cheeks to work the lube along her crack from her pussy up to and into her asshole, first with one finger and eventually with two.

Having done the prep he switched gears, well, holes, and eased his nicely sized ("Jamie Approved") cock into her pussy from behind. He hitched her up on her knees into doggy-style, to Claire's vocal approval. He was stroking quickly and smoothly, a well-lubricated fuck machine that had his wife pushing back for more and harder contact.

Jamie and I were busy too. I'd found my way into her from behind as I usually did in these situations so we could both follow the action. With the window closed Jamie could afford to be a little bit loud but for safety I stifled her with my hand. She got the message and piped down.

I'd looked away for a moment and missed a shift in position. Claire was now straddling Brent and riding his cock cowgirl style, her luscious breasts thrust forward for him to cup and squeeze while he rubbed and tweaked and lightly pinched the nipples. I did the same to Jamie's sensitive tits.

Within minutes Claire stiffened and gave a long low howl that Brent took as a signal. While she was still suffused with the glow of orgasm he pulled out and aimed his still unrelieved cock at her back hole. She was reluctant but he was not to be denied. They wrestled just a bit, enough for Brent to get her on her back and lift her legs toward her ears, exposing to all of us the little dark place he wanted to penetrate.

She half-heartedly tried to squirm away, but her position didn't allow much movement. We saw her acquiesce and submit, and apply more lube to his rigid dick. He pressed the fleshy tip at the seemingly impossible entrance and to Claire's surprise she began to open up. He encouraged her to push out to ease the way and just like that the head was in. She held steady as he eased in, pulling back an inch for every two he gained until he was fully seated. Claire had grimaced at first but now that he was inside she relaxed and made a comment that caused them both to laugh.

After a pause to accommodate his girth, she told him to go ahead and fuck her in the ass. He pumped slowly to start and then as she realized it was OK, faster and deeper until he was reaming her with the full length of his thick cock. Her pussy was exposed, flowering and running freely with her juices, which added to the lube. With a free hand she rubbed herself and it only took about ten minutes for the friction on her clit and the action in her ass to produce a tremendous climax. That in turn set off her husband. He tensed and came, holding his cock head just inside to flood her guts to overflowing with his pearly load.

You won't be surprised we had our own climaxes while this was going on. I didn't take Jamie in the ass, and we beat them by a mile to the finish line, but overall it felt like we'd shared a fuck with this hot couple. It was nice to have been there when she lost her butt cherry, or so we assumed from watching them. But who knows, it could have been a game they played often, The Anal Virgin and The Insistent Plunderer. After all, we didn't watch them every time.

We stole away and left them to their murmurs and cuddles. Jamie had wished in the past we'd snapped some pictures of the sights we'd witnessed but after talking it over we decided the risk was too great and our memories would have to be enough. Though this was one time when we both said later we should have taken souvenir shots.

There's more about Brent and Claire, or at least Claire, but there are also other tales to tell. I'll get back to that later.

The Group

Only rarely did we come across anything beyond one-on-one sex in various gender pairs so when we did it could be a treat. I say 'could' because as you surely know, not all people are beautiful people. That's especially true when they're naked. All sorts of folks get into swapping and threesomes but our complex has a pretty good proportion of young singles and college-age couples so odds are if it's happening here at least it isn't among a desperate older set. Call me crass but we're in it for our own pleasure so dammit, we want to watch cute and handsome people fuck.

A chilly spring had limited our outdoor activities so we were almost giddy when June came and the evenings were better suited for our walks. A number of tenants had come and gone so our mental maps of the good spots needed updating. No better excuse to scout around. After quite a few duds we found ourselves at Building G peering into a living room, not usually prime viewing for us. This one held three couples with a fourth just visible off in the kitchen.

It could have been a small cocktail party - everyone held a drink - but the vibe was more charged than that. One couple was chatting by a long sofa. She was in her mid twenties, maybe 5 feet 4 with a tiny waist, olive skin and dark flashing eyes that showed amusement at something he was saying. He was a few inches taller with fair but tanned skin and rugged good looks, about the same age as everyone else. I'll call her Maria, him Justin. No real names of course, even if we knew them.

The others included one statuesque black woman (Nita) being nuzzled by Stan, a tall slim pale man with the hands of a basketball player. One of those hands was firmly set on Nita's fine booty which didn't seem to trouble her. Just beyond them was Sandy, who had a sunny smile and a blond mop that made her look vaguely athletic in a cheerleader / volleyball way. She was animatedly describing something to a handsome black man (Don) who towered over her 5 foot nothing frame. I think she was talking about fishing because she had her hands out about a foot apart to show the size of her catch. Or hmmm, maybe not a fish.

The last pair drifted out of the kitchen. Bill and Shelly? I'm running out of fake names here. Bill was a dark and bookish man about 5 feet 8. Shelly was a bit shorter with an appealing roundness and a pixie face. It didn't seem likely the current pairings were their everyday ones. For instance we knew Don and Nita casually as a couple, and maybe Bill and Maria? As for the others I couldn't guess and it didn't matter anyway. They were here to swap and share and we were here to watch.

One bedroom shared the outer wall with the living room, so we had two views on the festivities. We backed away enough to watch both at once. A low pulse of music drifted out to us, the beat evocative of dancing or sex, which I'm sure was the idea. A joint appeared, then another, and the crowd drifted together to pass them around. Jamie and I looked on jealously.

The smoke and drink had the expected effects. The talk got a little louder and the music was cranked up to match. Justin and Shelly drifted off toward a back bedroom, but not everyone needed privacy. Sandy was doing a dreamlike solo dance for Stan and Don. She peeled off her top to expose a nice rack that swayed with her moves. Stan helped her slip off her skirt; Don dropped his trousers and briefs to display a black snake that moved in time with Sandy's tits. And the party was on.

With Don and Stan teamed up on Sandy, in the near bedroom we had the opposite grouping: Nita and Bill joined by the petite Maria. We couldn't see the bedroom where Justin and Shelly had gone but that still gave us two tableaus, and choosing which to focus on was tough. As soon as we concentrated on one, something in the other drew our attention away.

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