The Watcher

Living in a city offers many options for sexual pleasure. There are sex clubs and prostitutes, bars and illicit drugs, and plenty of easy, desperate, lonely people hoping against hope to hook up. Personally, my favorite thing about the city is the apartment buildings. At night, people leave their blinds and curtains open, relying on the anonymity a metropolis promises to shield them from watchful eyes.

But it never does shield them. All it does is allow them to blind themselves in naiveté. This is the innocent little belief I rely on to provide me and my partners with the kind of stimulation I crave. Sometimes, I bring women home, and stand before the window with them on their knees before me, my hard cock driving into their throats, gagging them, while I scour the rooms in view with my binoculars, seeking, beseeching someone to give me what I need. At other times, I will bring home a soft, feminine man, and bend him over, forcing my way past his barrier, and into his tender ass, while watching my favorite "show."

There is a woman living across the street from me, about two floors below mine, who invariably leaves her lights on while she toys with herself, curtains wide as her legs. She owns more toys than shoes, which always gets me hard. I love a woman who knows what brings her pleasure, and takes it. I don't know what her name is, but I think of her as Monica, who was also a girlfriend I had in college. They were both blond with great tits, and though the original Monica never talked about masturbation, I think she must have gotten herself off pretty frequently. She was a really horny bitch.

The Monica across the way has a nice rack for a woman of around forty, and an ass that makes you want to finger her tight little back door. Fingering a girl's ass is such a turn on. They are always a little shy and embarrassed about it, and their blushes, as I drive my fingers into them, sometimes make me cum without even touching myself. Monica has a tramp stamp, and sometimes I wonder if she'd let me bring her back here to my loft, and lay her on the chaise in front of the window, pounding into her blonde furred cunt as we watch together. Maybe we'd watch the guys adjacent to her building, the dom and the sub who are constantly ass fucking. The dom has a big leather paddle that he spanks the little sub with, the marks standing out on his ass for the rest of their session. Or maybe we'd watch the banker who lives below her. He works in the bank I do business with, and loves to gets his ass spread open by big black men with huge cocks while his wife is at work. She is a nurse working third shift at one of the city's hospitals, and loves to have her neighbor and his roommate double team her-- one in her cunt, the other in her ass.

Yeah, I'd love to watch with Monica, but right now, she is getting ready for her nightly ritual. Every evening at 8:30, she turns on her television, I can't see what is on, but she doesn't watch it anyway. I think it's the noise she wants; something to drown out her screams of pleasure as she cums. Once the television is on, she opens up the middle drawer on the right side of her bed, and selects a couple of toys, and a tube of something. She squeezes something out of the tube, lube or some sort of stimulating gel, into her hand, and proceeds to rub her pussy with it. She takes her time with it, working it in all her little folds, and daintily smoothing it on her clit. She pushes a finger up her gap and then pulls it out, and licks it.

By this point in her evening ritual, I am usually pretty hard, but I don't touch myself yet; that waits for the good stuff. What she does next is always subject to change, depending on her mood. One night, I watched her ride a dildo propped on her nightstand, another night, she fucked herself with a champagne bottle. She's into some kinky shit, and I love that. I wonder what she's feeling like tonight.

I'm alone tonight, even though I was hoping to talk our young, innocent, new intern into some fun. If I try, I may get her here tomorrow, but tonight it is just me and my binoculars and Monica.

It was hard to hold the binoculars steady while I jerked myself, so I bought the leather chaise that I lean back on. I had to add longer legs to it so it sat up high enough for my purposes, but thank God for Mr. Thompson in wood shop; he taught me so much that the legs look like they were supposed to be there. So I am sitting on the cool, soft leather, naked except for the cord of the binoculars that hangs around my neck, and I have my lotion beside me. I use an unscented one with lots of Shea butter. The feeling is smooth without the perfumes, and after I have massaged it in, the skin on my cock is really soft. I get a lot of compliments on it, and women love to stroke it. I can't recommend it enough.

But The Monica Show awaits, and I settle in with my lotion in one hand, and my binoculars resting on the ridge where my nose meets my face. I can tell she is really antsy tonight, and her cunt sparkles like a diamond. I am never sure if it's that stuff she puts on or if she's just really wet, but she is always shiny and juicy looking. The dampness of her makes me want to stick my tongue in her hole and suck her until she's screaming for me to stop. Seeing how wet she is gets me fully erect and I grab hold of myself, and begin to stroke-- slowly and gently, I don't want to shoot it before she's done.

She has one of my favorites out tonight, a double pronged dildo that she uses to penetrate her pussy and ass at the same time. I love to watch her shove it up into her two holes, the one so juicy, the other so forbidden. As I watch , she starts to twiddle her clit with the fingers of her right hand, while running her left hand up and down her torso from her neck to her twat and back again. She stops to pinch and twist one of her nipples, and I pinch my own in response. Some guys don't get anything out of nipple pinching, but I'm not one of them. My nipples are really sensitive, and when I pinch them nice and hard, my balls constrict a little at the pain and pleasure I feel.

Monica is moving her hips as she dances her fingers over and around that hard little nub, and then she does something new that I haven't seen before; she slaps it. She slaps it hard, and her hips buck in response. She rolls over a little, and slaps her own ass before settling back and starting to pinch her clit between her beautifully manicured fingers. Her head is rolling a little on her shoulders, and her long blond hair is skipping around her shoulders, tickling her tits. I start to pick up the pace of my own stroking because once Monica gets going, she doesn't take long.

I've watched Monica cum probably a hundred times, and what I love most is the scrunched up little face she makes as her muscles tense and her hips go wild, bucking like a horse I saw at a circus once. And then, the magic happens; she ejaculates. I'd never seen it before, but if Monica is just fingering herself to orgasm, you can actually see her cum shoot out of her wet little pussy. It makes me want to cum just thinking about it, but I can't yet; ladies first.

Sticking her finger up herself, she continues to periodically slap her clit, and I watch as her body convulses with each stinging contact. I would love to slap that hard, pink little clit of hers, while fingering her blonde hole, and I feel my balls contract. Oh shit, not yet. I let go of my cock, and slide my fingers around the base of my shaft, trying to stop my orgasm. But I don't stop watching, and once I am certain that she is getting close, I begin to jerk myself again. Monica stops with her finger exploration and picks up my double pronged friend. Her tongue shoots out to lick it, and her saliva is thick all over both the big head and the smaller, thinner head. She smiles a big lusty grin, and places it between her legs, making a grimace of pain over what I assume is the entrance of the rear head into her tight little asshole.

She is a brave girl though, and works through the pain until I can no longer see anything but the base of her dildo. She starts to move it in and out slowly, and her face is relaxing from the grimace to a look of pure pleasure. Her mouth hangs open, and she starts to lick and suck the fingers she had inside her while she steadily, rhythmically fucks her ass and her pussy with her dildo. Moving her hand lower, she starts to fondle her clit again, while moving the dildo in and out, faster and faster. I am mimicking her motions with my own hand on my throbbing cock.

My balls are starting to ache as she rises up to her knees with one hand on her clit, pinching, pulling, twirling, and the other slamming her play toy into her. She turns around, and grabs the headboard, leaning her ass out toward me, and I watch as she plunges that double headed monster into her sweet, hot asshole, her hips grinding on it. I am almost there, and she needs to hurry if we're going to come together.

But then she stops, and I stop, flustered. She reaches behind her headboard and pulls out a mirror which she places beneath her. In the reflection, I can see her face and her pussy, while I stare right at her tight ass that she fucks for me again. We are picking up the pace, and I am once again balanced on the precipice of cumming without her, but I can see in her face, and the splatters on the mirror, that she is starting to lose control. She starts jerking and arching her back, holding herself upright with her one arm on the headboard, but just barely. Her face contorts in that look I know so well, and I allow myself to cum. I shoot my load all over the window, as I love to do, and then as I feel my PC muscles straining to empty out the last bit, I hold my hand under my dripping tip, catching some of my cum on my fingers. Slipping them into my mouth, I wonder why people think it is weird, but I don't care; I love to taste myself. "Monica would understand," I think to myself as I watch her body relax. She pulls the dildo from her ass and cunt, dripping with the proof of her orgasm, and licks it, rising from the bed. She picks up the mirror, wipes it off with something that resembles a t-shirt, and places it back behind the bed.

She stretches with a leonine like grace, and still naked she walks to the window looking down onto the street fifteen feet below. Tipping her head, she looks up, directly at my darkened window, smiles, and waves.