It is far too early on a Saturday morning, and outside my apartment, the Peaceable City slumbers silently. The empty streets are a still life, a daguerreotype, an idealized architectural sketch, and it is shaping up to be another grey and rainy day. I am going to be hung over. I can tell already: the buzz behind my ears rings threateningly, an angry hive, an unrelenting alarm clock. I want a cigarette, badly, though I haven’t smoked since my senior year of high school. Not tobacco, anyway.
I don’t feel like masturbating, no not at all. I feel like going back to sleep and staying that way, but my body insists, and I am nothing if not a slave to the flesh.
So I roll over, unsnap my rig, and slide out of my harness. Ever since college, I’ve slept wearing my strap-on. It’s sort of like a phallic security blanket.
I let my hand slide inside my boxer shorts, past my scruffy patch and down in between my labia, where my liege and master, that impatient little nubbin Mistress Clitoris lies waiting for my undivided attention.
It isn’t happening. The requisite wetness simply isn’t there. I get up, pee, and swallow a mouthful of water. Then I climb back into bed.
I pull off my boxer shorts and my red t-shirt, and sprawl across the crumpled sheets. My mouth feels like the factory floor of an asbestos plant. Never drink and wallow at the same time: it always leads to disaster.
I close my eyes, and think about one of the first times Jeremy and I were together. Not the very first time. Like most first times that was an awkward experience; rushed, clumsy, hot as a flash fire, sexually unremarkable, and rather blurry in my memory.
This was the second or third time, and though I’m by no means a prude, I’m a little embarrassed to say just how early on in the relationship this was. I think it was our second ‘official’ date, and I think we ditched the ‘date’ part. Such is life.
I was packing, and I wasn’t at all sure how Jeremy would react. We’d been making out in his open front doorway, halfway into the hall, and I could feel his erection pressing against me through his jeans, and I was pretty sure he could feel my own boner through my skirt, and he tugged me back inside in the direction of his unmade bed, and I put up no resistance. I proceeded to spend some quality time sucking his dick: I’d already gotten intimate with his gear, but this was the first time I’d had the opportunity to enjoy him at my leisure, lights on and unrushed, and I was enjoying myself immensely.
And then he reached up inside my skirt, and found my own cock. It was roughly the same size as his, but perpetually firm, and an entirely different shade of electric blue. I wasn’t wearing any panties under my harness, and my cunt was as wet as Niagara Falls.
He didn’t skip a beat; that was the moment I knew he was a keeper. He opened his mouth wide, swallowed more of my hard-on than I would have thought possible, and proceeded to suck my dick while finger-fucking my pussy to a quick-and-dirty, wet-and-squirmy orgasm. Then we fucked.
Jeremy did it to me from behind, jerking me off as he slid his dick in and out of my pussy, and teasing but not actually penetrating my asshole, and I remember thinking it was hotter than hell. My tits swung like pendulums, and my silicone cock felt like an extension of my clit. But he couldn’t come through the condom, so we disengaged, and ended up sitting on his bed, watching each other whack off, which was also pretty damn hot. I’ve always liked watching dudes masturbate. It’s sexy.
Ok, so now I’m plenty wet, and my clit is hard and poking out, and this is happening for a second. And then I think about the very last time Jeremy and I had sex, and I totally lose it. Breakup sex is supposed to be wild, rough, and uninhibited, a last hurrah; ours was saccharine, mediocre and apologetic. Unsexy like a credit card bill. Just like that, I am dry all over again, arid as alkali flats.
I get out of bed all over again, and go for the quick fix: internet porn. I want to watch some videos of cute guys with big dicks jerking off, or jerking each other off, or shyly kissing and giving each other head. But between my antique laptop and my crappy internet connection, it is more frustrating than a fistful of limp dick, and I am forced to fall back on my imagination. Which, when it comes down to it, has always been my drug of choice anyway.
I walked in on my brother masturbating once. Looking back, I’m pretty sure he set it all up. His bedroom door was halfway open, and he was naked on his bed, surrounded by magazines.
He had the biggest dick I’d ever seen, at the time; and at the time (I’m ashamed to say) that was a huge turn-on for me. He didn’t stop what he was doing; he just looked up and leered. I turned right around and ran back to my own bedroom, where I masturbated like a feral weasel. This was before I’d discovered the joys of pornography, and that was the single sexiest thing I had witnessed to date. In retrospect, I’m fairly certain that Leo had intended for me to stay, and maybe join in with him. In retrospect, sometimes I wish I had.
Much, much, much later, I stumbled across my dad’s porn collection, hundreds, maybe thousands of photoshopped and airbrushed pictures downloaded off AOL. His taste was not my taste: he was big on 25-year old cheerleaders and busty women in improbable-looking Little Catholic Schoolgirl outfits, all neatly indexed and catalogued.
The image of my dad, bathed in the blue light of the computer monitor, dick in hand, masturbating to these images is almost painfully erotic. I imagine ambushing him, catching him in the act, wearing nothing but thigh-high stockings and my rig. I sit on his lap, our boners wagging in concert as we browse porn together. I stroke him, and he strokes me. And then he slips his penis inside… I may be a sick little cunt, but at least now I am wet.
Filthy and disgusting. Now things are slippery enough that I can masturbate. As long as I am thinking perverted, disturbing thoughts, I imagine fucking a dog, a big, black, shaggy dog with a long, slobbery tongue, sharp nails, and a fat, bulbous dick.
I manage to rub out a small orgasm. It is distinctly unsatisfying, and leaves me feeling frustrated and disgusted with myself. My hangover is rolling in like the high tide. I decide to take a shower. Lord knows I need one.
Red, red wine stains my lips like cheap lipstick. My mirror image sizes me up. Overall, I don’t look too bad. My tits aren’t the perky things they were back in college, but they’re still pretty cute. I’d fuck me. I crank the water up as hot as I can stand. My mirror-self disappears behind a billow of steam. She’s got a pretty cute ass, too.
In the shower, I think about my college girlfriend, Cynthia. We taught each other about kinky sexy, making it all up as we went along. One time she told me that I couldn’t do anything to her that she’d ever say ‘no’ to.
The first harness I ever bought was made of crappy black plastic that looked awful and fit worse. The dildo that came with it was an obscenely veiny latex schlong, the exact same grey color as cadaver flesh.
I bushwhacked her one afternoon while she was studying. Grabbed a double-fistful of her long, brown hair, and dragged her struggling across the dorm room. Never once letting go of her gorgeous, nut-brown locks, I crammed my dong down her throat until she choked and gagged. While she coughed and dry-heaved, I took the opportunity to handcuff her to the immense Victorian radiator that clicked and hissed and spat. Her pussy was sopping wet, purple, swollen, pouting open and droolingly ready. I poured lube all over my dildo and down between her pale ass cheeks, and shoved my dick up her virgin asshole. Cynthia screamed until I thought she was going to cough up blood. The rest of the dorm must have hated us. She never said ‘No’ to me.
Afterward, I lounged on the bed and stroked my cheap latex dick and ogled while she masturbated. It was the best sex I’d ever had, though I didn’t even have an orgasm. She looked at me like a beaten dog, and we broke up shortly after that, and I went back to dating guys, for the most part.
I only pegged Jeremy once, which is kind of ironic because I’d been wanting to do exactly that to him ever since I first set eyes on his sweet little ass. When he finally asked me, shyly and sweetly, my heart swelled up inside my chest, my clit stiffened and my pussy drooled.
Jeremy was nervous, and crazy tight. I tried to be super gentle with him. I can’t tell you how sexy he looked, splayed out before me, back arch and muscles tense, dick pointing straight out, impaled on my fat blue cock. I think I enjoyed the experience a lot more than he did. He never asked me to do it to him again.
Thinking about all this has made me hot and bothered again. I could masturbate right here in the shower, under the hot spray of water. I even own a vibrator designed expressly for that purpose, a small waterproof unit. I used it on Jeremy sometimes, when I would blow him in the shower: I’d hold it against his soft skin, that spot just below his ball sac, while I sucked his dick. That used to do the trick quite nicely.
But I am not in the right head space for the vibrator. I am feeling perverse and perverted. So I turn off the water, and exit the shower, leaving wet footprints across my bedroom floor. I strap my harness back on, and my cock juts eagerly out in front of me, bobbing as I move. I grab my fleshlight from its hiding place under the bed, and I slather it in lube. The orifice is shaped like a crinkled little asshole, soft and creepily realistic.
I jam my dick up inside. The toy swallows me readily. I hold it still with both hands, fucking it with my hips. I fully intended to start slow and soft and work my way up, but that isn’t happening. I back the toy up against the wall, and slam it with everything I’ve got. Each time I thrust, I get a jolt of pleasure from my clit as it is crushed against the base of my dildo. Harder and faster, and I am grunting and grimacing, the fleshlight is squelching satisfyingly, my dick slides in and out, and I am going to fucking come. This time it is for real. My ass clenches, my toes curl, my boobs shake and my nipples stiffen, and I howl out loud, and keep on fucking. The orgasm washes over me, pounding through me. I am tossed and tumbled, lost in time and place.
It wasn’t the sex that did Jeremy and me in, not at all. It was the Ten Thousand Things. All the small, stupid, mundane, crappy things that just piled on and added up and gummed up the machinery of our relationship until it simply didn’t work any more. Too much weight and friction. I’ll miss him, but now I am ready to face the day.
I take three Advil and get dressed. As usual, I am packing, a smaller, more discreet rig than the one I use for play time. If you look, you can see the bulge in the front of my jeans: a tangible ambiguity.
Outside my apartment, the sun is peeking through the clouds, and the Peaceable City is just waking up.