The Mammoth Book of Erotic Confessions (32 page)

I ogled him guy-like, from the tip of his brushed blond head to the toes of his high-polish stilettos. I scrubbed under my nose with a pair of fingers, then hooked my thumbs into my belt. I
would’ve spat on the floor, too, to heighten my masculine effect even more, but I just couldn’t muster the saliva just then.

Chris clasped his scarlet-tipped fingers together over the front of his skirt and shyly looked up at me. “You like?” he asked, all peaches and cream.

I nodded, my pussy gluing to the leather platform of my harness with moisture, the flexible dong almost popping my zipper. We’d discussed it for months – cross-dressing – and
now my only thought was: Why the hell had we wasted all that time talking instead of doing? Typical women.

“Looking good,” I croaked, strolling over to the doll, my legs shaking.

He batted his lengthened eyelashes and licked his glossy lips, and my knees buckled. But I stood tall, like a man. I reached out and touched the dude-lady’s bare shoulder with my trembling
fingers. “Yup, looking real good.”

The dialogue wasn’t going to win any screenwriting awards, but the picture was the thing – Chris as I’d never seen him before, me as he and I had never seen me before –
and the acting. I rubbed the smooth, bronze skin of his shoulder, and he giggled.

I trailed the quivering tips of my digits down Chris’s arm, onto his hands, his skirt. Onto the raging erection that the skimpy wrap and a pair of panties could in no way, shape, or form
fully contain. Chris yelped and spun away from me. He gripped the edge of the make-up table, his slender body shaking.

“H-hey now,” I rasped, stroking the cutie’s silky hair and staring at the taut, mounded buns that strained the seams of his short leather skirt. “Ain’t no reason to
be scared.”

We hadn’t really rehearsed any specific roles for the grand unveilings (though I seemed to be channelling redneck right then), deciding to play it by ear. But with the hot blood pounding
in my ears, and pussy, I could barely hear the sound of my own voice, let alone Chris’s.

I recklessly grabbed on to the babe, clasping his hot body tightly against my burning body. I pressed my rigged-up cock into the plush flesh of his bum, gripping his bra-padded breasts and
squeezing. Man, I was as horny as a bullfrog.

I kissed his neck, nuzzled his hair, pasting my long, lean body to his and grinding my cock into his arse. “You want it bad as I do, don’t you?” I breathed into his ear, before
sticking my tongue in.

He arched his back against me in a feminine gesture, and I bit into the heated skin of his neck, inhaling his sweet perfume. “Yes!” he squealed, grabbing on to my head.

Chris and I had engaged in some mild kinkery in the course of our two-year marriage – some fairly well-hidden exhibitionism, a little tentative spanking (on both our ends), a few brief
bursts of phone sex – but never anything this premeditatedly wild. The sheer crazy naughtiness of it all had my head spinning and pussy melting, as I excitedly licked at my
man-turned-woman’s bobbing Adam’s apple.

Moaning, he pushed his butt harder into my hard-on, against my brimming pussy. I sang with sexual electricity. And when he spun around in my arms and I kissed the vixen full on his pouty,
painted lips, it was all almost too much for my addled brain and blazing body to comprehend without premature ejaculation.

But I hung tough, roughly clutching Chris in my arms and savaging his pretty mouth. His cock pressed against my cock, breasts into my breasts. I drove my tongue into his mouth and just about
down his throat, real-man style.

We swirled our slippery tongues together, hot, panting breath flooding our faces. I clawed Chris’s skirt up and over his bum, grabbing me handfuls of thick arse flesh, lacy stocking top
and frilly panty bottom, and squeezing. He moaned into my mouth, his fingers riffling through my hair.

Then the made-up babe was suddenly out of my arms and on his knees on the floor. He tore my oversized belt bucket open and my fly down, pulled my ever-hard cock out of my jeans. Gripping the
pink, vein-ribbed shaft, he looked up at me and squeaked, “I’m going to suck you, mister.”

I grunted something like, “Well, get to ’er then,” and Chris took my mushroomed hood into his warm, wet mouth. I groaned, feeling it right down to my wildly tingling pussy, his
thick lips tugging on my cock head, his hot little hand stroking up and down my shaft. I dug my fingers into his golden hair and rode his bobbing head, urging him to go deeper, suck harder.

He gazed up at me with sparkling eyes and inhaled as much of my cock as he could. His eyes went watery, face red. I pumped my hips, fucking the slut’s mouth quick and hard and anxious, my
pussy smouldering with the pressure.

He gripped my bare butt and hung on. Then slid a hand up and under my T-shirt and squeezed a buzzing breast, tweaked a numb-hard nipple. I almost came right in his mouth.

“I’m gonna fuck you, bitch!” I gasped, jerking my hips back, my cock out of his mouth.

We hadn’t discussed just how far we were going to take things. But there was no room for discussion now. Not in the stifling sexual heat of that ultra-erotic moment.

I pulled him to his feet and dug under his skirt, yanked his pink panties down, my fingers brushing his throbbing erection. He staggered backwards and fell onto the bed. I ripped his panties
away from his ankles and then gripped his spike heels, pushed his stockinged legs apart. His cock stood out huge and rigid above his hiked-up skirt.

I shouldered his silky limbs and then further greased up my mouth-wettened cock with the packet of lube I pulled from my pants pocket. Then I oiled up Chris’s shaven crack.

He shrieked, “Yes, fuck my arse with your big, hard cock!”

“Here it comes, baby!” I hissed, gripping my dong and shoving the bloated cock head up against his virgin opening.

He whimpered, shuddered, as I ruthlessly popped his anal cherry and plunged inside of him. I dug my fingers into his corded thighs, my own thighs bumping up against his butt cheeks, my cock
buried to the preformed balls in his bum.

He squealed and twisted his head around. I pumped my hips, sliding my engorged prick back and forth in the wanton slut’s gripping anus. Surging with raw power and pleasure, I quickly
stepped up the pace, urgently fucking the writhing girly-man, plundering his bum hole.

He grabbed onto his flapping hard-on and frantically pulled, as I clung to his jumping legs and pistoned his arse. The sharp crack of my flying thighs against his shuddering bottom ricocheted
off the walls of the suffocating bedroom and filled our ears, our frenzied breathing and frayed passions crescendoing to the critical point, the wicked sexual pressure too much to contain.

Chris cried out with joy, jerking ropes of semen out of his ruptured cock, coating his blouse and skirt. Just as the wet-hot friction of the rocking dildo platform against my clit sent me
sailing. I shook with one delicious, gushing orgasm after another, coming like a woman as I desperately fucked my man.

Simon, San Francisco

Take it from me: when you’re pushing sixty, there’s a certain slightly queasy charm about having sex with a nineteen-year-old kid who brings along his skateboard. A
kid, that is, like Darrin. When, thanks to the shop-at-home-for-sex services of Craigslist, his baby face first showed up at my door, my dick and I were suitably impressed. Darrin was enthusiastic,
a little goofy, charmingly sweet. He’d told me via email that he was bi, that he’d never had sex with a man before, that all he really wanted to do was just talk . . . Which was fine
with me, if potentially more than a little frustrating. Actually, I’d somewhat duplicitously answered an ad of his that expressed an interest in “furries”, those folks who like to
dress up as animals and sometimes, depending upon their philosophical bent, have sex with other furries while in beastie drag. So for the first ten minutes or so, I feigned an overwhelming interest
in boys in bunny suits.

For his part, Darrin sprawled back in my knock-off Barcelona chair, legs spread wide, basket maybe showing despite his then-fashionably baggy, low-slung pants. Did he realize how provocatively
he was acting? How much I wanted him? Was he as aware as I was that he was damn near young enough to be my . . . grandson?

Yep, long ago, when I saw fellows my age (say, around twenty-three back then) consorting with men old enough to be their fathers – or granddads – I found myself somewhere between
puzzled and aghast. Little did I suspect that, in the jizz-soaked autumn of my years, I would become a Predatory Old Guy myself. Yes, a Vile Seducer. That’s me.

Maybe some of it has to do with time’s winged chariot rushing headlong towards the cliff of mortality; is my desire for youths simply a displaced longing for my
own
youth? Well,
that sounds plausible, but simple fear of death doesn’t really seem to explain my deep longing when confronted by fresh young flesh.

By Darrin’s flesh, for instance. Had he been nervous, albeit charmingly so, when he first showed up at my door? Well, yeah. But then, so was I. Fear of rejection, fear of social
awkwardness. Fear that I’d get what I wanted . . . Which, as it happened, I did. I suppose that, deep down, we both knew what was going to happen. Darrin didn’t object when I slithered
down to the floor, sitting between his feet, stroking my way up his well-formed legs, all the way up to his crotch. Hesitate. Unbutton. Unzip. He let me suck his astonishingly meaty, deliriously
uncut young cock, a cock that was stiff from the moment I undid his pants.

And I soon discovered there were other pleasures to be had. Darrin’s plump rump was not just lovely, but responsive as well, a hitherto unexplored land of heretofore untapped joys. Darrin
had, he told me, played with it himself on occasion, but that had been all, no previous pricks had been in there. (But on the other hand, I later found out that when he’d told me he was
bisexual, that he’d been with women, and that I was his first guy, none of those things – it somewhat disappointingly turned out – was quite the truth. Ah, the stuff we believe
when it suits our egos. And when the guy telling the lies is cute.)

Be all that as it may, Darrin turned out to be a naturally voracious bottom boy, an epochal fuck. As a mostly top myself, I’m always gratified – if a bit stupidly surprised –
to run across a fellow who thinks that getting screwed is the Very Best Thing in the World. Darrin’s collegiate pucker was one of those Holes of a Lifetime. Whether the object in question was
a probing fingertip, my tongue, or my eager cock, his ass was almost scarily insatiable. Had I created a fuck-boy Frankenstein?

It’s not like I ever actually planned to become a lecher. But somewhere around the onset of middle age, depravity hit: I developed a yen for younger, much younger, dudes. I know, I know.
Hardly original – letch-wise, I’m something of a walking cliché. With a hard-on. One that bobbles when I walk.

Sure, relationships are
always
fraught, but falling for a much younger dude is extra-likely to result in frustration, disappointment and unbecoming self-pity. He moves on, you move to a
retirement home.

There were a number of boys back then, some of them beautiful, and most of my dealings with them ended on a decidedly ambiguous note. So by the time I met Darrin, one might have thought
I’d learned my lesson, but no. He – I convinced myself – was different. Hell, he was a vegan anarchist! And he was into me, at least enough into me to let me bust his cherry. I,
the first man ever to fuck him, fell pretty hard. At the risk of seeming an absolute jerk, I must confess there’s something thoroughly bracing about plundering virgin ass. Sure, he was a
little sloppy about answering emails, about keeping dates. But hell, he was young. And a stoner. And cute. And young. Allowances must be made. Even allowances that leave one feeling uncomfortably
close to being a pathetic old fool.

And anyway, Darrin was – for want of a better word – fun. A whole lot of it. Sure, our relationship was pretty vanilla. Well, not all
that
vanilla, especially after Darrin had
smoked a bowl. I did spank him a few times – more than a few – but who doesn’t like to be spanked, at least a little? And yeah, I did drink his piss a few times as it jetted from
his impressive foreskin. It was all rather nice, really. Even the time he showed up just having eaten a sandwich: I still recall the Proustian taste of tofu and onions when we kissed.

But somewhere around our first anniversary, things took a turn for the worse. After nearly a year of on-and-off fuck-buddydom, my calls and emails began to go utterly, unapologetically
unanswered. Several dates were not just cancelled, but thoroughly blown off. I told myself that I was pretty sure that Darrin didn’t actually want to hurt me – hell, he didn’t
even eat eggs. He was busy with classes, he told me. And with his family, who lived, scarily enough, just a short subway ride from my place. On those rare occasions we did get together, it was
often a battle to get into his pants, though get into his now-just-past-teenaged pants I did. But finally the awful truth came out. Darrin had gone on the game. My sweet, innocent boy had started
hustling. Yes, I’d fallen by the wayside when he began selling others what he’d given me for free. Men as old as I was – though, presumably, not working for a freelance
writer’s salary – were paying him 200 bucks for his big ol’ tush. And hey, if there’s anything worse than feeling unwanted, it’s feeling underpaid.

Sure, in my brighter moods, I clearly recall the way that Darrin moaned when I expertly fucked him, how my well-honed butt-eating sent him into paroxysms of boyish joy . . . and what a tasty ass
that was! I just trained his now-profitable collegiate
culo
too well, I guess. I have, though, published a bunch of pieces based on my experiences with him. (In fact, I showed him the first
few, and he was delighted to be a star. And though the last one I published was a lot less laudatory, I doubt he’s seen it. After all, it would be egotistical, even a shade pathetic, to
believe that our time together has left him a fan of my writing.)