An Older Womans Mysteries

Our physical difference was striking.

I'm a brute—at least I look like one. Over six feet, with broad shoulders and thick legs, I dwarfed her barely five foot frame. Where I loom, all burliness and beard and full, round ass, she receded, her thin arms and legs topped by a spindly bottom and slightly sunken cheeks that were the most obvious sign of her fifty-nine years. Seen together, we'd look like a mother and her overgrown son—someone in the building trade, perhaps. But we were never seen by other people—our entire relationship was founded on secrets, from the world and from each other.

We met online, of course, that invaluable place of secret lives and secret desires for people who needed them. You're on the site now, so you know—anyone can find a match, no matter what the stipulations. For me, it wasn't overly specific. I slotted myself in the "dom" check-box but explained further how open I was to others' needs. I suppose I'm not unusual in this world—a lonely man in middle age, looking for furtive contact to numb the pain of a life turned sour and painful.

Her needs were more focused. While she, too, has picked a box (the "sub" and her age piqued my interest, as did her location, a mere half hour drive from my Portland apartment), she, too, had more to say about what she wanted. Her description hinted at such—but in oblique terms with the promise of more should prospective suitors ask, and answer, the right questions. After a month of intermittent and escalating messages, I passed the test. Somehow. As I said—secrets.

When she decided—and up 'til a specific point in each encounter, she decided most things—we bypassed much of the online safety protocols everyone advises you to follow. She was no-nonsense like that—once she decided what she wanted to happen, she didn't waste time. As for me—nursing a broken heart, a constant hangover, and mounting depression—I just didn't much care what happened to me.

She cared more about her safety—and her secrecy—but she was also pragmatic about the risks involved in arranging to meet a strange man for...what she wanted. Plus, there were elements to her needs that could only be fulfilled by allowing that stranger (me) to invade her life to a dangerous degree. And so she told me where she lived.

She told me the layout of her yard, her home, her bedroom. She enumerated potential obstacles to my ingress, and possible dangers to being spotted. She didn't tell me much about herself—except that she lived alone in that small, cozy house with the concealing hedge. And I didn't press her for more—I knew what was expected of me, and that was a lot to take in. The controlled terseness of her emails didn't invite further probing and, in fact, carried the implicit admonition that such curiosity would queer the arrangement before it began. And so I held my tongue.

When the day came, we finalized our carefully agreed-upon conditions and limits (most were hers, as made sense). We set the time, and both printed out our agreement. I took the precaution of saving her messages in a separate email as well—her fears were real, but so were mine—and then I waited for the appointed hour. Late—midnight. Her decision as well. And then we did what we had agreed upon.

I knocked on her back door. She answered it, with a convincingly assumed sleepy wariness. I forced my way in past the crack she'd allowed to see through and then I simply overwhelmed her tiny body, my bulk and assurance and—yes—brutality having her on her back on her kitchen floor in an instant. My hand on her mouth replaced immediately with the soft, cloth gag I'd been instructed to use and tied behind her grey-blonde hair tightly once I'd flipped her roughly onto her stomach. Her pale, thin legs kicked frailly from under the terrycloth robe she wore, her blameless white nightgown revealed in her struggles. I stripped the soft cloth belt from the rope and bound her skinny wrists behind her, wrenching them and wrenching a shocked cry of pain from inside her gagged mouth. Then her ankles, pinned against the floor and bound together with a strip of cloth conveniently left draped over a kitchen chair. I flipped her over—hard—onto her back again then and let her see my face—for the first time. No blindfold, she'd ordered, and when our eyes met, her look of fear and undignified helplessness was real enough to make me falter, just for a moment.

But everything was just as we had planned—to the last detail—so it continued.

I had her draped struggling over my shoulder in an instant—I must have outweighed her by a hundred pounds of more. And then I strode purposefully to where I knew her bedroom to be and threw her down on her clean, made bed, hard on her back. The knife then—unfolded to reveal a long, partly-serrated blade. Bought to her specifications. Denuding her was a hacking, brutal affair—fast, and crude, shredding her robe, her gown, the grey, unassuming panties in irregular pieces, stripped away in chunks, leaving jagged strips hanging from beneath the bonds of her wrists and ankles. She struggled throughout, subdued only by the implied threat of the knife, her mewling cries of outrage and anger steady and insistent. Once she was stripped to tatters, I stood, and surveyed my captive.

She was—a nearly sixty year old woman. Pale, thin-looking flesh, puckered with a lifetime's surgical scars and spots. Small tits slid down slackly into her armpits, her movements making their deflated little form shake piteously. Her pussy was a sparse, uncombed thatch of dingy brown. Small blue veins pulsed at her throat, her thighs. Puckers and moles, and wrinkles. I stood, stunned and as hard as I'd ever been in my life.

I'd never seen anything so moving—and arousing.

I stood and watched her struggled and listened to her moans muffled and pleading, and watched the red flush of her efforts and her humiliation spread over her chest and face. And then, deliberately, I undressed.

The sight of me undressing—and no doubt that of my relative massiveness to her—caused her to renew her struggles and her cries. I took my time, letting my size—"burly" would best describe it—fill her fear. When my cock—not enormous, but enormously engorged, finally came into her view, she began to scream. I let her—the thickness of the gag and her house's relative isolation making her protests irrelevant. And then I got to work.

Knifing away the cloth bonds at her ankles, I deftly retied them singly to the feet of her bed, my large hands fully encircling her birdlike shins. Her legs splayed open and her arms bound behind her, her utter helplessness seemingly registers in her with complete finality and she thrashes wildly, her sad, little breasts flapping against her ribs. There are tears in her eyes now as they seek mine out, the pleading therein as eloquent as they are useless. When I kneel before her prostrate little body and thrust my head an inch from the forcibly-parted pink of her cunt, she freezes.

And then I go down on her for hours.

I follow my role to the carefully-worded letter—teasing maddeningly, for so long I feel my cock will split itself with lust—until finally allowing my tongue meaningful purchase on her wrinkled little lips, inside her tiny cunt. When the teasing has gone on for even longer than I thought possible to endure—for either of us—only then do I flick the emergent rose bud of her clit, and watch amazed as her pussy contracts with a visible series of spasms, drenching her already glistening lips and ass with slickness. She thrashes and outright screams then—the pent war within her lost in one final instant of degraded ecstasy.

The sound was unlike anything I have ever heard.

Then, as agreed, she was my plaything. I raped her cunt first where it lay, squelching in a puddle of its own guilty juices—but only after allowing my impossibly hard cock to stroke first against her engorged clit, eliciting another orgasm announced by the most gloriously defeated moan. I looked into her eyes, forcing her face to see mine as I raped her, and saw the tears there, and the shame. I untied her ankles then and, my come still swamping her tiny pussy, rolled her onto her side. She drew up her knees to her fluttering little chest and I—hard again with shocking readiness—fucked her from the side, my thickness finding ingress easier into her tininess only because of our mixed and wanton juices. Throughout the rest of the night, I took her some five times, finishing off with a violation of her creased, puckered little anus. With every endless stroke on her helpless little form, I felt bigger and bigger—my already generous bulk seeming to swell and dwarf her further. And throughout, she stared ahead, when her eyes were open and not clenched tight in shame, eyes swimming with tears, or simply blank. When I entered her ass, she struggled and cried, but her efforts now came from far away. When I finally came inside her asshole, I cried out in exhausted ecstasy and collapsed to the floor beside her. The sun was coming up. I had to leave—that was our agreement.

I took up the knife where it had been forgotten hours before and sliced through the sweat-soaked cloth at her wrists. Freed, her slack, thin arms flopped to the bed. Again, she curled herself into a fetal position. I left her soaked gag in place and slowly dressed myself, watching her tiny body breathe slowly the entire time, seeing my come seeping from her ass and her pussy. She remained still until I reached out and stoked her spindly haunch, at which point, she curled into herself further. I watched for another long moment and then, seeing the sun almost risen, I went out the door I'd come in, found my truck parked two streets over, and drove home.

I showered, wincing at the soreness, and checked my computer. As agreed, the one message: "Yes."

We met again six more times over the next year. Each time a variant of the first, each unique in its own way. All thoroughly satisfying—for me at least. We never spoke in person and, apart from that one word, "Yes," we never wrote about what we'd done, except for a few minor adjustments to her stipulations. (She eventually told me to rape her mouth as well.) The most exquisite image I have of the myriad from our seven nights, is of her tiny body, arms bound as ever behind her, perched straddling my face as I hold her upright atop me. I pull her slim hips with their slack, seemingly-muscle-less thighs down into my mouth and she pleads to be released through her gag as I drive her to another outraged, humiliated release of her own. And then, defeated, she surrenders in shamed limpness as my toy—until the sun comes up.

I never asked her why. Why this specific fantasy? What did it mean? After she answered our last encounter with the single word, "No," her profile from this site disappeared, and so did she. I thought of her often, but never—ever—even drove past her house. The agreement had been made, and I, for all my dark fantasies, am an honorable man. The agreement was deleted, the single clue to who she was that she chose our specific fantasy echoing in my mind, the first line she wrote once she'd chosen me:

"Make me betray myself."