The Key To Feminine Contentment

Chapter Two-2

“Come for me now, boy! Prove my overwhelming desirability by coming for me! Demonstrate your willing acceptance of this submissive experience so I can go all the way on you with full deniability! Come for me right now you little s**t, or so help me I’ll rip your balls right off and stuff them up your tight little bung! Then you’ll never come again!”

And come I did, in wrenching ecstasy, in spasms and spatters and spunky-smelling fountains of slimy hot semen, pumping my issue out all over myself even as I abraded my wrists on the ropes and bit down hard on the wad of fabric filling my mouth. Still Caitlin m*********d me, until every last drop seeped out and dribbled down the wet, glistening head of my erection and onto her hand. Then grimacing with distaste Caitlin climbed off the bed, picked my shirt up off the floor and used the expensive Oxford cloth to wipe herself clean and dry. Then she moved to the window, ran it up and threw my soiled shirt out into the night, where it snagged high in the branches of a nearby tree – joining the tattered rags of nearly a dozen others there. Then she went to my pants, pulled out my wallet and emptied the cash into her own. Catching my wounded eye as she did so, Caitlin grinned at me.

“That’s right, boy. I know it’s a cliché, but you’re being robbed tonight. Education costs money. Maybe next time you’ll think twice before letting a strange woman tie you to the bed.” With that she threw my pants out the window too, followed by my socks and shoes. Then she picked up two more ropes and returned to the bed. There she began tying one around each of my ankles. Briefly I considered kicking or trying to otherwise resist her, but it was like she read my mind. “Don’t you even think about it, boy. If you want me to f**k you, then you remain nice and quiet and submissive while I finish tying you up. You won’t like the penalty for misbehavior in my class, I promise you that!”

Still stunned and reeling from everything that had already happened to me – and tingling all over in orgasmic aftermath – I remained docile, quiescent, and suddenly speculative.

Was she really going to make everything worth it by f*****g me now? If so she’d have to work a lot harder at getting me up than just a few minutes ago. I was utterly spent. But then cruel Caitlin surprised and unsettled me yet again. With her ropes now bound tightly about each ankle she suddenly lifted my legs up high into the air. Bending me double at the waist she raised them above my head, spread them apart and bound my ankles to the same spot on the bedposts as she had my wrists. Then ignoring my frown of puzzled consternation she returned to her dresser and its still-open top drawer.

With her back to me she rummaged around a bit. Then she leaned forward, opened her stance and gasped with excitement as she slid something long up into her p***y. Then she turned back to me, and I got the most appalling shock of my truly naïve young life. Jutting out from Caitlin’s crotch just below that female symbol was its antithesis: a long, elegantly up-curving c**k coated liberally with some slippery substance. How it managed to stay in place I couldn’t fathom. But I knew too well what she meant to do with it. Suddenly my bound, humbly doubled-up posture made perfect sense, as did the confusing sequence of s****l events she’d proposed. Laughing scornfully at my shocked-wide eyes, shaking head and immediate fruitless struggles Caitlin cleared up all the night’s mysteries for me.

“I told you I was going to rob you! You didn’t think it was just your money I was after, did you? Hell no, that’s just an afterthought! It’s your innocence and virginity I really want. Nothing excites me nearly as much as tying up some naïve, young b***h-boy and taking his ass cherry from him! This is called a feeldoe, b***h-boy. It’s a double ended dildo designed to pleasure my womanhood even as it robs you of your still-unrealized manhood.

“After tonight you’re going to be an entirely different, profoundly diminished specimen of the inferior s*x. So go ahead and struggle, b***h-boy – it turns me on. But don’t try to deny your own excitement when it finally overwhelms you. This is education time, and you’re going to learn a whole lot more about both s*x and yourself than you’d ever dreamed possible!”

Pain in my ankles and already abraded wrists made me aware I was indeed struggling wildly, shaking the entire bed with my pointless efforts. Useless as they were however I couldn’t stop myself as sadistically grinning Caitlin bounded back over to me and climbed onto the mattress. This was a dark horror it had never even occurred to me to contemplate, and I could feel myself puckering defensively up now that it was suddenly upon me. Laughing still Caitlin smacked my ass left, right, then left and right hand again and again, playfully b***h-slapping me about as she crouched kneeling below me.

“Oh this is always so much fun!” she cried, her breasts jiggling enticingly and a mad light of excitement shining in her eyes. “Who could possibly be interested in conventional s*x when there are so many tender young b***h-boys out there just waiting to be deflowered? And you know what’s the most fun of all, b***h-boy? That’s when they eventually come to love it; to want it so much that they beg me to become their mistress so I can f**k them like this all the time. But the thrill is in the conquest for me. Once they’re broken in I have no more use for them. And so I turn my little b***h-boys away madly enslaved to being butt-f****d but too ashamed to ask another girl to do it for them. And so they spend the rest of their lives pining for me: robbed not only of their virginity but their peace of mind and ability to be satisfied sexually!”

Caitlin guffawed gloatingly at this, thrilled beyond conceivability by the power she wielded over us pathetic men. But then she got eagerly down to business, once again seizing and squeezing my balls in her iron-fisted grip.

“That’s enough now, b***h-boy. Settle down or I’ll pulp your nuts for you. You’re going to get butt-f****d now whether you like it or not. So relax and make the most of it. I guarantee you’re eventually going to find it helplessly compelling…”

With a supreme effort I stopped thrashing about, more from that threatening crush on my nuts than any of Caitlin’s dubious lecturing. Still I babbled incoherent pleas through the panties gagging me, but these only heightened her obvious excitement. n*****s sticking straight out she shifted closer. And as I at last dropped my useless physical resistance she released my balls and used both hands to grip my butt-cheeks, spreading them even wider than they already were. Still my anus spasmed and twitched and tightened uncontrollably, and again she admonished me.

“Relax, b***h-boy,” Caitlin sternly crooned. “Loosen up or this is going to hurt like hell. Imagine how embarrassing it would be to have to go to the infirmary to get your butt stitched up. Submit to me willingly now, and no one will ever know a thing about this – especially about how much you eventually liked it – but you and me.”

Entertaining supremely satisfying fantasies of punching this evil b***h’s face in the instant she freed me finally allowed me to do as she said. This was just what I had to endure in order to eventually reach that magic moment then I would. And then I’d pay her back in spades for every iota of shamefully intimate suffering she inflicted on me…

Steeling myself I looked down, past my chest (heavily coated with intricate patterns of red and black wax), my abdomen (splattered everywhere with drying semen) and my utterly spent genitals at Caitlin’s own absolutely terrifying prick. Over an inch and a half thick at its base, this narrowed a bit over its eight-inch curve before swelling again into a bulbous head the size and shape of a Grade-A egg. This big oval bulb pressed wetly against my still helplessly twitching opening and I caught my breath in dread preparation. Then with a cry of excited affirmation Caitlin pushed it into me to just past the sphincter.

“Yes! There now, b***h-boy, that didn’t kill you, did it? And now your little asshole forever belongs to me!”

No, it didn’t kill me. But part of me wished it had. That slippery thickness invading me filled me with more than just another person’s p***s. So much sick humiliation swamped me that the pain – which was, in fact, less than I expected – seemed negligible by comparison. My face flushed so fiercely I could feel my scalp tingling, and I had to squeeze my eyes shut in a fruitless attempt to shirk the shameful enormity of the situation. Still there was no escaping the hard reality of that silicon erection as it pushed deeper into me, painfully stretching my circumference and occupying my rectum so undeniably, or of the sound of Caitlin’s triumphant satisfaction.

“There – I’ve claimed you completely now. One of your body’s openings is stuffed full of my pungent cunt and the other my big hard c**k. And now I’m going to start f*****g you, teaching you to love that which you’ve most ignorantly abhorred. Take this to heart, b***h-boy – it will be the most meaningful, impactful, instructive experience of your life!”

Of that I had no doubt. Yet I still felt nothing but hate, shame and revulsion as the raping b***h began pumping her hips, slipping slickly out and then stabbing agonizingly into me again. Slowly at first and then with rapidly escalating speed and fervor she f****d my butt. Refusing to allow me the refuge of denying or ignoring what was happening to me she kept up a constant stream of gloating remarks, rubbing my face in the appalling ignominy of our s****l connection.

“Oh yeah, now we’re f*****g! Now I’m doing to you what you so insolently intended for me. Bet you didn’t think s*x tonight would be anything like this, did you? That’s the attraction we older women have for adolescent boys like you: experience. We can show you things you never dreamed of – or at least never admitted to dreaming of.

“Feel my erect p***s plunging in and out of you! It feels good, doesn’t it? Come on, you can admit it. Feel how it rubs on that little inner nub? That’s your prostate gland – kind of a male g-spot. Next time you’re m**********g, reach up in there and rub that as you do so. I promise you’ll come harder than you ever did before. For now though just concentrate on the situation. You’re being f****d and dominated by a beautiful older woman. There are guys out there who devote their entire lives to pursuing this kind of sublimely exciting s****l experience. And for all your resistance you’ll soon be one of them. I’ve broken in dozens of young guys just like you and I know it to be true. It simply never fails. Soon you’ll be wallowing in this, my latest little b***h-boy. I absolutely guarantee it!”

Yeah, sure! My terrible humiliation only deepened as she continued to increase the intensity of her insidious attack on my ass and personality. And yet once she’d drawn my attention to it I couldn’t escape my awareness of the undeniably arousing rubbing sensation she’d spoken of. It was erotically evocative in an entirely unprecedented way.

Naturally it had never occurred to me, but I supposed there must be something pleasurable about being f****d in the butt. Why else would so many gay guys indulge in such a shameful and disgusting activity? Still I tried to resist this – gay I most definitely was not! But of course a p***s takes orders from no one. And despite the torturous conflict I was undergoing my own soon began to twitch and thicken. From lying limply jostled by Caitlin’s insistent rhythm it swelled and straightened and began to lift itself upright. And right away hateful Caitlin called my attention to this, smugly pressing her advantage as she continued to stroke so maddeningly in and out of me.

“You see, b***h-boy: I told you you’d learn to love this! Who’s got a big hard erection now, huh? And after ejaculating so exhaustively only minutes ago! That’s why I jerked you off just now, as disgusting as I found it: this incontrovertible proof of arousal. It is obvious now isn’t it: somebody here likes being butt-f****d! Somebody’s going to spend the rest of his helplessly submissive life secretly craving it! So take it like a man now, b***h-boy! Better yet, take it like a hungry little slut-slave in hopeless thrall to his clearly divine goddess. Because from now on that’s what you inevitably are!”