Caught, Taught, Tamed & Trained

Chapter 2

So upset was poor Sam that he barely registered the glorious sight of Ms Phillips’ breasts shifting and swaying as she secured and tested her fit, tugging on her new erect c**k. But at last he mastered himself, dropping his gaze just in the nick of time. An instant later Mistress straightened up and strutted back over to her new captive boy-toy.

“Many slutty little boys dream of having s*x with their Mistress,” she lectured. “This is of course impertinent, inappropriate, and terribly misguided. Learning discipline means learning to always submit, entirely and wholeheartedly, to every whim of the ruling Mistress.

“She may, if she chooses, use s*x as a tool in her training of you. But in order to punish and eradicate that ridiculously improper f**k-dream, she will almost always invert the normal male-female relationship. The boy becomes the b***h, in other words, and as the dominant partner it is Mistress who wields the c**k. Now I know you’re a virgin to this kind of s*x, slut-boy, so I’m going to let you start by servicing me with your mouth. That should provide us with sufficient lubrication for later.”

Suddenly Mistress stood right in front of stunned Sam, and again she had him by the hair. This time she pulled his head up, allowing his gaze to feast on those matchless legs before finally confronting him with a much more daunting feast.

Her big rubber prick was right in his face, and nudging up against his mouth. His Mistress was implacable. “Open up, slut-boy. It’s time for you to learn how to suck my d**k. You never know when you might be confronted with a real one.” Sam cringed, but of course he had no other options. After a brief hesitation he opened his lips, and with a firm forward thrust of her hips, his Mistress slid it in.

She gripped him by the head and started pumping then, f*****g his hotly flushed face. Burning with humiliation, his gut churning at the spectacle he surely made, Sam accepted that big hard insult with little outward distress. But then Mistress started f*****g him harder, pushing right through his mouth and into his throat, gagging him with her insistent rhythm. As her leather-clad crotch began banging his nose, and her big c**k plunged in and out of his esophagus, she resumed holding school.

“That’s right, slut, take my entire big schlong. Relax your throat. The sooner you overcome that gagging, the better – at least for you. I don’t know, I kind of like it… Yes…that’s right…good. Now suck me off like the sweetest little sissy-slut in school. I bet you never thought having your face f****d could be so much fun, did you?”

On and on it went, both the f*****g and the instruction, until at last Mistress seemed provisionally satisfied. “Well, all right then. I’d call step one complete. Now it’s time to see what your other tight little hole can do for me.”

Smoothly she withdrew from Sam’s mouth, leaving him relieved, disappointed, terrified, breathless with anticipation and blackly aroused all at once. Ignoring his incoherent whimpers, Mistress moved around behind him and gripped Sam by his slim, firmly taped hips. Then, with the ease of long practice, she aligned her big, up-jutting eight-inch member with his tightly puckered anus and began pressing her way into him.

Sam struggled helplessly, both inside and out. While his limbs fought to free themselves – and failed – his mind had similar nil success in shirking the awful humiliation and uncontrollable arousal generated by this unprecedented invasion. His own back-bent p***s throbbed urgently, responding automatically as first the head of Mistress’ c**k and then inch after inch of it’s thick, vein-wrapped shaft split his most secret center wide open and forced its hard, cylindrical way up into him.

He heard himself sobbing, he faintly detected his Mistress’ heavy, excited breathing, but nearly all of his awareness remained focused on the inextricable pain, shame and arousal of having his rectum violated for the very first time. When at last his Mistress had her entire big length buried inside him, she began grinding her hips, waggling her enormous boner around in the virgin-tight territory she’d just so deliciously claimed. While Sam groaned and wept and tried to deny the urgent pulsing of his own c**k, she once again began f*****g and instructing him.

“There, you see? You’ve got a big hard c**k in your ass and you’re still alive. That little sissy-hole of yours stretches out real nice. You can take a much bigger one than this, and soon you will. But this is good enough for now. This is where I teach you all about f*****g from the ladies’ point of view. Then we’ll see how eager you are to dish it out!” Already she’d begun pumping, working her matchless hips and sliding her big erect p***s slowly in and out of him, but now she picked up the pace. She began slamming herself into Sam, responding to his agonized whimpers by f*****g him ever harder and renewing her ever sterner warnings.

“Keep quiet, Slut-boy! Discipline, now! Show me you can take a vicious butt-f*****g and still remain silent! Anything more than grunts and groans of pain and pleasure could damn us both and cost you your life!”

Almost as if on cue, a commotion began growing in the hallway just outside the room. The crashing, banging and tromping of the football team coming in from practice reverberated up the hallway, as all of Sam’s friends, coaches and teammates began to pass by less than a dozen meters from where he was presently being brutally corn-holed. If anything, Mistress’ manic rhythm only increased, hammering away at both Sam’s virgin rectum and his pathetic preconceptions, until finally his combined pain, arousal and abject humiliation began to peak right along with the bedlam outside.

Grunts and groans of pain and pleasure indeed! Since these were all that were allowed him, Sam wallowed in them, groveling in an abysm of raped mortification as his ass was violently used in an almost-public fashion. At last the entire football team moved past, promising a bit of relief from his fear of discovery. But then to his horror, Sam heard the junior varsity cheerleaders following them. The tinkling voices of the freshman and sophomore girls, nearly all of them familiar to him, filled the hallway with giggles and chatter. Likewise they filled Sam with as much shamefully hot dread as that pistoning p***s continued to pound ignominious agony into his ass. Sam’s own back-bent hard-on throbbed against the back of the chair; his head swam and his entire groin tingled with arousal. Then to his horror the giggling voices stopped just outside the door.

The knob rattled, and finding it locked, the girls knocked on the glass, and called out loudly in their innocent little voices.

“Ms Phillips? Are you there? We need the assignment for Monday!”

Super-b***h only responded by picking up her pace yet again, now hammering herself into her slut-boy’s up-thrust ass with a speed, power, and zealous abandon that was nothing if not contagious. Utterly surpassed, Sam’s thick, conflicting stew of emotions boiled over at last. As the girls knocked and called out once again, he suddenly felt his captive erection spasm. Then suddenly he was shooting out jet after hot, wet jet of spunky-smelling semen.

Just barely did he clamp off his cry of ashamed release, and ever harder did his Mistress pound away at him with her own stiff erection. But at last the cheerleaders gave up and moved off, and Mistress’ jackhammer pace slowed and then stopped entirely.

She slid from Sam’s horribly aching ass, and snickered quietly down at him.

“Well, that was well done indeed, Slut-boy. I think you’re finally starting to learn some true discipline here. However, that unauthorized ejaculation at the end is something we’ll definitely have to work on. I’ll want you to be at my house, tonight, at seven o’clock. There we’ll resume your lessons in a more controlled, appropriate setting, where I can spell out the course of your training in more detail.”

Mistress was removing her dildo, and even slipping back into her skirt and blouse. Back into the drawer went the strap-on. Then as Mistress was cutting the tape and unlocking the handcuffs, she gave her Slut-boy his first assignment.

“I want you to leave here now, go out and buy yourself some nice silk panties and a pretty, lacy brassiere with size D cups. You will wear these under your outer clothes when you arrive at my house tonight, Slut-boy. Is that understood?”

Sam had to clear his throat twice before he was able to respond. Then he did so humbly, with his eyes still cast firmly on the ground. “Yes ma’am.”

“When we are in training, Slut-boy, you are always to address me as ‘Mistress’.”

“I am sorry, Mistress. I understand your orders, Mistress, and I will obey them.”

“Good. Now get dressed and get out of here, Slut-boy. I’ll see you later tonight.”

“Yes, Mistress!”

Slut-boy slipped quickly, painfully into his clothes. Then he fled.

Mistress was gratified to see that he was moving quite gingerly as he did so.

Melissa’s Alaska

Melissa’s been my best friend for over a decade, despite the fact that she’s considerably younger than I am.

We were roommates for a few years before she got married, and have remained extraordinarily close ever since – despite the disapproval of her asshole husband. The truth is she almost certainly would have married me instead of him, were it not for the unfortunate fact of my quadriplegia.

A spinal cord injury in my early twenties has left me only able to move my head, neck, shoulders and arms.

I have good sensation throughout my body, can even feel a fly land on my toe. Muscle spasms aside, I just can’t move below mid-chest or so. Most unfortunately, I’m also impotent.

Oh, I can still sprout an erection of amazing duration. I just can’t achieve ejaculation or orgasm with it. Believe me: I’ve tried, pulling my pud for hours at a time, with only maddening frustration as a result. For the past five years I’ve even stopped trying. So much sensation without consummation has predictably transmogrified into a torment in itself.

Really, how much pointless stimulation can anyone take? I’m better off trying to forget such things, just as I’ve put walking, running, and playing football, hockey, and soccer, going fishing, camping, and all the other things I used to love so much out of mind. Instead I now get my s*x vicariously, writing out my increasingly kinky fantasies in an endless series of dirty stories and collecting vast amounts of pictures and videos, some of Playboy models, but mostly featuring all kinds of bondage, discipline, anal play, torment and humiliation – all things I can really relate to in my severely proscribed existence.

Anyhow, back to the lovely Melissa.

She knows full well that I am both deeply devoted to and madly in love with her, just as I know full well that I am wholly unworthy of her. In addition to being crippled, I have a bit of a pot belly, which is accentuated by a shamefully shallow chest. Meanwhile she is of course absolutely gorgeous.

Five foot-eleven, she is tall and slender and yet everywhere perfectly curved, with high, firm, delectably symmetrical little breasts. Her clear white skin is utterly flawless, with large brown eyes in an honest, open, beautiful face. Best of all, in my opinion, her gleaming brown hair parts right down the middle and falls perfectly straight all the way down her back to well past her shapely waist.

It’s no wonder she was able to land such a ridiculously rich husband at the tender age of eighteen. And it’s a credit to her personality and integrity that she and I have remained confidantes and secret soul mates all these years since, despite Rupert’s endless attempts to isolate her. Then again, with no close family, to whom else could she go to b***h about him all the time?

He’s a classic control freak, a pathologically domineering tyrant, and apparently a big disappointment in bed as well. For over eight years I’ve listened to Melissa’s endless frustrations and complaints, and grieved inside that my crippled condition has rendered me unworthy of her myself. Or so I’d always believed, until the astounding phone call I just received.

“Hello?”

“Jon?”

“Hi punkin pie!”

“Hi yourself, cutie-poo. Guess what? I’ve got some amazing news for you. Are you sitting down?”

“Ha ha.”

“Oh, darling, you know I’m only teasing!”

“Of course!”

“Well listen to this then: I am getting divorced!”

My gasp must have been audible. But tactfully she ignored it.