Mrs. Simmons

She shushes me again, before commenting dryly, "Steady. Don't move. I'm not done with you yet."

God, her voice. What a voice. That combination of arrogance and firmness in her tone makes my head spin.

Then I feel a slight pressure, and her long finger has trespassed to the second knuckle. I exhale, shamelessly.

"I have hoped you would put up more of a fight, Bobbie. But then again, your willingness to accept my lead so easily, makes me think of doing things even naughtier. And I like that. You're going to be a fine pet, Bobbie."

I'm lost. Lost badly. There is no resistance left. Even though it feels wrong, I embrace my willingness to surrender with all my might. Strangely, I've never felt more alive. As if my previous existence has been an error, a mistake. Suddenly it makes sense, why it has taken me so long to reach orgasm, when I have fucked Florence, and why those ejaculations have never felt as good as anything, as detested Mrs. Simmons has so far done to me.

Before I know what is happening, her finger is gone, and has been replace by the greasy cold tip of that shaming butt plug. This object is far thicker than her finger. It will never fit in. Never! Even though she keeps a steady pressure on my sphincter, I'm certain, it will never pass it.

I'm wrong of course.

She increases the pressure. And I'm fighting it. I clench.

"That's more like it, Bobbie. Yes, fight that phallic evil. The more you fight it, the more powerful your orgasm will be."

"But it's going to be painful."

"Of course, that's part of the fun."

"I don't want any damage."

"Silly! There won't be any damage, except maybe your psyche. Your mind will give you a hard time comprehending, once you've peaked, and your arousal is back to normal. But other than that, you'll be fine."

While I'm fighting that plug, the tip of my swollen cock begins to drip its excitement. The sudden tingling feeling vibrating through my well lubricated urethra is so intense, I try to ease the maddening sensation with another dry hump. Suddenly I feel the coolness of her waiting fingers gracing my glans. She has formed an artificial ring of friction with her thumb and index finger, inviting me to pass through. When my sexually intoxicated brain computes what that means, all hell breaks loose. I've reached erogenous singularity. Like a prized bull brought in for artificial insemination, I have one singular purpose, to expel my seed into whatever direction my cock head feels friction.

When I try to hump her fingers, she teases me and puts them out of reach. Frustrated, I move back into position and she promptly increases the pressure on my reluctant sphincter.

"Here is the deal, Bobbie. I'll let you fuck my fingers, but you'll relax your anus in return. Just think of it as being constipated. It's going to be the same level of discomfort, when I force that plug through your sphincter. Once this is accomplished, it will blow your last remaining fuse, and you'll release — willing or unwilling, that's for you to contemplate about afterwards -- and make a mess again."

The playful naughtiness in her tone reveals, just how much she enjoys tormenting me. She loves to talk dirty.

Then she adds, and for the first time ever, I sense admiration in her voice, when she speaks, "You've got one hell of a body, Bobbie. And your beautiful cock, well, ...," she is fighting not to laugh, "... certainly has gotten my attention."

Her favorable words feel good and I relax. But the pressure on my anus is still too much, far too much I'm able to handle without pain. Until, ..., I sense the coolness of her fingers interacting with my bursting glans. It instantly evens out the pain. She lets me fuck her fingers for a while. She even squeezes my tip intermittently like excited pussy muscles might do. As long as my cock gets friction on her offering, my mind goes blank with a singular purpose, relieve. Ever so slightly we begin a steady rhythm. I penetrate her fingers — an erotic perception so intense, I almost pass out -- while she gradually increases the pressure on my backdoor.

My copulating movements become ever more urgent, when I sense her fingers loosening up, deviously reducing the friction I so desperately crave for. She increases the pressure on my anus and miraculously I relax my sphincter muscles long enough for the plug to finally pass through. I hardly realize the brief spike in pain.

The sensation is incredible. I've never experienced such an all-encompassing level of fullness. But it feels alien, and I'm overwhelmed by a profound level of helplessness and utmost shame. It makes my vision blur. She has really done it. She has violated asshole. She has me sissified.

Yet before those hammering thoughts can do any more damage to my psyche, the enormous pressure the damn plug is putting on my prostate, speedily quadruples the itchy tickling in my cock and causes me to buckle spasmodically. Through a layer of intense fogginess, I hear Mrs. Simmons commenting dryly, while she taps my back encouragingly, "Fight it all you what, Bobbie. You've given up control over your body long ago. It's me, who's in charge of your arousal, and it's me who's telling you when to emit your seed. From now on, it's going to be this way."

I groan, frustrated, even annoyed, but I'm helpless to counter the enormous built-up of pressure in my ass and cock. Mrs. Simmons slowly puts that shaming glass of hers over my cock. My cock twitches when I feel its cooler surface. Buckling once more, I try to fuck the new confinement, to no avail.

She spanks my exposed behind hard, four times in quick succession.

"Emit!"

And within a second, I helplessly spurt my seed.

It is a strange feeling. Different, not bad altogether. Equally intense, but passive. I have nothing to contribute. My cock touches the cold surface of the glass intermittently, while my balls are busy releasing my virility. That strangest of all orgasms seems to never end. The slow but steady dribble seemingly goes on for an eternity, while that joyful orgasm continues. And when I lastly sense the unnatural euphoria ebbing, Mrs. Simmons, once more, viciously begins slapping my ass, sneering, "We're not done yet. I want all that nasty come of yours drained. I want you flaccid, smallish and manageable!"

To my surprise, her spanking makes me explode once more. I even arch back, try to rise, but ultimately fail.

"Aaaarhg!!"

The firework of sensory overload in my cock peaks, and I explode into the glass she keeps holding over my ejaculating tip one last time, before I collapsed, broken. There is absolutely no strength in me left.

She quickly takes away the glass, before my spent body dissolves to the cold classroom floor. I'm panting heavily and am totally exhausted. Finally, my erection is gone, and I begin to notice the intense pressure in my ass. It quickly becomes extremely uncomfortable. Yet before I have time to complain, she removes the plug in one swift movement, relieving me of any further discomfort.

"Turn on your back."

Totally frazzled, I do. Slowly. Still in trance. There is not a grain of energy left in me. She leans in slowly, intimately close to my exhausted face, smiling. Then she whispers encouragingly, "Open your mouth, Bobbie."

I think she is going to kiss me and close my eyes. Instead, she once again feeds me my own come. I'm too exhausted to fight her any longer, and obediently swallow the obscene amount of semen. It's a lot. She has drained me completely. She has accomplished her intention. I'm smallish and manageable. There is no strength left in my cock. It has shriveled completely.

I'm tired, dazed, and have entered unchartered emotional territory. I keep my eyes closed. As if it would help to shut out, what just has happened, and prevent my reemerging principles to start asking questions.

I feel her fiddling with my limp cock. Out of nowhere she has produced the odd-looking device — a cock cage -- as I'm about to realize in a moment, has secured it around my manhood and locked it immovably. Within the timeframe of minutes, Mrs. Simmons has managed to grant me the most spectacular orgasm of my young life, only to completely emasculate me afterwards. The emotional turmoil I feel, when I look at the odd device, now confining my limp cock, is not pleasant. Yet, Mrs. Simmons smiles.

"See, Bobbie. Just as I've predicted. That was something, wasn't it?"

I have no idea what to say. Even if I had the will to do so.

"Get up. Get dressed. And get out of here. Oh, and by the way, I'll keep your trunks."

She stands up, rearranges her rumpled dress, picks up her bag — she has obviously cleaned up her stuff, while I have been staring at the stupid lecture room wall -- and graciously walks towards the door and unlocks it. Before she opens it, she turns around, smiling, "Forget about that footage, Robert. But don't be so careless in the future. Those moments of leisure could have ruined it. Go home now and relax. You've earned it."

And then, she is gone.

For a moment.

She reopens the classroom door, and sticks her head in.

"If you want that cage to come off, or to get your trunks back, you'll have to see me at my place tomorrow, or, and in this case, you won't see me again, wait until I send you the key in about a week. Remember, you've committed a crime, and you need to be punished. But it is up to you, how that punishment is going to be delivered."

This time, she is gone for real.