Chastity Report Card

Hired Help pt.3

Such a shame but stop moaning. Your boring me!

The Enchantress: A Most Cruel Baron (part 1)

The cruel mistress had forced the hero into the form fitting, double sealed cocoon. She smirked down at his struggling form. She turned to the enchantress, who was leaning in the corner shaking her head.

Baroness: He came at my house, with the notion that he would defeat me and free my slaves… So I’ve made him into one instead. Will you be interfering?

Enchantress: If he were foolish enough to be defeated by you he deserves it. I won’t interrupt your game.

The baroness smirked and looked down at the cocooned hero.

Baroness: You weren’t as powerful as the rumors made you out to be, heroic little boy. I was able to overpower you with just a zap of my lightning baton… It’s such a mighty baton, isn’t it?

Giggling, she bent down to feel the hero’s crotch. He squirmed. She had sealed him nude, an impression of his erection outlined against the rubber. She smirked and placed her baton, powered off mercifully, alongside his cock. It had a solid two inches over the hero’s “baton.”

Baroness: My my, unimpressive in other ways. I believe mine is far worthier of the tile “hero” than yours. Aren’t heroes supposed to wield mighty weapons, hero?

As she said this the enchantress shook her head and walked toward the two. She nudged the baroness to the side and whispered in the hero’s ear.

Enchantress: Hello, dear. Just letting you know that I am here as well.. I’ll be protecting you from anything too dangerous… Does that relieve you? Or are you even more terrified than before…

The hero’s squirming and struggling immediately heightened… His erection immediately grew, stretching its rubber trappings. The baroness’s eyes widened as it grew to nine… almost ten inches, surpassing the length of the baton by half an inch.

The enchantress smirked at the baroness, who pouted.

*** *** ***

The baroness forced the bound hero’s body to the ceiling, bound with a chain holding his ankles, his knees, and one against his shoulders. He hung two meters in the air, his back curved back so that his crotch was dangling a foot below the mistress’s head.

She felt the rubber bound crotch with her hands, gently at first. Then she pressed the hard end of her whip against the outline of his cock to let him know her sadistic plan.

Baroness: Real leather. The knob at the end isn’t metal, just some bunched up wool. Your body is covered with relatively thick rubber, which will shield you only a bit. Make no mistake, it’ll still hurt more than you could possibly imagine.

She looked back at the enchantress.

Baroness: … You really won’t object to this? I’m going to be destroying your boyfriend’s precious cock.

Enchantress: Do your worst.

Baroness: It’ll be slow… I’ll make him suffer for a long time… I once captured a robber and whipped him for a whole day. Even hunger and thirst couldn’t stop me.

Enchantress: Your sadism knows no bounds, Baroness. Impressive. Nevertheless, feel free.

Baroness: Truly, you are a most awful lover.

Enchantress: You simply don’t understand him as I do.

The baroness uncoiled her whip. It was thin, like thread.

Baroness: You underestimate my whipping arm, enchantress.

She swung her whip at the hero’s crotch. It struck him with a crack.

Disappointingly, the hero gave a low muffled wince. Not the shrill scream of pain the baroness expected.

Enchantress: Hmph. Even if he weren’t shielded in tight rubber the hero would barely feel such a weak blow.

Incensed by these words the cruel baroness swung harder with each subsequent whip. She expertly hit her target each time, the hero’s poor tortured genitals. Even simply watching would make anyone who was born with a pair of balls themselves beg for mercy on the hero’s behalf.

Except for the lack of cries or evidence of pain. In fact, the hero was instead moaning, and whimpering. He begged for her to stop and for mercy, yes… But not from pain.

Baroness: My God… he’s about to cum… Is he a masochist.

Enchantress: As I said before, your weak little whip is nothing against his bulwark of defense. His pain tolerance is inhuman, beyond even the level of some of the mightiest ogres. All you’re doing is bullying his poor cock… Essentially, you’ve just been jerking him off. Well, not that I’d stop you even if you could hurt him.

The enchantress glanced at the hero, frowning. Her precious hero had many weaknesses. But he had none at all against pain. She had never uncovered the mystery of why…

Baroness: Absurd!

She gave one final lash at the hero’s cock.

The rubber split open. His long, erect cock slid through the slit. It was trembling…

Baroness: Oh my!

The baroness flinched, covering her face as though expecting him to cum right onto her body… When it became clear he wasn’t going to… not yet… she took a closer look…

Baroness: O-oh…

She looked at it with some reluctant admiration… She had spent the last few minutes attacking it, and yet it was not bruised or cut. It was simply red from the pressure of being sealed up for so long, huge from arousal, and shivering on the edge of eruption from the erotic abuse…

The words “strength” and “beautiful” being associated with a penis is laughable. Ridiculous. And yet those bizarre and childish thoughts appeared in the baroness’s head…

Despite herself she wanted to touch it, even if it made him cum all over her. She would risk it…

She felt the cock’s skin with her finger tips, stroking it. The hero’s muffled screams grew louder. It felt hard, nicely warm… Being a cruel, despicable human being, each time before that the baroness had felt the penises of her playthings they were whipped and pathetic little things that she had abused. She would masturbate to her sex toys’ destruction and her dominance and victories over them, never actually allowing them to orgasm…

She gave the hero’s cock three soft tugs. The hero screamed in ecstasy and the baroness knew it was coming. She was braced for it, however unpleasant it might be. In fact, some dark secret part of her soul wanted it. She wanted to see if there was pleasure in making a man cum…

Enchantress: Whoopsie!

With a snap of the fingers the hero’s cock was sealed up back into the rubber suit, which repaired itself. The hero’s hips bucked against the rubber bindings and he screamed and moaned. To the baroness’s great dismay, she realized he was orgasming inside the suit. She could only see his orgasm through the opaque, tight rubber outlining his shapely cock. It twitched and twitched for a solid twenty seconds! And it grew smaller and smaller.

She watched it with wonder. What was this feeling, knowing she had made him cum? She had always seen allowing a slave an orgasm as making a concession, giving mercy. But this didn’t feel like that at all. She felt a warm tingling in her loins that she couldn’t explain…

Enchantress: That was close, baroness. You nearly got your slave’s nasty gunk all over you. Luckily I was here.

The baroness looked at the enchantress. She was looking down at her, smirking. Whatever the baroness was feeling right now, the enchantress obviously knew.

Humiliated the baroness stormed away to stew in her thoughts in another room.

The enchantress smiled up at the bound hero.

Enchantress: Quite a predicament you’ve fallen into. I wonder how or if you’ll ever escape this one… 

She chuckled to herself as she reached up and began squeezing the poor hero’s post-orgasm, tender and sensitive rubber bulge…

Suspension Sunday Funday!

i want to use my strap to cum on a boy’s chest, i just know any pretty baby boy of mine would love it.

I dream about it constantly!