The slap came out of thin air. Hard and stinging across my cheek. Again, I was too stunned to react. “I asked a fucking question, Jimbo. It’s not that complicated. Are you going to be a good lay or are you going to fuck me over?”
“I’ll be good,” I muttered.
This time she had me by the prick, her long fingers wrapped nice and tight. “I’ll be a good lay, Jillian,” she made me say. “A nice, righteous piece of ass.”
She smiled, not a look I’d ever seen before on a women’s face. It was a predator’s look. Like a cat, pricking its talons for the first time into a new mouse it is about to torture. “Just remember,” she pointed out. “Whatever happens, you are fucking hard as a rock. Which means you want it. Tell me you want it.”
“I want it,” I told Jillian, though I hadn’t the slightest clue what I was about to receive.
“Take your shorts off. Lay over your desk. Ass up,” she ordered. “And whatever you do—no coming until I say so, or you’ll be one sorry little boy.”
I leaned over the edge, putting my cheek down on the blotter. My nipples rubbed the smooth, cool mahogany. I was completely exposed, my anal cavity and butt cheeks at her complete disposal. My cock, meanwhile, was pushed hard on the underside of the desk. I was terrified of ejaculation, though rationally, I had no clue what she could do to me by way of punishment.
I moaned softly now as she caressed my ass, gently teasing both cheeks. My toes curled into the rug. She waited until I was truly enjoying myself to smack me with her hand. “That’s for hassling me over the phone.”
My buttocks clenched in reply, further tightening my balls.
“And this is for being a man.” She hit me all the harder, sending shooting flames up my backside.
“And this,” she devastated me with what must have been the wooden ruler from off my credenza. “Is just because I fucking can.”
I danced on my toes, thoroughly degraded and miserable. “Jillian,” I pleaded.
“Unless you’d like me to piss on your underwear and gag you with it,” she advised. “I would shut my fucking trap.”
Having no reason to think she was bluffing, I did as I was told. My obedient silence earned me a scruffing of the hair. “Good boy. You may be worth something after all.”
Five more times I endured the cruel device, each time on a different part of my ass. When she was done, Jillian rubbed the welts and told me how red and pretty they were. I was seeing stars, the agony ripping through every nerve ending in my nude body, but when she asked me if I was ready to lie down and be fucked, I cried out “yes” with total abandon.
She shoved a finger up my ass to seal the deal. “Are you going to be a good lay?”
“Yes,” I groaned against the pressure, bucking my ass helplessly. “I will, I swear.”
“You better be,” she said. “Because from here on, I’m taking control of you. I’ll be able to make you do things, Jimbo. Trust me, you won’t want to cross me.”
Jillian stepped back, allowing me to get down on the floor. My ass caught fire all over again as it pressed against the rug. Lying down on my back, I drew an unsteady breath. Jillian was standing right over me, still fully clothed.
“Hands over your head,” she commanded. “Legs spread.”
I obliged, rendering myself even more helpless.
“That’s better,” she approved. “Next time I’ll expect you to assume the position properly on your own.”
She caught the expression on my face. “That’s right,” she laughed. “There will be lots more times. Until I get bored with you. You’re mine, Jim. Isn’t that clear by now?”
I clenched my fists as Jillian touched her toe to the bottom of my cock, lightly rubbing the leather over the vein. I was going to shoot off…
Jillian’s features darkened. “Don’t you dare, you little worm.”
I stifled a scream as she pushed down with the bottom of her shoe, flattening my cock against my belly.
“It will be the heel next time,” she warned. “Understand?”
“Yes,” I groaned through clenched teeth.
“Let’s get you in the habit of saying “Yes, Mistress,” shall we?”
And so it began…my official roller coaster ride into slavery under the cruel hand of Mistress Jillian. Having secured my official submission, she took off her clothes for me, introducing me to the visual thrills of her near perfect body.
“You’ll touch me only as I direct,” she laid out the future course of our relationship. “You’ll see only what I want, and pretty much that will be just to torture you. Sometimes I’ll make you masturbate and not lay a hand on me. I might make you watch while my boyfriend screws me, too.”
This was the first I’d even known of her having a significant other. I’d learn soon enough what it was like to perform in front of a man, or else to sit by and watch another man enjoying the woman I lusted after night and day. I would even come to know the feeling of being taken by a man, as if I myself were a woman. For now, however, it was all about being taken by her—my body mounted for Jillian’s pleasure.
That pleasure, I quickly discovered, was in direct proportion to my own pain. To get her pussy dripping, she slapped my dick back and forth while straddling me, just below the cock. “Pinch your nipples,” she ordered, fascinated by the look of agony on my face.
I squeezed the tiny nubs best I could. She grabbed my balls, inducing me to do it harder. My eyes were tearing even as I lifted my hips off the floor, craving more.
“Beg for it,” she hissed.