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Captive demiboy -- by Shadowjack

“Please, Sir,” Shayn whined, “please please please pleeeeease let me cum…”

I ignored his pitiful begging and continued pumping the dildo in and out of his ass. I’d been pumping it slow for the past five minutes, so when I suddenly began jamming it in hard and fast, I got another desperate squeal out of him. That made me smile.
We’d been going on like this for well over an hour now. Shayn was on his knees on the bed, his wrists cuffed to the overhead canopy. He was effectively helpless, and I’d been dominating his tender bottom-hole with this huge black dildo for so long he was almost incoherent. It really was a monster of a dildo. The shaft of the thing was fourteen inches long, plus a comfortable handle on the end, and it was thick, almost as thick as Shayn’s wrist. But the head of the thing was its most wicked feature, an extra-large knob that was frightening to behold. It had taken a while to get it into him, but once in, it had kept him entertained every moment.
I’d driven him to tears after the first ten minutes, driving the monster all the way up into his squirming bowels again and again. When I pumped it fast he shuddered and shook and wailed helplessly, and when I pumped it slow he sobbed and begged. At first he begged me to take it out. Then he begged me not to fuck him so hard, or so deep, or so fast. Finally, for the past fifteen minutes, he’d been begging me to let him cum. But for all the crying and begging, he had never uttered his safeword.
I loved my submissive little demiboy. He was the perfect partner for me. I could be as mean as I wanted to him, and he took it without ever tapping out. I could make him yelp, shriek, squeal and even cry, and he never let on that he loved it until it was over.
I hammered him hard and fast, burying the entire fourteen inches in his bouncing ass with each stroke, and he squealed and sobbed in delicious suffering. I kept it up for a full three minutes before taking it back down to long, deep, slow strokes. Shayn continued to sob, and when he was able to form words again, he begged me once more to please let him cum.
His cock was hard again, throbbing visibly, a thin ribbon of precum stretching to the bedspread. I stroked the excited organ teasingly with my fingers, and he groaned uncontrollably. I had been stroking it intermittently the whole time, keeping it teased up, never letting it go all the way soft.
“What will you do for me if I let you cum, little demiboy?” I teased.
“Anything…” he gasped.
“Will you suck my cock until it squirts?”
“Yes!” he said eagerly. “Yes Sir, yes! Please let me suck it!”
“Will you take it down your throat so I can cum in your belly?”
He hesitated for only a moment. “Yes Sir!” We both knew he had trouble taking my cock down his throat, but he was always willing to keep trying.
I stroked his hypersensitive cock steadily, feeling it swell in my fingers. I continued to pump his ass with the dildo, slowly now. “Will you take my cock down your throat down at the Rawhide, so all the guys can watch?”
His breath caught as he considered it. Shayn was shy, and just going into the seedy gay bar down the street scared him. The idea of performing in that environment was way out of his comfort zone. “P-please, Sir, don’t make me…”
I removed my hand from his cock and used both hands to plunge the dildo in and out of his ass as hard and fast as I could. Shayn squirmed and squealed desperately, even going so far as to arch his body forward until his hips were almost touching the bedspread, trying to get away from the implacable dildo, but I never even slowed. I kept it up for five full minutes, until I was panting and too tired to keep going. When I stopped, Shayn was sobbing again, but he slowly returned to his original position, on his knees with his ass thrust out for fucking.
I pumped him slowly until the sobbing stopped, then I asked him again. “Will you take my cock down your throat in front of the guys as the Rawhide?”
“Yes Sir,” he whispered, surrendering to my will.
I wanted to kiss him, but instead I took his cock in my hand and began to stroke it steadily, pumping the massive dildo in his ass with the same rhythm. In less than a minute he began to emit excited little cries, rising quickly in scale as he drew closer to climax. His body shook and tensed, and suddenly he was shrieking as his cum exploded from his tormented cock, shooting across the bedspread again and again. I rode it out, pumping hard at his cock and his ass, until the final shudder.
I uncuffed him quickly, and pulled his panting body into my lap so he couldn’t evade my kisses. He didn’t try. After a few minutes, I spoke.
“You won’t have to suck me in front of the guys at the Rawhide. Maybe someday, but not yet. Tonight, it’s just you and me. And my cock, which needs your mouth immediately. You may begin.”
Shayn obediently knelt before me, eying my hard cock and licking his lips. “Um, Sir?”
“Yes, Shayn?”
“Could you, um, take the dildo out of my butt now?”
“No, Shayn. Perhaps after we see how the blowjob goes…”

Shadowjack does art and txt. This piece appeared first on his website.


  1. I'm not fem but that had me instantly so hard. Exactly the sort of experience I utterly desire. I have a macho controlling job by day, but at night I want to be controlled & dominated as the total slut I really am!!

    1. Thanks, cool. LustSpiel is always pleased to cause an erection.


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