In terms of the first time, not long!

Ultraboy whimpered and arched his back as his cock spurted out its first load, the thick load being sucked into the awaiting vat, Pleasure groaned as he felt Ultraboy's asshole clamping down on him, the exquisite feeling of pressure on his thrusting 8" invader. Ultraboy gasped for air as he tried to recover from his rather quick orgasm.

Once he'd gained coherence, Ultraboy looked up at Pleasure who smiled down at him, Ultraboy's resistance, which was hanging by a thread, broke when Pleasure leant down and softly kissed the hero on the lips, rubbing his tongue on Ultraboy's lips, seeking entry. That was the straw that broke the camels back, so to speak, as Ultraboy opened his mouth and started kissing Pleasure back.

Pleasure smiled as he kissed Ultraboy, pleased with his prey's submission, whilst maintaining a steady rhythm as he fucked the young hero, waiting for the Viagra to kick in, the vacuum pump helping as it sucked Ultraboy's cock like an experienced cocksucker, within seconds Ultraboy could feel his cock stiffening again. Pleasure smiled as he broke the kiss.

"Ultraboy, who do you belong to?"

"Y-You, Pleasure, p-please, fuck me Master!"