Page 34 of Pain Play

“Oh no, that won’t do. You need to watch them while they watch you.”

Dammit. He obeyed Phil’s command, trying to ignore the flush of heat under his skin.

“Very good. Now we can continue.”

He met Marco’s gaze and it not only eased some of his embarrassment, but made him happy to see how much his friend appeared to be enjoying himself.I’m pleasing my Master and pleasing Marco. The shame dissipated and began to transform into arousal.

Phil squeezed a generous amount of slick on his fingers before adding more to Terry’s exposed asshole. He teased the wrinkled skin guarding his entrance with the liquid then dipped two fingers past his rim, fucking his passage with short thrusts. He gradually pressed deeper, in and out, farther, until he nudged Terry’s gland.

Terry gripped the backs of his thighs as Phil massaged the nub inside him. His need to be filled grew the more Phil taunted him with his skilled fingers. Phil removed the two digits he’d already breached him with then added a third. Terry threw back his head as he arched, the burn so good, so satisfying. Phil twisted his hand as he plunged into him repeatedly, opening his fingers as wide as Terry’s rim would allow.

“Give me your hand, Terry. The one opposite from me.”

Terry did as he was told, and Phil added some lube to Terry’s first two fingers.

“Slide them in next to mine.”

An ‘are you fucking kidding me’ almost flew from his mouth, but he bit it back. Instead, he reached between his legs, doing his best not to jostle his aching balls, then prodded at his heated rim that was stretched so tightly around Phil’s thick fingers.

“Uh, Master? I don’t think I can…” He frowned, uncertain over what it was he wanted to say or do.

“You need to be specific. There is no ‘can’t’. You either obey or safeword.”

Right. He knew that. But it took on a different sheen when he was doing it in front of others, especially ones he cared about.That’s what it is. I don’t want to be a failure in front of them.He almost laughed out loud at the realization.I want them to be proud of me too.

“Master, may I please have some more lube?”

“Yes, you may.”

Phil added more liquid on his fingers, then squeezed additional lube onto his hole. Terry took his time, determined to succeed while still being careful not to hurt himself. He wouldn’t force it, but he was fairly sure he could do it. He started with a single digit by nestling it between two of Phil’s fingers that were already stuffed inside him. As Phil pumped them in and out of his passage, he was able to gradually breach the ring of muscle until it slipped inside him with all of Phil’s fingers.

Terry sucked in a strangled cry, the combination of their fingers fucking him in tandem teetering him on the edge of what little control he had left. A ball of tingling energy gathered low in his spine, and as if Phil knew what was about to happen, he gripped the base of Terry’s shaft, squeezing hard. Phil stopped moving and trapped Terry’s finger to keep him still.

“Breathe through it, baby. Just rest for a moment.”

Sweat trickled down Terry’s neck as he fought against his impending orgasm. After a couple minutes, he felt as though he’d averted his crisis.

“Are you ready to continue?”

Terry nodded shakily. “Yeah. I mean, yes Master. I’m ready.”

Phil loosened his grip on Terry’s cock then added more lube to Terry’s stretched hole. “I want you to insert the other one. Just for a few strokes, then we’ll take them out. After that, we’re allgoing to sit and watch you fuck yourself with that big dildo until you come.”

If he keeps talking like that, it won’t be a very long show.

Terry concentrated on the task at hand. They moved their fingers together again, but this time, Terry used his middle one to tease his opening that already seemed to have been stretched as far as it would go. He used the same move as he had before by nestling it with the others as they pulled out. He let out a cry as his second finger plunged in with the rest, his rim stinging as it loosened up even more to make room so it accommodate his and Phil’s fingers.

Phil remained true to his word and after no more than three or four thrusts, he pulled all the way out. Terry did the same, his body mourning the loss of being filled. Before he left his side, Phil kissed him, a silent reassurance that he was doing well. It gave him the strength to keep going.

“Master, may I please rest my legs before I continue?”

“You may.” Phil set the dildo down next to him. “You can get this ready in the meantime.”

Terry’s hand shook as he picked up the toy Phil had laid on the cushion before he joined their friends on the sofa. The container of lube was next to it and Terry didn’t hesitate to add plenty of slick to the silicone object. Phil had made his way to the other couch and taken a seat next to Gerard.

Phil stared at him, gazing into Terry’s eyes before he switched his attention to the large phallus Terry held in his hand. Phil glanced back up, licking his lips. “Continue. Don’t hold back. Show us everything, how much your body begs for it. Let us hear what being fucked by that big fake dick does to you.”

“Yes, Master. Whatever makes you happy.” Terry’s voice had barely been above a whisper.