“Fuck. Oh fuck. Please, Taylor,” Simon begged, a sheen of sweat clinging to his skin. His bottom lip was swollen from being pulled between his teeth. I smirked and pressed a third finger into him, stretching him for whatever I wanted to use on him next.
“Are you going to come?” I asked, tapping his prostate with my fingers while simultaneously turning the vibrator up a notch and holding it against the little spot under the head of his cock that always drove him wild. “You can come whenever you want, baby. I want to watch you fill your panties with cum.”
“Shit. Fuuck, I’m gonna… Taylor!” Simon came with a broken cry, his cock spurting thick cum onto his stomach and soaking the top of his panties.
“Good boy,” I said, gently removing my fingers and flicking the vibrator off, throwing it onto the bed. Simon’s breath was coming in ragged pants, and I leant up and kissed him softly.
“Holy shit, that was amazing.”
“I’m glad.” I chuckled at the incredulous expression on his face as if Simon was still processing what had happened. “But I’m not done yet.”
“Seriously?”
“I don’t break my promises.” I meant it. I never broke promises, which was why I hardly ever made them. But once I’d committed to something, I didn’t stop unless I had to. I’d told Simon I was going to make him come over and over until he was spent, and I meant it.
Plus, it would be fun for me too, so it was a win-win situation.
I captured his lips in another deep kiss, my tongue pushing into his mouth, and Simon moaned softly. I trailed kisses down his jaw and neck before working down his chest, diverting quickly to tease his nipples with my tongue. When I reached the puddle of cum on his stomach, I locked eyes with Simon as I began to lick it off his skin.
“Oh God, you’re gonna kill me,” Simon said, throwing his head back onto his pillow in the most dramatic way possible.
“No, I’m not. Stop being so dramatic.”
“You’re ruining my fun.” He stuck his tongue out at me and then gasped as I sucked a mark into his hip.
“If you’re not careful, I’ll ruin something else.”
“You wouldn’t!” Simon’s eyes went wide with indignation, and I couldn’t stop myself from laughing. “You laugh, but I’ve had ruined orgasms before, mostly by accident, and they’re fucking awful.”
“Don’t worry. I’m not that mean,” I said, sitting back on my knees between his thighs and looking at the line of toys again, wondering where to go next. “Are you ready for more?”
Simon nodded and whimpered as I traced my finger over the outline of his soft cock through the wet material that clung to it. “Use your words, Simon.”
“P-please,” he said. “Please, Taylor.”
“So good for me.” I reached over and pulled the Fleshjack, glass dildo, and lube towards me. “You don’t use this often, do you?” I asked, holding up the Fleshjack for him to see. Simon obviously wasn’t a fan of cheap toys, so it was well made and seemed to be from a popular line of anal Fleshjacks that used gay porn stars as their models. I was half tempted to ask him if I could try it since it looked pretty good, and when I pressed my finger into it, I could feel all sorts of ridges and bumps lining the inside. I knew they’d feel amazing against my cock.
“No.” Simon shook his head. “I, um, I prefer to use dildos and my coordination isn’t good enough to use both at once.”
“Well,” I said, a devious smile curling my lips. “Today is your lucky day.”
I carefully tugged his panties down, tucking them under his balls before leaning down to take him in my mouth again. I’d always loved it when guys got hard in my mouth, and it only took a few deeps sucks and my tongue flicking over the head and dipping into his slit for Simon’s cock to harden. He whined as I released his wet cock, pressing kisses down his thick shaft and teasing his balls, sucking each one gently into my mouth.
Reaching for the lube, I added more to my fingers before slipping them back into his panties to find his hole. I pushed two into him, my own cock throbbing as Simon moaned. I’d managed to ignore my aching dick so far, but the sounds Simon was making were driving me wild. My brain was seriously debating curtailing my toy plan so I could fuck him instead.
I shook my head, clearing my thoughts as I grabbed the Fleshjack again and pushed the tight opening onto Simon’s dick. I’d already spread lube onto the soft silicone, and Simon gasped as his cock breached it.
“Fuck, that looks so sexy,” I groaned as I pushed the Fleshjack down onto Simon’s shaft. Lifting it slowly, I teased him with the slick tightness of the toy, making him gasp and moan. When he tried to buck his hips up, chasing the sensation, I gave a low growl and told him to keep still. As I lowered it again, I slid another finger into his ass, stretching him wide again.
“Oh God,” Simon cried, his head thrown back as his body was assaulted with sensations. “Shit, that feels so good.”
“It’s going to get better.” Carefully easing my fingers out of him, I reached for the glass dildo, sliding it into his needy hole as I jacked his cock with the Fleshjack. Simon moaned as the curved end of the dildo tagged his prostate. I began fucking him with both toys together, trying to get a slow rhythm going so I could drive him wild.
Trying to get both my hands to coordinate was trickier than I’d imagined, so it took me a few minutes to get it right. Luckily, Simon seemed to take all the false starts as teasing. Desperate pleas poured
