Jesse's Charming Plan

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I pulled off him, frustrated. "You promised I could suck you off!"

"Suck me, sure. But how can I fuck your arse if I cum in your mouth?"

Disappointment welled up in me, along with that deep, aching need to cum that was going to kill me if he didn't let me.

He sighed. "Okay, fine. But only because I can't say no to those eyes."

The jump of happiness inside me was painfully pathetic. I took him back into my mouth with renewed vigour and he stroked my cock, slicking his thumb over the end, even as my tongue made him groan.

"Oh fuck, Jess, there's not going to be much to teach you about sucking cock. I can see that now."

I kept up my action, and he kept up his, and I felt my orgasm build.

I glanced up at him and he understood. "Okay. I'm ready."

He gripped my hair and my eyes rolled back in my head at that touch. He grunted as he fucked my mouth, somehow knowing how fucking erotic it was to me, him shoving in hard and fast while he fucked my cock with his hand.

I let out a growl as I came, exploding across his hand, his naked legs, and splashing against my own belly as I twitched in his hand.

"Fuck, fuck, Jesse, what you do to me!"

He thrust his hips up and pulled me down onto his cock, driving himself in deep so that my nose was pressed against his hard body, and came, exploding into my throat with hot, thick jets of pure erotic accomplishment.

I kept swallowing until I felt him growing soft in my mouth, and finally, reluctantly, released him.

He slackened the grip in my hair and stroked his fingers against my scalp instead.

"Jesus, Jesse. I wasn't going to let you do that. But you... you could bring the world to its knees with that mouth of yours."

He pulled me towards him, back into his arms, and I shuddered against him.

"What's wrong?" he asked.

"I want more," I said, my voice choked with hunger. The butt plug in my arse was all I could think about now. Even though I'd just cum, I knew it wouldn't be long before I was hard again.

"You are going to be exhausting," he said.

I grinned.

"No, don't look so pleased with yourself." His voice was a growl, but he wasn't angry. He eyed me. "You know how to give a massage?"

"Yeah."

He rolled on to his stomach and I straddled him, sitting back against his arse. His muscular buttocks under me made me grind into him a little and he laughed.

"Yeah, that's never going to happen. Get used to that idea now."

I bridled at that. If he thought he was going to top me from now on, he had another thing coming.

I started to massage him, then realised I needed massage oil. I reached for it where I kept it beside the bed and rubbed it into his muscles.

"God, Jess, were you made to give me pleasure, or what?"

I ignored that. After all, I'd cum twice so far, and I was fairly confident he'd make it to three before the night was over.

As I massaged oil into his back, all that tight, bundled muscle under my hands, I thought of what it would feel like to have him in my arse. Would it hurt? Would it be too big?

I was getting hot around the butt plug now—pushing my arse against Will's to stimulate it.

"Fuck Jess, okay, you win!"

He rolled under me and I tumbled sideways. He caught me with a hand around my body and pulled me under him.

"Look at that. Hard in ten minutes. You're a fucking miracle."

I shrugged. Wasn't that normal?

He lowered his head and kissed me, and I felt him growing hard again above me.

He pulled back and I was swallowed by the look in his pale blue eyes. There was hunger... and something else. Triumph. Ownership.

"I think," he said slowly, "For your first time, we'll put you on your hands and knees. It's a shame we don't have a third. I think you'd have loved having a cock in your mouth and your arse at the same time."

Oh GOD, now he'd said it, it was all I could think about.

"Right, stop salivating and get up."

He sat back on his heels while I got onto my hands and knees.

He got behind me and twisted the butt plug, then started back with his tongue, licking around it, dragging his teeth over my buttocks.

He gripped the base and tugged it lightly towards him then let it sink back in, stroking my cock as he did, nuzzling against my spine.

"You ready for me?"

I nodded.

"Okay."

He pulled open the condom packet and rolled it down his length, then slicked liberal quantities of lube over his cock.

He pulled at the butt plug and slowly, slowly eased it out of my arse. After the initial sensation of being stretched, I just wanted to feel something in there again.

He slicked a finger with lube and pushed it inside me. God it felt good. I just wanted more.

He withdrew and slicked his finger with more lube, then pushed his finger back in, opening me up as he spread the lube inside me.

"Now, if at any point it starts to hurt, you tell me, okay?" He stroked fingers across my back as he explored my arse. "And don't fight me. Please, Jess. Not this time."

He took his finger out and with one hand wrapped around my cock, just holding me, pressed his cock against me.

"I'm coming in now. Talk to me if you need to."

He stopped stroking me and put his arm under my hips, holding me steady while he leaned into my arse.

There was a tightness, a feeling of oddness that made me shrink away from him, and then a fullness stretching inside me.

"You okay?" Will asked. He sounded worried.

"Yeah," I said. "It just feels... huge."

"No pain?"

I shook my head. Tightness. Discomfort. But not really pain. Nothing that wasn't worth riding out for how it felt to have him fill me up like that.

"Aren't we both glad you didn't try to fuck my arse?"

One day, Will. One day.

He stroked his fingers lightly over my back, then moved the hand under my hips to close around me, stroking me slowly.

"Relax," he said softly. "Does it feel good to be filled?

"Yeah," I said, almost breathless. I wanted more. More of him inside me.

"Okay, now for the main act." He sounded so pleased with himself.

He pushed a short way and touched something inside me that made my back arch in pleasure, made me harden under his touch.

"Oh, fuck, Jess, yes."

He caught a fistful of my hair and dragged his cock back across that centre of pleasure, and I just wanted him to fuck me. I tried to push against him and he stopped me.

"Not yet, Christ, Jess, you're so fucking eager."

He pushed forward again, just enough to stimulate that place and I couldn't help pushing back against him. I needed more. Yes, it stung, but the pleasure building was different from anything I'd had to date.

When Luce had fucked me with toys, there'd been some of this, but it'd been crude. Will's living length inside me was something else.

"Breathe."

He pulled out, drove back in, not far, but further each time, loosening me, stroking me, his fingers sometimes dragged across my back, sometimes caught in my hair, pulling my head back, making my back arch.

"More," I panted.

"Christ, it feels as though you're trying to pull me all the way inside you!"

"More!"

He gave me more. I couldn't believe how it felt to have him move inside me, not just that constant stimulation as he brushed against that place inside, but his body against me, his hands, his touch, the scent of him.

He kept up his stroking, then leaned forward over me, pressing his chest to my back. His teeth grazed my shoulder.

"Fuck! Will," I sobbed. I needed to cum, now, right now.

He let out a contented groan and stroked in and out of me, artfully touching everything that needed to be touched.

"Fuck!" I swelled in his hand to the point of no return, and felt him slam against me and hold.

Knowing he was coming deep in my arse brought me to a climax that felt like a week's worth of pent up tension instead of however long it'd taken for him to bring me to this point.

"Will, fuck. Will." His name was a sob as he read my body perfectly, his hand on me bringing me surging to my own staggering climax. As he gripped me lightly, I rewarded him with a hot handful of cum, then another, my body tensed in the throes of a legendary orgasm.

He slid out of me and I stayed there, head hanging down, muscles trembling, unable to move.

I heard him discard the condom and then he lay down beside me and pulled me down. He put his arms around me, holding me close against him and kissed my shoulder.

"How was that?"

I swallowed. There were no words, just a tide of contentment.

He rested his head against my back and I closed my eyes and drifted, knowing life was never going to be the same again.

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yukonnightsyukonnightsover 6 years ago

Another enjoyable read. Quite sensitive under the facade of a sex filled romp with "just a mate". You have a nice way of injecting unexpected words...and it was a pleasant surprise with the turn of the table on who would be the "new bottom".

joelafayettejoelafayetteover 6 years ago
Great read

I loved this. I've been trying to find good stories that really get into the head of the top, because that's just not something I understand well. I've read a few of yours now that do that well. I enjoyed the Connor series in particular. I will use this to make my own writing better.

AnonymousAnonymousover 6 years ago
Amazing

There are no words for how good this was to read.

DeathAndTaxesDeathAndTaxesover 6 years ago
Fucking HOT!

And I loved the way you made a nod to the way a live cock feels different than getting pegged with a strapon.

buttermybiscuitbuttermybiscuitover 6 years ago

Awwww poor Jesse, he's absolutely my favorite character, I just love his attitude. Will's gonna have a lot of fun with him, I mean talk about a power bottom.

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