10. Diego #3
Wylie’s penetrating stare lingered on Diego a moment longer, then he said, “Nancy means well, but she shouldn’t interfere.
This is between the two of us and no one else.
Now, I wanna talk about how warm and tight your ass is going to feel around my big, fat boner.
How your hole is going to gobble up my dick like a Hungry, Hungry Hippo and how I’m going to blow your mind with my sex game and turn you into a needy, desperate bottom. That’s the future I wanna see.”
Diego’s skin tingled and his cock throbbed. His asshole clenched, too, which may or may not have been a good thing. “Then show me, boss,” Diego challenged.
Setting his foot aside, Wylie pushed between Diego’s thighs, spreading them wide open. His confidence was back, the wolfish grin having returned as he zeroed in on Diego’s ass cheeks. “Roll over. And put your ass up in the air where I can get at it,” he commanded.
“Why?” Diego asked, even though he had some idea already.
“You know why.”
“I’ve never done that before. Or had it done to me,” Diego cautioned.
“Then let’s see if you like it,” Wylie said, easy as ever.
The man had an answer for everything, didn’t he?
But, Diego had enjoyed the foot massage and everything else they’d done so far, so maybe he’d enjoy having his ass eaten too?
He needed to get out of his own head about it.
Turning over, he braced himself on his elbows while coaching himself to hand over control for just one night, to remain open-minded and see what might unfold. A night of firsts, he reasoned.
Wylie pressed the heel of his hand against the small of his back to make his hips tilt even more. “Yeah,” he said approvingly. “Nice arch. You do yoga?”
“No,” Diego said shortly. The position was slightly degrading but also incredibly arousing. His need for dignity warred with his desire to be admired. He knew he had a nice body, but to have it praised like this, while he was naked and spread–the attention was making him squirm.
“You should. It’ll keep you flexible for me.”
The “for me” echoed in Diego’s mind, and he was unreasonably turned on by those two little words.
“I’ll do yoga when you start prioritizing protein,” Diego shot back. It was difficult to maintain sarcasm in this position, and he was trying very hard not to think about where Wylie’s mouth was headed next. At least eating his ass might shut him up for a few minutes.
“Deal,” Wylie murmured while kneading his butt cheeks with both hands. “Fucking gorgeous. Your ass is perfect, and that hole looks delectable.”
“Are you gonna write a sonnet about my asshole, or are you gonna get on with it already?” Diego griped. Wylie seemed to be drawing it out on purpose.
“I got you, baby, just relax.” The words were said soothingly as Wylie rubbed both hands along his back.
A moment later, the chatter ended and the sensations began.
First, a slow, wet lick up the crack of his ass, then a few probing dips of Wylie’s tongue that had Diego arching his back even more.
And then the wet, smacking sounds that indicated Wylie was really going to town.
Diego responded, asshole pulsing from the stimulation, opening to the penetration like a flower to a tenacious bee.
It felt… incredibly intimate and a little dirty and honestly, really fucking hot.
Diego groaned from deep in his diaphragm and jutted out his ass for more, feeling slutty about it, but whatever, he was blameless in this situation. Wylie was the one at fault.
“Fuck,” Diego grunted, shifting his knees to give Wylie better access. “You really get in there, don’t you?”
“I could eat this ass all day long,” Wylie said and smacked his lips. He spanked Diego’s ass once, and Diego’s breath caught. The sharp, stinging pain was electric, and it served to ground him. “Do you like it?” Wylie asked.
“Yeah,” Diego admitted. He lowered his head into his hands and closed his eyes in a rare act of faith—not looking over his shoulder or scanning the room for danger but trusting that for the moment, he was safe
Wylie resumed his careful torment and Diego let himself be worshipped, until his thoughts were swept away and only sensation remained.
He didn’t know how long he knelt there as his body underwent a kind of metamorphosis, shedding his inhibitions like a too-tight skin, letting go of his tightly held control to mindlessly beg for more–more pressure, more friction.
Wylie speared the length of his tongue into his hole while Diego thrusted backwards, an active participant in his own penetration.
Panting, he rode the other man’s face until he was sure he could take Wylie’s whole dick in one go.
“I’m ready,” he said, breathless and sweating, his hamstrings starting to ache from holding the same position for so long.
“Not yet. You need a little more stretching,” Wylie said.
“Are you sure?”
“Positive. Relax and trust the process, babe.”
Now, there was a lubed finger in addition to his tongue, probing and prodding and hooking inside to reach his prostate. The first time Wylie made contact with the sensitive bundle, Diego damn near lurched off the mattress.
“Found it,” Wylie said like he’d won a prize.
“Fuck, it’s sensitive.” Diego was yet again astonished by his own body’s reactivity. He hadn’t done much ass play, not with the experience of his first time and the risk of being caught at it while in prison. That had always been a No Man’s Land. Until now.
Wylie placed a firm hand on Diego’s lower back to steady him, then began the slow torment of scissoring him open, diving in to suck and lick at his entrance in between stretching his hole.
Diego felt like a caged animal–impatient, restless–as he grabbed his own nipple and pinched, hard.
He needed something else to focus on because his desire to be fucked was becoming too much for him to handle.
“Wy,” Diego said with a breathless moan.
“Yeah, baby?”
“I think…” Two fingers plunged into him now, and Diego wanted all of it. No more teasing. No more prep. “I want you inside me.”
Wylie let out a low rumble of satisfaction. “I know, but I need to get one more finger in there, then you’ll be ready. Promise.”
Diego grumbled, making his discontent known, even though it was probably the truth, especially with his history and Wylie’s size.
The last bit was torture, every nerve of Diego’s body throbbing with desire as he rode Wylie’s fingers, two and then finally, fucking finally, three.
Wylie’s other hand was gripping Diego’s dick, tight at the base to keep him from coming.
He rocked his hips back onto Wylie’s fingers, hardly even realizing it.
“Yeah, baby,” the other man coached. “Let me see you work it.”
“I’m going to come, and then you won’t have the chance to fuck me at all,” Diego groused.
“No, you won’t. You’re going to wait for me to get inside you like a good little boy. I’m going to give it to you long and deep, and you’re going to ride my dick just like you’re riding my hand. And when I tell you I’m close, then you can come.”
Wylie was laying out the terms, which was oddly reassuring. Diego swallowed his retort along with his frustration, and despite his extreme impatience, he found himself wanting to obey. Whatever Wylie wanted from him, Diego would try to give it.
Wylie released his cock and reached around him to grab one of the condoms lying on the bed. “No,” Diego said sharply. “Raw. I want to feel it.”
“Damn,” Wylie said, smoothing one hand along his back. “Okay, yeah. All right. We’ll do it like that, but I gotta warn you, this shit is fucking hot, and when I tell you I’m close, I really mean it.”
“If you come before me, I’m going to fuck you next,” Diego threatened.
Chuckling, Wylie pressed kisses all along Diego’s spine.
“Calm down, tiger. I won’t leave you hanging, I promise.
And I can always go again, lickety split.
” He squeezed Diego’s dick for good measure, then swatted the side of his ass.
“Roll over. I want to see your handsome face when I fuck you for the first time.”
Still grumbling and with his face aflame, Diego did as he was told, practically holding his legs open for Wylie to get in position and fuck him already.
Wylie stuffed a pillow under Diego’s ass and hooked one arm under his knee, then came in for a wet, dirty kiss.
Diego refused to think too hard on where that mouth had just been.
“Get on with it,” Diego demanded.
“Bossy,” Wylie commented mildly, his lubed dick nudging at Diego’s gaping hole without making any serious attempt to enter. Fucking tease.
“Deep breaths now,” Wylie reminded him and with one hand guiding his dick, he finally breached Diego’s body.
One hard push forced his cockhead past the tight ring of muscle.
It burned like hell and Diego clenched immediately, on instinct.
Wylie kissed along his collarbone and whispered, “Relax, baby. I got you,” He dragged his thumb across Diego’s cheek. “How’s that feeling for you?”
“Tight,” Diego said tensely.
“Yeah, for me too. Push out now like you’re taking a shit. I’m going to edge in just a bit more. Slowly.”
Diego swallowed and tried to follow the instruction. It was a strange sensation, pushing out to allow him in, but Wylie was focused and intent, slowly rolling his hips until the glide was smoother and his sizable girth was easier to take.
“I feel like a stuffed pinata,” Diego said.
“Well, you look like a pornstar,” Wylie replied. He kissed his forehead and the side of his jaw, staring down at him with something Diego didn’t want to interrogate too closely. Finally, Diego felt his body begin to relax.
“There you go. Isn’t that better?” Wylie coaxed like gentling a wild horse. “You’re doing so good. Let me in deeper now. It’ll start to feel better in just a sec, I promise.”
A slight shift and Wylie’s cock nudged up against Diego’s already tender prostate. Liquid lightning shot up his spine.