Diego recalled James Ludlow from down the block, a few years older than him and very much in the closet. He’d invited Diego over to play video games, then decided he wanted to try something new just to “see what it felt like.” Diego knew what he was getting himself into, but he hadn’t expected it to be so painful and one-sided. Lesson learned.
“That’s fucked up. How old were you?” Wylie asked.
“Fifteen.” It had been a galvanizing experience with Diego swearing never to be in that vulnerable of a position ever again, but there he was now, opening himself up again, this time tosomeone he hoped he could trust, someone who wanted to make him feel good. That seemed like progress, right?
“I’ll go slow, and if you don’t like it, we’ll stop,” Wylie assured him. Diego knew that was the case, but he appreciated hearing the words, nonetheless. “Did you ever tell the guy how bad it was?” Wylie asked.
“No, but he knew. He tried to get me to come over again, but I said no.” He’d avoided James like the plague after that, and any time any guy even hinted at him bottoming, Diego shut that shit down.
“And you never tried it again?” Wylie asked as if reading his mind.
“Nope.” He’d wondered, though, what it might feel like with the right person. In prison he’d been so repressed that he now felt stunted in his sexuality. “But I am curious,” he admitted.
“No pressure, right?” Wylie asked.
“No pressure at all,” Diego replied. “Just the best sex I’ve ever hadin my life.”
“Damn, I’m really starting to regret saying that.” Wylie shook his head and grinned, then grabbed some more massage oil and switched to the other foot while Diego sank further into the mattress, letting the sensation carry his more pensive thoughts away. Trust Wylie to know that a foot massage would make him as soft and pliable as putty.
“So, you like both?” Diego asked. “Topping and bottoming.”
“I’m more of a top, but I’d bottom for the right guy.” He winked slyly, and Diego wiggled his foot to indicate that he should stay on task.
“Nancy and I had a talk. About your future,” Diego said.
Wylie sighed heavily. “Uh oh.”
“It was a good conversation. She just wants you to succeed.”
“Yeah, I know, but you can’t listen to everything she says. She’s worried I’m going to give up or get distracted, and as I told you before, my taste in men, present company excluded, was pretty substandard.”
“She mentioned that too.”
“Did she warn you off?” Wylie sounded put-out by the idea of it and searched his eyes for the truth. Diego didn’t want to get Nancy in trouble, but he also didn’t want to lie.
“She didn’t need to. I’m supportive of your dreams.”
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 backto 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.”