“Are you sure about this?”
“I wouldn’t have said I was sure if I wasn’t, Ian,” Theodore said, smiling up at Ian, hands on Ian’s sides. “Come on, I’ve never lied to you before, have I?”
No, Theodore hadn’t. He’d never outright lied to Ian, though he did often lie to himself and then use that as a way of telling Ian something that wasn’t true. Sometimes he said something like ‘I just liked the look of him’ or ‘I need people to take me seriously’ and what he actually meant was ‘he’s younger than you, he’s prettier than you.’ Sometimes he said ‘when did you grow so much hair’ or ‘you’re so big suddenly,’ and it meant ‘I wish you hadn’t grown so much.’ Sometimes he said ‘I worry that you don’t like having sex with me’ and it meant ‘I don’t want to have sex with you.’
Sometimes he said ‘I want you to be on top tonight’ and it meant ‘I don’t want you but I wish I did.’
And Ian may not have been a genius, but he was an expert in speaking Theodore, so he just touched Theodore’s face and smiled. “No,” he said. “It’s one of the reasons I love you, Theo.”
“I love you too, Ian,” Theodore said back, pulling Ian down a little. “Let’s go, I want to know what it’s like.”
Ian nodded, kissing Theodore because he could. “You’ll like it, I promise.” He’d never been on top before, but he was going to make sure Theodore enjoyed it. “It’s really nice.”
“I believe you,” Theodore said, and what he meant was ‘I want to believe you.’ That was okay. It was close enough.
Ian kissed Theodore again, then sat up and uncorked the oil, pouring some onto his hand. He made sure it was on his fingers before rubbing his hands together a moment. He smiled, took Theodore’s still-soft dick in his hand, rubbing it while he slid his other hand down, circling Theodore’s hole with a finger. “You have to try and relax a little,” Ian said, keeping up both motions. “You’re really tense.”
“It’s…somewhat hard not to be,” Theodore said, neck bobbing as he swallowed.
“I know,” Ian said. “But you can do it. I’m going to push my finger in now.”
And he did, kind of enjoying the noise Theodore made when he did that. Ian was fully hard even if Theodore was still only partly there. He pushed his finger in past the first knuckle, pausing to move it around a bit, stretching out Theodore’s hole some more. Part of him nagged that he was never going to fit inside Theodore, but Ian knew from experience that a lot could fit in there if he tried hard enough.
But he didn’t want it to hurt like it had his first time, so Ian went slowly, masturbating Theodore all the way, making sure he enjoyed it enough that even if the finger inside him wasn’t fun, at least the hand on his dick was. Theodore was hard now, and Ian stroked him while pushing farther in, until his finger was buried. “How’s that?”
“It’s…a strange feeling,” Theodore panted, a light sheen of sweat on his chest.
Ian nodded. “You get used to it, though,” he promised, moving that finger around. “And there’s something in here that you’ll like, promise.” He had to find it, though, which took a good minute or so. But Theodore gasped at the touch, and Ian grinned in triumph. “See?”
“Yes, I…I do,” Theodore said, twitching in Ian’s hand.
Ian nodded, and now slowly started to push in a second finger. “A bit more before you’re ready for something bigger,” he said, keeping up the pressure on Theodore’s dick when he started to tense. “Don’t freak out, stay relaxed.”
“I’m trying,” Theodore told him.
“I know.” Ian kept pushing, and after a few minutes he was all the way inside. “There. See, you can do it.”
Theodore nodded. Precum was beading at the tip of his cock now. “It…it seems I can. I am ready, however, for you to use something else, Ian.”
Ian frowned. “Are you sure?” Theodore could use a few more minutes of preparation, just to get used to it.
“I’m quite sure. Else I’m afraid I’ll finish before you ever insert yourself,” Theodore said with a chuckle.
Ian had to stop a giggle, slowly pulling his fingers out of Theodore. “Okay,” he said. He was glad—Theodore was enjoying this, it seemed like. He didn’t hate it. Maybe this was something they could do more often. Something they could do together that wouldn’t require Theodore to pretend Ian was still thirteen years old.
Theodore made a noise of discomfort when Ian’s fingers popped out, but Ian gave his dick a squeeze. “Just one second,” he said, using his free hand to pour more oil right onto his dick, smearing it around, surprised at how good just doing that felt. He’d enjoying fingering Theodore more than he’d expected to.
Then, Ian got onto his knees and lined himself up with Theodore’s hole, hand shaking. “I’m going it in now,” he warned. Theodore nodded, eyes shut. Ian looked down to make sure his aim was right, guided his dick to where they both wanted it to go.
Theodore was still so tight when Ian pushed in, and Ian couldn’t get far. “Relax, Theo, it’s just me,” he said, leaning down to give him a kiss on the cheek. That had always calmed Ian down when he was nervous. “Let me in.”
“It’s…it’s not as easy as you make it sound, Ian…”
“It is,” Ian promised in a whisper, kissing Theodore again. “Just relax and let me do everything.”
Theodore nodded, taking deep breaths, and after a second he relaxed enough that Ian could pop in, which earned a gasp from both of them. “Th-there you go,” Ian said, moving. “There you go…”
From there it was a simple matter of moving back and forth, getting a good rhythm going. He pushed deeper and deeper in, tightening his grip on Theodore’s dick, stroking him in tune with his thrusts. Ian couldn’t believe how awesome this was, how great it felt to be on top like this. Was this what it was always like for Theodore? No wonder he’d never wanted to switch before now. It was so much, and having Theodore under him was…
Ian really liked it. He liked it so much he got lost in it, forgetting what he was there to do and just fucking Theodore, kissing him, stroking him, taking complete control over Theodore’s body, reacting to Theodore’s every moan, every movement, and soon Theodore was exploding in his hand, hot cum searing his palm, spilling onto Theodore’s belly as Theodore cried his name.
Ian should have stopped when Theodore came, but he didn’t, he kept going, kept pushing, deeper and deeper in until he was there too, ramming himself inside Theodore as he came, holding Theodore tightly as he did.
Only after several minutes had passed did Ian have the presence of mind to pull out, to let go of Theodore’s sticky dick, to cuddle with him. “How…how was it?” he asked, trying to find a comfortable way to lie without his collar digging into his neck.
“It was…very good,” Theodore told him, holding Ian close. “Wonderful. I see why you like it.”
Ian nodded, part of him realizing that that was Theodore saying one thing and meaning another, but too tired and happy to parse it. “Me too,” he said instead. “I’m…I’m glad you liked it, Theo.” He felt content, and whole. And like maybe, this was something that could change between them, that if Theodore had liked it too, maybe they could do this from now on and then Ian wouldn’t have to worry about Benny or whoever else Theodore might end up looking at who wasn’t him. Maybe they could have this and not have to worry about anything anymore.
And maybe Theodore wasn’t the only one who was good at lying to himself.
Theodore pulled Ian closer, putting an arm around him, holding him close like he had when they’d been younger. “I love you, Ian,” he said.
Ian nodded. The way Theodore was holding him was making his collar pull a little. “I love you too, Theo.”