I wasn’t sure if I was awake enough for the massage he’d be able to give in his little headspace, but he sounded worried. I’d do anything to try to make him feel better, so I nodded.
“Sure.” I tried to remember where I’d seen our bottle of massage oil last. “Where’s the oil?”
“I’ll go get it!” Bear ran out of the room. “I want you to look like you did when I came home!”
Smiling, I decided that he’d likely seen me in the same position I’d woken up in, so I made myself comfortable and sprawled on my stomach.
“Now, be really careful with the oil. We don’t want to repeat the mistake from the other night, do we?” I told him as he scrambled on the bed with the bottle in one hand.
He giggled with delight, eyes sparkling with happiness and glee, but he nodded. He’d been trying to give me a foot massage after I’d given him one. For some reason he’d slipped into the little space during his massage and when he’d gotten to try rub my feet, well… there was still an oil stain in the couch.
I relaxed and let him play. Somehow, he managed to keep the oil spills to a minimum, and I had to admit that it was nice feeling his hands on me.
“Am I doing good, Daddy?”
“Yes, baby, you’re doing really good.”
He giggled happily and leaned over me to reach my shoulders. He slid his oily hands over them and then pulled back carefully, stretching the muscles.
“That feels nice,” I told him, hoping he’d do it again.
“Okay, Daddy,” he mumbled and repeated the motion a few more times.
On the last reach, I felt his erection pressing against my ass and tried to think fast.
He giggled when it happened, then pressed down to rub against me a couple of times.
“Uh oh, baby boy. What’s that?” I asked in a playful tone.
He still wasn’t sexual when he was little most of the time. I could still count the times he’d initiated something while in this headspace with two hands over the last few years. I never initiated anything myself, because he was too vulnerable like this, and I never wanted to feel manipulative.
“It’s my thing, Daddy!” He rubbed more, his hands losing most of the coordination. “It’s standing up.” He giggled.
“I can feel that.” I grinned at him over my shoulder. “Do you wanna rub against Daddy to make it feel better?”
“Uh-huh.” His gaze was fixed where he was letting his cock slide between my ass cheeks. “Feels good.” He sucked his bottom lip into his mouth and gnawed on it while he thrust erratically.
I pushed back against him, making him moan and giggle. He gave up any pretense of rubbing anything but his dick against my skin and grabbed onto my hips with slippery hands.
I felt myself growing hard, but in a more subdued and lazy way. This wasn’t about me.
He moved until he could put more power into the rocking and began to pant harder.
“Oh, Daddy….”
“Are you gonna make a mess on Daddy’s butt?”
His noises turned more animalistic then, his eyes still locked on where he felt so good.
When some of the sounds became the familiar, hitched gasps that told me he was getting close, I began to push back against him in a rhythm I felt he couldn’t keep up with, but that would make things better for him anyway.
“Daddy!” He gasped, then let out a long moan as I felt his cum splash over my skin.
He managed to flop down next to me instead of in the puddle he’d just made.
“Your thing feel better now?” I asked a bit sarcastically, which made him giggle and hide his face with his hands. “You know what you need to do next?”
He rolled his head to the side dramatically so he could peer at me. “No, what’s that, Daddy?”
