Page 79 of Stepbrothers with Benefits
“Exactly,” he said, wiggling the bottle. “Water-based. But I’ll use silicone when it’s time to fuck you.”
“Noted,” I said with a laugh. I took a moment before considering what I was going to do and then rolled onto my stomach because it seemed like the best angle for him to do his thing without me needing to dangle my limbs all over the place.
I heard him suck in a breath, and I wondered what was going through his head. If it was anything like what went through my head whenever I saw him bent over or on his stomach, ass in the air, I would bet it involved a bunch of filthy thoughts about his dick being buried in me. The thought sent a nervous flutter through my gut, but I ignored it as he sat on the bed next to me, doing something before laying a kiss on my side.
“Relax,” he said with a smile as I felt something hard and cool press against a part of me that had never known anything other than fingers, small, lady-sized fingers at that. “We’ll stop if it’s too much.”
“I trust you,” I told him with a frown, because he should know that by now.
“I know,” he said, and I felt him apply pressure. I realized the coolness was lube, and the hard thing was whatever toy he was pushing into me. I raised my head at the intrusion, which, while not painful, was definitely uncomfortable. I tried not to wriggle as he eased the toy in and let it sit there momentarily, letting me adjust and analyze. “Good?”
“Weird,” I admitted with a laugh. “But okay.”
“You have to get used to all the weird and not-so-great parts before you get to the fun part.”
“Mmm, maybe you shouldn’t try to advocate for anal sex, you’re not great at it.”
“Hush,” he said with a laugh as he slid the toy back and forth.
“Still not getting much, but it’s not as uncomfortable,” I said. Something was definitely there, but it was so quiet I couldn’t really name it.
“Then let’s...” he began, leaning up again. I waited as he moved behind me, and fought the urge to see what he was doing. I figured it was another toy, but also figured it was better I didn’t see it. Anal obviously had to feel good for guys; otherwise, why go back repeatedly? Didn’t change the fact that having something dick sized pushed into your ass would be painful, and I wasn’t looking forward to that part.
Something bigger pushed against me, and when it inched in, it was with...okay, not quite pain, but it was close. I took a deep breath as Milo was careful, easing it in, and the uncomfortable pressure inside me returned. That was until I felt his mouth on the inside of my thighs, kissing and licking his way up to where his other hand was seating the toy inside me. That one was also longer, so it reached some part of me that hadn’t been touched before. I lay there, torn between the delicious tingles of his mouth on my body and the awkward feeling of the toy inside me.
“Raise your hips,” he said from between my legs, and I did, pushing back onto the toy and tensing before getting into position.
It wasn’t until I felt his free hand between my legs, grabbing my softened dick, that I realized what his intention with the position change had been. He worked the toy as he stroked me, my dick stubbornly staying half hard at best, but it drew more attention to the pleasure from the act. It was still softer than I expected, but it was better than discomfort and a faint feeling of almost pleasure.
The next toy was the one I worried about the most, even though I knew it was the final step before we got to what I’d suggested. I felt the blunt tip push against me and braced for something worse than the previous two. When he pushed it intome, it was easier than expected. In fact, it wasn’t all that different than the second toy. It was thicker, but the second toy had apparently stretched me enough that the discomfort was about the same, and just as pain-free.
“Oh,” I grunted as the toy slid inside, filling me completely as Milo never stopped stroking me. “That’s...huh.”
“I’ll take that as a good thing,” Milo said with a chuckle.
“Y-yeah,” I managed as the toy moved, slow at first but then with growing ease. The discomfort faded, and in its place was something warm and electric, growing inside me as I felt myself stiffen in Milo’s hand. “Oh shit, okay.”
The longer he moved that toy, the more I realized why Milo was okay with bottoming. The combination of toy and hand worked together to make me squirm and breathe heavier. Pleasure rippled through me, and I found myself gripping the bed cover, not out of pain or worry, but because all I could do was lie there and ride out wave after wave of pleasure. It was like the pressure of the initial entry, but with the promise of ecstasy and none of the discomfort.
“God, if this is what a dick feels like,” I moaned, not caring that it sounded a little pitiful. It was the same tone Milo used when I was deep inside him, and that was one of the hottest noises he could make. “I’m ready.”
“I’d like to think my dick will feel better.” He laughed. “Got a position preference or just like this?”
“You’re the one topping,” I said, ready to get the party started.
“Okay, on your back, legs in the air,” he said without hesitation, and I did as he said with an equal lack of hesitation.
I could see just how much he had been affected. His dick was hard enough that I wouldn’t be surprised if he complained it was ready to burst, leaking furiously at the tip and bobbing in front of him as he knelt before me. There was an intensityin his eyes, held in check by what I suspected was care for me, wanting to fuck the hell out of me but not wanting to hurt me. His movements were stiff and jerky as he pulled the other bottle of lube out to coat his dick before reaching down to pull the toy from me.
“Oh,” I grunted at the sudden feeling of emptiness. “That’s...weird.”
“Feeling a little empty?”
“Yeah.”
“It’s worse when it’s someone’s dick, especially if it’s someone you’re into.”
“Great, so I’ll be pining for your dick after this.”
