dreamland (bill skarsgard one shots)

18. trust

"Well have you ever tried it?"

"No."

"I honestly think you'll end up liking it. It's a weird kind of pleasure, but it's nice." He still didn't seem completely on board, so you made a proposition. "Okay, how about you test it out on me? I've worn these things before, I'll let you put it inside me. You can even fuck me while I'm wearing it."

At that, his eyes practically fell out of his head. "Seriously?"

"Yeah! I've had plenty of practice with it, it's no big deal for me."

"I guess we can try it then," he agreed.

And so, you did. You got everything ready, cleared off the bed, took off your clothes (add in a little making out and grinding on each other as well), and grabbed the lube.

"Use lots of it," you told Bill. He had the bottle of lube in one hand, and the plug in the other, looking at both of them before looking at you.

You were spread out for him, legs parted, ready for him to make the first move. With a deep breath, he finally did. He got the plug slippery enough, using more lube than he even needed. The moment you felt the coolness against you, you hissed. Bill froze then, looking at you with wide eyes. "Are you okay?"

"I'm totally fine, keep going."

He complied, slowly inching the plug in until it was totally in place. He leaned back to glance at it, deciding it looked adorable. He spent so long staring at it that you had to nudge him to pull his attention back to you.

That night, he fucked you hard and deep, and everything felt so much more...erotic. The sounds you made had Bill's head spinning, and he found himself periodically reaching down to brush his fingers over the plug you wore.

Once it was all said and done, his curiosity was most definitely piqued. He was even reconsidering his previous refusal to even try a plug. And after you'd cleaned up and were cuddled up in bed together, he said, "I think I'd be willing to try it...a plug. You made it look so hot."

At this, you grinned. "We can definitely try it."

And thus began a very interesting journey. You started small, of course. Little by little. The first night you tried it was rather interesting. You had Bill in front of you, in a position he was most comfortable in. You made certain he was relaxed. You kissed him all over, ran your hands down his bare body, assured him that you could stop at any time, no questions asked.

Fingers were the first step. Slow and steady, your middle finger and plenty of lubricant. Bill tensed the moment he felt you against him, but you were right there with him, soothing him, telling him to take deep breaths. You spent quite a bit of time with him, easing your finger inside, so slowly.

You communicated with Bill the entire time. Asked him how it felt, made sure he wasn't awfully uncomfortable. It truly was an odd sensation, but he couldn't say that he hated it. As time went on, he began to grow accustomed to your fingers, and even began to enjoy the feeling.

But then came an entirely different feeling when you introduced a plug. You took it slow, as with everything else. It was uncomfortable at first, and you worked through a lot of whimpers and groans. But Bill found that, after it was all said and done, it made him feel very submissive. Small, even. And he liked it quite a lot.