Unexpected Top(24)

“Yeah, you know, maybe just a finger or two.” At Cissy’s raised eyebrow he plowed on. “I think you might like it and I really, really want to make you come.”

She laced her hands behind her head and contemplated him. “Tell you what. I got a butt plug with all that other stuff at the sex store. If you wear that I’ll let you try what you want in my ass.”

“Y-you want me to put something up my ass?”

Hasn’t it been through enough today?

Cissy smirked, and Len didn’t feel comforted in the least. “Are you afraid? Do you honestly want me to turn my ass over to you, no questions asked, without reciprocation? Prove to me you think it would be pleasurable. Put the plug in your ass. Or I could restrain you and do it for you…”

He knew when he was being challenged and it was pretty arousing that Cissy was willing to stand up to him like that. How badly did he want Cissy to come? Already it looked as if she was losing that just-before-orgasm edge. While the thought of Cissy tying him down and forcing him to take the plug made his cock throb, he figured the first time he tried it he should probably be in control.

“Okay. But I’ll do it.”

She smirked again, and he really didn’t trust that look. He felt a little like he’d been conned, but he knew Cissy wouldn’t do anything that would injure him. Besides, she’d gotten the plug to be used on her, from what he could gather of the motivation behind her going to the sex toy store to begin with.

He felt a bead of sweat roll down his temple. Maybe he should’ve asked how big the plug was, though, before agreeing. But then she reached into the nightstand and he let out a relieved breath when he saw the package and the plug itself. It was labeled small and wasn’t much thicker than his index finger. Cissy also removed a small bottle of lube and he wondered what else she had in there that she’d never shown him. He couldn’t blame her; he’d been a royal ass when she’d tried to introduce the toys, thinking he was enough for her by himself and that he didn’t need toys.

What a conceited fucking jerk he’d been. His gaze shot to Cissy’s as though she could hear his thoughts. If he was going to curb his swearing he was going to need to start in his own head. He had no doubt whatsoever Cissy would spank him for his mouth one day soon. The habit had formed long ago and would be difficult to break, even with his ass literally on the line.

He waited, more sweat trailing down his back and his chest as she slicked the silicone plug with lube and then handed it to him. This had to rank as one of the weirdest things he’d ever done—weirder even than baring his ass for a spanking a short time ago, and that was saying something. Figuring the plug would go in easier if he was on his back, he rolled over. As soon as his ass came in contact with the sheets, he groaned from the combination of pleasure and pain the movement inspired. Not wanting to delve into that too quickly at the moment, Len hurried to pull his legs up. Spreading his thighs wide, he took a deep breath, remembering he was doing this for Cissy.

As the slickened plug began to slide into his body, he tried not to freak out over the notion of something going inside a place only meant for things to leave. Obviously tons of people had anal sex, a lot of people loved it, so it must not be that bad. Hell, he wanted to try it with Cissy, but as the plug slid in farther and his ass clenched against the invasion, he could see how a woman might not be too keen on this. To say he felt full would’ve been a colossal understatement, and this thing wasn’t even half as wide as his cock.

The plug seemed to not want to go in any farther but there was still a lot of length left. “Fuck!” He instantly looked over at Cissy, who was frowning.

“I’ll give that a pass. Try unclenching. I think it will help.”

At least she hadn’t decided to spank him for swearing. The moment the word had left his mouth he’d been really afraid she was going to go at his already-sore ass again. With a profound sense of relief, he consciously tried to relax the muscles in his ass and then pushed harder. The plug slid past whatever had been impeding its progress, providing him with the absolute oddest sensation he’d ever felt. Finally the damn thing was seated and he let out a long, slow breath.

“I think it’s okay.”

Now she gifted him with a genuine, warm smile. “You did great, honey. Thank you for doing that.”

Len gingerly rolled over, feeling the plug shift as he did so. Man, that was a weird feeling. Not bad, but weird. He’d never had anything in his ass before and it was as if his brain was still fighting the idea but the part actually plugged was on board. He looked back at her. “I wanted to make you happy. I owe you so much. Thank you for not giving up on me. I promise I’ll try to be better, and if I’m not, well, you’ll spank me again and I’ll deserve it.”