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“I’m just going to use my finger right now, Ace, to help you get loosened up. Deep breath and relax. The more you fight it, the more it hurts.”
“Easy for you to say,” she mumbled as she willed her tense muscles to relax. “You’re not the one getting a finger up the ass.”
“Well, if you’d been a good girl, I would have waited until you were nice and loose from a few earth-shattering orgasms. But since you decided to be naughty today, you can wait until after your bottom is nice and full for Daddy to make you come.”
One of these days, she was going to learn to control her mouth around him. Or at least make a concerted effort to be less antagonistic. “Sorry, Daddy.”
“Hmmm, I bet you are right now.” As promised, his finger probed her asshole, pushing past the tight ring of muscle at the entrance. “How does that feel, baby?”
“Um.” She paused, taking stock of how she actually felt. “It burns, I guess? But it’s not so bad. Mostly it just feels kinda weird.”
“Good.” The finger inside of her pulled back a bit and then pushed back in, making her pussy feel strangely empty as he mimicked what she wished he was doing to her just then. “Let’s try two fingers now.”
“Two?” Her voice came out as a squeak, adding to the humiliation of having his finger in a place she never thought she’d let a man touch. “I think one is good, thank you.”
“Baby, I can promise you my cock is a good bit bigger than two fingers, so would you rather I help you stretch a little now or just jump right to the main attraction?”
“Well, when you put it that way…fine,” she said with a huff.
“Good girl. Here we go.” With that, his finger slipped from her, leaving her feeling oddly empty.
But only for a moment before two fingers pushed inside of her, stretching her a hell of a lot more than just the one had. “Oh, Daddy, it hurts! Please stop!”
The fingers inside of her stilled and she heard the sound of something opening again. “Let’s add a little more lube and see if that helps. Okay, baby?”
“O-okay, Daddy.”
More cool liquid slid between her cheeks, and he pulled his fingers out a fraction before re-entering her. The burn did ease a bit, but the sting of her muscles being stretched in ways they normally weren’t lingered.
But after a bit, even that pain faded, leaving behind only a sort of fullness she wasn’t used to feeling. It wasn’t painful or even really uncomfortable, just…different.
“Such a good girl, letting Daddy finger your asshole like this,” he crooned as he spread his fingers apart, forcing her to stretch even further. Her pussy contracted in response, and she wasn’t quite able to stop the whimper from passing her lips. “Let’s see how well you take a plug, shall we?”
“A plug?” The word felt familiar, like she’d heard the term somewhere before, but her brain was too overwhelmed with the variety of sensations battering her to pin it down.
“Yes, Ace, a plug.” His fingers slid from her, leaving her empty once again. And then something hard and far less forgiving than his fingers pressed against her hole. “Bear down, like you’re trying to push it out. That will make it easier to take.”
Although it sounded completely backwards, he hadn’t given her any reason not to trust him, so she did her best to follow his instructions while he pushed the plug further into her. Unlike his fingers, the plug grew wider and wider the deeper it went, stretching her with little flashes of pain until she worried it might split her wide open.
And then it settled into place, her muscles snapping shut around a narrower part. The pain once again faded, and she was left feeling fuller than ever before.
“How does that feel, baby?”
“Okay, I guess?” She gave her hips an experimental wiggle, but the plug didn’t move. “It won’t like, get lost inside of me, right?”
“There’s a wider base to keep it in place.” The telltale sound of a zipper reached her ears, and then the head of his cock was pushing into her aching pussy. “Tell me if it hurts too much. I’ll try to go slow.”
With the plug nestled inside of her, he felt huge. Well, he always felt huge, but now every part of her felt as full and stretched as humanly possible. “Daddy,” she whined, hating herself a little for the sound. “It’s too much.”
He paused, stroking a hand over her bare backside. “Does it hurt?”
“No. It’s just too much. Too full. Can’t take it.”
“But you will take it, won’t you, baby?” A flex of his hips had his cock driving deeper into her and she whimpered at the rush of sensation. “You’ll take all of me, because you’re Daddy’s good girl, aren’t you?”
“Y-yes, Daddy.” God, what those words did to her. More than ever, she wanted to be his good girl, his fucktoy, whatever he wanted of her, as long as he gave her the pleasure she knew he was capable of giving.
“That’s my good girl.” With short, shallow thrusts, he fucked her, driving her closer and closer to the edge of bliss but never quite sending her over.
