Desperate Measures

After a fairly restless night, Guin was almost relieved to find that Kurt had already left. Additionally, Jack had sent Jenny out for the day, as well, to prepare for an activity they would all be taking part in tomorrow. That left Guin and Jack home with just each other for the whole day.

After breakfast, they talked for a bit, Guin curled up under Jack's elbow, showing him that she wanted to be intimate, as well as telling him what she wanted to do. They weren't quite to the point where they could communicate wordlessly yet, but they didn't need to remain silent.

After some light touching and a spot of lunch, he scooped her up and carried her to the bedroom once again. The first thing they did was open the small box that Seascape had given Guin yesterday, and it was some sort of egg-shaped device with a cord running to a remote with a strap. Jack called it a vibrating butt plug, but insisted that they wait a fair bit before he would show her how it worked.

That's because today was the day they would try again. It wasn't simply rubbing or just wedging the tip in there. Today was about penetration. This time, hopefully, without injury.

Jack worked himself up this time, and once he was nice and firm, he lay down on his back. Immediately, Guin reached for the side table where the box of condoms had been, but they weren't there.

"Top drawer," smiled Jack, glad she had passed the test he hadn't even told her about. He was hoping she would remember, and would only tell her about the test if she failed. But there was one other point of review he wanted her to do. Thankfully, she passed that, too, checking to make sure it was rolling the right direction before she even tried to put it on. His pride in her swelled, glad that she remembered what he'd taught her.

After lubing him up, she climbed up onto his knees, but he pulled her down to his chest. "I don't want you slipping. If you fall, I don't want to hurt you again. So this time, and until you can adjust to the size, I want you to just back into it."

"O-okay," nodded Guin. The book had said nothing about this, nor had any of the magazines. But neither had they said anything about how much it would hurt, and Jack had a point. Plus, all of the pictures were of adult mares, and they probably had a lot more practice than she did. If this was a safety feature Jack wanted to employ, then she was ready to implement it.

Wedging the tip in, she began to push back, with Jack barely moving in response. She was the one controlling the depth. She went very slowly, stopping only when she ran into Jack's hoof.

"We're going to stop there for a second," he said, coaxing her to lie down on his abdomen. "How does it feel?"

To be honest, it hurt. Not as much as it had a few nights prior, but she still felt as if he were too big. However, there was a tingling sensation that she couldn't ignore, telling her to keep going, and it was stronger than it had been before. "G-good..."

"No, come on, tell me for real."

"It stings a bit, but I think I can do more."

With a nod, Jack removed his hoof, and she moved down, centimetre by centimetre until she felt a flaring width spreading her lips.

"I did it," she gasped. "I did it! I took the whole thing!"

"You took half," clarified Jack. "Still, that's a lot."

Guin turned her head and reached a claw back to feel that there was still a fair bit of dick before she could reach the balls. She didn't think she could fit any more in, but she hadn't taken the whole thing. She was suddenly less proud of herself, and tried to push back a little further, only to let out a yelp as she took in a little too much.

Immediately, Jack's hooves grabbed her by the thighs and pulled her back up. "Easy!" he called out. "Don't try to take on too much at once..."

"But I need to stretch out," said Guin. "I have to be able to fit all of you..."

"Eventually," assured Jack, petting her neck. "You'll be able to eventually. But don't worry about it so soon. Everywhere else in Equestria, you wouldn't be allowed to even attempt it for another three years, and even then, only with kids your own age. You're way ahead of the curve at just halfway."

She nodded and lowered her head to his chest. For a few minutes, neither of them spoke. She lay there, with him petting her shoulders to make her feel a little bit better while he waited for her to relax a bit.

"Are you ready?" he asked, finally.

"Ready for what?"

"To see what this was all building up to."

Guin swallowed, then nodded.

Gently and slowly, Jack began to pull out. The sudden vacancy created a vacuum that sucked her flesh after him, following his tip as it slipped out of her. The tingling she'd felt in her loins as it slipped in was nothing compared to this. Even the pain of sliding a little too far was gone, completely obliterated by the intense pleasure of him sliding out.

And then he went back in. He was faster than before, but that didn't matter. Whether it was the rippling pleasure she'd just felt mitigating what had happened, or the fact that she'd spent some time adjusting to his girth, she didn't know. All she knew was that it was less bad than it had been.

Then he pulled out again, and everything felt good. And then back in, and then out, and then in, and then out again. Before too long, she didn't even notice the little twinges of pain when he went in. She didn't feel herself being stretched. She could barely think of anything to compare this feeling to, other than when Jack had masturbated and licked her a few days ago, and even that was incomparable when stood up against this.

This was perfect. There was no coming back from this and returning to the way things had been before. Her life would never be the same.