With those questions in mind, Jeremy went back to his investigations, resolving that he wouldn't hurt Dawn in the process of getting the answers he was after. It took just a few minutes of patient, careful, and gentle probing before he finally concluded that her hymen didn't feel all that thick or tough to him, and that he didn't figure that it would be that difficult to past it. What Dawn might think was something else entirely, however. It was after he'd reached that point that he realized that as careful as he'd been getting his finger that far, his erect cock would be even more of a problem. Shortly on the heels of that, he understood that just as Dawn had seemed to stretch inside to accept his finger, she'd stretch to take his cock – but that if he could get even just a couple of his fingers inside her, it would make things easier for her. It wasn't but a few moments before he started putting his thoughts into action.
Dawn hadn't said anything, but Jeremy's efforts to learn something about her maidenhead had caused her a little discomfort. But he'd never actually hurt her, and knowing why he was doing it made it a lot easier for her to put up with the different sensations he'd caused. She was a little disappointed when she felt his finger leave, and was starting to wonder why he'd pulled it out when she felt him at her opening again. It took nearly a minute before she realized that he was trying to get two of his fingers inside her; that was quickly followed by the understanding that he was trying to make it possible to at least start getting his dick inside her without hurting her too much. In response, Dawn tried to cooperate by relaxing herself and making it as easy for him as she could.
Jeremy's attention was on being careful to go slowly and patiently, so he didn't really notice that Dawn was trying to make things easier for him. All he knew was that after several patient tries, he was finally able to start worming his middle and ring fingers past the tight ring of her opening. Once he'd accomplished that much, it wasn't that much longer before he'd equaled his previous gains.
Dawn was willing to tolerate the greater discomfort – almost pain, really – of what Jeremy was doing because she knew that it was actually going to make things easier later on: his cock was a lot bigger than even two of his fingers! She wanted it to happen, so she continued trying to relax herself; by accepting what was happening to her, it wasn't but a couple of minutes before the sensations weren't as bothersome as they'd started out. In fact, they were starting to feel kind of… nice, actually…
Jeremy had reached the point where he was slowly sliding the ends of his fingers in and out of Dawn, and slightly twisting them a bit as he did to try and 'open her up' when he heard her say "I'm getting used to that, Jeremy – what you're doing with your fingers, I mean. I… I think that if we do something first, it'll be okay for you to get inside me."
Releasing the rubbery nubbin of one of her nipples from his mouth, Jeremy asked "What's that?"
"I think it would be easier if I was wetter, you know, on the inside; and more at ease, like I am after I have an orgasm."
Jeremy couldn't resist grinning at her as he replied "If you think you want me to help you climax first, I'd be glad to do that, Dawn."
She had to grin back as she answered "It won't just be you doing me, Jeremy. I want to get you hard, and as slippery on the outside as you make me on the inside!"
With that, it took them only a few seconds to get themselves repositioned; by unspoken agreement, Jeremy was the one on top so that Dawn wouldn't have to move around on the towel any more than necessary. His head poised over his sister's pelvis, Jeremy once more had to marvel at the beauty and delicacy of her womanhood: the dark wedge of her luxuriously soft pubic wedge, the thin soft lips of her sex, and the distinct shine between them. He again marveled at his good fortune before lowering his head between Dawns thighs, and extending his tongue so that he could collect a sample of her nectar…
Beneath him, Dawn was experiencing much the same feelings – and more. Knowing that she was soon going to have the cock she was looking at inside her easily brought on the hollow sensation between her legs that she'd gotten used to. The idea of having Jeremy's penis moving in her had her vagina and breasts almost aching in anticipation. She knew that there was still the problem of getting past her hymen; but she loved and trusted Jeremy enough to know that if it was going to hurt, it would be as small a pain as could be managed – and that after that, she'd be free to take full pleasure from what she'd only been able to dream about to that point.
For his part, Jeremy was more than willing to apply himself to helping Dawn have an orgasm. He really did love her – even if it wasn't the way he knew two adults would; that he delighted in her taste and made her feel so good and she liked to do things with him, too, only seemed to make the whole thing perfect. And now… to be doing it now when she wanted to give him her virginity… well, that was about the best reason he could conceive of.
So Jeremy went about his assignment willingly, and with great pleasure. Because they were in the reverse of their usual position, Dawn wasn't at the same 'angle' to him as she usually was: the opening to her vagina was a little more difficult to get to (even with Dawn arching her pelvis up in welcome to his efforts). But her clitoris was a lot easier to reach, and Jeremy had learned that attention to it was what pleased her the most. Still, he was determined not to rush her, so he was careful not to pay too much attention to the little pearl of flesh at the top of her cleft. It wasn't but a couple of minutes before his tender ministrations had her labia parted and the area between them glistening with her essence.
Beneath him, Dawn was finding that having Jeremy on top of her complicated things for her, too. With Jeremy positioned as he was so that he could get his head between her thighs, it left his cock jutting out at the wrong angle. Instead of being pointed toward her as she was used to, it was going the opposite direction; without having to be told, she knew that trying to lever it down and back so she could get her mouth around it would be uncomfortable enough to negate the pleasure of what she wanted to do. After trying to figure out something, she finally realized that she was simply going to have to content herself with using her lips and tongue on the outside of him – and on his balls. She felt a little disappointment that she wouldn't be able to give him as much pleasure as she usually did before she realized that not stimulating him so much was probably a good thing, considering why they were in the position they were in…
When Dawn started 'biting' at his erection with her lips, it took a few seconds before Jeremy realized that their change of position was causing problems for Dawn, too – and considerably less time for him to come to the conclusion that her limited abilities were probably for the better: it had finally gotten through to him that deflowering his sister meant that he was finally actually going to get to fuck for the first time in his life. The anticipation of that singular event was dramatically raising his arousal, and he was afraid that if Dawn had been able to get her mouth on him as she usually did, he'd finish before he even got started!
The next several minutes went by with each of them readily applying themselves toward getting the other ready for what was next.
Jeremy could feel Dawn nuzzling his balls as he was slowly fluttering his tongue across her clitoris; from the soft moans she was releasing and the way she'd spread her thighs and was arching herself up at him, he knew that she was on the edge of finding her release from the pleasure he'd been bringing her. It took only a second for him to decide not to draw things out any longer; he suddenly changed to circling her clit with a firm but gentle pressure, and it wasn't but a few seconds of that before he felt his sisters body tense beneath him with the start of her climax.