I could feel the tips of Charlene's erect nipples brushing against my chest as we looked into each others eyes for several seconds before she told me "Billy, I really want to do this. I'm ready — God, I'm ready! — and even though I know this isn't going to be easy, for either of us, I'm just as sure than we can make it happen."
"I want it to happen, too, Charlene", I told her, "but not so much that I'm willing to rush things or do anything to hurt you. I don't know… maybe it's wimpy, but I'd be okay with it if you wanted to kinda run things and tell me what you need or want me to do."
"No, it's not wimpy; it's actually kind of sweet; but I don't think I need to 'run' things — I know I can trust you if something isn't working right."
Looking into her eyes, I nodded my commitment to doing just that. With a lusty grin, Charlene reached between us and took my hard cock in her hand before telling me "Now that we've got that out of the way, let's see if you can get this thing where it's supposed to go!"
Grinning back at her, I shifted my position enough that she could lever my erection down. After a little adjustment by both of us, we got the end of it securely (but gently) wedged against her wet opening.
Though I wasn't pressing against the entrance to Charlenes vagina very hard, I could still feel not just how incredibly wet she was, but also how small she must be inside. Knowing how much larger my cock was compared to her vagina, it really sank in for me just how careful and gentle and patient I was going to have to be if we were going to be able to see things through. I silently swore to myself that I'd call the whole thing off rather than hurt her.
But that was going to be my last resort; until then, I had the delectable bundle of Charlene underneath me… ready and willing and eager for me to begin trying to fill her with my manhood. Slowly and carefully, I began pressing myself forward as I carefully watched her for any signs of pain (or even discomfort).
As I slowly ramped up the pressure I was applying, I began to feel it as Charlene both tried to spread her legs to make herself even more available to me, and relax her opening to let me in.
I could feel myself beginning to slip into her when Charlene told me "Billy? Could… could you stop?
And maybe even back up a little bit? It doesn't feel good for me."
Of course, I immediately quit what I was doing and let off until I was only wedged against her entrance again. A moment later, she told me "That's better. You weren't actually hurting me or anything; it just didn't feel right — like something was wrong."
"Wrong how?", I asked.
She looked thoughtful for a few moments, then told me "Wrong like all of you was trying to get inside me at the same time." She seemed to consider it for a couple of seconds, then added "When you started pushing yourself into me, it felt like your penis was trying to push the part of ME where we were touching inside me, too."
I immediately understood the problem (too much friction) and the solution (lubrication). How to implement the solution took only a fraction of a second more: reaching between us, I eased my hips back slightly and took hold of my erect penis — then carefully swirled it around Charlenes opening, getting the head well and truly lubricated with her oils before settling myself against her again.
Looking down at her, I told her "I kinda forgot something: two things will slide against each other a lot better when they're lubricated. I think it'll be a lot easier for you, now."
It took a second for Charlene to really understand what I told her; when she did, though, she surprised and delighted me by blushing faintly as she told me "I, uh, wondered what you were doing just now…"
Grinning at her, I answered "Well, that's what it's for, isn't it?"
Her blush got even darker as she answered "Yeah, I guess it is."
Managing to wipe (most of) the grin off my face, I asked "Ready to try it again?"
Realizing that we were likely to make more progress, and without causing her any discomfort, Charlene readily answered "You bet!"
Once again, I started trying to ease my erect penis into her — and immediately realized that the first problem we'd experienced had been solved: I could feel the difference her female oils made as I actually began to slip into her a lot more easily. From the look on her face, I could tell that the solution was working for Charlene, too. Even so, I was still careful to maintain a fairly steady pressure so that I entered her only as fast as Charlene was able to relax and accept me.
Progress was slow, and Charlene asked me to stop a couple of times so she could "catch her breath"; but she never again had to ask me to back up. I'm not sure, of course, but I think that the times that we stopped, the little bit of wriggling around that we did made it possible for my manhood to be re-coated from her abundant supply of womanly lubrication.
Even with the necessity of stopping so that Charlene could relax and adjust to having my penis stretching the phenomenally tight ring of her opening, it didn't take but a few minutes before both of us felt it as the last bit of the head of my cock slipped into her. When it did, I immediately stopped and held still, knowing that the relative difference between her insides and my outside meant that she was going to need some time to get comfortable with my presence inside her. It was also at that point that I remembered that she didn't have a hymen, and silently thanked the Universe that we hadn't had that to deal with in addition to everything else. The feeling of having even just the head of my cock in her made me glad that I'd already experienced the pleasure of receiving oral sex; that made it a lot easier to keep control of myself and not just blow my load in her.
While I could tell that Charlene wasn't experiencing any discomfort, it was easy to see that she was still a way from actually being comfortable, too. To help distract her (and just because I wanted to), I lowered my head and began kissing her: first on the lips, then branching out to anyplace else that I could touch them to. It took a few seconds, but my efforts began to have the desired effect: Charlene kissing me back when my lips touched hers, or making small noises of pleasure when my lips found a different target. I'm pretty sure we were well past her being comfortable before she got me to stop kissing her long enough to tell me "You can keep going now, if you want."
I kissed her on the lips again before lifting my head so I could watch her as I began pressing myself into her again. To my relief (and our mutual pleasure), getting the rest of my erection into her proved to be a lot easier that the first part had been. Sure, we had to stop a few times so she could get used to my (relatively large) presence in her (relatively small) womanhood, but it still took only as long to get the rest of me buried in her as it had the first part.
When we felt my pelvis finally pressing against hers, we looked into each others eyes for several seconds before she told me "God, you feel huge inside me — but it feels so good, too!"
I could only tell her " I feel huge inside you, too — and it feels more than good."
It felt like my entire cock was encased in one of those Chinese finger trap things; except that this particular trap was hot and wet and oh-so-tight. As wonderful as it felt to have my cock buried in her sheath, she was also almost painfully tight around me. Even though I wanted to begin moving my manhood in the incredibly wonderful environment she was providing, I knew that the right thing to do would be to remain still until she let me know SHE was ready, too. And I will always be proud of myself for doing just that: holding still in her while every fiber of my being was demanding that I just start fucking her.