As her climax began to taper off, I figured it was time to get my "game face" on; after treating myself to one last sample of her essence, I raised up and moved so that my body was over hers. I got myself positioned over her so that I could feel her hard nipples against my chest, and with my erect penis resting on her mons – but NOT against her opening.
When she finally opened her eyes and saw me, she gave me a smile of delight before telling me "Your friend was right – you really are almost as good at that as another woman!"
The two of us exchanged an affectionate kiss, and after she'd lowered her head to the bed again, I softly asked her "Do you think you'd like to have a try at starting a family?"
She looked at me for a second, then realized how I was positioned over her; a moment later, I could see from the expression on her face that she'd discovered where my erect penis was.
I was sorry to see all the joy and happiness go out of her face, but found some consolation in the fact that nothing worse happened. I could hear the note of resignation in her voice when she answered "I know it's got to happen if I want to have a baby, so I might as well say 'yes' and get it over with."
A moment later, she looked up at me and asked "Why didn't you just… start, instead of waiting and asking me?"
I lowered my head and gave her a tender kiss on the lips before answering "Gina, I wouldn't do that to you – it would be too much like I was raping you, or something, and I'm not that kind of guy. I'm only going to do this with your permission, and only as fast as you're comfortable with."
From the expression on her face, I knew that I'd surprised her a little bit – and pleased her, too. After a second or two, she told me "Okay, Jim… you have my permission, if that's what you need."
Slowly, I shifted myself so that my erection slid back and down so that the head was generally touching her vaginal opening. Gently, I told her "This will be easier for both of us if you can bring your knees up, and open your legs a little more."
Keeping her promise to be cooperative, she did as I suggested; after a little minor adjustment, I could feel that the head of my cock between her vaginal lips and lightly wedged against her opening. I could also feel that she was more than a little tense. I gave her another soft kiss before telling her "Gina, if there was another way for us to do this, I'd be delighted to do that, instead. But there isn't another way, so if I'm going to get you pregnant, I'm going to have to be inside you. I know this is the first time for you, and I care enough about you that I don't want to hurt you. So I'm going to ask you to let me know what YOU want – do you let me in, so WE can make this as easy and painless as possible? Or do you want me to just get it inside you however I can, and go from there? Like I said, I don't want to hurt you – but if you want a baby that bad, I will if that's the only choice you give me. Or do you want to call it off?"
She immediately exclaimed "NO!"; a moment later, and a little calmer, she told me "No, I don't want to call it off. And I don't want you to just 'get it inside', either. Can you give me a second, so I can at least try to see I can do something that would help?"
"Of course I can", I assured her. "I'm willing to give you as much time as you need, for as long as you want me to, if it'll help."
Holding myself steady over her, I could feel as she tried to relax – both the entrance to her womanhood, but the rest of herself, as well. When I figured that she'd made enough progress that it might be worth trying, I told her "Okay, Gina. If it's all right with you, I can start trying to see if I can get inside. You'll be able to feel me pushing, but I am not going to force it to happen. If you want me to get you pregnant, it's going to be up to you to let me in. I'll be perfectly happy to stop any time you tell me to, and wait for however long you want. I really, truly did mean it when I said that I don't want to hurt you, okay?"
Somewhat relieved by what I'd said, she nodded her understanding. I gave it a few more seconds, then began to slowly increase the pressure of my dick against her opening. Realizing that I really was taking my time and trying to be gentle with her, I felt her relax even more. As the seconds ticked by, I could feel myself gradually penetrating her farther and farther as more time passed without my causing her any pain or (obvious) discomfort. There were a few times that I felt her begin to tense up; when it happened, I immediately stopped so that she'd know that I wasn't trying to force anything to happen. Each time, she was able to "recover" a little faster and easier, and it was a little longer before it happened again.
I knew that I was getting close to the head of my manhood slipping through the tight ring of her entrance, so when it finally happened, I was able to hold myself still on (and in) her before she could even react. Looking down at her, I could see that she really wasn't pleased about having me there – but I could also tell that she wasn't in any pain or significant discomfort, either. I managed to lower my head so that I could give her a soft kiss on the forehead, and she found it in herself to give me a brief smile in return. To put her mind at ease, I told her "I'll just wait like this until you tell me you're ready for me to go on, okay?"
I got a little bit more of a smile in response before she answered "Thank you, I'd appreciate that. You aren't hurting me or anything, but you're bigger than anything I've ever had there before, too. I just need a little time to get used to you."
I readily told her "That's fine, Gina. I told you I'd stop when you needed me to, and that I'd wait until you said you were ready to go on – and I meant it."
It was probably a full five minutes before she looked up at me and nodded, letting me know that it was okay for me to continue. After sliding myself back and forth in her a few millimeters to try and wet myself with her oils, I once again gradually increased how hard I was trying to slide myself into her. I got perhaps an inch more of my erect manhood before I saw her start to get a troubled expression on her face. Rather than wait for her to say anything, I simply eased off and held myself still again. When she looked up at me, I could see that she appreciated what I'd done. It didn't take quite as long before she let me know that it was okay to go on. Able to move inside her a little more, I was better able to get her lubrication distributed before starting to ease myself farther into her.
I got maybe another inch and a half of my erection through her portal before I saw that I should probably stop again. I got another brief smile from her, and it didn't take but a couple of minutes for her to tell me she was ready again. After making sure I was well-wetted, I picked up where I'd left off. I'd gotten roughly three quarters of myself into her before she asked me if I could wait a moment; I promptly backed off from what I was doing, and waited patiently for the minute or so it took for her to tell me it was okay to go on.
My pubic hair was merged with hers before I had to stop again. Looking down at her, I said "That's about it, Gina. There's a little bit more of me that will go in, but not until after I've been moving in you for a little while."
From the expression on her face, I could tell that she was a little surprised by what I'd told her. After a few seconds had gone by, she hesitantly told me "It… it's not as bad as I thought it would be. I still don't really like it – but I can live with it". A few moments later, she added "Thank you for taking your time, and being so patient with me. You were very gentle, and there were only a couple of times that it was uncomfortable. You promised me that you'd make it as easy for me as you could, and that's what you did. That means a lot to me."