"It's okay, honey", I assured her. "There are three ways that people usually use when it's a girl's first time. The easiest one for her is if the guy is on the bottom, and she's on top. That way, she can put herself ON him however fast or slow she wants to, or even back up a little bit. Another one is if she's on her hands and knees, and the boy is behind her; that way, she isn't doing everything, but she can still move if it starts to hurt, or doesn't feel right to her. The last one is if the girl is on the bottom, and the guy is on top of her. That's probably the most common one, because that's how most people usually have sex. That one's good if the girl absolutely trusts the guy not to hurt her, or if she's afraid she won't be able to make it happen when it's time to stop being a virgin. As much bigger than you as I am, I think it would be easiest and best for you if we used the first one – with you on top of me. But I told you that I wouldn't hurt you, and I won't, so whichever one of those you like is what we'll do."
She had to consider it for only a few seconds before telling me "I think the first one is best, too. I know you wouldn't hurt me on purpose, but if I'm the one on top, then you don't have to worry about it."
I suspected that she was having something of an attack of nerves now that it was actually going to happen, but was willing to accept the reason she'd given at face value – after all, the whole idea was for her to be able to have her first sexual experience with as little pain or discomfort as possible.
So what I told her was "Thank you, I appreciate that. Now, if I lay down, it'll probably be a little easier for you to what you want to; but if I'm sitting up or leaning back like this, then I can touch you better afterwards, or even help you while it happens, if you want."
Pleased, she told me "I'd like you to stay like this – I want you to be able to touch me! Um… what do I do?"
Cupping her face in my hands, I moved forward enough to give her a soft kiss on the lips before looking her in the eyes and gently telling her "Just do whatever you're comfortable with, and doesn't hurt you, honey. It'll be easier for you if both of us are slippery, though – you on the inside, and me on the outside. When you're ready, you move so that you're right over me; you hold my penis where it's supposed to go, and then just kind of sit down on it – but only as fast or far as YOU want, right?"
With a lusty grin, she answered "You betcha!"
Remembering what else I'd said, she wasn't the slightest bit embarrassed to reach between her thighs and check that she was (still) wet inside. Following that, she took hold of my penis; discovering that it was dry, I saw her eyes twinkle with humor as she quickly scooted herself back so that she could lean forward and take me into her mouth again. After bobbing her head up and down for a minute or so, she let me slip from her mouth, leaving me glistening with the saliva she'd left behind.
She got herself positioned at my hips again, and took hold of my erection; after she levered it up and got herself positioned against it, she realized that the angle wasn't quite right. After she'd moved forward a bit, she tried it again, and found the results satisfactory. I put my hands on her hips, which didn't bother her in the slightest – all I was doing was steadying her, without applying any downward pressure. When she looked into my face, I told her "I really mean it, Gail – only as much as you're comfortable with. Take your time, and don't hurt yourself. I'm not in any hurry, so don't you be. I'll just wait right here until you're done, I promise."
She'd nodded at the appropriate points when I was talking, and graced me with a small laugh when I was done.
With nothing left but the deed itself, I was prepared to wait however long it took for her to either start impaling her fifteen-year-old vagina on my man-sized cock, or call it off. Still steadying her with my hands on her hips, I sat there in silence, watching her.
Honestly, I was a little surprised at how soon she began to press herself down on me; I'd thought that she'd have to gather her courage for a little longer. From the way she was moving, I got the idea that her first couple of attempts were more to test herself than with any thought of actually having anything happen. The third time she pressed down, I knew that she really meant to get me inside.
I could feel myself begin to penetrate her, a little, but I could also tell that her opening was still too small and tight. After a few seconds, she gave up the effort, and raised up a little bit. A couple of soft squeezes of her hips got her to look at me so I could tell her "Maybe it'll help if you don't try to push yourself onto me, and try to LET me in, instead."
She nodded her understanding, and after taking a breath, tried it again. That time, I could feel as she tried to relax herself – and succeeded in getting a bit farther onto me before backing off. She lifted her head to tell me "It does help… that was a lot easier than last time."
I smiled and mimed kissing her, making her smile in return.
Several more tries followed, and it was plain that each one was a little easier for her – and each got her that much farther onto my manhood. She was making the effort again, and I could tell that I was on the verge of slipping through her opening when she began to raise up again… only to reverse direction, and allow herself to almost fall onto my dick. I not only slipped through her opening, but into her for perhaps a half inch – accompanied by a soft cry from her.
I was trying to lift her off of me when she told me "No, it's okay, Jim. It only hurt for a second; I was surprised, more than anything else."
I looked at her reproachfully as I said "Honey, I don't think it had to hurt at ALL. The way it felt to me, I'm almost positive it would have happened the next time; the one after that for certain."
"Maybe", she conceded, "but now it has happened – you're inside me… and it feels good!"
I muttered something about impetuous youth under my breath before answering "Okay, fine, I'm in you, and it feels good. Now, take it easy for a bit, will you, before you go on?"
The tone of voice I used must have let her know that I wasn't particularly happy about what she'd done. I could hear the contrition in her voice when she answered "I will… honest. I could tell it was close, too, and I just wanted it to happen, was all."
To let her know that I wasn't upset or angry, I took her into my arms and hugged her before telling her "I can understand that. I just wish you hadn't been in so much of a hurry and gotten hurt, is all."
"I'm sorry, Jim. I'll go slower from now on, I promise", she answered.
After giving her a kiss so she'd know she was forgiven, I released her to sit up again. I readily took advantage of the opportunity to get my hands on her again, from her knees to her shoulders, and paying extra attention to her tight little ass and lovely breasts. The expression on her face told me that what I was doing pleased her – not only physically, but in her heart.
After a few minutes, she was ready to continue. With my cock firmly embedded between her labia, she was able to lean forward and support herself on her arms. That brought her close enough that I could lift my head and get my mouth on her nipples. With my mouth at her breasts and my hands on her ass, Gail began to press herself down on me again… slowly and carefully, as she'd promised. She would settle herself onto me a little ways, pause for a bit, then raise up to make sure we stayed lubricated before lowering herself a bit farther. She got as far as having half my cock inside before I had to lower my head from her mammaries. Looking between us, I could see how tightly her labia were wrapped around my penis; when she raised up, I saw something that surprised me.
A few seconds later, Gail realized that I was looking at her intently; baffled, she asked me "What? Why are you looking at me like that?"
Reaching between us, I ran my finger along the line where we were joined before showing it to her. Seeing the traces of blood I'd seen, she looked at me in surprise as she said "I didn't know. All I felt was that little bit of pain at first – it only lasted a second, and there hasn't been anything else since then!"