Maintaining my guise of calm acceptance, I sat next to her before telling her "Em, I know that this is the first time you've done anything like this, so I want to make sure you know that I'm not going to hurt you. Because I'm older, I know that there are things that I can do that will help make you excited enough to have an orgasm, and I'm going to do them — unless you decide that you don't like them. If you do, TELL ME, and I'll stop, okay?"
Interested, but not afraid, she asked "What things?"
Smiling, I told her "Things like kissing, and touching you different ways and on different places.
Kissing your boobs. Stuff that really hurts a lot.", teasing.
Page 13 of 68
A Good Neighbor — Copyright © 2009 — Dorsai
http://www.asstr.org/~Dorsai
She grinned at my description, knowing that I wouldn't hurt her, before nodding her head in understanding.
"Now, if I start to do something you're not sure about, I'm going to ask that you at least give it a try before you decide you don't like it. Like I said, I'll stop if you want me to — just what I'm doing then, or completely, if that's what you want, any time you say. But like I said, some of those things are stuff that I think you'll like if you give them a chance, too. You've never had an orgasm before, so we are going to help you have one by finding out if there's something new or different that will help, okay?"
"I understand, Gary. I won't tell you to stop unless I'm really sure."
Next, I told her "Emma, there's something that I want you to know."
As she looked up at me in curiosity, I continued "There are probably girls at school that you hear people talking about." She nodded, and I went on "To those girls, the things they do with boys…
it just doesn't mean anything to them. Oh, it probably feels good, but they don't think of it as anything special. So because it isn't anything special to them, they aren't very careful about what guys they're with — and because what they do isn't special to the girl, then the girls isn't special to the guys. So because the girl isn't special to them, the guys tell each other about what happened, and it isn't long before everybody is hearing about it. What I want you to know is that I think you're special, and that it really means a lot to me that you trust me to do this with you.
What I feel about you is more than just liking you; you could even say that I love you. Not like your mom and dad do, or that I want us to be married or anything like that — but what I feel is still love. I hope you understand that I'm willing to stuff like this with you because of that love, and that you'll be careful and picky about any guy that you're with. I love you too much, and think you're too special, and I care about you and want you to be happy."
"But I do think this is special, Gary, and I… I love you, too, like you said — caring about you, and wanting you to be happy, too. If you weren't already somebody special to me, I never would have asked you to help me like this, or even started talking to you about all that other stuff. I loved you, and knew that you loved me, and that's why we're like this, now. But it was still nice to hear you say it."
After giving her a smile in answer, I got myself stretched out next to her, and propped up on my elbow. I could see that she was a trifle nervous, so the first thing I did was to reach out so I could softly cup her face in my hand — something that I could see surprised her a little bit. Lowering my head, I briefly touched my lips to hers as softly and chastely as I could. When I pulled back, I could see in her eyes how much that small, simple gesture meant to her. When I kissed her again, it was just as tender and innocent, but lasted longer when she started kissing me back.
She was a little hesitant at first; it took a couple of times before I realized that at her age, she was likely nervous about getting it "right". After a few more kisses (and my non-verbal encouragement) she seemed to realize that there wasn't really any way to get it wrong, and was soon returning my kisses easily and comfortably.
When we'd reached that point, I gently caressed her face for a little bit before slowly drawing my hand down her throat, then between her breasts, and finally coming to a halt with my hand splayed just below her navel. She looked into my eyes and smiled up at me as I did, my fingertips making only grazing contact with the smooth surface of her skin. When we started kissing again, I slowly curled my fingers several times so that my fingertips drew little lines on her soft flesh before finally beginning to move my hand. I kept my touch to the area bounded by her sternum and a couple of inches above her mons, and her sides — at least, at first. When she didn't exhibit any anxiety or nervousness, I gradually expanded my touch to include her hips and waist, then the outsides and tops of her thighs.
She continued returning my kisses with enthusiasm, and even began using her hand to touch and caress my body; with that to let me know she was still comfortable with what I was doing, I began easing my touch closer and closer to the mounds of her developing mammaries at the top, and more and more toward the insides of her thighs at the bottom of my reach.
My caresses had reached perhaps halfway between the top and insides of her thighs when she surprised me by spreading her legs so that I could reach their inner surfaces. With that to encourage me, I finally made contact with one of her breasts after softly drawing my hand up her young woman's body. That first touch was simply to cup my hand over the warm mass of her breast. I felt her press it into my hand, and didn't hesitate to investigate it further. Slightly firmer than a fresh marshmallow, it barely filled my cupped hand; it was warm and smooth, and I could feel the small pebble of her nipple pressing into the palm of my hand. As I tenderly squeezed and mapped its surface with my fingertips, Emma's kisses slowly began to reveal the arousal and desire that she was starting to feel.
Though I was spending no small amount of time trying to memorize the size and feel of her bust, I didn't neglect the lower areas I'd been granted access to; I continued to draw my fingertips down her body so that I could take pleasure in the silken feel of the insides of her thighs, and the soft smoothness of her skin.
The increasing intensity of our kisses and the feel of my hand on her body finally got her panting hard enough that we couldn't really kiss. That was okay with me, since it meant that there wasn't any reason that I couldn't or shouldn't move my head down so I could use my mouth and tongue in place of my hand and fingers. Emma was a bit disappointed when I stopped kissing her, but when I fastened my lips on the peak of one of her breasts, she released a pleased gasp.
My first considered action was to use my lips to do what I'd done with my fingertips — try to map every bit of surface I could get them on. In the process of doing that, I also applied a few tender nibbles with my lips, and touched the tip of my tongue to her soft skin. Then I went back to fastening my lips over random sections of her breasts and softly sucking on them briefly before moving on to do the same somewhere else. I deliberately chose not to do that to all of her areolas, however; instead, I made her even more aware of what I was doing by taking roughly half of each into my mouth — and it was hit-or-miss as to whether I included her nipples each time.
Even as I was orally assaulting her breasts, I was shifting the attention I was paying her with my hand lower. The soft strokes I applied to the insides of her thighs always started near her knees — but gradually ended closer and closer farther and farther up. When the end of one caress let me gently brush her mons with the side of my hand, Emma released a soft moan as she slightly lifted her pelvis up. Still, I maintained my gradual approach; it was another couple of minutes before I finally cupped her mons in my hand, laying my finger along the cleft of her sex.
I was careful to take my time as I drew the tip of my finger upwards, giving her time to express any objections she might have. There were none, and I was able to slip my finger between the folds of her mound and softly draw it across her opening before easing upwards. Her clitoris was starting to make an appearance from beneath its protective covering, and she moaned her pleasure when I slowly twirled my finger around that small nubbin of flesh.
It took only a couple of passes like that before I was able to start collecting some of the lubrication that she was making in increasing quantity. Once I'd gotten enough of them transferred, and was sure I wouldn't cause her any pain or discomfort, I patiently began to apply different kinds of stimulation to see what I could do that would arouse and please her the most. It took several minutes before I began to get a feel (no pun intended) for what worked best on her.
As I refined my efforts, they began to have more and more of an effect on her, and her passion and desire increased proportionally. When I lifted my head for a moment to look at her, I could see that she had gotten aroused enough to develop a faint blush. I was feeling somewhat pleased with myself when I went back to trying to see how long and hard I could get her nipples…
As I was tending to her clitoris, I continued to make frequent side trips to collect some of her oils to keep things comfortable for her. Careful to never press against it, I still drew my fingertip across the entrance to her vagina; each time I did, she would moan softly, and lift her hips a bit.
I wasn't disappointed or bothered by the time I was spending with her — as far as I was concerned, it simply meant that I got to keep my hands and mouth on her that much longer. Still, I could tell that what I was doing was having the desired effect; it wasn't all that long before I knew that her increasing arousal was reaching the point that she'd find the kind of pleasure she didn't know existed.
She'd been moaning and slowly wriggling under my ministrations for several minutes when I felt her body begin to tense up. Having an idea of how close she was, I maintained the pace of my finger on and around her clitoris — but increased my efforts at her breasts by sucking a little harder on her nipples, and even gently biting them with my teeth. After just a few seconds of that, she practically convulsed with the force of the first spasm of her first-ever orgasm.
Her clitoris quickly took shelter under its cloak, but I continued applying gentle pressure in a circular motion around it as I released her nipple from my mouth. Raising my head, I looked down at her and watched as a progressively milder series of spasms coursed through her young body — leaving her weak and gasping when the last of them had faded. Drawing my hand from between her thighs, I lay down and pulled her into my arms, holding her as she panted for the oxygen her body was demanding.
A couple of minutes went by before I heard her quietly say "I never… I didn't know… that was… wow!"
Giving her a soft hug, I answered "Now you know why nobody can describe what it's like."
"I guess!", she softly exclaimed.
A minute or so later, she asked "Is… is it like that every time? Or was that something special because it was the first one?"
I couldn't help laugh for a moment before telling her "You'll remember it better because it was the first one. As to whether it's like that every time… that's up to you. That's part of what I meant about you making it special to be with someone — if you're with somebody because you like them, or love them, and that's how they feel about you, too… yeah, it can feel like that. I even think that it should feel like that, or else why bother?"
After a few seconds, she wanted to know "Do you think I can feel like that by myself now?"
"I think so. From what I understand, the first time is kind of the hardest because your body doesn't know how to have an orgasm. Once you have the first one, it gets easier and easier for you to have them. And giving them to yourself makes it easier for you to have one when you're with someone else, so there really isn't any reason you can't have however many of them you like
— at least, as long as that's not all you want to do. Of course, if you have trouble, or just want to, I can help you some more, too."
That last part drew a small laugh from her before she told me "I'd like that. You can do stuff I can't do, like licking and sucking on my boobs, and it felt really good when you were doing that.
When I heard about that, I thought it sounded nice, but I didn't know it could feel that good. I guess you like doing that, huh? Even though my boobs aren't so big?"
"Em, dear, I told you before — I think your boobs are just fine; I like them a lot. So yes, I like doing that. And the other stuff I was doing, too, in fact."
"You like touching me like that? Why?"
"Yes, I like touching you that way. And kissing you, and sucking on your boobs. Why? I'm not sure I can really explain it all the way. Part of it is because of how pretty you are. Some of it is just because you're a girl, and I can see what you're going to look like when you get older. More than a little bit of it is because of how I feel about you — the loving you, like I told you about.
The rest of it… it's just that I've always thought that girls your age were pretty and sexy, and it's nice being able to help you learn about sex."
Almost immediately, she had to know "You really think I'm pretty, and sexy?"
After another brief hug, I told her "Yes, I really do. Gail, too."
"But… why? We don't hardly have any hair, and older women have way bigger chests!"
"I know. I think that's part of it, actually. From what I've read, and hearing other guys talk, I think it's pretty common for guys to have the dream or fantasy of teaching a young woman about sex, and making love. For most guys, they think about girls that are a little older than you and Gail.