"That's fine, Em. If you want the lights on, then go ahead."
She moved away from me, and I felt her get out of bed; a few moments later, the lights were on, and I got to watch as she got herself settled next to me again. She didn't bother to pull the bedcovers over us before hesitantly telling me "I… I've read and heard about some of the things that two people can do together, and… and I want to try them at least a little bit so I can find out if I'd like them."
"What kind of things?"
"I, uh, I'd like to, um, use my mouth on you-you know, your penis-if you don't mind. And I'd really appreciate it if you could maybe do that to me, too, so I can find out if it's different when a guy does it."
I caught that "different when a guy does it", and couldn't help thinking that she'd already had some experience being on the receiving end of cunnilingus, and figured I knew who'd done the honors. I also had a pretty strong suspicion that it hadn't been a one-way transaction, either. But the prospect of getting my head between her thighs was all I needed to answer "I'm okay with both of those."
Her last request was "When it's time… you know, for you to be inside me… would it be okay if I was on my back and you were on top of me? I really do want it to happen; I'm just not sure I could be brave enough to break my own hymen, is all."
"If that's what you want, then that's what'll happen, Em", I assured her.
Satisfied that the high points had been taken care of, she moved on top of me, straddling my waist while supporting her torso with her arms. As I looked up at her, she told me "I think this is probably the last thing you'd ever think of the two of us doing, Uncle Dave, and I don't think it can be easy for you. But I really am ready to find out what it's like to be with someone like this, so I need you to understand that I want you to touch me: my boobs, and my butt, and between my legs, and anyplace else that you would with a girl you were intimate with. I want you to kiss me like you mean it- not just on my cheek or my forehead like you always have, but my mouth and the rest of me, if that's what you want. I want you to do whatever you want to, and can, to show me how good it can be when two people are together like this. Uncle Dave, this is my first time, and I want you to help me make it good so all the times after this will be good, too. I know it's a lot to ask, but can you do that for me?"
From the grades she got in school, all of us knew she was more intelligent than most her age; hearing that from her reminded me that she was also a hell of a lot smarter, too. All I could do was look into her eyes as I answered "I'll do my best, Em. That's all I can promise."
That earned me a smile before she told me "That's enough, Uncle Dave. Now, do you think you could start by kissing me and maybe playing with my boobs a little bit?", the last with an impish grin.
I raised my head, and Emma lowered hers, so the two of us could kiss-as first-time lovers. It started soft and chaste, but didn't remain that way for long as Emma told me through her lips how much she loved me… and then how much she wanted me. I didn't have the slightest hesitation about doing my best to let her know that I loved her, too; but it took a bit longer before I could let go enough to even start to return the desire she was offering me. Once I began responding to the touch and feelings coming to me through my lips, and set aside who those lips were attached to, it got easier and easier.
When I felt her tongue brush across my lips, I was more than willing to open my mouth and let my tongue go out to make friends with hers; it wasn't but a few seconds before they were enthusiastically wrestling with each other, moving back and forth between our mouths. Without realizing I was doing it, I moved my hands to her waist and began caressing her soft, smooth skin; as our tongues continued to duel and our breathing quickened, I expanded my touch to include as much of her as I could reach. When I got my hands on the rounded firmness of her ass, all I could do for the next little while was gently squeeze and caress those warm globes: delightfully smooth under my touch, they were incredibly firm when I gripped them. I eventually released my hold on her ass in favor of continuing my explorations of her body-but didn't neglect to return frequently and resample the feel of her tight buns under my hands.
The kisses between me and Emma eventually reached the level that both of us were finding it difficult to both kiss AND breathe; by mutual agreement, we decided that breathing had the higher priority and she raised herself up again. Doing so, she made the front part of her body available to me, and I didn't delay in moving my hands to cover the mounds of her breasts… and was immediately glad of her suggestion that I do so.
Each of her orbs neatly filled my hands with their warm sponginess while the hard nubbins of her nipples pressed firmly into my palms. After carefully squeezing them a few times while marveling at how soft yet firm they were, I began exploring their surfaces with my fingertips. Enjoying their smooth warmth, I eventually found my way to their peaks where I discovered that her areolas were puckered and crinkled, and that her nipples had grown a bit longer while remaining deliciously hard. My Braille examination of the most obvious signs of her femininity were enough to encourage the tips of her breasts to even greater growth. When I finally released her lovely mammaries and moved my hands to her back, it took only a slight pressure to get her to lean forward far enough for me to raise my head and fasten my mouth on the dark flesh capping one mound. As I softly sucked on her nipple, I heard Emma release a moan of pleasure as she pressed her chest forward in encouragement for me to continue.
After moving my hands back to her ass, I had a grand time playing with her butt while orally tending to her breasts: licking and sucking on her nipples and other random points, nuzzling and kissing every square millimeter of both mounds, and generally doing whatever I could think of to let her know what I thought of them. I knew my efforts were appreciated from the increasing frequency and volume of the noises Emma made, and the way her nipples grew progressively longer.
My fun was interrupted when Emma sat up, pulling her body out of reach of my mouth and lips; when I looked up at her in question, there was no mistaking the desire in her voice when she told me "I really like that, but I want to do the other stuff, too."
"If you'll turn around and then back up, we can do that to each other at the same time", I responded.
She nodded her understanding/agreement, and it wasn't but a few seconds until I had her knees on each side of my head; a couple more had us in the classic "69" position.
The sensation of her taking my semi-erect cock in her cool hand was easily overwhelmed by the sight she was presenting me: a clear and unimpeded view of her virginal womanhood. Amid the dark vee of her bush, I could easily see that her clitoris had made an appearance at the top of her cleft. Below that, her soft pubic hair was divided by the engorged (but still rather thin) lips that bracketed her vaginal opening. The inner surfaces of her labia glistened, telling me what I'd find as I put my arms around her legs; when I tenderly spread her inner lips, I was privileged to see that she was already wet inside-enough so that there were already several drops of her oils that had escaped, and were waiting for me to collect them. It was also possible for me to make out the ring of her hymen, farther inside; opening her a little more, I tried to see if I could get some idea of how difficult it would be to get past that obstacle. As I was doing that, Emma began slowly and gently stroking my manhood in an effort to encourage it to further growth.
Not being a doctor or having actually seen another maidenhead to compare to, I wasn't qualified to make any absolute judgments about Emma's, of course. Still, I was left with the impression that Emma's hymen looked somewhat fragile, and didn't think (as well as sincerely hoped) that it wouldn't present too great of an obstacle… relatively speaking.
Having accomplished that much, I took a minute to try and memorize the sight of Emma's womanhood; I didn't expect to ever see her quite that way again, and was determined to remember the view I had of her as completely and accurately as I could. Once I was satisfied, I raised my head and extended my tongue to collect my first taste of her nectar; it took only a brief, light pass of my tongue across her opening to gather the drops of her essence that I'd seen. It was only a moment for me to get the full flavor of her: her oils were light and somewhat thin, and were slightly sweet and earthy at the same time. I eagerly applied myself to the pleasant task of encouraging her to produce even more of them by moving the tip of my tongue to the bottom of her opening, the slowly drawing it upwards-pressing slightly against the entrance to her vagina before sliding it between her soft labia and finishing by making a couple of soft laps around the flesh pebble of her exposed clitoris.
Emma responded to the beginning of my action by trying to press her pelvis down to increase the contact with my tongue, and rewarded my efforts to her clitoris by releasing a deep and impassioned groan of pleasure before taking nearly the entire length of my mostly-erect manhood into her mouth. As I continued my activities between her smooth thighs, she got considerably more enthusiastic about using her mouth and tongue to stimulate my penis into even greater hardness; I could almost feel her reluctance to let any part of me escape from between her lips, despite the fact that I was becoming more than she could comfortably hold in her mouth.
It didn't take me long to get her to the point that she was steadily leaking a small amount of her juices for me to lap up between bouts of softly sucking on or gently lip-nibbling her soft labia, or teasing her sensitive clitoris. In return, she seemed quite happy to dedicate herself to learning everything she could about performing fellatio… and doing a damn fine job of it.
She seemed to know what things not to do, which left plenty of room for her to experiment: different amounts and kinds of suction, using her tongue in varying ways at an assortment of places, using her lips in a variety of ways, and any permutation of anything else she could think of. Of course, some of the things she tried were more pleasant than others, but nothing she did hurt or was uncomfortable. The net result was that once I reached a certain point, my arousal increased appreciably slower than hers did-essentially, once she got me hard, she was doing little more than keeping me that way while I was moving her closer and closer to an orgasm. Not only was that just fine with me, but actually a plus as far as I was concerned: I figured that if I could get her to climax first, she'd be well-lubricated inside and relaxed enough to make our first union as easy as possible for her.
All there was for me to do was lay there and enjoy the hell out of the situation: getting a blowjob that varied between "good" and "Hot damn!" while eating her fresh, young pussy.
We continued like that for several minutes as I steadily (and deliberately taking my time) added to her pleasure and arousal, moving her ever closer to having a climax. When I judged that her release couldn't be too far off, I added something else to the mix of things I was doing between her thighs: pressing the tip of my tongue against her opening. The first few times, I just touched the entrance to her vagina with my tongue; her reaction was enough to let me know it was okay to continue, gradually increasing my efforts until I was able to get fairly insistent about it. What with the other things I was doing to and with her, it didn't take a whole lot of that before I could tell she was incredibly close to having an orgasm.
I'd gotten my mouth over her clitoris and was sucking on it in a soft rhythm while circling it with my tongue when Emma suddenly pulled her mouth off my cock. Not even a heartbeat later, I heard her start to cry out with her release, only to have it cut off by her body suddenly seizing up with the first wave of her climax. Wanting her relaxed but not comatose, I left off my attentions to her clit in favor of simply licking up the juices that started leaking out of her-which was apparently enough to prolong her release, anyway. When the last spasm of pleasure had faded, I could hear her draw a deep, ragged breath, followed by her body swaying slightly over mine. Realizing that she'd been left feeling weak, I pulled my head back from her crotch and got my hands shifted to her waist. Understanding that I was ready to help her move, she let me guide her off of me and to a sitting position; from there, it was easy enough to get her laid out next to me so I could get my arms around her.
After a minute or two, she'd gotten her breath back enough to softly tell me "God, that was good."
I continued to hold her and give her occasional soft kisses to her lips or anyplace else that struck my fancy until she was able to tell me "I really liked it when you started using your tongue to try and get inside me, Uncle Dave. I didn't figure you could, but it still felt good when you tried; it kinda gave me an idea of what it would be like when you put your penis in me, and that made me really excited."
My conscience demanded that I ask "You still want me to have your virginity? Or was that enough?"
She immediately declared "That wasn't anywhere near enough, Uncle Dave! If you can make me feel that good just using your tongue, I have to know what it's like when you're inside me, now!"
"Are you ready for us to go on, then?"
I saw her nipples start to erect again as she told me "Oh, yeah!"
When I released my gentle hold on her, she didn't hesitate to roll onto her back and spread her legs; after I sat up and moved between them, she brought her knees up and spread herself for me even more; opening herself to me completely enough that I could easily see her parted labia and how wet the area between them was. Moving over her, I reached between us and levered my hard cock down so I could get the head of it against the entrance to her vagina. Before I could say or do anything else, she wriggled her body down enough to ensure that the end of my manhood was securely wedged against her opening.
After getting myself settled over her, I looked into her eyes and asked "Are you really sure you want us to to do this? You can change your mind now, or any time up until your cherry is gone, and I won't be upset-not even a little bit. All I want is what's right for you."
Of course, I was lying my ass off about it being okay for her to call things off: I'd be disappointed as hell. But it was more important to me that Emma didn't feel like she was in a situation where she felt like she had to do something that she really didn't want to.
It proved to be a moot point, anyway, because she didn't hesitate in the slightest to tell me "Yes, I'm really sure, Uncle Dave. I was already sure before I came in here; what you did with me… that only told me that I picked the right person to give myself to the first time. Please… make me a woman."
Continuing to look into her eyes, I carefully watched for any signs that I was causing her any pain as I began pressing myself into her-feeling her clench and relax as she tried to get control of the tight ring of her opening. Soon, there was a lot more relaxing than clenching happening, and the end of my erect penis began slipping into her a millimeter at a time; there was still enough of her saliva on my cock to supplement her abundance of oils to keep us both well lubricated.
I had roughly half the head of my penis in her when I felt the ring of her maidenhead against the end of my erection. Watching her even more closely, I continued pushing my staff through her opening. While she looked mildly discomforted, there wasn't any indication that she was experiencing anything like outright pain. Finally, I felt the knob of my erection slip all the way into her: she was tightly clenched around me right behind the crown while her surprisingly resilient hymen was pressed against the end. I held myself still in her to see what she wanted me to do, and after a few seconds, she looked up at me to say "That wasn't as easy as I hoped it would be, but nowhere near as bad as I was afraid, either. I guess that's my cherry I feel you pushing against, inside?"
"I expect so", I answered. "What happens next is up to you. I can pull out"-"Don't you dare!" she immediately exclaimed-"or I can keep going. I can either break it, which will probably hurt more, but get it over with quicker… kind of like just pulling a bandaid off all at once. Or I can go slower and see if it'll kind of surrender, which won't hurt as much, but take longer." Grinning down at her, I added "It's your cherry, so you get to decide."
"Oh, thank you too, too much", she answered with a grin of her own. A moment later, she told me "I think I'd like to see if it'll surrender. Just breaking it sounds like it'll definitely hurt no matter what, but if it surrenders, it might not hurt at all."
It wasn't MY hymen, so I was basically fine with either choice for the reasons I'd given her. Still, I'll admit to being relieved that she'd gone with the surrender option for the reasons she'd given.
Lowering my head, I touched my lips to hers and she eagerly kissed me back. It wasn't but a few seconds until our tongues went out to get reintroduced; as our kiss intensified, I began slowly rocking myself back and forth-ever-so-gently at first, and very gradually increasing the force I applied against the impediment to having her wish to become a woman being fulfilled.
I doubt that either of us was prepared for it when her hymen suddenly gave way, allowing nearly an inch of my cock to slide into her accompanied by her soft grunt. I immediately held myself still in her again, and after breaking our kiss, asked if she was all right.
Her tone of voice told me that she was relieved, and not in pain, as she answered "I'm fine. It didn't hurt, exactly, I was just surprised when more of you was in me-I mean, you feel huge, and it was so sudden."
Seeing that I was looking at her closely, she went on to tell me "Really, Uncle Dave-I'm okay. Better than okay, even: I'm not a virgin any more, and it not only didn't hurt, but it's even starting to feel good. So you can keep going any time you want… as long as it's soon, 'cause I really want to feel you all the way inside me, filling me up. Okay?"
It was easy enough to see that she really was "better than okay", so I lowered my head and started kissing her again; our osculations quickly reached their previous levels, and I began doing as she wanted me to: filling her incredibly warm and tight sheath with my manhood. The process went faster and easier than I had any reason to hope for, so it wasn't long before I felt my pelvis pressing against hers with the tight ring of her opening clamped around the base of my cock while the end touched the deepest part of her.
With that milestone reached, our kiss ended so she could look up at me with something akin to awe as she said "I thought it would feel good, having something inside me after feeling so empty there so many times. But I never even dreamed it could feel like this!"
Since Emma appeared to be fine with having my adult male erection buried in her, there didn't seem to be any reason not to start moving it. I was still looking into her face as I slowly arched my hips back, sliding myself out of her, and saw her eyes get wide at the sensation of having my entire length moving in her. Then when I reversed direction and steadily pressed myself into her, she closed her eyes and released an impassioned moan as I filled her with my manhood in a single slow thrust. When my pelvis was touching hers again, she opened her eyes and softly declared "Dear god, that's good. Do it again!"