To say that I was unprepared for something like that would be a massive understatement. I'd thought that maybe she needed help picking out a gift for Eva, or something equally simple. But to be the first guy she was ever with? From listening to Eva and other girls, I had a pretty good idea of how important that first time was to a girl — and there I was with Charlene sitting on my bed, asking me if I could and would be the one to deflower her.
I think she must have been able to see how surprised I was by her request, because she waited quietly the couple of minutes it took before I was able to respond.
"Charlene, are you sure you want to do that? And with me? Why not wait until you do find the guy that can accept you for who you are?", I asked.
"Yes, I really am sure that I'm ready to stop being a virgin. The doctor told me that I don't have a hymen, so you wouldn't be getting a cherry, but it would still be the first time I ever actually had sex with a guy. And I'm absolutely positive that I want it to be with you, for a couple of reasons, and not wait until later."
I just had to ask "What reasons?"
"The most important one is that you already know about me, and you're okay with it: that I've got a penis, and how my vagina isn't full-sized, and all that. I know that you'd know to be patient and gentle and understanding with me, and that if it couldn't happen for some reason, you wouldn't be mad or upset. The other part is that because of how nice you've been and how much you've done for me — not just the physical things, but the rest of it, too — I want you to have something as special as what you've given me; you've let me have so much from your heart that I want to give you something from mine. I don't mean for it to sound like I'm trying to, like, trade what I want for what you want, either; you gave me part of yourself because you cared, and that's what I want to do in return."
Her answer settled my mind about the why, but there were another couple of things that I figured I had to know before I could really give her an answer: "Okay, you're sure about it. Would we, um, need anything? And is this something you want to happen just once, or what?"
I was surprised at the pleased grin she showed me before answering "No, we don't need anything. A few months ago, I asked my mom about birth control. She said she'd make an appointment for me and sign whatever forms were needed if I was underage. Then she told me that she loved me, and that all she was going to say to me was to be careful and make sure. I said I would, and that's all there was to it.
When I went to the doctor, he put me on birth control pills and told me that they might help — that I'd always be a hermaphrodite, but that the hormones and things in the pills could help keep my penis from growing along with the rest of me. It wasn't a sure thing, though, because they just don't have enough experience with that kind of stuff with herms. I've been using them for a couple of months now, so I'm as protected as I'll ever be. As for the other… if it goes as nice as I think it will, I hope that it won't be just the one time; but it won't be, like, all the time, either. If you've got something going on with someone else, I wouldn't bother you with it, but if both of us want to… yeah."
Like any guy that age, I'd had dreams and fantasies about having sex, and wondered if it was ever going to happen. The idea of actually being offered the chance to lose my virginity was something that I'd never even considered — never mind the possibility of it happening with someone that wasn't quite entirely female. So despite the ease of my initial questions for Charlene, I still had to think about what she'd asked of me. I'm sure she realized it, too, since she sat quietly and (mostly) patiently while I thought. To my surprise and relief, the things that I'd already done with her and Sis made the purely physical part of the problem moot for the most part; "all" that I was left to deal with was the nonphysical aspects of it. Having turned 16 just a couple of months before, it was a lot for me to deal with — and it took me several minutes to get it all worked out in my head as Charlene fidgeted every so often.
After taking a little more time to get my thoughts organized and figure out how to tell her what I'd settled on, I told her "You know that I wasn't anywhere near being ready to hear something like that from you, and I appreciate your patience while I figured things out."
She nodded, and I went on to say "I know that this means a lot to you; I don't know if you understand that it's a big deal for me, too."
In response to the surprised look on her face, I explained "Yeah, most guys would jump at the chance to have sex — with any girl, any time, any where. But you should remember that you've told me that I'm not like most guys. Sure, I want to start having sex, too- but because of what you and Sis and I have done, and how we got started, I want MY first time with a girl to mean something, too- and for her to be someone special to me. I mean, if all I wanted was to get laid, I could probably take Lisa Ann" — she was known to be willing to do anything with anyone, having been caught in flagrante delicto several times — "out some night. But I want more than that. Not just for the first time itself, but afterwards, too: I want to spend the rest of my life remembering not just the act, but the other person and how we were with each other later. I want to remember it with happiness and pride, not sorrow and regret. You understand?"
"Yeah, I do, Billy", she replied.
After a deep breath, I went on "I also had to think about what you and me would do to us — you and me, you and Sis, Sis and me, and all of us together. And on top of that, how it might affect us at school
— and afterwards. Then on top of all that, there's the fact that you are a hermaphrodite: because you're different, whatever happened between us would be different, and maybe change everything that followed to some degree, too. It was a lot for me to consider, and I wanted to make absolutely sure before I gave you an answer."
As I finished, I could see that Charlenes expression had changed; it took me a moment to realize that she was preparing herself to be disappointed. I didn't delay in telling her "But I am sure that I'd be delighted and honored to be the one that you give yourself to the first time."
It took her a second to actually understand that I was agreeing to her request, and not turning her down; her face went from resignation to delight in the tiniest fraction of a second before she exclaimed
"Really? You will?"
I couldn't help laughing for a moment before answering "Yes, really, I will."
When I opened my arms in invitation for her to sit on my lap, she didn't hesitate a moment to do so.
With my arms gently wrapped around her, I said "I've told you before: you're a smart, pretty, and nice girl. You're the kind of girl that any guy is going to like — a lot. The hard part is dealing with how you're different. It's not something that bothers me, and I'm sure you can figure out how to find out whether or not another guy will be okay with it, later. What matters now is that I love you. Not like I think we should run off and get married, but enough that I care enough about you to want to make you happy. And I think that you feel the same way about me enough" — "I do!" she declared — "that I really do think us having our first time together is something that I'll be glad to remember. I'm going to do my very best to make it something that you'll be happy about, too. To do that, I'm going to need your help, though. The last thing I want to do is rush you or hurt you or make you uncomfortable about any of this; so what I want and need is for you to talk to me, and let me know when I start to get things wrong. That doesn't mean we'll have to stop, or anything, only that we'll do things differently, okay?"
"I know you wouldn't do anything like that on purpose, Billy- that's part of why I wanted my first time to be with you. But if something isn't right, then I promise: I'll let you know", she answered with a smile.
I followed up by asking another question: "I'm trusting we don't need to worry about being interrupted?"
"No, we don't. Eva knows I'm in here, but not exactly why — all I told her was that I wanted to find out about something… physical with you, but that I'd be embarrassed if she was there. She said she understood, and she'd just wait until I got back."
With that, there was nothing for me to do but move my head in and give her a soft kiss on the lips. She readily returned it, and when it broke several seconds later, we were well on our way toward getting on the same wavelength. Several more kisses followed, each a bit longer and more "involved" than the one before; when the last one finished, it was plain as could be that both of us were ready to get things moving.
When our lips met again, I moved my hand so that it was gently resting on her waist; she was the one to move it to her bust before softly squeezing it to let me know she wanted me to do more than just hold it there. I certainly didn't have any problem with that, and it took me only a few seconds to conclude that she didn't have a bra on under the light dress she was wearing. As our kiss waxed and waned, that conclusion was confirmed as I patiently and tenderly re-explored both of her mammaries with my hand and brought her delightfully long nipples to erection.
Our lips separated, and there was no mistaking the smokey look in Charlenes eyes: she, too, was ready for us to move things along. It took only the lightest of nudges to her back to get her to stand up; I followed her example before moving behind her. There, I didn't delay in beginning to undo the buttons that ran down her back. Once they were all unfastened, I slowly eased my hands between the cloth and her skin, then slid them around and cupped her breasts before running my thumbs across the hard cylinders that had dented the fabric of her dress. In response, Charlene released a soft moan and leaned back against me. Several seconds later, she reached around and began rubbing her hand along the length of my inflating penis. That was the cue for me begin sliding one of my hands down her body (and discovering that she didn't have any panties on, either) toward her pelvis; there I found her extended clitoris was half-erect; I gave it a few soft tweaks before continuing onward. Between her smooth thighs, the entrance to her vagina was already beginning to leak her liquid arousal.
After toying with her opening for a bit, the end of my finger was well-wetted with her essence. That was all I needed to move my hand back up so I could take the shaft of her pseudo-penis between a couple of fingers and begin applying her own oils to its end. That was enough to draw an impassioned moan from her, followed by her extra appendage getting even stiffer under my ministrations.
After only a couple of minutes, Charlene managed to pull herself together enough to tell me "Billy, you're making me feel real good — but it isn't what I came in here for."
Reluctantly, I released my hold on Charlenes extended clitoris in favor of giving both her breasts a last gentle squeeze before easing my hands out from under her dress. Nuzzling her hair out of the way, I gave the back of her neck a soft kiss as I slid the shoulders of her dress down her arms. Not only didn't she make the slightest effort to prevent her dress from forming a puddle of cloth around her feet, she added to the mound of fabric by slipping her feet out of the sandals she had on — leaving her standing there stark naked in front of me. I had time to put my hands on her waist and give her bare shoulder a soft kiss before she moved forward a couple of steps, then turned around. The first thing I did was to look into her eyes, where I saw the smoldering desire she was feeling. From there, it was on to look at her whole face, then the rest of her… including the semi-stiff finger of flesh protruding from the dark curls of her pubic thatch. When I moved my gaze back up again, I could see that she needed a little reassurance; I didn't have the slightest hesitation about telling her "You're even prettier than I thought you were the first time I saw you. I know just how lucky I am to see you like this, and I'll always appreciate all the things that we've done together. I really do consider it an honor that you'd choose me as the first guy you're ever with, and I'll do my very best to deserve it."
That earned me a pleased and relieved smile from her before she told me "Thank you. Now it's time for me to get you naked!"
Feigning a reluctance I certainly didn't feel, I answered "Well, I guess that'd be okay…" — something that drew a soft laugh from her before she took a step toward me and reached for the collar of the shirt I had on.
It took appreciably longer for Charlene to rid me of my shirt than I'd needed to get her out of her dress; that was due to the fact that every time she got a button undone, she'd use the opportunity to kiss the newly-exposed skin and reach inside to caress however much of my chest and abdomen as she could easily reach. Even so, there came the point that I was as bare above the waist (if somewhat less appealing) as she was. The delight and anticipation she felt were plain as could be as she moved her hands to the buckle of my belt…
It took her much less time to get my pants unfastened and down around my ankles — what she was so patently interested in was forming a not-insignificant bulge in the shorts underneath. She paused a few seconds to simply look at my crotch before reached up to slide her thumbs under the waistband of my briefs; slowly, obviously teasing herself, she began to move her hands down. As she did, I took the opportunity to slide my feet out of the slippers I had on before I was hobbled by my own underwear. I was barefoot and looking down at her when she finally got my shorts pulled down far enough that my semi-erect cock popped free… something that drew a soft gasp from her, even though she already knew what it looked like. Once my balls became visible, it was a matter of but a couple of seconds before my underwear was resting on my pants.
With her eyes locked on my manhood, Charlene slowly slid her hands up my legs; as she brought her hands up, I felt her fingers softly press against my skin and muscles every so often as though she was trying to memorize the feel of me.
When her hands finally came together, it was so that she could cup my entire package in them. The way she was looking at my works was almost worshipful for the several seconds that went by before she slowly leaned forward and tenderly kissed the head of my penis. After she'd done that, she tilted her head back to look up at me and say "The things we've already done… to and with each other… I've already gotten so much pleasure from this. And now I get to find out what it feels like when it's inside me, where I want it!"
With that declaration, she tilted her head back down before leaning forward enough to take the head of my cock between her lips. A moment more, and she began to use her tongue and a gentle, rhythmic suction to start moving me toward full erection.
The next few minutes were a delight for me as she used everything she'd learned about pleasuring me, only amplified by her desire to have me filling her womanhood coupled with her enthusiasm to make it happen. As my manhood grew longer and harder, she took more and more of it into her mouth so she could stimulate me even more. By the time she let me slip from her oral embrace, I was almost achingly erect — and more than ready to try and satisfy her need to feel me inside her virginal chamber.
Satisfied with her handiwork (well after I was!), Charlene stood up. Taking me by the upper arms, she got us turned around before backing us toward my bed. When she felt it against the backs of her legs, she released her soft hold on me and sat down followed by scooting herself to the center and laying down. After bringing her knees up and spreading her legs, she told me "I'm ready, Billy. More than ready, even!"
Thinking that she just meant she was ready for me to get her going, I got onto the bed, too, and knee-walked my way to where she was. Looking down at her, I couldn't help but notice that she was a lot more ready than I'd thought: not only was the shaft supporting her clitoris standing straight out, the entrance to her womanhood below it was readily visible and clearly glistening with her female dew.
There was no mistaking the fact that she didn't need any help from me on "getting going" — she was obviously already there!
Even with Charlene clearly ready to have me try deflowering her, there was something I wanted to do: lean down and run my tongue across the entrance to her vagina so I could collect a goodly taste of her essence. Once I'd treated my taste buds to her nectar, I continued onward to position myself so that we could give each other our virginity.
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.