Even though Sis and I had made love that way a few times (at her request), I wasn't anywhere NEAR ready for Jade to ask me to do the same thing to her.
Seeing how apprehensive Jade was getting, I pulled my thoughts together and told her "Jade, I*do* love you, and all the things that we do together IS making love. You don't have to do that for me to love you."
"I know that, Danny. It's something I want to do – for*me*. There's a lot of stuff about being part Chinese that I like -" I really do. But this whole virginity thing isn't part of that, and I can't get away from that. But if you'll make love with me the way I asked, it's a way for me to get around it -" I'll be able to make love with you, like I want, but stay a virgin like my mom wants."
While Nadia sat there looking like she was still trying to get her mind wrapped around the idea of what Jade had asked, I looked over at Sis. Without having to say a word, I was able to ask her to help.
Jade turned to look at Sis when she began to say "Jade, I understand why you're asking Danny to do that – I really do. Before I gave him my virginity, I asked him to do it to me, too." Nadia looked dumbfounded at hearing that as Sis went on "Both of us know that Danny would be as patient and careful as you could ever want, and that you'd probably be okay with it. But what it sounds like to me is that you want to be able to make love with him that way more than just the one time. Have you really thought about what it might be like if that happens?"
That wasn't quite the kind of help I'd wanted Sis to give, and listened closely as Jade answered "Of course I have. I know that it might be okay the first time, and maybe even a few times after that; but that I *might* decide I don't like it. Except that I know that even if I only wanted him to do it the first time, it would be okay -" I know he wouldn't expect to do that to me every time, and that if I told him I didn't like it as much as I thought I would, he'd understand and not be mad or anything. Like I said, I really have thought about this, and I'm sure that I want to at least try it. If it isn't as good as I think it'd be, then we don't have to do it again; but I'm almost positive that I will like it – I *like* the idea of having Danny in me there."
When Sis turned her head to look at me, she gave me the tiniest of nods, letting me know that she thought I should do what Jade wanted.
I'm not going to deny that the idea of having my cock between the cheeks of Jade's ass didn't have a definite appeal; it was the 'what happens after' that concerned me. All three of them sat quietly (though Jade was far more attentive) as I rolled her request around in my mind. When I finally got things worked out, I looked into Jade's eyes and told her "If you're THAT sure you want to, then I'll agree to at least try. But dammit, Jade, don't let me hurt you just because you want this too bad!"
Solemnly, Jade answered "I promise, Danny, I won't. If it hurts too much or doesn't feel good or anything about it doesn't seem right, I'll tell you."
I wasn't too happy about that 'hurts too much' bit, but had to figure that Jade had enough sense to decide how much discomfort she was willing to accept to get what she wanted.
Sis spoke next, asking Jade "You said you'd like help from me and Nadia. What can we do?"
I could see that relief and a trace of embarrassment on Jade's face as she answered "I – um – I get excited when I think about Danny doing that, but I'd like it if one of you could maybe help me get more excited. You know, to help make it easier. And I, uh, brought some baby oil -" it's in my purse -"
Nadia spoke first, saying "I'd like to help you, Jade", leaving Sis to smile and say "I'll get the oil, then."
By the time Sis got back, Nadia was stretched out on the blanket with Jade, the two of them already tonguing each other's slits. When Jade realized that Sis was back with the oil, she raised herself so that she was kneeling -" but still low enough that Nadia was able to continue her oral efforts. Jade accepted the oil from Sis, then said "Danny, if you'll stand in front of me, I can get you hard and put the oil on you. Then you can put it on me, and we can, uh, try to – you know, see if your penis will go in me okay."
I didn't bother saying anything; I just got up and moved as Jade had suggested. Sis moved to kneel behind Jade and reached under Jade's arms to begin playing with her tits while she started kissing Jade's shoulders and neck.
As I stood in front of Jade, I couldn't help but watch as she used her greatly improved fellatio skills to get me erect. Watching as her lips slid up and down my manhood while her tongue was busy massaging the underside helped get me going tremendously. When she was satisfied that I was not only hard, but likely to stay that way for some time, Jade pulled her warm mouth off of me. After squirting a generous dollop of the baby oil into her hand, she quickly began to apply it to my erection -" making sure that there was sufficient oil on all of it. When she was done, she wiped the surplus off on her belly before looking up at me, handing me the oil, and saying "Thank you, Danny. I really DO want to do this."
I squatted down long enough to give her a kiss, then started to move behind Jade. Sis quickly moved out of the way, and then went on to help Jade move to her hands and knees again. That accomplished, Sis straddled Nadia so that she was right in front of Jade before reaching out to gently hold Jade's ass cheeks apart for me. Looking down, I could see that Jade's small labia were darker and thicker than usual because of her arousal about what I was getting ready to do to her. Nadia was able to look up at me, and I could see that she was eagerly anticipating the show she was about to witness. Moving my eyes up, I found the crinkled sphincter of Jade's anus seeming to wink at me.
After getting a healthy puddle of baby oil in my palm, I set my hand at the top of the crack of Jade's ass and carefully poured the oil out so that it would run down to her pucker. When my hand was empty, I gently and patiently made sure the oil was well distributed before beginning to carefully work it into, then through, Jade's rectum. I heard her breathing pick up while I was doing that, and it began to settle into my mind that Jade might actually enjoy having my stiff dick in her ass.
With Jade and I both lubricated, the only thing left was to see if she was comfortable about having me sodomize her. I got the head of my cock against the ring of Jade's anus, and carefully applied just enough pressure to make sure she knew I wasn't trying to enter her yet. When I put one hand on Jade's hip, Sis stopped hold her cheeks apart and moved back a little before reaching underneath her friend -" apparently so she could start playing with Jade's breasts again, from the soft sound Jade released.
Holding myself in place, I told Jade "You can feel that I'm ready to try this. I'm going to push against you, but I'm*not* going to force my way in -" it's going to be up to you to let me in, if this is what you want to do. I'll stop, or back up, or do whatever you want me to, for as long as you say. Jade, I don't want to hurt you, so if you really love me, don't let me, dammit."
In return, I heard Jade tell me "Please, Danny – I want this."
Sighing internally, I began to push the head of my penis against her most intimate opening -" gently at first, and then slowly increasing the pressure. As I did, I could feel Jade's sphincter clench a little, then relax; it took a bit before I realized that there was more relaxing than clenching going on. Only then was I really sure about how serious she was about what I was trying to do, and I was more willing to increase the pressure I was applying. It didn't take long (from my perspective, anyway; Jade's may have been different) for me to feel the tight ring of her nether opening begin to expand. At that point, I chanced a look around and saw that Sis had lowered her head and was softly talking to Jade, offering words of encouragement and support, I figured. Both of Jade's hands were fists, clenched around small folds in the blanket we were all on. When I looked to where Sis was talking to Jade again, she saw me looking at them and gave me a small nod to let me know it was okay to continue.
I'd started to press myself into her again when I heard Jade tell me "Danny, I know you don't want to hurt me, but I really do need you to push a little harder. I promise, if you start to go too fast or hurt me, I'll tell you."
Hearing that, I was willing to increase my efforts, and began to steadily increase the pressure of my penis against her. I could see and feel it as more and more of the head of my cock disappeared in her pucker. We managed slow but steady progress, and when the last of the head of my cock popped into her, I was able to stop and hold myself still in her even before she was able to give voice to the small squeak she made.
After moving my hand from my penis to her hip, I asked Jade "Are you okay? What do you need me to do?"
It took a couple of seconds before I heard her answer "I'm fine -really. Holding still like that is good -" you felt a lot bigger than I thought you would, and I was surprised when you suddenly slid into me that last bit, is all. God! You feel*huge* in me – but I – I like it, too."
Beneath us, I heard Nadia say "I'll say! I've never seen you this juicy before, so I sure like it!"
Even from where I was, I could see how furious Jade's blush was, and how hard Sis had to fight the urge to laugh. A few seconds later, Janet told her friend "Nadia, dear – that wasn't something that all of us needed to hear. And you didn't have to be quite that enthusiastic about it, either", as though she were explaining the finer points of high etiquette to a wayward student.
In what I could tell was pretend innocence, Nadia answered "Well, I just wanted to make sure Danny knew she wasn't fibbing, or anything."
I knew Jade wasn't upset when I heard her say "I swear, Nadia, if you ever let him do this to you while I'm around, I'm going to announce *everything* that happens with you using one of those bullhorn things!" Below me, I heard Nadia's soft chuckle.
I could see that Sis was still doing whatever it was to Jade's breasts, so I began softly stroking her sides and back to help her relax as I waited for her to tell me she was ready for me to continue. It also distracted me a little bit from the way her anus was almost painfully clamped around my cock, and how hot her bowels felt.
Only a few minutes passed before Jade let me know that she was ready to continue by pressing herself back against me. Getting my hands on her hips again, I held her steady while I slowly pushed the rest of my oiled erection into her as she began to moan her pleasure at what she was feeling. It didn't take long before my pubic hair was wedged into the crack of her ass and her rectum was clenched around the base of my penis. I held myself still in her again, giving her the time to get used to having me buried in her so intimately. It was only a few seconds before she quietly announced "God, it feels*so* weird, having you in me like that, Danny -" but it feels so good, too. The rest of you was a lot easier than the first part, and it was really nice that you were so slow about it. If you're ready to start moving in me, I'd like that -"
Hearing that she'd liked it when I moved slowly, I was careful to take my time about easing myself back out of Jade's tight ass; when only the head was still inside her, I just as slowly got myself embedded in her again. As I continued to slide myself back and forth through her tight ring, I patiently and gradually increased the speed of my strokes so that she would have plenty of time to let me know if I started to cause her any discomfort.
I felt Nadia start to move beneath me, and saw Sis shift her body so that it was easier for Nadia to slide herself out from under Jade. When she was clear, Nadia quickly got herself repositioned so that she was oriented the same way Jade was, but with her head even with Jade's breasts -" which she eagerly began to suck on. A moment later, I felt my balls brushing against her fingers as she began teasing Jade's clitoris.
Jade had started pushing herself back at me when I got into a particular rhythm, so I was content to maintain that pace when Sis shifted herself so that she was sitting cross-legged – making it possible for her and Jade to start kissing each other more easily. That and the attentions she was receiving from Nadia contributed to the increased presence of Jade's unique aroma in the air as she got more and more aroused -" and more and more vocal about the pleasure she was experiencing. The others teased her about it because it was so true; Jade's moans, gasps, groans, verbal encouragements and exclamations all increased dramatically as her excitement increased. Sis had once observed that she wondered how Jade managed when she wanted to masturbate at home – My own pleasure was increasing, as well. When I looked down to where Jade and I were joined, I was fascinated by the way her anus would try to follow my penis: pulling out slightly when I withdrew from her, then disappear as though guiding my penis into her bowels when I reversed direction. Each time my balls came in contact with her mons, I could feel the heat coming from her vagina, and some of the overflow of her oils would be transferred to them. Sometimes, Nadia would extend her fingers so that my scrotum would drag along them, too.
I continued to piston myself in and out of Jade's hot and tight back channel in the rhythm that she so obviously found pleasing; as the seconds continued to tick by, her arousal (and my own) increased steadily. To my surprise, Jade's arousal was even happening at something close to a normal rate for her, due in large part to the added stimulation being provided by Nadia and Sis. Of course, their interest was in making sure Jade was okay; that I was benefiting from it, too, was an added bonus.
From the sounds she was making, I knew as Jade got closer and closer to having an orgasm -" and was starting to look forward to it. The physical sensations of sliding my oiled cock into her bowels was pretty damn good; *knowing* that that was where my penis was _at her request_ fueled my pleasure even more. I could feel myself approaching my own release, and wasn't all that sure that I could hold off on my own climax until Jade had hers.
As it turned out, I couldn't. Despite knowing that Jade couldn't be but a couple of seconds from having an orgasm, I couldn't push my climax back any longer; I barely managed to get as much of my stiff dick into her as I could before I felt myself begin to spray her insides with my cum.
Even as my cock tensed to fire the second salvo of my semen, Jade cried out "I can feel it! He's squirting, and it's so hot!", quickly followed by a spasm coursing through her body as she found her release.
Jade's already-tight anus got even tighter around me as her vaginal muscles began a cyclic clenching that felt like a rippling sensation along the underside of my penis, and stimulated me into emptying myself into her even harder as I groaned my pleasure.
It was actually something of a relief when my cock stopped trying to fill her with cum that wasn't available, and I was able to rescue my rapidly-softening penis from her nether clutches. The tightness of her anus made sure that the last few drops of my semen were milked out of me as I eased my hips back. Despite having found MY pleasure, I wasn't about to abandon Jade -" far from it, in fact. Leaning forward, I was able to support myself with one arm (Nadia's position kept me from using both) so that my front was in contact with Jade's back. I got my free arm around her, and began softly stroking her belly and abdomen while kissing her shoulders as she shuddered occasionally with the end of her climax.
It had obviously been a powerful release for her, so I don't think that Sis or I either one were surprised when Jade's arms suddenly gave out; with me supporting most of Jade's weight, Sis told Nadia that we needed to get Jade down onto the bed. Nadia hurriedly got herself out of the way, and Sis provided the fine control we needed as I carefully got Jade lowered onto her stomach. Sis softly said something to Nadia, who quickly headed for someplace out of sight. I got myself onto my side next to Jade, where she could see me. Though she looked more than a little stunned, she was able to smile at me when I pursed my lips in a kissing gesture before putting my arm across her back. We stayed like that for a couple of minutes before I saw Jade's eyes widen; a moment later, Sis told me "You don't have to let go of her, Danny, but if you can turn your hips, I can get most of the oil off of you."
I did as she said, and when I felt a warm washcloth being used to wipe off my pelvis, knew that Nadia was performing a similar service (if in a different location) for Jade.
Jade's breathing was still a little rapid when she softly told me "Thank you, Danny. That was wonderful. Even if Nadia and Janet hadn't been helping me feel good, I think I would have had an orgasm from that."
I was able to move enough to give her a soft kiss on the cheek before I answered "I'm glad you liked it."
It was easy to see that my kiss meant a lot to her, so I did it again before going back to laying next to her. When I used my fingers to caress her side, she released a happy and contented sigh.
After a few minutes of the two of us just laying there, both of us felt like seeing if we could move -" and maybe even sitting up.
Nadia and Sis were happy to provide the assistance we needed to actually get vertical, and that was when I saw that Nadia or Sis had put together a collection of sodas and munchies -" hopefully for all of us, I thought as I looked at it.
I was close enough to the couch that I was able to use it as a back support; Jade sat next to me and leaned against my side with my arm around her. Sis and Nadia handed us the items we requested from the goodie tray, and waited patiently until we'd refreshed our fluid and energy levels a bit before trying to get us talking.