When I reached the point that I knew if I let her continue, she'd end up with an unexpected surprise, I forced her away from me, though for a moment, she actually fought back as though having no intention to release her lips from me.
"My turn to do you," I said softly.
Jackie and I traded places and she positioned herself comfortably amongst the pillows. Spreading her legs a part with my hands, I glanced down towards her bare pussy, freshly shaved this morning, and wondered briefly if she had known she was preparing herself for this evening together. I lowered myself towards her, immediately catching the fresh intoxicating scent of her juicy quim as my tongue tentatively reached out to introduce itself to the soft warm flesh of her split.
With a slowness bordering on lunacy, I drew the tip of my tongue beginning with the lowest point of her pussy that I could find. I allowed myself the luxury of sliding it upwards, ever so slowly, locating, tasting, and memorizing each sweet tasty morsel of pussy-flesh that I could find. By the time the tip of my tongue reached the apex of her furrow, I stabbed out knowingly and assaulted her clitoris with a brief, but frenzied series of quick fleeting licks that caused Jackie to suck in her breath, unable to exhale until I had once again begun the slow, maddening decent back down the liquefied groove of her cunt.
I don't know how many times I repeated this process, at least a dozen though, and as the intensity grew, so did the scratch marks in my back become deeper and more cleanly etched as it became obvious that I was turning Jackie's pussy inside out with my tongue.
"Fuck me Jake...please, fuck me...now!" She said finally.
"You're sure?" I asked once again. "I'm more than happy to keep doing this until you cum."
"No...I want you inside me. I want to feel you, I want to give YOU, my virginity!"
I moved up against her, but realized as I did that I had once again softened considerably. Excited yes, but in concentrating purely on her pleasure, my own excitement level had diminished slightly.
"Nothing, you're just gonna have to give me a second here. I'm not quite hard enough," I said.
"You don't want to do this do you?" She asked worriedly.
"It's nothing like that," I assured her. "I do...I just need to get harder again is all." Even then I placed my hand around my cock and pressed the knob of my head against her opening and gave it a slight push in the hopes that the head at least would sort of slip into her. That didn't happen. Of course it didn't help when she moaned painfully so either.
"I'm sorry Jake, that hurt a little. Go slowly ok?"
I had been trying to of course, but maybe I had pressed against her a little too forcefully. "OK," I told her, reaching down once again until I was reasonably sure I was where I was supposed to be, I pushed against her as softly, yet as firmly as I could. This time I heard as well as felt the harsh intake of breath as she grimaced in obvious discomfort.
"Fuck! I'm sorry sis, I'm trying to go slowly, I am...really."
Brilliance suddenly came to me.
"Jackie, maybe if you hold me, and sort of guide me into you, maybe that will work."
I felt her hand wrap around me a second later, and I pushed up so that I could rest more on my knees and give her freer access to my cock. I would also have a better view of what we were doing, or doing wrong, and hopefully adjust however she directed me to do.
Once again I pushed...slowly, but knowing I had to apply a little pressure in order to finally break through her stubborn hymen.
"Ouch!" She almost screamed. And I backed off immediately, frustrated and more than a little bewildered why this was proving to be so damn difficult. And then...I heard Jackie crying.
"Maybe we need to take a little breather," I suggested.
"Maybe this isn't going to work after all," Jackie said almost too quietly to hear.
"Maybe," I answered back beginning to feel both frustrated as well as considerably inadequate at my obvious inexperience.
We lay in the dark side by side, holding hands, but not saying a word for a considerable amount of time. Finally I couldn't stand the silence any longer. "Maybe I should try loosening you up with my fingers for a while," I suggested. "Maybe you need just a little more lubrication or something."
"Fuck Jake, I'm already wetter than I ever remember being. But you're right...maybe with your fingers."
For a while, I caressed her clit, tickled it and twirled it between my fingers trying to imitate the way I had gently sucked her with my lips. She was wet...and perhaps even more so by the time I tried to insert my finger inside her. "Shit she's tight!" I thought to myself, and then tried pressing it inside her until once again she moaned, not in pleasure, but in obvious pain. And once again, Jackie started crying, and this time, I really was worried that someone would hear her.
When I heard the door to my bedroom open, the first thing that came to mind was "Fuck...I really do need to remember to lock the fucking door!" And then my next thought, spoken aloud was..."Becky? Dawn?"
I didn't know WHICH one of them was standing there, but obviously someone was. I'm not even sure that Jackie was aware of anyone else being in the room with us yet, but in a way I was glad they were. With her crying, and me not sure what the hell I could do about it, I was more than happy for whatever advise that either Becky or Dawn could give us.
"Maybe I can help," Mom said.
"Mother?" Jackie said.
"Shhhhh baby, mommy's here to help you."
Sometimes you ask the stupidest questions during the most unusual times, and this was one of those. Maybe it was my way of trying to get a feel for my mother's true feelings about what we were trying to do here or something, who knows...but I whatever the reason, I looked up at her as she reached the bed and sat down.
"Where's Becky and Dawn?"
"They're asleep," she said. "Too much wine I think. I figured that SOMETHING was up when it was obvious the two of them were trying to pour wine down my throat. And then, the way you and Jackie were acting around one another, just like the two of you used to do when you were kids. I knew you'd been up to something, and like then, I knew that you were up to something now. When I came out of the bedroom and saw Dawn and Becky asleep in the living room, I knew they were there standing guard. It didn't take two and two to figure out the two of you were in here together, and then I heard Jackie crying, and figured out exactly what the problem was."
"She's a virgin," I said stupidly.
"I know, she told me a while back she still was."
Jackie had quit crying by this time, but it was evident she was nervous about mom's being there.
"It was you who walked in on us last night, wasn't it Jackie?" She asked.
"Yes," Jackie replied softly.
"I thought it might have been. Had it been Becky, she might just have been bold enough to want to join us. Dawn would have said something first, and then either left the room, or stood there until she was invited too. So I figured, it had to be you."
"You're not mad at me?" Jackie asked.
"How can I be mad at you for something I've done myself, and for something I still want to do again?" Mom said. "But we can talk about that tomorrow. Right now, I think I can help you...if you're willing to let me."
She really didn't wait for either one of us to give her an answer; she just sort of took over and began telling us what to do.
"In the first place, the missionary position really isn't the best way for first time sexual intercourse. It can be accomplished that way of course, like most every position. But, it can be a lot more difficult, and far less pleasurable the first time around. Now, if you're willing to trust me. Jackie, get on your hands and knees, and move closer to the end of the bed. Jake? I want you to come around here, and stand behind her, but don't even try and do anything until I say so."
We both did as we were told of course, and once in position, mother moved me closer to my sister and had reached down holding my cock, softly stroking it and making sure that it was as nice and hard as it could be. At the same time, she stroked my sister's cunt-lips with it, teasing her and ensuring that she was becoming aroused too. She also petted my sister's pussy with her other hand, gently stroking and rubbing her clitoris, and telling her how good it felt, and how her own pussy felt when she had a cock up inside her. Listening to my mother talking in such terms was incredibly erotic for me anyway, and I hoped, it if was getting to me like that, that maybe it was for Jackie too.
I felt mom position my prick at the entrance of my sister's pussy, and then felt her hand as she more or less explored the two of us until she was satisfied that everything was exactly where it should be.
"Jackie? I'm not going to lie to you. This is going to hurt a little bit; you have a particularly strong hymen, and it plain and simply isn't going to be painless. But...if you listen to me, it will be quick and over with before you know it. But you're going to have to trust me here," she told her.
"Jake? When I put my hand on the back of your ass, I want you to thrust yourself into your sister with all your might. Don't stop for any reason, even if she cries out. But DON'T do it until I touch you...understood?"
"Jackie? You'll feel a lot of pressure at first, and probably a little pain, but the moment Jake breaks through your hymen, the pain will go away. When you do Jake, keep going, but don't pull back out, just lay there inside your sister. She'll know when it's ok for you to move again."
I could feel the subtle movements of mother's hand on my sister's pussy as she slowly and purposely pleasured her. Though I couldn't see it of course, I could tell by Jackie's breathing that whatever mother was doing to her, that it was starting to make her feel good.
"I want you to cum for me honey," Mom told her. "Concentrate on your clit, think about how good I'm making it feel, and let yourself enjoy it."
Jackie did. Whatever mom was doing, Jackie was really getting into it, and before long her breathing was becoming considerably more raspy and breathless as her orgasm neared. I heard the catch in Jackie's throat then as she did, and simultaneously the touch of my mother's hand on my ass. I shoved into my sisters cunt with every ounce of strength that I had, felt the tightness of her pussy trying to bar my way, felt her stretch, and then suddenly felt myself slide into her.
"Don't stop Jake!" Mom yelled...push...push!"
But I was already inside my sister, to the hilt, and felt her cunt surround me suddenly, almost disbelievingly so.
I had heard her cry out in pleasure as her orgasm began, and I am pretty sure that even when I tore through her hymen, that the sound of her pleasure didn't turn to pure agony, or even close to anything like that.
"How's it feel now honey?" Mom said, once again stroking her back, and caressing the side of her face.
"A lot better. Shit mom, he IS fucking big isn't he?"
Mother laughed. "Yes, yes he is. Almost hurt me when I fucked him too, it had been so damn long. But I'll tell you honey, once you get used to it..."
Once again...I was in the same room, but they were talking like I was a thousand miles away.
"Now, wiggle back against him, slowly...let your pussy get used to the feel of that nice hard dick!" Mom told my sister.
I felt Jackie move against me as though testing that out.
"Hmmm yes, I think I am starting to," she said.
"Does it hurt any more?" Mom asked her.
Jackie moved back against me, and I in turn pulled out just a little, and then moved to meet her backwards thrust.
"Oh...no, that...oh my, that feels good!" She said, now pulling away from me to the point that my cock almost, but not quite slipped out of her. "Oh Jake...now, slide back into me...slowly...slowly, yes...that's it. Just like that!"
I fucked into my sister's cunt, loving the sensation of her pussy as it began to respond, and yet very much aware that my mother was sitting there next to us watching.
"Well, I think the two of you can figure the rest of it out for yourselves." She said finally. I felt her stand up and walk towards the door. My eyes felt like they were glued shut, but I somehow managed to open them and look up towards her just as she reached the door, opened it and turned around one last time to face us.
"I love you both," she said, and then disappeared through the door, closing, and locking it behind her.
Jackie and I made love for a long time after that. We both knew that there would be much to discuss with our mother, as well as with Becky and Dawn in the morning. Neither of us was sure about what the future would bring, or how any of this would eventually affect our lives, or even change them. For now, there was just the sweet, sweet coupling of the two of us, once again joined together, the way we had once begun, but this time, never again to be separated, not ever. End