The Two Cherries

Author's Note: This is my first actual submission of any real kind. I write quite a bit, but it's usually done just to keep my thoughts from becoming a jumbled mess. This story was actually inspired by a conversation I had with my girlfriend. It was written for her, with her in mind, but it's the first story I've ever attempted. Although I've read many better written stories from this site and since I rather liked writing this, I wanted to share.

If you like it, let me know. If you don't, well... let me know that, too.

Thanks, and enjoy!

re808

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I'm not sure what night it was. Friday. Saturday. It really doesn't matter. She came over to my house like any other weekend night when she wants to get away from that feeling of someone looking over her shoulder. Her roommate Like she has her very own 'over-watch'. It started as a fairly normal evening for us... she has her shots of vodka, I with my White Russians. We talk. Sometimes it's pretty deep, other times it's just about whatever inane topic that comes to mind. But tonight, I decided it best that I stayed a little more sober than usual. And for what I had planned, the last thing I needed was a case of the 'whiskey-dick'. I wanted 'round two' finished in a place that was new to her. So, it was with that third drink that I decided it time to slow down and not cross over from buzzed to drunk.

We decided to move things inside while the shots kept flowing along with the conversation. And that's when I see it. That first clue that lets me know when conversation needs to stop and 'other' things need to happen. That look of total relaxation and inhibition.

I love dancing with her, so I reach for her hand to pull her to me. We both naturally go to that dancing position we learned in our ballroom dance lessons and just start swaying to the music. As I let go of her hand to cup the side of her face, I lean in to whisper something in her ear that only she will ever hear from my lips. I kiss her cheek, then her neck, and then as I look into her eyes, I kiss her lips softly until she opens them for something much more passionate.

Our incessant and oh so wet kissing turns into a full-blown make out session, reminiscent of two teenagers afraid to take that next step and continue past 'first base'. HOWEVER, our teenage years are behind us and I am far from afraid to advance past 'first base' at a full gallop. I break off our kiss long enough to ask her to unbuckle my pants. She then removes her own as I kick mine aside along with my shirt. Realizing that I can't leave a job undone, I unbutton her shirt and kiss her again as I slide it over her shoulders with her bra following shortly.

As much as I love to kiss this woman, I find myself unable to resist ravishing her body. While still kissing her, as if 30 minutes isn't enough, I gently nudge her onto her stomach on my bed where I continue to kiss her, moving to the back of her neck, then further down her back to one of the loveliest of asses I've ever seen. And from the very first time I'd taken her from behind and seen her beautifully puckered hole, my tongue has been drawn to it. That is one of the 'cherries' I plan to take right now... me having never tongued someone's ass. She knows what I want and she's decided to let me have it.

I spread her ass so I have full access. Gently, I use my tongue to lick around the edges. I tease her with it almost to the point of misery until even I can take no more. Using the point of my tongue, I use more pressure and start licking the very center and then I go back to circling the edges. I then use the flat of my tongue to lick just below her hole and then stopping to lick at the center once again.

Although I am nowhere near done pleasuring my love's ass, I get the feeling that her pussy is feeling left out of the fun. I reach for our new glass toy that just seems to know the right spot to hit. Finding that it needs no lubrication other than her own, I slid it in until I know it's hitting just right.

Acting on its own, my tongue can't help but find its way back to her uncharted territory. Licking it with increased fervor while the glass rod is sliding in and out. And then, as if reading my mind, wondering if she REALLY likes what I'm doing, I hear her say, 'Don't stop, baby!' Unable to ignore such a request, I continue. But, only for another minute or two, for I have other plans.

Hearing a slight whimper from her when I do stop almost makes me resume my fun... well, 'our' fun. But, just almost. It's then that I reach for the smallest of my three plugs and the lube. Having applied a very large amount of the slippery stuff on both the plug and her hole, I gently ease in just the tip. I wait a moment and ease a bit more in so she can get used to something going in the opposite direction. All the while not forgetting the glass toy still lodged inside her pussy, I slide it in and out in time with the long, slender plug... eventually sliding it all the way home.

I find myself kissing my way back up towards her neck and kiss her amazing lips. I want to make sure she's doing ok. With a nod that she is, I reach for the plug and gently ease it out... but, not all the way just yet. Teasingly, I thrust it in and out for another minute or two before removing it.

It's then that I decide it's time for the plug that's one size up. After once again applying a generous helping of lube, I ease just the tip of the larger plug into her slowly loosening hole. She understands that if it gets gets too much to bare, that it's ok to stop. But, she's doing good. I continue to ease in the rest of the larger plug. Again, slowly and with a gentle in and out until I have it in all the way.

After having filled one hole with the plug and the other with a toy, I feel an extreme urge to fill another that has only had my tongue as of yet. With the plug still inside her, and having handed the toy over to her capable hands, I nudge her onto her back where our mouths meet to make love with our tongues like only lovers do.

Now, I am a Cancer. Which means that, more often than not, I'd rather make love than fuck. But, not now. At this moment, what I want is to fuck the one hole that has yet to be occupied. And right now, my Scorpio girlfriend is of the same mind.

With barely a nudge, she knows exactly what I want and moves across the bed so that her head is hanging off the edge. On instinct, she moves the glass toy into her pussy which slides in easily. Now that two of her holes are filled, I grab both sides of her head so I can fill yet another. Her lips part knowingly, allowing my cock to enter her mouth. I slide in and out slowly at first, but soon I get caught up with how good her tongue feels and start fucking her face with abandon... gagging her at times and only pulling out to make sure she is getting air.

As I continue to skull-fuck her, I see the sway of her tits and the motion of her hand fucking her own pussy. I need to slow down, because knowing that she also has a plug in her ass, preparing it for the cock that is now in her mouth, is proving to be too much. I pull my cock out of her mouth to tease her by rubbing it around her lips before putting it back in just past the tip. I ask her to massage it with her tongue while sucking on it with enough pressure to make Hoover jealous. This eventually does become too much as I can't help but shoot a massive load into her waiting mouth.

Tasting my cum, the plug in her ass, and the toy fucking her pussy has also sent her over the edge, causing her to cum with spasms that seem to go on for over a full minute. And seeing her cum as hard as she did, has only made me ready to replace the plug in her ass with something much better. I busted one cherry when she let me lick her ass. It was time to bust another by fucking her ass with my cock.

I roll her back onto her stomach and begin to pull the plug out a little at a time. For a moment, I begin to fuck her ass with the plug eventually leaving it in at its widest point, allowing her hole to relax again to prepare for something bigger.

Removing the plug altogether, I reach for only the lube this time. Remembering to apply a large amount to my cock, I apply even more to her ass, using my finger to push some inside. Even adding a second finger to give it one final stretch. I take a deep breath as I ask if she's ready. With a breathy 'Uh huh', I remove my fingers and place my cock at her opening. Reminding her to relax, I push through and stop. Waiting for her to adjust to something larger than what was just there. Having been given the ok, I press forward just a little more and wait. I can feel her pulsing around me... tightening and then relaxing. Again and again. With a final ok, I push forward until her ass has completely engulfed my cock.

I understand that popping an anal cherry requires extreme patience if there's to be any sort of pleasure. So again, I wait for another ok before I start moving. She gives it, and I begin to stroke my cock back and forth, using her anus to milk even more cum from me.

Although I've picked up the tempo at her urging, I've found that moving in and out slowly can give just as much pleasure as a hard fucking. This is no exception as I realize that I'm about to cum for that rare second time. I take one final plunge as I push my cock in to the hilt, filling her ass and giving her something she's never had... an anal creampie. And as I'm completely overwhelmed by the amazing gift my girlfriend has given me, I can't help pull out and replace my cock with my mouth. Sucking out what cum I could and licking her hole as it constricts back to its original tightness.

As I collapse by her side holding her to me, my thoughts turn to something else as I drift off to a sweet oblivion... will she reach for the toy I bought for her that she likes to call 'Eve', short for 'Evil'? From the very first time that I got to 'know' her, she must always have one last orgasm before sleep, regardless of how many she's has with me. Because this woman is insatiable! And I love her for it!!!