The First Night She Tried Anal

Introduction:
You let yourself in with the set of keys I gave you a couple months back. You throw them on the table, along with your purse, trying to be quiet. You’re not sure if I’m asleep or not. You leave all your dirty clothes by the washing machine and dart past the bedroom, naked, into the bathroom. You admire yourself in the mirror thinking even covered in the grime from the day, your hair a mess, you feel sexy. Your breasts are perky, with lovely nipples in just the right location that would give a playboy bunny a run for their money.
In the shower you scrub furiously to get the smell of the day off of you, wash out your long hair and step out of the warm water, reluctantly. The twenty second sprint from bathroom to bedroom to get under the covers is always terrible this time of year. Despite your exhaustion you jump onto the bed to kiss me. I’m as naked as you are, you can smell that I had showered; my body wash (your favorite scent in the world) is still fresh on my skin.
“How’d it go today?” You ask as you get comfortable on your stomach, putting a pillow under your hips (the only way you can sleep) and face the door.
“Amazing, I’ll tell you about it in a little bit. I’ve been waiting for you to get home.” You can feel my erection on your skin. Normally you’d be willing to jump my bones, but you had a long day and you’re dead tired.
“I want to, but I’m really tired. It’s so much more exciting when we’re both into it. Remember when we both pulled a muscle trying that one position?”
I kiss the words gently away. I tell you to relax and just lay there; I want to try something new. I stack two more pillows under your hips and get out your favorite peppermint lotion and start to rub your legs and back, my strong hands massaging your aching muscles. You can’t help but sigh and moan from my touch. I kiss my way down your back, targeting each vertebra.
I spread your butt cheeks, and slowly start to lick and kiss my way down to your puckered, virgin anus. You’re wet by now, which is causing me to throb, as I put a finger into your pussy and slowly finger you. I continue to lick you as your groans grow louder and you relax. I’m not going to hurt you, I say. I grab the bottle of lubricant I had on standby and put a small amount on my finger. You feel the cool, slimy lubricant over the sensitive skin of your puckered rosebud, while my other finger rubs against your clit, building up a delicious and taboo anticipation.
I start pressing the finger into your hole, very gently. It slides in easily, about half an inch before meeting some resistance. I know that it was your inner sphincter and I gently whispered to you to just relax. You comment on how it feels so strange, and new, and wonderful. You’re enjoying this anal experiment much more than you thought you would. I continue to rub your clit and you start to loosen up. So many thoughts run through my head, all somehow related to the fact that I can’t believe this is actually happening. When we met you said you would never do something like this, and while I accepted it at the time I always hoped your stance might change. I’m having trouble forming coherent thoughts as all the blood rushes to my cock. Then you really surprise me.
“Reach into the drawer on the bedside table and grab the butt plug in the back.” You tell me with a smile over your shoulder. My mind spins and my thoughts become incoherent. “I’ve remembered how fond you were of this and so I’ve been working up to being comfortable with something in my ass for the past month,” you tell me with a sly, devious look. You little minx! I think to myself. I grab the plug and coat it in lubricant, pushing it in gently, the whole time continuing to stimulate your clit.
It still seemed difficult at first as it met resistance, but that’s to be expected in a situation like this. I can take all the time I want, I think to myself. I stopped pushing and tell you to relax, and you really do feel it relaxing! I push slowly but firmly, and I feel your ass open and take the plug. It was in! But it wasn’t in very far, yet—the thickest part had passed through the barrier of your sphincter, but when it was in only a few inches, I felt some more resistance and you moan and tell me about a mild discomfort. I gave myself a minute and you seem to relax again, so I pushed it in a little further—it was probably about 5″ in when the rest of the dildo slid home up your butt.
I was super excited, but I didn’t want to mess anything up and hurt you just as I was having success, so I let it sit for a moment, enjoying the thought of your tight asshole stretched around the plug packed tight into your rectum. Your pussy twitched and throbbed with pleasure. I would have cum so quickly if I had touched myself, but I wanted… no needed, to have the pleasure of taking you in the ass. I have had vivid dreams about this. The last thing I would ever want to do is hurt you, but I know that if I do this right you will absolutely love it.
You yelp as I remove the plug from your tight rear door and line up my throbbing dick with the crinkled star of your asshole. As I press against its tightness, you remembered fear. My dick is MUCH thicker than the plug that you’d been using, but you trust me, as you feel your asshole stretching wider than it ever had before. A cry falls from your lips as you arch your back, your asshole clamping down tightly on my head. I moan as I feel your muscles rippling over the head of my dick, forcing another inch into your ass as you whimper, trying valiantly to push me out.
“Can we wait just a second, okay, it hurts a little.” You think to yourself that it did hurt, in an odd way that you would never be able to describe… almost cramping, a kind of slick hurt… the feeling that something was being done that SHOULDN’T be done. Your breath catches in your chest as my dick follows your forward movement and another inch was forced into your body.
You moan, leaning your head forward to rest in your hands, panting as you try to adjust to the odd sensation. It felt wrong… dirty… uncomfortable. And erotic for all that, but you are still afraid… afraid that I would slam my dick all the way into you, afraid that something would tear, afraid that this would be more painful than you could bear. So what if you liked sex a little rough, this was an entirely new world to you and you aren’t sure what to make of it.
I squeeze one of your butt-cheeks, holding my desires in check as I look down at my dick splitting your ass open. I could tell that you weren’t completely enjoying this as you fight your own mental battle of pain vs pleasure, and a sick part of me was turned on by that. That part of me really just wanted to slam into your ass, fuck it hard and feel you writhe until you started to enjoy it… but I told you to trust me, and the caring part of me would never hurt you. Maybe as you adjusted I would get rougher…
I grip your hips and push another two inches of my dick into your ass as you moan. If I’m not careful I will cum soon, because this sensation is beyond description. I reach around your body and slide my hands under your chest and squeeze your breasts, feeling your asshole tighten over my dick as I graze your nipples. You bite your lip as pleasure flows from your breasts to your confused groin, your ass tightening uncomfortably making you very aware of where my dick is, but feeling good too. I listen to you and feel you, but don’t start fucking you hard like I wanted to… I just stay completely imbedded in your tightness, feeling your muscles ripple over my dick, as I wait for your body to adjust a little more.
I slide the rest of the way in, and then start to come back out. Feeling me move inside your ass is something that you just aren’t used to. You bite the pillow as your ass ripples, trying to figure out what was going on inside it, your body bucking as I begin to slowly slide back into your body. In and out, very carefully and gently, although by your reaction a viewer might think it was anything but… you shivered and thrash as I opened up your ass, panting as my dick noses deeply into your body, forgetting about how tired you were just half an hour ago.
My hands began running over you, your sides, back, waist, hips, and ass… sliding down the backs of your thighs… and then circling around to begin playing with your pussy. I rub your wet pussy lips with my fingers, gently tickling your clit, as you feel the tingling fire starting, helping to alleviate some of the strange sensation my dick was creating. I can sense a shift in you, as you finally get out of your own head and begin to enjoy the multiple sensations that you are experiencing. The initial pain of insertion is gone, replaced only with the amplifying effect that anal sex has on the rest of your body. Every touch feels more vibrant, every thrust is exploring a new area. You realize that not only does it not feel uncomfortable, it feels good, and you understand why people say it will get better.
Now you begin shivering for a different reason, your ass moving back against me enthusiastically, swallowing my dick and tightening every time I bury it in your ass. Leveraging yourself up onto your forearms, you begin fucking back even harder, enjoying the way my dick stabs into your ass. I groan and take this as my cue to really let loose; my fingers explore deeper into your pussy as I start thrusting hard into your ass, making you cry out with mingled pain and pleasure.
“Damn you have a tight ass…” I whisper to you. You respond by just slammed your ass back against me harder. You are really starting to get into the butt-fucking, wanting to feel more of me in you, wanting to feel yourself stretch to receive me. It felt so deliciously naughty to you, and the pain had worn down to just a slight discomfort that made the pleasure in your pussy seem exponentially stronger.
Your head rests on your hands, although your forearms are still balancing on the bed to keep your ass high in the air. You moan loudly as I pillage your deflowered hole, as you concentrate on the fire that was burning inside of your groin. My fingers twitch and rub, pressing hard against you clit and you move your hips slightly to rub against the pressure, your legs trembling as an orgasm nears. To date you still have yet to orgasm, which is a constant area of self doubt in my mind. I’m not good enough to get you over the edge. Today, however, with this new sensation amplifying everything around it, you wonder if it isn’t possible.
As you start to cum your entire body shakes, your ass tightening over my thrusting dick and rippling with pleasure. Gasping I force my dick in and out of your tightness, increasing your pleasure as I slam deep into your body. Reaching up with one hand to grab your hair, I pull it back, forcing you to arch your back as I pulled you firmly against me. You shriek with pleasure, your hands clawing at the bed as I pulled your hair back, breasts thrust upwards into the air.
With a final plunge, I started to cum, holding your hair firmly as I unload into your ass. You can feel every single pulse of cum forcing its way past your tight entrance and into your body, pushing against the ring of flesh that enclosed the base of my dick. When I finally finish cumming, we both gasp and collapse. You gasp again as my body fells on top of yours, my dick lodged deep in your ass.
You moan, wriggling a little. Now that the pleasure is over you could feel how very sore your poor asshole is, uncomfortable with the dick shrinking inside it. But I hold myself there, enjoying you body even as I shrink. When I finally pulled myself out, your hole is bright pink and starts leaking thick globs of cum. You stayed like that, panting for a moment or two, as I think about what just happened. This was no more than pipe dream just an hour before, and now it was a reality. I wondered if you enjoyed it, if you would do it again.
“So?” I ask as I sit on the bed, stroking your hair. You looked up at me with those pleasure glazed, beautiful eyes, “It hurt,” you say, and then smile, “But it felt awfully good too…”

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