AnnaSophia Goes Anal

It was a nice, normal night out in Long Island -- a nice night to walk down the streets with a friend. A friend who was filming a television show here several months out of the year. A friend who was starring in this TV show -- even if it was on the CW and was a prequel series.

A friend who happened to be AnnaSophia Robb, of several Disney and young adult films, but currently of "The Carrie Diaries." Only about over a million people knew about her and her show, according to the Nielsens. I wouldn't have heard of it if they didn't film in town, and if she didn't come to my coffee shop every day, and if we hadn't become actual friends for the last three months.

But even if regular people didn't know her or her show, a lot of Internet people did. If only because they made gifs starring her most famous body part. Not her big, beautiful blue eyes, blonde hair, gigantic smile or slender legs -- but something big between the smile and legs.

Something that some jackass behind us just got away with pinching.

"Hey!" AnnaSophia squealed, turning to slap the creep who pinched her....rather ample backside. Which was sticking out even more than usual in her blue jeans. Still, it wasn't an open invitation.

The fact she acted faster than me to slap him was kind of troubling. And so was what he actually did, of course. Regardless of....

"Easy, easy, I'm gone," the creep assured, looking far too satisfied already. That satisfaction, my ego, my need to defend a friend -- and some jealousy I did NOT want to think about -- made me spring to action when his back was turned.

If he was going to grab AnnaSophia's ass, I was going to kick his. I mean, literally kick him in the ass with my right foot.

Maybe it wasn't so tough that I took AnnaSophia's wrist and ran away with her before he punched me back. But hell, if he wanted to be a coward, I could be too.

The coward ass grabber cursed and chased us for about a block, but we were too fast for him. Nevertheless, we kept running for another block until we actually reached my apartment building. With the 'danger' gone and the ability to breathe coming back, me and AnnaSophia even managed to start laughing.

We kept laughing off and on until we reached my actual apartment. Yet by the time we settled down for a drink on my couch, AnnaSophia wasn't in a laughing mood.

"That's how it's going to be, isn't it? I'm surprised that was the first time," she commented.

"First time you saw a literal ass kicking?" I tried to guess, though I knew I was probably wrong.

"It's not his ass I was talking about," AnnaSophia stated. "Mine came out of nowhere, you know! It's not going away anytime soon, though. Neither are jackasses like him. They'll just keep pinching and groping and jacking off to it. If I had sex more often, they'd probably wear it out by now! Or they'd want to!"

AnnaSophia got up, her back turned to me -- a most ironic position, considering the topic of conversation. I took one quick look at her hypnotically obscene rear, before she could realize I was part of the problem she talked about. Albeit the nicest example of the problem.

"I just started having sex, you know," she didn't make it any easier at all. "There's a lot to do, but....all anyone's gonna want is my ass, I know it. Most of the time, they probably won't be good at it. It'd be nice if I could....at least get it right off the bat. Maybe that'd set the tone for years of ass play."

I had no answer to that, and few would probably make me look good. Especially with all the images in my head right now. They weren't exactly new images -- or ones that went away for more than a few days around her -- yet I knew how to control myself. At least when she wasn't testing it this much.

"Wait....that's it!" AnnaSophia yelled. "I need a great first time! Even if it doesn't get better from there!"

"I thought you already started having sex," I played dumb, for one reason or another.

"Not that kind of sex!" AnnaSophia still unintentionally played coy. "If guys are gonna just go after my ass....I should find one that'll be good to it first! I can at least lose my anal virginity the right way."

"Jesus...." I groaned in frustration and other emotions. "You do know finding the right guy's a crapshoot? When it comes to any virginity?"

"Yeah. You can't always stumble onto guys who would kick someone's ass for you. Literally," she got right to the point. And that point practically made my throat close.

"You're not serious," I told her before it all spun out of control -- the situation, our friendship and my self-restraint.

"Who better than a friend who respects me? Or at least lusts after me to a respectful point?" she asked, making me wonder how discreet I'd been at certain moments -- and poses -- of our friendship. "You want to stay friends with me, right? Ass or not?"

"Um.....sure, of course," was a weak answer, albeit an accurate one -- and the best I could muster.

"Then you sure wouldn't want to fuck my ass the wrong way. You'd take extra good care of it for it's first time. Even if....not every guy after that doesn't think that way," AnnaSophia figured.

"And you....really don't want to wait for one of the good ones?" I checked again.

"There's probably not much time to waste. Why take the risk?" she answered.

"So I'm not a risk? I'm just the good, safe nice guy good for a b...." I barely kept myself from saying booty call. That stupid joke, and the stupid way I was objecting, wasn't helping me out. Then again, there were some unflattering things I could take from this.

"No one who kicks ass like that is all good. I know I can trust you to be the good kind of bad," AnnaSophia made it sound better. "If you were that creative against that guy, who's a total ass.....I'll bet you could be the right kind of creative for mine."

Yep, it was way too stupid to keep objecting now. The only problem left was her setting the bar too high.

This was AnnaSophia Robb's ass we were talking about. This was an ass that belonged to a friend. I could ravage it then and there, and had frequently thought about it -- but that wasn't all she was asking for. It wasn't all I wanted to do with it either.

But if she riled me up and got me hot like this, I wouldn't think ahead enough to deliver. This was a task one needed to be fully prepared for.

"You know....I'm extra creative after I've had dinner. Too bad it's too late for one now," I reflected. "How about we take care of that early tomorrow night? Then we can take care of the rest." That was good. Less than 24 hours to get ready should be enough -- or be enough to make her come to her senses.

Yet when AnnaSophia thought about it, gave me her brightest smile and agreed, I was stuck with this calculated risk.

Somehow, I let her head back home after a few more minutes, and after choosing a place to meet up for dinner tomorrow. Somehow, I got myself to sleep before 1 a.m. afterwards. Somehow, I kept my hand off my cock for more than a few minutes before getting out of bed that morning.

By the time work ended and it was almost dinner time, I let myself have a....practice run. If AnnaSophia hadn't changed her mind and would be.....coming back here after dinner, I wasn't going to let this be....a quick dessert. I had to know I could.....stand tall as long as possible, in spite of the mighty task ahead.

It wasn't like this was the first time I jacked off to her ass. It wasn't as if I didn't cum earlier than I wanted to in those times. But the thought of actually being hours away from seeing it, touching it, fucking it, devouring it....

It all made me break my record time by about a full minute. Which wasn't exactly encouraging.

As such, when I got to the restaurant we agreed to, part of me almost wished she wouldn't show up. It would spare me the embarrassment, and probably mean she was okay and thinking straight too.

But I sure wasn't when she actually came in. Not when she was wearing that pink dress that looked....pretty easy to lift up. If she saw me checking to make sure, she didn't comment, as she just pecked my cheek and went to check on our table.

When we were seated, I finally saw her looking uneasy too. Maybe now that she was carrying this crazy plan out, she was seeing how crazy it was. I should have offered her an out, but her entrance made it nearly impossible now. Instead, I tried to keep it light.

"Should we go over ground rules while we wait?" I attempted to poke fun.

"Oh. Um....you know I don't want it that rough. Everything else should be fine," AnnaSophia assured me. After a pause, she asked, "How about you? What do you want?"

"Uh....you're being generous enough, I think," I conveyed.

"Am I? I did steamroll you into this. I know you could have said no, but....I know no one in your position would," AnnaSophia admitted. "But what do you want after that? Do you want it more than once? Do you want to stay friends, or is it gonna be impossible? For one reason or another?"

"Hadn't really thought that far," I admitted.

"Me either. I just thought about this being a good....first time. But we could still taint it later. For any number of reasons," AnnaSophia proposed. "If you really don't want to risk that, it won't make you less of a man. I should have let you know that before I forced you into this."

"Funny choice of words," I blurted out, though maybe this wasn't the time to be light anymore. Nevertheless, AnnaSophia chuckled anyway, which gave me a bit more courage for the serious stuff.

"You're right. No one in my position, so to speak, would turn this down. Few of them would think of the consequences, though. I wish I didn't have to," I confessed. "But hell....you wanted this to be with someone who wasn't an asshole. The fact I care about that other stuff should prove you made the right choice. And that....we can figure it out and stay good afterwards. No matter what we figure out."

"I guess that takes a few loads off," AnnaSophia said, making us both groan. In a comedic way, not the other way -- it still helped, though. "I just didn't want us to feel too weird first. Or obligated."

"You're about 24 hours too late on the first part," I pointed out. "The second one....it's really more of a favor than an obligation. One I'm not gonna take lightly."

"Don't make me take it too lightly either," AnnaSophia couldn't resist saying. "Sorry, sorry....at least we're getting that out of the way now too."

"In a restaurant where anyone could hear us talking about anal sex. Good we got that covered," I couldn't help but joke too. Really, what else could we do? Better we had reason to laugh now than later anyway.

The laughter faded a bit by the time we finished dinner. There was only one other stop for the evening now. As such, neither of us could help but feel awkward and hesitant again as we headed to my place.

We didn't say a word once we got to my door. I opened it up and gestured for AnnaSophia to lead us in, since this was her idea. As she moved in, my hand unconsciously went onto her lower back to move her along -- about two inches above her ass.

It was the first time I touched her so close to....that area. The first of many tonight, if I didn't screw up. Although I hadn't actually touched it, touching her like that at all made it really hit home.

And made it feel like it wasn't enough.

I closed the door behind us, with AnnaSophia standing in front of me. She looked as on edge as I felt, just from that brief touch with the promise of more. Then again, it was up to me to actually get more.

My right hand went over to her lower back, touching her right above her ass again. At that point, there was really nothing else to say but, "Fuck it."

I briefly heard AnnaSophia hum her agreement, before our lips came together.

I kept my head and lips still, adjusting to the sensations of kissing her. Right before I broke off to catch my breath, she pushed her lips harder against mine. Her right hand went to the back of my neck before our lips finally broke, but we put them back together and opened our mouths right then.

Mine opened even wider, for different reasons, once my hand went two inches lower.

"Holy fuck...." I breathed out, as I got my first good feel of AnnaSophia Robb's unreal backside.

It felt like I was barely holding half of her cheek. As much as she was packing into her ass, it felt so firm and soft instead of hard. And she still had a dress over it....imagine what the bare skin felt like.

I knew I was done imagining. To show her, my hands started pulling up her dress and bunching the bottom of it together. AnnaSophia went back to kissing me, so I assumed she approved.

I certainly approved of getting her dress up enough to expose her ass. That was still nothing compared to feeling it -- and nothing else at all.

"You don't have any...." I broke off to mutter, though I couldn't finish the sentence with "panties." Of which she had none on -- and probably didn't even at dinner.

"Seemed really, really pointless, don't you think?" AnnaSophia asked. I really couldn't argue with that -- and I had better things to do.

Like putting AnnaSophia against the wall, so she could lean back while I kissed her. And while both my hands were under her dress and on her ample ass. Since there was so much down there, it took me a while to feel all of it, which helped me take my time.

Our mouths were actually moving faster than my hands, in truth. Eventually, we gave it a rest and broke off, though AnnaSophia went back to nibble and suckle on my upper lip. She just smiled a smile that might look adorable in most cases -- but it didn't just look adorable here.

I would have gladly done nothing but fondle her ass, while watching her big bright eyes darken and her sweet smile turn even sexier. However, I wanted to give her a little more effort. Therefore, I reluctantly broke away from her eyes and kissed down to her neck, as the front of my groin started rubbing against hers.

Now that she had an idea of what I had, she started to push against me as well. To help her along, I grabbed as much of her booty as possible and pushed it forward, full on grinding my trapped erection against her while suckling her neck.

"Fuck me, fuck me...." AnnaSophia groaned, or possibly commanded. "I need to lie down...."

It took everything I had, as well as one more squeeze, to obey her orders and back away. AnnaSophia caught her breath and straightened her dress out, then stepped out of her high heels. But if she wasn't going to lie down like she said, then I didn't want to stand back much longer.

It helped -- sort of -- when she lowered the straps from her dress, though.

Once she pulled the front of her dress down to show her bare, round B-cups, she arched them up while trying to reach the back of her dress. "You mind?" AnnaSophia asked, breaking my concentration from her chest.

She turned around, letting me see the zipper on her dress -- and giving me silent permission to lower it. I got halfway down before she said, "Thanks, I got it," and shooed me away to do the rest.

The rest included wiggling as she slid her dress down, bending down as she put it on the floor, and then stepping out completely nude. Stepping out with her back turned to me.

And there it was. This generation's answer to Jennifer Lopez and Kim Kardashian -- bare, impossibly heart shaped, thick, curvy, mouthwatering, and all mine for the next....well, hopefully I'd last more than a minute.

I was less confident when AnnaSophia walked towards my bedroom door, her ass swaying and swinging like she was trying to give me a heart attack. It'd be a good way to get out of it, really.

"Wait!" I made her stop, if only so I could breathe again and give her something to drool over. There's no way it would make us even -- my ego and other things weren't big enough for me to believe that. But I had to give her something.

In a flash, I unzipped and unbuckled my pants, finally letting my cock get some air. After getting my pants down and kicking them away, AnnaSophia finally saw what she would be fitting in. If she still approved, of course.

She got it as hard and as throbbing as it could get, so I had nothing else to impress her. Still, she didn't look like she hated it. Either way, she then made her way into my bedroom, so I took that as a win.

I ran in just in time to see AnnaSophia getting onto my bed, lying on her stomach. I almost grabbed myself right then and there, until she rolled onto her side. By then, there seemed to be no reason to keep her waiting.

Although my suit was still on, I laid right down next to the naked AnnaSophia, who promptly rolled me onto my back. Her next prompt action was to sit up and straddle me, giving her room to unbutton my suit and pull it open herself.

I ultimately sat up and helped finish the job, then laid back down once I was totally naked. "So do I just....go for it?" I left it up to AnnaSophia.

"You can ease me in first," she answered as she laid herself down on me. I figured I could let my hands squeeze her again for starters.

"Like that?" I asked as I kneaded her peachy rear -- then dared to brush a finger between her cheeks.

"Something like that," AnnaSophia approved, pushing her hips down against my groin.

"Is this closer?" I asked before dipping my left finger down into her pussy.

"A little colder....but not bad," she admitted as I fingered her. Of course, as soon as she got wet enough, I intended to get warmer. In the meantime, she relaxed against me while I watched myself finger her and jiggle her apple-shaped behind.

That would have been enough for me, if I didn't have even bigger plans. Starting with taking my wet left finger and moving it up to her other hole. It probed her rear and teased it's entrance/exit, causing AnnaSophia to moan and grind herself harder on me.

"Wait, wait, wait," she made me stop, sitting herself up again. I kept my finger against her asshole as she lifted her hips up, putting her pussy right onto my cock head. Soon, she slowly lowered herself down and took me in -- so I took the hint and started filling her in the back too.

AnnaSophia clenched around my finger and cock, letting me savor both tight, hot spaces. Before long, she started to outright ride my cock as my finger settled into her ass. Instead of pushing that in further, I wiggled the tip around, which got her to moan louder and take the rest of my cock in.

Now that she was sitting right on me and being filled in both holes, I put my right hand to work and started rubbing the front one. My hips also began pumping her while my finger went to work thrusting as well. Within moments, AnnaSophia was riding me and thrusting her hips back and forth, taking in more of me all around.

There was still one more way I could work her over, however. To do that, I took my right hand off her pussy and used it to help me sit up. Anna Sophia rolled with me and wrapped her legs around me, right as I put my mouth on her chest and my hand back on her pussy.

As my lips and tongue wrapped around her left nipple, I felt her wrap her arms around my head. In return, my right fingers rubbed and teased her pussy, all as my left finger rubbed and teased the inside of her ass. Attacking her in four ways really made AnnaSophia moan and bounce on me.

"Yeah, so fucking good....fuck me twice as hard...." AnnaSophia ordered, and I tried to obey. Biting down on her nipple, I tongued it mercilessly until AnnaSophia pushed my head backwards. "Fuck me in all my holes," she briefly confused me.

She gave me a better clue by kissing me -- more by thrusting her tongue in and out of my mouth, really. Getting the idea, I started fucking her mouth with my tongue, right as I went faster in her asshole and pussy. When I pulled my tongue back, AnnaSophia groaned long and loud, her face and eyes now burning with desire.