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Anal With Anna

Updated: Sep 21, 2023


     College wasn’t as scary as I’d originally thought it would be, I mean who doesn’t enjoy hot assed chick’s all day long? The best part was Anna. Her and I literally had every class together, of course we sit by one another as much as we can. We have always gotten along and never had a need to argue or fight. Shes got the hottest ass I’ve ever seen. Well, besides her sister, Cali. I'm definitely sexually attracted to Cali, but Anna is my dream chick. Gorgeous and sexy body, perfect little ass cheeks, I wouldn’t think twice about eating it, for sure. Last year at a party, a group of girls drunk off some whiskey invited me into the shower with them. Me being a bit high and a little drunk myself, took that offer without any hesitation. If only that sort of opportunity came around more often, it sucks being an introvert. Being the more outgoing one, Cali usually finds ways to make things less intense by being sort of a middle-man for various situations such as when Anna accidently lets a fart go and is too embarrassed to and awkward times.


One fine day.

    Struggling to get out of bed and take a shower, I wasn’t quite prepared to start the day. I mean it was the end of the week after all, why couldn’t class start later? College is a different place.        I could hear my step-sister in her bathroom, singing her favorite song of the week, just as shes done every morning before school, even throughout high school. I can’t say it hasn’t interested me a bit to know what exactly she could be doing in the shower for the whole twenty minutes. There’s only a couple of possibilities, but I’ve always sort of just forced myself to stop thinking about it because she was sister, regardless of her only being my step-sister, I’ve just always felt that I shouldn’t have dirty thoughts about her showering. But as of late, I’ve been somewhat fascinated by the idea of finding out what shes up to in there. Its hard to ignore these things when you realize you’ve lived together for so many years now, yet for that twenty minutes each day, it was a complete mystery where my sister would go. Finding myself obsessing over the different ways id go about unveiling the mysterious missing bathroom time, I was more so just needing an answer to my question, what was she really doing in there?


      Maybe I’d find some time during lunch to sort out a plan of action, of course I felt guilty even considering something like this, perhaps I won’t even bother. Drifting back into sleep, I fell into a pretty intricate dream state. Strangely, Anna was over at my place, swimming in the large extravagant backyard pool our parents had built for my sister and I. Anna had on a pink bathing suite, seemed quite flimsy, but I wasn’t opposed to it, she climbed up onto the upper waterfall rock formation and jumped off into the pool below. When she emerged, Anna’s bathing suite has disappeared, leaving her extremely embarrassed and confused. Cali began to laugh at Anna for losing her bathing suit, shouting with laughter , “Everyone look at Anna’s ass!”. Of course my eyes immediately sprung back to Anna, watching as she made her way to the steps of the shallow end of the pool. I didn’t find it funny, in fact I felt bad for the poor girl, and ran inside to grab her a towel so she could cover herself up. Grabbing the towel from our bathroom, I quickly bolted into the hallway headed outside to offer her the towel, though was startled as I collided with her naked self, both of us falling to the ground fairly hard. “OH my God!” we said it at the same time as we fell, her on her back and me face down in her crotch. It took a moment for me to fully grasp what just happened, an even longer moment for me to take in the magnificence of what I was looking at. Anna’s vagina was challenging me to a staring contest, one I’d hoped was never going to end. I could tell by her lackluster response and delay in getting up that perhaps she was more than willing to let me indulge my senses in the beauty that comprised her genitals. Being the genuine and respectable young man I am, I decided to withhold my desires and get back up so I could help her up and offer the towel to her. Before I could get very far, she grabbed a handful of my hair and held my head right down where I truly wanted it to be. “You gonna pass me up?” She said, with an obvious sexual inclination. I knew it wouldn’t be long before my sister came barging inside to find out where we were at, so without wasting another second I grabbed either side of Anna’s waist and pulled her toward my waiting mouth. I began making circular motions right around her hardened clit, running my tongue down the center divide every few rounds, and back up again. Grinding her waist against my face, guiding her red throbbing pussy exactly where it needed to go.


Looking up every once in a while to make sure my sister hadn’t yet come inside, and once the coast was clear my eyes returned to Anna’s hands as she squeezes her budding breaststroke in pleasure. Practically drooling cum, it didn’t take a rocket scientist to know she was about to climax, and by the gentle pulsing of her vaginal muscles it surely was going to be an amazing sight to see. Eagerly waiting for her to squirt her hot fluids all over my face and inside my mouth, my tongue dancing around her clit like a pinball in a pinball machine, she was making my cock extremely hard by her build up to orgasm. I began to finger fuck her now soaking wet pussy while sucking her desperate clit with everything I’ve got, every once in a while I’d glance down to catch a glimpse of her extremely tight puckered pink asshole desperate to watch it pulse in and out while it squeezes into a tight pucker the moment she begins to peak in climax. The more I examined her asshole, the more I desired it. Continuing to thrust my now two fingers between her puffy lips,  I decided to clean up some of her mess that leaked down her crack, her light moaning become deep heavy breaths the closer my tongue would get to her virgin asshole. Anna was going to cum any second now, and I wanted her to remember this one as her best. I started sucking on her clit again, shoving my fingers as deep and hard as I could, positioning my index and middle fingers in an upward claw-like motion. This sent her pussy into a fucking frenzy, forcing her to squirt small streams of hot cum right inside my mouth. I surely wasn’t going to waste a single drop, swallowing as much as I could physically take. Deep in a state of extreme euphoric climax, I quickly pulled my fingers from her throbbing pussy and shoved them both in her tight horny little asshole where I continued the same upward claw-like motions deep inside her bowls. This sent her into a climatic coma of sorts, so intense that she stopped breathing altogether as she squeezed her hard horny nipples as hard as she could to maximize her peaking orgasm. Arching her back and directing her bottom directly down onto my two fingers, Anna started to ride my fingers with an aggressive desperation to fulfill a deeply longed for anal need. As she rode my fingers with her asshole, I positioned my tongue ffirmly outward in the direct path of her clit as she lifted up and slammed back down. I don’t think she even knows how to handle this orgasm, considering she’s Cumming from both of her holes simultaneously. Suddenly she lifts up off my fingers and frantically begins unbuckling my belt and unzipping my pants, revealing my extremely hard cock as it springs out from my boxers. I’d never seen my dick so big and throbbing before. The second my cock came out, Anna turned herself around on her hands and knees, shoving her desperate asshole and pussy up in the air. I wanted to badly to establish her asshole, but I knew what she wanted, and she knew what she needed. I’m not going to lie, I wasn’t sure that it was a good idea to try and shove this huge cock inside such a tiny cute hole, but this wasn’t the time for questioning. She wanted it, but before I go an give her asshole the attention it craved, I shoved my fingers back inside it and pushed my cock inside her waiting pussy. Immediately she started to cum, and I mean hard, I could tell by the way she began to suck my cock inside of her, she wanted my cum so badly. Slamming my dick inside of her with an intense desire to fill her up, I wasn’t going to just abandon that sweet little asshole after all the hard work it put in to please my fingers. Hoping she could it in full, I pulled my cock out and pressed my head up against her needy butthole, plenty lubed enough for anything she wanted to shove in there. Before I could even begin to work myself inside, Anna forced her bottom around my cock with a swift backward thrust, her asshole how clasped around my entire shaft. She let out a deep groan and started to rock back and forth, working up to a fast and hard ramming. My halls slapping against against her soaking wet pussy, it didn’t take long for me to feel her anal muscles contracting as she started to anally climax wrapped around my thick throbbing dick. This one was different, I could tell she was being satisfied in a much deeper way as her breathing turning into short bursts of panting. Harder and harder she slammed her ass onto me, this was what she wanted, this was what she very much needed from me. I felt my cock begin to mushroom as her bowls tightend and tensed in preparation for her ultimate climax. All I could do was stare down at Anna’s back as she rode me to orgasm, her face down on the carpet with her arms extended in front her to hold her position. Her breaths fell silent and her face turned blood red as she entered into organic bliss, my cock slamming her asshole as hard and fast as humanly possible, stretched around my big thick cock tighter than I thought possible. I couldn’t hold back anymore, with everything I had in me I began to fill her bowls with hot milky fluid continuing to fuck her with deep passionate thrusting. I felt every muscle in her body gripping onto my cock, milking my balls for every drop I had.


For what seemed like several minutes, we fulfilled each other’s desperation in euphoric synchronicity. On our knees in the hallway of my house, the both of us in a state of post orgasmic bliss, neither of us wanted it to end, surely the best either of us ever had. I began to wonder why it was that my sister hadn’t yet come inside, especially considering the uncontrollable groans Anna had been making. Surely Cali would have heard us and at least come inside to laugh and point out our obvious sexual activities. Pulling my still throbbing cock out slowly from the intense grip of Anna’s ass, a string of thick cum was still very much so connecting us. She let out a final pleasurable moan as my mushroomed tip was pulled from her, but before I could get very far Anna wanted to clean me up a bit. She began to suck the rest of my cum from me, gripping freshly emptied ball-sack as she went up and down my shaft. I knew I wasn’t going to be able to cum again, at least not right now, but I let her suck it to her mouths desire. As Anna gave my cock one last tongue stroke up my shaft, I smiled a bit as I let go of the handful of her hair I’d been using to push head down onto me as deep as it would go into her throat.  Looking down at this girl whom just gave me the best orgasm id ever had, and whom I’d just made the happiest girl in the world with numerous orgasms to each of her tight pink orphaces, reality struck me with an intensity Id never felt. I couldn’t believe who I was looking at smiling up at me, with a string of cum still running from my cock to her mouth, looking up at me with a sexually devious and satisfied grin. This was not Anna, I could have sworn it was Anna that collided with me in the hallway earlier. How the hell did Cali manage to switch places with Anna ? It wasn’t regret that I felt, nor was I apologetic I was absolutely puzzled. “I knew this would happen.” She said to me as we both stood up in the hallway of my house. I tried to reply but I couldn’t, and without any chance to cover up my exposed cock and balls, nor Cali her complete nakedness, the front door came flying open. Petrified as to what they'd think or say after finding out what I just did. It was too late, there we were, awkward and caught red handed by my mom and dad. “oh my god… did you two just… “ my mom began to say, interrupted by my dad, “Are you guys fucking kidding,? Is this a joke? I never once thought you two would ever stoop to that level… not in my household god dammit.” Cali and I looked at each other and as hard as we tried not to laugh, we couldn’t hold back, we both had tears in our eyes having laughed so hard at the situation. That’s when my step-sister began to shake me, “Get up loser. Did you hear me knocking? Yea. That was me, yelling I was saying I knew this was going to happen, been trying to wake your ass up, whoa bro, you got a huge boner right, like, wow, okay. Well. We’re hella late for class, so put that thing away and let’s go.”.


As my sister turned around to leave my room, my eyes locked onto her perky ass, how could I not? She literally spends 25 minutes preparing her outfit everyday in order to perfect how her ass looks. It is absolutely her favorite thing to do in the world, flaunt her butt to everyone including my dad. Id be impressed by anyone who could manage to avoid looking at it while she’s wearing those tight pink yoga shorts. I couldn’t stop thinking of the dream I just had, I couldn’t lose my erection at all, I couldn’t help but imagine Cali coming back in my room and taking off her yoga shorts and letting me eat her tight ass, I’m just fucking horny right now, I need to focus. Tucking my stiff cock into the waistband of my jogging shorts, I grabbed my car keys and my backpack and headed out the door feeling a bit more excited about classes today than usual, I think I’m going to go ahead and ask Anna and Cali both, what they've got going on later, maybe they'd be down to come over and fuck. I guess we’ll have to wait and see.

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Tyga Woods
Tyga Woods
Oct 09, 2023
Rated 5 out of 5 stars.

Got me all hot readin that shit fr fr


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Calysta K
Calysta K
Sep 21, 2023
Rated 5 out of 5 stars.

Dang like sissy be gettin her ass off on the big bro! Itz a hot story though lol ngl

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