“The Much Needed Family Vacation” [long] [story surprise] [anal]

Story taken from a man’s POV. ?
“The Much Needed Family Vacation”
”Her ass was so young and tight. I could tell by how much I have been paying attention to her everyday for at least three years. She was so sexy, but, oh, that ass. I don’t even think she knew it. I mean I know she knew she had a nice body, but not on this level, to me. I’m pretty sure she didn’t know about me, thinking of her, in this way. Every guy that saw her probably whipped their dick out in their bathroom only to jerkoff imagining that they were sticking their dick in that perfect ass, and filling it up with their cum. I wonder if her boyfriend, and ex boyfriends got to taste and fuck that ass. I actually wonder if she likes it back there. You’d think she does, by the way she presents it. The skimpy tight shorts, skirts and pants.

I was actually able to take a picture of her pussy staring back at me from under a table. I was shocked to see that she wasn’t wearing any panties. I drowned that pic with the amount of cum I expelled jacking off to it. Regardless, if she was really into anal sex, or not, in my fantasy, she was.

She does a lot of modeling for local stores. Modeling bikinis, clothes, watches, etc. EVERYTHING, just made her more fuckable in the minds of so many. But, mainly me, I’d argue. Her name is Kristen.

God, I just wanted to taste her. I know it’s wrong. I fight with that constantly. But, everyone has a breaking point. I can’t help that everything I ever wanted in a woman, was right there, in front of me, all the time. She’s 18, and a senior in high school. I’m two years older, and I go to Community College. I made a fake Instagram account, to look at her pictures and beat off to.

I was silent, I didn’t comment on anything at first. Then she went private. I couldn’t see any of her new pics, so I added some basic pics that I know she likes. I put pics of dogs, cats, actors, actresses, flowers, and a bunch of other stuff, that might catch her eye when I requested to follow her. She accepted me! There, she was. I know why she went private. She started to get a little more risqué with her pictures. Sitting at the pool, with no top on, holding her hand over her perky tits. Damn, I wanted to see them too. I am so in love with Kristen, and she doesn’t even know it.

She started liking things that I said on her IG page. Then she started commenting on posts of mine. After a few weeks we were sending DM’s to each other. She wanted to know what I looked like, but, I told her I could never do that, ‘someone’ would find out, and get upset with me. Over the course of a short period of time, I fell into complete and utter love, when she started sending me provocative photos of herself. I told her that I was “the nicest guy, that she’ll NEVER meet.”..I’ve said that phrase over and over to her. She started sending me videos of her trying on clothes and things like that, which I couldn’t help but blow a load masturbating to. I told her, I really liked her, and I wanted to really kiss her. She liked that, a lot.

We really got to know each other, and she obviously really liked all the things that I said to her, as if “we’ve known each other for a long time.”.. like she said. One of the first problems I had was that my girlfriend, was her best friend. They did everything together. Even if my girlfriend and I would go out, Kristen would tag along, maybe with someone she was dating, or not. She was always there. Not, that it bothered me.

I know, I already said it felt wrong. But, why should you hide your true feelings? I bet her pussy smelled so good. I wanted so bad to find out. I wanted to pleasure the hell out of her. My family took a family vacation to the beach. My girlfriend came, So did Kristen, all by herself. She was thinking about staying home, but, she came. What is so cool is my girlfriend would never expect that I would be checking Kristen out. Ever. I just know that. She knows how wrong she’d be by saying such a thing.

So, Kristen came to the beach by herself.
No guy. I already had dirty things in my mind. We would go to the beach, and I’d have my mirrored sunglasses on so no one could see my eyes, while I was checking out Kristen’s tight little ass, with her bottoms pulled up over her cheeks to get more of a tan there. So many times I wanted to say something but my girlfriend was always there. So, I thought up a plan…

I went online, logged into Instagram, and took pics of our vacation. Not, anyone she’d know, but tourist attractions, the ocean view, the lighthouse and so on. Then I posted the pics. I waited in my room with my girlfriend. Kristen, immediately started to comment, “OMG!, you’re here too! We have to meet up!”
That got me nervous, but, I did it, for that reason. I knew the next day, the family was going to some museum. My girlfriend was going. But, I was on dinner duty, so I was staying back. Plus, Kristen was staying back because she already was at the museum before. This would be my one and only chance.

The next day couldn’t come fast enough. My Mom and Dad told us not to fight. What?! I thought? How old are we? Fight. Really. Whatever. My girlfriend just laughed. For some reason, as I mentioned, I had her so fooled thinking I’d never want to fuck Kristen. So naive. They all left. Kristen said she was walking to the beach. I told her that I’d be there in a little. I know she was going to meet her “Instagram man”. I know she was. She took a long shower before she left. Probably wanted to get everything clean ‘just in case’ she hooked up with him. This got me hard.

I walked down to the beach. There she was. I had to go talk to her. I had to tell her how I felt, and who I was on Instagram. This could be tough . Damn, I love the way her bikini was riding up her ass crack. I’d gladly “unwedge” it for her,…. with my teeth. Lol. Alright, This was fate. This was MEANT to happen. She has no idea who I ‘really’ am. Well, of course she does. Just not my Instagram alter ego.

You would never guess it, by the persona she has on social media. Like a “good” girl. Hey, you can love having a cock in your ass, or being filled up with hot cum, and STILL be a good girl. It’s just the world’s stigma that makes it seem slutty just to enjoy pleasure. It’s pleasure… What’s so wrong with that? Nothing. But, if she doesn’t want her thousands of followers to know that, then I respect that. She has total anonymity with me. Problem is, she only READ about “him”, she has no idea it’s actually me.

I know she liked to show that ass to thousands upon thousands of followers on IG. I also knew that she was either into assplay, or, at least, curious about it. I didn’t know, but I was determined to find out… I couldn’t take anymore of this staring. Even with my mirrored sunglasses on. I was sitting right next to her. She was comfortable around me, too. She’s always been that way.

I asked Kristen if I could use some of her suntan lotion. She said, “Sure”. When she saw that I was having difficulty putting it on my back, she said, “here, I’ll do that, silly”, and she put it all over my back, and even ran her finger on the “inside” of the back of my swimsuit. Instant wood. Yep, I got hard. I had to cover. So embarrassing. I couldn’t help it, she was just so fucking hot. Why was I thinking like this? I wanted her to lay down, so she wouldn’t notice my huge erection. I know other people on the beach saw it, but, I’m sure they understood, looking at who I was talking to. When she did go on her stomach, I half jokingly, half seriously, said, “ok, my turn to put it on you.” It was like slow motion when she said those magic words, “Okay”, which sounded more like, “Ooooohhhh Kaaaaaaay”. That turned me on so much, that unwittingly, I straddled her. She just giggled. There was the girl I knew. I was trying so hard to turn her on by simply putting suntan lotion on her back, but it wasn’t working. Because in my head, touching her back was sending signals to her vagina, saying, “take me”. That was not the case. My dick was so hard. I so wanted to separate her ass cheeks and shove my tongue in there.

Ok. I was done. I couldn’t stay with my cock an inch away from her ass, she was eventually going to say, “Ahh, I think you’re done..” So, as I was getting off her my tip grazed the back of her ass. Kristen turned her head, but not the whole way to see it. She just put her head down to catch some rays.

Then a gift was given to me, a gift like no other, it came my way by her saying, “you know, I was hoping this guy would show up here.” Kristen stated. “Oh yah”. I said, acting stupid. “I don’t think he will. I never even got to see his face, but I want him.” she clearly said. I said, “ Well, what about that guy?” Kristen lifted her head, and looked in the direction I was pointing. “No, not him” she said, putting her head back down.

“Well, he could be a nice guy, but apparently he’ll be,…THE NICEST GUY YOU WILL ‘NEVER’ MEET”,… Ohhh gees. The cat was out of the bag. My Instagram alter ego used that phrase so many times, and Kristen, knew it…Her eyes opened up wide. She blushed. It must of all started to click. “Steve, are you familiar with SW2FK?” Kristen asked…Yes I do, but, there is a reason!” I said, as Kristen just looked at me and ran back to the house crying. Oh, Shit, I thought. What the fuck just happened? I thought. Oh, SW2FK was my Instagram name. It means, ‘Steve Wants 2 Fuck Kristen’ Real original, huh..

I got back to the vacation house. Kristen was sitting on the couch. Her eyes were all puffy from crying. She came running towards me, and started hitting me on the chest, “You fooled me?! Why did you fool me?! Why?! Why would you do such a horrible trick?!” She said putting her head on my chest crying.
“I wasn’t ‘tricking’ you, Kristen. That’s the last thing I wanted to do. Everything I said, The feelings I have for you. It’s all true. I don’t want to hurt you, I want to love you,” I said, opening myself up to her for the first time in my life.

“Really?…You really meant it all?” Kristen said, looking at me in a completely different light.
“Yes, ALL of it. I know you’re my sister, but, I just can’t help myself, I find you so damn sexy. All of you. Not just your body, but ALL of you” I said, truthfully. Kristen got a huge smile on her face. “I have thought the exact same way about you for years now.” She said. Now, I had a huge smile on my face. My cock got hard, and was poking in her tan stomach. “Well, maybe I should take care of that” Kristen said, grabbing my hand and leading me up to the Master Bedroom of the house.

She untied her bikini top, and took down her bottoms. She looked fucking amazing. Her teenage body was the best I have ever seen right before me. I pulled my shorts down, and took them out. My 8” cock flopped out. Kristen’s eyes just got huge. She just stared at my penis…she looked at it in wonder and amazement. She blushed. She said, “It’s, it’s bigger than I imagined, bigger than any of my boyfriends I have had.” I took that as a compliment. I guess. I mean, what if her boyfriend had a micro-penis or something. Yes, stupid, pointless things always pop in my head. I didn’t know if she was serious, for one.. For two, I don’t think she knew she started to rub her pussy or not, when she said that..

I had a good amount of pre-cum on the tip that made for good lubrication as she grabbed the top and started sliding her hand up and down twirling her whole palm on her way down, causing an unusual but fantastic sensation on the tip of my penis. “Do you know how bad I want this? I’ve fantasized about this.” She said. Damn, do not cum, is all I thought. I could not blow this opportunity. No pun intended. I was going to make it all about her. Trust me, it would be hard for any guy, to NOT blow a load, being alone with someone like her, and she was my sister. We’re so bad. We’re so dirty. We both knew this was wrong, but nothing could stop the love we have for each other. It would take sheer will power. I WAS NOT one of those guys. We all have weaknesses. My sexy teen sister is mine. ..

While she was pulling my cock, she put her hand down in front of her, fingering and rubbing her pussy and her clit. I could see and hear her wetness. I couldn’t take not doing anything, anymore. I had to stop her. This wasn’t about me. I wanted her to scream with every pleasure, with what I had in mind for her. I spun her around. She stuck her ass out towards me as I leaned down. She turned her legs inward, spreading her sweet ass a little. Damn. There it was. In full view, for the first time. All the times I would of paid to see this, it was right in front of me. My sister’s right ass. Damn. Her ass WAS perfect. Her asshole was just begging for attention.

I wasn’t going to waste any time. I ever so gently started to lick up and down on the inside of the crack of her ass. Every time I’d go over her tender asshole she would quiver and moan. I COULD TELL the guys she was with, never did “this” to her before. I circled my tongue around the outer perimeter of her eager hole. Kristen was moving her head up and down, eyes shut, and her hands spread out on the wall.

I lathered her asshole up so good with my saliva and her tangy ass sweat. She was going crazy. Her muscles in her ass were pulsating. It was tough to get my stiff tongue in there, but I managed. Spreading her ass with my hands I made stiff circles inside her, lubing the inside of her satin walls just as much. All the while opening her up for what she was eventually going to receive. My stiff hard cock which was going to gape her ass wide open. But, for now, my tongue did all the exploring. I cleaned and naturally lubed every little crevice of her opened pucker. This is what she wanted. She repeatedly kept saying.

I really was rimming her hole, as I curled my tongue, and rimmed her asshole from inside. A reverse rim job, if you will. Kristen kept crossing her knee over her other leg, like she had to pee. But, this was not the case. She just loved it so much, and couldn’t control herself. Some people may say sticking your tongue in an ass is gross. Well, I call it love. I call it pleasure. There’s a reason you have so many muscles and nerve endings back there. Actually more muscles than a vagina. It’s pleasure. Pleasure is not gross. Some people will do anything to please their partner with new things…

My sister’s asshole was really sloppy with my saliva. I’d take my tongue out only to put my middle finger in there and spin it around. She loved it. She started to buck her body, making out the words” I want your cock in there, Steve…” I shifted her butt up towards me to give me the best trajectory of my tongue burrowing in her little tight ass. She was moving her sphincter muscles in and out, which only turned me on more. I looked down at my cock, only to see it had a glow to it from all the natural lube and the sunlight coming in this big bedroom.

Kristen reached around and was running her fingers thru my hair. She was moaning with pleasure as I ate her ass. I was about to cum from just doing this to her beautiful pussy and asshole. I had to give her pussy some much needed attention. I stood up, picked up her fit, tiny body and put her on her back, on the bed. I wanted to see my sexy younger sister’s face when I eventually fucked her. I went down to taste her sweet nectar on her pussy and play with her clit with my mouth. I began to finger her with my one hand, as my other kept the rhythm of my middle finger swirling in and out of her tight ass. One finger at first, then two, and finally three, gliding in and out of her pussy, rhythmically in sync with my tongue. I held her clit gently in my teeth, then I’d release it, only to catch it by sucking. Sucking on it like a lollipop.

My face was completely wet. Licking at speeds I didn’t even know that I could do with my tongue on her clit. She was pulling the sheets in fists of pleasure. I could tell she couldn’t take much more as she erupted; her pussy clenching tight around my fingers. I could see her asshole puckering along with her orgasm as she moved her legs and body all over the bed. “Oh, fuck my ass, fuck your teen sister’s ass! That’s all I want. Fuck my ass…I never wanted something so bad, and naughty. Put your cock in your slutty sister’s ass! “ Kristen said in pure lust. I couldn’t agree more.

My cock was like a hair trigger just ready to go off. I really had to concentrate to make sure this didn’t happen. I flipped her over on her stomach. Her ass looked so fucking good, I couldn’t help but go down for more and relax her hot hole. First, I put a pillow under her to pick that little cheerleading ass up. There I went. Diving back into her ass with my tongue. She grabbed and spread her ass cheeks. “Oh, God,” she muttered. I plundered her anus with my tongue. Fucking her. Loosening her up. Cum was still all over her inner thighs. Her clit was so sensitive as I reached underneath her and she completely shuttered as I barely touched it. I swirled my tongue round her ass, probing in and out, until I knew, not only her, but, I couldn’t hold this erection much longer. I had to put it in her warm gooey hole.

I moved my body up, with her legs together, turned inward, spreading that lubed up ass right beneath my dripping cock. The veins in my dick were so defined knowing how hard it was and where it was going. Here it was. What I have dreamt. What she had dreamt. Spreading her asshole with my two thumbs, grasping her ass cheeks in my palms, I pressed my cock on her soft anus.
Gently, I pushed my way in, without any hesitation, her ass just swallowed my cock. Damn. It was so tight. Damn I loved this. Damn, her asshole looked so stretched, as I dug deeper into the abyss. My little sister had such a tight ass. I couldn’t believe I was finally fucking my little sister, and she was allowing me to fuck her 18 year old hole.
Finally, I reached the end of my shaft. My balls rubbed up against her warm pussy. I was all the way in. I could not believe who I was doing this to. Looking down, finally seeing her naked ass, and finally seeing my cock, balls deep in her most private of holes. I could no believe her tight ass stretched to accommodate me. She shuddered again as I started rubbing her clit.
I pumped my thick cock in and out of her slippery ass. “Who’s fucking your ass?!” I sternly asked Kristen. My older brother, this little teen’s older brother!” She replied.
“I want to fuck Dad too! I want to fuck you and dad together, in my cheerleading outfit, with no panties on! I want you both to stretch my little asshole out!” Kristen, surprisingly said.

I moved my hand back up to her ass. I loved watching, holding an ass cheek in both hands as her sphincter widened and tightened along with the motions. I knew this would not last much longer as I really started to fuck the hell out of her. The easier it felt on my cock, the faster I went. I’d pull out just to see her beautiful asshole opened up showing the satin walls of her anus, only to slowly begin to close, just to plow into her again. She was hysterical. All these visions of all these prim and proper pics entered my mind as I slammed the shit out of her ass. It was so fucking hot. Each thrust seeming to gain more momentum than the last.

She moaned, high pitched and breathless, never having been pleasured like this before in her life. I could see her inner thighs getting wetter and wetter. She was screaming, “Oh, God, don’t stop! Keep going! Almost there! Shit…Fuck my ass, Steve! Fuck me! Fuck me at home in my room when Mom and Dad are downstairs!” She let out in the heat of the moment.

I could tell she was nearing a second orgasm, and I kept going a few more pumps as I felt all of the blood rush out of my head as I exploded in mid-pump, pushing my newly discharged cum deep into her anal passage. I pushed my body weight into my sister’s previously never been fucked before, ass, as I finished cumming somewhere, so fucking deep in her beautiful ass. Probably in her stomach. Her asshole tightened up around my cock as I felt a flood of juices rush down my thighs. Her ass milked my cock with spastic pulses. It seemed to be endlessly squirting. She was panting,
cum oozed out along the sides of my dick still in her ass. It looked wonderful.

She put her hand back there and caught a lot of that cum in her hand and on her fingers and put them in her mouth and sucked them clean.
I could of came again witnessing how unbridled she was. So fucking hot. I slowly pulled out because my dick was so sensitive at the head. Her ass stayed open, cum just pouring out. Both of us were totally spent. I just collapsed on her and spun her on her side and spooned her, naked as we both took a much needed nap… together, but not for long.
“THE END”

Yes. I’m just as horny as every one of you reading this. If this story got you wet, or you liked it, I would love to know about it. You see, that’s what turns me on, turning you on. I’d love to hear from everyone. Message me if you want to remain private, or email me if you have a little something for me. It never hurts to ask! Well, I hope you liked it. Take care. Love you all! ?

Source: reddit.com/r/eroticliterature/comments/ddd1em/the_much_needed_family_vacation_long_story