“A Stroke of Luck”
“…She looked so good walking around that pool in her white bikini. It wasn’t a thong bikini so it left something to the imagination, which I liked. Sometimes, a little more is better, in my opinion. I don’t know if it was the odd, 88° end of May weather, but I was getting noticeably turned on. I had on baggy swim trunks, which made it easier to hide my noticeable “half staff”. It was easier than, let’s say, me wearing a speed-o. Once again, more is better. I haven’t wore one of those since swim team at my local swimming pool, growing up.
I liked this pool. It wasn’t too crowded, and it wasn’t dead. It was nice. I’ve been coming here everyday after work for about two weeks. I’ve noticed this one particular girl that has been here about half of those days. She obviously lived somewhere within the housing plan that uses this pool along with everyone from my living area. Of course the one thing that stuck out to me was her ass. Damn, she had a nice, tight butt.
I was older, but I was hoping she was at least 18, but I wasn’t so sure. That’s the one thing I’d have to find out first. Anyway, since I moved into my apartment last September, I didn’t get to use the pool. So, over the winter I went to the gym a little more than I normally would of because, for one, it made me feel healthy, and two, I wanted to look good for the summer if I was going to be spending time at the pool, or the beach and what not. Plus, when you feel good about the way you look and feel, you have more self-confidence. Not confidence in a douche bag kinda way, but confidence in a “I feel good”, kinda way.
I had my sunglasses on so I didn’t LOOK LIKE a pervert staring at this girl. With the sunglasses on, I COULD BE A pervert, staring at this girl. Lol. Seriously, tho. She looked good. I think she had the same kinda confidence. Her girlfriends were another matter. Sexy as fuck. Get any guy they wanted, and knew it, in an arrogant kinda way. I already caught the bronzed tan, dental floss-for-a-swimsuit girl, looking in my direction. Anyone, that puts that much into trying to get noticed, I really don’t want anything to do with. Yah, yah, you look pretty hot, but now you took most of the mystery out of ‘what you look like naked’. Wasn’t interested. I was just looking at the blonde haired girl wearing the white bikini.
I kept an eye on her as she walked over to the volleyball court. Her and her girlfriends were just messing around. They weren’t professionals by any means. But who is? Just tossing the ball back and forth over the net, hitting it every once in a while. Giggling. You know, girl shit. I decided to get up and walk around the pool to get a closer look and to keep “myself” at bay, if you know what I mean.
Walking by the volleyball court, I was doing the “side stare” because I was wearing sunglasses, and it looked like I was looking straight ahead. I say again “looked like”, because I ran into some dude, that oddly enough, I believe was doing the same thing. Two idiot guys doing some good ole side staring with sunglasses on, not paying attention to what the eff is in front of them. I’m actually glad this happened because I saw her look over my way and laugh. I sorta looked back over and put my arms up and smiled like “I know, I’m an idiot”….I thought, Yes! “One small step for man”,….you get it. It was the step in the right direction is what I was getting at.
Now, I had a whole huge pool to walk around and think about my next move. I could easily play the bumbling idiot funny guy, but girls don’t really take you serious when you’re that funny guy. I mean, if you are doing it, a woman, I’m pretty sure, likes either the romantic serious type, the raging stallion, or both, when in bed. Not some idiot playing bongos with her ass cheeks or something stupid like that, all the time. So, I did get her attention by walking into that dude, but, now I got to clean up my image a little bit.
As I was rounding the corner I didn’t want to act like an idiot and puff out my chest like some of the muscle dudes here. I mean, what is that? An alpha male thing? No, it’s being a dumbass. Besides, I think some of those lifting dudes do it for the other lifting dudes. Like, “check me out dude. Look at these pythons. I got them doing 3 sets of curls. Breath. Hydrate. Three more. Breath hydrate, annnndd 3 more…go ahead and feel them, no homo…yah, yah, no homo..”. Whatever, I just wanted that fine piece of ass, that just did that sexy as fuck, one finger “fix-my-bikini-before-it-wedges” thing under the back of her bikini bottoms, to stop them from riding up in her sexy crack. Damn. I would do whatever the hell she wanted me to do. “Lick my pussy.”..”I’m already down here.”…”eat my ass.”..”.I got the silverware…”. Anything she asked. Well, 99.9% of anything. (Post it note: never go 100%… have some standards, man…you’re a cool, safe, at 99.9% ??)…
As I rounded the final lap, it all went into slow motion. The sun was in my eyes, but, they were all looking at me, waving, like I should come over or somthi___WHACK!! Yep. Hit directly, IN THE FACE, by, you guessed it, their volleyball. It happened so quick. Why did I immediately put my hands on my nose like it hurt or something? Why couldn’t I have just walked with my body stiff like a piece of iron or something, where the ball would just deflect off my face like nothing happened, and bounce into the stratosphere and burn-up on re-entry…Damn. Like having a Terminator endoskeleton or something…No, had to put my hands on my nose like I just got punched by Mike Tyson, and survived. But, it was just a ball. Her friends were on the ground laughing. Miss white bikini was covering her mouth laughing as she was walking over to me hunched over, reaching out. “Are you okay”…At this point I wasn’t going to admit that it stung a little. No, not where the ball hit me, no, not that at all. It stung my pride a little. I mean the whole pool saw what happened. Even the dude lifeguard made eye contact with me and put his hands over his nose, and shook his head in disgust, then gave a “What was that ‘covering your nose thing’ about?” motion with his hands. Like it was a secret code that men have, or something, that I obviously missed because I was sick that day of “Man School.”
Anyway, maybe it was fate? Who knows, because sexy as fuck, blonde, white bikini chick was walking right towards me,..laughing, but TOWARDS me, just the same. I will take it, thank you! “Gees, are you okay?” she barely got out without busting out in laughter. “From what?”, I said, like a moron. “Haha, from the volleyball hitting you directly in the face,” she said. “Oh! Is that what THAT was? Yes, of course I’m fine. My sunglasses are broke, but luckily my face stopped the ball from rolling into the pool,” I calmly said. I couldn’t believe the girl with that tight ass was talking to me. The girl that I have been stalking for nearly two weeks. Well? Not stalking, per se, I was merely watching her every move for two weeks. “Stalking” is for losers. I was merely, “admiring”, pretty much everything she did…Stalkers are for losers…
After a little back and forth, she put out her hand and said, “I’m Allison.” “Justin” is all I said, shaking her hand. She then invited me over to play some volleyball. After some more people joined in, we played a few games. A lot of fun and laughs. I think I made an impression on Allison. Well, she did ask me to walk her home. In the opposite direction as my place, but I’ll walk that way and then circle back.
I was right, she did live close by. We both went into our respective changing rooms, to shower off all the sand. Every guy knows this, but I must remind them to never think about girls when you’re showering around other grown men. Not that anything happened, but it easily could of.
When Allison came out I think I literally got hard. She was still wet. Her suit was wet, and I couldn’t help but see the outline of her pussy, and the racing stripe of pubic hair thru her suit. So f’ing hot. If she would of pulled down her bikini bottoms right there and said, “Taste me, Justin.” Nothing would of stopped me from doing that, right then and there. In front of everyone. So, I don’t want to get into everything we talked about, but IT WAS flirty. That was all I needed. Since, it was a Friday, she asked me if I could meet her at some outdoor party. Her excuse was, if it wasn’t any fun, by me driving, she could leave without waiting for her friend that drove, to leave. Hey, whatever, sounded like a plan. Oh, she was a Senior in high school. But, she just turned 18, a month prior, and she was graduating in a week. That was all the info I needed!
So, I arrived at the party. It was on someone’s farm. Drunk people and teens everywhere. I went over to the cooler to get myself a soda, since I drove. They had this huge fire burning. I mean, seriously out of control. It was huge. The sun was going down and I wanted to find Allison before it got pitch black out. Out of nowhere someone put there hands over my eyes, “Guess who?”, I heard. Before I could even guess, she jumped out in front of me and gave me a big hug. Naturally, it was Allison. She looked beautiful. Sexy as can be. I can’t believe a few hours prior, I never even spoken to this girl, now she was hugging me? Awesome. We were with each other from that point on.
We walked around the farm, talking. Until I stopped and kissed her. I could tell she was waiting for that. She put her hands on my face and kissed me right back. I put my arms around her tiny waist and I couldn’t help but touch the one thing I have been wanting to touch. Her perfect ass. I was right. It was firm, and tight. She seemed to kiss me harder when I did that. Then she stopped, looked directly in my eyes while still holding my face, and said, “Justin? Do you want to leave?” “Sure” I said quickly.
Allison just ran and told her one friend we were leaving, and off we went to find my truck. It was only, like 10:00. I was thinking maybe this night is just starting.. I couldn’t have been more right. She held my hand while I was driving, looked over at me, and smiled. I was thinking, “who WAS this girl I was with? Why did she seem so into me? I mean, that is awesome, but, it seemed like we’ve been seeing each other for a few weeks now, or something?” I guess it didn’t really matter, we DID talk a lot, and covered a lot of things in the short time we were together. I liked it. I was fine with it. All of it.
She wanted to go to my apartment (which was more of a “townhouse” than actual apartment), because she had told her parents that she was staying over at her friends house. How in the FUCK was all of this happening?!
When we got inside, under the light, you could see that we both had mud all over the bottom of our pants. Some of the ground on the farm was was soggy from a rainstorm we had a few days earlier. I said the only thing I had was sweatpants or pajamas. She wanted the pajamas. So, I got her a pair of flannel pj’s and showed her to the bathroom upstairs. I just put on sweats from the laundry room.
Allison came down after a few minutes, and when I saw how f’ing sexy she was wearing my flannel pj’s, I just wanted to jump inside them with her. There was that familiar feeling again. I could feel that my dick was waking up. “I guess I’ll just have to stay over tonight, now that I’m ready for bed, hehe”, she giggled. “Well, I guess so”, I said as I asked her If she wanted to get comfortable on the couch. I turned the tv on to one of the movie stations. Just needed some back ground noise. We started talking about sex (imagine that), she brought it up. I figured I wasn’t going to lie about anything, I think she seriously wanted to know how far I was willing to go. I told her, “It’s not really about the sex so much, for me, anyway, it’s more important for me to have my partner enjoy our time together, and have an orgasm.” There it was. The magic word. “Orgasm”. Allison’s eyes lit up. “I’ve had sex a few times, but not enough, or with a guy that was experienced enough, to even come close to giving me an orgasm. I thought it was just me. I thought THAT IS what it’s all supposed to feel like”, she said, with a hint of hope in her voice. (…me➡️…?)
I went on to tell her pretty much everything, you all reading this, would predict that I would of told her. I even went as far as to tell her some of the most explosive orgasms I have personally witnessed was during anal sex. She just laughed. She thought I was joking. As you all know me, I was not joking. I could see her mood change. From quirky teen girl, into a woman that needed to feel what I was offering. You know, thinking about it, I’m POSITIVE Allison would of emailed me a sexy pic of herself…just sayin’, girls…be like Allison…(me, again..?)
As I was talking she was curled up next to me, just saying “yeah, or ok”, sorta staring at the side of my face. Thinking deeply. Wanting something. Allison then took my cheek, and placed her hand on it, and moved herself from beside me, to over top me, cupping my face and proceeded to kiss me, while sitting on my lap. Her tongue felt so good with mine. I didn’t want her to feel I was taking advantage of her, so I whispered, “How far do you want me to go, Allison?”…”I want it all, Justin. I want to feel what all those other girls you were with, felt. ‘All of it’”, she said, with the last part being a direct consent to everything I said. ?.
I can actually remember, while we were kissing, what I was actually thinking at that particular time in my life. I just remembered how a couple of guys I worked with didn’t believe me when I said that I did anal all the time. They laughed. It was true. I don’t know how I get so, quote, unquote, “lucky”? I just do. I actually remember thinking that. That’s probably why, while she was over top of me, kissing me, on her knees, on the couch, I decided to move my hands to the only thing I could at the time. Her ass. I grabbed her sexy as fuck ass and began to squeeze it. Allison didn’t seem to mind that. So, I put one of my hands down the back of her pj’s. I got a full erection. Especially when I noticed she wasn’t wearing any panties! She must of purposely left them up in my bathroom. So hot. So freaking hot.
She started to grind her pelvis on my dick underneath my sweats. I put my other hand down the back of her pj’s. Now, I was caressing both her asscheeks. As I was separating them with my hands, I took one of my fingers and just glided across her asshole. Her ass felt good back there. Allison stopped kissing me, and with her eyes shut, she put her head up to the ceiling and said, “Oh, yes.” I think she was speaking matter-of-factly, not directed towards me.
I could feel her pussy getting wet from behind. I started to finger her. “Mmm, yes.” She let out with a smile on her face. I still could not believe that this ass, that was in my hands is the one I was checking out earlier at the pool. Un-freaking-believable. Maybe I am lucky? At this time her pussy juice was all over my fingers. I took two fingers and sorta guided some of that wetness up the crack of her ass. Getting her tight little bum hole lubed up. My middle finger just circled around her anus, teasing her. Allison started to wiggle her ass in hopes that my finger would slip in there by her movement. No, no, no. Oh, I had other plans.
“Do you want me to taste it?” I whispered. “Yes, oh God yes” she answered back. She got off of me. I got up off of the couch and took off my sweats, only to show my huge boner coming out the fly of my boxer shorts. I tucked it back in. Allison had a look of surprise or lust on her face. Whatever it was, it was a look of “I want that”. I could understand. She did tell me she only had sex “six times”, so, I guess, seeing an erect cock, wasn’t something that happened every day for her. She was a young girl, with a woman’s body, wanting to be that woman. And I was going to do anything and everything I could to make her feel that way.
I told her to lie back on the couch. My couch had an extra piece, an ottoman, in case someone wanted to lie down in that direction. I gave Allison a few couch pillows to put her head on. With me, on my knees, on the floor, I took Allison’s ankles and began to shimmy her pj bottoms off. Oh, my lord. The most beautiful pussy. Mmm. I went right for it. I softly licked her inner thigh, working my way up to the top of her perfectly shaved short racing stripe. I thought to myself, “yep, she is a natural blonde.” I teased her for a bit, until I guided my tongue and separated her pussy lips with my tongue. She had an “innie”, if you know what I’m talking about. She tasted wonderful. She was wet down there. I opened her up with my fingers, as I found her tiny clit. I began to lick the hell out of it, while I moved my finger in and out of her. She was moaning. She grabbed the top of my head by the hair. I could tell I was driving her crazy by her trying to pull my hair out. I didn’t mind though. Made me feel I was doing a good job.
After a few minutes, she was sopping wet, and I knew she was ready for something else. I moved a couch pillow next to her, and helped her roll over onto her stomach, with the pillow perching her ass up. I got in between her legs, and just like her pussy, I teased her whole area with my tongue. Softly biting her ass. Spreading her ass. Taking my tongue up and down the crack of her ass, have her jolt her body, every time I went over her wet asshole. Enough with the teasing. I started to circle the outer part of her soft anus. I was driving her nuts by “not” touching the center of her anus with my tongue.
Then I went for it. Circling round and round, getting closer to the opening with each lap until finally I stiffened up my wet tongue and dove into an area where no tongue, or dick, for that matter, has, EVER, gone. What a privilege for me. But, I didn’t want to fuck up any of these firsts for her. I know I was doing a good job because Allison kept sticking her ass up while my tongue was in her, spreading her ass, to get me to go deeper. She was breathing heavy and talking dirty to herself. I loved what I was doing to her.
I was tonguing in and out of her ass. Yes, in and out of her ass. For all of you that find that sick. Then again, why would you even be reading this..I could feel Allison relaxing her muscles as my tongue found it to be easier. I would stop every once in a while, and since she was spreading her ass open, I would quickly rub the inside of her pink exposed asshole, with three fingers dipping in her slightly. So soft. Silky. She seemed to love that.
Ladies, do you like that, or would you like that? PM me. Ha. Seriously, tho. I like to say, “I’m the nicest guy you’ll NEVER meet”…. Anyway, at this point, I had taken off my boxers, and decided that I wanted to enter her vagina, from the rear.
So I moved myself towards her ass, while on my knees. I had to get up a little to guide my cock inside her. Allison moaned with pleasure as I wiggled my dick to find the opening and slowly slid it in her. “Mmm” is all I heard. I started out slow, but after a couple thrusts, I was going pretty quick in and out of her slick pussy. She really got into it when I began to finger fuck her ass. Twirling my finger around in there. I switched to my thumb, and put it in and then pulled it out, giving her pleasure from both her holes.
Her ass was perfect. She wanted something in there and I think she was prepared mentally too. Her asshole was so relaxed, even though I was pummeling her pussy. Allison was really getting into it. Calling out the all mighty lord, and also saying the eff word over and over. I stuck two of my fingers in her ass, and with one, I felt around the rim, from the inside, underneath.”Oh, oh god, Justin, keep doing that, oh god, don’t stop, I think I’m going to cum, oh god. I love it” she was partially screaming.
A couple more pumps and she squeezed her ass cheeks, and jerked her body, as she came all over my dick. She was loud at that moment. I slowed down and took my dick out of her, as she just was breathing really heavy. “JUSTIN, you made me cum, oh, shit, I never felt something so amazing..holy shit, it was amazing.. Oh, Justin, I want your hard cock so deep in my ass..Please,…Please.. I want to cum from my ass..” she gratifyingly said.
You know, I will always love to hear those exact words. It just really turns me on. I looked over Allison’s 18 year old ass. Dang. Wow, was I lucky, I thought again. There she was. This beautiful girl, I happen to see a couple weeks ago. Finally meeting her earlier today. Thanks to a flying volleyball. Now, here she is on my couch, spreading her ass, that no other guy could get her to do, before me. And here I really am, typing something that happened a while ago, and bringing it back to life on Reddit for YOU to read..Yes, another anal story, but, that’s all I got worth repeating.
(Ok, Unpause)…I could tell that Allison was serious. She was fingering her ass wildly, pushing her pelvis down against the pillow each time she went in. Her ass was still perched up in the air. I asked her if it was good in this position, she agreed. I moved up. My dick was rock hard. Just dripping. I bounced the head around her hole, circling it, going up and down, putting pressure, and then like that, it just slipped right in. I was going further in, slowly..It was just disappearing. Like a tractor beam pulling in the millennium falcon (??♂️ it’s late at night ok?). Inch by inch. Nothing hindering it.
Allison was going crazy, “ohhh, mmm, ahhhh”, not really saying anything, just making noises, biting her bottom lip. As soon as I got the whole way in her ass, I started to come back out, prolapsing her anus, a little. It didn’t want my cock to leave. Gripping it, but it was too slick. Extremely hot. From other experiences, I know it feels wonderful coming the whole way out, but it just makes it harder to get it back in after her backdoor closes, so, I could feel the head of my cock reach her sphincter muscle. I would go just a little more, then back in, all the way. The view is amazing. The feeling was even better.
Allison was breathing heavy, and started to rub her clit. The pressure all around my dick was so great, it was very hard to not cum yet. I knew it wasn’t going to last much longer. I started to penetrate her faster. In and out. The lining of her anal canal was so smooth. My dick had no problem at all going in and out. Her asshole would follow the contour of every vein, every bump of my cock. That’s how tight it was.
Wouldn’t the world be a better place, if everyone at least tried anal? This way? I wish. I started to really let her have it. She was screaming for me to destroy her ass, so, I had to oblige. Allison’s legs were partially bent, shaking, because I was actually plowing her up in the air too high to kneel, so every time I slammed into her her feet would bounce up. She was getting ALL of me at this point. My balls were slapping up against her wet pussy. She just put her head into the pillow and enjoyed the ride. She was making no sense at all. All I heard, besides my balls slapping, was a bunch of Fucks, Me’s, loves, God’s, Jesus’s, probably the 12 disciples, and whatever else.
Who knows what she was saying, but she was enjoying it, as was I. In and out, I went. I tried to hold it in as long as I could, but I could feel it building. Just looking at my dick going in and out of her stretched asshole, thinking about that same bubbly ass in that white bikini, was more than any man could take. Allison was telling me “Oh, Justin, please don’t stop, I am cumming!” I didn’t as she squirted all over me, my couch, and the floor. I didn’t care, two more pumps and I was cumming in her ass. “Oh shit, oh Allison! Uhh”, I exploded midway thru a thrust. Cum shot out the sides of her ass and made its way into the floor to mix with hers. Holy shit I came! A lot! It felt like my balls were vacuum sealed. Instantly drained, emptied, and essentially, shriveled up.
Allison was moaning, I was breathing heavy. My dick pulsated inside of her ass. Cum all around her opening. I pumped her a few more times. We both felt very sensitive on or in our sexual parts. What a freaking orgasm. I think my eyes rolled the whole way around, and reset. I just put my arms around Allison and tackled her onto the carpet while I stayed in her. I softly kissed the back of her neck until I leaned up and turned her cheek and really, really kissed her. Once again, her tongue felt so good with my tongue. Life was good.., until the morning…..Then, it was great…?”….
Well, I really hope you read the whole thing. I have a lust-filled story coming up tomorrow. Just let me know if it turned you on at all. I love to hear that, as you all know.
Source: reddit.com/r/eroticliterature/comments/d6jkn4/a_stroke_of_luck_mf_long_anal