I remember every little thing as if it happened only yesterday. It was the day I lost my virginity to my big sister.
I came home early from school because Mrs. Halsey had a heart attack in class that day. Most of us weren’t aware of this because we were working on a separate assignment in the back. But when other teachers, and a little later our nurse, came running and we were directed out of the classroom through the window, we all knew something was up.
We all gathered in the cafeteria, where the principal talked to us about what happened. He also told us that we were free for the rest of the day and allowed us to go home.
It was just a twenty-minute walk from school to my house, and I knew I’d be home alone for the rest of the day. So when Mr. Deacon offered to call my parents, I told him it wasn’t necessary because they’d be at work anyways. But he called them nevertheless, and after explaining everything to my mother, he handed me the phone.
“She wants to talk to you, Brett,” he said, handing me the phone with a knowing smile.
I held the phone to my ear, and the familiar voice of my mom said, “Hi, sweetie! You okay?”
I explained I was fine and that I was about to go home. It wasn’t a surprise that she had to stay at work, but I didn’t mind that at all. Mom gave her the usual speech about being careful, and she insisted that I could call her when I wanted to talk about what happened today.
Mom and dad both had very demanding jobs. My dad was the CFO of a big company specializing in corporate finance, and my mom was a manager at a pharmaceutical company. Both worked long hours, but they never neglected my sister or me. They were home almost every weekend, and at least one of them was home to cook and eat dinner with my sister Hailey and me every evening.
Still, my sister and I were home alone a lot. Up until about two years ago, we had a nanny who was always there and basically ran our household during the day. But when she was asked to come and work for some famous person, Dad asked me, because I was the youngest, if I wanted a new nanny.
I had just turned eleven and felt all grown up when my dad asked me what I wanted. Of course, I thought I didn’t need a nanny anymore. So Mom and Dad threw her a small farewell party, which was pretty emotional, but we also laughed a lot during that party. She told my sister and me how big we’ve grown and that it was the perfect time for her to get a new job. She’d miss us, of course, but she promised to stay in touch. So after we said farewell and a few final hugs, I was nannyless.
And that was it. Whenever I came home from school, I came home to an empty house. Unless my sister was home already, but usually, her schedule was different from mine. And she usually had her cheerleader practice three times a week after school. At first, it took me a little getting used to being alone, but my sister helped me out with a few good ideas and pointers on how to do things right. So after a few weeks, I didn’t know any better and even liked the freedom and responsibility.
During the walk home, I was contemplating my options for the day. We were cleared from homework, which was a big plus, and my sister Haley had her practice after school. This meant that I’d have the entire day to myself.
I turned up the volume of my Beats when the latest Foo Fighters song started playing as I rounded the last corner toward our house. I already figured out that, because there’s no way I can be caught or interrupted, I’d start with a slow jerking session in my room. I’ve already downloaded a few new vids of big-breasted women surrounded by six or seven guys, where she’s alternating between them, sucking and jerking them off. They always end in the women being covered in cum. This was my latest go-to type of vid to get off on. I didn’t know why, but this combination somehow turned me on immensely and always got the job done.
As I inserted the key in the front door, I already felt my dick chub up at the thought of these vids. I also wanted to hop in the jacuzzi that was installed two weeks ago. My dad really put out on this one. A six-person-sized spa with a TV which slowly rose from a hidden spot at one end of the jacuzzi.
Before I went upstairs, I checked Hailey’s schedule on the fridge to make sure I was right about being home alone until around five this afternoon. Seeing I was right caused my dick to quickly stiffen to full mast, and I practically ran up the stairs to my room.
I pressed the power button on my pc, and as it started to boot, I took off my shirt and pants. I looked down at my tented Under Armor boxers, feeling proud at how much I’d grown down there over the last year. In the shower after basketball practice, I learned that I was one of the bigger boys on the team, despite being almost the youngest. Of course, it helped that I didn’t have a big, bulky build like most guys, so my dick looked even more prominent. I was a good five inches hard, and it showed when I looked down.
As my login screen appeared, I slid down my boxers, sat down on my gaming chair, and sucked in a breath as my skin hit the cold leather. But I hardly gave it a second thought as I immediately started searching for the recently downloaded videos.
Before I knew it, the woman was sitting on her knees, surrounded by six men, all pointing their hard dicks toward her face. It amazed me that all the guys needed to keep jacking themselves in order to stay hard. I knew for sure that if I was one of them, I’d stay hard no matter what.
I had to hold back a little because I wanted this session to last. However, as she sucked on the guy with the biggest dick, I felt my balls starting to boil, so I had to let go for a moment. This happened a few times, making it increasingly difficult to hold back. But I knew the end was approaching, so when the first guy started squirting all over her tits, I started going at it for real. I kept looking at the squirting cocks coating the woman in cum, and somewhere between the fourth and fifth guy, I felt my balls contract.
The two last guys emptied their balls over the woman as I felt the cum leave my dick and splatter over my bare chest. By now, the woman had her mouth open and extended her tongue to catch some of it in her mouth. My orgasm kept going during the ejaculation of the last two guys, and I felt a bit drained when the camera panned over the woman, showing how much was covering her. She giggled coyly into the camera, and moments later, the clip faded to black.
I sighed deeply and checked out the mess I had made. Lately, my watery cum had become a little bit thicker, but I was nowhere near the stuff I saw in the videos. It didn’t matter much to me because it was easy to clean, and I knew it would only take a little time to shoot the real thick stuff.
I grabbed the towel I kept in my desk drawer and started cleaning myself. After I was done, I got up and walked over to my dresser to grab my swimming trunks. My dick had gone down by now, which I noticed as I walked past my full-length mirror. I always checked out my dick in the mirror when I got a chance. I didn’t know if it was normal, but I couldn’t help myself. It was the same as in the showers at school. If I saw a naked body, I had to look.
I stopped in front of my mirror to take another good look and to check if I didn’t miss any cum, which would be uncomfortable when it dried. I moved a big lock of hair out of my face and checked out my shoulders. They had broadened over the past few months, and all the basketball practice was clearly paying off. Looking at my face, I realized that my dark-brown hair needed a trim if I didn’t want to start looking like some goth.
I hated the freckles around my nose, but Mom insisted it looked adorable on me. Of course, I know moms aren’t unbiased as a judge of their own kids, but I heard some girls in school whisper to each other that I was a cutie, so Mom was probably right about this one.
As I looked further down, I felt proud about my tight belly and the small patch of black pubes above my dick. Despite my five-foot-two frame, my three-and-a-half-inch soft dick still looked big because it was a bit thicker than my classmates.
After brushing my fingers through my pubes for a moment and glancing at my body one last time, I pulled up my trunks. I flung the towel over my neck, shut down my computer, and went downstairs.
* * *
As I approached the jacuzzi, I marveled again at how Dad changed our former ‘playground’ with a sandbox and a swing into a real cozy chilling spot. The six-person jacuzzi was placed in the corner. Next to the path leading to the jacuzzi was a small canopy where you could drop stuff like towels, drinks, and other things you’d take to relax. A small shed was placed next to it that could be used to change. It had a few shelves for chlorine and other cleaning materials.
I lifted the cover and moved it toward the designated spot at the side so it was out of the way. It sat between the jacuzzi and the privacy fence. I checked the chlorine and water level, as that one word kept resonating in my head… ‘privacy’…
I stood straight, looked around, and was amazed that I didn’t realize this earlier. Our garden was completely private. Absolutely no one could see me here except the people inside our house. Up until now, I’ve only been home alone for about an hour tops. But now… I had a few hours of alone time.
That little spark started growing inside my head, and I felt a small smile appear on my lips, and my dick chubbed up a little. As I walked over to the canopy and sat on the bench, I weighed the pros and cons in my head, but it didn’t take long to make up my mind. I looked around once more, stood up, and quickly dropped my trunks.
As I stood there with my bare back toward the house, a soft gush of wind caressed my dick and balls. Then and there, I knew I had found myself a new hobby. Still feeling shy, I glanced around, despite knowing I was alone for at least another five hours.
So I started walking around in the garden to get used to the feeling of being naked outdoors. After a few steps, I deliberately started wiggling with my dick, making me giggle like a little girl. The feeling of walking around naked was astonishing! It was clear that my parents would disapprove, and the possibility of being caught, no matter how slim, was so exciting that I felt myself grow hard.
As I looked at my reflection in the window of our house, seeing myself standing there, erect, and with the bushes and trees in the background, it got me all worked up again, despite having an orgasm less than half an hour ago.
Smiling at my reflection, I felt free and started running around our backyard. Feeling my boner wobble from left to right as I did this enhanced my feelings of freedom and liberty. I was completely alone, naked, and stiff. And it felt incredible!
After a few minutes of running and jumping around, resisting the urge to start tugging at my hard dick, I stepped into the jacuzzi to relax. But right before I got in, I realized I might as well grab something to drink. Dad wouldn’t allow it when he was home, but I was feeling bold right now and had a bit of a ‘screw you all’ vibe over me by now. So I walked into the house, which gave me a whole new feeling of freedom as I did this in the buff. But I got used to being naked, so I quickly grabbed a couple of Cokes, headed back, and let myself sink into the jacuzzi.
The warm water around my body and the absence of my trunks relaxed me immediately. I grabbed the remote, and when I pressed the ‘on’ button, the sixty-five-inch TV started sliding up from its hiding place. As the TV began to appear, I pressed the button on the edge of the jacuzzi, and with a soft hum, the pump came to life, and bubbles surrounded me moments later.
I flipped through our catalog of movies and series, and after scanning almost everything, I eventually decided on starting Game of Thrones. I never watched it because my parents didn’t think it was fit for a thirteen-year-old boy. But I knew my dad had lifted all restrictions and that he’d stopped scanning what my sister and I were watching. So, hey! Why not, right? I heard there were naked women in it, so it would definitely be interesting.
I polished off my first can of coke and pressed play. The HBO logo was showing on TV, and the bubbles stopped right at that moment. The self-timer had kicked in, which meant the pump would stop automatically after fifteen minutes. Apparently, Dad hadn’t figured out how to extend it, but I didn’t care too much. Because when I pressed the button, the bubbles came back, along with the noise. The only thing left was cranking up the TV’s volume, so I could hear what they were saying.
Starting to relax, I slid down a little and started to get into the story. I still wasn’t getting what all the fuss was about, but I had to admit that the story was gripping me so far. After a few more minutes, I almost jumped out of the jacuzzi when I heard, “Mind if I join you?” And my sister dropped her bathrobe on the bench next to my towel.
My hands instinctively moved over my dick and balls to cover it up. But as she started to step into the pool, I was stunned by how she looked and almost forgot that I was naked and about to be busted.
My sister was a little over a year older than me, and it showed. Literally. Hailey had filled out in all the right places, something I started noticing a few months ago. She was a popular cheerleader, but she was always nice to everybody, myself included. She was just slightly taller than me, and her hair was a little lighter than mine.
My eyes roamed over her body, and as my dick started to grow, I felt a little guilty for getting hard over my sister. She was wearing a bright yellow bikini, showing off her tight, fit body. Her hard nipples, topping off her c-cup boobs, were showing clearly in her bikini top. Her bottoms were high over her hips but low in the middle. It surprised me that I didn’t see any hairs down there. That’s how low it was at the front.
This all happened in a few moments, and as I stammered a soft, “I’m… I’m uhm… it’s…” my voice cracked.
Hailey clearly didn’t catch on and didn’t know about the situation I was currently in, so she kept going and sat down next to me, her bare shoulder touching mine.
“There. Now we’ve both got the best seats in the house. What are you watching?” she asked, utterly oblivious to the stress I was feeling.
All I could think about was that if her hip touched mine, she’d know I was naked. And if the light was just right, she could see my pubes through the bubbles. If anything happened, I would be busted.
“Its… uhm… Game of Thrones,” I managed to say without a cracking voice.
“Cool! I dropped in on the third season. Never saw the first two. Do you mind if we watch it together?”
“N… no. Of course not,” I said, regaining my cool a little.
“You know there’s naked people in it, right?” she chuckled and poked me in the ribs with her elbow, winking at me.
“I’m… uhm…” I stammered.
“Don’t worry, Bro. You know I won’t tell.”
I pressed pause on the remote and looked at my sister. It tooke me some effort to focus on her eyes because her boobs were distracting me. They were wobbling on the water because of the bubbles.
Hailey looked at me questioningly and asked, “What!?”
“I thought your schedule ended at three, and you had practice after that.”
“Yeah… well…” she started, “You were in Mrs. Halsey’s class when ‘it’ happened, right?” Hailey asked with the emphasis on ‘it.’
“Yeah. Didn’t see or hear anything. We just had to leave.”
“It’s that… well… she didn’t make it.”
“Oh,” I said softly. And I didn’t quite know what to say to something like this, so I continued, “she was nice.”
“No, she wasn’t. But she did manage to teach me some chemistry. She was the only teacher who ever did that,” Hailey said with a certain respect in her voice.
“She sat me next to Sally Brighton. I liked that,” I chuckled.
“Bet you did, little bro,” Hailey smiled knowingly.
Hailey looked a little confused but quickly caught on and said, “Oh, right! Well, the teachers needed time to mourn and get together to talk about what happened. So they canceled all classes for the rest of the day, including my practice.”
“I see,” I said, clearly looking bummed out.
“You thought you had the house to yourself all day, didn’t you? Maybe spank the monkey a bit, huh?” she teasingly said and nudged me in the ribs again.
“Stop it!” I giggled.
“I’m sorry! But you did some growing up last year, so don’t tell me this didn’t cross your mind!”
“I’m… I wasn’t… It’s… maybe…” I stammered.
“I’m just yanking your chain. Let’s watch the show, okay?” she laughed.
I pressed play on the remote, and the show started running again. By now, I had spread my arms, and my hands were resting on the edge of the jacuzzi. One arm was partly behind my sister’s back, and if you’d look at us from a distance, you might think I was trying to clumsily hug her, like a first date in a movie theater.
I kept stealing glances at the wobbly boobs next to me, which made it difficult to focus on the story. And after a few moments, Hailey’s nipples got stiff, and they tried to poke through the yellow material of her bikini top. The moment they did this, I felt my dick grow from soft to full mast in just a few heartbeats. It was a good thing the bubbles were still obscuring the view.
“Like what you see?” Hailey suddenly said, pressing her chest a little bit forward.
Shit! She caught me! I was looking at my sister’s boobs, and she saw it. How could I talk myself out of this?
“Its… I uhm… Just didn’t know breasts would float,” I tried. “And it looks kinda funny when the bubbles move them around.”
Hailey smiled at me after a few moments, looked down at her chest, and said, “Yeah. I guess it looks funny, doesn’t it?”
“It does look funny,” I smiled, “and you’ve got nice breasts,” I said, feeling myself blush as this came out of my mouth involuntarily.
Hailey looked at me with a surprised look, and the moment she opened her mouth to say something, the pump shut off, and the bubbles started to disappear.
Her eyes immediately went down to my groin, and because of the way my arms were lying now, I simply couldn’t cover up quickly. But, judging by the way her eyes grew wide and the blush that spread across her face, she saw what was going on.
“Brett! Oh my…” she said as she put her hand in front of her mouth but kept her eyes locked firmly on my hard dick.
I struggled to get my hand into the water while the other frantically pressed the button on the jacuzzi, but the bubbles just wouldn’t start again, and a small, annoying beep was all I got. The moment my hand finally covered my erect dick and part of my balls, the damage was done, and I felt my face grow hot from humiliation.
“I’m sorry! I… I thought… shit!” I stammered as I felt tears well up in my eyes.
Hailey kept her eyes on my crotch and seemed stunned. The humiliation I felt was growing with every passing second. Then, moments later, I felt the first tear roll down my cheek.
Hailey tore her eyes away, looked at me, and whispered, “Shit, Brett! I didn’t mean to… you… oh, fuck!”
The tears were flowing freely by now, and I saw the empathy on my big sister’s face through my tears. A second later, I felt her hand on my shoulder and a soft, “I’m so sorry. Just should’ve waited for your answer before I got in. I only assumed it was… and that you…”
It was evident she was genuinely upset by the situation. She didn’t appear to be mad or anything about the fact that I was naked. It was more like she just assumed it was okay to barge in on me like she did.
“Its just… You… I…” I stammered between sniffs.
“It wasn’t cool to invade your personal space like this. It just never occurred to me that my little brother was growing up this fast,” she said, primarily to herself.
“It’s…” I sniffed, “it’s okay…”
“No, it’s not!” Hailey sternly said, “I should’ve waited for an answer.”
“And then what? If I said no, you would’ve asked why not,” I said, getting my nerves a little more under control but still feeling stupid, “I just never should’ve done this.”
We were quiet for a few moments, with me still sniffing occasionally, when Hailey suddenly started moving and put her hands behind her back. It didn’t take a genius to see what she was doing.
“Wha… what are you doing?” I asked, feeling both panicked and anxious at the same time.
“I’m making it less awkward for you,” she simply said without looking at me.
Moments later, her bright yellow bikini top came off, and as she threw it toward the bench where the towels were, I took a good look at her magnificent naked boobs. My softening dick was instantly hard again, but I didn’t really care at that moment. They were boobs, they were naked, and they looked like nothing I’d ever seen before! Seeing these in real life was way better than on some corny porn video. These were au naturel, and it showed!
But Hailey didn’t stop there. After she tossed her top aside, she looked at me, smiled shyly, wiggled out of her bottoms, and matter-of-factly dropped these on top of her top. After she was done with this, she said, “There. Now it’s awkward for the both of us.”
“Wha… uhm… yeah… I guess,” I said after tearing my eyes away from her breasts and looking her in the eyes.
There was a twinkle in her eyes, and she glanced down at my crotch again. My hands apparently left my dick and weren’t hiding it anymore because she seductively asked, “Like what you see, little brother?”
I could only nod sheepishly but couldn’t help myself and looked in the water to see what that mysterious place between her legs looked like. My hands were entirely forgotten by now, and I hardly realized that I was completely exposed. Her heavenly body was just too distracting.
“Hey! Bro! Up here!” Hailey chuckled.
“Huh? Oh… sorry. I just…” I stammered.
“It’s okay. I’m just teasing you. You can look if you want. I don’t mind.”
“You don’t? You mean. I can? I…”
“Chill,” she smiled. I noticed a slight blush had spread over her face, and she softly added, “you can watch. If you don’t mind me looking at you…” and her face got even redder.
“At me!?” I croaked, not believing my ears. “Why would you want to look at me?”
“Well… like I said, you did some growing up lately, and you… I don’t know. You look good, I guess,” and her eyes went back down to my crotch.
At that moment, It hit me that I was completely exposed. I instinctively wanted to cover myself up, but then my mind told me there was no need. A short mental struggle occurred between covering up and seeing a sexy naked girl next to me. The naked girl, despite her being my sister, won unanimously.
I glanced down in my lap, and everything was clear to see. My five-inch hardon stood proudly in my lap, and my small bush of black, wet pubes was stuck to my body.
“You really think so?” I asked softly, still not believing she said this and checking if I heard this correctly.
“Oh yeah! Your chest and arms look perfect. And your… is very nice! It looks big on you, and your… uhm… balls too. You look hot!” Hailey said with a lot more confidence now.
“Thanks! You’ve got a nice tight belly,” I started, feeling the need to say something about her, “and your boobs look amazing!”
We were quiet for a few moments, letting our eyes roam all over each other’s bodies, when Hailey asked, “Wanna touch them?”
That shocked me. I could never say no if she meant what I think she meant! But did she mean that? So I just asked, “Touch your breasts?”
Hailey just smiled broadly and said, “Yeah. You never saw tits before, so you might as well get the full package now!”
I was so mesmerized by these intriguing globes on my sister’s chest that my hands started moving on their own. The moment my fingers touched her skin, a shot of electricity shot through me. My fingers began caressing both her boobs, and before long, I was kneading them a little and savoring the way they felt.
“You like it?” my sister asked as she looked at my face.
“Oh yeah!” I exclaimed, realizing I was probably way too enthusiastic about it.
But Hailey didn’t seem to mind. She just smiled and pushed her chest forward to give me better access.
“Then play with my nipples too,” she softly said, adding an even softer, “please.”
I tore my eyes away from her boobs again to check out what she meant. She had a soft blush below her eyes and looked… flushed. But immediately after I noticed this, it dawned on me that she was just plain horny! And, as a matter of fact, so was I.
So I didn’t need any more convincing to start playing with her nipples. I took her right nipple between my thumb and index finger, admired the texture and hardness, and gently squeezed it. Immediately after I did this, a soft moan escaped Hailey’s lips.
My eyes sought hers, but even though she didn’t look at me, it was immediately apparent that I hadn’t hurt her. Her mouth was slightly open, and her eyes were again fixated on my rock-hard cock.
“This feels good,” she said, smiling timidly.
“Yeah…” I responded.
“Can I… do you mind if…” Hailey asked as she kept looking at my dick.
“I… uhh…” I responded, entirely focused on massaging my sister’s tits and not being able to answer appropriately.
Thankfully, she didn’t wait for an answer. The moment her fingers wrapped themselves around my shaft and an overwhelming feeling washed over me, I almost jumped out of the pool.
“Ooohhh!” I heard myself moan as someone else touched my dick for the very first time.
Hailey just smiled and asked, “You like that, huh?”
I could only nod as her hand moved over my shaft, rubbed my dickhead, and toyed with my balls.
“You’re bigger than Josh,” Hailey said as she fondled me.
Josh was her boyfriend, who she broke up with a few weeks ago. I didn’t know she did any stuff with him. Hailey was my sister, and sisters aren’t supposed to do this. That’s how it worked in my head until that moment.
“You did… aaahhh… this before?” I managed to say.
“Yeah. I jacked and sucked him, and he ate me out. Badly, I might add. But we didn’t fuck. He wanted to, but it just didn’t feel right to me, so we didn’t. He broke up with me because of that,” she said but never stopped fondling me.
“Wow. Didn’t know… hhhmmmm… that.”
“Did you ever get any from Melissa?” Haile asked seductively, basically jacking me off by now.
“Ohhh… no. We… we just kissed. She didn’t even… oohhh… let me feel her boobs.”
“Stand up,” Hailey said and tugged at my dick as if she wanted to pull me out of the water and prove her point.
I didn’t want to let go of my sister’s tits, but she didn’t leave me a lot of options. I looked at her and had to ask. “Why? What’s wrong?”
“Nothing. I wanna suck your cock. My little brother only kissed a girl. That needs to change.”
“Suck my… but… we’re…” I stammered but couldn’t wait for it to happen.
“And? You’ve got a nice big one, and I wanna suck it. So what if we’re brother and sister? I don’t mind. Do you?”
“Its that… no. No, of course not! You’re hot, and I wanna… you know.”
“Then get up and stand in front of me. I wanna know how your cock tastes,“ she chuckled.
I clumsily got to my feet and almost tripped. The anticipation of getting my first ever blowjob didn’t look good on me. The moment I stood up straight with my back toward Hailey, her hand cupped one of my butt cheeks, and she said, “Tight ass, Derp!”
I usually didn’t like it when she used that nickname on me, but now she could call me everything. As I carefully turned around and my dick came close to her face, her eyes were focused on my throbbing boner. All the while, her hand kept gripping my ass.
“Wow! You’ve really got a nice one, Bro!”
In the beginning I was afraid that I would’ve felt awkward showing myself like this, but her genuine admiration and enthusiasm put me at ease and even boosted my confidence.
I didn’t have a lot of time to think it through because moments later, I felt something warm and moist on my dickhead. I looked down, and my sister had wrapped her lips over my glans and looked up at me with an extremely horny look in her eyes. Of course, it was still just the tip, but if this already felt this good, I couldn’t wait for the rest to enter her mouth.
“Oh! I….aahhhh…” I involuntarily responded.
Hailey opened her mouth and started lapping her tongue over my shaft and dickhead, her eyes never leaving mine. I had a difficult time focusing, and she probably noticed. Because after a few moments, her eyes went down to my shaft, she pulled her head back, opened her mouth, and started sliding it down over my almost painfully hard cock.
The feeling around my cock was beyond everything I dreamed about in my wildest dreams. The warm, moist feelings, her tongue manipulating the underside of my cockhead, her free hand toying with my balls, everything! All of this would’ve brought me off separately, but all these things combined amplified it in a way that I knew I wouldn’t last long.
“Oh… you… I’m… aaaahhhh!!!” I moaned loudly.
Hailey responded with an exciting moan herself, which resonated on my dick and balls, and brought me even closer. I don’t know how long she was going at it by now, but as my balls started pulling up toward my body, I knew I wouldn’t last much longer. My whole body decided that I shouldn’t move a muscle because that feeling of absolute bliss might end then, but now that I was getting near the end, my hips started moving out of their own.
“Oohh… look… aaahh… out… I’m… oooohhh!”
I didn’t know what to expect. In all the porn I’ve seen so far, the women and girls either swallowed it all or got a facial with some of it dripping on their tits. Hailey couldn’t miss that I was about to cum, and was too far gone to warn her.
“Cum on my tits, little bro!” Hailey said after pulling her mouth off my dick and jerking me.
I looked down at my sister’s hand around my dick. She was pushing her chest forward and opening her mouth while looking intensely at my dick.
That did it. With a loud groan, I came. I felt spurt after spurt leave my dick, and even though I had trouble keeping my eyes open and my vision was a bit blurry, I kept my eyes locked on what was happening down there. The first spurt landed on my sister’s nose and immediately started dribbling down. The next hit her on her tongue, and the third and fourth were around her mouth.
As the power of my spurts decreased, they started landing on top of her firm tits. I loved seeing videos where a woman was coated in cum, but seeing my own jizz covering my sister, was way hotter than any video could ever be. Realizing I felt my knees buckle as my orgasm started to die down, I needed to do something. So, I steadied myself by grabbing onto Hailey’s shoulders and prevented myself from falling.
Hearing myself pant, and as the strength in my legs returned, I stood up straight and looked down at the mess on my sister’s face and body. I felt a bit worried that she was mad at me for not warning her. But as she saw me looking, she smiled and started licking her lips, exaggerated and seductive, which caused me to moan again.
“You like this, don’t you?” Hailey said softly as she started smearing my cum all over her tits.
I wasn’t trusting my voice at the moment, so I nodded furiously and kept my eyes fixed on her boob-massaging hands.
“I’ve seen your browser history…” Hailey continued, “and as I felt you were about to shoot, I wanted to reward you. You don’t mind, do you?”
“N… no. I… oh wow,” was all that came out of my throat.
“Good!” Hailey said, moved her head forward, and licked the drop that hung down my dickhead.
I was sensitive down there now, but this wasn’t at all unpleasant. A few moments later, Hailey sunk further down into the water and started to wash my cum from her body. This was my cue to sit back down, and as I did this, I saw small clouds of my cum floating by but quickly disappearing into the filter.
After Hailey sat back up, she looked at me and smiled again. Then, she moved her head toward me and kissed me hungrily on my lips. Moments later, her tongue started probing around, and before I knew it, we were making out hardcore.
“You’re quite a kisser, Derp!” Hailey smiled as we both needed to breathe.
“Thanks! You’re not too bad yourself,” I smiled, feeling more confident by the minute.
“But now it’s my turn!” she announced, pulled herself out of the water, and sat on the edge of the jacuzzi with her back against the fence. She obscenely spread her legs, giving me my first ever close-up view of a live pussy. It looked… interesting. I had my anatomy lessons in school, so I knew the mechanics and could figure out what I was looking at. But seeing her bald pussy, and realizing I was about to touch it, was a whole different ballgame.
“Wha- what do you want me to do?” I croaked.
“Eat me out. The way you work your tongue in my mouth works even better on my pussy,” Hailey said, spreading her pussylips with her fingers, making it even clearer to me where everything was.
I shrugged mentally, moved forward, and looked closely at everything. I smelled a light musky odor that triggered something inside me. My dick hadn’t gone down much, but this smell caused me to fully bone up again. I saw where my sister’s clitoris was. I felt a bit of a primal urge to return the favor, so I stuck out my tongue.
The moment the tip of my tongue hit her clit, her hands left her pussylips, and she dug her fingers in my hair. The texture I felt on my tongue was different from what I had ever felt before, but I knew then and there that I loved it.
As I applied a little more pressure, Hailey started moaning above me. Of course, I’ve seen clips about a woman being eaten out, and I started revisiting them in my head. First, I made small circles with my relaxed tongue. Then I repeated this with my tongue pulled into a small tip. Next, I lapped directly over her clit, and alternated my actions by licking everything around it.
All the while, Hailey’s moans kept increasing, and her hips started gyrating. I wanted to stick a finger inside her because I remembered some excellent results in these vids. But I wasn’t too sure how Hailey would handle this. So I moved my fingers up there and started rubbing around as an extra set of tools to please her.
“Aaahhh! Yesss!” she moaned the moment my fingers touched her.
Okay… maybe she won’t mind? I slowly eased my index finger toward her opening and rubbed around a little. This made her squirm even more, and she started opening her legs even further. I was getting hornier by the minute from her scents and the encouraging moans, so I decided to go for broke.
My index finger was right at the entrance of her pussy. The moment I started applying some pressure, a sudden gush of my sister’s juices filled my mouth, and another loud moan came from deep within her throat.
A loud, “Ooohhh…yesss!!” came through her clenched teeth above me.
I started inching my finger into my sister’s pussy, all the while focusing on licking her clit. I marveled about how she felt inside, and her pussy clenched my fingers every now and then. After my finger couldn’t go in any further, I started pulling back slowly. But urged on by Hailey’s moans and gyrating hips, I sped up my finger’s movement. Before I knew it, I was fingerfucking my sister at a serious pace while trying to keep my tongue on and around her clitoris.
“Yess… yesss… yesss… oh yesss!!” Hailey kept moaning.
Her pussy started gripping my finger more urgently and frequently now, which made me realize she was getting close.
“Ooohhh… ooohhh… ooohhh… Brett… I’m. Ooohhh…”
Most women I saw in the porn videos started screaming loudly when they were about to cum. But Hailey just sort of started panting heavily, and deep, low grunts came from her throat. But her entire body and all her movements made it clear that she was about to have her climax. And somehow, this was way sexier than those exaggeratedly screaming women.
My tongue kept lapping all around my sister’s pussy, and my finger was rapidly moving in and out of her. Then, inside her pussy, I noticed a small spot that felt a tiny bit different from the rest of her pussy, and I focused on rubbing that spot as I went in and out.
I apparently did something right because, above me, Hailey softly moaned, “aahhh, yes! Aaahh, yes! Aaahhh, yes! Oohhh, Brett!”
Suddenly, her legs clamped shut, and I could only hear everything very muffled. But I didn’t need to hear clearly what was going on. My sister’s body shook, and her pussy was contracting around my probing finger. The amount of juices that coated her pussy doubled in quantity, and I kept lapping around to swallow it all.
I knew I shouldn’t keep up the high-energy probing and lapping, so I slowed it down after her orgasm did. But I didn’t stop it entirely and slowly and teasingly kept going. Her legs loosened their grip around my head, but moments later, they shut firmly again, and another orgasm washed over her. Judging by her moans and the juices that were less than her previous orgasm, this one wasn’t as intense.
This one also didn’t last as long as her first one, and as she relaxed her legs again, I wondered if I could make her cum a third time. I knew I liked to cum, so I figured this wasn’t any different for a girl. I knew girls could cum more often than boys, and I enjoyed making my sister feel good, so I kept trying.
And a few minutes of slow probing and lapping later, the whole sequence of shutting legs, shaking body, and copious amounts of cunt juices started again.
Feeling powerful by now, I wanted to see if a fourth was possible. But right after she came for the third time and realized I kept going, she chuckled, “Stop it! Aahhh…. You made your point. You know how to use your tongue.”
I looked up at Hailey, sitting on the edge of our jacuzzi with her legs obscenely spread, and smiled. She smiled back lazily at me and spread her arms invitingly. Then, with the back of my hand, I wiped my sister’s juices from my chin and got to my feet. I looked her in the eyes, and before I got the chance to react, she wrapped her arms around me and pulled me into a tight hug.
Standing here on the slight slope of the jacuzzi’s seat was a little tricky, but I quickly found a stable footing. I placed my hand on her left tit, tweaking her nipples, and the other snaked around her back, grabbing her around her shoulder for extra support.
Hailey looked deep into my eyes and kissed me hungrily on my lips. Moments later, her tongue sneaked into my mouth, and we were Frenching like there was no tomorrow. After a few minutes of this, where I kept pinching her nipples, she broke the kiss and hugged me again as she lay her head on my shoulder.
She asked, “Where did you learn to do that? No one ever made me cum this long and hard!” and the amazement in her voice was unmistakable.
“I… uhm… this was my first time. I’ve only seen videos of this,” I said, hugging her with two arms and loving the sensation of her hard nipples against my chest.
Hailey lifted her head and looked at me, still pressing her tits against my chest. I noticed something had changed in the way she looked at me. She looked… focused and determined.
“Really?” she whispered, and I felt her legs wrap around my ass, bringing my stiff cock into contact with her warm pussy.
“Wh… what?” I stammered, acutely aware of how close I was to penetrating my sister.
As we started this, I figured we’d just do the more simple stuff. A brother and sister can’t fuck. Can they?
“Ssshh…” Hailey soothingly whispered.
I wasn’t going to chicken out on my first fuck. But she was my sister! That’s when my hormones started clouding my brain. Hailey reached between our bodies and grabbed my dick. She still whispered, “If you’re this good at eating me out by just watching a few videos, I wanna know how good you are at fucking me!”
Her eyes looked deep into mine, and as she lined me up, I could hear myself swallow. Hailey must’ve sensed I was nervous because she stroked my cheek with one hand as her other ensured I was lined up properly.
“Just push, and you’re in,” she whispered in my ear, followed by a deep and exciting, “Fuck me, little bro!”
Her legs gently pushed against my ass, and all the mental resistance I felt was out of the window as I looked into the horny eyes of my big sister and heard her urging me on.
So I slowly pushed and felt my dickhead slip into the most wonderful place I could ever imagine.
“Ooohhh! I feel it!” Hailey moaned, and as she tried to keep looking, I saw her gaze was unfocused.
I wanted to push in hard and feel all of her warm pussy grip my dick, but I didn’t want to hurt my sister. So I slowly kept pushing, feeling only minor resistance. But as I inched forward, Hailey’s pussy gripped me firmly every now and then.
“Aahhh…” I heard myself moan and looked down at where our bodies were merging.
Hailey’s legs started pushing more firmly against my butt as if to encourage me. I knew I didn’t need encouragement at all, but it felt exciting nevertheless. But when I looked into my sister’s eyes again, all I could see was lust and a pleading look.
“You’re… it’s… dick… ooohhhh… deeper!” Hailey moaned incomprehensibly.
I started getting at the end of what I had to offer in terms of length. I knew I wasn’t small, but I wondered if I was big enough. My sister’s ragged, shallow breaths were a good indication to me that she enjoyed what I was doing. But when I could go no further, and my public bone pressed against hers, she dug her nails into my back with such force that it actually hurt a little.
“Oohh… oohhh… oooohhhh!!!. I’m… aaaahhh!” Hailey moaned, and I could feel by the contractions of her pussy that she came again.
But her entire body language screamed that she was having an intense orgasm. Her eyes were crossed, her breath was shallow, she squeezed me tight against her body, and low grunts came from within her throat.
I didn’t know what to do, so I decided to wait for her orgasm to die down a bit and let her enjoy it. So I held still and kept studying her reactions to her orgasm. A few moments later, as her pussy was still contracting, her eyes tried to find mine. Finally, after a few attempts, they did, and she groaned, “Fuck me! Your cock is… ooohhh… just fuck me!”
This turned me on immensely! I had never heard her talk or seen her act this way. I was giving her his pleasure. Me and my hard cock were driving my sister nuts. In a good way, but still. I felt all proud, warm, and fuzzy inside realizing this.
But I wanted… no, I NEEDED to fuck for real now. My cock was inside a cunt for the first time, and I didn’t care at all anymore that it was my sister’s. So I started sliding back, and that fantastic feeling surrounding my dick returned. But, of course, I’ve seen enough porn to know not to slide out too far. But I kept it on the safe side and pushed back the moment I was a little over halfway.
“Oohhh… your cock is SO amazing!” Hailey groaned as she kept thrash talking and turning me on that way.
As my pubic bone hit hers again, she didn’t cum, but threw her head back between her shoulder blades. I pulled out and back in again, causing her head to wiggle.
Okay… she wanted me to push in harder, so I pushed a little firmer this time.
This was it. Her trash talking, her velvety pussy around my dick, and her urging me on to fuck her hard made something snap inside. I guess my instinct took over because I started slamming hard into my sister. I also started pulling back further, keeping just the tip inside.
During my first ever fuck, I only slipped out once. And that was remarkable. At least, that’s what Hailey’s friends told her, she informed me later.
Each time I slammed into her hot pussy, a deep, “Ah, yes!” came from my sister’s throat. By now, she was looking at me again with one hand around my neck and trying to keep herself steady with the other.
We fucked like this for what seemed like hours, but it was probably a little over two minutes. I felt I was rapidly approaching the point of no return. I didn’t know what to do when I came, so I groaned between my panting, “I’m… ahhh… I’m cummi… ohh… What…”
Hailey just kept on groaning, “Ah, yes!” every time I slammed into her, but I needed a response. And I needed it fast.
“Aaahhh… Hailey! Oohhh…”
That seemed to snap her out of it a little because her eyes tried focusing on mine.
“You’re amazing!” she groaned.
“I’m… I’m… almost… what should… aaaahhh… I…”
“Oohhhh… this is so… ooohhh… good!! Shoot inside me! Aahhh… just don’t… stop! Fuck me! Ooohhh…”
As she kept saying how good I made her feel, I felt another boost of pride shoot through me. And I knew this was it. I was going to cum, and I would shoot my jizz inside my sister. This was so mind-blowing that it extended my cum a little longer.
I slammed harder and harder into my sister’s flaming hot and soaking wet pussy. I needed to cum! Now! The pressure kept rising, and the moment I passed the top of the hill, and the free fall of my orgasm was about to come, Hailey lost it.
But she lost it so much that her body shook almost uncontrollably, and her pussy clamped so hard around my dick that it prolonged my orgasm even more. Her hand gripped my shoulder firmly, and her nails dug into my flesh, which felt both painful and hot as fuck.
Because of her clenching pussy, I managed four more slams into my sister. At the moment, caring for the way she was experiencing her orgasm was long gone. It was me that needed to coat my sister’s insides with my incestuous sperm.
As I was about to slam into her for the final time, I felt my balls pull up, even before my hips moved forward. This was it. Hailey was still riding the high of her orgasm, and I didn’t know if she was with me enough to realize what was about to happen.
With that last, deep and hard push, I felt the tip of my dick touch something inside her. And right after I felt it touch my cock, the first spurt left my balls. I was experiencing every millisecond in slow-motion, and despite having to shut my eyes, I just experienced everything that was happening around me.
A loud “Aaahhhhh!” came from within my throat, and immediately after that, my cock jumped a second time, releasing the second spurt of my universe-scattering orgasm.
Hailey’s pussy contracted sharply again, and that, combined with her high-pitched grunt, fell in sync with my third spurt.
By now, I had buried my face in that soft spot between her neck and shoulder, and the power of my spurts died down. Spurts four and five were still going and, judging by Hailey’s reaction, powerful enough to keep her riding her orgasm, but I knew this was the end. I was no longer a virgin.
And the fact that I had just lost my virginity to my big sister didn’t bother me at all. I expected some guilt or remorse. Maybe even some disgust. But it was none of that. On the contrary, I loved every second of it and would do it again in a heartbeat.
This all shot through me as I tried to regain my breath. Hailey’s cunt wasn’t trying to squeeze my dick off any longer, and I could sense she was coming back down.
Hailey was panting heavily as she gently pulled my head back by my hair and started Frenching me. It wasn’t a hungry and rough kiss like earlier, but a more loving and thankful one. I liked this better at this moment.
My dick was still deep inside my sister and still almost completely hard when we broke our kiss. Our foreheads touched, and we looked into each other’s eyes. I could see a smile forming on her face, and she whispered, “That was an awesome fuck, little brother. You sure know how to please a girl.”
It was as if it took me a while to digest this. It was apparent she loved it. This wasn’t a lie or a way for her to boost my ego. She genuinely meant it. So I needed to reply to that, but it was hard to find the words.
“I… this was… this was my first time.”
“I know,” she whispered, “Guess you’re a natural then, don’t you think?” she smiled.
“Dunno. Maybe we’re just made for each other.”
“Guess we’ll have to find out then,” she said coyly as her fingers started tracing down a path over my spine, leaving me with goosebumps all over my body.
After this first fuck, we did it again as often as we could. Being alone most of the daytime helped a lot. We developed a rhythm where we’d hop into the jacuzzi after school. And since our bedrooms were in a separate part of our house from our parent’s, we started spending the night together and fucked like rabbits every night. I never was more sexually satisfied in my life than in those early years.
But all good things come to an end. Almost a year after we started our sexual relationship, we were busted. And busted big time. Mom had been suspicious for a few days, so she sneaked toward our rooms. And when she heard us moan… she suddenly walked into Hailey’s room. Right at the moment that I blasted my cum inside her sopping pussy.
Needless to say, the shit really hit the fan big time. We lost all our privileges, and I had to move to the other part of our house. So mom and dad took Hailey’s room, she took mine, and I moved into the former master bedroom.
It took us all a few weeks to get used to the situation. Gradually, the conversations started again, and slowly things returned to normal. Both Hailey and I eventually found ourselves some nice partners. I liked hers, and she liked mine. But when she insisted on sleeping in my apartment the night before her wedding, I just had to find an excuse for my girlfriend to leave the house, which she thankfully did.
That night, Hailey and I finally fucked again after more than six years. And it was almost as epic as our first time. But we both knew, deep down, that this was also our last time.
But the memories of losing my virginity to my sister in our backyard jacuzzi will light up my life for as long as I live. That’s for sure!
hoc est maxime placeat scribere
Copyright 2022 – Jason Crow
All rights reserved
You’re welcome 🙂 Two, even though they’re both short (-ish), stories in a short time. I guess I was inspired, because the words just poured out of me. This one won’t be on Nifty, because it’s b/g and for plain straight stories, there’s no place on that wonderful story site.
Anyway… I hope you enjoyed it! As usual: all comments, good or bad, are always welcome. You know the drill by now 🙂
Randall did another awesome job with the illustrations! Thank you SO much, Randall! You can send your praises to: firstname.lastname@example.org.
Also another BIG thank you to Randall and E-o-F for the proofreading! Thanks, guys!