So, I was fourteen years old and horny as fuck. So far, so not very surprising. Of course, when I discovered the delights to be had playing with an erection, I thought to begin with that I was the only one. Then, conversations that I’d been overhearing at school for a while suddenly made sense, and I realized that all boys were at it like knives.

At that point - well to be honest nothing has really changed too much since then - pretty much all females would turn me on, including my mom, which did make me feel a little weird, and my sister. But a boner is a boner!

My sister Emily was the stuff of dreams: not the classic blonde, slender cheerleader type, which admittedly did also feature often in my masturbatory fantasies. No, she was dark, with huge, deep black eyes that you could happily drown in. Her body was curvaceous with a full but firm butt and breasts that even her sports bras couldn’t fully contain, and that moved in a mesmerizing way as she walked. Excuse me for five minutes...

That’s better! Right, where was I? Ah yes, Emily’s breasts - the other wonderful thing about her sports bras was that they did almost nothing to hide her nipples which were almost always long and hard and made my mouth water. OK, before I have to take another break, let’s get to how things changed from a normal pervy teenager jerking off to visions of his sister to something more interesting.

It was a pretty average Monday morning, everyone rushing around the house, trying to get their slot in the bathroom, get dressed, get fed, and get their shit together.

In the midst of all that I couldn’t find the blue shorts that I wanted to wear. Having rifled my drawers I went along the corridor to the top of the stairs.

“Mom, where are my blue shorts!” I shouted down.

“Aren’t they in your drawer?!”

“No!”

“Are you sure you put them in the wash?!”

“Yes!” I shouted back, but now that she’d asked I wasn’t actually one hundred percent sure.

“Dunno then! You’ll have to wear something else.” Mom replied, coming to the bottom of the stairs and looking up at me. From where I was I had a lovely view down the front of her blouse. The tops of her D-cups (I’d checked a bra in the wash long ago!) and the cleavage between looked soft and brown and gorgeous. I could feel my tighty-whities stretch as my dick did its thing.

“Are you sure you don’t know where they are?” I asked, playing for time because I’d now remembered throwing the shorts down the far side of my bed when I was in a hurry to get at an erection caused by, I believe, our neighbor, Betty, bending over while weeding her flower beds. Very nice ass has Betty!

“I’m sorry,” Mom replied, throwing her arms wide with her palms facing upwards, which incidentally thrust her chest out and made my growing stiffy grow even faster. Luckily I was behind the half wall around the stairwell otherwise she’d have seen it for sure!

I pouted to myself as she walked away and turned to go back to my room. That was when I saw Emily standing in her doorway, clearly looking at me. As I’d turned I could have sworn that her hand was moving upwards in a weird sort of motion that ended up with her playing with her hair. Now, I admit that I had (have?) a one-track mind, but it looked to me as if I’d very nearly caught her in the act of touching herself!

At that point in my life, I don’t think it had even occurred to me that girls had the same urges and desires that boys had. They were sugar and spice and ... whatever, not like dirty boys. And this was my big sister, virtually all growed-up at sixteen and a half ... surely she wouldn’t ... really?

I still had a bit of an erection but I had no choice other than to bluff it out. I could feel it bobbing about as I walked towards her, and as I did, her eyes were never still. They’d flick down to my groin and then back up, only to drop again. It was a pattern I knew well: being desperate to look at something that you knew you shouldn’t be looking at. Emily was definitely very, very interested in what I had in my briefs!

As got closer I saw that her face was bright red and her amazing nipples were standing out proud and lovely. Now, at this stage, my sister would normally have called me a perv and stalked off, but not today.

“No blue shorts, huh?” she asked, smiling. Having just been guilty of it myself, I recognized a stalling-for-time line when I heard one. And, sure enough, she glanced downward again.

I found the idea that she wanted to look at my erect penis very, very exciting and her eyes snapped back up as it twitched and swelled a bit more.

“No,” I replied, more than happy to play along. She licked and nibbled on her lower lip and her eyes flicked up and down some more. “I’ll have to wear the black ones, I suppose.”

“What about the grey ones? They’re--. Never mind, I’ve gotta go.” I smiled to myself as she disappeared into her room and I carried on to mine. I’d stopped wearing the grey shorts because they’d become too tight! Apparently, this wasn’t the first time that Emily had shown an interest in what I had inside my shorts!

Later, when I wasn’t distracted by a hard-on, I was honest enough with myself to admit that it was just possible that I may have misread the signs.

I felt guilty as hell, sitting there with her diary in my hands, but I needed to be sure! It had a combination lock on it but I was confident that I could hack that. A little pressure in the right direction and you can feel the wheels get stiffer when you go over the right numbers.

My only concession to being goodish was to go straight to the entry for two days ago.

‘Adam looked so cute, standing in his tighty-whities talking to Mom. I was already a bit moist looking at his little butt when he started to get hard!!! Had to give my clit a little rub, and he nearly caught me! So much for promising myself that I’d stop letching after his little bod! Couldn’t keep my eyes off it as he walked up to me. Not a bad size for 14! I must, must, must stop doing this, but I want to see it in the flesh so badly!!’

I stopped reading at that point, locked the diary again, and went to my room to beat off.

Immediate needs taken care of, I had a proper think about how to help Emily, and myself, of course, to fulfill her wish. It had to be something deniable and plausibly innocent. The plan I came up with in the end wasn’t entirely without risk but I thought it stood a good chance of working.

The next morning I was ready and waiting. I’d put my earbuds in to give myself an excuse for not hearing my alarm or anyone calling me. But with nothing playing in them so that if it wasn’t Em who came knocking I could abort. Then I’d arranged myself, artfully I thought, naked on the bed with just a corner of the quilt covering my junk.

Now I just had to wait and hope that it was Emily who Mom sent to wake me up. I was half hard just thinking about it, and it grew a little more when I heard Emily’s voice, “Adam, are you awake?” I ignored it and tried to keep my breathing under control as I heard the door open.

At this point I thought that one of two things were most likely: if she wasn’t interested enough she might just try shouting louder, but if she was then she’d get closer. It was a real struggle to keep calm as all I heard were her soft footsteps.

My thinking, admittedly devious, was that she’d have to get quite close to pull back the covers if she wanted to see me, and that would give me the chance to watch her.

Just the feel of the fresh air on my dick was enough to make it rise to full attention and I risked opening one eye a crack. She was staring at my boner with her mouth slightly open and her left hand was rubbing in tiny circles at the top of her pussy! My big sister was playing with herself while looking at me!! I’d never been so excited: my cock was bobbing around and I thought that my heart might burst out of my chest.

I shut my eyes and lay there, praying that she’d touch me, for what seemed like forever. Eventually, I felt the covers being drawn over me.

“Wake up sleepy-head!” she called out, shaking my shoulder.

I grunted and made a big thing of stretching and yawning before apparently appearing shocked to realise I had a woody, and then relieved to see that it was covered.

“What time is it?” I asked blearily.

“Time you were up,” she replied, and then, when I looked confused, she pointed to my earbuds.

“Mom says to get a move on or you’ll miss breakfast.” I grabbed the quilt as if to pull it back and she turned away. But I saw her peek back as she was closing the door.

I hobbled to the shower where I decorated the door with rope after rope of cum as I relived the vision of Emily rubbing her pussy.

I was still wondering what to do with this wonderful revelation when Mom provided the perfect opportunity and asked Emily to babysit me. She didn’t put it quite like that and I kicked up a fuss about not being treated like a baby, but inwardly the idea of an evening alone with my big sis ... well you know by now the effect it had on me!

Normally I spent evenings in my room: playing video games, on the socials, spanking the monkey, and, OK, maybe the occasional bit of school work. That evening though I waited until they’d left and then went straight down to the lounge where Emily was watching TV. I snuggled up next to her and grabbed the remote, flicking through the channels until I found a Dua Lipa music video.

“She’s so hot, don’t you think?” I asked her.

“I suppose,” she replied grudgingly, looking a bit cross at me hijacking the TV. Then I began to squeeze and rub my dick. At first, she tried to ignore me, but then I put my hand down the front of my tracksuit bottoms.

“What are you doing, Adam, you little perv?”

“Come on sis, I know you like looking at it when it’s hard.”

“I do not,” she replied indignantly, but her eyes were watching my hand like a hawk.

“I was awake the other morning, you know. I saw you looking at me ... and touching yourself.”

“I-- I-- I--” she stuttered as I pushed my pants down and stroked my now very erect penis.

“I could stop. If you want?” I teased.

I admit that I was hoping that she’d touch me and bring me off, or even give me a blowjob, but what she actually did was way better: she pushed her hand down the front of her own shorts and started playing with herself!

It was so fucking hot: beating off while she touched her pussy, but I wanted more!

“Can I see?” I begged. “Pleeeaaaasssee?”

She looked at me long and hard. I met her gaze, which was difficult because her hand was still moving over her pussy.

“No one must ever know,” she said finally, and my heart skipped several beats: Jesus fuck, she was going to do it! I crossed my heart with the hand that wasn’t busy, and held my breath as she undid her shorts and pushed them, and her panties, down to her knees and off over her feet.

It was only when she sat back that I saw her pussy and I was instantly in love.

“Emily, it’s beautiful,” I gushed. And it was: lovely plump-looking mounds separated by what looked for all the world like a gorgeous pink flower with petals of the softest, moist-looking flesh and with only the lightest patch of soft, dark fur above. I glanced up at her and she was blushing furiously but also smiling, as if maybe I’d said the right thing.

“You’re a very, very naughty little boy,” she said softly as she watched my hand stroking up and down my erection and her hand crept back down to her pussy.

She mostly just rubbed the bump at the top of her slit but I loved the way it made her eyes flutter and the soft moans she made. We jacked off, or jilled off I suppose, together and I was more excited than I’d ever been!!

When she pushed a finger up inside her pussy it was just too much and I came all over my belly. She groaned, pushing her hips way up off the couch and spreading her legs wide. The flower now had an enticing wet hole that her finger was plunging in and out of. I was besotted with it and got as close as I dared. She was very, very wet and the fragrance made my head swim.

The fingers circling the top were a blur and she added a second finger before squealing loudly a few times and then clamping her legs around her own hands. Her whole body juddered alarmingly but the expression on her face was one of pure joy, and I realized that her orgasm was an awful lot more powerful than mine. And then it happened again while she giggled happily and grinned fit to burst.

When it was finally all over she had a slightly embarrassed smile on her face. I knew I was looking at her with awe: I’d never seen anything so wonderful.

“Em, that was awesome! Is it always like that? And you smell incredible. Can I taste you?” I babbled, completely overwhelmed by what I’d seen.

Suddenly the enormity of what we’d done seemed to crash down on her. “No! Fuck! We shouldn’t even have done this!” she squealed, covering herself with her hands. “Go to your room!” It seemed obvious to me that she was putting on her anger. I wasn’t sure why, but I did what she asked anyway. At that point, I would have done anything she asked, anything at all!

I sat in bed, stroking my hardon. Not jacking off, just remembering what we’d done. I couldn’t get the perfume of her sex out of my nose or out of my mind.

I heard Emily come up to bed not too long after and wondered if she might be going to touch her pussy thinking about me. Then I heard our folks come home, turned out my light, and pretended to be asleep. I didn’t want Emily to get into trouble for not looking after me properly.

There was a brief flash of light from the door, which I figured was Mom looking in on me, and then some drunken giggling from the corridor. I was pretty sure that I knew what was coming next because there was a reason that it was believable that I’d have earbuds in while I slept: Mom and Dad’s room was next door to mine and, when they’d had a few drinks, they weren’t so careful about keeping the noise down.

Sure enough, a few minutes later I heard more giggling and then some moaning. I knew they’d be busy for at least half an hour and neither I nor my boner had forgotten about Emily, tucked up all alone in her bed.

I crept along to her room. The light was off but I snuck in, went over to her bed, and crawled under the covers.

“What are you doing?” she hissed when she realized what I was up to. “They might catch us.”

“Trust me, they’re busy,” I giggled, wriggling around until my face was between her legs. There was that gorgeous scent again and this time I didn’t ask permission.