That Time I Caught My Brother Wanking - Cover

That Time I Caught My Brother Wanking

by alan14

Copyright© 2020 by alan14

Humor Sex Story: Emily arrived home from school and found her brother Jordy wanking, more specifically he was wanking over pictures of her boyfriend Tyler. So there was only one thing to do, a double date, Emily & Tyler, Jordy & Tyler's sister Jess. Let's see what comes out the other side... (note there's an m/m tag, but it's only in the background, I've included it for people who are offended by gay sex)

Caution: This Humor Sex Story contains strong sexual content, including mt/ft   ft/ft   mt/mt   Gay   Lesbian   BiSexual   Anal Sex   First   Oral Sex   Size   .

There’s nobody in when I get home, so I go to the kitchen, make a mug of tea and some toast and take them upstairs to get my homework finished. I’m meeting Tyler tonight and didn’t want to be late, our last date had got seriously hot and heavy, maybe tonight I’ll let him fuck me. Last night he sent me some dick pics, they look good, so much bigger than my last boyfriend, Ryan, he was a nice guy, but he had such a tiny cock, and my god, talk about premature ejaculation, he came before he’d even pulled it out of his pants.

At the top of the stairs I can hear noises from my brother’s room, low groans and grunts, he’s wanking again so I push his door open a crack, now talking about nice cocks, Jordy has a very nice cock, long, thick with some really pronounced veins, a nice head too, such a shame he’s my brother.

I take my tea and toast into my room and open my History textbook, we’re doing the slave trade, horrific stuff, how could people be so cruel? I’m writing notes about the Royal African Company and Edward Colston when my mind wanders away from the depressing homework and back to Jordy’s cock, I just can’t concentrate.

Oh well, I close my book, take a last bite of toast and sip of tea and head across the landing for another look.

The door has swung back shut, I gently push my foot into the gap and move it open a touch, Jordy’s well into it now, he’s lying on his back, his pants around his ankles, his t-shirt pulled up to his neck. I spend a little while looking at his flat stomach and 6-pack, god my brother is sexy.

Jordy’s holding his phone in his left hand, pumping that fat cock in his right, oh my, what a sight, I can’t help myself, I slip a hand inside my shorts, I rub myself over my knickers, my fingers working in time with Jordy’s fist, faster and faster, his grunts getting louder, which nicely cover the little moans I can’t help escaping my lips.

Jordy cums at last, ropes of thick spunk shoot from his big cock and land on his stomach and chest, and that sight was my tipping point, I can’t help myself, my orgasm starts, and there’s no stopping it, I stumble forward with the tremors and end up standing in Jordy’s room, flushed from my orgasm, a hand in my shorts and lady juice sliding down my leg.

“What the fuck?” Jordy cries, casting his phone aside as he tries to cover himself.

His flying iPhone catches my eye as it lands on the bed.

“What the fuck?” I cry as recognise the photo on his screen.

“Emily, what are you doing spying on me?”

“Jordy, what are you doing wanking to Tyler’s dick pics?”

We were both quiet for a moment as our minds whirled in different directions then wound back to the same place.

I turned around, pulled my hand out of my shorts, grabbed one of Jordy’s t-shirts off the floor to wipe my hand and my legs then I turned back.

“Jordy, that was your chance to tidy yourself up?” I told him.

“It’s my room, why should I?”

“Well, that’s your choice, but you’re going to lie there getting all sticky as you explain to me why you’re wanking to pictures of my boyfriend.”

“Err, well, I thought that would be obvious.”

I pushed Jordy’s legs away and sat on the edge of his bed, “so, you’re gay then, I kind of suspected. A good-looking lad like you, you should have a different girl every night, but you’re always here, alone.”

“Well, yeah, I’m gay, and as far as I can tell, I’m one of the only gays in school.”

“Oh shit, really, what about Nathan, I’m pretty sure he’s gay.”

“Nathan is an arsehole, If I came on to him everyone would know about it before the end of the day.”

“Does mum know?”

“Good god no.”

“I think she’d understand, dad never would, but he’s long gone. I think you should tell her.”

“Not yet ok.”

“Get yourself tidied up Jordy, I can’t concentrate with your cock lying there like that, and I need to talk to you about those pictures, like where you got them for a start.”

“Ok, I’ll go have a shower.”

I went back to my room, my knickers and shorts were a mess, I got the clothes I was going to wear later out and laid them on the bed, I was just getting undressed to have a shower when Jordy walked in the room wrapped in a big towel, oh well, payback for earlier I suppose, so I sat on my bed in just my soiled knickers, I guess if Jordy’s gay he won’t be too bothered by my boobs. I have nice boobs I think, well Tyler thinks so anyway.

Jordy sat on my desk chair, “ok Emily, let’s talk.”

“Where’d you get the photos Jordy?” I asked, well right now that was the most important question, I was praying Tyler didn’t send them to Jordy as well.

“I stole them from your phone,” Jordy said quietly, he’s a year older than me, but right now he was like a little brother, “I have an app running, all your photo stream comes to my phone...” I gasped, he’s seen the pics I sent Tyler, and Ryan “Oh don’t panic, all your selfies, I delete them, I just keep the pictures of Tyler. Look.”

Jordy unlocked his phone and handed it over, I opened his photos app and scrolled through, Tyler wasn’t the only boy he wanked over, there were a few more, none of me, and none of Ryan either, which is a relief, because Ryan took a few photos of us fucking.

“Who are the other boys?” I asked.

“Just guys off the internet, I don’t know their names.”

“When did you start stealing my photos Jordy, because there’s none of Ryan.”

“Ahh, I deleted those, he wasn’t worth wanking over.”

“There were pictures of me and Ryan, where are those?”

“I deleted those as well, I looked at them for a bit, just to see if they turned me on, and they didn’t, well not much, was he really fucking you in the bum, Emily?”

“mmm, yes,” I answered him quietly, a little ashamed, “we did it once, I enjoyed it less than he did.”

“Ahh ok, well I deleted them all, they’re gone.”

“You sure, I definitely don’t want any of my private photos anywhere other than my phone.”

“It’s ok sis, I spent one night trying to get turned on looking at you, and I couldn’t, so I deleted them all and emptied the recycling bin.”

“On that subject, is it just me, could it be that you weren’t turned on because I’m your sister? What about other girls?”

“I’ve tried other girls, I’ve tried all kinds of porn, I’m just into boys.”

I got up and walked over to Jordy, he was looking so sad just then, I couldn’t help myself, I pulled him to his feet and give him a good hug, it felt nice pressing my boobs against his hard, hairless chest, I got totally carried away, I kissed him and I’m not ashamed.

I pulled back when he didn’t respond.

“I’m so sorry, you might not fancy girls Jordy, but seriously, you’re fucking hot, and brother or not I’d fuck you right now.”

Jordy sat back down, I checked his towel, well I’m a girl, I have hormones, and I was a little bit surprised to see a small stirring under there, he was a bit excited.

“I stole your photos at first because I think you’re pretty, and if any girl could turn me on, I thought it would be you, and it just didn’t work for me.”

“Oh well, at least you tried, and I’m flattered you considered me as your model, so to speak. Look, I have to get ready to go out and I need a shower. If you ever want to talk about stuff, I’m here ok. Maybe I could ask around, see if any of my friends know any boys, you know, because with a bod like yours, you should have a boyfriend.”

“Thanks Emily, but right now I’m still coming to terms, you know, I’m not ready to come out.”

I kissed Jordy again, a quick kiss on his lips, “my lips are sealed.”

Jordy stood up, a little twitch under the towel again, mmm, maybe one day.

“Oh, by the way, I know you’re probably not the best person to ask this, but compared to other girls you’ve looked at, when you were experimenting, what do you think of my boobs?”

‘Correct, I’m not the best person to ask, boobs are boobs to me. Yours are quite big, and a nice shape, but ask a straight boy, like Tyler for instance, isn’t his opinion more important than mine?”

“I guess. He likes them, I just wanted a second opinion.”

That night I let Tyler fuck me, we were in the back of his car, he drives his mum’s old Volvo, with the back seats down it’s as big as a bed. We were parked behind the shopping centre, lying on a couple of sleeping bags it was quite comfortable.

Tyler is nice, his cock is bigger than Ryan’s and I could feel it properly, he lasted a few minutes as well, and I enjoyed it, but I feel I should have enjoyed it more, I would have, but I spent the whole time we were making out, the whole time I was blowing him to get him hard, and the whole time we were fucking, I spent all that time thinking about Jordy.

We’d drunk a bottle of wine between us, I had most of it because Tyler was driving. I’m not a big drinker, but even though I was determined to fuck Tyler today, especially after I left the house as hot as hell after my chat with Jordy, I still needed a bit of Dutch courage. So I was drunk, and I was horny, even after fucking, I still had an itch, so I was lying back, my hand absently playing with my pussy, Tyler was puffing on his e-cig. If he had one fault it was he smoked, I’d managed to stop him smoking actual cigarettes when he was round me, but he still insisted on sucking on the e-cig after we’d made out.

Anyway, I was absently wanking myself in the afterglow, head still spinning from the wine and the orgasm I’d given myself, yep Tyler didn’t manage to get me off, so that’s two strikes against him, so I wasn’t thinking straight when I said.

“I caught Jordy wanking over your dick pics this afternoon.”

Ahh, did I just say that?

‘What?”

Seems I did.

“Yeah, I walked past his room and saw him wanking,” let’s not make this too weird, I won’t mention getting myself off watching him for 5 minutes, “and like I noticed he had your pictures on his phone.”

‘Okayyyy, well that’s a bit weird, so I guess he’s gay then.”

“Yes, we had a chat, and he is.”

“I did wonder.”

“Hang on, aren’t you supposed to like, blow your top and be outraged at a boy wanking over your photos?”

“I find it flattering, you know, that a boy thinks I’m good enough to wank over.”

So, strike three, he’s vain.

“He’s a good-looking guy is Jordy, a nice body, and a fair bulge in his jeans.”

So, Tyler noticed Jordy’s body before I did, maybe I’m not the weird one here.

“I got totally hot watching him,” whoops, let that slip.

“Did you, like, see his cock?”

“Well duh, he was wanking, so yeah, I saw it.”

I didn’t mean that to sound quite so sarcastic, but this conversation isn’t moving in the direction I expected.

“So, does he have a nice cock?”

Okayyyy, definitely moving to a weird place right now.

“Define nice,” the only escape route that came to mind.

“Well, is it bigger or smaller than mine?”

“Oh, much bigger.”

Ahh, maybe shouldn’t have said that with quite so much enthusiasm.

“Longer and thicker, and really nice veins, it’s a proper porn star cock.”

Again, why am I trying to destroy my boyfriend’s ego?

“Ahh, that sounds nice.”

What the fuck, he’s not supposed to sound happy about Jordy’s cock putting his in the shade.

“That really isn’t how I expected you to react to that news.”

“Why not, I like looking at cocks as much as I like looking at boobs and pussies.”

“Tyler, is there something you need to tell me?”

“No, I don’t think so.”

“Well, look at it this way, you’re lying here in the afterglow of some quite nice sex with a sexy girl, and you seem to be lusting after the girl’s brother.”

“And?”

“Well, are you gay?”

“Oh no! Not gay, but I think I may be, what do you call it, bi-curious.”

“Ahh, ok.”

And then I had an idea, it hit me all of a sudden, a work of genius, and well, oh read on, I’ll explain it.

“Tyler?”

“What?”

“Don’t get mad, but how would you like to go on a double date one day?”

“Who with?”

“Well, is your Jess seeing anyone right now?”

“Mmm, this is a change of subject.”

“Not really, just hear me out, is Jess seeing anyone?”

“No, she dumped Ben and I don’t think she’s got anyone on the horizon.”

“Would it be out of the question for me, you, Jordy and Jess to go out one day, my mum is working nights this weekend, our house will be free, we could watch a film, order in some pizza and wine, and we could see where the night takes us.”

“Are you thinking of hitting on Jess, because I don’t think she’s into girls.”

“I don’t think I am, but you asking after Jordy’s cock just got me thinking.”

“Ok, I see where you’re going, but if I fuck Jordy, will you still want to see me?”

I kissed Tyler, suddenly extremely horny from thinking about the possibilities Saturday night held, and any possible fall out very far from my mind.

“We’ll cross that bridge when we come to it, in the meantime I need to cum again, either you can fuck me or I’ll do it myself.

He fucked me, twice, once in each hole, but I still had to finish myself off, oh well.

Saturday afternoon, Tyler had persuaded Jess to join our double date, although right now she thought she was dating Jordy.

Tyler is my year in school, we’re Lower Sixth, Year 12, Jordy is Upper Sixth, Year 13, Jess is a year younger, she’s Year 11 and as pretty as a picture, she’s delicate, with alabaster skin and jet black hair, she’s got just the sweetest little boobs and a peachy bum, maybe I do fancy her a bit, but it’s just a standard girl crush, we all have them, don’t we.

I spent the afternoon tiding up, mum didn’t run a tight ship at home, she did two jobs so wasn’t really awake much at home, so maybe we didn’t have the cleanest house on the block, so this afternoon me and Jordy gave the lounge, kitchen and our bedrooms a thorough cleaning, and when we finished I was actually a bit house proud, it looked good.

Tyler and Jess were due at 6, so I phoned an order through to Dominos for delivery at 6:30 and sent Jordy out to Bargain Booze to find a few bottles of cheap chardonnay.

I was actually nervous as the clock on the mantlepiece clicked around to 6 and felt utterly devastated when the doorbell didn’t ring as the clock chimed the hour.

Jess had backed out.

Or maybe Tyler had backed out.

 
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