High school holidays were always something I looked forward to, it was a time to just live at the pace of life that suits an 18yr olds life. Sleeping in late, going to bed late (if at all) – and in summer, staying outside or at a friend’s house until well into the evening – with enough sunlight to still be home before dark.
The one downside of school holidays is that with both my parents working, I was often left to “mind” my little sister. She was only 18 months’ younger than me, but unless she had arranged to head off to a friend’s house or visit our cousins, I had to stay home “just in case something happened” – she could fend for herself, but my parents were pretty firm on that rule. I would often try and get my mates to come and visit me – but they had the better computers, the game consoles and generally it was just more fun to visit them.
On the days when I was “baby sitting”, the main activities were watching TV, playing a computer game or playing outside with the dog. I might shoot some basketball for a bit – getting some sun on my skin. I wasn’t a muscley teenager, but not skinny – probably lean is the right word. I was a good runner, did rock climbing and hiking, and was generally fit. I was definitely at the age that I wanted girls to notice me, so I tried to make a bit of an effort. Abs was the main thing – if I had good abs on display the pool or the lake, that was sure to win me a hotties attention.
My sister, Jess, was basically the slim, athletic female equivalent of myself – she was 5’5” to my 5’9”, 50kg to my 70kg, and of course, she had breasts – nice developing teenage breasts. She was a hottie. She wasn’t the hottest girl in school type hot, she was girl-next door hot. Cute and innocent… and maybe corruptible.
Jess and I had a good relationship – we played a lot of games together growing up. She wanted a ‘husband’ for her game, so that was me in dress up’s coming home from work – etc. I wanted someone to chase on a bike outside or build a cubby with – so she got her hands dirty. You get the picture – we got along fine. Being a bit older now, we had drifted apart in the sense we both had our own friends and were starting to be busy with our own social lives.
One thing I was very busy with was masturbating. Pretty much every day, often twice and sex was on my mind constantly. I didn’t necessarily want or need to have sex; I just wanted to orgasm and get a load away. I found all sorts of ways to masturbate – I would rub the head of my dick gently alongside inside of my thigh, I would use a soft cotton sock, I would stand at the corner of my desk and just gentle put weight on my perineum (that muscle between my balls and arse). I didn’t need much to get off – but I enjoyed finding all sort of ways to do it.
It was during one of my days stuck at home with my sister – that it occurred to me that maybe I could fuck her, or at least get to jerk off on her, with her, just something a bit different. Fucking her would be the ultimate goal, but if she just watched me wank off, that would be fine too. I don’t know what lead to this idea forming, it probably just appeared out of the blue like teenage dirty ideas do. But once it was in my mind, it was in my mind.
My first try to make this a reality was a day when my parents went out until late in the evening. They said they probably wouldn’t be home until after 11pm, which for me meant that I had a few hours after dinner to make it happen. Casually I suggested that we should have a sleep over, like in the old days, she could sleep on a spare mattress in my room and we could watch a movie in there. Jess was happy with the idea, as it did sound fun.
After mum and dad had left, we did dinner, had showers and then setup our sleep over arrangement. I put the spare mattress on the floor next to my bed and Jess dragged her pillows and quilt in. Jess had already got into her pjs, shorts and a loose top. I had decided that I needed to keep some restriction on my dick (initially), so kept my jocks and footy shorts on, and a t-shirt. After ***********ing a movie and letting it run for a short while, I piped up: “hey, this is sort of boring, do you want to play truth or dare”.
“alright”, said Jess, “but nothing to crazy”. Excellent I thought, but it all depends what you think is crazy.
The game started normally, just basic questions, mostly truths, not many dares. I started to lean the questions toward if she had a boyfriend (no), she asked if I had a girlfriend (no), had I kissed anyone (yes) etc. Slowly and slowly the questions were getting to the inevitable sexual activities.
“Truth or Dare”, I asked her.
“Truth” Jess replied.
“Okay – have any guy or guys seen you naked?”
“What! Of course not!” Jess blurted out “Why, how many girls have you seen nude?”.
“Well, none actually – except in magazines. But I don’t think it is the same – real life would be much nicer”. I replied, trying to keep the conversation going.
“Oh yeah, I bet. Your turn, truth or dare?” continued Jess.
“No No.”, I protested “You asked me a truth just before, so it is actually your turn again.” I said jokingly. I was happy she accepted that I did answer a truth, so it was her turn.
“Okay fine – I will go a dare this time”. This surprised me – this was the first dare of the night, I decided to risk it.
“Okay. I dare you to show me your breasts”.
“No! You can’t dare me to do that…”. Maybe I had gone too far.
I was just about to retract the dare when she said “I will do it, but you have to do a strip tease dance for me. Haha!”.
“ahhh… okay” I replied nervously (though amazingly excited and getting harder by the second). “You give me a min-top half only strip tease, and I will give you one back”. I couldn’t have been happier; I was going to get my dick out in front of my little sister.
I didn’t care what happened after that, I could jerk off for weeks to the memory of knowing she had seen my naked and hard!
Jess jumped up, turned out and took off her top. She then spun around and in the soft light of the bedroom lamp I got a look at her sexy little breasts for the first time. After what seemed like a millisecond, she spun back around and slipped her top back on.
“There – your turn” she said, in a rather inviting way.
It was my turn. I was honestly nervous, but equally excited. I stood up and took off my top. I decided to stay facing her, and just whip off my pants and free my very hard dick; so I did.
I just reached down and pulled off my short and undies, then stood back up and looked around with a nervous smile. I didn’t know if I should make eye contact with her or what.
I decided to just double down on the situation and point out the elephant in the room. “Yeah, so it is obviously hard because, it was pretty cool seeing your breasts and obviously this is a bit of a naughty thing to be stripping for you.”
Jess just sort of nodded in an agreeing way: yes it was hard, yes you did see my breasts, yes this is naughty.
I threw down a second time – all in!
“Ummm, so can I see you fully naked? You have seen me, and not just naked like in the shower, but with a full hard on!”. I said with a bit of a joking tone.
Jess looked up and me, looked back generally toward my hard dick that the whole time was just pointed at her – and right about her eye height – and then said “Yeah, okay… sit on the bed… you can put you pants back on if you like.”
“I am okay” I replied, sitting on my bed (well, sort of perching my butt on the edge). There was no way my dick was going back into the clothing until I have relieved the load that was building in me.
Jess didn’t mess around, she just stood up and then facing me, pulled off her top again, and then pulled down her shorts. She wasn’t wearing anything else, and there I had it, my little sister naked in front of me.
She was cute. Slim in the waist, with just a little bit of hip. She stood with her legs together, one slightly in front of the other, so her pussy wasn’t fully on display for me, but she had the slightest of pubic hair showing. Maybe she trims it I thought – but maybe that was just as long as it was at her age.
“Very cute” I said. “Can I have a twirl”. Jess obliged and I got a nice little very of her arse. Oh my, her arse. I wanted to grab it. It looked so beautifully soft. I instantly wondered what it would feel like to rub myself across her arse, or between her cheeks. My mind was going every which way.
“Okay – that was fun” she said, and moved get her clothes back on.
“No wait” I interjected. “Like, look, I am super hard, and I was thinking, maybe if you don’t mind I could just masturbate right now. You could watch, or you could just go, sorry… ”. My god – I had completely committed.
“What the fuck! You want to jerk off right now.” She sounded pissed off.
“Ummm, well yeah. Like if you leave, I am going to do it straight away and honestly, I am going to think about you naked while I do… you have never seen a guy masturbate, or cum, so maybe it would be interesting?”. I was struggling to make this sound like an attractive offer – but she hadn’t stormed out yet.
“Okay, I will let you look at me while you jerk off, and yes, I want to see what happens when you cum. So how do you want to do this?”.
I was in heaven! I couldn’t hide my excitement.
“Alright – I am going to sit like this on the bed”, as I moved myself into a comfy position, legs spread apart and just in the most gentle of squats, my bum almost leaning against the side of the bed. She would get a good view, and I would get a good view of her. “You can sit down here if you like”, I said pointing to the mattress on the floor below and slightly in front of me. If I did shoot a bit load of cum, it probably wouldn’t hit her – but it would make a mess.
“Sorry, can you grab the towel and put it on the floor between me and you… I normally jerk off into sock or something, so there is no mess”.
And with that I started to work away on myself, with Jess kneeling attentively just a few feet away. Her eyes flicked from watching my dick to my eyes and back again. My eyes flicked from her breasts to her eyes, to her pussy… which I still didn’t get a great view of. I wanted more.
“Jess, can you show me more of your pussy please? Like spread your legs a bit more?” – I said somewhat pleadingly.
She didn’t say anything but spread her knees a little and lent back slightly, giving me a glimpse of her pussy lips just every so gently pulling apart. She looked back at me and I nodded with approval and breathed out with satisfaction. It never took me long to cum, and this was not going to be any exception.
“Okay, I am pretty close to cumming… do you want me to just shoot it out on the towel?”
“Yeah, but move your hand a bit more slowly so I can see when it happens”.
With that I slowed down for my final few beats, and then utter relief as the first stream of cum came out and landed on the towel. Followed by a second and third… I kept jerking as my breathing slowed down and I finally stopped.
My cum had gone a good two feet, landing only about 6 inches from Jess’ pussy. My dirty mind instantly regretted not actually hitting her with some cum – she would then have had to touch it, wipe it off – maybe she would have played with it a bit or tasted it. Who knows! But I guess that would be motivation for next time.
“Feeling better?” Jess asked with a chuckle.
“Ummm, yeah, that was fun… Ummm, are you all good… do you masturbate, or do you want to do that…?” I asked in a trying not to be selfish kind of way.
“I am alright just at this moment… I haven’t really got into playing with myself yet… but I enjoyed watching you, and I am glad you got that out of your system.” she smiled.
No – not out of my system, my mind raced… now this is firmly in my system. And I want more.