Um Both I Guess

So far:

I fancy my slightly older sister, Jenny. It seems mutual. We have played a clothes swapping game. She wanted to watch me wear more of her clothes and wank while she fingered herself underneath a blanket. Jenny played with my cock and we told each other our fantasies. Mine are about being dominated. Hers was about watching me have sex with another boy - and it made me cum in front of her.

We swapped underpants and met up during lunchtime at school to show and tell. When we got home she asked me to wank for her and gave me a female anatomy lesson. I kissed her arse and watched her wank while I started to tell her about the time I jerked off with a male friend, she watched me cum into her panties at the same time she came while fingering herself. She wiped her cunt juice on my shoulder.

A few days later Jenny wanted to practice fitting a condom to my erect cock.

Overview of this chapter:

Jenny fits the condom, watches me wank, and gets up nerve to ask me if I want to lick her cunt. We visit the beach and make plans for our 'weekend of sin' (her actual words).

Jenny took hold of the shaft of my cock with her left hand to steady it. Her hands felt so warm and dry; my hands were trembling and my palms were sweaty but my sister's hands were rock steady and her palms were dry. It was truly all I could do to keep from spurting all over her hand. Her thumb and forefinger were circled, firmly, just below the head.

Then Jenny knelt down and bent over - not far - just a half bow. Her hair fell forward and brushed my cock. I felt her hot breath on my belly and cock. Then she gently placed the rolled condom loosely on the head of my cock. She looked up to make eye contact,

'How does it feel, Ian?'

'Really good. I love it when you touch me. I love it when we do anything.'

Jenny shook her head making the tips of her hair tickle the shaft of my cock.

'No, I mean how does the condom feel?'

'Well you haven't got it on yet. Do you want me to do it?' I asked hoping she'd say no. Jenny was intent on doing this unaided and shook her head again. The smell of her hair - green apples - as it brushed my cock -- was driving me wild even though it was the same shampoo I used.

Using both hands now my sister began to roll the condom down. Then she stopped. The broomsticks at school were all smooth shafts and I realised that Jenny had no idea how to get the condom over the edge of the glans.

I started to reach down to help but I needn't have worried because she was good. I barely noticed it as the condom snicked over my glans. I didn't really feel anything until she used both hands - one on either side - to rapidly roll the condom down the rest of the shaft. That I did feel.

I gave a wee lurch and a gasp from excitement and Jenny looked up.

'What's wrong? Did I hurt you? I'm sorry.'

'No, no, you didn't hurt me. It just felt so good when you did that.'

I daresay that the broomstick she had previously practiced on was less sensitive than her brother's penis and didn't mind a fast unrolling. But not to worry. I was now fully clothed, so to speak.

Jenny stood up and stepped back to admire her handiwork. She reached down and jiggled the rubber ring to check it was forming a seal and checked the teat wasn't inflated - just as the embarrassing school lessons had told us to do.

'Well how does it feel now? Is it too tight? Too loose? They said you can get other sizes but for almost all men like you the normal ones will fit. Hmm, actually I can see it is a good fit.'

Men! I heard that! My teenage sister has just put a condom on me and described me as having a man's cock!

'Is it ok having it all squeezed in like that? Look, I can see the veins all bulging.'

'It feels fantastic Jenny. I mean it. Thank you so much for doing this with me. What do you want to do now?'

Jenny told me to stop and wait. She was still kneeling - with her knees about as far apart has her shoulders. She bent backwards a little, arching her back, slipped her hand down into the pair of my underpants she was wearing, and gave herself a good rub.

Clearly I was staring and she seemed to feel an explanation was due.

'Just spreading some of the juices. Here.'

"Here" meant she pulled her hand out and raised her finger so I could see the glistening. She stood up and put her ankles together. She stuck a thumb in either side at her hips and peeled the underpants down - man I loved the way she did that. Then she stepped out of my underpants and kicked them to the side. She lay back on her bed and spread her legs. She began rubbing in a circle.

I couldn't really see much detail as her hand and cunt hair was in the way. But I could see enough, she had her first two fingers stretched out in a sort of Spock symbol. The fingers were towards the top of her cunt and on either side of where I knew her clit was. She was rubbing in a circle but without the fingertips moving from where they were pressing. I could see flashes of the pink of her inner lips - the labia minora as I now knew they were called - with each turn of the circle she was rubbing. Her other fingers rested at the entrance to her cunt.

'More please' I begged. I knew I'd said the right thing because she gave her wee triumphant smile

I looked at the condom and asked 'Shall I take it off?'

'Umm not right now. Would it be OK if we checked how it works?'

I practically came there and then. Surely she didn't mean...? Jenny saw the look that had flicked across my face.

'No, I don't mean that. Anyway, not yet', she said. 'Or maybe never' she added hurriedly.

But she had said "yet". Maybe one day?

She clarified; 'I mean I want to see what happens when you, you know, when you umm cum inside it. Will that be ok?'

She was cajoling now but she should have known that I was hers to command. Would it be OK? Did she really need to ask?

'Yes, please, Jenny, please, I really want to show you.'

We'd done this sort of thing before. Jenny was watching me wank while she sat on her bed with her legs spread and her hand reaching down the waistband of the pair of my underpants she was wearing. But this time she was naked and I could see her cunt wide open.

'No Ian, what I mean is, can I do it this time?'

I almost came then. My sister had just asked permission to jerk me off. I suddenly guessed she had wanted to do this without getting cum all over her and come up with the idea of putting a condom on me for this reason. Well, I sure as hell didn't mind. It wasn't going to be skin to skin contact but it was still going to be my sister holding my cock.

'Sure, I would really like that Jenny. I usually do it like this.'

I took a grip and gave an experimental tug. I was surprised at how little difference I noticed and told her so.

I closed my eyes for a moment and then felt Jenny's hand peel my own hand away and take over the jerking. I snapped my eyes open and could see all the fingers of her other hand were buried up to the palm knuckles in her cunt. Naturally I came instantly, but if Jenny noticed she didn't show it and she continued to tug on my now quite sensitive cock for a few more seconds before she closed her eyes and gave several big heaves.

She squeezed my cock hard and clenched her thighs around the fingers in her cunt and shuddered a few more times. Then she opened her eyes, let go of my cock and parted her thighs. I bent closer to watch her pull out the fingers from her cunt. Her fingers were totally dripping and I wanted so much to suck them clean.

'Can I...?'

Jenny held up her hand and I leaned forward and took those fingers into my mouth. I closed my lips around the 3rd knuckle and moved my head back to slurp her fingers clean. In all the years since then I, have never forgotten the taste of her teenage cunt juice.

'More please Jenny?'

'Soon Ian. Not this time, but soon. Wait for Festival weekend.'

She said this with a sly grin. My sister knew exactly how crazy she was making me. (If you have been paying attention you'll know that Jenny and I are going to be left at home for a 3 day weekend while our parents go to a folk music festival).

And again there was the odd guilty thing as our breathing slowed and we did the by now routine job of cleaning up and practically pretending nothing had happened.

But this time as we were about to go to the living room to watch TV shortly before we expected Mum and Dad to get home, Jenny said:

'I will have sex lots of times in my life but I the first time should be with somebody who will always be important to you. Lots of things will change in our lives but we'll always be, sister and brother. Some of the girls at school have had sex and already can't stand the boy. So we should be the first for each other. And I mean we should make sure that we do everything first with each other.'

As I have said repeatedly, Jenny had given this a lot more thought than me. I was still trying to get my head around the idea of watching my sister masturbate and here she was talking about doing 'everything'. I didn't have the faintest idea what she was getting at and it seemed safest to admit this.

'Umm sure, I agree the first time should be with a special person and you are the most special person to me Jenny. Got it. But what sort of everything do you mean?'

'Oh come on Ian, you must have heard or read about things other than just fucking'.

Holy crap, when you have just watched your sister sitting naked with several of her own fingers dipped in her cunt, and she is watching your stroke your cock while you are wearing her panties, the word 'fucking' is really, really a turn on.

'What do you have in mind?'

I had always been good at hearing the feeling behind her words and I could easily tell my sister was insecure and uncertain when she next said 'Do you really like the taste of me, from umm, down there?'

I was smart enough to know the right answer.

'Oh yes Jenny. I really, really like the taste of your juices.'

'Well, do you want more?'

Huh? For a smart girl my sister sure was dumb sometimes. What sort of question was it to ask if I wanted to taste more of her cunt juices? Of course I did! I took a deep breath and tried to speak slowly and calmly.

'Yes. Please Jenny. I really like the taste of you and I really want more.'

'Well', she began, 'I got this from Leanne who got it from Justine.'

Leanne, if you have been paying attention, is Jenny's best friend and who happens to share her birthday. Justine was Leanne's older sister. She was about 7 years older than us, 'practically married' and knew 'ever so much about sex.'

'This' turned out to be an article torn from Cosmopolitan. I don't know what Cosmo is like now - the covers I see in waiting rooms suggest little has changed - but back then it was essentially a sex manual for virgin teen girls and the recently deflowered and looking for better quality sex.

I bet it was, and is, written by a bunch of 40-something guys with teenage girls working as interns and allowed to do the makeup column in exchange for a blow job. But nevertheless it did have a lot of sex tips.

Jenny passed it to me, 'Read this.'

The article was titled How to get the best sex of your life from the man of your life. I caught the last part of the title first and was suddenly thrilled to realise that maybe we were the man and woman of each other's' lives. Then the first part of the title sank in. Wow. My sister Jenny wanted sex with me. And, in a totally not amazing coincidence, I wanted sex with her.

Jenny was pointing at a list "10 things to do and have done before you settle down". Jenny's finger was tapping at number 4 'Get into the groove: Cunnilingus'. (I saw that number 6 was 'Give a mind blowing blowjob').

Cunnilingus. I knew what that meant. It meant cunt licking. Every time I read about cunt licking in Penthouse etc. it got me hard. It was really something I wanted to do and Jenny was the one I had most imagined doing it with.

Jenny reached out a hand and took the article back, 'Would you like me to read it out to you?'

'Oh, yes please'

Jenny knew how much I like hearing her 'talk dirty'. She patted her bed and I sat next to her.

The entry on cunt licking was only about 300 or 400 words long and not very detailed but I listened. Heck, my teachers would never have believed it because I practically committed it to memory. Have you read any Cosmo sex guides? All a bit like that movie American Pie - exotic names for the commonplace. Well, I say that now with many years hindsight, but at the time I was spellbound.

Gentle sucking, heavy breathing, how to tell a man to gently nibble or more forcefully nip, it was all there. Paramount in my thoughts was that my sister Jenny wanted me to do this to her.

In retrospect I suppose you could say it was empowering because the message was:

a) The clit is the only organ in either sex that has no other purpose except to feel pleasure

b) A woman should seek pleasure and tell her partner how to give it.

I honestly believe that always, always, following these principles has given me a better sex life than most men.

Jenny finished reading and looked at me with a question hovering on her lips. In answer I slipped to my knees, and bent right over to kiss her bare feet.

'Yes. Please let me do that for you Jenny. I want to lick my sister's cunt. I want to make you squirm with desire.' (That was a phrase from the article).

'Good. Next time then. Right now we have to get to the lounge and look innocent.'

How the heck did she go from jilling off in front of her brother to watching sitcoms in just a few seconds?

Yes, yes, I knew number 6 was about sucking cock. But I wasn't particularly obsessed with getting a blow job from my sister. What was I obsessed with? Well, if I got to lick her cunt then I hoped that if I was really good she would lose bladder control and piss in my mouth. There. I had admitted it to myself. Could I admit it to Jenny?

The next day was Saturday. Mum was all super nice the next morning. She had said that last night at the Folk Music Club before the Festival (yeah, you could hear all the capitals when she said it) they had invited some friends over today to practice an item for the Festival.

In case you have forgotten, in a few days, our parents are going away for a 3 day weekend to a folk music festival and are going to leave me and Jenny home alone. Anyhow, Mum said we might like to clear out of the house for a few hours and go to the beach. We were both strong swimmers and spent a lot of time at the beach, often going together or with friends.

Mum gave us some money for the bus and some more for food. Now, this was a little surprising. I mean, our parents loved us and all that but they also felt we needed to be responsible for ourselves, especially when it came to luxuries. They seldom paid for us to do things like that.

My guess (and Jenny agreed when we had a quiet chat) was that Mum and Dad wanted some peace and quiet for a good fuck before their friends came over so they wanted us out asap. We were both cool with that. Having let off steam yesterday, we were both keen to 'spend some quality time'. Or, in other words, plan out how we were going to spend that long weekend.

The problem had been that any alone time we had we always seemed to spend doing sexy things. And afterwards it always felt too weird to talk about it at home. So, a couple of hours alone someplace else, out of the house, was just what we needed.

On the walk to the bus and while we were waiting, we talked aimlessly about music. Jenny said we could wait till we got to the beach to talk about our 'weekend of sin'. Yep, that's what she called it. I hasten to add that to both us 'sin' just meant 'naughty'. We were never exposed to any religious stuff and did not think for a second that what we were doing was morally wrong. How could something that felt so good be wrong? I mean, if we were not related then most people would think we were lucky to have a loving partner for our first sexual experiences.

On the bus it was like buses always are; noisy. We took the seat directly in front of the rear door. This meant no one would be close. We waited tensely until the bus left our neighbourhood. If anyone we knew had go on then they would likely also be going to the beach and we would probably have had to talk to them.

At the beach Jenny pulled off her outer clothes. No, not like that. I mean that we had our togs on underneath. [Togs = swimming clothes]. I had hibiscus printed board shorts and a reddish long sleeve shirt. (Aussie sun is fierce and we always covered up sensibly). Jenny had simply pulled down her skirt and unbuttoned her shirt to reveal a one piece costume. I mean one of the ones that covers the entire front from crotch to neckline and covers the back from bum to neckline. It was a light purple with darker purple trim. She picked up her silk blouse to cover her arms and we both put our hats back on.

In later years I noticed that some girls often had to run a finger round the leg hole of their togs to push back stray pubes, but not Jenny. I was feeling confident and ran my eyes over her before telling her she had nice curves. Jenny waved the compliment away as we shook our towels out and put down the lunch bag.

Direct and to the point as always, Jenny began:

'It gets a bit tender, but I can orgasm maybe 6 times in a day - not counting multiples at one time. How many times do you reckon you can cum in a 4 night and 3 day period?'

Even though we had expressly planned on talking about sex, this was a quite abrupt start and I paused a moment - looking up and down the still quite empty beach. I turned and looked directly at Jenny's face.

As always there was no point lying with my sister.

'If it was with someone as sexy and hot as you Jenny, then I can do 6 times in the first 24 hours and probably only 4 times per 24 hours after that'.

'So, a maximum of 15 or 16 times?'

'Yeah, but I have to be honest, my dick might be hard but some of those later cums would be almost straight water.'

'OK. So how about we make a plan for a dozen cums and save any others for spares?'

Yes. My head was spinning too. My sister had just matter-of-factly set a target for us to cum together a dozen times over a long weekend, and now she wanted to make detailed plans for each of those dozen times.

For a moment all I could do was stare at her right ear. She had a plain gold stud in each ear and her hair curled around the ear. Between earlobe and shoulder was a patch of short, pale hairs that were slowly rising. Just like the horror stories say, except this had to be due to sexual arousal.

'You know Ian, I haven't said this before but I really like the way you look at my head and face, even though we are talking about sex. Most boys always look at a girl's tits. At school we always joke that any boy who takes the time to look at a girl's face deserves at least a kiss but, you know, it isn't really a joke. Take this as a tip: If you want to fuck a girl, look at her face and tell her she is smart or funny, or whatever, just don't look at her tits and don't say she is pretty. We won't believe you and we'll just think you are saying it to try get sex.'

I felt oddly both guilty and not guilty. I have trouble reading faces, today I'd be labelled as partly Asperger's, so I often looked down and I just now realised that some girls probably thought I was staring at their tits.