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.

Overview of this chapter:

Jenny wanks while I tell her about jerking off with a male friend, she watches me cum into her panties at the same time she cums while fingering herself. She wipes her cunt juice on my shoulder. A few days later Jenny wants to practice fitting a condom to my erect cock.

***

My sister Jenny is as turned on by gay sex as I am by lesbian sex and she is letting me watch her wank while I tell her about my fooling around with a male friend.

'OK, but don't be mad. So a couple of times me and Mike have read the porn mags and wanked in our sleeping bags. We don't see each other's cocks but we are both wanking. Well, I kind of always wanted to watch Mike cum and I wanted him to watch me come.'

'Do you think you are a bit gay?'

'I don't think so, I think about girls most of the time but I get so horny that I just don't care. Anyhow, you know Mike fancies you, right? Well, I told him how you often walked around in panties and a t-shirt. And, so Mike was really turned on about the panties and I ended up telling him that I sometimes wore yours.'

'What! You told Mike that you wore your sister's panties? He could have told people and you would have been so laughed at!'

'Nah, it was cool. He thought it was the sexiest idea ever and said he wished he had a sister so he could do the same. So, then I said I'd get him a pair to wear next time he had a sleepover.'

'Oh Ian, please don't tell me you let Mike wear my panties, I mean...'

I interrupted, 'Well, yes I did but it was worn ones from the laundry basket so they got washed before you wore them again.'

Jenny was still caressing her nipples but had mostly stopped touching any part of her cunt.

'OK, carry on with the story then.'

'Well, the next time he stayed over we did it. I swiped two pairs and we put them on. It was super sexy to be sitting at dinner and thinking about how our cocks were stretching out panties that had been next to your cunt.' I stroked my erection through the pair of Jenny's panties I had now.

'And?' Jenny spread her legs wider and began to seriously masturbate - not the idle twiddling of the last few minutes. Jenny used two fingers of her right hand to twiddle away at her clit.

'After everyone had gone to bed we showed each other how we looked in panties. Then we got the mags and started to wank while we watched each other.'

If you have never seen a teenage girl masturbate then you have really missed out.

Jenny also tweaked her nipples with her left hand. She was thrusting her hips so she mashed her cunt onto her fingers. Of course I had also started stroking my erect cock wrapped in her panties. But my attention was glued on watching her cunt and she had to keep reminding me to continue describing mine and Mike's wanking together. [I will write this story up as soon as I finish "Umm, both, I guess"]

'Hurry Ian, I am going to cum really soon.'

And at that point the idea of wanking with my best friend while my sister watched was too much. I couldn't take it anymore and warned her that I was about to cum.

'Go on then Ian, cum while I watch.'

'OK, I'll skip some bits - I can tell you next time - and, well I came really quickly and, well, and I nearly let Mike fuck my bum, only he came as well.'

I held my breath and tensed. I couldn't take it anymore and squirted a huge wad of cum into my hand and over her panties. No, my panties that my sister had given me to wear. Jenny leaned over for a better look and with a loud sigh of satisfaction thrust her hips forward as she took her hand away from her cunt. Had she just come as well?

We looked at each other in surprise. I don't think either of us had expected things to go quite as far as they had. There was a very awkward silence while we caught our breath. Jenny was the first to speak. 'Thank you Ian. I had a lovely time. I suppose we had better get cleaned up now.'

What the fuck? Jenny was using her polite voice to say that her wanking while she watched me wank was 'a lovely time'?? I didn't know what to say but I knew that in all things to do with these sessions she was the boss but I had to try something.

I remembered a scene from a Penthouse Forum letter and got down on my knees. I told Jenny that I was hers to do with as she pleased and my only object was to bring her pleasure. Then I kissed her feet. She stood frozen humming - she really seemed to enjoy that. Then she put her hand - the one that had been deep in her cunt - on my shoulder. I could smell her cunt! Her cunt juices were on my shoulder! As I turned my head she moved her hand and I kissed where it had been. Jenny knew exactly what I was doing.

Do you remember the first time you tasted cunt juices? It was all that and more because it was my sister. The juices were tangy, sweet and salty all at the same time. I kissed where her hand had been again and then got down and kissed her feet again.

'No, come on Ian, later.'

Later. Joy! There was going to be a 'later' and an 'again'! I got to my feet and slowly peeled off the panties while Jenny quickly dressed. When she looked over again I was still naked with a growing half erection holding her panties in my hands.

'Ian, get on with it'

I got dressed and rinsed the panties in the bathroom sink and put them in the laundry. When I went to find Jenny she was sitting in front of the TV wearing a t-shirt with no bra and jeans.

'Ian. Brother', she paused when she said 'brother' and rubbed a nipple trough the t-shirt. 'Oh my brother. I didn't plan on going that far. I had just thought we'd wear each other's clothes but...,'

'Wait a minute!' I started, 'you planned for us to, to, um to, to um, do stuff'?

Jenny, my sexy and calculating sister Jenny, gave me a pitying look.

'Ian, oh brother of mine, if I hadn't started things then do you think you would have ever had the courage? When I grew my tits and I saw you looking at them I started to think about you. Like you said, the naughtiness of it being my brother is really sexy.'

She stood up reached her hands around my neck.

'But Ian. I'm not sure if we should do this again. I need to think. And even if we do: We. Must. Not. Get. Caught. Understand? We have to behave like normal. That means no touching or naughty talk when Mum and Dad are home. Ever.'

I sagged a little but saw the sense.

'Sure. That was a bit much. '

Somehow we got food, watched TV - with Jenny acting like nothing had happened - and went to bed before our parents came home.

I wish I could say we quickly progressed to fucking but we didn't. (We did get there but it took time). For two weeks we were respectful but a little distant from each other. I suppose Jenny was thinking things through. Being a boy, I didn't have much thinking to do.

Compared to some other countries, Australia has a decent number public holidays (12 at this time) and, apart from actual anniversaries like ANZAC Day, those that fall between Tuesday to Thursday are usually 'Monday-ised' and observed on Monday instead of the actual day, so you get a 3-day weekend.

The annual folk music festival was always on Labor-day weekend in early October (mid-spring). In three weeks our parents were going to leave before we got back from school on Friday and wouldn't be back until late on Monday.

3 days. 3 nights. Just us.

Jenny made it clear that this was going to be a special weekend and my cock was raw from wanking and thinking of my sister. Then two things happened.

First Mum and Dad did as they'd said and put a bowl of condoms on the hall table. It was excruciatingly embarrassing. Nobody else's parents had done anything like this. It was embarrassing to try tell them with a straight face that I knew about sex but wasn't getting any so I didn't need the condoms. I did overhear Jenny saying pretty much the same thing to Mum. But it was practically like they wanted us to have sex. I don't mean that our parents wanted their son and daughter to have sex with each other but that our parents wanted their kids to be having sex with boyfriends and girlfriends.

In fact, I think they were both a bit disappointed that we both seemed to be straight. I think they wanted the social cool factor with their friends of being able to say one or both of their kids was gay and how much they supported us. If they couldn't have that then they wanted the next best thing - for us to be sexually active at an early age.

Damn it, they even left a leaflet of 'A-Z of Safe sex acts'. It was a list with cartoon drawing of 26 safe sex acts. It had been produced by some AIDS campaign group. Me and Jenny wanted nothing to do with it and said so. But I know I sneaked a look one night and was astounded. Dad's Penthouses were way behind the times!

Jenny had a look too. I certainly know that Mum was ostentatiously careful to never glance at the leaflet, thereby telling us that she was watching us like a hawk and waiting to pounce and offer advice. So, in turn, we knew instinctively to avoid showing any interest in anything of the sort.

Hell, I even gave up reading the junk mail for a week. I don't know if it was deliberate and I don't know of it still happens, but back then we got a lot of junk mail leaflets for chain stores with a presence in town. The underwear and sleepwear ads were total jailbait and I bet they don't make them like that anymore.

Young women and girls posing in undies or nighties with arms crossed or their nipples visibly poking up beneath the fabric. I'd heard that a girl at our school did modelling for clothes that one of the chains carried, but I never saw her in any ads. But boy, I sure glued a lot of glossy pages together thinking about how great it would be if Jenny did modelling like that.

And the second thing? Well, it was Thursday evening so everyone was home and I was walking down the hallway past her bedroom door. The door was half open and as I drew level Jenny stepped sideways from behind the door and beckoned. I swear I noticed her face and the hesitant smile before I noticed that all she was wearing was a short t-shirt and a pair of my underpants. They bulged out oddly at the front like she had a sock stuffed down.

'I borrowed these, Ian. I hope you don't mind?'

As I stood there gaping like a fish she slipped her hand down the front and began to rub the sock. Then she pulled the sock out. It wasn't a sock. It was a wadded up pair of her light blue 'boy short' panties. She pushed them into my hand.

'Here, take these to get in the mood for tomorrow. I have an idea you'll like. But you need to, umm, save, umm, it.' She looked at me questioningly to see if I got what she meant. I did. I wasn't to cum before tomorrow. I nodded that I understood.

I never needed help to get in the mood for a session with Jenny and my erection was straining as I stared at her crotch. Sweet sister of mine that she was, she followed my gaze. Then Jenny slipped her hand back down the front of my underpants that she was wearing. This time when she pulled her hand out she had one finger extended.

Jenny lifted the finger to my face and pushed it between my lips. I sucked and I was tasting my sister's cunt juices for the second time! (Though that lick off my shoulder hardly counted). Salty but oh so sweet, I was in agony. I wanted to jerk myself into a stupor but I knew I should hold out until tomorrow. Jenny stepped back into her room and quietly shut the door.

How did she do that? Be so restrained. What the hell did she have in mind? I knew, even in my wildest dreams - which were pretty wild - that we were not going to fuck but I also realised she had something special planned.

I managed to refrain from wanking that night only by imagining the joys to come and went to school in the morning wearing her panties. Don't get me wrong. There had been a time a few months ago when the thought of wearing her panties to school would have been sufficient to have me cum on the spot. And here I was doing it with not only with her knowledge but actually at her suggestion. So again, I had a great day and was perpetually stiff. This time though I didn't jerk off in one of the toilets.

We didn't meet during the day at school and we walked home with friends with us until our gateway, so I didn't get a chance to try find out about this plan of Jenny's. We got inside the house and as usual we had several hours before mum and Dad returned.

We dropped our school bags and looked at each other awkwardly. Then, checking the front door was locked, we went to her room.

Jenny wasted no time in explaining her plan: 'I want to practice putting a condom on a real cock.'

Oh. Oh. Oh! She wants to hold my cock and put a condom on it? Yes. Oh yes! I nodded dumbly and moved my hands as if to undo my shorts. Jenny nodded at me to go ahead and reached up to her top button. I did the same.

Jenny held my gaze and unbuttoned her dress before stepping out of it to stand revealed in her bra and my underpants. As I have said, her tits were small and she barely needed a bra.

I mean, there were several girls at school who didn't wear one sometimes. They didn't go around with their breasts visible between bulging buttons or anything but sometimes in a warm class they would pull off their woollen jersey and if you had a lucky desk you could look diagonally forward and stare at their tits for the rest of the lesson.

Jenny's tits were not big. Quite the opposite. They were small and firm. The cups of her bra were just a shiny fabric. Look, I know what underwire is, that is where there is an arc of flat metal making up the bottom edge that sits under the breast and touches the chest. Well Jenny's bra was no-wire. The cups were just satin looking fabric. The bra matched the panties of hers that I was wearing - pale blue with a lace trim. She wriggled the bra so the clasp was at the front and undid it, dropping it to the floor.

Then, holding eye contact, my sister reached up and tweaked her nipples. She plucked them, stretching them forwards and then rolling the nipple between her thumb and finger and seeming to pinch quite hard.

Jenny asked me, 'Have you ever done it before? Putting on a condom I mean.'

Well, now she came to mention it, no, no I had not. She surely knew that. And nobody I knew had said they'd done it. For one thing, if you admitted to friends that you had practiced putting a condom you were admitting that you had handled your erect cock. Even then I could see it was absurd for teenage boys to pretend they didn't handle their erect cocks several times a day. But still, the mind-set was pervasive and it seemed to have left to a gaping hole in my education that it seemed my beautiful sister was about to fill.

I admitted that I had never put a condom on for real. I also said that I didn't want to give our parents the idea that I was using them. We both knew that, despite all their promises that they would keep an eagle eye on the supply of condoms on the hall table.

'No problem' and Jenny turned away saying 'I got something from Leanne that might help us.' She went over to her cupboard and pulled out a plastic bin that had her school books in it. Good hiding place, I had certainly never looked there. With a flourish Jenny showed me strip of 3 Durex condoms packed in foil.

'Where did you get those?'

'I stole them from sex-ed ages ago.'

I looked down at the condoms. We had both had lessons in how to open the pack. The teachers even used an old joke about if stopping to put on a condom spoiled the moment then you were doing it wrong because it should last more than a moment.

I don't know how it is today but back then all the sex-ed was focussed on getting the girl to coax the guy to wear a condom. There were slogans like "No glove, no love" and others slogans too lame to have stuck in my mind. I mean it was kind of odd; we all knew that AIDS was the big fear and the reason schools had started teaching about condom usage. But it was also widely believed that AIDS was almost exclusively a male homosexual disease.

Well, actually, back at the start, it mostly was. I think what scared the politicians into action about sex-ed was the growing awareness that AIDS could affect heterosexuals too. And the wise safe-sex campaigners got the politicians onside by talking about prevention of disease and pregnancy. Nothing like teen pregnancy to get old white male politicians worked up.

When the sex-ed classes had been starting up in our state any number of religious bigots had shouted doom that it would only give the kids ideas and encourage them to experiment. Well maybe me and my sister Jenny are a bad example, but I think the most common response was the 'ooh yuk, too much information. I am never going to do that.'

I knew it wouldn't happen. But if, oh please let it happen, if I fucked my sister Jenny then I need not worry about getting her pregnant. Every year a half dozen or so girls left the school because they were pregnant. For some reason the fathers - in the small number of cases when it was leaked out so widely that even I heard about it - were usually boys in the Rugby League team from a nearby boys' school. What was wrong with the boys at our school I wondered?

Anyhow, I knew that if I wanted to have any chance of getting my cock any nearer to Jenny's cunt I had better be wearing a condom. Leanne had also given Jenny the wee leaflet that came in the pack and she studied it carefully. I spotted an opportunity and walked around to stand looking over her shoulder. Of course this meant my cock made contact with her leg.

She glanced down for a moment and then looked back at the leaflet. She looked between the two several more times as if trying to see how the simple line drawing in the leaflet related to the real life cock glistening with precum. We'd been told all about precum and how it was still packed with sperm.

But still Jenny didn't seem too fazed as I was standing there naked from the waist down, erection waving, while she tore the pack open and removed the condom. She looked at it seriously as we had been told to do to check for rips and then she checked which way round it was before she delicately squeezed the teat. So far it was just as we had all had to do in our classes at school.

The difference, as I was watching mesmerised, was that this time a girl, my own sister, was about to hold my cock and put on a condom. Not put the condom on the end of a broom stick but put it on my cock.