Um Both I Guess

So far:

I fancy my slightly older sister, Jenny. I wear her panties and I have seen her cunt.

Overview of this chapter:

I wank in Jenny's panties. The attraction between us seems mutual. My sister and I play a game where we wear each other's clothes.

(From Ch 01)...It is only in retrospect that I see that right from the very start Jenny had been encouraging a sexual tinge to our games. For example, because Jenny was a bit of a slob she would get me to clean up in her room for her. All ok so far, but at some stage she got me to pick up her clothes. After a few sessions I realised she was deliberately leaving her panties and bra on the floor for me to pick up.

What I mean is that, having snooped in her room before, I would know that the panties now on the floor had been in totally different places - usually beside her bed on the opposite side of the room to the laundry bin. But now here were two or three pairs of panties and a bra lying on the floor next to the laundry bin as if she'd just missed throwing them in.

The first time I was going to ignore them but she told me that picking up all her clothes meant picking up all her clothes. So I gingerly picked up a discarded pair of panties as she watched. I wasn't dumb enough to give any hint I was intimately familiar with her panties but much later she told me she had worked out what I was doing and that had inspired her to nudge our sessions of playing The Game in the direction of crossdressing. Anyhow, at first it was easy to quickly flick her panties into the basket but then they started getting further away and I had to carry them across the room under Jenny's bright gaze.

As much as I tried to hide it, I worried that it was obvious how much I enjoyed touching her panties. I need to explain that it was not panties as such that excited me. Sure, then (and now) I like slipping some tight worn panties on. The turn on though was the fact that the panties have been next to my sister's cunt and I believed that her panties were as close as I'd get to her cunt. However, as you will read, to my everlasting joy, I was eventually proved wrong about that.

It sounds silly to say so, but at the time I hardly noticed that when it was her turn to do my chores that there was anything odd when she said 'How about I clean your room like you do for me?' I mean she hated cleaning so why would she offer? Well, I didn't notice anything odd so I agreed.

Most of my clothes were in the basket so Jenny said she'd take the dirty ones to the main laundry basket and fold the others. I swear I didn't notice anything too weird but she took each item out and sniffed it - including my undies. I was a little worried in case there was a smell of semen on them - for example if I'd had a quick wank during lunchtime at school - but she didn't seem unduly bothered and folded some items and took the pile of dirty clothes away with her.

Over the next few weeks we did this several times. Neither of us seeming to find the other's interest in our underpants odd. After another month or so of minor forfeits - usually silly poses and 'telling secrets' - we had THE session that changed everything. I make it sound easy but I worked hard to get the swapping clothes thing into The Game. (Only to find out later that Jenny had worked hard to get me to do exactly this).

I don't want to mislead anyone - it took weeks and weeks for us to get to this point. And as I mentioned in the introduction this isn't one of those stories where the sister said 'Hi, big brother want to fuck me?' in the first paragraph, and by the second paragraph their parents and the dog have joined in. I have skipped over many tedious months to get to the point when things changed. This is how they changed...

I have never come across another chick turned on by crossdressing herself before. I know heaps of guys get off on wearing panties and I know some girls get off on the power of making a guy wear her panties. But I have never yet heard of another straight girl who was turned on by wearing boy's clothes - and her brother's at that. I don't pretend to understand it and I'm just telling you what happened.

I was being the slave and making a snack for us both and Jenny said 'You make a great maid Ian, all that's missing is the little dress.' I blushed and became erect. My sister must have noticed because she paused and flicked her eyes at my crotch.

'You'd look good in a dress big brother.'

More blushing. Hell yes, I did look good in a dress and I would love for her to see me wear her dress.

Another pause from Jenny.

'Yes, you would look good in a dress. How do you think I'd look dressed like a boy?'

I was speechless and opened and closed my mouth, trying to say something. Inspiration struck,

'I think my big sister would look really cool as my big brother.'

That must have been the answer she was looking for because over the next few minutes Jenny had put forward a set of 'rules' about doing exactly this, and I was happy to go along with them.

We were to go into our bedrooms and take off our clothes - except our underpants. I was the first to throw my clothes into the hallway then I had to go back in my room and close the door. Jenny opened her door, took my clothes and left hers and went into her room to put on my clothes.

There, uncharacteristically folded in a neat pile, was her uniform with the socks on top. And her clothes were still warm and smelled of her. I described Jenny's school uniform in Chapter 1 but, briefly, the girl's summer uniform was a dress-like thing that buttoned down the front to the waist and flared into a pleated skirt. The girls' uniform included knee length white socks with a frilly bit at the top. The boys' uniform was grey cotton shorts, a dark grey shirt and knee length grey socks with a couple of coloured bands at the top - like Angus Young in ACDC.

I retrieved her clothes and took them into my room. I pulled on the lacy socks and stepped into the school dress and raised it to my hips, rubbed my nipples and finally buttoned the dress up.

Jenny called out and said she was ready so we opened our doors and looked at each other. Jenny stood legs apart and hands on hips with her tits thrust forward. The shirt stretched over her tits and I could see bare flesh between the buttons and her nipples pressed hard against the fabric - she had taken off her bra! She had pulled the shorts tight. In all honesty it wasn't especially revealing or anything like that. The sexy thing was that I knew it was a boy's uniform - and not just any boy's but my uniform.

Jenny told me I looked beautiful and just like she had imagined a sister would have looked like. I believed her at the time but thinking on it now, so many years later, I know that a gawky boy - all skin and bone and sharp angles - does not look like a beautiful girl.

'Do you think I would pass as a boy if I wore this to school one day?' Jenny asked, 'I mean another school where they don't know my face. Hmm maybe I could go to [she named a boys only school].'

'Umm not with umm not with umm...'

My eyes were riveted to her breasts, swelling my shirt front. Jenny followed my gaze and laughed.

'Oh no, watch this' and she stopped thrusting her chest out and her breasts seemed to vanish, 'I bet with a baggy jersey on, no one would guess I was a girl'.

I was still slow on the uptake, 'But why would you want to?'

'Oh you know, just to see what boys are really like when they aren't trying to impress a girl and I dunno, follow them round and see everything they do and stuff.'

I caught some slight hesitation and emphasis on the 'everything' she said. I wondered if she shared my very particular obsession as to what 'everything' meant. I filed the question for later.

All this time my erection had been making a huge bulge under Jenny's dress and she had not looked at it in any way. Now she was staring which only seemed to make it harder if that was possible. I desperately wanted to whip my cock out and jerk off but I knew Jenny was in charge and I knew it wouldn't be right.

I sort of worked out that Jenny wanted this to continue but also wanted to ignore my erection.

Neither of us knew what to do next. As much as we both clearly wanted to take things further, we were both a bit overwhelmed by what we had already done.

Jenny seemed especially interested in trying to pass as a boy and hearing about what boys were like when there were no girls around. I wasn't sure what she wanted to know so she explained; 'Do boys talk about girls a lot? Do they umm you know umm see who is the biggest and stuff like that?'

I couldn't say there was any single thing that let me know but it was obvious even to a complete newbie like me that my sister Jenny was aroused at hearing about me seeing naked boys. That is, it wasn't hearing about naked boys but the idea of boys looking at each other.

This made perfect sense, as I every boy I knew was obsessed with the idea of lesbians, so why shouldn't girls think about boys? I wasn't quite ready to share how I had wanked with another boy - much less tell her it had been while we both were wearing unwashed pairs of Jenny's panties - so instead I generalised.

'The guys don't talk about girls too much. Probably because hardly anyone has ever been with a girl. Some guys talk a lot and tell stories about what they have done but everybody knows they are lying. Guys never look at each other's dicks. You just don't.'

'What about when you are changing for sports or standing up to pee?'

'Not even then', I paused and decided Jenny wanted details and honesty, 'well, I'm pretty sure everybody looks but you make sure nobody sees you doing it and you just don't talk about it.'

Jenny seemed keen to pursue this line of questioning.

'But you do look sometimes?' There was an eager tone to her voice but I didn't know what to say to keep her interested.

'Oh yeah, everybody does.'

I was desperate to jerk off and I realise now Jenny must have been the same. So I was relieved when my sister seemed to come to some decision and say that we should maybe think about getting changed into our own after school clothes and then going to get our dinner.

As Jenny closed her door she said she had a few things to do and she'd be out in a minute. That was just great with me because it mean I could wear her dress in my room while I wanked. I was so worked up that it took only seconds - even by my teenage wanking machine standards. I was careful to cum into a rag and wiped myself clean. Then I took off her dress and put on my own after school clothes.

As we met again in the hallway I saw that Jenny's face was flushed - as I knew mine must have also been. As Jenny handed my uniform back she cast a lingering gaze at where my erection had been. Its absence must have been telling.

'Hey Ian, what do you think if maybe next time we umm swap all our clothes?'

ALL our clothes?! That could only mean she wanted me to wear her underpants and she wanted to wear mine. What did I think? My sister wanted to know if I wanted to wear her panties with her permission while she wore my underpants? OK. Play it cool. Don't be too obvious.

'Oh yes please Jenny. If you mean what I think, then I would love to wear your undies and we could show each other. How about next Friday?'

Right. Like I said. Calm and dignified. Not.

'Yeah, OK. Next Friday would be great. But now we need to get some food.'

And with that Jenny seemed to switch off the sexual element. My sister had just said she wanted to wear my underpants and wanted me to wear hers - and now she wanted to talk about which place to get takeaways from? Can girls really do that? Be all steamy one second and all sensible the next?

The rest of the evening was uneventful. We got dinner, did homework, and watched TV before Mum and Dad came home. I knew it would be an extra good wanking session in bed because her comment about 'everything' had primed me for a favourite fantasy, but I'll talk about that later.

The weekend passed without further incident and I spent the next week with an almost permanent erection. I couldn't get the previous Friday off my mind, or the coming Friday for that matter. Friday was going to be a special day: The folk music club was having a special dinner and recital - Dad played a mandolin and Mum accompanied him on a tabor and sang. They weren't too bad and even wrote some songs themselves.

Anyhow, this sort of thing didn't happen very often and this would be only the second time we hadn't had a babysitter now we were getting older. We had known about this event for weeks and weeks and had been promising our best behaviour. In fact Jenny later told me that she had stepped up the clothes swapping in preparation for this night alone.

I was pretty confused and nervous that Jenny would tell our parents or one of her friends and, even though I was hornier than ever, I still felt that any sort of sexual activity with my sister was wrong. I felt worse that I enjoyed it all the more because it was wrong. I am sure Jenny felt the same.

On Monday, Jenny broached the topic on our walk home from school. Usually we walked in ever changing little groups with friends who lived nearby but on this day it was just me and Jenny. I think the school show was being planned and a lot of our friends were rehearsing. I wasn't involved because I couldn't sing or dance, and Jenny was too busy with her dancing outside of school to be in the show.

Anyhow after some mundane chatter Jenny said without any preamble, 'Ian, you know what we have been doing is wrong?'

I looked at her. Yes, I knew it was wrong. But it was so enjoyable that I wasn't going to let it being 'wrong' stop me. But I knew I had to tread carefully.

An upside to having atheist hippy parents was that they were socially liberal. Some parts of Australia are liberal. Some parts are not. We lived in a liberal part and there were a couple of openly gay local politicians (remember this was in the 1980s). We had recently gone on a march to support them when some churchie bigots mounted a smear campaign. The smears had failed and they had been re-elected. Jenny and I had both been inoculated with an array of counter arguments to the 'it's wrong' brigade. The first of which was to ask 'who says it's wrong?'

'Well,' I began, 'yes, some people probably think so. But it doesn't feel wrong when we do it. In fact it feels really good. And we are both consenting. I mean, who says it's wrong?'

I was proud of that and had planned this line of argument. The argument about decriminalising gay sex was in the context of consenting adults. We weren't exactly adults - we couldn't go to a pub etc. - though like all high school seniors - we certainly liked to think of ourselves as able to make adult decisions. However, we were over the age for sexual consent, so if Jenny called me on this she would be admitting that we were just kids, and I just knew she felt more adult than I did.

Jenny didn't say anything and I got the impression that, even though she had been leading and making the decisions about all our sexual interactions so far, she was wanting me to convince her that it was OK. I also hoped that she wouldn't take much convincing.

I warmed to my task. 'I mean we are not hurting anyone. What two consenting adults do is their business and nobody else has any right to get involved.'

OK, we were not adults, and resented adults telling us what to do. But we certainly were consenting. Oh, I hoped my sister knew that there was nothing I would not consent to with her.