Um, Both, I Guess Ch. 05

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.

Overview of this chapter:

In this chapter Jenny gets us to swap underpants and meet up during lunchtime at school to show and tell. When we get home she asks me to wank for her and gives me a female anatomy lesson.

'Yes. Jenny, it's you. Oh Jenny I think about you. I love you. You are my sister. You are beautiful Jenny. Really. I mean it. I love you. I love you like a big brother and I want to look after you and protect you. I really respect you. You are smart and I know you'll be a big success one day. And you are also so beautiful that I just can't help it, but I really, really, really, you know -- like -- you. I so want to be closer to you. Really close -- umm you know'. I paused then added 'Everything about you turns me on' (Jenny was a big Police fan and I thought it wouldn't hurt to say that).

'OK. OK. I get the message. Thanks Ian. You are my brother and I love you too.'

The way she said 'love' made me look carefully at her face (for a change!). I mean English really makes the word love work hard. I had a hunch -- or desperate wish - that my sister didn't mean it sarcastically or '2. Familial affection' and instead meant '4. 'Sexual desire'. (Try as they might school dictionaries still contained a few 'rude' words').

For some inexplicable reason (probably because I was stupid) I asked a dumb question.

'Hey, you found the Y pretty easily. Have you worn my undies before?'

A momentary blush passed across my sister's smooth white tits. She gave her thighs an extra big squeeze and slipped her fingers into the Y again.

'Yes little', she looked at my crotch and smiles, 'yes actually-quite-big-brother; I have worn your undies before. Why? I think for the same reason you wear mine. I like the thrill of it being so naughty.'

I was shivering with nervousness but I just had to ask.

'What do you think about?'

Jenny paused. Really paused. For a moment she stopped rubbing and slowly pulled her fingers out. She looked at her fingers, looked at my cock

'Well, my thoughts are sometimes about watching boys when they don't see me or think I'm another boy. I umm, well, I think it would be cool to watch two boys play with each other. You know, show each other their dicks and stuff.'

I so wanted to hear more of Jenny's naughty thoughts. Like most boys of my age I had fooled around with male friends. The idea of Jenny watching me do that was all it took -- I came in several shuddering spurts.

Jenny was startled and I was embarrassed. I tried to apologise but she just said I should maybe go and get cleaned up. I left her room cursing my quick trigger and did as she had suggested. When I came out of my room I noticed she had shut the door to her room. I tried listening outside but she called out, 'Ian -- ok I admit it! I'm wanking! Now leave me in peace for a few minutes. Maybe next time you can watch.'

With that on offer -- even though I knew it wasn't true - I couldn't very well disobey so I sat nervously in the lounge and soon Jenny emerged and behaved as if nothing had happened. I was too confused and scared to mention it so the rest of the evening went like a normal Friday.

But I resolved to tell Jenny about my experiences with other boys the next time we were 'playing'.

After that tumultuous Friday, the weekend and the start of the next week were uneventful, though I was very nervous and started every time my sister Jenny came into a room. Mum and even Dad picked up on it and wanted to know what the problem was. We both insisted there was no problem.

But I was worried she had said something to Mum because, against all odds, Dad chose this week to give me a talk about sex. He was reassuring and honest, just too late as I'd heard it all from friends and seen it all in porn mags -- usually Dad's. I was reassuring in turn and had to admit that there was no prospect of anything.

Dad was then uncharacteristically embarrassed and told me that masturbation was perfectly normal and harmless. I said I knew that. Then Dad mentioned in the most gentle way that some teenage boys used a handkerchief to ejaculate into instead of staining the sheets. Ooops. It had never occurred to me. Sure, when I stripped the sheets off my bed they were spotted with cum stains but I had never thought anything of it.

In one of our rare conversations when we had no chance of being overheard, I mentioned Dad's talk. Jenny said she'd just had the birds and bees talk from Mum as well. Uh oh. Did they know or suspect? The next day Mum and Dad called us together to explain a new house rule. We quickly looked at each other. Had we been found out?

No, it seemed not. Mum and Dad announced they were placing a bowl of condoms on the hall table. We were free to take as many as we wished -- we could even give them to friends whose parents were 'strict', but we should make sure the friends kept quiet about the source.

Yes, yes, they explained, they knew this was years and years too early and they knew we really didn't need them. But, this was like the wine with dinners. I need to explain, that the Greek heritage meant that our parents regarded alcohol as normal and they just didn't understand the 'Anglo Saxon booze culture'.

For this reason we'd been used to the occasional small glass of wine with dinner. Mum and Dad's theory was that this would demystify alcohol and teach us control. It seems to have worked and now, many years later, I can honestly say I have almost never been drunk and I can take or leave booze. So, they explained, they wanted to make sure we gained the same skills towards safe sex.

I want to pause a moment and remind readers that this was a staggeringly liberal view for the time. Australia was a very uptight society then and condoms had only begun to be talked about in the wake of the AIDS crisis.

Anyhow, Dad said the bowl would be refilled once a month, no questions asked, no counting how many were used or anything like that. He stressed there was no pressure to have sex but if we did we had to use a condom. This was at the height of when AIDS was recognized as an 'anyone' disease. We had lessons in school about condom use. Excruciatingly embarrassing lessons where we fitted condoms to featureless wooden sections of broom handle.

Dad suggested that to save embarrassment we should each take a few out each month. We could stockpile them or throw them out. We both protested we had no need for them and they said it didn't matter -- maybe we knew some friends who would need them. I stole a glance in case Jenny's face suggested she did. Nope. Nothing. Yuck. How embarrassing to have your parents talk like that. I was mortified. How much did they know or suspect?

As the week wore on I hadn't had the nerve to discuss it with Jenny, but I assumed and hoped that Friday would bring another 'session'. Then it was Friday and we hadn't arranged anything. On Friday morning I was getting up and was just about to put on my school uniform when my sister Jenny quietly slipped in through my half open bedroom door.

We were both wearing the long t-shirts that passed as pyjamas in our house. Most times I didn't wear anything else but since it was getting a little colder I had worn my underpants to bed and I knew that Jenny usually wore panties. Jenny held up a finger to her lips to hush me and pushed the door almost closed. I stood still -- instantly erect. She whispered 'Are you wearing undies?'

I didn't make the connection and she had to repeat it before I nodded and pointed to a rapidly growing erection that was poking up under the t-shirt -- even though I had really only just finished my regular 'wake up wank'. Did you do this at that age? Every morning I would lie in that halfway between awake and asleep and wank. Then I'd lay blissed out for a few minutes in the afterglow before finally getting out of bed.

Jenny gave a little wave with one hand that I realised meant she wanted me to lift up my t-shirt. I did. She stared at my erection and blew me a kiss then, in return, Jenny lifted up her t-shirt to her waist. She was wearing the red panties she had made me wear a month ago. That was cool. She dropped the t-shirt and reached under with both hands to pull her panties down. As she stepped out of her panties -- that had been on her all yesterday and all night - she motioned for me to remove my undies.

I did so -- almost falling over in my rush - and Jenny held out her hand with her panties. I looked dumbly at them. My sister pushed her panties into my free hand and reached over and took my underpants from my other hand.

Then she stepped into my underpants and pulled them up. Then Jenny pulled up her t-shirt up show me her wearing my underpants. Once again it was just such a turn on to see the Y-fronts with no bulge filling them out. It was even more of a turn on to next see that Jenny then slipped her fingers into the Y, like she had done a month ago.

My sister is one of a kind. I have never heard before of a girl who got off on wearing her brother's underpants to wank in. I couldn't see of course but she had obviously just dipped her fingers into her cunt. She must have been moist already because she pulled her fingers out a few seconds later and I could see they were coated in something wet and sticky.

Jenny knelt in front of me and for one insane second I thought I was going to get a blow job from my sister. I just as quickly remembered that Jenny was the boss and it wasn't likely to happen. Instead she pulled her warm panties from my hand and tapped my left leg. I lifted it and stepped into the leg hole. She repeated with the other leg and then she pulled up her panties over my knees and to my groin.

Picture this: My sister is sexually aroused and has come into my room. I haven't seen her cunt but I have just watched her take off her panties and then put on my underpants. Now she is helping me put on her warm panties from overnight.

She pulled the panties up but my cock was sticking straight up toward my belly and poked over the waistband. Jenny stood up and patted my cock through her panties. Then Jenny took my hand and formed my fingers into a fist. I knew what this meant and I gently pushed her with the fist.

She whispered melodramatically 'Oh you hit me. You have to be my slave. I want you to show me what you are wearing at lunchtime'.

'I will. I will do anything you want.'

'I know,' and with a last but (I hoped) lingering glance at my cock, she slipped out of my room. I finished dressing and went for breakfast.

It wasn't unusual for me to have an erection at breakfast nor was it unusual for me to be wearing my sister's panties at breakfast. But it was unusual for my sister to be sitting across the table from me and know both these facts.

I zoned out for a minute imagining that she had told all her sexy friends and that they were going to be there as well. I hoped they'd flash their cunts at me then demand I show them the panties I as wearing and...

'Hello! Earth to Ian!'

'Huh? Sorry, I was thinking.'

I noticed that both parents were out of the room.

'I bet you were. Listen. I just said at lunch time we should meet outside the labs - alone'. (This was a seldom used corner of the school yard).

'Sure. OK.'

And so we set off for school. Me wearing my sister's panties at her order, and my sister wearing my underpants because it seemed to turn her on.

We parted at the gate and reconfirmed the lunch time meeting. I can't really describe how it felt to see my sister walk away and know she was wearing my underpants and to know she knew I was wearing her panties. I didn't concentrate too well in class and it was an age before lunch time came. I told my friends I had to talk to Jenny and that I'd catch up and play as soon as I could.

In Australian schools at the time, you ate your lunch -- that you bought from home - in your class and then, after a bell rang, you were free to wander the school and playing fields for 45 minutes. Our school, like many built in the late 70s, consisted of several free standing squares of single story classes that surrounded a small courtyard. Each courtyard had some concrete planter boxes that divided the area into several bays of seating. The courtyards by the labs were furthest from the playing fields and were less crowded.

I found a corner and sat down on the bench, waiting for Jenny. She arrived a minute or so later, slightly puffed from having run. She sat down beside me. There weren't many other kids around but a boy and girl sitting closely always sparked interest and discreet spying. However, it was well known we were brother and sister so the few other kids in the other bays paid no attention.

Jenny began, 'How was your morning?'

'Sore.'

Jenny was instantly concerned 'Oh! What's wrong? Did you hurt yourself?'

'Nothing like that', I leaned over, 'I have been solid almost all morning and it is starting to ache.'

Jenny giggled with relief, 'Well,' she lowered her voice, 'I have been practically dripping wet all morning.'

Dripping wet? My sister was starting to talk like a letter in a porn magazine. I was hazy on the details over what this meant. I was about to murmur something urbane to show I understood what she meant. Then I remembered I wanted her to teach me things about her body. So I shook my head in puzzlement.

'I don't really know what you mean. I mean I sort of do but only umm from umm the letters in umm Dad's magazines.'

Jenny was clearly aware of my ignorance but thankfully willing to educate me.

'Well, when a girl is umm, well when a girl is aroused', she blushed, 'well, then her umm her vagina lets out some liquid to umm lubricate it.' Jenny stopped and looked me in the eye. 'What about you Ian? You are also aroused' She looked down for the all too plain confirmation bulging in my pants.

'What are you going to do about it?'

'Well, what I want to do is go to a toilet stall and jerk off but I guess I'll wait for after school.'

'Sounds good to me. I agree with both ideas -- I'd like to rub myself off but I'll wait'.

Wow. My sister was casually discussing being aroused -- by me her brother -- and discussing how she wanted to masturbate. She continued, 'So, are you going to show me or not?'

I was surprised. I hadn't really thought she wanted to see, I had thought just knowing I was wearing her panties would be enough.

'Umm sure.'

I looked around carefully and took off my jersey, bunched it up, and placed it on my knee on the side away from Jenny to make a low barrier in case someone wandered by. Then I undid the button and zip of my shorts. I spread the opening and showed Jenny my erection bulging in her panties. She also glanced round and raised her fingers to her lips and kissed them. Then she touched her fingers to the fabric over the head of my cock. I watched in an agony of wanting to jerk off.

'You sure like wearing my panties don't you? OK, do you want to see me now?'

I nodded while sitting back up.

'Sit down there', she said indicating the ground. I sat with my face now at her waist level. Jenny opened her knees wide and inched the hem of her dress up her thigh a little. I could see my grey flannel Y-fronts had a wet patch at the front!

'I know nobody would notice even if they did see up my skirt, but it still feels really sexy. I have been stealing looks at the boys' crotches all morning, wondering if any of them are wearing panties and trying to guess if any of the girls are wearing boys' undies.'

As she said this I was staring up her dress as she slowly rocked a little forward and back on her bum. It wasn't thrusting but she was clearly enjoying the sensation and I could swear the damp patch was getting darker.

Then some noise startled Jenny and she snapped her knees together and I pretended to be picking something up. We'd done it! It wasn't as far as we had gone at home but we had done it at school and that seemed to make it so much more exciting. We held hands for a moment and then both realised that we shouldn't be seen to do that either. Other people entered the courtyard and we chatted earnestly about mundane matters.

As soon as we could do so without looking like we'd been caught out we parted and went to join our friends for our usual lunchtime activities. But my mind was definitely not on school that afternoon. All I could think of was getting home to play with my sister.

We were alone in the house and we had about 3 hours before our parents got home. After sitting at the table for an after school snack, Jenny asked 'Do you still want to play?'

I opened my mouth to reply and then saw the smile -- she knew how much I wanted to play.

'OK, I was joking Ian, I'll be ready in a minute.'

A minute or so later I heard her sing out: 'Oh, big brother!'

When she called me 'big brother' it made me weak at the knees and hard in the cock. I scampered to her room. Jenny lay on her back on her bed wearing a t-shirt without a bra. Her nipples protruded. The t-shirt came to just above her navel and the sheets covered her groin but she was plainly gently thrusting her hips and clenching her thighs. Her school uniform, bra and panties were crumpled on the floor. That could only mean she was naked below the waist. Jenny nodded at her panties.

'Put them on -- I'll turn away while you get changed.' my sister told me.

That didn't make a lot of sense to turn away but I wasn't going to argue. I was out of my clothes in a flash - with my cock sticking straight out. The panties were easy enough. The bra always gave me a little trouble when I'd put it on alone. Then I was standing there in her panties and bra.

'Do you want me to put the socks and dress on too?' I asked.

'Would you like to?'

'Yes please.'

'OK then, put the socks and dress on. And then play for me.'

And I didn't need to ask for clarification about what 'play' meant. I slipped into the dress and sat on her bed next to her feet while I pulled the socks on. Her knees were rocking apart and together as she did whatever she was doing under the bed covers.

'I'm ready.' I told her and stood up and smoothed the dress over my chest and thighs. My erection was obvious.

'Go on then' she told me.

I lifted her dress with one hand and flopped my cock over the waistband of her panties with my other hand. I jerked away in that frantic way teenage boys have. But, as much as I wanted to cum, I also wanted this to last. I certainly wanted more than just jerking off in front of my sister again.

Wow, 'again'! I'd already done this before which made me pretty lucky, I knew. But I still wanted more. I wasn't informed enough to know in detail what I wanted but I still longed for, well, something else. It must have been obvious that I was a hairs' breadth away from coming because Jenny hissed 'Don't cum. Not yet.'

So I had to let go of my cock to stop it happening. I stood breathing heavily.

Then as if we had been talking about the weather my sister Jenny said 'Do you want to see my vagina?'

It turned me on to hear her use such 'official' words.

I said I really did. Jenny laughed and said I couldn't.

I must have looked like I was going to cry because she said that the first lesson was that I couldn't see her vagina -- because that was way inside her. She explained that the bit I wanted to see was called her vulva. 'Vulva', I repeated to myself. Already my Anne Frank fantasy was coming true -- my sister was teaching me about her body.