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.

Overview of this chapter:

In this chapter my sister watches as I put on a full-on crossdressing show for her while she fingers herself underneath a blanket. Now Jenny wants to play with my cock. We tell each other our fantasies. Hers is hot and makes me cum in front of her.

In a box in the cupboard are some old clothes of Jenny's. My favourites are a set of old two-piece nightclothes. Really flimsy, very fine see-through nylon gauze mesh stuff [apparently it is properly called tulle or gauze], with lace trim and small embroidered flower bows at the top of the waist band and the centre of the neck line.

The top has a scoop neck and short sleeves. All edges are trimmed with lace. The bottoms are basically baggy panties (baggy even on a teenage boy) and in a style that today they call 'boy shorts' - sort of like a 1940s swimsuit bottom. There are two sets, blue and yellow. My favourites are the yellow because it is Jenny's favourite colour and I imagine she was worn them more often next to her cunt.

If any shop tried to sell them today they would be accused of all sorts of dodgy things. They leave nothing to the imagination. As I took the yellow ones out of the cupboard Jenny's eyes went wide and she giggled. She said she remembered the day Mum had decided they were too revealing and had taken her shopping to get the long t-shirts.

'You know, Mum said you were getting to a difficult age and it was better if I dressed a little more modestly. We had a big long chat about boys and how to behave. Mum kept going on about how important it was 'not to lead a boy on'. She said that boys got excitable and it was up to the girl to make sure things didn't go too far. Then she explained what was safe.'

'Safe? What does that mean? '

'Oh you know! Safe sex, ess ee ecks - sex! Basically anything that doesn't give you a disease or get a girl pregnant', she giggled, ' um, you do know how that happens don't you?'

I knew better than to take offense and smiled as I said in a mock sad tone

'I know the basics but none of the detail.'

Jenny raised an eyebrow that meant 'well?'

'Well, mostly I know. A guy puts his thing, his penis inside a girl and cums.'

'OK, OK. Just checking you knew. I still wear these sometimes in bed. I umm, well like the feel of them.'

Oh of course that explained why they still smelt of her. Fool. I should have realised.

'Oh. Do you?' I managed in reply.

'Yeah. I put them on sometimes when umm sometimes...'

Ha! I was sure Jenny meant that she sometimes had them on when she wanked. She trailed off, a little embarrassed and returned her stare to my erection. Her fingers were moving faster.

I took off her panties - my erection waving wildly - and pulled the night clothes on. Their allure was tripled now I knew she wore them to wank in. The top comes to mid belly and the bottom sits comfortably on my hips. Because the fabric is so transparent I like to tuck my penis between my legs and stand there watching in the mirror as I slowly clench my penis with my thighs. I do this because I can pretend I am a girl.

Jenny seemed to like what she saw.

'Wow, it looks good when you do that. You make a pretty girl. I wish sometimes I did have a sister. So umm do you umm you know touch yourself often?'

My sister Jenny had just asked me if I ever 'touched myself' while she is rubbing herself and watching me wear her flimsy night clothes while I have a huge erection. I couldn't help it - I laughed.

'You mean wank? Sure, all the time - sometimes I wank 3 or 4 times a day.'

'Wow. That's a lot. Do all boys wank that much?'

I still don't know if teenage girls tell each other this sort of thing but I know teenage boys definitely do not so I was hesitant.

'Umm yeah. I think so.'

My sister continued asking questions about my wanking habits. 'And do you ... you know... do you... umm... cum each time?

I was on much firmer ground here and I was almost boastful as I said 'Oh yeah, and I can do it again a few minutes later. Hey Jenny, umm, do you umm touch yourself - hey do girls call it wanking too?

'Yes. Yes'

'huh?'

'Yes, I touch myself most nights and yes we call it wanking'

'Oh. Do you cum too?'

'It is different for girls but yes, most times I do.'

I was fascinated. I had only the faintest idea about female masturbation and knew of it only from letters in our dad's porn mags. I wanted to take the initiative so I asked, 'Do you mean you juices pour out?' Wow. What a dweeb I must have seemed like. Luckily Jenny didn't take offence or laugh at my ignorance - she was learning here as well.

Jenny said it was sort of like that but also a sort of clenching that you couldn't control. This was more like it!

Jenny paused and clearly had something else to ask me.

'Ian, what exactly is boy cum like?'

Ha! Had she ever asked the right guy! I felt I was shooting a cupful a day.

'Do you want to watch me make some?' I blurted (so to speak).

Jenny tried to seem uninterested but wasn't fooling anyone.

'Maybe. Is it true that it hurts if you don't finish?'

I had no idea what she meant and asked what she meant about finishing. She told me that some of the girls at school had been told to be careful about touching boys' 'things' because it hurt the boy if he wasn't allowed to cum. I laughed and told Jenny that it wasn't true and that I could do all sorts of things to my penis and it didn't hurt if I didn't cum. I saw instantly by the glint in her eyes that she was very interested.

'Like what?'

'Well I can show you if you want...'

'No, not now, just tell me.'

'OK, I can bend it, twist it, treat it like a piece of rubber and it feels good and doesn't hurt'.

I really had not been expecting things to go any further than wearing her panties, but my sister Jenny reached out her hand and pushed my cock down through her panties. Then she let go and watched it bounce back up. She did this a few times - up and down like a see-saw. I couldn't believe how much better her light, casual, touch felt than my own solid, purposeful, grip.

I must have been in a trance because she poked me in the chest:

'Hey, wake up! Can I pull them down and have a look?'

As if I was going to say no! So I lifted my hands away from my sides. Jenny came close and put her hands on my hips and rolled the panties down. I was sure the heat of her thumbs as the rolled the panties down my thighs was going to leave welts. My cock bounced free. I stood with her panties around my knees.

I took my cock in one hand and offered it to Jenny to touch. She pushed it down again and let it bounce up. Then she took my cock and rolled it between her hands, pushed it, pulled it and generally investigated it. I was so close to coming. I had to pull away a little and explain that if she kept doing that I would cum all over her hand.

So my Jenny turned her attention to my scrotum. She rolled the wrinkly skin between the thumbs and forefingers of both hands - like a cartoon villain twiddling a moustache. Then she took a small section and stretched the skin flat and let go - staring at the way it wrinkled again. She gently cupped my balls in her palms like she was weighing them. She let the drop and repeated that a few times.

'Hey', she said, they are unbalanced.

I hadn't paid much attention before but she was right. Just as my cock had a slight bend, my balls were not level. That was embarrassing. I'd played with them millions of times and it hadn't registered, Jenny notices the first time she touches them.

She asked all sorts of questions about my cock. She was especially interested to hear what made it go hard. I told her that whenever I thought about girls it went hard. She wanted to know which girls I thought about and what I thought about. I was evasive. I mentioned a few of the girls in my class who I sometimes thought about when wanking but Jenny could tell I was keeping something back.

She persisted. To divert her I told her it was my turn to make her do something and then I would tell her. I told Jenny I wanted to see her naked and then wear my underpants. This was obviously a cheat because it was two things but she didn't seem to notice. She seemed reluctant and probably knew that she didn't have to because I would do anything for her. But she turned her back to me and quickly pulled the t-shirt off.

Now remember, my sister had lost all her clothes in the strip poker game except panties and a t-shirt. So when she turned back to face me I could see her tits even though she was holding her arms up a bit. Her tits were small compared to the ones in the porno magazines but these were my sister's tits and I had been sneaking peaks at them since they started to grow.

These were my sister's tits that I had wanked so hard and so often over. Wow. These were my sister's tits and she was showing them to me. 'Oh Jenny, your tits are beautiful. I really like the shape of them. And it's great that they aren't saggy like Belinda Harrison's.'

In retrospect I think Jenny had been a bit insecure and that this had been the right thing to say because she smiled and sort of shrugged her shoulders. It seemed to me that she had practiced this move to get the opposite effect to when she had made them almost vanish the first time we had swapped clothes.

Jenny's breasts gently swayed. They were not big enough to wobble. Her nipples seemed erect. Before I had discovered dad's porn stash, boys at school knew all about this and we'd wondered if a woman's whole breast got erect like a penis.

And then, well then, if her tits had stunned me, the image of her hooking her thumbs into the waistband of her panties and just rolling them down while stepping out of them is burned into my brain. Years later wondered if she had practiced that move because she had done it so smoothly. At the time of course my mind was elsewhere.

At the time Jenny was taller than me (teenage girls can be huge compared to boys) and she had shoulder length mousy brown hair. Her breasts were quite small and she had almost no hair around her cunt. She stood awkwardly with her hands on her hips. I knelt down to get a better look at her cunt. She had curly dark brown hair in a narrow triangle above her cunt and no hair actually beside her cunt. I was also surprised as my thick thatch of pubes were black and abundant.

I asked why she didn't have much hair and my sister laughed.

'Don't be silly, Ian, I shave there. Most of the girls do.'

My sister shaved part of her cunt hair? So many questions, I didn't know where to start:

Teenage girls shaved their cunt hair and told each other about it? Or did they - pause - show each other? Were there popular styles? Did they do it themselves or did they help each other? Did they pay someone? Could I get a job shaving cunt hair? Could I take a course to learn and practice?

'Do you do it yourself?' I at last managed in a very not nonchalant gasp.

'Yes but Mum says I can have a salon treatment for summer'.

I'd seen Mum naked often - as I said we had a relaxed dress code - and I was sure she didn't shave so it was just one more mystery to file away about why only younger women shaved their cunt hair.

Staring at my sister's cunt hair had made me too far gone to be cautious so I knelt down and asked her to open her legs a bit so I could look at her cunt. She said no, but she would do what I had first asked for and would wear my underpants. I was in no mood to argue about anything so I passed them over. All my underpants were the same; grey cotton Y-fronts.

She stood to put them on - her cunt only inches from my face it seemed. She lifted one leg - and damn it she did a ballet leg lift! She held her leg out horizontally making her glistening labia rub past each other by a little - and stepped toe first into one leg of my undies. Then she lifted the other leg - also horizontally - with the same labia rub effect, stepped into the other leg of the undies and then pulled the undies up. She pulled them up and almost gave her cunt a wedgie. Then she sat down and rested her hand over her crotch.

You probably know that except for 'sexy lingerie' there is very little difference to see between the everyday teenage underpants for a boy and girl - apart maybe from some lace trim. But that wasn't the point. It wasn't the point at all. The point was that my sister was sitting there with her tits exposed and she was wearing my underpants.

Actually, now I considered it, there was a difference. It was in the way Jenny's underpants were so tight on me and mine were so loose on her. Stop me if you have noticed this, but boys have a penis and testicles, while girls do not.

This means, of course, that girls' panties are not shaped to contain such a bulge and so a penis, especially an erect one, is quite squashed. On the other hand, when a girl wears a boy's underpants, there is a noticeable lack of a bulge and a patch of the fabric hands loosely, a bit like a curtain. And so it was with Jenny. There was practically room to dance inside my underpants, or at least enough room for a hand.

AND best of all, there was a faint damp patch!

I finally could see what the porn letters meant when they said a woman was 'moist'. It was damn well more sexy than seeing her naked!

Then she put my shorts on. Even though it was a mundane act there was something erotic in the way this teenage girl looked when she wiggled her hips to fit into my tight shorts.

I know it makes no sense but she actually seemed sexier in my shorts with the undies hidden underneath than she did in just the undies. Again, it was the way my attention was drawn to what wasn't there, to the way the fabric was loose. Weird. I hadn't known that something could be more noticeable when it wasn't there.

It was just 'wrong', so obviously a girl in boys clothes and, as I saw it, such a naughty thing to do and I felt my erection straining even more. I thought I was being very crafty by pretending to be embarrassed but in the process drawing her attention to it. She was intrigued and pretended not to be looking but I knew she was. I asked Jenny to pose for me and behave like a boy and sit with her legs apart. (Mum was always telling her to sit with the knees together).

Jenny sat on the edge of her bed and opened her legs wide, really wide. Was that how girls saw the way boys sat? Maybe we did. Some boys sure did. At school some classes had columns of pairs of desks and some boys spread their legs so wide that their knees were in my space. I found this a bit threatening in an abstracts sense since I didn't play the cool kid game. I said all this and Jenny told me how creepy it was if a boy next to you did that and this was one of the reasons most teachers, especially women, always had boys on one side of the class and girls on the other side.

I was starting to realise that noticing the unjust differences in the way boys and girls behaved and were treated was going to be to my advantage. All this was about the time the term "snag" (sensitive new age guy) was being bandied about at school. Most girls *said* they wanted a snag but the fact was that it was the cavemen who got the action.

Anyhow, I stood back and tried to look up the legs of the shorts but I couldn't see anything. Jenny was fidgeting and I asked if she had to go to the toilet and without thinking I also asked if she was going to stand up and 'go like a boy'. She said she made a mess if she stood up. She suddenly realised she had just admitted to trying to piss standing and blushed but I pretended not to have noticed. But my fetish has always been pissing - especially Jenny's - and I filed the information away.

I wondered if she also 'played' with herself in the bathroom like me. We had a large bathroom with lots of mirrors and I liked to sit on the edge of the bath in front of one full length mirror while jerking off. I had a vision of Jenny with her legs apart doing... well I wasn't sure what she would be doing to herself but I liked the idea.

Then it was her turn and she asked me again what I thought about when I wanked. Now remember, I was standing here in front of my sister wearing only her panties. I wanted this to carry on so I told her my current favourite fantasy, omitting the detail that I imagined doing it with Jenny. Instead I just kept saying 'the girl'.

I told her that in my fantasy I wanted to be told what to do: 'Then the girl makes me her slave, I have to wear her clothes and follow her round everywhere. She makes me look like a girl and she takes me to school wearing girl's clothes. I have to follow her everywhere, you know, even the toilet and when she goes to the toilet I have to help her and stuff like that.'

Jenny seemed surprised. She had one hand stroking her breast through my shirt. She was cupping her breast and then squeezing the whole breast sometimes and tweaking her nipple other times. She had also unzipped my shorts, without me noticing, and was stroking herself through my underpants. By now I could even see a wet patch spreading - the cunt juices of all the Penthouse letters.

To start with she was just rubbing from the front but very soon she slipped three fingers into the Y opening of my underpants, and appeared to be rubbing in a small circle. It occurred to me just then that the ease with which she found the Y front opening might mean she had done this before. I mean, she hadn't fumbled to see which side etc.

'Help her do stuff. Like what?'

'When she goes for a wee, I have to help wipe and stuff. And then she makes me play with myself while other girls come in and use the toilet. The other girls try on clothes and stuff and make me pose and wear the clothes so they can see what it looks like. Then they all stand around me and touch my dick like you did and then they order me to do all sorts of things and then they make me wank while they watch. Then I wank and then...'

'And what then?' Now Jenny was laying back on her bed and had her hand in the Y-front of my underpants that she was wearing and rubbing hard and fast.

'Yes, Ian, and then what?' she repeated.

'Then I cum and clean myself up'.

I was standing mesmerised - half-heartedly stroking my cock because I was so stunned at watching my sister wank. Jenny stared right at me and paused in her stroking but started to clench her thighs together.

'OK', she said matter of factly - how could she be so calm? I felt like I was going to faint.

'I am wearing your clothes and you are wearing mine. Now tell me! Who do you think about when you are wanking?'

I just stood there, my cock throbbing and my eyes flicking from her cunt to her tits to her eyes. I was miserable and I knew if I told her that the most common object of my desire in my wanking movies was my own sister then it would all be over.

But once again my sister surprised me. She looked down at my painfully erect cock, her panties that I was wearing and to my face. She looked down at her own body - following my gaze and then Jenny looked at me with growing understanding in her eyes. She knew!

'It's me isn't it? You think about me when you are wanking. Why me?'

I had no idea what to say. I began to babble.