Um Both I Guess

Then I tried something we hadn't done yet.

I unhooked my chin from my sister's shoulder, tilted my head back and looked Jenny in the eyes. Then I puckered my lips and slowly moved in. Jenny's smile crinkled with real warmth and lust as she tilted her head the opposite way and accepted my kiss. Have you ever kissed your sister on the lips, while your hard cock presses against her thigh that she is grinding into you? No, I suppose not too many people have.

After all the sexual things we had already done it didn't seem to have occurred to either of us to just kiss. It was a really intense feeling. I understand why prostitutes charge a premium for what they call a 'girlfriend' experience that involves kissing and hugging. These are intimate things that are much harder to fake. Fucking is easier and I guess you can detach yourself from it.

While still kissing me, my sister Jenny loosened her hug and began to run her hands up and down my side from my armpits to my hips. I did the same to her. We broke the kiss and looked at each other. At this rate we both knew our long imagined first fuck would be a grubby rutting on the kitchen floor. Neither of us wanted that and I was relieved when Jenny finally spoke and said

'Oh my. We need to slow down big brother.'

As if saying that was going to help me calm down.

'Should we play The Game?' I managed to croak out.

'No. Not right now. I'm going to shave you.

I should say that while my sister was saying all this she had been taking her clothes off.

'Why do you think I am doing this sex stuff with you? Look, I really enjoy the games we play. They make me wet.'

Jenny stood there in white sports bra and the same panties I'd seen in the morning -- the really tight old red pair I had been sneaking to wear myself. Jenny was rubbing her left nipple with her right hand and had her left hand down the waistband of the panties, cupped over her cunt. She stopped and pulled her hand out to show me a glistening couple of fingers.

'Come on, Ian. Let's get you shaved before mum and dad get home.'

She rubbed her cunt through the panties as I watched until I could see a damp patch. Then she pulled them off and handed them to me. I took a deep sniff. Then she watched as I undressed and passed over my underpants.

She was about to put my underpants on when I said, 'No, let me look at you all smooth. I really like it.'

Jenny stood back and used her thumbs and forefingers of both hands to make a downwards pointing triangle around her bald cunt. Then she broke the triangle, pressed the first two fingers of her left hand together so they were vertical and hard up against her labia and clit. The she squeezed the fingers together so that her labia bulged over the top of the fingers.

Does squeezing the labia like this have a word? If not I propose 'cunt muffin'. Her labia were already engorged and squeezing like this seemed to make them throb.

Her clit was peeking out like it had in the morning and glistening. With her free hand she used the pad at the tip of her finger to rub it a little. Round and round like she was winding it up. Then she gave it twisting pinch and let go.

'OK, Ian, come into the bathroom and I'll get you lathered up.'

In the bathroom, Jenny laid a towel on the floor and got me to stand on it. Then she wet her hands with warm water and brushed the water over my pubes. Taking a bar of soap she knelt down and rubbed the soap in small circles working up a lather, all the while keeping up a stream of inconsequential chat. I could only assume that was what her hairdresser was like. I supposed I'd have to learn small-talk if I ever wanted to get that job shaving cunts.

Then Jenny filled a small bowl with hot water and soaked one of her disposable leg razors. She took out the razor, flicked off the water and paused to look up at me.

'Ready?'

I nodded, making my cock wobble. Taking hold of my cock in one hand she bent it to the side and with the other hand placed the razor at the base of my cock. The razor was hot from the water and whips of vapour drifted up a short distance. Then she began to smoothly pull the razor towards my hip. A pile of lather was pushed ahead and I could feel many hairs being removed, with the occasional snag and tug.

At the end of the stroke, Jenny rinsed the razor in the hot water and continued making parallel strokes. It only took about 6 strokes on each side to get the bulk done. Then Jenny rinsed a cloth under the hot water and wiped the area clean. There were a few bare patches but also lots to tufts of partly cut hairs. Jenny refilled the water bowl, rinsed the razor, and reapplied the soap.

After the second round, Jenny again wiped the area clean. She tilted her head to admire her work. Then she took a fresh razor and a bottle of baby oil. She poured some oil into her palm and rubbed it over the area where my pubes had been but there was now a patch of stubble.

This time she leaned in much closer and again I felt her hair fall forward and brush against my cock. And this time it was a much smoother ride and I felt the stubble simply glide away. Then she did something unexpected. One of her fingers strayed to my arsehole and spiralled around it.

'Ian, I sometimes play with my bum. Do you?

I nodded. We had already talked about this at the beach and she knew I did, so I tried to ease myself back onto her finger but she moved it away.

'Not now, brother dear, later.'

Satisfied, Jenny stopped, rinsed the cloth and wiped me one last time. Then she patted me dry with a towel and stood up.

She put her arms on my shoulders and pulled herself in sideways so her legs were either side of my right thigh. Jenny began to rub her smooth cunt up and down on my thigh. I could fell the labia parting and fell her cunt juices smearing. So much for her plan not to do anything sexual!

I was panting and more than ready to respond but, ever the tease, she stopped and said 'Right, we'll both probably need a re-shave before too long. You can do me then. But right now, put the panties on and we'll get dressed. Let's pretend we are boyfriend and girlfriend'

I understood now that Jenny wanted to pretend we were boyfriend and girlfriend so I reached my hand out and held her hand, pulled her close so her breasts pressed against me, and kissed her chastely on the cheek. Pretend? Maybe she really wanted us to *be*, not pretend to be? An idea to park for now.

No flashing on Friday morning because Mum and Dad were leaving soon after breakfast and were bustling around the house -- popping in with last minute instructions. But, really, they were genuinely not worried about us. They even attributed our mutual friendliness to their parenting skills and we were not inclined to argue.

We had usually each cooked one or two evenings a week since we turned 12 so we were pretty good cooks. We had phone numbers to call in an emergency. We had an envelope of cash. I think they were honestly glad they could go away and get stoned with their mates.

We left for school as usual. I was sure that something of my strain and anticipation must be screamingly obvious but our parents didn't seem to have noticed.

One comment from Mum, that we should be 'moderate' confirmed what Jenny and I had suspected. 'Moderate' was usually code in public health adverts for drinking alcohol. Jenny and I figured they had left most of a bottle of gin in the back of the freezer on purpose for us. While they were packing, Dad had called out to ask if Mum knew where the gin was and she'd called out that she was sure there was none in the house. Dad had then added it to their shopping list.

The funny thing was, we'd noticed it when we were putting away the food they had got to see us through the weekend. Jenny and I were both sure the bottle hadn't been in the freezer the day before when we had looked carefully to see what food we needed. The reference to moderation was likely an acknowledgement that the booze was for us but also a warning to make it last.

We'd done the calculation it looked like they had left us 3 or maybe 4 shots each per night. Or, enough for one really heavy session. Clearly, it was their wish to avoid heavy drinking and instead for us to spread it out, that prompted the comment.

Anyhow, we went to school. The teachers were not expecting too much on the Friday afternoon before a long weekend so I got through the day despite my mind being well and truly focussed below my sister's waist.

The walk home was complicated by a group of friends who walked part of the same route home. In fact, one of them included Mike. Mike was probably my best friend. I obviously hadn't told him about me and Jenny and I also hadn't told him that we'd be alone. When we'd had a sleepover last year, we had watched each other wank while wearing a pair of Jenny's panties. I described this in some detail to Jenny twice now. (On the second telling I'd admitted we had been wearing her panties)

Anyhow, Mike was full of talk about how he was going away with his family to visit fun relatives. We pretended doom and gloom at being dragged to the folk festival again. Since we did this every year, Mike accepted it and commiserated with us. Mike carried the conversation of the little group till he reached his street and turned off. One by one the small group dispersed until for the last few hundred metres it was just us.

We hardly talked. The immensity of it all was stifling. Just before the letter box I said,

'Jenny, I'd really like to hold your hand but I know we can't.'

'In a few minutes we will do more than just hold hands, but yeah, I get what you are saying. Thanks.'

We turned down the driveway to our house and Jenny looked behind us, then she took my hand in hers, twirled around to face me and pulled me into a hug and a full on kiss. I was reassured to see the car was gone. I need to pause and explain the way the houses worked in our suburb. Along our street the back section houses sat on a half-acre behind a front quarter-acre block of land and house. Our house was a back section and was reached by a long driveway.

This being suburban Sydney, the back driveways were tree lined and private. We had one of the half acre blocks with plenty of trees. At the rear was the land was a mirror image of a similar pair of houses that were reached from another street. Once we were home then it would be very private.

An early plan to go out to a restaurant, not a takeaway place, had been thwarted by the need to keep a low profile. We had promised our parents we wouldn't have too many people over. They were cool with some trusted friends visiting -- they had even said they could stay over. But in fact we wanted the privacy for fucking so we had actually told all our friends we would be away.

This meant, we had belatedly realised only a few days ago, that we couldn't go anywhere in public where we might be seen. So instead I phoned an order for pizza to be delivered at about 7. (It was always safer to put the orders in advance because it was a little local place that only had one driver who did a run for several orders at a time. But if you were a regular and you ordered early then your order was first for the run and was hotter.

Jenny was all business-like:

'After the pizza arrives, tonight I want us both to wear girls' stuff. These.' Jenny held out both sets of the nightwear I mentioned earlier. The blue set and the yellow set.

'We can both put them on after we have a bath.' Jenny noticed as my cock twitched.

'Yes brother dearest. A bath. Together.'

I was a little confused. We both liked cross dressing so I'd been expecting we would wear each other's clothes for the weekend and roleplay being the opposite sex.

'OK but, umm, don't you like wearing boys' stuff?'

'Yes, yes I do. Very much.'

This was new side to her. I liked the directness and found it exciting to hear her 'talk dirty'. I managed a dry swallow and a nod before croaking a 'uhh, but why...?' Jenny blushed. But I don't think it was pure embarrassment because she looked directly at me and I recognised the look. Not defiance. More like certainty.

Jenny carried on. 'I know we talked about us wearing each other's clothes all weekend and I really do like pretending to be a boy -- most of the time. But I don't always want the same thing.'

She paused and I waited, giving her an encouraging nod because I really didn't know what was going on anymore.

'Ian, sometimes I think of weird things.'

Huh, as if I didn't? I wanted to hear Jenny's dirty fantasies. Honesty had worked wonders with her so far, so I said, 'Umm Jenny, I'm the one who thinks of having girls piss on him. And even that isn't the weirdest thing I think about. Everybody has those fantasies. Hey, even I know that you don't have to want to really do it. I mean, I think about all sorts of other stuff I would never do - but I still like thinking about it. You can tell me. Umm, in fact if you can't tell me then I doubt you will be able to share it with anyone ever.'

'I know Ian. But is still hard to say it out loud instead of just rubbing my clit and imagining. OK, this fantasy has to do with the whole boy thing. Look, you wank to lesbian porn right?'

I nodded, Jenny knew this.

'Well a lot of girls are the same, and gay sex -- boys fucking each other - really turns me on. Oh, no I haven't seen much. But the idea. Well, I dunno. It just gets me going. OK, so like I don't like thinking about being a boy and fucking a girl. You look great in panties and all, but I like thinking about *being* a boy fucking a boy. I want a cock. I want to watch a boy suck my cock and I want to cum in his mouth. I want to fuck a boy and I want him to fuck me. I practically melt when I think about 2 boys sucking and fucking. Especially the fucking. The idea of a cock up another guys bum makes me cum every time.'

Many years before 'too much information' became a phrase, I experienced the feeling. My sister has just told me that while she is masturbating, thinking about gay sex makes her come. I suppose I had already been emotionally blurting and disclosed my deepest fantasies, but somehow Jenny's were so much more physical.

Her fantasy totally made sense. I sure did wank thinking about lesbians. In the years since then I have found out I was a little unusual in that I fantasised about being an observer. Apparently a lot of other male fantasies of lesbian sex involve the women knowingly putting on a show for the male observer and then quickly drift into 3-somes. Instead, I usually thought of two (or more) women -- usually the art teacher at school and one of the senior girls -- having sex. Just them, without me even seeming to be in the room. Anyhow, today, for a change, I was the calm and mature one of us, so I parked the other fleeting visions and focussed on Jenny.

'Do you mean you want to watch me have gay sex? I bet I could arrange that with Mike if you wanted. He really fancies you and we have wanked together heaps of times. Umm you might need to encourage him a bit, I dunno, but I bet he'd go for it. I can call and ask him to come over.'

'Well, to be honest, that is more or less what I think about when I am wanking...,' but, seeing the look that must have flickered over my face she hurried on, '...Oh! No, no, not you, well not only you, just, well, gay sex in general. Or well, I suppose, sometimes it is you. But that is just imagining, and I am totally not ready and it would totally freak me out. This weekend I want it to be just us'

'I think I understand, Jenny. I mean, I think about some weird stuff when I'm wanking and they really turn me on to think about them, but that doesn't mean I would ever actually want to see or do any of those things.'

Her suggestion to keep quiet and not let anyone know we have the house to ourselves was something of a relief for several reasons. I didn't want to share my sister. Also, to be brutally honest, for me sex was sex. I took it where I could get it. I mean, I really enjoyed wanking by myself. But that wasn't as much fun as wanking with another guy watching, and better was holding another cock. And, clearly, playing with a friend was a less fun that fooling around with my sister.

I did like the idea of combining the two. I thought it would be freaking amazing to have Mike's cock up my arse while Jenny spread her legs and wanked while she watched. But I wanted to fuck my sister before we try anything like that. I snapped my attention back to Jenny.

'Just us. Yeah. Hey you know what Jenny? I know that soon we will each fuck for the first time. And I am, really looking forward to it. But I have just realised that this is the chance for us to have a lot of other sex firsts.'

That 'first for each other' idea seemed to be the trigger for Jenny. Her words came gushing out.

'Oh Ian, Ian. One of my fantasies is that I wish we were brothers. One time this weekend we can pretend I'm your brother and, well, you know...'

Yes, I did have a good idea about what she meant.

My sister Jenny and I are alone in the house for 3 days. We have been planning a weekend of sex but even in my most full on fantasy had I imagined I'd hear her say that she wished we were brothers so dot dot dot, where I filled it the dots as meaning 'so we could fuck each other's arses'.

I thought fast. I certainly enjoyed ramming a hairbrush handle up my arse and I was sure Jenny did too. A big part of her motivation was that Jenny wanted us to be each other's first. That meant I didn't want to seem like I was experienced and admit I had been fucked up the arse by a friend.

'Jenny, if you were a boy I'd take your cock in my mouth every morning and in my arse every afternoon. But...'

'I know, but I'm not a boy. But, ok, what I mean is that maybe you could, well, um, you know, treat me like a boy.'

I stared. Had I heard that right? Did she mean what I thought she did?

'Jenny, do you mean you want umm, you want me to umm, do you want me to, well, bum-fuck you?'

Having come this far Jenny seemed able to relax and speak plainly. Jenny was now curiously calm and was watching me carefully.

'Yes, Ian. Sometime this weekend I want you to try fucking my bum and...'

There was of course only one thing I could say.

'Pogue Mahon, Jenny. To kiss your arse is amazing. I can hardly believe you would trust me enough to let me fuck your arse. Oh that would be so cool. We could pretend we are brothers! And Jenny, you know, umm, I'd really, really, really like it if you wanted to put something up my bum.' Jenny's eyes flashed. 'We are going to have a bath together and then we'll see what happens.'

I had to pause and consider if she really did want anal sex or if it was just an image that made her cum. Even at 18 I knew the difference between what people are actually comfortable doing and they the stuff they *say* they want to try. I mean, even excluding the physically impossible things, some of the images I ejaculated to were not things I really wanted to see or do.

I was pretty sure I did very much want to play piss games with Jenny. I was open to the idea of being fucked by Mike while Jenny watched. I was pretty sure I would not really like being a servant in the girl's toilet at school (skipping over the implausibility of the situation -- maybe Jenny could have helped set it up for a morning...).

If I had learned one thing, it was that my sister was leading and I was willingly following and that on the day she let me wear her panties, I had already achieved more than I had expected to do before I got to university. It didn't matter it Jenny didn't really want to do some things.

As it transpired, my sister had a lot of ideas and put some of them into action.