Um Both I Guess

So far:

I fancy my slightly older sister, Jenny. It seems mutual. We have stepped up a forfeits game to include clothes-swapping, and have agreed to swap underclothes next time.

Overview of this chapter:

We play forfeits. My sister gets me to wear her panties and she wears my underpants. She wants to watch me wear her other clothes and wank in front of her.

We both knew that sex with a sibling was wrong in some ill-defined way, but we were so close that we felt that the rules just had to be different for people like us. I struggled to put this idea into words over the next few minutes. I think I did pretty well in the end. Look, I wish I could tell you exactly what it was I said that helped her decide, or even if anything I said had been relevant. But, the truth is, I think it would have only worked for us at that particular time.

Especially, it only worked because we both wanted sex and we both wanted it with each other. It would not have worked otherwise and it probably won't work for you. Sorry, but I have no magic strategy to get a sibling into bed. Well, no strategy to for a brother to get a sister into bed. Sisters will be able to get anything they want from a horny brother.

A lot of the things we said to each other in justification for continuing were only relevant us. It went easier than I expected. Jenny also wanted sex and wanted sex with me.

My only advice if you are ever in a similar position or advising someone who is, is this: Be honest. Don't lie. If you really want sex then say so. Don't pretend it is about you 'teaching' the other person something, or that you are merely 'curious' or anything like that. Be brutally honest and say they turn you on and you really want to share your first sexual experiences, the ones you will always remember, with them.

This was relevant because we both had recently heard of several kids at school, girls, mostly, who had their first sex with someone they lusted over. Usually it was a sports jock and then for a while afterwards they'd been practically boasting – that was how even someone outside the gossip channels as me had heard about it. But then they'd broken up and felt used and cast aside.

The teachers knew something the rest of us didn't, I'm not sure how much, and had been all 'Wait till it is someone you really care about and will want to look back fondly on back when you are as old as us'. We talked about this aspect a bit and we both mentioned that Even when we found a partner (we didn't say 'get married', our parents had again immunised us about societal expectations) then we would still be siblings and would always love each other.

In our case Jenny had always been – as you will have realised – the more adventurous and dominant. I had always been willing to take orders from her. So I told her this, as if somehow she hadn't noticed. I abased myself and declared I wanted her to use me. We talked and talked about this for ages over the next few days.

I suppose it was only because we were similar in age that we were able to talk to each other so freely about anything. That and also the fact our parents and really trained us to question authority and ask 'who says so?' While I am sure they never intended their political rhetoric training would be applied to their children talking themselves into sexual acts, I am also sure that our parents would not have minded too much. And no, our parents never did find out.

Friday afternoon finally arrived. My sister Jenny and I knew we had the house to ourselves until at least midnight.

Jenny had gone straight to the toilet and I lurked in the hallway so I could bump into her when she got out. (See Chapter 2 for details of our 'master-slave' game). As usual I also enjoyed listening to the rustle of her clothes and the sound of her piss hitting the water. She finished, flushed and came out.

She must have had the same idea because we both had our arms out in the 'I am going to hit you' stance'. We giggled and waved our arms but she was quicker and anyhow I wanted her to be master so I made sure I 'hit' Jenny.

'Oh, you hit me. Now you have to be my slave' she told me with what can only be described as a lustful grin.

We went into Jenny's room. Somehow all the games took place there. She turned around with bright eyes and told me wanted us to play strip snap. Yep. You read that right. Snap. You know, the card game where you lay out cards and slap your hand down if they have the same value. I know poker is the traditional strip game but neither of us really knew all the rules of poker, and snap had the advantage of being really quick.

I have no idea what the hell she was thinking but she also suggested we steal some of Mum's gin again. We knew where it was and she drank so much that she hadn't missed it the last time we had stolen some. Oh, I think she suspected but to call us on it would have involved Dad realising just how much mum drank. So we poured ourselves a few fingers (oh boy had we learned the hard way not to drink heaps all at once) and added lemonade because we hated the taste of tonic.

We sat on the sheepskin rug and sipped our gins as we played. The crazy thing is I was certainly playing to lose but I think Jenny was making sure she lost a few hands as well. It was driving me wild – especially when our hands touched as we slammed them down for a snap. As we chatted it was plain that Jenny was worked up as well. We were both laying it on pretty thickly – each telling the other how much we liked them. We both kept on using the word 'respect'.

I had the idea that while she might be horny, I didn't think my sister really felt the way about me that I felt about her. If she did then I was sure I would have been fucking her right now. It never occurs to teenage boys but teenage girls can be just as horny - though not every waking minute of every day. But if you catch a girl at the right moment then there is no telling how far you will get. I realised Jenny must have been burning up to want to play a game like this with her brother and I was willing to do anything to make this continue.

We had been playing for no more than 15 minutes and we had more or less won/lost alternately and taken turns at telling the other to take something off. I was down to my underwear and Jenny had a long t-shirt and her panties on (boy short style bright orange with white lace around the waistband and leg holes) but had lost her bra.

This was pretty major – my sister sitting there and me staring at her tits jiggling under the t-shirt and her nipples pressed against the fabric. I had a noticeable erection tenting my underpants but neither of us had commented on it yet. I wasn't making any attempt to hide it and had adjusted my erection several times and I could see Jenny was staring when I did.

A few times, for no reason I could see, Jenny took a finger and ran it under the leg band of her panties. It was sort of like the bit in the movies when the guy runs his hand around the collar of his shirt. The panties didn't seem especially tight and her finger fitted easily under the elastic. As she ran her finger round I could see a flash of paler skin. I could also see the where her pubes made a slight bulge.

I had just lost, and I now owed two items but only had one left. We had already set the rule that after all the clothes were gone the loser had to carry out a forfeit – obey an order.

I asked Jenny what she wanted me to do. My sister took a deep breath and said quite suddenly and quickly, as if she had been nervously building up to it,

'Duh, obviously you have to get naked. Then I want you to wear my panties'.

I couldn't believe it. My sister wanted me to wear her panties while she watched? Didn't she know I already did wear them when I was alone? I mean she had got me to wear her dress just last week and she'd seen the bulge my erection made. And now she wanted to wear her panties. I was on a hair trigger and really hoped I'd get to wear warm panties fresh off her cunt.

I was feeling reckless and said 'Sure, do you want me to wear those ones?'

'No way, that would make me naked and I haven't lost. I'll get you some.'

She stood and went to her top drawer where her underwear were.

From behind I could see the little diamond of open air between her thighs as she stood with her legs together. I swear she gave her arse cheeks a squeeze just to wind me up and then she pulled out one of my favourite pairs that I had often worn before. Red nylon with a cotton gusset, brief style, with white lace trim.

Jenny held them out to me with an encouraging smile. I was excited to notice her gaze flicked between my eyes and my crotch. I stood up too and, as I reached out to take the panties, our fingers brushed. I felt I was burning up so I was a little surprised to feel that Jenny seemed to be red hot as well.

We both looked at our fingers and she slowly let go of the panties. I took them, and with one hand one each hip, I held them up in front of my erection bulging in my own underpants. Then I carefully put the panties down on the edge of my sister's bed.

I tried to keep eye contact with Jenny but she was definitely looking at my erection. I pulled down my underpants and let my cock sway up and down. Jenny opened her lips a little and quickly made eye contact. I smiled and received big smile in return. I may have been my imagination but read into her smile a sense of something shared. You know, that look strangers exchange in a line at an airport when an announcement comes over that means you are sleeping in the terminal. It is a look that forms bonds.

I picked up the panties. Even though I knew they had just come from her drawer, I still raised them to my face and took a deep sniff. Then I turned away and put them on facing away from her. Jenny told me to turn around and let her see how I looked.

Initially I refused, but she cajoled me into turning round. Actually this as exactly what I wanted and I was only pretending to be reluctant to give me a chance of getting her to 'do' something in return. Just as she had done when she had been wearing my shorts, she looked at the bulge. Jenny observed that it was obvious I really liked wearing her panties.

Since it really was obvious, there was no point in denying it so I said that I did. She wanted to know why. It didn't even occur to me to lie so I told her it was because it made me feel she was my master and I wanted her to make me do things. It was pretty obvious that this wasn't really news to my sister. Jenny was pretty shrewd, and must have guessed I had worn her panties before, that was her next question: 'You have worn them before haven't you?'

Again, there seemed no point in denying it. Besides it was well known at school that a boy in the year above me had been busted by his mother while he was wearing his sister's panties and had been severely punished (though nobody had quite the same story about what the punishment had been) and it had become an in-school joke to say a guy wore his sister's panties. But you sometimes felt some of the accusers were deflecting attention.

So I had to admit it. But somehow I didn't think Jenny was going to be too upset as it was one more thing she could hold over me. How convenient that my sister was turned on by bossing me and I so wanted to be bossed.

'Well, yes. I have worn your panties. A few times.'

'When? – Oh wait, I know on Fridays – right? I had guessed you were doing something like that. I was going to tell mum and Dad but if you behave I won't. And don't tell me it is only a few times. I bet it is lots and lots isn't it? So tell me about it. What else do you do?

I wasn't dumb enough to tell her of all the invasions of privacy so I gave an edited account of stealing panties from the washing basket and looking through her drawers and wishing I would wear the other clothes but implying that I had never done so. Jenny seemed intrigued. (Goodness knows why – if I was a teenage girl and found my brother had been wearing my clothes then I would have been repulsed). I told her I had worn her panties to school a few times and she gave me a funny look I didn't understand for a few minutes.

'Do you mean to say you want to wear other clothes of mine? But you expect me to believe that you never do? Why not? Do you ever wank in them? I bet you have done it.'

Uhh oh. My face gave it away even as she asked that last question. But to pile surprise upon surprise all she said was 'hmm, that might be interesting to see some day'.

What!? My sister thought it might be interesting to see me wearing her clothes and wanking? Had I died and gone to heaven? I took a deep breath and said 'Jen, I would really, really, like you to see me wear your clothes and wank for you. Please, please, let me do it. Today.'

I must have been all erection and puppy dog eyes.

'OK little big brother.'

Jenny hardly ever called me little big brother – unless she wanted something. It was a recent joke started by our parents. I was younger – her little brother – but I was growing fast – her big brother. I often called her little sister – especially since I had begun to fantasise about sex with her but she seldom called me her 'big brother'.

'OK what, little sister?'

'OK. You can wear my clothes and I will watch you wank. Pretend I'm not here and just do what you do.'

Really? Jenny wanted to watch me go through her clothes and put them on? And I was going to finally get my wish to have a girl watch me wank. Jenny repeated herself.

'Just pretend I am not here and do whatever you do or want to do with my clothes. You can put anything you like on. Talk about what you are thinking as you do it.'

I dunno, since then Jenny and I have done a lot of stuff but I think she is still the only girl I have ever met who got sexual pleasure from seeing a boy wearing her clothes – especially considering that the boy was her brother. But there was no way I was going to argue. I said that I would love to do that and I had always started with her school uniform and panties anyhow.

'I thought you did. It is sort of weird to know you are going through my panties. It is just like Brendan' [This was the name of the boy at school who had been caught wearing his sister's panties]. 'A lot of us girls wondered if our brothers were doing this. We talked about what we would do. Most of us said it was really yucky. But when we were alone, Leanne said if she had a brother she'd use it to make her brother be her slave.'

Huh? Who the hell was 'we'? And did my sister really talk about sexual ideas to other girls?

'Umm, what did you say?'

'Oh I didn't want to say anything to them or Leanne, but actually I do like the idea of us swapping clothes. A lot of the girls don't know very much about boys and don't have brothers. So they ask me what you are like. I told them you have a big cock.'

Huh? My sister, my sister had boasted to her friends that I have a big cock? How the hell would she know? Had she been staring at me as much as I had been staring at her? Why hadn't I noticed? I paused for a moment to let that sink in.

I am willing to bet that pretty much every teenage boy with a similar aged sister has put on her panties and wanked at least once and probably many, many more times than that. I had done this often and I had a little routine. I think Jenny knew this and if she wanted to watch, well then, I was happy to show her.

'OK', I began, 'I'll show you what I do but please don't get mad with me.'

'Nah, I promise I won't get mad. I'll sit here and watch.'

I told her that on several occasions I had worn her panties to school. (I wasn't quite ready to admit it had been many tens of times). The first time I wore them under my own underwear. That felt too tight to be really exciting

I told Jenny that the next few times I wore only her panties – without my own underwear. It felt wonderful to walk around the day with an almost permanent erection. I spent the whole time looking at girls and trying to imagine who was wearing the same style of panties like me. I was turned on by the vague possibility that a girl I liked might see up the legs of my shorts when I was sitting down and notice the lace trim. (Not that any girls ever tried to look up my shorts).

Jenny seemed to take these revelations quite calmly and I wondered how much she had already guessed. But even so it was going to be really weird with my sister watching me wear her clothes. But if I was honest I had been doing this for two years and the routine that involved putting on various items of her clothes was well and truly set.

From the floor I picked up and put on the white socks that went with the girls' uniform. I am not a foot man but there actually is something sexy about the smell of a girl's socks that have only been worn for a day. To save on washing, Australian cities often have water use restrictions, Mum gets us to make 2 pairs of socks last the school week.

This usually means that Friday's socks have been worn for 2 or even 3 days, but Jenny sometimes cheated and took fresh socks, so on some Fridays I get lucky and can smell her fresh sweat on her socks and her perfume on her dress. The socks are white with a fancy elasticated lace trim the top. Usually once I have the socks on keep them on for the rest of the routine but of course I didn't sniff them in front of Jenny.

She pulled a blanket across her lap and put her hands under the blanket. I just knew she was... well I wasn't actually exactly sure what she was doing - but I knew she was doing IT and I hoped it was because she liked what she was seeing.

I picked up a bra. It wasn't till I had seen Jenny do it under a jersey at the beach one time that I finally worked out you had to put the cups at your back then do up the fasteners, turn the cups to the front and slip your arms through the straps. Once it was on, I rubbed my palms over the cups and Jenny smiled and took her hands from under the blanket. She repeated my rubbing action over her breasts under the t-shirt. She gave me an encouraging nod.

I picked up Jenny's school dress, adjusted the floor mirror, and pulled up the dress so I could see my erection tenting in Jenny's panties. I posed for a while and did twirls and showed Jenny how I had taught myself to walk and make the dress hem swish.

'What's next?' she asked.

I explained I usually liked to walk around the house for a few minutes in the dress but I could see she was a little impatient, so I pulled off the dress.

'Ummm the wrap around shorts.'

Jenny doesn't wear many dresses other than the one for school but I do really have a thing for a pair of her wrap around shorts. [I haven't noticed these in years. When spread out they look like a butterfly and each side is tied in place with long strings at the hips]. The shorts are white satiny stuff with blue piping trim and an outline picture of a blue butterfly on the front of the right thigh. Jenny watched without comment as I took off the school dress and as I deftly put the shorts on and tied the strings. I positioned my penis between my legs and clenched my thighs and then slid a hand in between the flaps at the front and rubbed the pubes at the base of my penis.

Jenny leaned forward a little to see when I did that but didn't say anything else. The blanket fell away and I could see she had a hand down the waistband of her panties and was plainly wanking. I could see the outline of two fingers moving in a circle over her clit. A damp patch had appeared around where she continued to rub her fingers and she spread her legs wider and changed to a simple up and down rubbing – a bit faster than before.

It was time for my absolute favourite.