Sisters Know Everything

Sisters know everything right? Or is it just mine? Well, this is the story of how my sister found out my biggest secret that I'd managed to keep for a few years and then unveiled a side of herself that I never knew existed.

I was what people would usually call a typical 21 year old lad. My Mom gave me the name Joshua when I was born, but was never a fan so I always shortened it to Josh. I was currently studying part time at university whilst working a part time job. With the money I earned from the part time job I managed to buy myself a nice little car. We were based in a little town outside Leeds called Headingley. Close enough to Leeds to enjoy the shops and food outlets. I had an older sister, Jess. She was nearly 27 and had already moved out into a flat in the city. She liked the night life and having a flat next to all the nightclubs was a massive plus for her. Somehow she was able to afford living alone.

Now when I say I was a 'typical 21 year old lad', I suppose you could say there was probably a few reasons why I wasn't. Firstly, I wasn't interested in drinking culture. I'd never been in a nightclub which probably caused most of friendships to fizzle out. I'd much rather have a drink in the pub than in a nightclub where you can't move or have a conversation. Does that make me sound old? The other major thing was that I was a virgin. I'd never been with a woman and never had a relationship. I really wasn't a one night stand kind of guy.

Oh yeah, I almost forgot. The secret that I'd somehow managed to keep from my family for the last couple of years was that I liked to wear women's underwear. My sister had only recently moved out in the last 12 months and when I was 18 sexual frustration really began to set in. Every time I watched porn, I was always fascinated by the different lingerie they would wear and one day when my sister was out overnight with her friends, I snuck into her room and found her underwear drawer.

When I opened it, it was like heaven. She had every different style of panties going. There was thongs, g-strings, brazillian, cheekies, bikini, boyshorts and every kind of material; cotton, lace and satin to name a few. I grabbed a few pairs from the back of her drawer thinking those are the ones she's not going to suspect as missing. I got back to my room and started wrapping the various pairs that I'd taken around my cock and stroked myself. Then my curiosity got the better of me, I came across a lace cheekie pair from VS and I just couldn't resist. I slipped them up my legs and the lace felt amazing against my ass and cock. I wanked myself to completion that night wearing them and it was the biggest load I'd ever shot.

It started to become too risky to be stealing my sister's lingerie so I started to buy my own when I got my part time job. I still wasn't confident enough to go into a shop to buy panties so I would buy them online and use the click and collect service to pick them up. It was a real bonus when one of our national stores here in the UK started selling VS panties. I could finally get my hands on some of my own and I never looked back.

This meant I had to get creative when at home though. I was fine wearing them underneath my clothes and on a night to bed but I needed somewhere to hide the goods. In my chest of drawers I did some DIY on the bottom draw and attached a lock to it with only one key and made sure that I never left the house without that key. Once I'd bought my own panties, I started to wear them pretty much everyday and sometimes I was even brave enough to wear them when I went to Uni or work. I'd wash them every week when I knew both my parents were out and I'd have time to get them back safely.

Anyway, that's a bit of an introduction to my life. And now here I am in the build up to Christmas. My sister had moved out so it was now just me, my Mom and my Dad living at home. In the build up to Christmas, we'd always have a family get together when everybody broke up from work and school which was usually 3 or 4 days before Christmas. I was just treating it like any other family get together, I'd try and hide upstairs in my room until my Mom shouted me downstairs to join all the family. This normally meant that Grandparents would be there, Aunt's, Uncles, and cousins who you saw once a year would also be there.

When I was shouted down, I decided to take a risk. Underneath my joggers I had a pair of VS hiphuggers which were all lace. Figuring, after I looked in the mirror and realised you couldn't see any outlines through the joggers, I tucked my t-shirt in and then threw a hoodie over the top and headed downstairs. In the end it turned out to be an enjoyable night. We ate takeaway food, laughed and played party games. Isn't it great when you see how competitive every family member can be?

Anyway the night ended and the family all began to leave. I eventually was allowed to return to my room, where I stripped off my joggers and hopped straight into bed looking forward to a good night's sleep. It's a good job it was a good night's sleep because when I woke up the next morning the text/conversation I'd been dreading happened. When I woke up and checked my phone, I already had a text message off Jess, which was highly unusual. The conversation when something like this:

Jess: I saw what you were wearing last night... xx

Me: What do you mean? xx

Jess: We're going to play that game are we? xx

Me: I'm confused lol, what you talking about? xx

Jess: It was so obvious last night and a lot of things now make sense xx

Me: What? That I'm really good at Pictionary? xx

Jess: Oh come on Joshy, your arse was literally in my face while you were drawing on the flipchart. I could literally tell you what panties you were wearing xx

Me: You're talking a load of rubbish... I have no idea where you've got that from xx

Jess: Cut the crap. There's two ways this can go, you can either come over to mine tomorrow and we can talk about this... or the photos I've got of your little lingerie drawer will be in the family chat tomorrow night. Merry Xmas bro xx

Me: Fine, I'll be over tomorrow xx

Jess: Good, and don't think about wearing boxers.... make sure your wearing a pretty pair of panties xx

After that, the conversation ended and I was mortified. I felt sick all and I barely ate anything all day. How did she know? I'd always been so careful. Then another text came through to continue the awful dare.

Jess: Just placed a little order at VS... I hope you don't mind picking it up for me on your way tomorrow? It's under your name, thanks sweetie xx

I didn't even have it in me to respond to that one. Anyway, the day came and went and I focused on trying to get a good nights sleep ready for tomorrow. It's safe to say that didn't go to plan and I spent most of the night tossing and turning. I laid awake for most of the night trying to figure out how I'd been caught. I always thought I was so careful, always made sure there was no VPL, always wore baggy clothes so nothing could be seen and I always wore oversized hoodies so if I ever bent over, there was no chance of me flashing anybody.

Anyway, before I knew it, daylight was beaming through my blinds and I'd barely had a couple of hours sleep. I'd taken my panties off last night before I went to bed as I felt extremely guilty about being found out. My fate was now literally in my sisters hands, she could ruin my life in one message. Me and Jess had always been pretty close when she lived with us. We used to go out places together and she always looked out for me if I was ever in any trouble. And in return, I would never tell our parents about the house parties she had when they were away and the time I actually caught her and two of her friends (one who was female) going at it in our parents bed.

I digress, I got myself out of bed. Jumped in the shower and washed myself, I shaved the tops of my legs and then my ass and my balls. I've been doing that for years. It feels so much better when wearing panties. I then spent a long time trying to decide which panties I was going to wear today. I don't know why, it wasn't like anyone was going to see them. In the end I settled on a leopard print V-string from VS, put my jeans on over the top and finished it off with my usual hoodie combination and headed out not before letting my parents know that I was spending the day with Jess.

Living in Headingley, meant I was only a short 10 minute train journey away from the city centre which was good. The less time I spent out in public the better, just in case I bumped into anybody. Once in the city centre, I made my way to where all the shops were and soon found the Victoria's Secret store. It was extremely hard not to get distracted when I was walking through towards the tills to collect the parcel.

It was made worse by the number of girls that were in there who were my age and they were all picking up the different styles of panties, holding them against themselves to see if they like the fit. One of them was even holding the exact pair I was wearing. But being in a lingerie store as a male, does mean you get some dirty looks. Which I completely understand, I must look like a complete creep working my way to the back of the store.

Once I'd got there, I had to wait in a massive queue behind a lot of people who were spending a lot of money. When I finally got called forward to the next checkout, my heart dropped. Standing behind the counter was a girl I went to college with. I could already see her smiling at me as I made my way towards her. But as I was walking past the girl who had just been served, she dropped her card on the floor. I picked it up and handed it to her before turning back to the till.

As I approached the counter, Heather; the girl behind the counter spoke:

'Good to see you've already tried the products we have on offer and I must say it's an excellent choice.'

My face must've gone instantly red. And I had nothing to say. I just wanted to turn around and run.

'What can I do for you?' Heather asked.

'Ermmm.... I've got a parcel to collect.' I managed to stutter.

'Give me two seconds, I'll go and have a look for you.' She disappeared into the store cupboard behind the tills and was gone for a couple of minutes before she returned holding a very large pink bag.

'Here you go,' she handed me the parcel over the counter. 'You can also try on the items you've bought instore if you'd like? And we can organise any returns straight away.

'What's in the bag isn't for me,' I responded quickly.

Heather just smiled at me, 'Your secret is safe with me, maybe I'll see you again sometime.'

I turned and made a hasty exit from the shop and back onto the streets of Leeds. Luckily Jess didn't live to far away from all the main shops but I still got some people staring at me, probably wondering why I was carrying VS bag. I made it to Jess' apartment and hit the buzzer for the telecom.

'Hello', Jess' voice appeared.

'Jess it's Josh.'

'Oh hi Joshy, did you get the parcel?'

'Yes! I've got it with me now.'

'Excellent! And are you wearing your panties.'

I was fuming. I looked around and luckily no-one was within earshot. 'Yes I have, please let me in.'

Finally, I heard a buzz and then the door unlocked and I was inside. I took the lift to the 7th floor where her apartment was and knocked. Jess answered the door wearing a silk robe which showed off her cleavage perfectly. Is it weird I had some sort of crush on my sister and had done for a long time? She had long blonde hair which went half way down her back, she had fake tits which our parents had helped pay for and she had a killer ass from working out at the gym. She'd never had a long term relationship and never really had a boyfriend, but I imagine since she moved out, she's had regular hookups.

'Hey Joshy, come on in. You can leave the parcel on the table, we'll get to that later.'

Jess' apartment was nice. It had more of a penthouse vibe to it and I had no idea how she afforded it. In the living room was enough space for a corner sofa and a dining table. The room had floor to ceiling windows that overlooked the city. She had a large bedroom as well which had a Queen size bed in it with huge wardrobes down one wall. Then the bathroom had a walk in shower. I sat on the sofa while Jess brought me over a cup of tea.

'So how was your little trip to the store?' She asked me.

'Fucking embarrassing.' I said with a tone of anger in my voice.

'Why? What happened?' She laughed.

'Well not only was I served by a girl I went to college with, I also helped pick a card up off the floor that another girl had dropped and when I picked it up, I clearly flashed the girl who was working there the thong I'm currently wearing.'

Jess was in fits of laughter and as annoyed as I was, I could still see the funny side of it.

'I can't believe you're actually wearing panties, I never thought in a million years that you actually would.'

'You threatened to tell everyone you bitch?' I said laughing, 'it didn't feel like I had a choice.'

'Josh... come on. Did you think I'd actually tell everyone. Given how close we are, I thought you would know I was joking. Your secret is well and truly safe with me.'

I felt a weight lifted from my shoulders after she'd said that.

'To be honest, I'm kind of glad somebody found out. It's been eating away at me for years.'

'To be honest,' Jess said. 'I knew you were stealing my underwear, you weren't very discrete with that. Returning my panties with cum stains all over them was quite obvious, but I never thought you were wearing them. I thought you were just jacking off with them.'

'Well that's how I started off, I was only jacking off into them and it tended to be the ones you'd thrown in the laundry. Then I got bold one weekend while you were away and started rummaging through your drawers. Once I seen the sexy panties you kept at the back of the drawer, I couldn't resist trying them on and I've never looked back since.'

'Well I'm glad you can be honest with me now,' she said putting her hand on my thigh.

'I hate to ask, but what's in the bag?' What have you made me collect?'

'Don't worry about that yet.' She told me, 'we need to find out a lot more about you first before we decide what to do with that.'

She took my cup of tea from my hands and placed it on the coffee table in front of me. 'We're going to try a little game,' she said. 'I need you to put your head back and close your eyes. I'm going to ask you 10 quickfire questions and I want you to not think about them and just answer. It's the best way to get a quick answer.'

'Okay,' I said nervously and followed her instructions.

'Ready. Okay, here's your first question. Boxers or panties?'

'Panties'

'Favourite style of panties?'

'Cheekies'

'Do you watch porn?'

'Yes'

'Do you imagine you're the girl in the porn films?'

'Sometimes, yes.'

'Have you ever had sex?'

'No.'

'Awwww, my baby brother is still a virgin. Have you ever played with your ass?'

'Yes.'

'Are you gay?'

'Don't know.'

'Do you want to be fucked in the ass?'

'Yes.'

'Do you want to dress as a girl?'

'Sometimes, yes.'

'Will you let me dress you up?'

I opened my eyes and looked at her. 'What do you mean?'

'Well, I've always wanted a baby sister and I want to give you the opportunity to dress as a girl. You won't have to leave this apartment if you don't want to but I'd like to take you out for something to eat with my girlfriends later.'

'I can't go out in public, I'll look stupid. There's no way that's happening.'

'That's why I'm saying you don't have to if you don't want to, but let me work my magic and if you want you can stay here while I go out and entertain yourself.'

'I'm not getting out of this am I?'

'Absolutely not. First things first, go jump in the shower and remove all hair from your body. There's some hair removal cream or a razor, it's up to you.'

I accepted my fate, I didn't know whether or not to put up a fight to make it look like I didn't want to do it, but I didn't. Instead I got up from the sofa and headed towards the bathroom.

'Wait,' Jess called me back. 'You need to take off those clothes now, so I can hide them away from you for the rest of the day. Plus... I really want to see what panties you chose.'

I reluctantly took my socks and shoes off first, then took my t-shirt off and dropped it on the floor. Lastly, I took off my jeans, and tried to quickly get in the bathroom before Jess could see.

'Oooooooo they're cute. Luckily I didn't buy those when I bought you some more panties in the VS order.' I heard her call out to me as I got into the bathroom. 'When you're done, just throw on the robe that's on the back of the bathroom door and meet me in the bedroom.'

I jumped in the shower and washed myself as clean as I could before starting on the hair removal. I used the cream to remove all the hair off my body and to smooth over my ass and balls. I then moved onto the razor and shaved my legs, arms and face, leaving my body completely hairless from my head down over. Then I got out of the shower and dried myself off.

Rubbing my hands over my legs with some moisturiser I found in one of her bathroom cupboard was amazing. My legs felt incredible hairless and they looked even better shiny when I'd finished moisturising. Immediately my cock was standing hard and proud out in front of me, all 6 inches of it. I took the satin robe off the back of the door and put it on, fastening it at the waist. It did nothing to conceal my erection and the feel of the satin against my cock wasn't going to help. I tried tucking it up under the belt of the robe and headed towards the bedroom.

As I got into the bedroom, Jess was waiting on the bed for me, next to multiple lingerie sets, panties and even nightwear. She'd obviously opened the parcel. My eyes went wide like a kid in a candy shop.

'Someone clearly enjoyed their shower.' I looked down and Jess was obviously referring to the fact my cock had slipped from it's hiding place but luckily wasn't on show.

'Grab a seat and let me get started,' she said. 'Do you trust me?'

'Absolutely not, so let's get this over with before I change my mind,' I said laughing.

So I was sat in the chair at her vanity table facing away from the mirror when Jess started working on my face. I don't even know what she was doing but there was a lot of brushes involved. Lots of different colours, she rubbed what I assumed was foundation on my neck. I had seen girls who blend it in so it matches their skin tone. She must have spent 10-15 minutes doing stuff like this before she reached for a plastic box and pulled out some fake eyelashes.

I wasn't to pleased about this, but she reassured me they come off easily enough and not to worry. Once these were attached, she then applied some eyeliner and mascara and before long I think she was just about finished. The final touches were the lipstick before she disappeared and then returned to the room with a blonde wig which looked like it had shoulder length hair. She put that on me as well and then tied the back in a ponytail and turned the chair around so I could see myself for the first time.

'Holy fucking shit. What have you done?' I said.

'Do you like it?' Jess seemed almost giddy with excitement.

'It feels weird, is that really me?'

'You look incredible sis. I think you were born to be a girl.'

'I do feel good, and you even managed to hide my adams apple to a certain extent.'

'So you like it?'

'Yes,' I said reluctantly.

She clapped her hands together excitedly. 'Brilliant, next we need to get you dressed, but we can't do that till you've done something about that problem between your legs...'