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…’

‘I’m going to wait in here,’ she continued. ‘In the living room is my laptop, a box of tissues and some lube if you want it. Go and do your business, then clean up and come back in. I promise I won’t disturb you.’

I got up carefully from the chair, trying not to expose myself to my sister and headed to the sofa in the living room. I opened her laptop and quickly searched on the internet for my favourite pornstar at the minute, Daisy Taylor. I then quickly found my favourite scene of hers, where the top lets her cum first at the end before he cums inside her. I always love how she stays hard when she’s being fucked.

I got myself comfy on the sofa and untied the robe letting it fall to my sides so my cock was exposed. I then gently started to stroke myself to the rhythm of the fucking on the screen. I never like to rush myself when I had a jacking off session but I knew I had to be quick because Jess was waiting. As I was jerking my own cock, I kept looking across to the lube and I couldn’t resist.

I grabbed hold of the bottle, shimmied myself forward so I could rest my feet on the coffee table, leaving my hole slightly exposed. I applied a generous amount of lube to my finger and let some slowly drip from the bottom of my balls towards my hole. I then pressed my finger gently against myself, opening myself up slightly before it slipped in. I rubbed the inside of my ass gently once I’d found my prostate. I could feel my orgasm building quickly and I wasn’t going to be able to hold out much longer.

As I passed the point of no return, I looked up and I was almost certain that in the reflection of the TV screen which was turned off, I could see Jess standing in the doorway to her bedroom with her hand inside her own panties. I let out a long moan, as the first load shot from my cock and I was extra careful not to get it all over my face as the shots landed on the top of my chest. I then quickly headed to the bathroom, and washed myself quickly making sure to clean up all the cum and lube from my ass before heading back into the bedroom. I had absolutely no problems with the robe this time, my cock now shrunk back to it’s flaccid state about 3 inches.

‘Feel better now?’ Jess asked me as I got back to the bedroom.

‘Do you?’ I smiled, giving her a look that told her I’d knew I’d seen her. She just blushed.

‘Right, it’s time for you to get ready. You have your choices of lingerie on the bed and I think I’ve got a couple of old clothes that may fit you.’

I picked up and inspected the lingerie, there was a selection of all the different panties that VS sold in their 5 for £26 offer and then there was some of the more expensive stuff. And by expensive stuff, I mean the panties that had ‘Victorias Secret’ written on the straps of the panties in a bejewelled sort of way. And these had the matching bras as well which were even more expensive.

As I was checking out the lingerie, Jess was rummaging through her wardrobes trying to find me an outfit to try on. And my God, I’ve never seen so many sex toys standing on top of the drawers that were inside the wardrobe. There was dildos, vibrators, massagers and even a couple of harnesses.

‘Fucking hell Jess,’ I said shocked. ‘Have you raided every sex shop in town, you can’t have left much for anyone else.’

‘Just as a man has needs, every woman does too.’ She told me.

‘So what’s the harness for? Surely that’s for other people to enjoy.’

‘Well…. lets just say I like to fuck men and women. So the harness comes in handy.’

I felt my cock twitch when my brain started imagining her fucking another woman. But I managed to distract myself with the lingerie and picked out the blue set which had a brazillian tanga brief and a matching bra. With my cock being nice and soft and relatively small, there wasn’t much of a bulge in the front of the panties as I pulled them up my legs. I then slipped into the bra and put the robe back on while I waited for Jess.

Eventually Jess had finished turning her wardrobe inside out and came back with more than one option for me. Firstly though, she handed me some sort of fillet looking things. Then she told me to shove them inside the bra to make it look like I actually had tits. And to be fair, once they were in, they did a pretty good job. She then held up the 3 different outfits.

Outfit one was a black jumpsuit which had a belt stitched in around the waist. We were concerned though that seen as though it was quite fitting, it could show off any of my excitement throughout the evening. She then showed me outfit two and I just wasn’t feeling it. It was a maxi dress that went from the neck all the way down to my ankles, and even though she would have to convince me to go out, I would’ve been freezing seen as though it’s sleeveless.

Finally, when she showed me outfit three, it was the one I wanted. It was a red dress that had full sleeves which were lace, the chest was lace and the skirt was flowy and wouldn’t have been tight on me. Jess helped me get it on and it fit like a glove. It was like it was made for me, once I got it on I did a little twirl in front of the mirror admiring myself and not recognising myself at the same time.

‘Don’t be twirling to much, or everybody will see what you’ve got on underneath that dress.’

‘Who said I’m going out like?’

‘Awwww come on Joshy, you look incredible. I’ll tell the girls who you really are so they know and there won’t be any awkwardness.’

‘I don’t know, that feels like a pretty big step.’

‘You’ll be fine. We’re mainly going to gay bars anyway so no-one will know who you are.’

‘I’m putting a lot of trust in you Jess, but I’m willing to give it a go.’

Jess started dancing around excitedly like a child at Christmas.

‘Right then, sit in the chair and let me do your hair and you also might need these and these.’

She chucked me a pair of tights, and then a pair of black heels. Once I got the tights on, it turned out they had a nice diamond pattern on them and were pretty see through. And the shoes fit perfectly because I had reasonably small feet for a boy. Jess then kicked me out of her bedroom whilst she got changed. So I left and then spent the time she was taking to get ready, walking up and down in her living room, just trying to get myself used to walking in heels which I think I was pretty good at.

When Jess eventually emerged about 10 minutes later, she looked incredible. She was wearing an emerald green dress that had a slit all the way up to the thigh. The front of the top was also very low cut which meant she was showing a lot of her tits off and it was obvious she wasn’t wearing a bra.

‘So,’ she said. ‘When we’re out we obviously can’t call you Josh because that would give away your secret, so I’ve already text the girls and we’re going to call you Jane.’

We then had multiple selfies taken before we decided to leave. Jess handed me a little clutch bag for my money and phone and then gave me a little denim jacket for the walk to the bar. She then made me text our Mum to let her know that I was going out for drinks with Jess and wouldn’t be coming home tonight. After that, we steadily made our way towards the lift and then walked into Leeds’ gay village ready to start drinking.

We hit the first bar in Leeds where all of Jess’ friends were waiting for us. They all came bouncing over to us, buying us drinks. It’s worth noting as well, that all her friends are extremely attractive, to the point where I’m having to stop myself as best I can from getting a hard on. They were all so nice, they complimented me on how I looked. They kept telling me that they would never have known it was me and what a good job Jess did with the makeup.

After all the compliments, I felt incredible. And as the drinks flowed I really started to forget that I was dressed up and started to relax. The girls dragged me onto the dancefloor and wouldn’t let me leave. They got really hands on and started grabbing at my hips whilst they grinded against my body. A couple of them jokingly started lifting the bottom of my skirt up to my thighs, threatening to expose my panties. And before I knew it, I’d kissed them all. And that caused major problems as my hard on escaped and was now causing an obstruction in my dress.

A few of the girls noticed and laughed. I quickly made my way to the bathroom, I was unsure of which one to go in so I went into the women’s and locked myself into a cubicle and waited for my erection to die down before I eventually got back onto the dancefloor with the girls. The night seemed to pass really quickly and before I knew it, it was after 2am in the morning and we’d pretty much completed every single bar in the Leeds area.

Remarkably, I still felt pretty much sober. I don’t tend to drink much but when I do, I always have quite long breaks in between to stop myself getting to drunk. Nevertheless, I was wandering through Leeds city centre with my heels in one hand whilst I was linking one of the other girls as we escorted them to a taxi to head home. One of Jess’ friends, Sara, was visiting from Manchester so Jess had agreed that she could also spend the night at her apartment and head home in the morning. I was on the sofa anyway so it didn’t really affect my sleeping arrangements.

Sara was a beautiful woman. She was quite tall but I imagine that was more down to the stripper heels she was wearing. Her hair was shoulder length and jet black and she had amazing plump lips. Sara had on a figure hugging outfit, a black top and a pair of skinny jeans which showed off her amazing cleavage and her big round ass. We stumbled our way through the back streets in Leeds before we finally arrived back at Jess’ place and made our way inside.

We were all just chatting in Jess’ room when it was time to start getting ready for bed. I was debating ditching the womens clothes until Jess through me a cami and short set that was made from silk and trimmed in lace. I turned towards the living room to get changed before Jess stopped me.

‘You can get changed in here Jane,’ she said smiling. ‘We’re all girls here.’

So, now I as I looked on, Jess turned her back to Sara and asked her to unzip the back of her dress. Once the zip was undone, it dropped to the floor very quickly before she stepped out of it wearing only a green g-string. Her tits were amazing, they were perky and the perfect size and her nipples were already erect. She then pulled out an oversized t-shirt and put that on before grabbing one for Sara who was starting to undress. She pulled her jeans off first which took some doing because of how tight they were. This revealed she was wearing a bodysuit which disappointingly wasn’t in the shape of a thong. She unclasped the stud fastening and shimmied out of it revealing a matching white lingerie lace set which she then covered with the shirt Jess gave her.

I was the only one who hadn’t changed and I quickly shimmied out of the dress, leaving me in just my tights and lingerie. I had an obvious hard on which caused a couple of wolf whistles from the girls. I could feel my face turning a lovely shade or red as I discarded the tights and pulled on the nightwear set that Jess had given me. Once we were all changed we settled onto Jess’ bed and chatted for a while before I think we all started to feel a bit tired. I could feel my eyes getting heavier so I excused myself to turn the sofa into a bed for the night and get some sleep.

I could still hear the girls laughing and joking for a little while after I’d gone to bed but eventually everything seemed to quieten down and I was soon off to sleep. How long I was asleep for I don’t know but when I woke up and began to stir, my phone was completely dead and I could see it was still dark out. I’m terrible with sleep and even worse when I’m not in my own bed. Once I’m awake, I’m awake and there’s not a lot I can do about it. It didn’t stop me from tossing and turning though and trying to get back to sleep.

‘Oh fuckkkkkk’, I heard as I turned over.

‘Keep going….. yes…. yes….’ In between the noises I could hear a feint slapping sound, that seemed to get louder.

‘Fuck yes….. oh fuckkkkk, don’t stop….. fuck… fuck…. I think I’m gonna cum…’ I turned to face Jess’ bedroom door and noticed that they had left it slightly ajar.

As quietly as I could, I got up from the sofa bed and started sneaking my way over towards the bedroom. The closer I got to the door, the louder the noises got. When I’d finally creeped my way over to the door, the sight that I seen was enough to nearly make me cum in my panties there and then.

Inside the bedroom, they had the bedside lamp on which did a pretty good job of lighting up the whole room. On the bed, toys surrounded both Jess and Sara. And stood at the side of the bed was Jess and she was fucking Sara with some speed. Over and over again she thrust into her as she held her legs up on her shoulders. Sara’s white panties from earlier still dangling on the end of her ankle and her bra had been pulled down, freeing her amazing tits. It looked like Jess still had her panties on from what I could see and had just put the harness on over the top.

I continued to watch, peeking through the door as Jess fucked Sara into oblivion. I must’ve watched her cum numerous times, watching her body shake and convulse from the pleasure as Jess just dominated her. She picked her up and positioned her however she wanted her. Even when Sara begged her to stop, she just kept going forcing her to orgasm over and over again. Yet I stood watching, imagining I was the one getting fucked and not doing the fucking. I couldn’t hold back any longer and pulled my cock from my shorts and panties and began to stroke furiously as I watched the scene in front of me.

It wasn’t long before I brought myself to an orgasm. I pointed my cock back into the panties and blew my load inside of them. I had to use one hand to keep myself upright after my intense orgasm. My panties were completely soaked but I hadn’t left any evidence that I’d seen them which was a good thing. Shortly after my orgasm, Jess finally stopped fucking Sara and collapsed on the bed next to her. The plastic cock between her legs was glistening in the light of the bedroom. They cuddled up together and seemed to drift off into a sleep. That was my cue to make my way back over to the sofa bed and get back to sleep. And sleep I did. Someone did say, you always sleep better when you’ve had an orgasm.

I woke up to the light beaming through the windows in the apartment, then I felt an arm around me followed by my sisters voice, ‘Morning sweetie, did you sleep well?’

I began to stir a bit more, but couldn’t help but enjoy the feeling of being cuddled in the morning. Jess leaned in and kissed me on the side of my face before whispering in my ear, ‘did you enjoy yourself last night?’

My eyes shot open and I quickly tried to come up with an excuse but Jess cut me off every time I tried to speak. She reached around to the front of my shorts and slid her hands inside, feeling my damp and sticky panties which were covered in cum.

‘No need to answer baby bro,’ she told me. ‘I think the evidence is pretty clear.’

She then dry humped me a few times while laughing before getting up and leaving me. As I turned to look at her, I could see her bouncing back into the bedroom with no top on and the cock still dangling between her legs. The thought of my sister fucking me with a strap on had me as hard as a rock again. Just as she was closing the bedroom door she turned to me again, ‘I’ve left your clothes out for you if you want to get ready and changed, and I’ve also left you some clothes if you fancy another day as Jane. There’s makeup stuff in the bathroom.’

I stayed on the sofa bed for a while, contemplating what to do. I checked my phone and looked at myself on the selfie camera. The makeup was everywhere but the wig was still in place. I headed to the bathroom and decided to shower before making a decision. I turned the hot water on and enjoyed a nice long wash. Cleaning the makeup off my face and making sure my hair didn’t get wet was a different experience. But I made sure there was time for a little play, I played with my ass for a few minutes whilst gently stroking my cock bringing myself to the brink of an orgasm a few times before stopping and getting out.

After I’d gotten out the shower, I dried myself off and found the clothes near the sofa bed. On one side, I had my clothes from yesterday with the spare underwear I’d brought. But my eyes were always drawn to the clothes that lay next to them. Jess had left me a cute outfit. There was a denim mini skirt with a cute little Disney princess character top, a headband with flowers on, a scrunchie and then a pink lace bralet with a white pair of panties laid on top.

The more I stood staring at the two outfits, the easier the choice became. I grabbed the panties and bra from the pile and headed back into the bathroom. I slipped the white panties up my shaved legs and tucked my cock the best I could. The panties were super comfy, the thong fitting me perfectly and holding my cock and balls in place. I then slipped the bralet over my head before re-inserting the fillets I’d taken out before showering. I then headed back out into the main room and slipped into the rest out of the outfit including the scrunchie on my wrist and the hairband.

I picked up the makeup and decided to give it a go myself. I grabbed the mirror from the bathroom but couldn’t really see anything when I was sat on the sofa. So I grabbed the mirror and makeup and headed over to the apartment window. I placed the mirror on the window ledge and started applying some eyeliner and blusher. I’d never done this before so I kept it simple and tried not to make myself look completely crazy.

As I was working away, I could see in the reflection of the mirror that the bedroom door had opened and Jess emerged again, dressed in her casuals with joggers and a t-shirt on. ‘Hey sis, it’s good to see you’ve stuck around for another day’, she said when she noticed me by the window.

She slowly walked up towards me and began to speak again, ‘bit of advice though, maybe be a bit more feminine when doing your makeup…. anybody from this side can see what you’re hiding up your skirt.’

I laughed it off, and carried on finishing my make up. Jess continued to make her way towards me and eventually put her hands on my hips when she got behind me.

‘It’s like your teasing me on purpose,’ she said. ‘You keep doing this and I might not be able to resist taking control.’

There was another twitch in my cock at the thought of my sister fucking me with the strap on so I decided to be bold and see how far she would go with this.

‘Take control?’ I said sarcastically, ‘What are you going to do like? It’s not like you’d fuck your own brother.’

‘Wouldn’t I?’ She leaned forward and whispered into my ear and then bit on it gently before sliding her hands down the skirt and then reached up to feel my ass.

I nervously laughed, trying to hide the fact that this was really turning me on. ‘Your all talk’, I said in between laughs. ‘You wouldn’t dare do anything anyway, let alone when Sara is asleep in the next room.’

‘You’re really asking for it aren’t you?’ She let go of my ass and turned towards the bedroom. ‘Don’t you fucking move, I’ll be back in a minute and we’ll see who’s all talk.’

I continued applying my makeup while she was gone and was just applying some lipstick when she emerged from the bedroom once more. I heard her put something on the coffee table and she dragged the footrest across to where I was standing and told me to kneel.

So I climbed onto the footrest with my feet dangling off the end. I used one hand to steady myself against the window ledge and carried on finishing my lipstick with the other. In the reflection of the mirror I could see Jess kneel down behind me and then I felt her hands grabbing at the backs of my legs and I’m sure I felt her nibble on the bottom of my ass.