Sisters Know Everything

'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.