Babysitting with My Sister Ch. 01: Ewan

"Is it okay?" It was Alex's voice that woke me from the spell. Of course, I knew it was her but it was only when I heard these words that I looked her in the face for the first time. She looked transformed. I am not sure even now if was the alcohol coursing through my bloodstream or the body on show before me but I have never felt more attracted to someone than I did in that moment.

"Do I look stupid?" The confidence in her voice earlier and with which she had stepped out seemed to be wavering.

"No," I croaked.

"You look fucking hot," my sister's voice from beside me, reminding me that she was there.

Alex visibly relaxed a bit at these words.

"Little brother, I know that you are enjoying the view but it is your turn now and you did promise."

I reluctantly stood. "Okay," I said, "where is my outfit?"

"I have left in on the dresser in the closet. It is the only thing not hanging up so you can't miss it."

"Again, you did promise to wear whatever I picked and, well, it is not your usual style but a deal is a deal. And you have to wear the whole thing otherwise it'll look stupid."

"Yeah yeah, I will wear it."

"Great, go and change and we will see you in a few minutes. In the meantime, Alex promised some more wine so we can all have some when you are done."

I stepped forward into the closet, realising once inside just how big it was inside. It was massive, bigger than a lot of rooms I had been in. I walked past the rails of clothes to the end and stopped in front of the dresser. No fucking way.

On the table there were just two things. I picked up the first item. It was a dress. Of course it was. How had I been so stupid to have not even considered that in a house with one girl and one woman, there would be no men's clothes. Well, I thought to myself, I bet that Ellie is expecting me to back down and refuse. Not this time sister, I will show you. I held it up again. It was black, made of a stretchy fabric and, like the others' dresses, appeared extremely short.

Why the hell not, I said to myself as I stripped off what I was wearing down to my boxers, dropping by own clothes into a corner. I have never worn a dress before (despite the hand-me-downs from my sister when I was younger) so it took me a while before I realised that I had to slip it over my head like a jumper. Like a jumper, and unlike the summer dresses that the girls both had on, this one had sleeves so I squeezed my hands and arms through these. They were lacy, tight but long, almost fitting to my wrists. The dress was tight so I had to shimmy it down my naked torso, pulling at the hem. This dress was very short so barely covered by man equipment. Once on, I looked down, almost enjoying the look of my legs protruding from the bottom. There was a problem though -- the length of the garment was shorter than my underwear, meaning that my shorts were showing a good three of four inches below.

It was at this point that I took notice of the other item of clothing that had been left on the dresser. I picked up a pair of black, silk knickers. There was very little to them. Well, better than nothing I reasoned, pulling my own underwear down and off. I briefly enjoyed the feeling of freedom and considered going commando before realising that there was no way I wanted my sister to see what she really should not be seeing. I held out the lady's knickers, stepped into them and pulled them upwards. The waistband was not as big as I was used to so it was tight pulling them over my thighs but they managed to come over and I pulled them all the way up. My penis and balls only just fitted inside them but I will admit, I really liked the feel of the cool silk cradling me and began to feel a little aroused, feeling the slight movement there. I pulled down at the hem again to ensure that I looked decent (well as decent as a teenage boy can look wearing a skin-tight short dress), took a deep breath and walked out of the room, into the main bedroom.

Sitting before me on the bed sat Ellie and Alex. They were nestled together, legs touching. In Alex's hands were two glasses of wine, one full, one a little less. Ellie had her own glass, almost empty already I saw. That would account for the near-glazed expression on her face. Her other hand was behind Alex's back, presumably supporting her.

Any conversation they had been having stopped the second I appeared.

Ellie wolf-whistled her appreciation.

"Wow, I cannot believe that you actually did it," she said.

"I told you this one would look good on him," Alex grinned, "he looks so sexy now."

I thought that I would play along and give them a small show, like Ellie had done for us earlier. I stepped forward, raised my arms outward to the sides and slowly twirled. As my back turned to them, I bent over, pretending to pick something up from the floor to show them my ass in the dress.

"Haha, we can see your sexy knickers" called out Ellie, definitely the drunker of the two of them, almost leary now.

"Dance for us!"

I was enjoying the attention. Again, the alcohol having its effect on my inhibitions, I started to sway in what I thought was an erotic move.

"Not like that," shouted Ellie. "Al, you go and show him how it is done." She practically pushed her from the bed, Alex stumbling slightly as she fought to keep her balance in those high heels. She fell towards me and I instinctively moved forwards and caught her in my arms. She half collapsed into me and wrapped her arms around me for support. I, in return, moved my hands to her torso, resting them at the sides. It was then that I remembered that there was no fabric at the sides, just the strapping containing her flesh. My hands were resting on the skin there, feeling the warmth of her flesh under my palms and fingers.

Now, I mentioned earlier that I had had no actual experience with girls so this was the first time I had ever felt another person like that, it was softer then touching my own skin, certainly fleshier than I had anywhere on my own body. It was amazing.

It was at this point that there was a side effect of this contact. I could feel myself getting hard. The feel of her flesh wasn't exactly helped by the slippery material that had barely contained me even when relaxed. Now, as I began to grow, I could feel myself slide against the silk and this was another new sensation for me, being used to the softness of cotton cradling me. It was such a sexy feeling.

As my fingers moved their way across her flesh and under the strapping holding her in, I felt my cock escape the tiny compact prison that was doing its best to hide it. The only way for it to head was upwards but that meant it was then stretching the fabric of the dress outwards. There was nothing I could do about this at the moment without drawing attention to myself. I didn't need to announce anything though as my sister chose to do this for me.

"Oh my god, is that your penis?"

Alex stepped backwards, my fingers leaving her sides as my sister slid off the bed to her knees in front of me. "It is. Oh my god, my brother has got a hard-on!" She laughed, sounding shocked as if it was something that she could not comprehend.

I looked down my body. Where my flat stomach usually was, you could clearly see the shape of the whole of my cock through the dark, skin-tight dress. It was sticking up vertically. Due to the fabric being so taut over my skin, it was there for all to see.

Ellie was on her knees now, her eyes level with the head, staring at it, seemingly transfixed by the view.

I didn't blame her. In a sober world I would have run off to die of shame but this was a new world of wine and recklessness. And my god, I looked massive in this outfit. I could even make out the bulbous head and the contours where it connected to the foreskin at the underside. I looked, and felt magnificent. I had never felt so big and as I looked down at my sister, kneeling before me I realised also that I could see down the top of her dress. It was made for someone with a fuller chest so with her smaller breasts, there was now enough of a gap for me to be able to see them in full, the nipples prominent on her perky, youthful mounds. I honestly think that with the whole situation and the view before me, I could not be any harder.

It was now that Alex stepped forward again, she no longer had the wine glasses in her hands, having taken the opportunity to put them down somewhere. She knelt next to Ellie, eyes also on the cylindrical shape before her. My eyes drifted from Ellie's chest to look at Alex's. Her breasts appeared to be to opposite of my big sister's. Whereas Ellie's were a perfect B cup (I knew from the bras that I had recently taken an interest in), Alex must have been carrying round Cs, or even Ds. I could not believe that she had always kept these so well hidden under her clothes, but then, I would not have bothered to look before. Now though, all I could see were these two, phenomenal orbs, mashed up against the snug fitting dress that was clearly at least two sizes too small for her.

Alex turned her eyes upwards, locking with mine.

"Does it hurt?" she queried. "It looks like it is being squished."

It didn't hurt, I felt as if it was being worshipped, these two angels kneeling before me.

"Well, these knickers that you chose for me, whilst they feel nice, they are too constricting."

"You poor thing," (I didn't know if she was talking to me or my cock), "let me help."

With that, Alex shuffled forwards, her hands sliding lightly up the outside of my thighs, underneath the dress to the waistband of the knickers. Her fingers slid over the top of them and she started to slowly pull them downwards. As soon as they released their grip on my tightening ball sack, I felt the air rush over me, cooling on the skin there. Alex manoeuvred them over my thighs and downwards, allowing me to step out of them. I felt partially free again.

As she had leant forward to reach me, her head had moved to within an inch or two of my groin. She now sat back again, level with Ellie who had been watching this with interest. I could not believe that here I was, in a dress with nothing underneath it with these two girls at my feet. I should have been nervous but not a trace of fear crossed my mind.

There was silence in the room now, no-one wanting to break it. I didn't want this to end but did not know what to do next. Alex had an idea though.

"I want to see it. I have never seen one in real life and I think that you want to free it."

In fact, I was actually loving this whole wearing a dress thing. It was such a slim fit, showing off my slim body and the shape of me, as well as the freedom of going commando. I felt sexy as hell.

"I think that you need to show her Ewan," Ellie chimed in. "When else is she ever going to get the chance again to see a dick? And I think she will love yours."

This was a good point.

"But as I am your sister, I don't think that it would be right for me to look." I could see on Ellie's face that whilst she said these words out loud, her eyes were still studying the way my cock was straining against the black cotton. I made it twitch a couple of times to see what reaction I would get. They both smiled at this movement. I really wanted to show off in front of my audience but as drunk as I felt at this precise moment, even I knew that she was right.

"It is up to you Ellie; you don't have to see what your brother has been hiding from you all this time." My right hand raised up and I gently touched the front of the dress where it was doing a poor job of shielding my man-parts, slowly running the tips of my fingers from the base to the tip. There was the slightest sign of the darker wet spot there, a sign my precum was seeping through. This focused both sets of eyes on the spot. I felt like such a tease and was loving it.

"No Ewan, I am not going to look as it will change everything between us."

With that she managed to pull herself to her feet. I presumed that she would either tell me to stop this show or walk out of the room. Instead, she sat back on the bed, falling backwards to lie down, facing up at the ceiling.

"Everything is spinning, I think that I will just lie here for a while."

I looked at her body, spread out there. Her hands were by her side, her legs spread. In her condition, she was not aware enough to even think of closing them so I was rewarded with a clear view of those brilliant white knickers that she had taken from Debbie. I thought that I could see a wet area staining them but without moving closer I was not sure. If I was the sort of freaky person who would take advantage of a drunk girl, I knew that I could probably finally get to see exactly what I had been sharing a room with for all these years.

"I am not your sister, and I will see your cock tonight whether you want me to or not," Alex stated, very matter-of-factly.

I was more than ready to show her everything she wanted. I reached down, ready to lift the hem up and pull out my member but Alex stopped me with a shake of her head.

She moved forward slightly, her face again just an inch or two from me. Her hands reached around my thighs, gripping the backs of them. I tensed fractionally, moving forward as a reaction. With just this slightest of movements, it brought me to where her mouth was waiting. I felt her gently kiss my dick, about half way up the rigid pole, still standing to attention.

Fucking hell, I could have exploded then and there. Alex looked up then, and I noticed just how large her hazel eyes were. Looking into my eyes as if to check that this was allowed, her tongue poked out from between those lips. Those lips that had kissed me on my cock! She then proceeded to touch her tongue to the base of me, very slowly dragging it upwards, as if tasting the world's longest ice cream. I could see the trail of spit that she left, glistening on the dark fabric. As the tip of her surprisingly pointed tongue left the very top of its run, I felt her the nails on her fingers dig into the inner fleshiness of the tops of my legs, parting them slightly.

"Show me. Now." Whilst whispered, I knew that this was a command I could not disobey.

I reached my hand under the dress, moving it upwards. I gripped the thickness of my hard cock and, leaning it slightly to the side, forced it downwards under the hem and up again, allowing it to finally point out directly in front of me. I was still holding it, enjoying the feel of the throbbing in my fingers and palm. It was pointing straight at Alex's face and due to its length, she had pulled her head back slightly to avoid it hitting her.

As if it had a mind of its own (muscle memory), my hand instinctively started to move the skin back and forwards, a slow wank. I knew that this action would end this too soon but it was a habit.

Alex watched me do this for a few seconds. I then felt her left hand cover my right one there and she joined the movement, backwards and forwards. I loosened my grip and slid my hand from under hers. She didn't miss a beat, continuing this handjob exactly as I had been doing it. Her face was still lined up with the hole at the font of the head and she very quickly leaned in, her tongue flicking out for a split second to lap up the glistening drop of my precum, so fast I barely had time to register it.

This was a moment I had been waiting for since I hit puberty. Someone else was touching my cock, the first time since I had been bathed by my mum as a child. And they weren't just touching it, they were wanking it, this hand slowly and firmly moving its warm, tight grip forwards and backwards along the full length, the foreskin covering the head before being drawn back and taught as this soft hand pulled all the way back, fingers brushing against my balls.

Alex kept this same pace for what seemed like an age but what I knew was probably no more than a minute or two at the most. She was studying the movement and apparently every inch of my dick as she moved her hand, before swapping to her right. I realised that I was barely breathing, so lost in the sensations that were coursing through my entire body.

"This is beautiful, so hard and yet soft at the same time. I can feel it almost burning in my hand. I can feel ridges in my grip as my hand slides over your dick. Is this okay?"

I could barely speak, I whimpered what I hoped she would understand meant yes. My hands lifted slightly, my fingers lightly touching the top of her head. Looking back, I am sure that many boys would want her to give a blowjob but at that moment, I couldn't think of anything other than "Don't stop, don't you ever fucking stop!"

Her head moved closer still, turning slightly not to use her mouth but to lay the large, now red head of my cock against her cheek, the softness there feeling cooler and silky smooth against the tenderness of my bellend. She turned slightly and now kissed the tip one more time, her lips sliding along the side where her hand had been a moment before.

"Mmmm, I love the feel of you between my lips, so smooth and hot." I could feel the breath ever so slightly from her lips. I felt the tip of her tongue on my shaft, following the movement of her hand, her open lips ever so lightly running above and below it.

I was watching this, as she was watching her own actions, not wanting to miss a thing. Her left hand found its way back to my inner thigh, the tips of fingers dragging lightly upwards, until they made contact with the underside of my balls. I assumed that she would cup me there, as I often did when I pleasured myself but instead, I felt the tickling sensation as they so gently caressed me between my legs, tiny circles, moving back and forth in time with her wanking right hand. As she pulled the skin back hard, I felt the tip of her middle finger brush against my asshole, feeling it's way around the rim, pausing at the entrance. This was something that I had never even considered before, adding a whole new level of nervous anticipation.

She was the boss of me.

"Cum for me, I want to see you cum." I barely heard the words but even without them, I knew that it would happen any second. I could feel the familiar tightness in my balls begin, and the tremble start from my toes and work its way upwards to the centre of my legs. Alex still did not change the speed or tightness of her grip as she slowly worked me. I started to tense all over, even my fingers becoming hard as they gripped her hair. She took this moment to slip that middle finger inside me, just a tiny bit but it was like nothing I had ever felt before, this alien object inserted in my virgin ass.

It was the final straw and as the feeling hit me, I automatically thrust forward into Alex's hand a final time, her grip forcing the skin back as far as it would go and I cried out as I came. My head flew back and I felt myself shoot my cum with more power than I ever thought possible. I shot load after load, not caring where it was going, just never wanting this to end.

I was gripping Alex's head tightly now, squeezing it as the convulsions took over my body.

After what seemed like an age, I slowly became aware of Alex's hand moving again, now much slower, a looser grip as she seemed to be trying to milk every last drop from me. I felt her finger exit my hole and instantly felt the cool air replace it

I also loosened my fingers, just keeping them nestled in her hair. I looked down, expecting to see the creamy-white spunk either all over Alex, or on the floor behind her. She looked clean, apart from the last few drops that had probably just dripped onto her exposed shoulder as she extracted the last of it.

"That was better than I ever thought it would be" she said up at me, a grin on her face.

I couldn't have agreed more and would have said so, had I the strength left to tell her. I nodded and I hoped that she understood that I needed a minute or two.