Babysitting with My Sister Ch. 01: Ewan

I would like to thank volunteer Always_Jinx who helped me as an editor.

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EWAN:

When I was younger, I always wanted to be a babysitter. My older sister wanted the same thing. I didn't know how old we had to be to look after anyone else, only that it was always teenagers that had the fun. Needless to say, for years (it seemed to me) I nagged my mum, telling her that I would be great at the job but I was never trusted enough.

Fast forward a few years.

I am now a teenager myself, just turned 18 six weeks ago, and haven't really given much thought to my earlier dreams in a long time, having found other books and other interests. I have school friends now and my sister and I don't really play detectives anymore; we are too mature for that. In fact, we hardly even see each other during the day let alone have any fun together, too busy with our own mates. I don't really know what she does with them -- girly things no doubt.

Let me explain. Ellie is 16 months older than me (and doesn't she like to keep reminding be of that fact), in the year above me at school. I have never really felt like the "little one" that I recall, as we were always about the same height. It was partly for this reason that we are often mistaken for twins. We currently share the same blonde hair (hers a little longer) and blue eyes, slim bodies and pretty faces, or so we are often told.

Now you wouldn't think that this was a problem but let me tell you why this sometimes annoys me. The main difference between Ellie and me is a penis. Mine. Yes, I am her brother.

Our family was never exactly well-off so we have always had to make do. Never a problem, it was just how life was. We shared a bedroom for the first part of our lives. As I said, we don't really have much money and a larger house is not an option. Mum had her room and we had the other. It was quite large and at least we had our own beds.

Recently, our mum has divided our room into two small ones. I know that we both appreciate the wall mum had put in, giving us at last some privacy (although very small rooms with just a single bed, wardrobe and a desk each). Annoyingly (for both of us) I have to walk through her half to get to mine.

I know what you are thinking. Here I am, a hormone riddled teenager sharing a house with a hot blonde girl, about to tell you about all the sexual things we do after bedtime but you are wrong. It was never that sort of relationship.

Of course, you will think that I am lying if I say that I am oblivious to the presence of a teenage girl so close to me all the time, but she is just not on my radar in that way.

Even though we have perfected our routines over our lifetime to ensure that we do not get changed in front of one another (surprisingly easy with practice), I have recently begun to find myself enjoying the small glimpses of naked flesh that she sometimes let slip.

For example: I was surprised recently when one evening, having dressed after a shower, I had gotten into my boxers and the usual old T-shirt for bed as always, I opened the door to Ellie's room to see my sister sitting at her desk with nothing covering her top half. She had her back to me whilst brushing her hair. I stopped in the doorway, knowing that I should back out and leave her but I was captivated. Just being able to see the pale, smooth skin of her back in full, the defined muscles of her shoulders as she held her hair up with one hand, brushing with the other. As her body moved slightly, twisting with the strokes of the brush, I could just make out the side of her breast, the rounded curvature. I was frozen, my mouth dry, not breathing as I didn't want to miss any further movement that might reveal a little more.

"What the fuck are you doing, you perv?"

Shit. I realised that the reason she was brushing her hair there is because that is where the mirror was. She would have seen me open the door and known exactly how long I had been standing there.

"I am ready for bed," I mumbled "I thought that you would be too."

"I will be in two more minutes" she snapped.

I backed out, visibly blushing but not sure if was because I had been caught or because this was the first time that I realised that my sister had tits. Of course, I already knew that she had breasts but not TITS. It wasn't as if they had appeared overnight from nowhere but as I saw her every day, I had just not given it any thought. She was just "Ellie."

Five minutes later, I knocked on the door.

"Come on in," she answered.

She smiled as I entered.

"Sorry I snapped at you, it's my fault I took too long tonight."

I shrugged, "I was just about to ask if I could borrow a charger."

"It seemed to take you a long time to find those words" she laughed.

I laughed too, wished her goodnight as I walked across her room to my own door.

"Sweet dreams" replied Ellie.

I laid awake for a little while, thinking about what I had seen. It was then I realised that as people, we have certainly changed, the two of us, and that I would never think of her as just my big sis after that.

I also realised how stupid I was. If she had seen me in the mirror, I would have been able to see her. All of her. What an idiot I was! I fell asleep and definitely had very sweet dreams that night.

This incident was never discussed and we have just carried on our day to day lives as before, me with school and my friends, she with her uni mates. I was very careful from then to give her space and certainly enough time to get herself ready whenever she needs it.

At night though, I did find it harder to get to sleep knowing that there was a fully formed woman in a bed just a few feet away, separated only by two inches of drywall.

After reading my book, I often put my paperback away and settle down, wide awake. I just lie on my side, facing the wall between us, allowing my mind to dream:

I imagine the look of concentration on her pretty face as her eyes follow the words on the pages. I pretend that there is no wall between us, that I can just stare at her chest without her knowing, the side view demonstrating the perkiness of her breasts, despite the lack of bra. I know that she doesn't wear one to bed.

I swear that I can just make out the contour of a nipple sometimes as we pass each other in the hallway, but this is probably just wishful thinking.

I picture her body leaning forward to her turning out the light as to do so, she has to lean and stretch, causing the material of her pyjama top to strain against the bosom.

I thanked God for my imagination. I will then lie awake, thinking through every detail. I used to listen for the sound of her gentle light snores before I could relax fully, helping me doze off.

Again, this is not a story about all the lewd and potentially illegal thoughts that race through my adolescent mind, as much as it could be. No. That is possibly for another time.

Getting back to the "babysitting". It was late in the afternoon on a Thursday two weeks ago. I had finished all my homework after school and was ready to just lie on by bed and immerse myself in a new book. Yes, I could have been chatting with mates online but I do like the simple pleasures sometimes.

I heard the phone ring downstairs, followed by the sound of my mum's voice as she picked up. I didn't really care enough to try and listen to what she was saying, it was probably just the usual boring adult stuff anyway and I needed to get my head down and crack on with my novel.

After a few minutes had passed, I became aware of a figure in the doorway. I glanced up to see my mum standing there.

"Well, you have finally got your wish after all these years."

Of course, I had no idea what she was talking about.

"Debbie just called," she continued. Her mum has had a fall and she needs to go and help her, make sure that she is alright in that house on her own, check that she has all she needs until she is feeling better."

"Okay..." I still had no idea what business this was of mine. I was intrigued when I heard Debbie's name though. Debbie was one of our neighbours. She lived opposite and a couple of houses over. As I had hit puberty and started looking at women as more than just the opposite sex, she had featured in my fantasies many times.

Debbie was a mum of one, a daughter my age called Alex. I had known Alex for as long as I could remember but didn't really care for her much. She was in my year at school and whilst we used to play as little kids, we now barely spoke to each other, maybe an occasional "hi" in the corridors of school but nothing more. She was a girl and I was a boy - different worlds now.

Her mum though, wow. Debbie was about the same age as my mum but they could not have been more opposite. Whereas my mum was just a mum, wearing mum clothes over her mum figure and doing mum things, Debbie was a MILF.

Tall. Long black hair with a slight wave to it. Dark brown eyes, always with a hint of eye liner to accentuate the eastern European look to her. Darker skin than me, not just tanned but naturally so. Slim physique, definitely someone who worked out to keep every ounce of fat off her. Very toned with an amazingly flat stomach. I knew this because she went for a run every evening and I would often go out of my way to find things to do at the front of our house at that time. She ran wearing figure hugging shorts and always a sports crop top.

I was amazed the first time I noticed her stomach; it was almost a six pack and this was not something I had realised that real life women had. Granted, I didn't really get to see many women's bellies but I had seen Ellie's over the years and whilst it was youthfully flat, it was not toned.

Of course, above Debbie's abs were a pair of perfect breasts. They were not big although I couldn't swear to this as they were always very contained, but there was definitely enough to still bounce as she ran. I knew exactly where to stand to maximise my view of this phenomenon approaching me whenever I was lucky enough to catch her out the front.

She was always polite, giving me a wave as she flew past, her hair in a long ponytail, earbuds in.

And as much as I love her at the start of her runs, I was in heaven if I was lucky enough to see her on the way back. If it was a long run, she would jog past me on her return, all hot and sweaty by this time. Usually, it was just a sheen of sweat that would glisten on her face, neck and of course that stomach but sometimes (after what I guess was a particularly hard session), she would be soaked, the sweat dripping down her chest, her top dark with the moisture. I particularly loved it when she wore light grey sweats as this would show up the wetness clearly, I could see the wetness around her crotch as well as the patches all over her lithe body. I liked to imagine that I could make her that wet, our hot, sweaty bodies slipping and sliding against each other. As she would go past me, I would watch her from behind, her perfect ass cheeks moving with each stride, that wet darkness running from the waistband, down the crack. God, I wanted to fuck her so much.

I would often take time afterwards to go shower. I would stand under the hot water, imagining that she was doing exactly the same thing at the same time. I would imagine her soaping herself as I would soap myself, wishing that it was Debbie's hands rubbing the shower gel all over my throbbing cock as I wanked myself off, using the lubrication of the soap. I could sense her, standing behind me, her boobs squished against my back as she reached around my tensed stomach. I could practically feel her hard nipples making dents in my skin, as my hand worked faster and faster until I came, spraying the shower door again and again.

One day, I kept promising myself, one day.

I used to shower a lot.

Back to my mum, at my door.

"As you know, Debbie doesn't drive so I have offered to take her to her mum's. She is really worried and asked that we leave as soon as possible. As I have no other plans, I told her we can leave in about half an hour, as I just need to pack an overnight bag."

"Okay...and?" I wondered again where this was going. Did Ellie and I have to go with her to take Debbie and Alex hundreds of miles north? Whilst I liked the idea of missing school tomorrow, I didn't really want to be stuck in a car with Alex for the hours it would take. As I said, we were not exactly besties.

She must have seen the look of dismay on my face. "Alex has school tomorrow, as well as you and Ellie. Debbie doesn't want to take her out of her lessons. She might be away for a few days and have a lot to be getting on with and Alex cannot really afford to miss any learning."

This was part of the reason that Alex and I did not really see each other. I was just a normal, average Joe. I kept my head down at school, got on with my work and did okay. Ellie was the same as me (as far as I knew). Alex however, was not like us. She certainly needed to work.

Alex was not exactly academic. She was in the bottom sets for every class. She wasn't a stupid girl; it was just that learning did not come easy to her. She had few friends, seeming to prefer her own company. She didn't exactly stand out, she was just, there. You know that some people are memorable and some aren't.

If you were to ask anyone in our school in 5 years' time to describe her, I guarantee that you would receive the answer "Who?" an awful lot.

I could never really put my finger on why she wasn't popular. She wasn't one of the fat girls. She wasn't one of the skinny ones. She wasn't ugly but certainly not hot (like her mum). She was average height, average build, average size tits (probably, I had never even glanced at them). She didn't dress like a slut, or like a frump. Alex was, and is, average. And there is nothing wrong with that, she just held no interest for me.

"Anyway," my mum continued, "You know that I trust you and Ellie alone at home alone. Whereas Debbie is worried that Alex is not mature enough to stay alone. Let alone get ready for school on her own. I have offered your babysitting skills, just as you always wanted."

"So, you want her to come over here for the evening?" I groaned. I suppose Ellie could look after her.

"Not exactly. As their house is bigger than ours, I suggested that you and Ellie could stay with her for a day or so. You know, just to make sure she is okay. They have a bigger TV and more to do there anyway. It'll be like going to a hotel."

"You are joking, right?" I never thought all those years ago that my first babysitting role would be to look after a teenage girl, practically the same age as me.

Mum looked pained. "I am so sorry, but it really is the safest thing for the three of you. Besides, you used to be friends."

I could see that mum was too nice and clearly did not want to let Debbie down. I could understand this and knew that she didn't really have any other options. And as a teenage boy who loves his mum, what else could I do?

"Sure mum, but you can break it to Ellie when she gets home."

Turns out that this was just a few minutes later. Ellie seemed as thrilled as me, but when mum pointed out that as she was the elder of us, she would be in charge, she brightened up slightly and said yes.

It only took mum a few minutes to get her bag packed. In that time, Ellie and I just threw a few things in an old suitcase that had not been touched for a long time. For me, it was school uniform for tomorrow (as a Friday), shorts and a couple of old T-shirts, some toiletries and a couple of books to relieve the boredom. Ellie grabbed a few bits and pieces from her side of the room and threw them on top, zipping it up. We never really got to go on holidays or stay anywhere else often so I figured that this was all we would need for a short "trip". We could always pop home if we needed anything else, it was just over the road after all.

We dragged the case downstairs just as the doorbell rang. I rushed to answer it as I knew who it would be. I opened the door to find Debbie standing there, a bag over her shoulder and a suitcase by her side. She looked good, really good. I had just a few seconds to soak in the sight before me: Hair loose and flowing over bare shoulders. A black and white sundress that was held up only by the tautness of the material straining against her boobs. It was short, stopping just below the crotch, her olive-skinned legs flowing down to the flip flops on her perfect feet. As that moment, all I wanted to do was offer to go with them in the car, if only to watch the way the short dress would ride up over her toned thighs as she relaxed into the passenger seat of our vehicle.

"Here are my babysitting heroes."

She stepped in and gave me a hug. I could have died a very happy man at that moment. Or, more likely, cum in my pants as I felt her hands reach around me and her breasts squish just very briefly against my chest before releasing me and moving to my sister. She hugged her as well for a second longer than me, thanking her for helping out at such short notice.

Mum appeared. "No problem," she said, "they are happy to help out a neighbour in distress."

Debbie looked between Ellie and me.

"You are both growing up so fast, so mature already."

I stood a bit straighter.

"I know it seems odd that I need someone to look after Alex at her age, but she has never been left alone at night before. I would just feel better knowing that you are all together. Safety in numbers and all that!"

The next few minutes were a mad blur. Ellie and I grabbed a last few things, mum getting her keys and hurrying us out of the door, locking it behind her. I carried her bag to the car, kicking myself that I had not been quick enough to offer to take Debbie's as well. Ellie carried that for her. I pulled our case behind me.

We stopped at the road, loading the tiny amount of luggage into our old family car. Debbie passed Ellie some cash "to buy some nice takeaway and treat ourselves" and just like that, they were gone. Ellie and I stood on the path, hugs and goodbyes over, waving as they pulled away.

I looked at her, a little excited at the thought of being without adults for a few days, even if I was to be stuck with two girls. Ellie looked back at me, smiled and crossed the road. I followed behind, still pulling our half full case with me.

We reached the front door and knocked. A few moments later, it opened to reveal the girl we were going to be "babysitting" for the next day or so.

With a scowl on her face, Alex invited us into her domain.

"I don't know why my mum thinks that I need you two to look after me. It's not as if I am a kid. Hell, you are the same age as me!" she said, focussing her eyes on me. I was actually a month or two younger than her, but didn't feel that this was the time to mention it.

"Hey, it is not something we wanted either Al," said Ellie, "but here we all are. Who knows, we might be able to catch up and actually have some fun together."

There was a silence that followed, broken by Alex. "You can bring your stuff upstairs. Ellie, you are in mum's room. Ewan, you have the spare room next to mine. Unless you both want to bunk up together..."

We knew that this was just a dig at us and the fact that we once shared a room at home.

"No thanks," smiled Ellie, ignoring the jibe. "I am looking forward to sleeping in peace and quiet. Also, I like to sleep naked!"

My jaw dropped. Ellie walked to the doorway of Debbie's room, passed through it. I watched as she jumped on the large, king-sized bed, a long sigh of contentment falling from her lips.

"Yep, I could get used to this."

I was still thinking about the idea of Ellie sleeping with nothing on, maybe I should suggest bunking up after all.

"Well, I can sleep in the nude as well" I countered.