Taking a Vacation with my Sister

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Prize holiday brings already close siblings closer.
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Part 1 of the 3 part series

Updated 06/07/2023
Created 02/01/2015
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This is another attempt at writing from the male perspective.

All comments welcome.

*****

I am 19 years old, still live at home when not at University and am currently single. Typical family, mum, dad and a sister with a pet dog. Since we moved into a larger house when I was 14 I have had my own room, which saved me from having to share with my sister. She is 18 years old and there is only a very little age gap between us, less than a year.

We are very close, sharing a room until early teens kind of demands you get on, and it helps if you friends, which luckily we are. We had fallings out, all siblings do, but on the whole we were more like best friends than brother and sister.

When we shared a room we tried to respect each other privacy, we were both at that awkward age of development, but accidents happen and I had seen her naked and she had seen me. She has since developed into a very attractive young lady, very petite body, barely 5 foot tall, long brown hair to around her elbow in length, she wore size 8 clothing with a 30A size bra, not that I checked. I am a little over 6 foot, short cropped light brown hair, I am no gym fanatic but I have some muscle definition and if I really really tense there is the startings of a 6 pack.

It is a strange thing when you share a room for so long, and then you suddenly have privacy, lonely is the wrong word as you don't get lonely, it is just, well, it is just weird. Being able to walk around naked and not bother, waking up with morning horn and being able to sort it, those sorts of things. I also found myself spying on her, which sounds a lot worse than it was, it was an innocent teen peeking through the crack in the door if she didn't close it properly and very occasionally catching a glimpse of her in her underwear.

I was fairly sure that she did it to me as well, hovering shadows outside the room if I didn't close the door properly, I am not 100% sure if she did or not and I didn't broach the subject, but I am fairly certain that she had peaked at me at least two or three times. We still spoke about everything and we had very few secrets, I knew she was a lot more sexually active than I was, I had had sex twice, and both times had been enjoyable for me, arguably a bit short for the lucky lady. She had a long term boyfriend for a little over a year which from what I could gather she went around at weekends and just spent 48 hours with her legs open, not that I was jealous.

That sounds a bit weird, jealous of my sister having sex. Do all brothers fantasise about their sister? I don't know, it isn't the sort of subject that comes up in the pub, my mates have described in detail what they would like to do to her, but I just did the whole "leave her alone she is my sister" stance. I could appreciate that she was a very attractive girl and if she wasn't my sister then yeah, I would probably want a bit, but she was my sister and doing anything with her was a fantasy at best, and at worst illegal.

This is a story about how fantasy became reality, and to quote from the above, "I got a bit."

It all started one standard rainy English summers day when I got a letter through the post. I opened it and it was tickets and notification that I had won a weeks all inclusive holiday in Barbados for two people. Great, I was single and I was considering not bothering when my sister came down and saw the letter and asked who I was taking. I said I didn't really know and before I knew we were going together and it was next week.

It was a good job we got on as planes don't tend to be all that large, and it isn't a short flight. It had not escaped my attention that the dress that she was wearing was a thin strap at the top and when she fell asleep on my shoulder her hunched position gave me an unhindered view straight down her dress. Couldn't really see anything due to the angle, but could see the tops of her boobs and when she shifted her self a bit I was sure I caught a glimpse of a nipple. I stopped myself staring and woke her up when the food was brought around. She would never forgive me if she missed out on food.

I almost asked if she had a bra on, but there was no way I could ask without sounding like a perv, so I just left it. After the meal, which was typical plane meal, okay, but that is all, she fell asleep again. This time she shifted around in the seat to sit with her back to me, her legs curled up beneath her. She sank down a bit which allowed me to see over her head which was resting on the top of my arm and see straight down her top. She was indeed not wearing a bra, and I was sat staring at my sisters tits down her top. I just stared for a couple of seconds before looking away and going back to my kindle.

She was cute, and every time she moved I had another peak at her unobstructed breasts. It was a shallow angle so couldn't really see much, they were on show though to me, no one else could see. She moved again, this time her dress folded down the middle holding it a bit further off her body, not much more, but enough to allow me to see right the way down it to where her legs tucked beneath her body. I now knew that she had panties on, and I knew that they were a light green in colour.

I again stared for a few moments and felt a stir in my pants as my penis stiffened slightly. Shifting it so as to hide my erection I looked up and caught eye contact with the elderly chap sat opposite us in the isle. He looked at me and smiled before glancing down and just stared again. I thought for a second he had spotted my hard on, then wondered if he had seen me staring at my sisters boobs, but I quickly worked out that he was looking up her dress.

I shifted my arm waking her up, "Eh what?" she said sleepily.

"Sorry," I whispered, "but you need a longer dress to sleep like that."

"Oh hehehe," she laughed sitting up properly sweeping her hand under her bum to cover her modesty.

She looked across the isle and the chap smiled at her before going back to his book, the woman next to him, his wife I assume was fast asleep, unaware that her husband had been perving on a girl at least a third, probably closer to a quarter, of his age. She put her head on my shoulder again and said quietly, "Thanks."

"No probs," I said.

"Old guy?" she asked quietly so no one else could hear.

"Eh?" I said.

"Who was looking?" she clarified.

"Oh, yeah," I said, "Prob made his day."

"Prob made his life, crinkly old pervy fucker," she said almost silently as she giggled.

I felt a pang of guilt as I was no better, in fact I was worse, I had been viewing her boobs for the last 30 mins and saw her panties as well, I only woke her up when a random was checking her out. "Least I had some on," she said.

"Some what?" I asked being taken by surprise by her statement.

"Panties," she said still dozing on my shoulder.

"Would be a brave girl to go without in that dress," I said looking at her legs where her dress stopped a good 6 inches above her knees.

She just smiled and dozed on my shoulder for a while as I tried to move as little as possible as I glanced down between my legs. I was rock hard and could feel my cock straining against my shorts resulting in a noticeable lump. I unfastened the tray and lowered it down, placing my kindle on it and sliding it forwards to cover me up. After a few minutes she leant forwards and got her kindle out of her bag.

The plane eventually landed and we collected our bags. A chauffeur was waiting for us with our name on the iPad, very posh, and took our bags as we followed. He opened the door to a blacked out perfectly clean black Mercedes and allowed us to get in before placing our bags in the boot and getting into the drivers seat.

He drove us to the hotel and escorted us to the reception as a porter unloaded our bags and disappeared with them. We checked in and went up to our room which was a suite on the top floor. Our bags were waiting for us, the air con was set at 20 degrees, a large bathroom was immediately to the right as you went in with a separate area at the side of it for changing which was partitioned off from the rest of the room. The bedroom was dominated by a large super-king size bed in the middle of it, a 50 inch TV was on the wall which was situated so it was viewable from the bed or from the sofa to the far end of the room. Double balcony doors opened up onto a large balcony with two chairs and a table with two sun loungers as well all set-up. There was also a bottle of bubbly and two glasses on the desk along with the usual hotel info packs.

"Wow," Fi said, "this must be worth loads."

"Fairly good isn't it," I replied looking around the room. I was used to Travelodges and Best Westerns, not that there is anything wrong with them, but this was very luxurious.

"Understatement of the century," she replied smiling at me.

I had noticed that there was only one bed, and the sofa wasn't a sofa bed, "Erm," I said pointing at the bed.

"What?" she replied looking at the bed I was pointing at.

"One bed," I said.

"Oh yeah, didn't even notice," she replied, "Guess you are sleeping with your sister," she added with a cheeky grin.

"That okay?" I asked.

"Look at the size of it," she said gesturing towards the bed, "I am sure we can cope."

"Want me to go and see if they have a spare bed?" I asked.

"I am fine with sharing," she said, "what do you normally wear?"

"Erm," I said taken by surprise by her question as I normally slept naked, "Erm, nothing usually, but will wear boxers. What about you?" I replied.

"Normally just undies," she replied.

"Bra?" I asked looking at her.

"No," she said looking at me, "Topless, but will wear a vest or something."

"Okay, if you change your mind let me know," I said.

"Will do. What time is it?" she asked.

"Erm, just gone half 2," I replied, "pool for a few hours?"

"Yeah, sounds good," she replied.

I got my shorts out of the case and went to the bathroom to change leaving her in the room. I closed the bathroom door and waited for a few seconds. I considered giving it a couple of minutes then trying to catch her naked, but talked myself out of it. She probably would just laugh it off, but it may cause us to fall out, and on day one that would be annoying to say the least. It never crossed my mind that it was maybe a little wrong to try and get a peak of her in the nude.

I stripped naked, my penis was still not entirely relaxed, and in a couple of strokes I was hard again. I stroked my hand up and down it a couple of times before kneeling down and having a wank. I didn't last long, the image of her only wearing her panties, the thought of her sleeping topless and just the picture in my mind of her petite pert little breasts was enough. I cleaned up, put some shorts on and opened the bathroom door.

"Ya decent?" I asked.

"Erm, yeah," she shouted back.

I went back into the bedroom and smiled at her, she was wearing a bikini, which was effectively just her underwear and she wasn't bothered. I suppose me wearing just swimming shorts was the equivalent, but it still felt a bit weird. She was wearing a black bikini, the top was a thin string behind her back and the same around her neck. The one around her neck was tied, the one behind her back she was just finishing off tieing. The cups neatly covered her breasts, the coverage was minimal, yet full, if that makes sense. She wasn't exposed, but was barely covered, designed for sun bathing I assume to reduce white bits.

The bottoms were full back, the front again neatly covering her privates. They were neatly tied at the sides in bows and I did wonder if they were double knotted, I assumed they were, but not really that relevant. She was applying sun cream to her tummy and sides before she handed me the sun cream. "Do my back will you?" she asked turning away from me.

"Erm yeah," I said squeezing out some of the cream. I applied the cream to her, making sure I got all of her back. She did my back and we headed off to the pool.

There was plenty of space at the pool so we selected two sunbeds in the sun and settled down. After a while she got up and said that she was going to get into the pool. I just nodded as I read my book, but I did glance above it to watch her get into the water. She swam around for a while before going to the shallow end and just laying on the slope you use to get in and out. Her bikini top broke the surface of the water in time with the lapping waves, the material shining in the bright sunlight off the wet material.

She got out and wrapped herself in a towel and sat next to me. Once she had dried in the sun she wrapped the skirt around her again, not that it covered anything, then we headed off to get some food which was a burger and a pint for me, she had a glass of wine. I had a few pints as she finished a bottle of wine before heading back up to the room.

"Drink?" I asked holding the wine above a glass.

"Please," she said smiling, "Will just got for a quick shower."

"K, will go after you," I said.

I poured her a glass of wine before opening a bottle of the local beer for me. It was the same make as the pints and was fairly nice. I sat on the balcony and just watched the scenery. Not much was happening, the street below was fairly busy but while sat down I was too high to be able to see it, and beyond that was the beach and the sea.

"You going for a shower now?" I heard her ask as she poked her head around the corner of the bathroom.

"Yeah," I said standing up.

She came out of the bathroom wrapped in a towel as girls do. She was petite, but damn, it was a short towel, she was covered, but barely, if I had stayed sat down I reckon I would have been able to see if she was wearing panties or not, and I suspect that she wasn't.

"What?" she asked as I was obviously staring.

"Sorry," I said, "that is one hell of a short towel."

"Yeah I know," she said shifting uneasily, "Only two though so didn't wanna leave you without one."

"Very kind of you," I said, "You wearing any..."

"No," she interrupted me as she held the hem of the towel down, "So keep your eyes north you perv."

I just smiled at her and went into the bathroom. I closed the door and unfastened my shorts. Checking in the mirror I needed a shave, so I opened the bathroom door, "Ya decent?" I asked.

"No," she said, a tone of panic in her voice.

I stopped opening the door and waited until she was she was okay. I went out and grabbed my razor out of my travel bag. I looked at her and she was stood on the other side of the bed, clutching the bed sheets under her chin to cover herself up. What she hadn't noticed was the balcony door was acting as an almost perfect mirror and I could clearly see her naked back and bum in the reflection.

I just smiled at her, unsure what to say, or whether to say anything as I stared passed her eyeing up her reflection. Her delicate sides curves into her waist before curving out ever so slightly into her hips then down her slender legs. Her delicate back ran perfectly into her flat bum. I did notice that her legs looked really long when she was naked. Her shoulder blades were protruding out slightly as she gripped the sheets which were covering her modesty, at least at the front anyway.

"Good job you didn't just walk out then," she said.

I just looked at her and didn't reply, although I did look at her eyes instead of her bum in the reflection. "Naked," she said.

"I know, can see you in the reflection," I said grinning at her and pointing before heading back into the bathroom.

I showered and wrapped a towel around me before going back into the room. She was sat on the balcony wearing a t-shirt and I assumed some sort of underwear. I got some boxers out of the case and stepped into them. I pulled them up under the towel, releasing the towel and simultaneously pulling them up the last bit. I did notice that she watched as I did it, maybe she was hoping to catch a glimpse as well.

I didn't bother with a top, I went out to join her on the balcony wearing just my shorts. She just smiled at me, so I smiled back. "Stupid bitch," I said playfully.

"Cant believe I did that," she said, "What could you see?"

"Well it was acting like a mirror, so erm..." I said.

"Oops," she said shyly and blushing a little.

"We all have an arse," I said, "Coulda been worse."

"Yeah true," she said, "If you had just walked out you would have got the full monty."

"Damn," I said smiling at her, "Wish I had now."

"Perv," she said playfully, "Was just like panic panic oh my god oh my god nothing covered."

"And then you stood in front of what was effectively a mirror in your birthday suit," I mocked.

"Oh well," she said laughing it off, "Drink?" she asked as she picked her glass up.

"Yeah please," I said handing her the empty bottle.

I will admit that I did look as she stood up, the t-shirt was short, barely long enough to cover her bum, yet she managed to stand up without showing what she had on under it expertly. I guess it is years of practise wearing skirts and having pervy blokes hoping for a glance every time you move.

She handed me another bottle and sat down again tucking her legs underneath herself and pulling the t-shirt down between her knees. "So how is the sex life?" she asked.

"Shit," I said bluntly, "Yours?"

"Yeah same," she said taking a sip of her drink, "How long has it been?" she asked with a mischievous glint in her eye.

"Erm," I said as I worked it out, "6 months."

"Six months?" she quizzed, "Steph not put out?"

Steph was my last girlfriend and we split a couple of months ago after a short relationship. We never got to the sex stage. "Nope, ended fairly quickly," I answered.

"What happened?" she asked.

"Just didn't get on, one of those people that just annoy you for some reason," I replied.

"Fair enough," she said, "Didn't even get a blow job off her?"

"Nope," I said.

"Hand job?" she asked.

"Nope," I replied, "Never had a BJ."

"Really!?" she asked sounding surprised.

"Yeah, Donna didn't do that and she is my first and only," I admitted.

"Did you go down on her?" she asked.

"No she didn't like it," I said.

"Crazy bitch, awesome feeling once he finds the target," she said with a grin.

"Target?" I asked sounding confused.

"Tongue on clit, two fingers inside," she said looking at me, "Ooo yeah."

I just smiled at her, having this sort of conversation wearing only boxers was a bad idea, yet it didn't stop me asking how long it had been for her.

"Couple of months," she said, "Since we split up."

"What happened?" I asked.

"He was a bit of a dick," she replied.

"Isn't that the idea?" I said smiling at her.

"A lot of a dick would have been better in that department," she said with a cheeky grin.

"Do you suck?" I asked after a moments hesitation, partly because I could feel my cock waking up, but mainly because I wasn't sure if I should be asking that question or if I wanted the answer.

"Yeah," she said with a slight tone of shyness.

"Swallow?" I asked grinning at her.

"Hahaha, perv" she laughed, "Yeah swallow, less mess, I would just end up sleeping in it anyway if I didn't. As I said, bit of a dick."

"What does it taste like?" I asked genuinely quite intrigued.

"The old chiche," she said, "Salty with the consistency of snotty eggs."

"Sounds lovely," I said screwing my nose up.

"Give to receive," she said, "I cant expect licky if I don't give a bit of sucky."

"True," I said looking at her. She looked so sexy sat on the chair, her modesty only covered by a t-shirt, her legs that were bare pretty much from the top were curled beneath her as she sipped her drink between talking. "Do you take it up the bum?" I asked glancing at her shyly. I surprised myself with the question, mouth engaged before brain and I just asked it straight out.