A Family Holiday

“You are a very naughty girl!” I whispered to her, as we splashed about in the pool. “You can’t go around giving me a hard-on with our parents around! What if they saw us?”

“Ooh, so it’s not “don’t do it,” it’s “don’t let anyone see,” is it?” she laughed at me. “You’re just as bad as me! You shouldn’t have been gawping at my body, should you? Well if you can tease me with your words, I can tease you too!”

I couldn’t argue. I was enjoying every minute of our little game, even though I knew it was a dangerous one to play. Nothing wrong with a bid of holiday escapism, I thought, and my sister certainly seemed a lot brighter and happier today.

“Joe, would you put some suntan oil on my back, please?” Ann called to me a little later. She was lying face down on one of the big loungers, and I was sitting reading a book. I walked over to her, and picked up the bottle of oil from her side. Perching on the edge of the sun bed, I poured a little oil into my hand and drizzled a little more directly onto her back. She gasped as the cold oil touched her hot skin. I quickly placed my hands on her back, gently but firmly massaging her shoulders and down her arms, before returning to the middle of her back. “Mmm, that’s nice,” she murmured. “Can you do my legs, too?”

Pouring a little more oil, I sat further down the bed and reached over to massage the backs of her legs. She shifted a little on the bed, and as my hands moved up from calves to thighs, her legs parted just a little. I moved my slippery hands down again, then up, each time noting her thighs moving further apart. My hands moved further up too, and I found my thumbs spreading her arse out a little with each push. She was breathing deeply and evenly, loving my attention. I chanced a little more contact, my finger trailing lightly over her swim suit, down the crack of her arse and smoothly over her pussy. She shuddered slightly – had I gone too far? But the next time my hand moved between her legs she closed them tightly around it, keeping my fingers there, for just a couple of seconds. “Thank you, Joe,” she whispered, “don’t think I’ll burn now for a bit.”

Looking carefully over at the rest of the family, I squeezed her arse cheek firmly once, and got up to dive straight into the pool. I needed to cool off!

The rest of the day passed slowly, as we all unwound from the stresses of our everyday lives. Mum and dad seemed to sleep most of the time, while Ann, Beth, Paul and I read books and jumped in the pool when it got too hot. Ann was careful not to get too close to me, and I didn’t push it at all. Later in the evening, we all walked down into the town for some food, and found an Italian restaurant right on the beach, which served excellent seafood washed down with cold white wine. Back at the apartment, Beth and Paul disappeared to bed, whilst dad fixed a nightcap for the rest of us. Ann said she was going to bed, and I sat on the terrace sipping a small whiskey with my dad. Perhaps our game was over.

When I slipped into the bedroom, I assumed Ann was asleep. I went to the bathroom, took off all my clothes and walked back to the bed, quietly easing myself under the sheet. It was a bit of a surprise when Ann spoke: “Hey, you.”

“Oh, Ann, sorry, I didn’t mean to wake you up.”

“You didn’t, I wasn’t asleep. How’s it going with you then?”

“Okay, cool,” I said. “It’s been a nice evening, good food, good company. You alright?”

“Yeah, think so. Missing Jamie a bit, I guess. Not sure what I’m doing here really. But yeah, I’m doing okay.”

There was something in her voice telling me she wasn’t telling the whole truth. “You sure, Ann,” I said, “you sound a bit unhappy.”

She sniffed. Was she crying? “Hey, Annie, don’t cry,” I said, sitting upright in bed. “I’m sure Jamie’s cool, he’s being well looked after, and you should be using this time for yourself, it’s great to get away from things for a while.”

She was crying. I slid my legs over the edge of the bed, and knelt down beside her bed. Reaching up, I stroked her hair back from her face, down to her neck. “It’ll be okay, honest! Relax and enjoy your week. You’ll be able to put everything into perspective when you get home, but for now don’t think about it too much.”

Ann wriggled her arms free and placed them around my neck and shoulders. “You’re just so bloody reasonable sometimes!” she smiled. “Give us a hug.”

I eased my arm under her head, and kissed her gently on the top of her head. My right arm slid down her back over the sheet, and I squeezed her gently. I could have stayed kneeling beside her bed for ages, but Ann was pulling me up towards her. I ended up half sitting and half lying on the edge of the bed, and Ann rolled onto her back and pulled me down next to her. “A proper hug,” she demanded, rolling over more so she had her back to me now. I moved so I was facing the same way as her and put my arm around her side. She wriggled slightly against me. “That’s better,” she whispered. “You sleep well. Think I will like this.”

I kissed the back of her head. “Sleep well, sis, sleep well.” She was nearly asleep, her breathing slow and regular. I breathed in the scent of her hair, tired too but all too aware that I was naked, and that although there was a sheet separating us my penis would be pressing into her back if I moved an inch or two. I moved away from her slightly, and drifted gently off to sleep.

Chapter 4

I woke up with a start. Where was I? Who was this with me? What time was it? It was still pitch black outside, and I just about made out the time on the fluorescent digital clock on the table. 3:38. My penis throbbed – had I been dreaming again? I still had an arm around Ann’s side, palm resting flat on her stomach, although the sheet was separating us too. I moved my arm slowly down to rest on her hip, adjusting my position slightly so that my cock wouldn’t bump her too much. My arm travelled down the outline of her leg. She was definitely naked too, I couldn’t feel any knickers. I stretched my arm as far as it would go, trailing my fingers back up her leg, over her hip and up her side, to where I could feel the swell of her breast. Slowly, almost dreamily, I stroked down and under her breasts, cupping one gently in my hand, and then down onto her stomach again.

My sister sighed. Oh god, was she awake? My hand froze on her flat belly, and I listened carefully to Ann’s breathing. Same as normal, slow and regular, she was still asleep. I breathed out, a sigh of relief, and my hand continued its slow exploration of her body. I traced the same pattern as before, down her leg, up again and up to her breast, gently stroking and back down to her stomach. The next cycle I varied slightly, rather than over her hip on the way back up I trailed my hand lightly over her buttocks, running a finger over her crack, before carrying on up her side. I felt so horny, this delicate, teasing stroking was fantastic. The next cycle I lightly rubbed the front of her breast – her nipples were tight and erect as I brushed over them. I hoped my sister was having a beautiful, sexy dream, which is what I felt I was in the middle of. Trailing my hand down her front, I reached round further than before to stroke over her pussy and down the front of her legs this time.

Up I went again, a little firmer over her arse now, and brushing my cock too. I was nearly coming, this was one of the most erotic feelings I’d ever had. My fingertip traced slow circles around her nipples, one after the other, and then up further for the first time, gently across her neck and then back down her side. This time I grasped my penis firmly, and pulled on it a couple of times, edging myself closer to the inevitable eruption, but not yet – I wanted this to last as long as possible. I rubbed the small of Ann’s back, and pushed my hand down onto her arse, one finger exploring around her tight hole, and then further down. Were her legs further apart than before? They had to have been, I hadn’t been able to brush across her cunt the last time. I ran my hand back up her front, and across her tits. Her breathing was deeper now – had I woken her? I didn’t think so, but I wasn’t sure I cared any more, I needed to touch her, needed the physical relief. My hand slid back down her front, and I pulled her leg back towards me, pushing my cock into her arse crack. I reached round and put my hand straight over the mound of her pussy, feeling the rough hairs, and held myself against her as my cock twitched, once, twice, spitting it’s seed into the sheet that was all that separated us. Oh that felt good!

I eased my hand away from her pussy, and my sticky cock away from her arse. How was her breathing? Yes, normal, I was sure I hadn’t woken her. My beautiful sister. I slowly turned onto my back, exhaling as I recovered from my orgasm. It just felt right to be in bed with her, although I had to wonder what she would have thought had she been awake. Was I using her body, abusing her even? I guess I was, but we had both got into this game together, and it felt good to play it. I had to be careful, though. She’d find the evidence on the sheet later, so I had to play it a bit cool, pretend I’d just had an erotic dream if she asked. The thought played on my mind as I drifted back to sleep.

Chapter 5

Ann woke me in the morning with a gentle kiss on my cheek. “Hey, sleepy,” she whispered. “You should probably get into your bed just in case anybody comes in.” It was a fair point, and I slid reluctantly away from her warm body. A few minutes later mum knocked on the door, and called us for breakfast once more. “Did you sleep well?” Ann asked me as she got up and went to the bathroom.

“Mmm, yes, it was nice and warm cuddling you,” I said, and got up to put my swimming shorts on.

“I had a really naughty dream,” Ann said as she came back into the room. “You were holding me and stroking my body, getting me very turned on. Oh, you were a very naughty boy in my dream!”

I laughed. “Well that would be bad, wouldn’t it. A nice hug, you asked for, and that’s it. You are my sister, after all!”

“Well it was only a dream, wasn’t it? Can’t help what you dream about.”

She was looking at me hard now. Did she know? Was it a dream she’d been having? I looked away. “Hey,” she said, “don’t be embarrassed, it was lovely. Very erotic, just being separated by that thin sheet.”

Oh shit! “Ah, sis, I’m sorry. I thought you were asleep, I just woke up and felt so horny, and you felt so nice against me, and, I guess I got carried away. Look, I’m sorry.”

She walked up to where I was sitting on the edge of my bed, leaned over and kissed me, lightly, on the lips. “No embarrassment, no saying sorry. I loved it, your touch was so gentle, so caring. Haven’t felt like that in a long time. I wanted to let you know I was awake, but I just couldn’t, I didn’t want it to stop. So no saying sorry, eh?” Another kiss. “Come on, breakfast. Mum’ll be wondering where we’ve got to.” I felt so guilty, but Ann was buoyant, beaming a huge smile at me. I stood up and followed her out onto the terrace.

“What’s everyone up to today, then?” my dad asked as we ate our toast and drunk orange juice under the clear blue sky.

Ann was the first to reply. “I think I’m going to go into town and have a look around the shops. Might buy myself some clothes. Beth, do you fancy coming?”

Beth said that she’d love to. I looked over at Paul – it was pretty clear that he didn’t fancy shopping at all, so I suggested that we could go down to the beach and try out some of the activities down there, jet skis being my favourite. Paul visibly brightened at this idea, and it was settled. The girls went off to get changed, and, after giving Ann a few minutes I went to pick up a towel and my beach shoes.

Ann was sitting on her bed, wearing a short light blue dress, and combing her hair. “Would you like to take me out to dinner, tonight?” she said, looking up at me as I walked into the bedroom.

I was slightly taken aback. “Er, yeah, great, that’d be nice, sis, yeah.”

“Excellent!” she said, flashing me her biggest grin. “Being taken out by a handsome young man – I can’t wait!” She squeezed my arm and gave me a peck on the cheek as she left the room to go and find Beth.

Paul and I had a cool morning, messing about at the beach. I’d always got on reasonably with him, but this was the first time we’d spent together without Beth around, and I found him to be just like my younger sister, bright and funny, confident, generous. The time passed quickly, and we decided to go for a bite to eat and a beer in one of the seafront bars before heading back up to the apartment for a siesta. The girls hadn’t returned from their shopping trip by the time we got back, and I went straight to the cool of the bedroom, lay down, and was sound asleep in minutes.

Chapter 6

Beth was sitting on my bed, shaking my arm gently to wake me. “Come on Joe, I hear you’ve got a hot date this evening.” I blinked a couple of times, and sat up. “I think it’s really nice that you told Ann you were taking her out to dinner. She could do with cheering up, I think. Hopefully a bit of retail therapy earlier has helped, but it’ll be good for her to have a nice meal and a bottle of wine too. Where are you going to take her?”

I looked over to the clock. 6.42. God, had I been asleep that long? “Er, not sure, Beth,” I mumbled. “Did you have a good shopping expedition then?”

“Yes, excellent!” she smiled. “Ann’s bought a new dress and had a haircut, I got some lovely tops – there’s more shops in this place than in London!”

Her enthusiasm had woken me from my slumber. “So I guess I should be getting ready then.”

“Oh, yes, sorry,” Beth replied. “Ann’s in my room, so I’ll leave you to it and see you later.”

I quickly jumped in the shower, and had a shave. I selected a pair of faded blue jeans and my favourite white t-shirt, brushed my teeth and was up on the terrace with a beer in fifteen minutes. It was about ten minutes later when I heard footsteps coming up the stairs. I turned round to greet Ann, and just had to stand and stare – she looked fantastic! Her long, light brown hair was now short and blonde, and she was wearing a figure hugging dark blue dress which came down to just above her knees. I couldn’t ever remember her wearing makeup before, but she’d obviously been borrowing from Beth, and her face had a beautiful glow. Her eyes were shining brightly as she strolled over to where I was standing. “Wow!” was all I could manage, “you look beautiful, sis.”

“Okay, none of this “sis” business tonight,” she said. “I want you to treat me like we’re on a proper date, a couple who’ve only met a few times before. I need a bit of practise at this sort of thing for when I get back home again. Is that alright? But thanks for the compliment, anyway!”

“Yeah, sure, Ann,” I wondered about what the rules were for the evening. “Do you have anywhere in mind for dinner?”

“Well I noticed a nice looking seafood restaurant near the beach earlier, and I thought you might like to take me for a drink in that bar just further along from the jet skis before that.”

It all sounded great to me. I formally offered Ann my arm, and she placed her arm through mine as we left the apartment to cries of “Have a nice time” and “Don’t be too late” from the others.

We walked slowly into town in silence, enjoying the peaceful early evening and the last of the sunset, and settled at a table on the terrace, gentle waves lapping rolling up within a few feet of us. She did look beautiful, her eyes especially were something else – there was a sparkle there in the candlelight which I’d never noticed before. “I love your new haircut, Ann, really suits you. And that dress – it looks fabulous on you. I’m very proud to take you out to dinner tonight.”

I swear she was blushing a little. “I’m glad you like it, Joe,” she said quietly, “I want to look good and I haven’t always bothered in the past. Does it make a difference to how people see me, do you think?”

“Well I guess so. I mean, now there’s no way anyone would treat you as a mother as opposed to as a sexy woman, I think the haircut is more modern, makes you look younger. You know what I’ve said before about your body, and the dress really shows it off. You’re gorgeous, and I hope you know it too!”

“I feel different to normal, you know, sexier, maybe younger. Less worn down, anyway. And I think that’s a lot to do with self-esteem. And you’ve really helped me by telling me that you like the way I look, really. So thank you.”

Our drinks arrived, and we sipped in a comfortable silence. The bay was tranquil at this time of night, the first stars starting to shine and reflect off the black sea. “I think I need to be loved,” Ann broke the silence. “I haven’t been with a man for over two years now, and you start to think it’s never going to happen again, do you see?”

“Yes, I suppose. It’s easy to get into a rut, and when you do it’s tough to get out of it again. But I don’t ever want to think of you being unhappy, you deserve all the happiness in the world. You’re a beautiful person as well as having a beautiful body!”

It was a corny line but I think I got away with it – Ann was laughing. “Is that what you say to all the girls?”

“Well, some I suppose. But only the ones I like!”

Dinner was really good, a very simple meal of fresh seafood served on another terrace overlooking the sea. The highlight was probably when a young Spanish guy came in selling roses – he stood by the table and asked me if I’d like one “for your beautiful wife,” which made Ann laugh out loud. The rose seller apologised, and asked if I’d like one “for your beautiful girlfriend,” with a smile. Of course I bought one, and presented it to her with a gentle kiss on the cheek.

“There,” I said, “he obviously thought we were the perfect couple.”

“Rubbish, it’s just a sales line, bet he says that to everyone.” But I could tell she was secretly pleased, and stretched my feet out to squeeze her leg between mine. She smiled sweetly at me across the table.

It had been a lovely evening. When we got back to the apartment everyone else was in bed, and I went to open our bedroom door too. “Ah, no,” Ann stopped me. “We’re on an early date, so you should just give me a goodnight kiss and leave me at my door.” And then, almost as an afterthought, “you can come in in ten minutes.”

I bent to kiss her on the lips, and she kissed me back gently. I pushed my lips a little harder against hers, trying to open her mouth with mine, but she pushed me away laughing. “Boys, boys,” she smiled, “always after one thing. But I’m not the sort of girl to put out on a first date. Good night.” I was left standing there as she closed the door gently on me.

After the required ten minutes, I softly opened the door and slid into the room, which was in total darkness. Quietly undressing, I got into bed and lay down, listening for my sister’s breathing. After the previous night I couldn’t tell if she was sleeping or not, but she was certainly peaceful. I turned onto my side to face towards her, and it wasn’t long before I was dozing off.

I was woken in the night by the sound of my bedsheet being pulled down and Ann getting into bed next to me. “Shhh,” she whispered, “don’t wake up. Just needed a hug, that’s all.” She snuggled up to my back, placing an arm across my chest and lightly kissing my shoulder. Her tits were pressing on my back, and although I was still half asleep I could feel my erection growing. How was I supposed to get back to sleep now? But somehow she seemed to have managed to, her soft breath even on my neck and her hand totally relaxed across my stomach. I didn’t dare to try and wake her or touch her, and eventually must have drifted off again.

Chapter 7

“Morning, sexy boy.” She was whispering in my ear, and it was a lovely way to wake up. “Come on, I want a swim before breakfast.” Ann was up out of bed and rummaging in the cupboard. She came up with a bikini and sat back down on the bed next to me. “I bought this yesterday too,” she said, “hope you like it as well.”