It was the day before the plane left for South America. The school had organised a one week cruise in the gulf of Mexico for my year, and I think it's fair to say I was slightly over prepared. I had bought new everything and even managed to get some condoms from John, a friend of mine that had some for a long time and offered to sell them, but as it turned out, never thought anyone would buy them. I had never had reason to use them before but my twin sister Cynthia's friends make me so horny I couldn't help it. Cynthia isn't too bad herself but I kept that to my thoughts. The only thing I had left to do was have a few hours sleep before waking up early to get to the airport.
I woke up at 5 when the alarm when off and after wiping sleep from my eyes noticed my morning glory was screaming at me from down under, but today I had to ignore it and have a shower. I put on a T-shirt and joggers with baggy boxers as I wanted to be comfortable for the flight. I arrived at school and went to meet my friends who I could just see in the navy blue morning light, while Cynthia when to find Lucy, her hot best friend. Neither or them were afraid of the cold I noticed, as they both wore miniskirts and tank tops with tight fitting hoodies. "Woooh, Jack your sister is looking bangable as ever" said Jason, grinning at her legs, and I stepped in his way, though I can't disagree. Me and Cynthia went to kiss goodbye to our mum and then got on the bus to the nearest airport, about a 40 minute drive.
At the airport it was pretty quick to get through, and before we were given tickets we were informed that we couldn't swap seats. I couldn't decide if mine was good or bad when I found out I was next to Lucy, but acted cool for the time being. On the plane I felt pretty OK about it, and it was defiantly eye candy for the journey, but as the flight progressed, it became much worse. At first I felt like I should be talking to her, but didn't really know what to say, so tried the confidence trick of imagining everyone in their underwear. That was definitely a mistake. Imagining her but perky tits poking through her bra, and the tight lips of her pussy squeezing her pink panties as she clenched during turbulence. Thats when I realised I had also worn the wrong clothes. My hard on was clearly visible through my loose clothes, and Lucy glanced down a few times as I tried to find a position that hid it, but after a while I realised there was only one way to calm it down, so I went to the toilets to jerk off, and it wasn't long before I came, because I was so hard from the mental image of Lucy naked. The rest of the journey went pretty smoothly after that, which I'm glad for.
After the events on the plane, there was nothing I wanted to do more than relax and talk to my mates, and luckily we were given 2 hours to walk around the town before the boat left. John and Jason decided to go to a nearby cafe and I followed, where we met Charlie and Dan. We sat and talked for a bit about the 2 weeks ahead. Cynthia and Lucy were were sitting on a table on the other side of the room, and kept glancing over at me and giggling. I was pretty sure Lucy knew what happened on the plane and I felt like I should apologise in some way and I prayed that she hadn't told Cynthia about it.
About an hour had passed and I needed a piss, so went to the toilets at the back of the cafe. I opened the door and was surprised to see Lucy coming out of the ladies door. I felt like I should say something, and she was looking at me strangely, so tried to explain. "Hey Lucy" I said awkwardly, "Anything that you saw on the plane was errr..." She smiled at me with her bright green eyes and said " I know, it's fine. I was getting kinda wet looking at you as well". I was fairly shocked after hearing that, but Lucy smiled seductively at me, grabbed me by the shirt and pulled me into the girls toilets and into a cubical.
At this point I had no idea what was going on. Lucy was standing in front of me close up and I had started to get a semi. She looked down at my crotch and saw the growing bulge, but before I had time to react she put her arms around my waist and pulled herself up to me so her skirt was rubbing against it. I got immediately hard and she giggled playfully when she felt it. "I wanna see you cum Jack", she said to my face, "think you can cum for me?" I managed to get out "I almost have already." She smiled at me again and took off her top and bra in one quick movement and I so nearly shot my load then and there. She then bent down and threw off my joggers and boxers. She squealed in delight when my fully erect member popped out and was pointing directly at her face. She put her fingers on the tip and stroked it all the way up and down once. The feeling made me shudder with pleasure and she stood up. She rested her head on my shoulder and began to wank me slowly, getting faster with every stroke. I was in ecstasy and couldn't control my breathing very well. I noticed that with her other hand she had reached behind her and was rubbing her wet clit under her skirt. I put my right hand round to meet hers, meaning to take over from her, but she stopped me and said "I came from fingering myself just before you walked in", so I just put my hand on her arse cheek and felt her hole with my middle finger. She was going fast now and I couldn't help but sigh in pleasure even though I knew I needed to be quiet.
I was close to blowing and told her through my gasps, so she slowed down and crouched again so her head was in line with my shaft. Then she leant forward so it was just touching her lips, but not actually in her mouth, and within a few seconds I shot 5 massive strings of cum on her sexy face. She stood up and leant against me again, and we just stood there for a few minutes breathing heavily. When we had caught our breath and Lucy had cleaned up, I just looked at her and said "Wow. Thanks." She then kissed me awkwardly because we both couldn't stop smiling, and left the cubicle.
I followed her out a while later and talked to everyone on my table for a bit, but wasn't really paying attention to the conversation. Then the bell was rung and everyone. Went to the meeting point and we got ready to board the ship.
Rooms were of two and I was with Jason on the deck that was basically just for the school. Cynthia was with Lucy, and Jason was in the middle of telling me one of his fantasies about my sister, when she walked through the door. "Woooaaah" said Jason, "ever heard of knocking? We could be talking about anything in here"."I have a pretty good idea" replied Cynthia, "The doors at hardly soundproof" which Jason blushed at. "What do you want Cyn?" I said. "actually I wanted to talk to you outside for a bit" she told me. I sighed, stood up, and followed her outside. She closed the door and looked around to see if the hall was empty, then turned and smiled at me. "So" she began "have a nice flight?" All that went through my head was "shiiiiit she knows" but I played it cool and replied "it was okay, how about you?" She checked down the hall again and giggled before continuing "you know, me and Lucy are best friends and she likes you" she raises her eyebrows at me "a lot. So if she thought that you like her too, she would definitely tell me." Yep she knew about the plane, but maybe not the incident in the toilets. "Yeah, so?" I replied, and she explained "well I know any girl would be lucky to have someone with a cock like yours..." she stopped when she saw my expression "come on Jack I'm your sister, I've seen you naked" I glared at her but gestured for her to continue, so she did "besides, no two people take that long in the toilets." Yep she knew about that too, but then she did something I definitely didn't see coming. She cupped my balls with her hand, dragged her fingers up my body until they reached my chin, smiled, and walked away. I opened the door and walked back to my bed in a daze. "what happened?" asked Jason. "I don't know Jase, I really don't know." I replied. "did she get on all fours and ask you to clean her drain pipe?" he asked hopefully. "What?" "Nevermind..."
The next day I woke up before Jason and decided to have an early breakfast then head up to the main deck with the pool to relax. I was wearing shorts and a shirt that I took off to sunbathe, and after a bit Cynthia and Lucy walked through the doors to my right in bikinis and daaaaaamn they looked good. Cynthia stopped and gestured Lucy towards me, then they walked over together. "Hey bro" said my sister "I believe Lucy wants to show you something" Lucy stepped in "yeah its in our room, and I think you might like it" once again I didn't know what to say so smiled and said "ummmm sure, you go ahead, I'll be down in a sec" she smiled and ran back inside. I turned to my sister and said "what are you doing?" she thought for a moment and replied "I think you and Lucy should spend more quality time together" I was still slightly suspicious and asked "was this your idea?" she smiled and said "oh no, Lucy wanted to get you to go further with her all of yesterday, she even made me taste he pussy juice so she could see if it tasted good or not." After being presented with that mental image I was starting to get a hard on, and noticed Cynthia glancing down at my shorts. I needed to get out of there quickly so grabbed my shirt and stood up while she told me the room number and I was about to leave when i said "Cynthia, just one more thing" "yes?" "did it taste good?" she smile turned kinky and she said "oh yeah."
I reached Lucy and Cynthia's room and knocked on the door. Lucy opened it, still in her tight pink bikini and pulled me in. Again she immediately took of her bikini top, and the glorious tits I had only seen once before fell out and were free. I was hard straight away, and took of my shorts to let her see what she was waiting for. She saw my raging boner and asked "Is that for me?" playfully, "all yours" I replied, smiling. She walked backwards over to her bed, but before sitting down she bent over and pulled down the bottom half of her bikini, and even though it didnt seem possible my dick got even harder as her cute, tight and wet pussy was revealed to my eyes for the first time. "Is that what you wanted to show me?" I asked. "Yes" she answered "have you ever heard of the 69?"
This was actually happening. "Now you get to make me cum Jack" squealed Lucy. We were in position with me lying on her bed with her on top of me, her clit just inches from my face, and my cock brushing against her cheek. She kissed the end and I shuddered again, feeling that same immense pleasure surge through me, and I went to work on her cunt as she pecked my dick. I flicked the clit with my tounge a few times, and I heard her gasp with each flick. She then did something that amazed me. With one thrust she put my whole shaft in her mouth and down her throat until my balls hit her nose and she pulled out again. "How did you do that?" I asked "dunno". I decided to step it up a notch too, and used everything I had. I used my right hand to finger her tight asshole slowly, while rubbing her clit with my left hand, and tounge fucking her pussy as fast as I could. I started all this in one go however, and she shook with pleasure and let go of my dick, but after a bit she got more used to it and started sucking me off normally and I could feel her breath on my pubes. I was in heaven, and she gasped "Jack..... I think I'm gonna cum first!" I quickened the pace of everything and sure enough within a few seconds her juces came flowing down onto my face. Cynthia was right, it did taste good. She squealed in delight at the sensation and said she would finish me off, when my sister walked in. "Wooaaah you guys definitely aren't shy. 69, wow looks good. You really are big Jack." By now, Lucy had got off me and was sitting on the bed next to me. Cynthia leant down and whispered something to Lucy, who giggled and said she had promised to finish me off. "Have you tit fucked him?" asked Cynthia, and Lucy shook her head. That was when my sister suggested she finished me off for her. "what?" I said, shocked. "Well" said Cynthia "were both horny, your hard, and I've offered to tit fuck you." I just blinked at her a few times, and she gave me a smile so sexy I couldn't help myself, "if Lucy's fine with it" Lucy gave the thumbs up and my sister took off her bikini top and let her breasts fall. They were even slightly bigger than Lucy's, and then she leant over wrapped them around my still erect dick, and started tit fucking me. I had no idea my sister could cause me so much pleasure, and look so good. After about 30 seconds my cock exploded in her face and over her breasts, so she licked it all off and said "you taste good Jack, I wouldn't mind some more some time." Then she fixed her bikini and left.
Me and Lucy had agreed to let people know we had a thing, but they never would have guessed what kind of thing we actually had. For the next few days we had at least one 69 session a day, although Cynthia didn't give me any more action , she was always around when we doing it, and I think it's fair to say I had life good. Better that I could have imagined.
It was the 6th day of the one week cruise, and it started like most. I woke up late and went to breakfast, then went downstairs to see what Lucy wanted to do. This time though Cynthia was there and they were arguing about something. "No" said Cynthia, after they both greeted me "why not" asked Lucy "you can't do that it's just wrong" answered Cynthia. "What's going on?" I asked, confused. Cynthia glared at Lucy, "nothing"."Well I came to see what you wanted to do today" I said to no one in particular. Lucy smiled and said "probably more swimming", and I smiled too. I liked swimming because Lucy could feel me up under the water. "Cyn, can I talk to Jack alone?" Cynthia did not look pleased about this, but slowly took what she needed and left. I turned to Lucy and raised my eyebrows in anticipation. "Well Jack", she began, "We have a very physical relationship I think is fair to say" I nodded in response, and she continued "well how would you feel, about us.... loosing our virginities together?" I was quite surprised at that, and paused for a moment. Of course I wanted to, but I didn't want her to feel uncomfortable, and I would have to do it right if we did it at all. I said at last "If you want to then yeah, I do" she bit her lip and nodded at me. "When?" I asked. "Tonight", she started "but we can't do it in here" I didn't see why so asked "why not?" and she explained "I don't want your sister interrupting us this time, well just do it when Jason's out"."he usually goes to the bar for an hour at 9 with John, but it's too risky" I said. "I think risks are hot" she smiled sexily at me. I nodded and said OK, and we went swimming.
Me, Lucy and Cynthia were at the deep end of the pool, with our arms over the side looking at the sea. Lucy only had one arm on the side though as with the other one she was slowly rubbing my cock under the water. It was quite an awkward conversation as Cynthia knew what we were planning and wasn't too happy about it, and I wasn't really concentrating because I couldn't stop thinking about what I was going to do. Eventually it was lunch time though so everyone got out and went to the dining hall. I needed a break from talking to the girls, so went to sit at the table with Jason, John and Charlie on. "Good to have you back mate" said Charlie, when I sat down. "Given up trying to find the mysteries of the female mind Jack?" asked John. "Just needed a break from all the talking" I said, and Jason asked "does this mean your coming to the bar tonight then?" and I had to think on the spot "I don't see the point of going to the bar if your not old enough to order drinks" I said. Jason just sighed and said again "coming or not?" I tried to look sad and said "can't tonight sorry", and everyone looked annoyed. Charlie asked what I would do instead, and I made up something about being allowed to sit here but having to talk to Lucy tonight to make up for it, and the rest of the lunch carried on a usual.
Me and Jason went back to our room after that and he pressed me for more information. "So" he began "how far have you got with her?" he asked with an eyebrow raised. "What? None of your business" I said, but he kept going and asked "has she let you touch her tits?" I didn't answer and he said "are they natural?" and without thinking I said a quiet "yes" and he jumped on it with "so you have seen them!" "well..." I began but couldn't come back after that so went with it "yeah but I haven't touched them or anything". He paused for a moment and said "how about her what has she seen of you?" "nothing" I said. I asked what we should do now and he said he didn't care, so I suggested some sun bathing. "You just love taking your shirt off in public don't you", but we went anyway, and the rest of the afternoon was spent on the main deck.
Most people always skipped dinner, and I didn't feel much like eating, so went straight down to my cabin to get ready for what was about to happen. I ate a breath mint, had a shower, changed into some jeans and waited on my bed for something to happen. Then Jason walked in and I realised I shouldn't have got dressed before hand. "What are you dressed up for?" he asked, and I thought on the spot and said "a quiet night in". "OK but don't use my scented candles" he smiled before walking out, dumping a bag in the corner. I waited some more and about 10 minutes later there was a knock at the door, so stood up, walked over there, and opened it. Lucy was standing in front of me in a white, short cut nighty that didn't quite cover the fact that she wasn't wearing panties. She walked in quickly and closed the door behind her, and I hadn't thought about what to say so just asked "ready?" and she nodded and repeated "ready". I then asked, "how are we gonna do this?" Which she smiled at and said "I guess we'll find out" walking over to my bed. I followed and she pushed my backward onto the bed, then took off her nighty, revealing herself completely to me. I had already developed a semi from imagining what we would do, and I got fully hard straight away from her sexy naked body standing in front of me. I pulled down my jeans and underwear just enough so my cock was revealed, which she told me turned her on yesterday, and she walked towards the bed. Lucy was now kneeling naked on my legs, her already wet, virgin pussy inches from my cock, which she was holding in her right hand. It already felt so good just with her hand on it, but it was about to go further then I had ever experienced. She shuffled forward so the head was touching her clit, then let the tip slide in. It felt much tighter then when my tongue was in there, but so much better, and she let as much of it slide in as possible before reaching the barrier that was about to be broken, letting out a long moan of pleasure as she did it. Then she looked at me, and I nodded slowly, so she let her weight slowly bring her down on to my cock, breathing in sharply as it cut through the layer that proved her a virgin, and she kept going until she was resting all her weight on me. I couldn't believe I hadn't came just from that. Her pussy was so tight I could imagine how much it much hurt to her, but I could feel her juices all around my shaft and it felt a strangely natural position to be in. Her eyes were closed when I looked up, but then she opened them and slowly broke out into a smile, and I did too. She began lifting up, and I felt a different sensation as her vagina muscles relaxed slightly, and my dick had space to breathe. Then she went to go down again, but started too quickly and had to stop herself before she reached the bottom, after repeating this a few times she had build up to quite a fast pace considering it was her first time, but her pussy was so wet to start with we didn't need lube. For me it was heaven on Earth, and I savoured every movement Lucy made on top of me. I definitely would have came already if I hadn't done it so many times this week, so I had developed pretty good self control. But quite soon, I could feel that I was going to cum if Lucy kept going, and was about to tell her, but instead this happened: Jason walked through the door.
At first I think we both assumed it was Cynthia, as she often walked in when we were alone, but Jason is much taller and as we turned around it was pretty obvious who it was. At first Jason paused with the door open staring at us, not even much of a look of surprise on his face. He closed his eyes and re opened them, then said softly "wow". He saw me looking at the open door and let it close behind him, and said louder this time "what the fuck is going on?". Lucy had at first looked for a way to hide herself, but realised that getting off me would simply reveal more to Jason. "Hi Jason" I said softly, wondering how he would react, but mainly just cursing inside my head. Jason just nodded with wide eyes as a reply, and I gulped.
Jason was now sitting on his bed, and Lucy had managed to get her nighty back on and I had pulled up my jeans and was facing him. "So you and Lucy were fucking" he said for the forth time, "yes" I said again. "How many times have you done it before?" he changed question, "none" Lucy answered, still obviously shaken from the experience. "Fuck I walked in on a de-flowering, Jesus" he was playing it surprisingly cool, so I explained how it all started and about us and Cynthia, and when I finished, he opened his mouth as if to ask a question, but couldn't decide what to say, so just nodded. A minute or so passed and Jason finally spoke, "Well, now that I know that there's open pussy on the market, I'm gonna want some of my own" which made Lucy look up, eyebrows raised, and Jason quickly said "oh not you" then turned to me, paused, and said "your sister".
Me and Lucy were too put off to finish what we had started last night, but I didn't care that much, at least I can say that I did it, but I imagined Lucy was a bit more upset, and I didn't mention it to her. Walking down the hall to her room after breakfast I realised that it was the last full day of the cruise, which I was sad about. I didn't know what would happen to me and Lucy afterwards, weather we would leave behind what we did here, or carry on just the same. I stopped thinking about that though as I was on a mission, to get my best friend laid. I walked into my sisters room and saw them talking. They said hi to me before continuing, "No way, I was never in it to go as far as you" said Cynthia. I realised that Lucy must have told her about last night, and mentioned that we wanted her to fuck Jason. Lucy stood up and walked over to Cynthia's bed, then whispered something in her ear, before returning to her own bed. Cynthia looked up, obviously thinking hard about what she said, then finally standing up and saying "maybe" then walked out the door, but I definitely saw her winking at me on the way past. I was left alone with Lucy, who looked at me with her sparkling green eyes, and asked "what should we tell him?" and I smiled back and repeated my sisters words, "maybe". We walked out together and back down the hall to my room where Jason was waiting. I found myself thinking about why we were doing this for him, and I suppose it was mainly because he knew about me and Lucy now, and could tell anyone at any time, even though he assured us that he wouldn't. Also because Cynthia quite obviously wanted some male attention too, and when presented with the opportunity I thought she would accept straight away. We reached my door and opened it to reveal Jason sitting on his bed, who looked up when we walked in. He was looking at me with anticipation on his face, and I spoke first, "maybe". His facial expression didn't change and he kept looking at me. Lucy took this as her cue to leave, and when the door shut I walked over to his bed and sat down. "I'm pretty sure it's a yes". His face lit up and he smiled widely, but he didn't need to say anything as I caught a slight bulge appearing through his shorts. He asked me what I wanted to do that day, and we agreed on more sun bathing, so headed upstairs.
We found 2 beds facing the pool and lay down on them. Jason then started asking me questions about sex, like what it felt like, to which I answered "like someones fixing a clamp on your dick" and who I thought was better in bed, but I didn't know what Cynthia was like in bed, so thought for a while, then said "both at the same time", and I could tell Jason was getting hard from imagining that. I told him to stay away from my girlfriend, and the rest of the day past seamlessly. We sat at a table with Charlie and John again for lunch, and I heard most people weren't going to the bar that evening because it was the last night, so Jason didn't need an excuse to get him out of it. Then we found ourselves back in our room waiting for whatever was about to happen, happen. We both had a shower and Jason put on a proper shirt, then we sat on ours beds in silence. Then there was a knock at the door and I looked to Jason who nodded at me, so i went to open the door. Lucy walked in directly followed by Cynthia , both still wearing there bikinis from swimming earlier, and I locked the door behind them.
"Right" Cynthia spoke first, as Lucy came over, sat on my bed and started rubbing my cock through my jeans "if we're gonna do this Jason, we're gonna do it properly" Jason kept staring at her chest. She saw this and immediately took off her bikini top. Jason then made a rather strange noise, like a whimpering dog. I had always thought that Lucy's breasts were bigger then my sister's, but without a bra on, standing up, they looked just as big. She asked Jason, "whats your favourite position?" Jason cleared his throat and said "cowgirl", and Cynthia laughed and said "we're doing doggy" but Jason looked just as happy with that. In the last few seconds I had learnt a lot about my sister, firstly, she had bigger boobs than I thought, secondly, she like doggy, and finally, she can be very dominant. I whispered to Lucy, "should we try doggy?" and she said "let's carry on from where we stopped yesterday". Cynthia said to Jason again "take everything off" Jason paused for a moment and looked over at me, then back to my sisters tits, and nodded, taking off his jeans and boxers, leaving his shirt. His dick was already hard from seeing Cynthia's tits, and I noticed his was slightly shorter than mine, but a bit thicker as well. "Lucy was right then" said Cynthia, and I realised that must have been what Lucy whispered to her. I looked over at Lucy who shrugged and we turned our attention back to what was happening on the other bed.
Cynthia bent down and took Jason's cock in her hand, which made him sigh with pleasure, then she stood up and pulled down her remaining part of bikini. As she bent over to take it off I got a good view of her hole and ,well, she has a nice arse to say the least. I'm surprised Jason didn't cum where he was sitting when he saw her pussy, already slightly wet. She walked over to me and Lucy, and I saw her obviously tight pussy was completely shaven like Lucy's, who handed her a bottle, that she must have carried in. "Where'd you get lube?" I asked her, she smiled at me and just said "woman's best friend". Cynthia squeezed some onto her hand and applied it to herself first, moaning as she did it, then put some on Jason's cock, who gasped at the cold, then leant back on the bed and started breathing heavily as my sister jerked him off to lubricate his cock, and I realised that she did herself first too let Jason's cock calm down or he would have cum as soon as she touched it. When she was done she told Jason to go to the head of the bed and kneel, then she climbed up onto the bed and got on all fours about a foot away from his cock. This was it, I was about to watch my sister and best friend loose their virginity to each other. He shuffled forward a bit and slowly leant into her, with almost his hole head now inside her tight, wet pussy, they both moaned together, but Cynthia's turned into a gasp as he ripped into her insides and popped her cherry, but then back into a moan as he went deeper, until he was leaning all of his weight against her.
I had trouble looking away but it was time for me and Lucy to get it on. She took everything off and I pulled my jeans and boxers to the same place as last time, and saw Jason looking at her, then turning to my cock, then looking away. He was still going quite slowly, but was sweating like crazy and they were both moaning loudly, then I lay back on my bed and Lucy knelt on my thighs again, then reached for the bottle of lube and put some on my shaft. before letting her weight bring her slowly down on to my cock. We both moaned as she did it, and it still felt quite tight around me, but still felt amazing, and again she built up to a steady pace with her hands on my chest. I looked around me and couldn't quite believe that this was happening. A super sexy girl was riding my dick, while my best friend took my sister from behind on the bed over too me. It didn't seem like anything I possibly could have imagined before coming here, but here it was. Jason had built up to quite a steady pace on Cynthia, and gasped "oh fuck i'm gonna cum" and she immediately pulled off Jason, spun around, and wanked his dick hard and fast into her open mouth, where he shot about 5 ropes of cum, then collapsed on his bed. Cynthia said that he needed to finish her off now, so crawled up to him and sat on his face. Jason started eating out my sister's pussy, and I saw he was also fingering her arsehole with his right hand. She was rocking around on top of him and vigorously squeezing her tits, but I turned my attention back to Lucy when she also announced she was about to cum. She went even faster then slowed to a stop as I felt her juices pouring over my cock. Jason looked over at me, wondering how I hadn't gone yet, and I was wondering the same thing, but could feel it coming closer. My sister then announced that she was about to cum, and I said "yep me too". Lucy had got off me by now and was deepthroating my cock, and I came 6 ropes into her mouth, which she swallowed, while I could hear my sister coming at the same time on top of Jason. When I looked over though, Jason's face was soaked, and so was the pillow his head was on. I also learnt that day that my sister can squirt.
Me and Jason fell asleep on the covers when Lucy and Cynthia left, and the next day we just had time to pack and catch the plane home, but this was definitely not the last time we did anything like that, and the relationship between me and Cynthia changed forever.