It was the summer of 2016 I had just graduated from high school and was currently sitting in the airport waiting for my flight to Hawaii. Our graduating class had organized a trip to an all inclusive resort just West of Honolulu. I was elated to hear our flight get called
"Oceanic flight 815 bound for Honolulu, Hawaii. we are beginning boarding at this time please form a line in a calm orderly fashion." My friends and I waited for the line to die down before we went to line up
"I'm trying to stay drunk the entire time were there" one of my friends, Oscar said. He was a brown haired wanna be hick who lived in town.
"fuck ya" my other friend Liam chipped in. Once the line died down we got up and got in line. I was distracted since this was my first time flying and I had been looking forward to this trip for a while. I should probably tell you about myself. My name is Connor, I'm 5'9, black hair, basically no muscles, kind of shy (until I got to know you). I passed all of my classes with an 80% average which is good considering I never studied or did homework (seriously how did I pass). My life in high school was mediocre I never went to parties (except for the prom after party). I rarely went out with friends, I mostly stayed home eating ice cream and watching Netflix. I had never dated during high school and I still have yet to kiss someone much less have sex with them. Speaking of which my Cock is a nice 6 inches it's nothing to impress the ladies but it's good. Anyways back to the story.
"Have a nice flight sir" the boarding attendant chimed, Bringing me back from my trance
"Thank you" I replied. I walked up the walkway onto the plane, as I was making my way down the aisle to me seat my eyes wandered the seats looking for Megan. She had been my crush since Grade 9, I had spent many a nights jacking off to her Facebook pictures. After scanning the plane I couldn't find her, I thought I must have just missed her. As I reached my seat I threw my carry on into the upper compartment and took my seat. After sitting for ten or so minutes I saw Megan walking down the aisle, she stopped at my row and threw her stuff in the compartment. I was so joyful, I mean my crush might be sitting near me. Megan then looked at me
"Hey Connor! are you 23c"she asked in her beautiful voice
"Yep 23c"
"Cool I'm 23d"
"Nice" I barely squeaked out , my long time crush was sitting next to me on the 10hr flight I was so happy.
"Ughhh what's taking so long" Megan groaned. We had been in the air for about 30 minutes and the food cart still had yet to come down the aisle
"It's coming, it's still in first class" I replied
"Screw them I am way more important" she said sarcastically. we both laughed
"So Megan are you excited?"
"Hell yeah I am, I get a whole week of partying in the sun. Why aren't you?"
"Yeah I'm excited why wouldn't I be"
"I guess you should be excited. You get to look at me in a bikini all week"
"I wish I could see you without a bikini" is what I thought to say but I kept it to myself "what? No, I'm excited for the unlimited booze"
"Ohh come on you can't at least thing about everyone in a bikini"
"Well as much as Oscar in a bikini turns me on"
"I didn't mean everyone" she said rolling her eyes "don't you want to see the girls in a bikini?"
"Ummmm"
"Hello, what would you guys like to drink?" I let out a breath since I really didn't want to talk about girls in bikinis with my crush.
After we finished our drinks Megan dosed off and I followed quick behind. I woke up to turbulence some time later. It took me a second to realize where I was since I had been having a wonderful dream about Donald Trump and some bunnies and exploding chilli, it was pretty average for my dreams. I felt a weight on my shoulder and turned my head to see what it was but all I got was a eyeful of beautiful blonde hair. It took me a second to relive Megan's head was leaning on my shoulder. I was debating whether or not to wake her up eventually I realized I couldn't fall asleep so I turned on my phone to watch a couple episodes of the X-Files. After 3 or 4 episode the flight attendant tapped me on the shoulder
"Sorry sir, you need to turn off your device we're going to be landing soon" I started switching off my phone and folding up my headphones "ohh and can you please wake up your girlfriend".
I got a little turned on thinking that the flight attendants thought we were a couple. I tapped Megan on the shoulder lightly then when she didn't wake up I shook her harder
"Ughh, you could be a little nicer waking me up" she groaned
"Sorry, but you wouldn't wake up. Plus the flight attendant told me to wake you up"
"Ohh how sweet of you" she said in a mocking tone
The plane began to descend and both of us looked out the window to get a glimpse of Hawaii
Once we landed I met up with my friends and we picked up our luggage and went to find our bus to take us to the resort. Once we were on the bus my friends and I started talking
"Dude I heard there's 108 kids coming" Liam said
"Fuck that's a lot of busses" I commented our bus began moving shortly afterwards. I was looking out the window or talking to my friends the entire ride. There wasn't much to see it was mostly beaches and forest. After an hours drive we finally reached our resort much to the cheers of everyone aboard the bus. We got our stuff off the bus and we started heading towards our rooms, since the trip was organized by an outside entity there were separate buildings for each gender. The building me and my friend were staying at was building 4, Liam and I were room 15 whilst Oscar and Dylan were in room 16. The room was nice it had a washroom with a shower, Jacuzzi and toilet right off of the main door. Behind that were two double beds, and a tv along with a living room area and a balcony with a view out to the magnificent pool.
"This is nice" Liam commented as he reached into the fridge to grab a beer " you want one?"
"Sure why not" he then threw me a beer and I chugged it down in a few sips.
"Want to head down to the beach today" I asked
"Sure we have nothing else planned"
"I'll call Oscar and Dylan". After I finished calling them we all went down to the beach where we spent the next two hours before we went to the buffet for supper. After stuffing ourselves we went back to the room to go to sleep
"See you guys tomorrow" I yelled slightly drunk as we went into our room I immediately passed out on the bed.
I awoke the next morning with a raging morning wood and debated whether or not to jack off, since I was in a confined space with somebody else, I decided against it. After a while I hawed some rustling from the other bed
"Pssttt, hey Connor, you awake?"
"Yeah I'm up"
"Good I'm starving". I looked over at the clock to see what time it was I realized that it was 8:30am. After 10 minutes of groaning about having to get out of bed I finally crawled out and shuffled over to the shower. Turning it on I got out of my pyjamas (basically a tank top and boxers) and got inside. I love the feeling of being naked and living with two siblings (both I would push in front of a bus in a heartbeat) I couldn't really walk around nude at all, except for the odd time. As I felt the water flowing down my skin washing away the dirt and grime from the previous day my hands slowly reached towards my now erect dick. I slowly began stroking it taking in the feeling of having my hand engulf my cock, imagining that my hand was Megan's mouth wrapping around my... Knock* Knock* Knock*
"Connor I'm leaving for breakfast soon are you almost done"
"Uhhh y-yeah I'm al-almost done" I stammered out breaking the pleasure. I hurriedly washed my hair, turned off the shower, dried off, and threw on some clothes
"Connor, hurry up I'm starving"
"I'm coming" I grabbed my sunglasses and ran out the door. Even though it was only 9:00 it was still hot out and since we're from Canada we weren't used to the heat.
"Goddamn it's hot out" Oscar said
"It will only get hotter" I pipped in since I had gotten used to the temperature already and knew the general layout of the resort
"Yeah the girls will be hotter" he said back highfiving Dylan. When we finally got to breakfast and took a seat I ordered an omelet and everyone else ordered bacon and eggs
"Hey Connor look who just walked in" Oscar whispered I turned my head and saw the beautiful blonde hair of Megan
"Why don't you go over there and talk to her" Liam said nudging me.
"Come on Connor she's even sitting alone"
"Why can't you guys leave me alone" I said
"Cause it's fun" everyone chipped back. "Come on Connor you're never getting laid like that"
"Fine I'll go sit with her!" I said as I pushed back my chair, grabbed my food and walked over to her table.
"Is this seat taken?" I asked
"No you can have it" she said as she looked up at me with those pretty blue eyes. I pulled the chair out and sat down
"Why are you sitting alone, where's Camryn and Brianna?" I asked
"Oh I slept in and they left without me"
"Well that wasn't very nice"
"Yeah" she said as we both chuckled. As her food arrived we stayed mostly silent except for the odd question about school. As she finishing up her hash browns she looked up at me and said
"Hey, do you want to hang out today at the pool?"
"Sure why not" I replied staying calm on the outside but screaming with delight on the inside.
"Great lets go". We wandered back to her room
"Can you wait outside while I get changed?" She asked
"Sure" I answered. I stood outside knowing that Megan was nude inside. After about 15 minutes the door opened and Megan walked out, She was in the smallest bikini that didn't leave much to the imagination, I wanted to rip her bikini off and stick my...
"Hello, earth to Connor" I was pulled out of my trance
"Ohh ummm sorry I got a little distracted" I was wearing sunglasses so she couldn't see that I was looking at how her tits looked in the bikini
"Well do you want to go back to your room"
"Huh?"
"To change silly"
"Ohh of uhh course" we started walking back to my room trying to catch glimpses of her body without her knowing. Finally we reached my room
"I guess I'll stay out here then" Megan said. I got inside the room and changed into my swimsuit and after 5 minutes I walked out.
"That was fast" Megan commented
"Week I only have one piece to put on"
"Ha, come on let's go down to the pool" we both started walking down towards the pool. The pool had a swim up bar and after we set our stuff down on some chairs I went to get a drink
"Two beers please" I said to the bartender. After the bartender got me my two beers I waded back up to our seats
"Here you go Megan" I said as I handed her a beer
"Aww thank you Connor" she said as she started to drink. After a couple of sips we both went to hop into the pool to swim around a bit when one of the DJ's came on the speaker
"Alright people of the pool we are going to have water polo in the pool of anyone wants to play meet us by the goal nets" I looked over at Megan and she got the meaning
"Sure I'd love to play" we swam over to the water polo game and joined in. We were put on separate teams and after a few minutes of playing things started to get ruff. The ball was hit far from the game and Megan and me were both swimming to get the ball, we both got there at the same time and started wrestling for it. My hands were "accidentally" groping her and I thought I felt her grab my stiffening cock. Soon she wrestled it from me and went to score the winning goal
"Good game Megan"
"Not to bad yourself" she replied "hey can you grab me a beer, I'll be at our spot" she said as she swam to the side of the pool and got out. I was getting harder as I watched her ass sway, I hadn't noticed before but had her ass always swayed like that before. I then swam over to the bar and got up two beers. As I got out of the pool I was fully hard.
"Here's your beer Megan"
"Than... Wait is that a roll of quarters in your pocket or are you just happy to see me" I blushed, she had immediately seen that I had a hard on "hey it's okay all guys get boners, especially when the've seen a girl in a bikini"
"Uhhh t-thank y-yo-you" I stammered back
"Wait, is that from me?" she said standing up now, she approached me until she was as close as we could get without kissing
"Ummmm..." I said my cheeks turning as red as a fire truck
"Cause I think it's kinda hot" she said grabbing my dick through my swimsuit. She then moved her mouth closer to mine until our lips locked we stared making out. Her hand slowly began running my cock and my hands began roaming her back as our tongues entwined.
"GET A ROOM!" Someone from across the pool yelled breaking our embrace.
"Do you want to head back to your room" Megan asked with a slutty tone
"Why wouldn't I" I wrapped my arm around Megan's waist and we walked back to my room, my hand slowly working its way down towards her ass
"Hold it buddy not just yet" Megan said. When we finally reached my room, she pulled me into her embrace as we fell onto the bed, still making out. After 5 minutes of that Megan straddled my chest and began to take off her bikini top. My eyes nearly bulged out of there sockets when she dropped her top, her tits were about 36c and had small but beautiful nipples.
"Do you like what you see?" She asked
"I have never seen anything more beautiful".she laughed as she got up off my chest, She stood infront of me then slowly worked her bikini bottoms down revealing a shaved pussy
"Ohh god that's hot" I said as she made her way to me
"Let's get these off" she said as she began pulling my swimsuit down. My cock popped out almost hitting her in the face
" I see someone's excited" she then began stroking my bare cock, before pulling it into her hot velvet mouth. I could feel her tongue probe around the head of my cock as she took it deeper and deeper into her mouth. Soon I could feel myself hitting the back of her throat as she began to bob her head up and down on my cock
"Ohhh God Megan, don't stop" that only encouraged her as she seamed to pick up speed
"Fffffffffuck M-M-Megan I'm going to CCCCCCUUUUUUUUMMMMMMMM" she took me out of her mouth at that exact moment and kept jacking me off as I came, load after load spurting onto Megan's perfect face. As soon as I came off my post orgasm high I looked down to see Megan scooping my cum off her face and popping it into her mouth
"Mmmmmm, someone tastes good" she said as I almost came again right there.
"How bout I please you now" I said as I got between Megan's legs, I could smell her scent from here. I slowly spread her legs apart as I moved my head closer to her love box, my tongue millimetres away from her forbidden beauty. I slowly stuck my tongue out as I lapped at her pussy
"Ohhhh God, fuck, right there". That only encouraged me more as I sped up the pace. I soon found her clit and she began to moan like there's no tomorrow
"Oooooohhhhhhhhh Fuck that feels so good, don't stop Connor, ohhhhhhhhh" she kept moaning "God Connor I'm going to Cummmmmmmm" I felt a flow of juices reach me as her legs clamped shut around my head. I kept licking her pussy tasting the succulent juices flowing from her love hole. Finally she came drown from her orgasm
"Holy shit that was the best orgasm I've ever had" she panted
"Well how many guys have given you an orgasm?" I asked
"About six" she said
"When did you hook up with them?"
"During parties, when I was drunk or felt the need to get laid, speaking of which". I looked down at my cock only to see it begin to harden. Megan quickly straddled my chest
"Wait Connor are you still a virgin?" She asked
"Y-yes"
"Well tonight you won't be" she said as she grabbed my cock and positioned it between her legs and lowered herself into it. I could feel her tight pussy slowly wrap around my cock.
"Ohhhhhhhhh Megan your pussy's so tight" I moaned eventually I felt my balls hit her crotch and she began moving up and down, I couldn't believe it I was having sex with my crush. I felt my cock hit her cervix every time she came down on me. After a while of moaning from both of us our pace quickened.
"Ohh I'm going to cum Connor" Megan moaned
"me too" I replied. After a few more thrust I came deep into her pussy and Megan came also
"OOOOOOOHHHHHHH GGGGGOOOOOODDDDDDDD" Megan yelled as she collapsed on me. It took a few minutes until my cock popped out of her pussy and she rolled onto her side
"That was the best sex I've ever had" Megan said
"That was the only sex I've ever had" I said back, as we both laughed
"Well hopefully this week that will change" she said succulently
"I love you Megan"
"I love you too Connor" as we both drifted to sleep