When I was thirteen my father got a promotion, which meant that we were going to have to move interstate. I had lived in Queensland my whole life and now struggled to adjust to my new life in Melbourne; having to start at a new high school, not knowing anyone or anything about the area in which we were living.
I met Leslie on my first day of school; it was the only good thing that happened that day. We quickly became the best of friends and now, over 5 years later, we are still inseparable.
Tonight we were heading out to Leslie’s parent’s beach house for the first time by ourselves, we had spent every summer there with her parents since we had started high school and were very excited to finally have some freedom for the holidays.
As I finished packing for our New Year’s trip I made one last check in the mirror with a smile, I had always been a fairly geeky kid but over the last year I had matured into a well toned man at 5’10; with my confidence growing every day I was feeling really good about myself.
I had never had much luck with the ladies; at eighteen years old I was one of the only guys in my year level that had yet to lose their virginity. It was not like I had never been with anyone before, over the past year I had done just about everything apart from have sex.
I was hoping this holiday and the beginning of the New Year was going to improve my luck.
As I pulled into Leslie’s driveway, I couldn’t help but notice how much Leslie had grown over the last few years. She was around 5’6 with long blonde hair and a great tan, she had always been quite sporty and as a result of this, had a nice toned body. She had fairly large breasts, I had never been good with cup sizes but I would guess between a C and D cup. I noticed she also had a really tight arse as she bent down to grab her bags.
It was going to take us around two hours to reach the holiday house and I wasn’t sure what we could do to pass the time.
“I have a game we could play.” Leslie suggested as she adjusted her seat for the long drive. ‘And what would that be?’ I asked as I let my eyes drift down between her cleavage. I looked up before she could catch me staring, “We could play I have never, but as we can’t drink, every time you have done something there is a dare or task you have to complete when we get to the holiday house.” She said with that sweet smile that I knew so well.
‘That sounds like fun.’ I reply as I turn my focus back to the road. ‘You have to start though.’ I said with a smile.
“Ok then, I don’t mind starting, umm, I have never slept naked before.” Leslie said to get the game started.
‘Guilty.’ I replied, ‘Guess that’s one to me for later.’
“Your turn.” Said Leslie with a smile.
‘Umm, I have never had sex.’ I admitted, a little embarrassed, even to my best friend.
“Yeah I guess that’s one to me as well.” Leslie stated with a blush.
By the end of the car trip I was happy I only had two tasks to complete, whereas Leslie had five for me to set for her. As we moved our bags inside I began to wonder what kind of tasks Leslie had in mind, I decided not to look too closely into that at the moment, as lately my thoughts towards Leslie tended to get quite sexual and I didn’t think that’s what Leslie had intended.
I poured a few drinks for Leslie and myself before moving out to the balcony.
Leslie joined me a few minutes later wearing a tiny black bikini top and a pleated mini skirt. She thanked me for the drink as she sat across from me as we both looked out to the ocean below. I looked over to Leslie and noticed I had a perfect view up her skirt; I was surprised to see she wore nothing underneath and I caught my first glimpse of her tight pussy. I quickly looked to my drink as Leslie turned to me, I hoped she hadn’t caught me peeking up her skirt and I had to cover my cock as it began to grow from the sight.
“So what are we going to do about these tasks we have to complete?” Leslie asked before taking a long sip of her drink.
‘I was wondering about that.’ I replied, ‘What are the ground rules’? I asked with a sideways glance. “Well, as it’s just us, I think we’d be safe in saying anything goes.” Leslie replied as she moved closer to me, “It’s not like either of us would do anything to hurt the other.”
‘That’s true, but I think you should start, I’m still a little confused.’ I said before moving to pour a few more drinks.
“Well Tobias,” I cringed at her using my full name, she was the only person that could get away with using it. “You have to run naked around the whole house.” said Leslie with a giggle.
‘I think I can handle that.’ I reply with a smile, I skull the rest of my drink before pulling off my singlet, dropping my board shorts, before moving towards the house.
“I said naked” ordered Leslie as her eyes flashed towards my underwear.
I reluctantly took off my underwear revealing my hardening cock; the look of shock was evident in her eyes at the length of my cock. I didn’t wait long enough for her to comment as I ran the whole way around the house and had my board shorts back on before she had the chance for a second glance.
‘Your turn,’ I said with a smile, ‘for your first task, you have to lose the bikini top until all your tasks are complete.’
Leslie stared at me in shock for a second before relaxing, “Fine then,” she says with a half smile before removing her bikini top, revealing her perfect tits, I watched as her nipples harden in the breeze. “I think you should set my next task too, since I have so many more to complete then you.” She says as she watched my cock slowly hardening inside my board shorts.
I grabbed another drink while I thought about her next task, trying to work out what would be going too far. Remembering that Leslie still had another task to set for me I decided it would be smart to go for a safe option. I sat down on the couch with my drink and turned to face Leslie, I made my decision, ‘You’re going to give me a lap dance.’ I told her with a smile. The confidence in my voice must have startled Leslie as she didn’t even question the task.
She walked over and straddled me, pushing her tits right into my face as she began to grind her pussy against my cock bringing it to full attention inside my board shorts. I watched Leslie’s eyes light up as she felt my hard cock rubbing against her bare pussy. Leslie turned around and began to rub her pussy back and forth against my cock, before bending forward giving me a perfect view of her tight pussy and cute rosebud arse, I couldn’t help but notice how wet her pussy looked before she slowly danced her way back to standing, giving her arse a light spank before letting her miniskirt fall to cover her arse once more.
I watched as Leslie walked back over to her drink and skull the rest of it.
I was shocked that my best friend could be so sexual; it had been the most arousing thing I had ever experienced.
“You’re enjoying this aren’t you?” Leslie asked as she poured herself another drink. I was surprised to see that she wasn’t even covering her bare tits anymore and seemed quite comfortable being half naked.
‘Yeah I am,’ I replied with a smile, ‘I think you are too.’
“You know me too well,” Leslie stated with a wink, ‘I think it’s time for me to set my task for you.’
I was beginning to get quite worried at what she would set for me; after all I had just made her give me a lap dance.
“You look a little scared.” Said Leslie with a smile.
‘Yeah, just a little.’ I replied with a blush.
“Well maybe we should just get on with your task then.” She said as I poured myself I drink. “For your last task, you have to lose those board shorts until all my tasks are complete, I want to see that long hard cock of yours again.” Leslie added with a smile.
I was a little shocked with the task she had set for me, but considering I still had 3 tasks up my sleeve, I knew I could use this to my advantage.
I quickly drank the rest of my drink before walking right up to Leslie and pulled down my board shorts, allowing my hard cock to flick up right in front of her face as she sat on the couch. I watched with a smile as I saw the lust in her eyes at the sight of my 10″ thick cock standing at full attention right before her eyes, I knew then that I had her.
I could set her any task I wanted and I wouldn’t be getting a single complaint from her. This was definitely turning into a holiday I would never forget.
‘So what do u think?’ I asked her with a smile.
“Mmm, It’s so big.” She exclaimed as her hand brushed against her hardening nipple.
I decided to pour us a few more drinks while I decided on Leslie’s next 3 tasks, I handed her a drink as I once again caught the perfect view up Leslie’s skirt, as I stared at her wet pussy I knew exactly what her next task had to be.
‘For your next task, I want to watch you finger yourself until you cum.’ I said as I moved to sit on the couch next to her. I watched as Leslie lay down and spread her legs, giving me an even better view of her tight wet pussy.
Her hand slowly moved its way down her entire body and brushed slowly across her clit, she let out a slight moan as she began to rub her clit, the other hand bringing her skirt to rest upon her toned stomach. She brought her fingers to rest upon the entrance to her pussy and stared right into my eyes before driving her fingers deep inside her tight fuck hole, letting out a loud moan.
She began to fuck her pussy hard and fast with her fingers deep inside her tight sex, her other hand slowly trailed along her tanned skin as it made its way up to her large tits and began to pinch tightly onto her nipples.
Her breathing increased as she began to fuck herself closer to orgasm, I watched as her thumb began to rub fast across her clit while her fingers continued to slide in and out of her wet pussy with increasing speed, her moans were beginning to turn into screams of pleasure as her other hand grabbed tightly onto her tits.
Leslie lifted her hips so she could push her fingers deeper into her wanting sex, and her body began to spasm as she brought herself to an orgasm. She pulled her fingers from her pussy and began to rub her clit with such vigor as she began to squirt hard from her pussy. I couldn’t believe my eyes as Leslie’s orgasm shot her juices from her pussy across the couch covering my hard cock and as she pulled up on her clit it shot even higher and her pussy juices covered my face and landed in my open mouth.
Her breathing returned to soft moans as her fingers slowly brushed across her clit as the last of her orgasm trickled from her pussy. I had never seen such an erotic sight, my body was nearly completely covered in Leslie’s pussy juices and my cock was aching for attention.
‘That was amazing.’ I said to Leslie as my hands played with her juices on my body.
“I’ve never cum like that in all my life.” Leslie sighed as she blushed and brought her skirt down to cover her pussy.
‘What made you cum so hard?’ I asked with a smile.
“Having you watch me, it was just making me so horny,” she answered as she sat up to grab her drink.
‘Are you ready for your next task?’ I asked as I slowly lay back on the couch so that my long cock came to a rest along my stomach.
“Yes.” She replied as her eyes returned their gaze to my cock.
‘Your next task is to suck my cock.” I told her and with a smile she replied “my pleasure.”
Leslie slowly moved to lie between my legs; the lust in her eyes was beginning to control her whole body as she took my long hard cock into her hand. Her slow strokes on my cock felt so good, she used long soft strokes on my cock, which slipped through her fingers as both were covered in her pussy’s juices. I watched as Leslie’s tongue slowly licked the tip of my cock, sending a wave of pleasure through my body.
Her hand moved to grab my balls as she took my cock into her mouth, I had fantasized about this moment for so long but they had never compared to this.
Leslie’s tongue slowly massaged around my cock as she began to move my cock in and out of her mouth, I let out a low moan as she began to push my cock deeper into her mouth.
I brought my hands to the back of Leslie’s head, forcing my cock deeper into her throat. I wasn’t surprised when she began to gag on my cock, none of the girls I had been with had managed to deep throat my whole cock.
Leslie pulled away from my cock gasping for air; she looked up at me with her bright blue eyes and grabbed hard with both hands onto my arse, before opening her mouth and driving my entire cock down her throat. I couldn’t believe how amazing it felt as she began to deep throat my cock hard and deep.
Leslie brought her mouth from my cock and gripped it hard with her hand as she began to make long fast strokes on my cock, I watched in amazement as she licked at me balls before taking them into her mouth and sucking hard. I could feel her tongue licking all around my balls as her hand began to stroke even faster. Before I knew it I was moaning uncontrollably and knew my orgasm was approaching fast, Leslie sensed this as my body began to tense up, she moved her way back to my cock and began to suck hard on the head of my cock and continued to stroke fast with her hand.
Just as I was about to cum I feel her push her finger right up my arsehole, I had never felt anything like it in my life.
She felt my body begin to jerk and removed her mouth from my cock, just as my orgasm hit its peak and my cum shot straight from my cock.
I had never cum so hard in my life, as my body began to calm I looked down to Leslie and saw that I had shot all over her face, it was covering her cheeks, her nose, all over her lips, some had gone straight into her bright blue eyes and I had even filled most of her open mouth with my cum.
Leslie looked to be enjoying herself as she savored the taste of my cum in her mouth before swallowing the first of my cum, she then began to push all the cum from her face into her mouth, until it was once again full.
I smiled as she looked up at me with her open mouth, showing me the cum before swallowing another load.
She grabbed a hold of my cock and began to suck the last few drops of cum from my cock. I let out one last moan before she took my cock from her mouth and said with a smile, “Did you enjoy that Tobias?”
‘So much Leslie, I can’t believe you got my cock all the way down your throat.’ I replied, still trying to catch my breath after the best orgasm I had ever experienced.
“I just wanted to please you.” She said with a blush as she sat up to have a drink.
‘I think your going to enjoy your final task then.’ I said with a smile.
“And what would that be?” Leslie asked as she slowly caressed her breast.
I move closer to her, my hand slips between her legs and my fingers push straight into her wet pussy causing her to moan out loud, before I whispered in her ear ‘For your final task, you shall be my slave for the rest of our
“Yes master,” she moans as my fingers slowly leave her pussy, “I’ll do anything you say.” Leslie added before sucking her juices from my fingers.
‘Follow me to the bedroom slave.’ I said as I walked away from the couch.
As we entered the room I instructed Leslie to remove her skirt as I lay down on the bed to watch. Leslie slowly rubbed her breasts before letting her hands trail down her toned body, as they reached her mini skirt she turned and slowly slid the skirt over her arse and down her legs as she bent forward, revealing her tight wet pussy and her little rosebud that looked so tight, I couldn’t wait to get my cock inside her.
I had been looking forward to this moment for a long time I was finally about to lose my virginity and I couldn’t think of a better person to do it with than my best friend.
‘Come and sit on my cock.’ I said to Leslie as I watched her eyes light up in lust, she practically leapt onto the bed before straddling me. Taking my cock in her hand and guiding it to the entrance of her tight wet pussy, she let out a soft moan as my cock began to part her lips and slowly began to slide my cock deeper into her tight pussy.
I couldn’t believe how tight her pussy was, I grabbed Leslie’s hips and with one hard thrust drove my entire cock deep inside her. She moaned so loud as she began to move her pussy up and down on my cock, it was the best thing I had ever felt and I didn’t want it to ever end.
“Your cock is so big master,” Leslie moaned as her thrusts on my cock became longer so she could feel every inch of my cock pushing deep into her pussy, “My pussy never felt this full before.” She added as I gripped hard on her arse, pulling her down hard on my cock, every breath was turning into a moan as I began to fuck her harder and my thrusts inside her pussy became faster.
I watched as Leslie’s hand moved down to her clit and she began to rub as slow at first but as my cock began to fuck faster so did her hand rubbing on her clit.
Leslie’s moans quickly became screams of pleasure as she impaled herself on my hard cock, “Oh master, I’m going to cum all over your cock.” Leslie screamed before her body began to shake, I slipped both my middle fingers up into her tight arse hole as her wet pussy continued to slide up and down on my cock. I fucked her pussy harder and deeper than I had first thought possible as I built her to a massive orgasm, with one last hard thrust I pushed my fingers as deep as I could reach up her tight arse and my cock shot from her pussy as she began to squirt uncontrollably over
my cock and balls.
Leslie collapsed next to me on the bed, her body completely exhausted, “That was the best fuck I have ever had,” she sighed with a smile, “I can’t believe it was your first time.” She added as she looked up at me.
‘Did I say I was finished yet slave?’ I asked as my hard cock stood at full attention in front of her face.
“I’m sorry master, I just don’t know if I can handle anymore.” She replied with her bright blue eyes staring at my cock.
‘It sounds like you think you have a choice slave,’ I moved down a little lower on the bed to position myself between her legs, ‘You don’t.’ I added as I spread her legs and guided my cock towards her dripping pussy.
I thrust my cock as hard as I could into her pussy, as it once again stretched to allow my whole cock to fill her. She let out a whole moan of surprise, her body was still sensitive from her orgasm and the unexpected pleasure she felt was almost too much to handle. I lifted her legs over my shoulders, allowing me to push even deeper inside her pussy, before I started to fuck her as fast and hard as I could feel my balls slap against her tight arse with every thrust. “Master that feels so good, your cock is going so deep inside me, I love your cock.” She screamed as I continued to fuck her as hard as I could. I pulled both her legs together and placed them over my shoulder, making her pussy even tighter around my cock.
Leslie’s screams where getting louder with every thrust and I knew she was building towards another orgasm. I turned Leslie onto her hands and knees and began to fuck her doggy style, with every hard thrust my balls slapped against her clit. I grabbed her tits hard with both hands as I pushed my cock deep into her dripping pussy; I felt her nipples hardening against my touch and began to pinch the hard as Leslie let of a scream of delight.
I could feel both of our orgasms rapidly approaching, Leslie’s hand moved up between her legs and began to frantically rub her clit. I grabbed on to Leslie’s hips and began to fuck her with everything I had.
Leslie’s screams of pleasure had suddenly caught in her throat as I fucked her into her orgasm, she collapsed forward off my cock as her pussy began to squirt her cum for the third time that day. As Leslie began to catch her breath I turned her onto her back as I stroked my cock in my hand, as Leslie stared up at me with those bright blue eyes I was hit with the sudden force of my orgasm and cum shot from my cock straight into her eyes, causing her to gasp as I continued to cum. I stroked my cock and shot hard into the back of her throat faster than she had expected and she began to choke on my cum. I grabbed the back of Leslie’s head and thrust my cock into the back of her throat as my cum shot right down her throat.
Leslie was swallowing as fast as she could, there was too much for her to swallow and my cum dripped from both sides of her mouth down her chin and onto her large tits. Leslie continued to suck my cock until she was sure she had the last of my cum. As my cock slipped out of her mouth I watched as she scooped my cum from her tits and licked it all up, savoring the taste. “Thank you master.” She moaned with as she wiped my cum from her eyes.
‘Your welcome my slave.’ I replied before collapsing from exhaustion in
the arms of my best friend. As I closed my eyes with a smile I realised, there was a whole week ahead of us before we had to return to reality and I couldn’t have been happier.