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.