Holiday with Leo

By Josh ...

Published on Aug 20, 2003

Gay

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Warning: This story contains gay sex. If you are under the legal age to read such material in your country, or are likely to be offended by such material, then read no further.

This story is fiction and in no way implies the sexual orientation of the real Leonardo DiCaprio.

This is my first attempt at erotic fiction, and any feedback would be welcomed although flames will be ignored.


Chapter One: A Day in the life of me...

Everyone always dreams about meeting Leonardo Dicaprio, I had never really thought about it. Being a male myself usually meant id just sigh when females loathed over him. But it was the day I ran into him on my holiday. I had decided to take a break from my law school schooling and go for a trip to some remote island. I ran into Leo while I was walking along the beach, he nodded at me and smiled as I stopped in my tracks and stared at him. Like I said, I never really thought about Dicaprio. But the day I ran into him on this beach, he looked like different from all his movies. Leo stopped and greeted me with a smile and a handshake.

The Island was fairly small, I hadn't seen too many people on it apart from those who worked at the resort and surely didn't expect to see anyone famous. After getting over the shock of meeting a superstar celeb, The two of us went for a walk. After a while of talking it seemed like we had both known each other for years. Leo was a down to earth kinda guy who may be a star but had life troubles just like everyone else. It made me think back to my younger teen days when my mates and me would pick on Leo for being so pin-up poster boy and everyone loved him. But walking along the beach chatting to him was something different.

Since we both had things to do that day, Leo offered to take me on a hike saying he knew this place we could go swimming. I couldn't say no and later on that day we both headed off for a hike. The walk didn't take long as I thought, probably because as I was walking behind Leo I couldn't help but stare at his ass and body. All through high school I had interests in guys but thought it was hormones. As I looked at where we were we both stood ontop of a huge cliff overlooking a scenery you couldn't even dream up. The water was crystal clear with a tint of blue in it. I didn't think this place held such wonders. I turned to Leo and commented on how the place he said he couldn't believe it too when he first come onto this place.

We looked over the edge for a while talking about what it would be like to go for a swim down there as he suggest we take a dip. I looked over the side and smiled as I placed my bag down and began to unbutton my shirt. That's when Leo raised his hand and stopped me. He stepped in closer and looked me in the eyes as he reaches up and undid some of the buttons on my shirt. My heart was beating and I was wondering if he had brought me up here to make love with me. I couldn't believe what was happening though, Leonardo Decaprio alone with me ontop of one hell of a view and undoing my shirt to expose me chest. After undoing the buttons on my top, Leo leaned in towards me...

...I could have fainted there and then but I didn't. Instead I stood there as Dicaprio kissed me. It was nice and soft as I began to kiss him back. My world had seemed to stop as Leo placed a hand on my stomach area and ran it up my chest and rested it above my right nipple. Still with our lips locked, Leo moved his hand around under my arm and rested it on my back as he brought me towards him so we were touching chest to chest. Not pushing things too far, Leo broke the kiss and looked me in the eyes, he still had his hand under my arm and on my back as he held me close.

All's I could do was smile before leaning in to kiss him this time. Leo figured I was gay too as he slowly pulled down, not wanting to break the kiss I followed him so we were both lying on the dirt on the edge of the cliff with me lying ontop of this gorgeous movie hunk. We still kissed as this time I took the time to run my hand down his neck, I lifted my chest up off his as I ran my hand down the front of his shirt, down his nipples and around his abs. Lowering myself back into the stud, Leo ran a hand over my short hair and moved it down my back until he had both hands on my ass feeling it up.

Before the two of us could get any further, I rolled of Leo and he turned and rested his head on one elbow to look at me. I looked up at the sky and smiled, Leo knew I liked him and wanted him too. I suggested we hold off up here and enjoy or first love making session down there. We rolled over onto our chests and looked over side at the beautiful water scenery and the jungle area up out of the water. Leo agreed and we both stood and backed up a few feet and he grabbed my hand, I quickly lent in and kissed him before we both ran and jumped off the edge, flying through the air until we hit the water.

Both of us soon came up for air as the water dripping down Leo's face got me aroused more then before. I swam over to Leo as he grabbed my hands and pulled me in for a kiss. It was wonderful, doggy paddling in the middle of a crystal clear lake while kissing a movie star the world loves. It didn't take long to get puffed; kissing and kicking to stay above water was draining our breaths. We quickly raced each other to the sandy shore, which Leo won easily as I wasn't the best swimmer around. When I reached him, he was lying on his back half in the water still, with his hands behind his head waiting for me.

I began to crawl out of the water and in-between Leo's legs. As I was close enough I ran my hands up his thighs and past his hips. Slipping my hands under his shirt as I began to move it up his body. In the midst of doing that I leant down and made my first contact with his midsection, kissing it gently as he helped remove his shirt. By the time he had it off his body I had kissed up to his nipples. Taking time to suck on each one before moving up and staring into the eyes of Leonardo Dicaprio. Leo smiled at me before bringing his hands up to the back of my head and bringing me down for a passionate kiss on the lips.

As we kissed, Leo rolled me over and moved so he was now laying ontop of me. He broke the kiss and moved his hands down my chest. Leo moved the ends of my shirt off my body as he done what I had just done to him. Kissing down my chest he stroked his tongue over my nipples making them stand on end. Kissing down he ran his tongue around my belly button while bringing his hands up to play with my nipples and chest area. Leaning back in the sand I moaned at the way Leo was treating my body. He started to make his way back up, licking around my 6-pack abs and over my left nipple, stopping for a second to suck on it. I leant my head up as Leo greeted me with a kiss.

If anyone were to look down from the cliff it would look like two people having sex. But from my view I had a world class movie star ontop of me with his tongue inside my mouth. Leonardo was ontop of me, matching his hips with mine as our bare chests made contact. After a few minutes of nothing but getting on Leo pulled off as he had either hand beside my head and used that to push up. He looked me deep in the eyes and smiled, finally asking if I wanted to go all the way. I smiled back and brought an arm around to the back of his head, bringing him down for a kiss.

Making it a little short I let his head go as he pulled back and I mumbled sure. At this point and time with one hell of a hunk ontop of me I didn't want to push the small talk. Leonardo Dicaprio wanted to fuck me and I sure didn't want to spoil his mood. Leo leaned down and planted a kiss on my lips as he ran one of his hands down my chest. Still being held up by his left arm, he let his right arm slide down to my shorts button to undo it. Leo undone the top button and slid his hand down into my shorts as he began to rub my very hard cock. I lifted my ass up and still kissing Leo, I helped removed my shorts down.

Kicking my shorts off I now laid naked underneath this babe. Leo began to stroke my cock, very slowly as if he is doing this with passion not being in a rush. My ass was moving slightly with his stroke as the sand rubbing against my ass cheeks added to the pleasure of the situation. We could have kissed forever as Leo bit my bottom lip, pulling it a bit before moving down and kissing my neck. I dug my head back in the sand, noticing that Leo had stopped stroking my cock and moved his hand up to my chest area. The stud began kissing my nipples before sucking on the left nipple. Using his free hand, Leo lightly began to rub the tips of his fingers over my right nipples, somehow my cock got harder, standing up at attention from my naked body.

At times Leo would lower his midsection down, touching the head of my cock, causing me to go wild as I laid their, head back and fingers dug into the sand. Leo seemed to be enjoying this as much as I was as he eventually pulled his head up from my left nipple. I too moved my head up a bit to look Leo in the eyes as we just smiled at one another. Leo leant in and kissed me as he moved his body to the left of me and was about to bring one knee over to kneel over me, as I assumed he wanted to suck me off. Before he could do this I stopped the hunk and made him kneel over me the other way so he was sitting on my stomach. I leant up on my elbows and he moved close enough so I could grab his pants, I looked up into his eyes as I undid the top button on his pants and began to undo the fly.

We both stared at one another with passion in our eyes as I slowly moved my hands around to the side of his pants and brought them down as far as they would let me since he was kneeling over me. I still hadn't looked down as I moved my hands up to his chest and ran either one around his nipples. Leo closed his eyes and leant his head back as I pinched his nipples a few times. He seemed to enjoy this as I ran my hand down his abs area and finally looked down to his cock, which stood at attention. I moved my hands either side of it where the pubic hair was nicely trimmed and not too much there. With my left hand I moved it down and played with his balls, while my right hand moved to the shaft of his cock which fit nicely in my palm.

Leo let out a sigh as I slowly worked my hand up his cock until I reached the head. I didn't want to waste time on a hand job so I moved both hands around and pulled his body in closer. Leo obliged and moved in as I brought my right hand back and grabbed his cock again. Leo knew what was coming, so he looked down and watched as I moved my head in closer and stuck my tongue out to lick the head of his cock. Leo flinched a little and took a few deep breaths and closed his eyes as I leant forward some more and moved the head of his cock into my mouth full. I closed my lips around his cock and sucked in which even I felt sent shivers up Leo's spine. Leo's hands eventually moved up to my head where he ran them through my hair. At this time I took more and more of his cock into my mouth until eventually I had him fully in.

With Leo's cock down my throat, I held myself in that position, knowing he was enjoying the warmth of my mouth around his most private area of his body. Deciding this wasn't the best position to suck Leo off, I managed to keep his cock in my mouth while I, with his help, moved us around so he was lying on the sand and I was now kneeling over his legs. Slowly I began to move my mouth off Leo's cock, letting some air down my throat at the same time. I paused at the head of the stars cock and held there while I pushed his pants down his legs and he kicked them off. I now knelt between his legs and grabbed the shaft of his cock with one hand and began to move my mouth up and down his cock, this making him moan with pleasure as he lay back in the sand enjoying the moment. I paid special attention to the head of Leo's cock before licking the shaft while I moved my mouth up and down his cock.

I knew this hot stud couldn't contain his load forever and I desperately wanted to be rewarded with his load in my mouth. Leo's moans were getting louder and closer together as he began to lift his lips up to try and fuck my face, but I easily pushed his thighs down so I was the one doing all the work. I was now off his cock and running my tongue down the shaft, moving all the way down to his balls, pulling one into my mouth with my lips, followed by the second as I sucked and licked them, sending more pleasure down Leo's spine. Leo started screaming he couldn't hold it anymore as I moved so I was lying on the sand and held the base of his cock, moving my mouth over it again as I began to suck this star off once more. This time I ran my free hand up past Leo's belly button and over his stomach as I rubbed the hot stud's chest area. I played with the closest nipple, pulling on it a bit as he began to scream.

I felt Leo's cock swell to a bigger size while it was down my throat, I slowly pulled back so I could taste the wondrous substance which was about to escape from his most private part. I was soon rewarded from all my work on his cock as shot after shot of cum erupted from his perfect cock and into my mouth, hitting the back of my tongue before I swallowed it down and continued to repeat this motion. After he began to subside from his orgasm, I pulled off a bit at the last few shots and sucked on his suck to drain Leo's manhood. Once I was done, I slowly crawled up Leo's body and our lips made contact, same with his own cum which was swapped from my mouth into his as for the first time in this guys life, he tasted his own salty-yet sweet cum. We both laid there kiss, swapping the movie stars cum as it seemed we were both happy with the treatment and presents we received from one another. Still, Leo wasn't finished with me and I could have never imagined what was to come next...

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