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.
I have never met Leonardo DiCaprio, and this story is a fantasy about what could have happened if he had replied to a fan letter I sent to him. This is my first attempt at erotic fiction, and any feedback would be welcomed although flames will be ignored. Leo, if you read this I appologise if it offends you, on the other hand if you enjoy it I would love to hear from you.
Making it Count
by Widget
Until the release of Titanic, I wasn't really aware of Leonardo DiCaprio. Sure I had heard of him, who hadn't, but all I knew was that he had played Romeo in a recent film of Romeo and Juliet. Somehow I had managed to missall of the trailers for the film, and even the posters. This was all to change one night when out of sheer curiosity I decided to go and see Titanic.
I'd heard a few rave reviews of the film, and numerous comments about the dishy DiCaprio, and decided to go and check it out to see if he was as good as everyone was saying he was, or even as cute as they said.
When he first graced the screen I thought to myself "hmm, not bad!", but then I saw the cigarette in his hand thinking to myself "Oh well". I must admit I have always found smoking a distinct turn off. Suddenly we got a close up of his face as the look of concentration on the card game broke into a broad smile. My stomach turned to jelly and I knew that even though he smoked, there was something about this guy that grabbed you by the balls and demanded your un-divided attention, and so as Rose fell for Jack in the film I could feel myself falling for Leo. In the sinking scenes where Jack was handcuffed to some pipes I could feel my heart screaming "No! You can't let him drown, at least not like that!". Then as Rose let go of the frozen Jack near the end, I felt as though that was part of myself sinkingas he drifted down out of sight. I didn't however cry. As the titles started there was the usual scramble to get out of the cinema which really annoys me as I always feel obliged to leave with everyone else, and I feel as though I have missed part of the film if I have not heard the title music at the end. This in turn meant that I did not hear the main title song "My Heart Will Go On".
The following week I went into town hunting for the soundtrack for the film. Being a trainee music teacher I had been listening closely to the soundtrack during the film and decided I just had to get a copy. While I was there I saw the video for Romeo and Juliet and decided now that I thought Leo was drop dead gorgeous that I just had to buy that as well.
A couple of weeks later I went to see Titanic again for a second time, this time taking some friends with me. They knew I was gay, and that I had a thing for Leo, so when we had decided to go to the Cinema they got very little choice in what we went to see. Knowing how heart wrenching I had found the film the first time I saw it, I was expecting to be moved by it again, but was completely unprepared for my reaction to it this time. When Jack first put
Rose into the life boat as the ship was starting to go down, I felt a tear forming in my eye, which was followed by a torrent of them as the lifeboat was lowered. From that moment on I was crying like a baby, uncontrollably, and so forcefully that I was having to concentrate just to be able to breathe.
My friends sat on either side of me were passing me tissues by the dozen, and I was just as quickly soaking them till they became pulp. Lying in bed that night I couldn't help but think how much I had been moved and think to myself that even though I didn't know him the thought of loosing Leo had really got to me.
At the end of each day I would lie in bed and without thinking of anything in particular Leo would come into my mind, and I could feel my groin waking up and demanding attention. I always thought that this kind of attraction to film stars was supposed to be a teenage thing, and there I was, a 21 year old getting all steamy just thinking about a man I have never met, and would probably never meet and yet I could not get him out of my mind.
In the end I decided that if I wrote him a fan letter that would help me to get all of this out of his system. I tried not to emphasise my attraction to him too much knowing he was straight in case I freaked him out, and deep down I thought that if I was really lucky I might get a signed picture sent back in reply, although in reality I doubted if I would even get that.
Time passed by and there was no reply from him, and I gave up on any hope of a response, but still could not get him out of my mind. You can imagine my surprise when one morning in with the usual pile if junk mail I had letter (which is unusual for me anyway) with the postmark Air Mail from LA. I could feel myself start to tremble as I looked at it more closely. The address had been hand written, and the envelope felt to thick to be a photo. I had to sit down as I felt my knees start to go, could this really be from Leo, I didn't know anyone else from LA. Carefully I opened the envelope and started to read the letter inside. It was from Leo, saying how much he appreciated my letter and how his fans are very important to him. I was even more surprised when I saw he had given me his Email address with a request that if I had one that I should Email him as he would love to keep in touch. This was an offer I could not resist.
Immediately I logged on and sent him my Email address and thanked him for his letter which had cheered me up enormously. We exchanged Emails for some time, gradually getting to know one another better, then just as I thought he had no more surprises for me he proved me wrong. In one of his messages, he asked me would I be prepared to do him a big favour. I replied that I would be happy to if I could, and asked what it was. His response took my breath away.... would I be able to fly out to LA. to meet him in my vacation if he paid my airfare? How could I refuse an offer like that, I told him that I would love to, and would fly out just as soon as he wanted me to. We arranged that the ticket would be ready for me to collect at Manchester Airport, and I was on my way.
When my flight finally arrived in the US. I heard a voice over the airport tannoy calling for me to report to the reception desk, from where I was given directions to a private car park. The car park seemed almost deserted, I guess the general public were not normally allowed in here. There was however one car with someone sat in it. The driver door opened and out climbed Leo. He looked at me a little unsure at first, I assume he was looking to compare me with the photo of myself that I had Emailed him. When he seemed happy it was me he started walking towards me. At first I did not recognise him, but once I saw that it was him I felt my feet take root. They refused to budge. He walked right up to me and put his arms around me which took me by surprise, then quietly said to me "I'm so glad you could come. Come on, lets get your bags in the car and we can get home". As soon as I got into the car exhaustion took over and I fell asleep, I had been so excited for the past couple of day that I'd had quite a few sleepless nights, that mixed with the effect of the flight had taken it all out of me and as hard as I tried I just could not keep my eyes open.
When I eventually woke up, I was sat on a settee in front of a roaring log fire with Leo sat next to me just watching me. He must have driven me to his house and had carried me in, not wanting to wake me up he had put me on the settee and let me sleep. I opened my eyes and looked around me slightly dazed as my eyes started to focus on my unfamiliar surroundings and then saw Leo sat right next to me watching me.
"Hi", he said "you must have been real tired, you were out like a light"
"I'm sorry", I said "what time is it, you should have woken me."
"It's 11pm" he said, then gestured towards a collection of foil trays arranged on the floor in front of the fire, saying "I was just about to wake you. I had dinner delivered, I hope you don't mind Take Away, I'm a useless cook and didn't want to poison you with my attempts at food."
I said that Take Away would be fine. I was ravenous and told him I could eat just about anything he put in front of me. He flashed me one of those stunning smiles, and a wicked glint appeared in his eye as if he was planning something that I didn't yet know about. We ate the food really quickly, I guess he was as hungry as I was as we did very little talking, just eating. I could see that he was thinking about something, almost as though there was something he wanted to say to me but wasn't quite sure how to. When we finished eating Leo bagged up all of the little trays and took the into the kitchen. I heard some clunking and banging of cupboard doors, then he returned with a bottle of wine and two glasses. He sat down and slid up really close to me handing me a glass of wine saying "I knew I forgot something earlier". We were both still sat on the rug in front of the fire as he leaned over passing me the glass. I took it and smiled, but I couldn't help wondering why an allegedly straight man was getting so very close to another man. I certainly didn't mind, after all each night I had dreamed about being a lot closer to him than this. As these thoughts were running through my mind, I noticed that Leo had some of the sauce from dinner on the edge of his mouth. Instinctively I licked my finger and used it to wipe the drip away for him. As I started to draw my hand away, he reached out and pulled it back to his mouth and sucked the sauce from it.
Leo looked me deep in the eye as he did this without saying a word took the glass from my hand, reached a hand round the back of my head and drew me close to kiss me. I was in complete and utter shock and froze as he did this. He drew back and looked me in the eye again, this time with a look of panic and vulnerability. I guess he was afraid he had made a move on a straight man and though I would reveal this secret to the world. I had to reassure him it was OK, and did it the best way I knew how. I leaned over to him, put my hand in his and kissed him full on the mouth. I could feel him relax as he mentally took a huge sigh of relief and kissed me back. It was the most tender and gentle kiss I had ever known in my whole life. When we finished, we just looked into each others eyes. We just sat there, and without uttering a word our gazes expressed a love and affection that no words could come close to defining. At that moment I knew that there was something very special between the two of us, but only time could tell what was to become of it.
As I gazed into his eyes, I saw his expression change. From one of wonderment it became a lustful smirk as Leo stood up and held out his hand to me. I took his hand and followed as he led me towards the bedroom. Once inside he closed the door and stood in front of me. With no lights on, and the moonlight flooding in through the windows Leo reached up and started to unbutton my shirt. I gasps as I guessed what this was going to lead to and was unsure if I was ready for him. After all I had only known him a short while, and this could be described as our first date. After thinking about this for at least half a second I decided I might not get another opportunity to be with this incredibly sexy young man, and I wasn't going to miss out on that. I took hold of his polo neck sweater, and pealed it up over his chest and head, revealing the most delicious looking flesh. Even in the dark I could see that his chest was completely hairless. I then undid the button fly on his jeans, letting them fall under their own weight.
While I did this Leo continued to undress me, undoing the clasp on my trousers and then brushing his hand against my cock as he slid the zip down.
Creeping his hands inside he then eased my trousers down till they fell around my ankles and there we were, both stood in the moonlight with our trousers at our feet, wearing only our underwear. We both kicked off our shoes and socks (I never was much into feet), and stood looking at each other. I stepped towards Leo and placing both hands flat on his chest, leaned forward and kissed him gently on the neck. A feeling of electricity passed between us as he wrapped his arms around me drawing me close. As our bodies pressed against one another we kissed, this time letting our tongues probe into each others mouths. I slid my hands down his back and into his boxers to caress his buns. They were firm, well toned, and tensed at my touch. I eased my hands round his waist and began to slide his boxers over his smooth hips and let them fall to the ground. They needed a little guidance to get past his stiff cock which was pointing upwards and creating quite a tent in them, but they soon fell to the ground as had the rest of his clothes leaving him stood naked in my arms. Leo following my lead relieved me of my boxers and there we were stood kissing and embracing naked in the moonlight. As we made our way towards the bed I told Leo that this would be my first time with a man, and he said that it was the first time for him also. I don't know how, but I knew he was telling me the truth, and that made this moment all that much more special as we were both about to give ourselves to another in a way we had never done before. We lay on the bed and kissed each other for what seemed like ages, exploring each others bodies. I worked my way down past his erect nipples, down his breast bone, past his naval and towards his erect cock. It jumped as I touched it, and I could feel slight tracks of precum forming on his slit. Carefully I placed my tongue against it and gently began to lick it like a child would with a lolly they weren't sure they would like the taste of. His precum tasted salty and yet sweet at the same time. I could feel him squirm under this teasing and began to suck slowly on the head of his cock. Each time easing more into my mouth, then starting to take in the shaft as well. As I did this I could feel his hips begin to grind upwards in time with my sucking motion. I guessed he would not last long, but wanted him so badly I could not prolong the inevitable for much longer. I sucked for all my life was worth, feeling his cock go deeper and deeper into my mouth till it brushed against the back of my throat, then it happened. Leo began gasping as he gripped the bed sheet with his fists clenched so tight that not even a crow-bar could prise them loose. His body tensed and the muscles began to pound and then his life fluid gushed into my mouth. His cock kept on pumping, and I was swallowing as fast as I could determined not to loose any, then as the pumping subsided I felt his body relax and I knew that he had finished (for now anyway). I kept on licking his cock head to gather up every last bit of cum, only when I was sure I had collected it all did I come up for air. Leo lay there breathing in short sharp gasps as he recovered from his climax, then held out his arms to me and pulled me close to kiss him. As I leaned over him I could feel his heart pounding against his chest and his breath against my face as his breathing began to return to normal, then we kissed. A long passionate kiss as his tongue explored my mouth for any remaining traces of his cum. When our lips parted, Leo looked at me with an expression of satisfaction and delight and said quite simply "Wow!". Then we lay there for some time enjoying the moment as he got his breath back.
After a minute or two, I rolled onto my side and started stroking Leo's chest with the back of my hand. This was obviously having the desired effect as his cock started to show signs of life again. Leo turned to look at me, and then with a grin pushed me over onto my back and straddled my waist. I lay there looking up at him with my cock begging for attention as he leaned forward to kiss me. We kissed for some time and I was finding the warmth of his body pressed to mine to be very reassuring as Leo started to kiss his way down my neck towards my chest. He lingered at the nipples, sucking them and teasing the tips with his tongue. The anticipation of what was to come was driving me wild, and I felt as though my body was on fire as every inch of my skin became hyper sensitive. My waist started to buck as the result of what he was doing, screaming out for a release as the tip of my cock rubbed against the small of his back. I started to drip cum as I was anticipating his next move, when he made his way further down my body to approach my cock. He pressed his nose into my groin and took a sharp breath in, inhaling my scent. Then very gently, Leo kissed the side of my cock. Over and over again he kissed it, moving up and down the shaft causing me to writhe beneath him with desire. "Oh God!" I whispered as I felt I could not hold on much longer. Realising the effect he was having on me, Leo decided to make his move. He worked his way up my shaft one last time then took the tip of my cock into his mouth. The mere thought of him doing this to me was about as much as I could stand as my hips started really bucking. He hardly had to do anything now as I was fucking his face for all I was worth and then the moment came, the blessed release as my cum poured out into his mouth. I could have screamed as he carried on sucking me ensuring he got every last drop, then he crawled up the bed and lay beside me on his chest. As I started to regain an awareness of my surroundings, I looked over at him lying there next to me. He had little droplets of sweat on his back glistening in the moonlight from the window. His shoulders were much broader than they had seemed on the cinema screen, and as he lay there his spine seemed to lie at the bottom of a valley which ran all the way down his back leading to his tight buns. Those beautiful buns, which seemed to be almost glowing in this moonlight, were beckoning me to pay them some attention, almost radiating warmth. Gently, almost timidly I reached over and placed a hand on the back of one of his thighs, feeling the muscles twitch as I did so. Slowly and lightly I ran my hand up and down his inner thigh, floating on the light covering of fair hairs on his legs. This was obviously having the desired effect as he let out a long low sigh and developed a far away dreamy expression on his face. With each stroke I got a bit closer to his butt, then started to work my way up and down his cheeks where the hair seemed to end and the completely smooth skin began. I began to knead his cheeks as though I were kneading a dough mix, gradually working my way between his two shapely buns towards the trophy that lay within, his virgin ass. My fingers started to slip down into the gap between his buns, brushing his hole with each stroke, and again Leo let out a long sigh, he was obviously enjoying this and relaxing with it. I could tell how relaxed he was becoming when my fingers started to slip into his hole with each passing stroke. I knew it would not take much work to loosen him up, and began to insert a finger into his hole. I got just past the first knuckle when he tightened slightly around my finger then after a moment relaxed again. I continued to press until my finger was as far in as it could go, then I started a smooth in and out motion with the finger. Soon I felt that Leo was loose enough for a second finger, which his ass readily accepted. The time had come to make my move and claim my man. Keeping my fingers up his ass, I moved closer to him and stretched one leg over both of his. I leaned in and kissed him deeply as I slid over onto his back. Lying on his back, my head level with his we kissed again for quite some time, then I felt his sphincter contract a few times around my fingers as a reminder of what I had been about to do. Resting my face on Leo's shoulder, so that I could watch his reactions, I withdrew my fingers from his ass and positioned myself ready to penetrate him. I positioned the tip of my cock at his entry, the quietly whispered to him "are you sure?". He did not say anything, just smiled, and I knew that he was ready. Very carefully I pressed against his hole and started to slide in. I had never been with a man before, but from the stories I had read on the net I knew enough to know that this could be a painful experience for Leo at first. I paid particular attention to his facial expressions telling me when he needed a moment to get used to the sensation and when it was ok to enter further. It took quite a while to get my full length in, and when I was fully in we lay there for a while to allow us both to get used to these new sensations. After a while Leo signaled once more that he was ready by squeezing on me a few times. Taking this as my cue I began to make love to him. Our bodies were joined, our hearts were beating together, our breaths were coming and going together, we were together in every way it was possible to be together. These new sensations were completely wild. I felt a burning in my cock, as though it would explode at any moment, yet I knew that having already come once that evening I would be able to last slightly longer this time, and this was an ecstasy that I intended to make last for as long as possible. I took my time savouring the sensation, and relishing the look of sheer bliss on Leo's face. I made my strokes deliberately long and slow, pulling almost all of the way out, then easing my way back in. This must have been having more of an effect on Leo than I had realised, because after a while his breathing started to come in short sharp gasps. His fists clenched the bed sheets tighter and tighter making his knuckles go completely white. Then he started bucking about beneath me, then it happened. His sphincter started to grip my cock as though it were trying to squeeze it to death, relaxing for a fraction of a second then clamping down again. I guessed what was happening. Leo was cumming beneath me. This new gripping of my cock was driving me wild, and took me past the point of no return. My muscles locked as my whole body froze for what seemed like ages then my cock began to pulsate then after a while I could feel myself spurting my cum into Leo. When I was finally done I pulled out of Leo and lay down next to him once more. He turned to me, putting his arms around me and gave me a great big kiss before falling asleep with his head on my chest and his arms still wrapped around me.
I started to imagine what the press would say about him if they ever found out about this, or what my family would say if they found out I was gay. Then I thought about the thousands of miles that separated our two worlds, and began to cry. Was this to be my life, living in torment, being in love with a man who I would soon be thousands of miles away from again. Never being able to tell anyone what we had been to each other for fear of it harming his career. As I felt the tears on my cheeks I looked down at Leo asleep in my arms. He looked completely at peace. Suddenly I felt as though there would be a way of working this out, we only had to find it. Anyway I was in bed with one of the most beautiful men on the planet, a man who I could honestly say I had fallen in love with. Once again a smile came back to my face and I drifted off to sleep with thoughts only of my love for him. Maybe we would not have much time together, but what little time there was we were going to enjoy.
Comments or suggestions will be welcomed at the_only_widget@hotmail.com although I cannot promise to reply. Should I continue this story with a second part?
Please remember this is my first attempt at an erotic story, so any advice as to how to develop it would be welcome, but please keep comments constructive, I get hurt easily.