Date: Sun, 20 Aug 2017 03:52:10 +0200 From: Black Cat Subject: Oscar DISCLAIMER: The following story contains sex scenes between a young boy aged 10-14 and older men and women. If this could offend you, please leave. Please be aware of the laws in your area regarding such material and surf responsibly. ------------------------------------------------------- If there was ever a boy for whom the phrase "Small but perfectly formed" applied to you, it could be Oscar. Small for his age, he nonetheless was stunningly good looking with short whitish parted blonde hair, fair skin, seductive blue eyes and plump thighs. He typically wore jeans and a fashionable T-shirt, and had a large bubble butt which seemed to perfectly naturally culminate his impressive plump thighs. Oscar, while he had a strong sense of independence and was quite self-centered (though very unselfish), also had lots of friends. He was remarkably socially competent and knew how to play the unwritten rules of social etiquette in order to gain acceptance and have lots of friends. While he was very capable of getting along with just about anyone, he also had a somewhat rebellious streak deep down. He found that in TV programs he often wanted the bad guy to win, and also felt deeply distrustful of society and authority. Despite his young age, Oscar had an unusually well-developed knowledge of the society he lived in. He had come to the realization that the values of the society he grew up in were flawed, especially when it comes to children. He felt society did not respect children at all and treated them as second-class citizens, especially regarding their sexuality. Overall, he knew the rules of society were screwed, but he enjoyed using this knowledge to his advantage - as it gave him a sense that he was wild and rebellious to be so young and having such knowledge, and embarking on such wild sexual encounters. Oscar also got to travel a lot, as he had parents who worked high up in international business. He visited and lived in several countries throughout his childhood which gave him a worldly, multi-cultural persective from an early age. He also got a real feel for different cultures of women and girls and how they all appealled to him sexually, as well has had the opportunity to fool around with girls from several different cultures. Oscar was very smart, and always got straight A grades in school. However, he was somewhat jaded by the whole school system and got bored at school easily. His brain seemed to function much faster than most of the other students, and while he had no trouble achieving excellent results, he also felt it was tiresome having to keep up with the comparatively slower pace which everyone at school was encouraged to learn at, and also felt that schools perhaps were rigid and politically correct places which children naturally learnt to dislike. Another thing that Oscar felt he was at odds with other children with was his unusually intense sexual feelings at a young age. Since he was in kindergarten he had found himself to be a natural womanizer, flirting with other girls in his class in a natural childish way, and even his teacher. From a very early age, he knew how intensely he liked girls and appreciated and respected the beauty of the female body. Therefore he always found it important to play the rules of the social game to the best of his ability, and thus had no trouble making friends with the prettiest girls in his class and exploring what they could do together. He found that the best thing to do was to go at the pace of whatever the girls enjoyed, and be gentle. This was an effective technique and throughout his early childhood it enabled him to have many sexual experiences with other girls his age and older. He enjoyed looking at them naked and having them play with his privates, as well as play with their private parts. This felt very intense for him and highly rewarding to a point most kids simply have no comprehension of. As well as genital play, he also liked to explore girl's asses and finger them, and found himself fascinated by the way girls looked so different in one way (with a vagina) but so similar in another (with the butt). As intensely attracted to girls as he was, there were other intense aspects of his sexuality as well. From a very early age, Oscar began to discover that he appreciated attention and affection from adult men. He eventually learned through his early childhood that he had a real craving to be admired sexually by them. While he wasn't physically attracted to them, this was no barrier to the fact that he got really excited by the idea of them feeling attracted to him, and appreciating his attraction to women. He was to get his chance to explore this area further with a young adult babysitter when he was 10 years old. At the age of 10, Oscar had a 23-year old male babysitter who seemed unusual - Leonard, a shy social outcast, but nonetheless very interesting in an unconventional way. Firstly, he liked rock music which Oscar could greatly appreciate. But more than that - it seemed he and Oscar could bond naturally in a mentor relationship where Oscar could relate to and be inspired by the young man's unusual yet intelligent way of seeing the world. He had libertarian views, and while Oscar was largely turned off by the politically correct views of many people, he found he could naturally adapt to the views of Leonard like a duck to water, without any trouble. At first, they spent many hours and days listening to Rock music, wrestling and cuddling with each other, and talking about Leonard's views and philosophies on life. They would explore subjects like Shakespeare, Ancient Greece, Cultural Relativism, as well as things like the relationship of Politics to Money, power and control. Although these would normally seem like complex subjects to a child, Leonard had a patient and effective way of bringing himself down to a child's level while explaining them so that Oscar could understand it perfectly. In addition to this, however, their relationship continued progressing and becoming gradually more intimate. Oscar first broke the ice by talking about his attraction to women and girls and the girlfriends he had had over the years. He immediately picked up on how Leonard seemed unusually fascinated by this, and as such his antenna quivered as he quickly began to understand he could have an opportunity here, with a man who admires him. He then would enjoy looking at modelling pictures, gradually in more raunchy poses online, while Leonard watched him intently. The point of no return came when Oscar was sitting at the computer looking at a picture of a young model in panties and a bra with her legs spread and said: "Damn, I've got a stiffy." Leonard said, in a shaky excited voice, "Wow really? You little stud." "Yeah, I want her so badly." Leonard said "I don't believe you've got a stiffy." Oscar said "Oh really? Do you want me to prove it to you." Leonard froze, thought for a minute and then said "Oscar, you know I could get in real trouble for this. I really like you a lot but I don't know about this." Oscar said "I really like you too Leonard, and believe me I will never tell. I really want you to see, please let me show you." Leonard took a deep breath and sighed and said "Okay Oscar, go ahead." Oscar, with trembling fingers, unbuttoned his jeans and zipper, dropped his pants and revealed his tighty whities with a clear large bulge in them. Leonard looked excited as he knew that whatever was in them must be pretty big. Then Oscar slowly and perhaps a little teasingly, dropped his white undies to his knees and stood in the middle of the room bearing all in front of Leonard. Nothing was said for a few minutes. Leonard could not take his eyes off what he saw. Oscar's penis was fully erect and hairless, and it was uncut. He had quite a long foreskin but his penis looked very healthy and large, perhaps as much as four inches. Oscar felt thrilled and trembled with excitement as he soaked in the feeling of having someone much older illicitly staring at his lower body and admiring it in a sexual way. From then on, Oscar had control over the relationship and progressed it in a sexual way. At first the relationship consisted just of Oscar stripping off his clothes, dancing round the room provocatively and getting a real thrill over Leonard watching him in a pervy way. However, soon it had progressed to where Oscar let Leonard touch him, followed by the intense experience of oral sex. This was intense for Oscar as it really powerfully satisfied his desire to be physically intimate with an older man who loved him. Sometimes Oscar's desire for control in the relationship would be really powerful. He would sometimes get in an aggressive sexual mood where he would enjoy pinning down Leonard's face between his smooth plump thighs and legs, and fucking his face and saying "Oh yeah, suck me, bitch". He felt truly awesome as he knew he had full control over the pleasure of an older man, making him feel wonderful with his little boyhood. At first, some aspects of their relationship were challenging. Oscar really enjoyed having his ass worshipped and fingered and licked by Leonard, and it gave him a real sense of validation sexually. However some aspects of the anal preparation, were painful - however, Oscar valued the friendship greatly and understood the rewards of celebrating their love were far greater than whatever challenges there may be. Leonard had also discovered from his previous relationships that a boy's ass is much more capable of holding a man's dick that one might expect, as long as there is lots of lube and preparation. Once Oscar had got the hang of the anal preparation, he intensely became excited and hooked on it very fast. He mostly enjoyed the combination between the intense physical stimulation he was feeling, as well as the power he had over possessing an older person's manhood inside his little bottom. This really went in well with his rebellious streak as a child, by having much more power than any other boy his age could have. Leonard found that Oscar could be very demanding sexually, and got a real thrill out of hearing Oscar demand that Leonard fuck him harder, to give him the biggest thrill and make him feel as in control as possible. Throughout their relationship, Leonard was happy to also satisfy Oscar's desires by providing him with a good supply of porn as well. He showed Oscar many pictures and videos and really gave him an improved education on how men and woman have sex - and got a real thril out of watching Oscar rub himself to orgasm over videos of man and woman having vaginal intercourse as well as anal sex. He also showed some videos to Oscar of men having anal sex with younger men, and while Oscar thought it was kind of intriguing, he was not as intensely physically attracted to them as the ones involving male/female sex. After their relationship had progressed for a substantial amount of time, Oscar got a shock when he was told his family had to move to Brazil for a while due to his parents' business. He was torn - as while he loved exploring new cultures and the general exotic luxurious experience that came with his family travel, he was afraid he might miss Leonard severely. However, after realizing he could come back home every school holidays, he talked with Leonard and they agreed that they would keep in touch, as well as meet up as often as possible when he came back home. Leonard also explained that while he will be sorry to see him go, that sometimes the nature of a Boylove relationship means that it's okay if it doesn't always last forever, that they can remember the good times and the positive benefits, and take that into their lives as they move on. The family accommodation in Brazil was quite superb. They lived in a large house, almost a mansion, by the sea surrounded by tropical bush, with lots of house staff. Oscar enjoyed becoming familiar with new cultures and trying different foods, and before long he was settling in to his new school as well. He enjoyed going to the beach and flirting with the women and girls, learning their language, as well as making the most of their rewarding non-western culture. The house had many different staff. Apart from cooks and cleaners, Oscar also had to have a Nanny. While at first he was not too thrilled about the idea of this, he then felt intrigued to learn that this Nanny was an 18 year old young woman who was also one of Brazil's most renowned models, and he had seen her in some of the country's best modelling magazines. Oscar was 12 now, and his desire and attraction to women and girls had only become more intense. When Oscar finally met this young woman - Fernanda was her name - he was stunned. He immediately developed a huge respect for her individualistic personality, while at the same time acknowledged that in spite of her independence, she managed to be very sexually attractive. She was perfectly capable of having intelligent intellectually stimulating and challenging conversations with him - yet somehow this juxtaposed with her perfect coolness and collectedness with the demanding profession of being a model in a way that Oscar thought surely must be very rare. Oscar, as usual, used his charm and wit, good sense of humor and manners to engage with Fernanda as much as possible. They enjoyed going to the beach and swimming together, going to movies, going to museums and having food together. Slowly but surely, he began to question her more and more about her profession. He developed a real respect for her as he learnt that while it was rewarding in that she knew she was admired physically, the profession also had its real challenges. It was a survival of the fittest profession with a lot of real pressure, and Oscar developed a real sense of admiration with Fernanda's determination and motivation to succeed against the odds. Gradually, Oscar became more and more interested (but gradually and carefully) in the sexual elements of Fernanda's life and profession. He found Fernanda was remarkably open about her sexuality, and learnt that in high school she had had some boyfriends who were several years older, and had worked hard to ensure she was very attractive with these young men and gave them an awesome experience. Oscar was also fascinated at how she seemed to grow up with no sense of taboos around sex, and Fernanda explained that in her culture that was much more possible to do so as the society is much more indifferent and likely to mind its own business. She said she had been to Bahia a few times for the Carnival and found its real sense of open-ness had been refreshing, and she felt really at home there. Their relationship took a turn past the point of no return, once their conversation had developed to where Oscar was asking if Fernanda had ever had sex with someone younger. Oscar said: "So how old was he?" Fernanda said "Well, he was quite a bit younger. I was a teenager so it was quite an experimental time and I was looking to develop myself as a model." Oscar was intrigued by this. "So how many people were you having sex with back then, and how much younger was he?" Fernanda said "Well yes I mean you have to understand I was having a big sex life even then, and most of the guys were my age or older. However I did have a bit of a sweet spot now and then for guys who were younger". Oscar got a little excited and wondered if this could be a sign. "Okay so how much younger? I don't mind, I had girlfriends in kindy so I know what you're talking about" he said with a grin, in a hope to make her feel more at ease. Fernanda laughed and said "Aww, that's cute. Well yeah although we didn't really do too much, I did get to have an experience with a 9 year old when I was 14. We just fooled around a bit and I sort of felt good impressing this young boy that I was a good model." Oscar's face lit up with excitement. "Wow, that's awesome!" he said. "Lucky 9-year-old. What did you do together?" Fernanda laughed and blushed and said "Oh, well we just got naked I suppose and I gave him a lap dance and we did a few other things. Not the most I've ever done with a guy for sure, but I wouldn't mind doing it again some day." Oscar was now trembling with excitement and his heart was stirring. He knew very real possibilities were developing and while he was nervous, it was a controlled nervousness and he kept his cool. Fernanda, who was good at observing this in males, said to Oscar "Would you like me to do something really special for you? I can give you a lap dance if you want. Since nobody else is here, I think that could be fun. You're a cute guy, I'd let you do anything you wanted." Oscar knew this was it, and agreed immediately. They went into the back bedroom and Oscar sat down on the double bed. As they walked he knew he could now touch her all he wanted, and gave her ass a little friendly pinch as they walked together. Oscar sat down on the edge of the bed, fully clothed, and Fernanda patted him on the shoulders and said "Just relax, little boy. You're a good guy, I'm a good judge of character. Just enjoy yourself." And so it began. First, Fernanda began to dance around just wearing her clothes - a fashionable tight shirt and a short skirt. She wiggled her hips and did some pelvic thrusts, lifted up her skirt and just generally made Oscar feel appreciative that he's got a girl who's willing to have fun with him. Then she took her shirt off and Oscar felt a more intimate thrill as he saw her bra and bare tummy. She rubbed her bra in his face and told him he could do what he wanted with her, which made him feel full of content and pride. She then unbuttoned her skirt and humped Oscar's clothed crotch wearing only her panties, and Oscar felt his heart pounding and he was gasping as he came to terms with the implications of the experience. Then finally she took her bra off and he got to see her big breasts, and she held them out to him and he rubbed them, feeling totally illicitly pervy but very content like any mischievous little boy would. Then she took off her panties and humped his crotch, which culminated the peak of the boy's sense of fulfilment and awesomeness, having a naked lady dance on him. She then danced by wiggling her ass in his lap on top of his clothed bulging crotch and he felt awesome and vindicated with pleasure. She then gave him a kiss on the cheek and said "I hope you liked that as much as I did." Oscar said "Believe me, I did" and grinned. Fernanda said "Now, just because you're such a special boy who likes me so much, I would like to finish off by giving you a really special experience, if you're up for it." Oscar said "Oh yes, anything you want," feeling excited. Fernanda said "I bet you have a real nice boyhood, Oscar. I would like to give it the worship and pleasure that it truly deserves, with one of my awesome blow jobs." Oscar said "Sure!" barely managing to contain his sense of pride and excitement. Fernanda came up to Oscar and started slowly unbuttoning his zipper. Then she rubbed his smooth thighs and tighty whities and felt his bulge and patted his head and said "You're going to make someone very lucky with this one day, my little young friend". Then she slowly slid down his undies and although she was a remarkably cool and collected person, Fernanda couldn't help but being stunned and impressed by Oscar's boyhood. At 12, it was still totally hairless, but remarkably large and uncut. It was fully erect, and Oscar lay down on the bed and Fernanda began to perform what she did best. First, she kissed it, over and over, several times - fully acknowledging how awesome Oscar was and how lucky she was to be privileged to experience such a wonderful boyhood. Then she began to alternate the kisses with licks and explored his hairless ballsack as well as ran her tongue up and down his shaft. Then, finally she took the whole package in her mouth, ran it in skilfully and deeply, and Oscar began to moan loudly in excitedness and fulfilment at having his boyhood being worshipped and admired so much by one of the prettiest women he'd ever seen. The sense of pleasure and fulfilment he was experiencing he felt was just out of this world, and he trembled and gasped deep breaths as he felt his boyhood being skilfully and thoroughly worked upon and worshipped. Finally, he felt the familiar feeling which he had already been experiencing so long, rush to him with a force. His body tensed up and he shut his eyes and clenched his teeth, and had a dry orgasm inside Fernanda's mouth. Fernanda thought this was really cute and made sure she thoroughly swirled her tongue around Oscar's pre pubescent hairless penis to savor all of his boy juices as much as possible. Oscar and Fernanda had now fallen truly in love with each other. They spent the next several months getting to know each other fully, going camping together and cuddling and sharing secrets. Both of them had had fascinating lives and had much to show off to and learn from each other. But it wasn't long before Fernanda felt she needed to give Oscar one more treat and reward to make their relationship complete. She decided she would do it for his 13th birthday. On his 13th birthday, when they had some time alone together, after Oscar had finished his birthday dinner and pieces of cake she had made for him, she came into the room and announced the surprise. While patting his shoulder and rubbing her fingers through her hair, she said: "Oscar, I feel bad that we haven't made love yet." Oscar froze. He knew that he wanted to do this badly, but for some reason he had always kept it in the back of his mind and assumed it was only going to happen at some distant time in the future. "Really? You mean it?" Fernanda said: "Sure, I mean it. You mean the world to me, Oscar, you're so little but such a ladies' man. So respectful and intelligent, interesting and beautiful. I want you to do it." Oscar couldn't quite believe what he was hearing. Was this really going to happen? Fernanada took him by the arm and they walked together, perhaps slowly and ceremoniously to the back bedroom, which had a double bed, heart-shaped pillow and silk sheets. Fernanda put his arm around Oscar and said to him: "Oscar, look - you're about to have sex with a girl for the first time. I don't want you to worry too much about the implications, I just want you to have a good time. There is nothing wrong with sex, you and I love each other more than anything, and if there is one thing that is for certain, it is that we were meant to celebrate this love together. You can do what you want to me, lets just have a good time." Oscar took his shirt off revealing his still hairless nipples, chest, stomach and armpits. He then unbuttoned his jeans and took his pants and undies down. His penis had now grown a little, it was about 5 inches and seemed to be in the middle of the growth of its length. It had a few pubes, although not much. Fernanda lay down on the bed against the wall and squatted with her legs apart and spread her pussy apart, saying: "I'm all yours, my sweetheart boy." Oscar took a deep breath, came forward and closed her eyes. He leaned forward and Fernanda took his erect boy penis in her hand and lined it up with the entrance to her vagina. She said: "Fuck me boy, just push into me." So Oscar pushed forward and found himself inside her. It felt quite a lot tighter than he had expected it to be, but it was very accommodating, warm and moist. He suddenly realized that now that he really was fucking a woman, this was it, he really had stuck his penis in a woman's vagina and nobody could call him a virgin any more, even if they did just define it by male to female intercourse. He tried to keep it as deep in her as he could, and thrust his hips backwards and forwards while Fernanda moaned in ecstasy. "Oh!! OHH!!! Oscar you're a real boy. Do me!!" Oscar realized there was no turning back now and started developing a good rhythmical force by moving back and forth faster into her vagina. In his excitement, he started moving faster and faster as the disbelief of the situation he was in gave way to a desparate recognition of his attempt to gain the most from the best experience life had to offer - sex with someone he loved. He went harder and harder into her pussy. Fernanda moved with him and truly found herself caught up in excitement as well - this boy really was good at giving her pleasure, perhaps quite a bit better than even a lot of older men were. Suddenly Oscar let out a gasp and said: "I'm gonna cum!" Fernanda said "Ohhh god, do you want to cum on my tits" Oscar quickly took his penis out of her vagina, pushed his body forward and ejected his sperm out of his penis all over her big tits. The cum trickled down and around one of her tits. He rested his penis in between them for a moment as he came to the full realization of what he had done. Then Fernanda reached out and gave him a pat on the shoulder. "Trust me Oscar, that was worth it. I will never forget how special you are, for the rest of my life." Oscar felt happy with this conviction and lay naked in Fernanda's arms eventually falling asleep while she rubbed his hair. Their relationship had been wonderful and they had done many things together, and they continued to make love several times. Eventually though, the day came which both of them had had in the back of their mind - Oscar's family had to continue their travels and their relationship had to come to an end. Oscar and Fernanda agreed to keep in touch, which was easy as his parents still considered her a friend of the family as they recognized she had been a good influence on their boy. They said their farewells and Oscar began to continue his life of travels, and they kept in touch regarding both of each other's interesting and challenging but fulfilling lives. While Oscar certainly never forgot his fulfilling sexual experiences of the past, he was the type of boy who always loved to embrace new experiences of the future. When he was 14, he went to a party with some older friends and for the first time, he got to fuck a 19-year-old girl in the ass. He really enjoyed this experience, though perhaps in a more sleazy, pervy and more masculine experience than some of his previous experiences. He enjoyed bragging about his experiences to his friends, some of which were older but had still had less experience than him. Then, later on at age 14, his family flew with him on another work venture to once again, a luxury accommodation in Thailand. There, Oscar once again enjoyed the luxury setting as well as the food and culture. And it was there that perhaps Oscar found his most meaningful sense of identity yet, with a certain experience with a 50-year-old man and his younger 20-something year old female Thai partner. While he enjoyed a return to the experience of being fucked and worshipped by an older man, he also got to have a new experience, of fucking his partner while being fucked by the man at the same time. This experience he found was really important in cementing his identity of simultaneously being a real stud and a womanizer, while also being homosexually inclined towards adult men and fully capable of appreciating being worshipped by them. He carried this identity forward into his future life.