Chapter 2: The History of Ryan - Part I: The Good Luck and the Bad

Ryan Sheaffer seemed to be a ridiculously fortunate young man. He was born to self-made multi-millionaires David and Ellen Sheaffer after they had made their fortune in the real estate and investment industries, and were already in their early forties. They wanted to give their son the world; however, in many ways, having their first and only child this late in life was kind of an afterthought, once their financial empire and lavish lifestyle were fully established. David, a former Olympic swimming champion, and Ellen, a once-famous cover girl model, honestly wanted to attempt being good parents, but weren’t naturals in the nurturing roles of mom and dad. As long as Ryan was reasonably well-behaved and got good grades, they largely let him do what he wanted while they continued doing what they wanted. They didn’t mean to be emotionally neglectful; they just didn’t recognize the depths of love that parents should express to children, and did better at just “managing” their son while they continued with the obligations and indulgences they were accustomed to.

Usually, that suited young Ryan just fine, as he had a bold, independent, charismatic personality. As a child, he had some subconscious insecurities about how much his parents really cared about him, but overall he was not unhappy. He always had a nanny, a chauffeur, a tutor or whoever else he needed at various ages. His parents did love him and tried to be involved in his life, though they usually spent just the minimum amount of time and effort on him to make themselves feel like they were fulfilling their parental obligations. As long as he was “doing fine”, they were pleased and went about with their busy, rich, grown-up lives.

Even he would admit his life was still pretty damn good. He always had the best toys and clothes, top-of-the-line lessons and coaches, went to the very best summer camps, and got to go on incredible vacations all over the world. He was naturally athletic like his father and became a formidable contender in tennis, track, swimming and basketball, and also enjoyed dancing, volleyball and golf. He was a pretty sharp kid, and as he became a teenager, developed a cocky, bold, “leader of the pack” type of vibe ... kind of an asshole in some ways, but with a wicked sense of humor, and more self-confidence than anyone around. He made friends easily because everyone wanted him to like them, and there were always more girls interested in him than he could count.

One reason for that was that on top of everything else, he was blessed with incredibly enviable, sizzling hot good looks. Truly. He had a lean and toned physique, an extremely handsome face (some would call it beautiful), medium blonde hair and deep blue eyes, and could put most Abercrombie & Fitch models to shame. His mother knew he had “the looks” and got him started in modeling in his younger years, and by the age of 9 he had modeled childrens’ clothes and swimsuits on many runways and in several catalogs and websites. Through his mid-teens, he still did some work as a teen sports model, but eventually ran out of time for it when sports, girls and other interests began dominating his life. However, he had become very calm, casual and self-assured about his looks, both with and without clothes. Whenever any friends or parents were taking pictures at any event, he was always the most willing to jump in front of the camera and ham it up. He was usually the first kid to take off his shirt at any event, game, or gathering with his friends. At the beach or at the pool, he was often the only boy who wore a speedo, and he loved that distinction. He couldn’t help knowing everyone thought he was gorgeous, and learned to capitalize on his looks everywhere he went in both subtle and not-so-subtle ways.

Being frequently left to do as he pleased, Ryan started exploring sex when he was barely 12. He hit puberty a little earlier than most other boys, and by 7th grade when PE required showering with all the other boys, he easily secured his status as the alpha male in the locker room. He frequently caught other boys glancing or even staring at the nice size and length of his penis, and flaunted it a bit, loving the attention. Heck, he himself admired its new, fuller, manly shape, large head, and big, descended, plump balls. This was the age when everyone started beating off a lot, and at a young 12, Ryan was one of the first to shoot real cum. He demonstrated this for his friends several times, earning their envy, their respect, their desire to “be like Ryan,” and their requests for his advice on how to jerk off. Shortly after that, he discovered porn and learned about a thousand things he wanted to try, and got lots of info and advice from Andrew and other older kids he knew. Ryan began pursuing getting girls to suck on his cock, and after his ecstatic babbling to his friends about how fucking awesome THAT was, they followed his lead and pursued it themselves. The girls in his class continued vying for his affection, and several became eager cock suckers in order to earn his favor.

He gleefully lost his virginity just a few weeks before he’d turned 13, with the 16-year old daughter of one of his parents’ friends. They had been shuffled up to his quarters during a dinner party at his house, and Trina couldn’t resist the opportunity to be this cute little future stud’s first lover. She offered herself to him as his first, and taught him several things over the next few hours. Ryan got so carried away with this turn of events that they narrowly escaped getting caught by their parents later when it was time for Trina to leave. He was ecstatic that she had opened up this whole world to him, and the day after his birthday a few weeks later, she and one of her girlfriends got Ryan over to her house on a Saturday and tag-teamed him all day long. Young Ryan was overwhelmed with pleasure and ran himself ragged that weekend, not knowing what his limits were or if there even were any.

That clinched it. Ryan was instantly infatuated, and took to sex like it was the missing air he needed to breathe. His hormone level shot through the stratosphere, and over the next couple years, he became a sex-crazed teenage walking hardon with an insatiable sexual appetite. Due to his somewhat standoffish parents, there was a needful longing for physical intimacy deep inside him that he had never even recognized himself, but he never played the desperate horndog ... he already had a sense of how to make the sex come TO him, by never letting the girls fully know how he felt and making them come after him. And they did, by the dozens. He was rich, hot, young, horny, better than all the other guys, sort of a prick, but incredibly hot and desirable, even in junior high.

All these hot girls around him suddenly became objects of desire instead of just flirtatious friends. He had to find ways to have more of this exquisite new pleasure called SEX. By age 14 and 15, his overpowering libido resulted in him simply needing to cum several times a day. As often as possible, he accomplished this with a girl, but sometimes it required jerking off 5 or 6 times a day too. It seemed he could never get his cock to stay down very long.

By age 16, Ryan had an intense, almost obsessive interest in perfecting his skill and stamina in love-making – it was something he strove to be really, really good at. He studied sex books and websites extensively, and tried numerous nutritional and aphrodisiacal supplements. He and some friends studied and experimented with all kinds of techniques for achieving multiple orgasms regularly. Even when he wasn’t fucking, he spent many long nights whacking off, repeatedly practicing the muscle control and perfecting the stamina and drive needed for being a multiorgasmic superstud of a lover. He loved how each orgasm seemed stronger and more intense than the last, and his strong aerobic and athletic conditioning helped him have the stamina for achieving it. He took great delight in forcing himself to push beyond limits for more and more orgasmic delights. He also developed a tremendous infatuation with eating pussy, and pleasured many girls in ways no one would ever match. He learned rhythms and stroke techniques with his cock, and developed a keen sense of how to make a girl have the strongest, most earth-shattering orgasms possible, over and over.

He also continued his infatuation with his own looks and charm. He couldn’t help but be naturally lean, almost skinny, but he compensated for it with an intense love of exercise. Vigorous sex was certainly great exercise, but he also grew to love an hour in the weight room 3 or 4 days a week, as well as running, swimming, and playing sports. He loved posing for himself in the mirror, examining the nice, smooth muscles he developed, and celebrating his perfectly sexy legs and ass, well-defined 8-pack, firm but not-too-bulky pecs, shoulders and biceps, and his nicely-defined back. He loved taking his own pictures and video of himself naked, especially his beautiful cock both hard and soft, and even posted his own jerk-off videos on line, with his face hidden due to his age.

Few teens were as girl crazy as Ryan was; the more he had, the more he wanted. However, halfway through high school he also began to acknowledge his attraction to boys as well. At first, he just assumed that his love and obsessive admiration of his own gorgeous body also transferred into an intense lust for other gorgeous male bodies too ... but then he also relished knowing that gay boys always were attracted to him.

A fellow teen model named James was the first boy to suck Ryan’s remarkable 15-year old cock one night in the changing room after a long photo shoot. Ryan had been finding less and less time and interest in modeling for a few months, but was drawn back to this one photo shoot ... not just because it was a pretty exclusive and highly-anticipated new line of swimwear, but also because he was especially impressed with his body’s development and growth that year and wanted to see it photographed now. James was actually a year younger than Ryan. As is common for hot young people in their industry, he had also lost his virginity very young and had scored with more than a dozen girls already ... but he had come out as (mostly) gay several months ago and had had sex with many boys since then as well.

The two young studs, along with four sizzling hot teen girls, had just spent several hours posing with each other in swim suits, speedos, spandex biking shorts, etc., and James had seen Ryan struggling to keep his already-bulging soft cock from popping a large boner the whole time ... which was tough to do when you’re 15 and accustomed to having several orgasms a day. In the locker room, Ryan had hurriedly ripped off his last tight little briefs to free his cock, and let out a sigh as he collapsed on a bench against the wall. He and James both giggled a little at that ... and before he knew what to think, James knelt between his legs and engulfed his cock. Ryan found himself ecstatic and excited by this, not repulsed, as the remarkable young model boy orally worshipped his cock. James sucked him to orgasm very quickly, and then peeled off his own swimsuit and straddled Ryan on the bench and pressed the length of his cock along that of Ryan’s. In his hand he grabbed both shafts, which were well-lubricated by Ryan’s cum, and stroked them together while kissing Ryan deeply. Ryan’s hands reached around James and freely felt the hot male flesh of his whole incredible, 14-year old body, and soon the boys both shot copious amounts of cum between their heavily-breathing chests. They jerked each other off once again in the showers.

A few days later, Ryan invited James for a “sleepover”, which turned into a long, intense night with no actual sleeping, as Ryan satisfied some long pent-up desires he hadn’t even realized were there. He learned to suck cock like a pro, and was introduced to the pleasures of both giving and receiving anal sex. It felt a little weird at first that there was no girl involved that whole night ... but the lust and satisfaction Ryan felt the whole night reassured him that he was equally happy with this boy as he was with a girl. He spent the next few days imagining the pleasure of being with a girl AND a boy together, and watched pornos and read accounts of MMF threesomes, MFF threesomes, and all kinds of other combinations.

It was Ryan’s nature to indulge in whatever pleasure he wanted, so from then on, he was very comfortable with his bisexuality, though most people knew nothing about it. Perhaps around ¾ of his sexual conquests were still with girls, and he could be completely satisfied by them in all ways ... but he had little hesitation when an opportunity presented itself to grab some hot male flesh once in awhile either, and with his “pretty boy” looks, plenty of “opportunities” presented themselves. As often as possible, Ryan “recruited” partners of both sexes to join him in threeways, which became his favorite way to spend several hours any evening he could arrange it. Ryan especially loved being sandwiched between them with a cock pumping in his ass while his own thrust in and out of a hot pussy.