Portraits

This is a work of fiction, although with real people as inspiration for some of the characters. It is a coming of age romance between two boys who are total opposites. Like real-life real romances, the characters are not usually superficial, and the romance requires patience. Enjoy! Feedback welcome at bobby718500@yahoo.com

A Boy Named Shawn

Shawn was the second child of two eccentric, but loving parents named Lance and Jenny. At his Italian-background parents' insistence, Lance attended Santa Clara University and reluctantly received a rigid traditional Jesuit education. Fortunately, despite being viewed as one of Santa Clara's most non-conformist students, Lance was encouraged by his faculty advisors to pursue his passion for painting and drawing. Nor was he prevented joining a group of friends who played acoustic guitar sets of Bob Dylan and other "protest" folk songs in the student center.

Shawn's mother Jenny had been raised in San Francisco in modest circumstances and she was the first person to attend college. She financed her education at San Francisco City College as a hair stylist, having received vocational cosmetology training in high school. While Jenny thoroughly enjoyed cosmetology, she majored in secondary education with several subject concentrations, vowing to be like several of her high teachers who encouraged her individuality and freedom of expression. Jenny was uncommonly pretty with delicate features. She would have looked equally as good as a debutante as she did with her hand-embroidered jeans, tie-dyed shirt and long free-flowing golden hair.

Shawn's parents met in the art flea market outside a Grateful Dead concert. They were both admiring the watercolors being sold by a middle-aged man that looked a bit like Jerry Garcia would look twenty later. Transfixed by the art, they literally bumped into each other browsing as they moved in opposite directions down the row of renderings. Both comparatively conservative in appearance given the "hippie" styles of the day and the event they were at, there was instant attraction, not surprising since both were blessed with inherent good looks. While both were quite slender, they were otherwise opposites, with Lance having olive skin and brown hair, while petite and waifish Jenny had Nordic features with striking blue eyes and naturally blond hair.

After a year of a commuting love affair, Lance and Jenny were married the following summer. Instead of immediately entering the workforce, they spent the rest of the summer following the Grateful Dead, setting up a small market space and displaying some of Lance's small oil on canvas pieces. Lance and Jenny made just enough money selling art to break even on expenses until they began their respective careers in San Francisco, as a commercial illustrator and an inner city high school English teacher.

After trying for several years to conceive, their daughter Sheila was born. Sheila primarily inherited her father's features with beautiful brown hair and green eyes. Lance's career as a commercial illustrator never flourished financially, but it had regular hours, so he had time to be immersed in Sheila's life while continuing his painting on the side. He, of course, would have loved to make his living only being an artist but financial realities dictated otherwise. Jenny's earnings as a teacher were barely enough to cover the costs of Sheila's childcare net of expenses, so she "retired" from teaching. As Sheila started primary school, Jenny began making money on the side as a part-time hair stylist at a salon near their Twin Peaks area home.

The whole family was enthralled when Shawn was born. He was an "accidental" baby, being almost five years younger than his older sister Sheila. From the outset his face could only be termed "beautiful". Physically he was a mixture of his parents, being quite petite like Jenny, but having a lighter shade of his father's olive skin. Instead of brown eyes like Lance, Shawn had riveting blue eyes like his mother with unusually long eye lashes.

Quite blond like Jenny as a baby, as Shawn grew older, his hair became light brown with natural highlights. While both parents were physically attractive, both of their children had received uniquely fortunate combinations of their physical traits. For the most part, both children also stayed out of trouble, and were "pleasers" in personality. Jenny and Lance were openly affectionate and remained deeply in love. It was a happy, albeit somewhat eccentric, household.

Lance continued to pursue his art on the side and would occasionally display his works at local art festivals. He became close friends with the owner of a local art supply store who was nearing retirement. Scrimping and saving, Lance eventually bought the original owner out when he was ready to retire. While Lance enjoyed owning his own business, it was hard work and ultimately was no more lucrative than his job as an illustrator. Owning the store, however, did keep Lance engaged with other artists and in slow times he would work on his own painting in a small studio in the back of the store. The store did allow enough flexibility to remain greatly involved with his children, and the children enjoyed coming to the store and keeping their father company.

Similarly, Jenny developed quite a following at the salon where she worked and eventually she and another stylist opened their own boutique, which became as much of a passion for her as the art supply store did for Lance. Over time it became quite trendy to be a client of the salon. Jenny and her partner resisted the urge to open more locations or expand the store; choosing instead to cater to clients who were willing to pay more for their service. They did add a manicurist who came in everyday and on Thursday thru Saturday, different makeup artists would come in and help "doll up" socialite clients for their parties. Sheila and Shawn also spent many hours in Jenny's salon, for baby-sitting if nothing else; and later Sheila worked part-time as a receptionist.

In idle times at the art supply store, Lance began a tradition of painting a modest-sized portrait of his kids about every other year. The portraits were unique in Lance's style in that they were not painted from a pose or a photograph. Thus, the portraits did not copy all of Sheila's and Shawn's features exactly, but rather incorporated how Lance visualized them in his mind. The paintings eventually ended up ended up in their hallway at home, although Lance would hang the most recent production behind the store counter until he painted another one. It was his equivalent of keeping pictures of his children on a desk like many people do at their offices. At the store the portraits of his children drew many comments from customers who were taken by both Lance's talent but also the inherent beauty of his children.

As Shawn got older, his hair was thick and had rich body, and Jenny would cut it periodically to keep the ends healthy. There was nothing remarkable about the style Jenny provided to Shawn, simply a part to one side and then brush out the hair on the sides and back. However, even when cut relatively short, Shawn's beautiful hair drew many comments, especially from Shelia, who good naturedly teased him about having prettier hair than she did. Shawn's family reached a consensus to leave his hair relatively long when he was a toddler. Later, when Shawn's opinion was considered, he also liked wearing his hair longer, notably influenced by Sheila's preferences. Both parents never tried to impose traditional gender traits such as macho sports or on appearance to either of their children, and Shawn and Sheila gained self-confidence from their parents' philosophy.

Besides drawing on a sketch pad, Shawn's favorite things to do were to hang out with his parents at either the store or the salon and anything Sheila was doing. Shawn did not have many natural playmates as the family lived in a compact row house on between the Twin Peaks, Castro and Haight-Asbury districts and there were not many other kids his age. By the time Shawn was entering elementary school at a diverse inner city school, Sheila (an academic prodigy from the start) was a scholarship middle school student at a prestigious private day school.

Especially, considering their age difference, the siblings were always personally, with Sheila including young Shawn in many of her games and activities with her friends from school. Shelia also let him tag along when she and her friends would go to the movies or go to the mall. He would sometimes act annoyed if the movie was a "teen chick" film or if the girls spent too much time at any store looking at clothes. Shawn, in fact, love all of these activities and feigned annoyance to entice Sheila and her friends to go play video games at the arcade with him, or buy him sweets.

Shawn was the furthest thing from a brat and had an upbeat personality, so even Sheila's friends enjoyed having Shawn as a tag-along on their shopping sprees. In turn, Shawn began paying closer attention to the clothes the girls were choosing and he would offer his opinion as they chose from the different items. He had a naturally good eye for what looked good on each girl. At some point every gathering, the girls would have a long illogical discussion of the various cute boys they had crushes on, many of whom they would see at the mall. Shawn listened to these dialogues with excitement and longed for the day when he was old enough to have crushes like these. Shawn eventually realized that what he was jealous of was the attention the girls were getting from cute boys, and hoped someday cute boys would pay attention to him.

Attending public elementary school in inner-city San Francisco was a difficult time for Shawn as he was picked on by some of the rough, inner city kids because of his diminutive size and delicate features. He was called a sissy and faggot long before he had any concept of what the terms meant. Fortunately, Shawn's "pleaser" attitude served him well and his teachers adored him. Eventually, he was able to enroll in "magnet" program at the school which did not insulate him from bullying at lunch or on the playground, but where he was encouraged in his art and creative writing in smaller class settings. Shawn never complained, but his parents were greatly troubled by harassment he endured and the lack of appropriate friends.

One August before school started, Shawn asked if he could get a crew-cut instead of wearing his hair down to the base of his neck as had been the case nearly his whole life. Shocked at the thought of Shawn's beautiful hair being cut, Jenny and Lance (who had stylish collar-length hair) relented when they realized it was Shawn's way of trying to reduce the harassment he endured at school.

However, before scheduling the hair cut, Jenny looked into the requirements for home schooling Shawn, and given her background, it was a non-issue. Jenny and Lance then asked Shawn if he would like to go back to the public school, or be taught primarily by Jenny in the mornings and odd hours in the back office at the salon. Shawn immediately jumped up and hugged his parents with this possibility. The idea of cutting his hair short was never brought up by Shawn again.

Shawn thrived under Jenny's tutelage and was a grade ahead of his class in testing after only 18 months. Other than family vacations and holidays, he studied year-round, but Jenny never made him work too hard in any given week. They would start the day with intense academic work first thing in the morning and by noon Shawn was mostly working on his own on assignments, drawing or relaxing. In the afternoons, Sheila was working part-time at the Salon and she also was able to help Shawn with his work. Several afternoons a week, Shawn would go to art classes and he also enjoyed a gymnastics class which added a little tone to his lithe frame. By the time he was in middle school grades, he had met a few boys from the art classes and gymnastics classes that he called friends. However, he was still a bit shy and would have been really lonely without his family and Sheila, in particular.

Sheila continued to include Shawn in as many activities as possible, and by the time he was finishing middle school, he literally had become a virtual clothing consultant to Sheila and her friends. In idle times at the salon, he would look at the ads in the fashion magazines in the waiting area and visualize what types of things would look good on his "girl friends". Ironically, it took great urging from Sheila and her friends to get Shawn to dress more stylishly. Usually he wore non-descript t-shirts and sweatshirts with jeans or shorts. Shawn did not have as many teenage boy role models to follow in attire so the girls tried to get him to try on things when they were shopping at stores like Abercrombie or Pac Sun.

Eventually he wore more hip attire, even though he often had to buy children's or girl sizes to fit his scrawny five-foot tall body. Eventually Shawn caught the bug and enjoyed buying clothes for himself, but was just as likely to find items at a second-hand store and particularly loved shirts brighter colors that he would combine with snug Abercrombie jeans. He was so thin he had enough trouble keeping regular pants from falling down, so he avoided baggy cargo pants worn by so many other boys. Shawn never demonstrated any great interest in team sports or other typical activities. But being from this was nothing of concern to his family. They loved him dearly and wanted to encourage him to embrace whatever his natural tendencies were.

While at a Claire's store, Sheila noticed Shawn looking at a display of earrings with a sign showing a boy with pierced ears. Across the store, Sheila discreetly called Jenny on her cell to ask if it was okay for Shawn to get his ears pierced. Jenny immediately said Shawn could do whatever he wished. When Sheila approached Shawn and asked him if he wanted to get his ears pierced, he initially looked embarrassed and said no. When Sheila told Shawn that their mother had already said it was okay, Shawn smiled ear-to-ear and twenty minutes later left with a starter set of studs in his ears and a set of small gold hoops in a box.

At Sheila's suggestion, Jenny trimmed Shawn's shoulder-length hair to a uniform length just below his collar, with fringe that swept across his forehead. Jenny also added contrasting layers to his previously non-descript hair and taught him how to use a blow-dryer and curling iron to add more definition and waves. Shawn became adept at styling his naturally beautiful hair into a brushed out look. Even though his hair was considerably shorter, it could still be pulled back into a high ponytail if he did not have time to style it.

During her senior year and Shawn's 8th grade year, Sheila had settled in with her first serious boyfriend. Shawn thought he was very handsome, but still thought Sheila could do better, an opinion he would have about most of her subsequent boyfriends. Between living in a liberal city like San Francisco, television and the internet, Shawn was not naïve about sex and sexuality by now. He had also gotten the obligatory "birds and bees" speech from Lance two years earlier. Shawn would wait up late for Sheila to come home from dates so he could hear all the "details". Like the best friends that they were, Sheila would confide everything to Shawn, and he listened with rapt attention. Sheila's detailed stories of kissing at the beginning of the summer, migrated around the bases to home plate by the end of the summer.

Sheila's progressive descriptions of French kissing, getting felt-up, hand-jobs, oral sex and then intercourse made Shawn's insides churn. It became obvious that he had far greater interest in what it was like to have sex with a boy, than the other way around. Shawn was anxious to know what her boyfriend liked best when she gave him a hand-job or blow-job. Sheila sheepishly admitted that she had learned to enjoy swallowing when her boyfriend came and Shawn wanted to know everything about the taste. Shawn fantasized and masturbated to thoughts of being in the arms of some handsome boy doing the same things as Jenny and her boyfriend.

If anything the sexual discussion made their relationship even closer. Close enough that Shawn readily admitted to Sheila that "yes" he thought he was gay. With Sheila's encouragement, Shawn found an appropriate moment to tell his parents. Shawn was not sure what to expect, but the coming out was very anti-climatic, since neither parent said hardly anything other than "whatever makes you happy makes us happy", "be safe" and "let us know if we can help".

Shawn had no reason to doubt his parents' acceptance, but it was still a relief to unburden his mind with the revelation. From that point forward, he felt even less pressure to conform to heterosexual/masculine stereotypes and was proud to identify as being gay. Unfortunately, Shawn was not generally around other openly gay boys his age, and he only found himself attracted to his opposites...straight looking and acting which made it hard to identify potential companions.

Meanwhile, Lance received nice compliments from his co-workers and regular customers every time he hung a new portrait of Sheila and Shawn at the store. The newest portrait on the left depicted a beautiful dark-haired girl wearing stylish reading glasses peering down as if in deep thought. On the right, was a tan, innocent face emerging from a grey background with shadows falling across cheeks and satin hair, but with rich blue eyes emerging from the shadows.

High School Growing Pains

The summer before Shawn's ninth grade year was the best of times and the worst of times for Shawn. It was bad because it was Sheila's last summer at home before she left for college. However, Shawn stayed busy with things he enjoyed. He alternated working part-time at the salon in the afternoons and at the art supply store on the weekends. He enjoyed both jobs, but he liked the salon the best. Shawn would fill in for Jenny as receptionist if she was not there; he would sweep the floors and attend to the ladies (and occasional man) in the waiting room; and he would keep all the supplies refreshed. Being bright and curious, he learned by observation what most would need to go to cosmetology school for. His mother would answer his frequent questions about the techniques she was using to create a particular style. He also loved talking to the customers and all of the salon's longtime clients adored him.

There was a very talented new makeup artist named Josh that patiently explained all the nuances of applying makeup and let Shawn assist him. Josh truly was an "artist" in his ability to maximize a face's beauty and he became a magnet for new clients to the salon. Josh was stereotypically "flaming" with a stylish buzz cut, tight jeans and tank top covering his thin body. Josh also had multiply-pierced ears and wore mascara at a minimum every day. Josh was so campy and funny that he had the whole salon laughing most of the time. Josh was usually picked up from work by his boyfriend Jake, a stocky cabinet maker who drove a Harley. Shawn always noted how happy Josh and Jake seemed as they drove off with Josh's arms' tightly around Jake, simultaneously hugging and holding on.

Jenny was getting ready to attend Williams College on the east coast on a partial academic scholarship. Shawn could not stand the thought of her being gone. But, before she left that summer, Sheila introduced Shawn to a several boys his age from her private school that were part of a gay, lesbian, and TG support club. Sheila's school prided itself on being "No Place for Hate" and diversity sensitivity of all types was embraced and enforced. Given Jenny's favorable experience at the school, Jenny and Lance asked Shawn if he wanted to apply to attend the school, but he was not interested in the least. He had grown to love his life that revolved around his family, his art classes, gymnastics and most of all getting to work at the art store with Lance and the salon with his mother and Josh. Plus he was actually ahead of people his age in academic work and he did not want to regress.

Fortunately, Shawn began to make friends as the boys from the school group invited Shawn to all of the group's social events. Initially, this involved nothing more than a group outing to the movies or performing arts, but there was also a gay-friendly school dance each semester that Shawn attended as a guest. Interestingly, there were hardly any paired-off "couples" within the group, and while Shawn enjoyed the excitement about being around other gay teens, he was not attracted to anyone in particular from the group.

As they got older, members of the group found time for normal teenage discoveries, just like their heterosexual counterparts. In the innocent stages, this involved games like "same-sex" spin-the-bottle or truth-or-dare. It was during one of these games that Shawn kissed his first, second and third boy, each game taking it a little further in terms of "tongue-exploration".

Later, he went with a group of boys to one of their houses where the parents were away. On this occasion, Shawn had his first beer, his first Red Bull with vodka, and his first toke of weed. There was a PG-13 orgy of sorts as the boys took turns making out with each other in the game room. Eventually this led to everyone masturbating in front of each other. The next time the house was available the boys progressed to giving each other hand jobs and by the third occasion the group was together, Shawn both received and gave his first blow-job.

To Shawn, all aspects of oral sex were liberating and overwhelming in sensual stimulation. But none of his initial forays had the romance and passion that he envisioned when he would listen to Sheila talk about being with her boyfriend. Having said that, the first time Shawn wrapped his lips around another boy's warm, stiff penis, it was a major rush. He knew that he was truly gay and glad that he was, and his enthusiasm for oral sex was over-the-top. Remembering his sister's recommendation Shawn was one of only two boys initially willing swallow their partners' emissions, and for this they became "legends" within the group. These initial encounters lacked emotional intimacy and sometimes even privacy. However, the sessions demystified sexual contact and definitely enhanced Shawn's proficiency at pleasing another boy.

Shawn loved the power he felt when a boy seemed under his control because of his sexy appearance and the talent of his mouth. Shawn tended to be the aggressor and he would give firm instructions to his partners on when to take off their clothes and dictate whether they should stand, sit or lay down. At the same time, Shawn loved submitting himself while on his knees and let boys essentially fuck his face. It only got him more excited when they would pull his head towards them and work their fingers through his hair. Shawn felt triumph when he felt the warm rush of an orgasm hit his throat, and loved the salty-sweet "taste of success".

As much as he loved to give, Shawn also enjoyed being orally serviced by the other boys, and seeing them just as excited to be giving head. He loved to playfully "command" his partners with commands ranging from "...harder!" to "...suck it you sissy" to "...you're a good cocksucker, now take it all". If the other boy would not swallow his load, Shawn made a point of making sure he shot his ample ejaculation into the boy's face and hair, which motivated several learn the practical benefits of swallowing!

Since the other boys were also early to leave the closet, most had at least some stereotypical gay markers in their appearance or mannerisms. However, Shawn's pristine appearance was uniquely attractive to most everyone else, including some lesbian girls. Because of this, and because he was viewed to be the most expert at giving head, Shawn and was always the preferred partner in these adolescent exploratory sex sessions. Several couples emerged within the group and two boys asked Shawn to be their exclusive boyfriend, and had their hearts broken when Shawn politely declined. Shawn had not met anyone that he wished to be exclusive with and he enjoyed the diversity of sexual partners.

As he got older, Shawn fantasized about anal sex, but unlike many of the other boys, he wanted it to be with someone he cared about. Thus, as the boys got older and more adventuresome at their parties, Shawn declined to go beyond oral sex. These gatherings became available almost every weekend over the next few years, but after the novelty wore off, Shawn and a few other boys put some distance between the remainder of the boys that seemed to be intent on self-destruction.

Shawn did not really like getting too drunk, nor did he need drugs to have fun. Several of the boys began routinely doing lines of coke and inhaling poppers, while also graduating to unprotected anal sex with people they had just met. The most reckless would look for quickies in public restroom with strangers, and take wicked pleasure in picking up older straight men.

Shawn, without burning any bridges, limited his activity to more PG-13 gatherings and found friendship with the lesbian girls in the group. He also made a point of hanging out some with boys and girls his age from his art and gymnastics classes, both gay and straight. Most importantly, Shawn became much more serious about applying his artistic talent toward a longer term interest in fashion design and had a portfolio of ideas he someday hoped to formalize. Even in the summers Sheila never came home for more than a week at a time, but the siblings talked on the phone, text messaged or MySpace'd constantly.

By the end of ninth grade Shawn's "growth spurt" had occurred and at 5'6", he was one inch shy of his eventual height. If anything he was slimmer and more angular than ever, and between his perfect skin, striking features and gorgeous hair, he constantly turned heads. In Sheila's absence, Shawn became better "friends" with his parents and did not mind if he did not have wild plans on the weekends. Lance encouraged Shawn's efforts to use fashion design as an inspiration for his art efforts. Jenny also encouraged Shawn at the salon as learn much as he was interested in about hair and makeup.

One evening as she finished with her last hair client, Jenny looked over and noticed Josh verbally conveying eye makeup techniques to Shawn, using Shawn as a subject. Shawn had pulled his hair into a pony-tail to keep his hair out of his face making his ever present small gold hoop earrings clearly visible. Even from a across the room, Jenny could see how animated and excited Shawn was as he looked in the mirror. When Shawn looked up with his precise and tasteful eye makeup, she was taken aback at how much more arresting Shawn looked. Shawn, however, upon noticing that his mother was watching, quickly asked Josh to remove the makeup he had applied.

When she got home that night, Jenny stopped to look at the row of portraits that Lance had painted of Shawn. She had always loved them, but had not often taken the time to study all the details. It occurred to her that in each one and at all ages, Lance had captured Shawn's essence and striking features, without them being literal recreations of Shawn. In fact, in several more recent portraits, Shawn's hair was longer and even more styled than in real life at the time. Similarly, in the portraits Shawn might have elaborate earrings or necklaces on, that he had never actually worn.

In the most recent portrait that was in their home, Shawn's eyes had unmistakable mascara, eye liner and eye shadow, even though she had never seen him wear any before that day. It was as if Lance had always visualized Shawn different than reality at the time, but that as time passed, Shawn looked much like Lance's vision. As Jenny continued down the hall she noticed Shawn out of the corner of her eye, in his room examining himself in a hand-held mirror. Jenny then called Shawn into Sheila's small bedroom, which was largely the way Sheila had left it. She opened up Sheila's cosmetics and jewelry drawers and turned on her makeup mirror.

"Shawn, I've been thinking. Jenny is away and doesn't need any of this stuff. It is a shame to see it all go to waste. If you see makeup you want to use, or if you want to borrow any jewelry go for it. I know she would not mind. Or for that matter, don't be shy about buying things you like at the store."

"Mom, Josh and I were just having fun!"

Shawn nervously grabbed a tissue and was about to start wiping traces of the makeup off his eyes. Jenny stopped Shawn's hand before it could reach his eyes.

"It's your choice to use Sheila's things or not. But I do think your eyes look good with a little makeup. And it might be nice to wear something besides the same gold hoops every once and a while".

She then she left Shawn alone in Sheila's room, unable to see the huge smile that had suddenly draped across his face. That evening, Lance came home and the three sat down to dinner before Jenny could reveal to Lance the earlier events. Shawn had tastefully applied Sheila's mascara and eyeliner and wore a pair of her dangling turquoise bead earrings.

Lance looked at Shawn and said nonchalantly, "I really like those earrings on you. Are they new?"

"No they're Jenny's, but she isn't going to need them anytime soon."

Good thinking. I know she will be glad that you are putting her things to use."

Fully empowered by his parents, Shawn began to experiment with his look, and with Jenny's help found a number of Sheila's stylish tops and embroidered jeans that fit him perfectly and gave him many more opportunities to mix and match. The tighter the jeans, the less useful the pockets, so Shawn occasionally would use one of Sheila's leather shoulder bags to carry his things. For Christmas, Sheila gave him a leather fanny pack that had a choice of thin gold, silver, and rhinestone chains to secure the pack low on his hips. As he progressed through his high school years, he continued to refine his "androgynous hippie" look, wearing unisex clothing from Sheila's closet, unusual items from second-hand and trendy stores like Urban Outfitters and American Apparel.

Even if wearing only blue jeans and a plain shirt, Shawn usually accessorized with different, earrings, necklaces, bracelets and scarves, while enhancing his eyes with a bit of makeup. Shawn did not dress elaborately every day, and there was often no correlation to any particular occasion, but whether casual or decked-out, Shawn gained confidence in his appearance.

For the most part Shawn remained quite upbeat in personality and quite busy working with both his parents and continuing to generated fashion design ideas which he stored away for the future. In place of his gymnastics activities, Shawn substituted swimming, aerobics, yoga, and rock-wall climbing at a local fitness spa. In this and other activities Shawn met a few boys that he would "date" for three or four weeks which provided an outlet for release of sexual tension. However, he still had never met anyone who "churned his butter" enough to be a steady boyfriend. Josh set Shawn up with biker friends of his boyfriend Jake and Josh directed his way, but the comicality of those blind dates would be a story by itself. Despite not having a boyfriend, Shawn's self-esteem and assertiveness solidified with his academic success, his growing artistic fashion design skill, and from the unflagging support of his family.

Meanwhile, Lance had recently finished his most recent portraits of his children. Sheila's came effortlessly to Lance, and in it, Sheila is seen looking down smiling while holding out her arms grasping two small, child-like hands. However, on Shawn's portrait, Lance had trouble visualizing a clear picture of Shawn in his mind, and it took him weeks of stops and starts to complete. The resulting portrait, melancholy in tone, had a slightly blurred anxious face and dark apparel that blended in with the dark grey background.

Senior Year!

During the summer of his 12th school year, Jenny and Lance noticed that Shawn seemed restless and at times even depressed. Unable to get him to admit to any issues they backed off and just offered to help if he needed. Late in the summer, for about two weeks, Shawn seemed to be on a streak of consecutive days where he was dressed made-up more flamboyantly each day, and being distant and flighty in conversation. For the first time, Jenny and Lance became worried about Shawn and the decisions he might be making. For one thing, he was staying out quite late and often with new friends they had never heard of. Yet, since he was nineteen, they hesitated to impose their will too much since there was nothing stopping him from moving out if they pressured him.

The concerns of Jenny and Lance were not unfounded. Lance was hanging out with some gay party boys who were definitely pushing the limit at raves and bars they got into with fake ID's. They would start out at dance clubs perplexing the crew-cut muscle boys who wanted to dance, sing with drag queens on karaoke nights, and often end up at leather gay bars enticing the burly bikers who did not take no for an answer easily.

Out of boredom, horniness and/or loneliness, Shawn occasionally would engage in safe sexual encounters from these outings, but there was no passion in it. He devilishly enjoyed breaking down the façade of uptight or closeted young men that he would encounter. The straighter-looking, the better, as far as Shawn was concerned. He loved how he could command a hesitant "confused" man onto his knees and have him begging for more by the time Shawn had filled his mouth sprayed his face. Shawn was pickier with those he would service, and often was soothing the loneliness of someone whom he was friends with.

Far from finding a real companion, however, Shawn felt lonelier than ever and began to loathe the wilder aspects of the gay bar scene, as well as the shallow hedonistic personalities of the boys he had fallen in with. Beyond beer, Shawn did not indulge in chemicals, but some of the other boys were on a dangerous path. Shawn soon realized that he was doing the same things he had backed away from several years earlier with the boys from Jenny's school. It made him not like himself, yet he seemed to be caught in a vicious cycle, and he delved in deeper despite his misgivings.

Finally, one Saturday afternoon when Jenny was closing the salon, Shawn showed up at skimpy black leather shorts that laced up in front, and black clog shoes with two inch heels. His angular legs, not hairy to begin with, had been completely removed of all hair and glistened with moisturizing cream. He wore a skimpy dark lavender tight Bad Kitty midriff top, a thin black leather choker necklace with rhinestone studs in it and numerous thin bracelets. He wore full one inch gold hoop earrings, and had a full range of makeup ranging from foundation, to blush, to heavily made-up eyes, to lip gloss and nail polish that matched the tank top. His hair had been teased and curled with the curing iron but then pulled back into a high ponytail, with parallel strands framing his cheeks.

Being the only at the store, Jenny's first reaction was to not even recognize him, and to also be taken aback at the vixen beauty of this not a girl that had walked in the salon. From a fashion-style perspective, part of Jenny wanted to congratulate him on what all his hard work had accomplished. But even her parental laissez-faire philosophy had its limits and she also sensed a dour mood looming on his part.

"Shawn, what's going on?"

"I was going to see if Josh had fake eyelashes I could borrow? We're going out later."

"Who is we, and where is out? And I get it...you want to look like a hooker!"

Shawn was hurt by his mother's accurate insult and he stopped what he was doing and sat down glumly. Jenny came over and hugged Shawn as she sat down next to him. But when pressed by Jenny about his recent behavior, Jenny learned that Shawn was struggling with his identity. He had been going out to different bars and parties, and no matter how progressive the venue, he felt out of place, and was having trouble meeting guys he liked. While taking pride in his appearance, he had become frustrated with not looking like a macho guy that most gay men seemed to like, nor being a genetic girl or even a transgender that a masculine boy might be attracted to.

As evidenced by his appearance that day, it was easier for him to look more outlandishly feminine looking than becoming a masculine looking guy. As a result, Shawn had been experimenting to see if he would have more luck with a more extreme look to match the wilder parties and racier clubs he had been. Tonight he was planning on entering an amateur night drag show.

"By the way, remember that black mini-skirt Sheila used to wear? Well, I tried it on and it fit perfectly. I almost wore it today but chickened out."

"Well, I think you got the slut-look down just fine with the leather hot pants."

"Yeah, I know. I just was trying to be funny."

"Shawn, you are unique, as in different, but also special. You have always been this way...everyone who loves you knew that you were not like most boys. Let me assure you, there is nothing wrong with being different, nothing wrong with being gay, and nothing wrong with wearing feminine clothing items if that's what you want. For that matter, if you don't like being a boy, there is nothing wrong with transitioning to being a girl, if that is what you want. But I promise you, someday there will be lots of guys that would be lucky to fall in love with you, just the way you are...whatever that is. So be what you want to be, not what you think others want."

"I know, I know. But it is hard, and sometimes lonely. Plus, I don't have Sheila nearby to talk this out with like I used to."

"Well, you have me...and your dad. Give us a chance. Have we really ever done anything that made you think we would not support you?"

After a few minutes of silent contemplation, Shawn started giggling.

"Look mom, I don't want to become a girl. I just don't want to feel so isolated for not liking things most boys like and really liking things most girls like...including other boys. I guess, I just need to have a little faith and be patient. After tonight, I am going to quit going out all the time. I am sick of it, and most of these guys are not really my friends."

"Well that would make your father and I rest easier! But if you still insist on doing the drag show contest tonight, at least let me fix your hair into something prettier!"

They both started laughing, and as if on cue, Shawn quickly moved to Jenny's salon chair. With spray mist, hot curlers, curling iron, and many bobby pins, Jenny converted Shawn's teased-out pony-tail into an elaborate up-do with gently-curling trellises hanging down the sides of his face. She also found a strapless sports bra which, with tissue padding, made Shawn look quite authentic.

Shawn had a great time at the contest in what would prove to be his second-to-last foray into cross-dressing. Shawn was disappointed to only place third in the contest, behind a 6'5" RuPaul imitator, and a chubby middle-aged queen doing Judy Garland spot-on. However, on Halloween that fall, Shawn did wear Sheila's mini-skirt to a costume party with a full makeover by Jenny and Josh beforehand. His date was a lesbian girlfriend, who they also helped makeover into a well-dressed man. This time they won the prize for best costumes!

From that point, Shawn enhanced his naturally androgynous appearance with more tasteful, yet stylish clothes, but definitely shopped short of dressing like a girl. Shawn would jokingly refer to himself as a "queer boi" or a "twink" and did not mind when others called him either. While continuing to work hard and frugally save for college, Shawn developed a keen interest in designer men's fashion wear. If he could find things on sale or had saved up enough money, Shawn began to invest in select items from D&G, Versace, Dior Homme, and Versace among others.

Shawn modeled his look after some of the skinny, long-haired male models that he would see in trendy magazines or on fashion industry trade publications showing runway shows of European designers. His hair was now grown back down to his shoulders and Jenny would style it more frequently, often to emulate the look of one of the models Shawn had saved a picture of. Shawn also got an additional earring hole pierced into each ear, and added a silver belly ring which highlighted his ultra-thin midsection. In warm weather he loved to wear terrycloth, vinyl and spandex shorts with a ribbed shirt that showed off his bejeweled midriff.

Shawn's senior year was atypical in that he had already completed his high school requirements and he was taking freshman courses at the local community college. He was spending great amounts of time improving his fashion art portfolio, and he hoped he could get accepted to a leading fashion design school. Shawn visited Jenny back east before she left for a two year stint in the Peace Corps and they spent a weekend in New York. Shawn fell in love with New York and could have spent the entire weekend on Fifth Avenue shopping. More motivated than ever, he continued working at both the art supply store and the salon and liked both far more that he would admit to his parents.

After the somewhat wild early initiation with the boys from Jenny's school and his wild period the previous summer, Shawn was now quite chaste, and usually turned down anything wilder that movies or concerts with his friends. With his growing ambition in design, along with his growing self-acceptance, he had become much more patient about the eventual fate of his love life.

Yet that fall, Shawn did have his first boyfriend, a nephew of one of the salon's best clients. James was also a senior and attended the local performing arts school where he focused on drama and musical theatre. He was leading man handsome, and both boys were quite taken with each other when James aunt arranged for them to meet. They also had instant rapport that "felt" like love to both. They "dated" exclusively the rest of the school year, and were a very conspicuous couple at James' school functions and social events.

They both began to realize that while they cared about each other, they were not really in love, but instead, best buddies...as in friends with benefits. This realization was confirmed when they had a hotel room together on a family trip with James' supportive family and had decided to let this be the occasion to "go all the way" and have anal sex, both for the first time. While James was a "hunk" leading man out of the bedroom, he was a definite "bottom" in bed and quite submissive to boot. While Shawn enjoyed "calling the shots" when they had sex, but he considered himself as a bottom, so despite all the initial promise of their relationship, James and Shawn were really not compatible sexually.

This is not to say that they did not enjoy "practicing" the mechanics of anal sex on each other and experimenting with all the things they had read about and been told about. Shawn's expectations were exceeded on how wonderful anal intercourse could be. Like with oral sex, Shawn loved the power that went with being the reason that another boy was so sexually excited, while also "submitting" by spreading his legs to receive. Shawn even relished the initial pain that went with penetration, followed by intense orgasms from having James' nice penis slamming against his prostrate.

After the school year ended, James and Shawn remained close friends, but with only occasional "benefits". To have a true friend to share things with made Shawn's year fly by. At the end of the summer, Shawn helped James pack for his trip to go to college at NYU to study drama, sad for his departure, but grateful for their great friendship and great last year. James, of course, loved living openly-gay in New York and was constantly emailing Shawn about his latest, increasingly hedonistic adventures.

The next fall, Shawn felt a bit lonely and a "deserted" by both Sheila and James, but he kept his long-term goals in focus and began his second year of community college and continued to work at both the salon and the art supply store. Although not the prodigy that his sister was, Shawn worked hard on academics and had tested well on the ACT. He hoped to transfer to NYU the following year and formally study fashion design. Now fully-grown at 5'7" and 125 pounds, Shawn was stylishly androgynous, even without dressing up or wearing makeup or jewelry. Even in a city like San Francisco, full of eccentric people, Shawn turned heads with his striking appearance, immaculate hair-styles as well as fashionable attire and accessories.

Enter Jason

On the Friday that began spring break, a soon-to-graduate architecture major from Cal Berkley named Jason walked into an art store in San Francisco to buy drawing supplies. Instead of fun and games for spring break, Jason would be spending it at his parents' nearby Victorian home, working on his final project necessary to graduate. If his parents had not been in Europe, he would have just stayed in Berkley, since being around his parents generally stressed him out. As Jason was paying the friendly silver-haired store proprietor, he was drawn to the two portraits on the wall behind the counter. One portrait was of a beautiful, smiling girl with dark brown hair, who appeared to be running outside based upon the "movement" of her hair in the picture.

The other portrait was a close-up and it was hard for Jason to look away. In it there was the most angelic face he had ever seen, with piercing blue eyes and skin that looked naturally tan and ultra-smooth. There was a light behind the subject which created an aura around the face. The subject had shimmering, light-brown hair that flowed in waves and gentle curls out to the borders of the canvas. The pose was from the neck up and only a thin shiny necklace was visible below the face. There were prominent diamond stud earrings in the upper hole of each ear, and a thin diamond drop strand earring in each lower hole. Instead of a smile, this figure had its lips pursed as if contemplating his future while looking upward.

Transfixed as he was, Jason regained his composure and took his supplies, and asked the friendly storekeeper,

"Who is the artist that painted those portraits?"

"Well that would be me. I hope you like them. My name's Lance!"

"I'm Jason."

"It's nice to meet you Jason! So you're you an architect?"

"Well, almost. I'm finishing up my last semester right now at Berkeley. At least it will be my last if I can finish my final project this week!"

"Well good luck to you! Also glad you like the portraits."

"They're really great. Who are the subjects?"

"They're my children Sheila and Shawn. I do portraits of them every year or two."

"Really? Are these recent?"

"Pretty recent...finished Sheila's about two months so she could see it before she had to go back overseas for the Peace Corps. Now, I just finished Shawn's because he is going to community college here and can see it anytime. In fact, he works here part-time and will be here tomorrow helping me out."

Jason was all of sudden speechless and barely mumbled out a goodbye as he looked at the portrait again and left. He thought to himself...the picture of "Shawn" is a picture of the store owner's son?! The picture was such a close-up so it could have been a girl or a boy. Jason's original thinking that it was a girl was based more on the overall beautiful face that radiated from Lance's portrait, versus any specific detail of Shawn's long hair or earrings. Jason's insides turned with confusion, excitement and more confusion.

This was only the most recent moment that poor Jason had been confused.

By way of background, Jason had always been a perfectionist of sorts, being driven by not wanting his high-achieving parents to be disappointed in their only child. Three sports, student government, Homecoming King, and Salutatorian, are just a few of Jason's many high school accomplishments that led to his attending the vaunted architecture school at Cal Berkeley. At Cal it was no different, as he felt compelled to join his father's fraternity even though he really did not like the hazing and macho humor. He felt like he had to have a trophy Theta or Pi Phi on his wing, auditioning to be the Mrs. Jason someday, or he was not living up to expectations.

Jason was never at peace or truly happy, however, and at one point he was so depressed and stressed out that he sought out the University's mental health counselors. Fortunately, he truly loved the creativity of architecture and could not wait to work in the field. His final year he relaxed a little more as saw the light at the end of the tunnel with only one year left of school and having already accepted a premier position after graduation with a New York architecture firm. He became less active in the frat and did not worry about having a girlfriend. Surprisingly to Jason, his parents did not pass judgment on any his recent activities, or try to influence him on his career choice. They only praised him for all his accomplishments, including earning Phi Beta Kappa.

However, beyond his academic accomplishments, Jason had been experiencing great anxiety about not wanting a girlfriend, not to mention that he had totally been faking his sexual interest in his last two girls he had been with. His uncertainty reached a new level over Christmas break when a group of senior architecture students had done a field trip to London to study historic architecture, Jason's passion.

By random assignment he roomed with an Emo-looking exchange student from Amsterdam, who was probably just as disappointed by his roommate assignment as was Jason. However, in spite of their differences, they found common ground in their views on architecture, and both found their pre-conceptions to be over-blown. Jason, despite his "preppy-frat" look, was actually very inclusive and friendly to everyone and impressed the Emo Boy with his knowledge of alternative music.

All the students sought out the London night-life after their official day ended. The first week, everyone went out to the Fodor recommended restaurants and pubs en masse regardless of their social preferences. By the trip's end people went out according to interest and for Jason and his new friend, this centered on finding live music venues. One of these first nights out, his roommate had picked up a multiple-pierced "hippie chick" and the music club and brought her their room, requiring Jason to crash next door. Another night, he brought back a trashy fashion model, both too drunk to say no.

One night they went to a rather seedy club in an old building that had a band playing songs by English alternative bands that sprung up in the 1980's like the Cure, the Pet Shop Boys, New Order and Joy Division. Jason loved the music but the crowd was over the top in its wild dancing and eccentric clothing. Naturally, his roommate fit right into the crowd and before long he was on the dance floor although with no one in particular.

Feeling out-of-place and dressed conspicuously conservatively, Jason got bored and went to find his roommate to leave. He found his friend in the corner sitting and making out intensely with another boy that looked a bit like an overgrown Billy Idol. Jason was a bit shocked, given that he had seen him bed-down two girls in the last week. But now watching his friend getting down with another guy, it sent blood flowing to his groin and he felt himself getting hard.

Without interrupting them, Jason moved to another part of the club where he could watch their antics out of the corner of his eye. Eventually, Emo Boy came over looking quite drunk and quite happy. He briefly introduced Billy Idol to him and told Jason that they were going to "go out" and that he should take a cab home by himself. Jason later went to sleep eventually but his erection would not subside until he masturbated.

Sunday morning was a sleep-in day and his roommate did not make it back until noon. He immediately went in and showered, which awakened Jason from his drowsy state. When Emo Boy emerged from the bathroom, Jason was sitting on top his bed reading while only wearing his boxer underwear. His roommate broke the ice by apologizing:

"I'm sorry for deserting you, but I was drunk and horny."

"No need to apologize. Uh...I was surprised to see you with a guy, after the other nights."

"Oh right. Look I don't know about you, but I can get it on with anyone. I love chicks, but why limit myself? Actually, it's pretty common thinking where I come from."

"Oh. Okay"

"None of my business mate, but are you telling me that you have never been with a guy? Even just fooling around? At least admit you have thought about it before."

Jason did not answer right away. Then hesitatingly, but honestly, said:

"I have never done anything like that, and I have mostly repressed all the evil thoughts my parents, teachers and coaches did not want me to think."

"Too bad! Not thinking for yourself doesn't seem to be making you happy right now."

"No I guess not. It's not always easy to live up to everyone's expectations."

"Sorry man. I did not mean to upset you. I hate to admit this because I initially assumed I would not like you, but you are one cool dude! I would not have wanted to room with anyone else on this trip:

"Well the feeling's mutual. But speaking of evil thoughts, I...I should confess that last I had some when I saw you mugging with that guy in the bar. If you want to know the truth, it made me jealous to see you having so much fun, even though I am not sure why."

"Well, not to worry, I won't sexually assault you while we room together...even though I am sure it would it would be great fun!"

Jason felt his groin grow heated as a tent arose in his boxers. His friend did not initially say anything but chuckled a little bit as he looked down at Jason's growing erection. With great tenderness, Emo Boy sat down and began massaging Jason's thighs. Jason instinctively recoiled but relented immediately with the quiet but firm command to "relax". Leaving his towel around him, his friend began gently stroking Jason's rapidly hardening cock through his boxers and then gently freed it through the slit. After a few more strokes, he urged Jason to lift up his backside so his boxers could be removed.

His roommate lowered his head to Jason's crotch and placed single wet kiss on the tip of Jason's tool. He then slowly and gently alternately licked and kissed up and down the shaft and gently nuzzled Jason's balls while he cupped them in his hand. Eyes closed, Jason was grimacing in ecstasy and let out a moan when his friend took him completely in his mouth. Jason had never had such an expert blow-job and could not imaging how his friend had gotten so good at it, other than he seemed to be enjoying himself a lot more than the reluctant girls he had been with. Nearing climax Jason moaned more and warned his friend that he was coming. Instead of stopping, his friend sucked harder and deeper and began jiggling his balls with his fingers.

As Jason exploded, Emo Boy took the first surge and then effortlessly swallowed. He then pulled off a couple of inches while still directing the spurts towards his mouth as he watched Jason's orgasm with great excitement. Afterwards, he got up and returned to the bathroom to clean himself. Jason lay stunned at the best orgasm in his life being caused by another boy!. When he came out of the bathroom, Emo Boy walked over to Jason and kissed him on the forehead.

"See that wasn't so bad! Was it? But now I need to crash. I am exhausted from all this cock-sucking!"

Nothing else was said the next day or the day after. On their last night before returning stateside, Jason and his roommate got quite intoxicated with a large group of fellow students. As they helped each other into the room, they both stumbled with Emo Boy falling on top of his Jason on his bed. Instead of immediately getting up, he leaned down and kissed Jason full on the lips. Jason's initial response was to enjoy being kissed, as he was quite horny, but his homophobia kicked in, and gently pushed his friend away and helped him into his own bed. About an hour later, Jason was awakened by his oversized erection, and some alcohol-induced dreams that he was still kissing his friend.

After about 45 minutes of trying to get back to sleep, Jason's anxiety grew, and armed with alcohol-courage, he crept over to his friends bed and got under the covers. Emo Boy awakened peacefully, and put his arm around Jason and then they kissed again, and again hugging and feeling their erections against each other. Jason lifted himself up and began pulling down his friend's gym shorts that he was sleeping in.

"Let me try."

"Okay, but you don't have to..."

"I...want...I need to know."

"Okay then...I'm all yours."

Jason awkwardly began working his way down his friend's chest with kisses, while he felt his own package being massaged. When he reached the crotch he hesitated, but he was urged on by a firm hand behind his head. He tentatively licked the tip, and then clumsily took the top of the head into his mouth. His mind raced with excitement from doing something so forbidden in his rigid upbringing.

Emo Boy then interrupted the action and positioned himself to service Jason, and the boys went on for quite awhile in a 69 position exploring all aspects of each other's groin. Jason moaned loudly and was the first to come and Emo Boy did not spill a drop as he finished him off. When his friend warned Jason that he was coming, Jason initially pulled off, but after the first burst hit his face, he put his head back down. Hesitating at his first taste of semen, Jason became more comfortable and swallowed the remainder.

Jason awoke with a major hangover in his own bed barely able to remember many of details, including how he got back into his own bed. Getting up to get aspirin, a tangible reminder of the events was in the mirror as he noticed the dried chalky spots on his chin and cheek. But as Jason got back in bed, he reluctantly remembered that it had been all his idea. Jason also remembered that he loved every moment of it. Looking over at his friend peacefully sleeping, Jason did not really feel any particular attraction to him, even though Emo Boy was good-looking in an eccentric way.

However, the purposeful act of horny oral sex with another guy ignited a previously unrevealed fire in Jason. His public façade began to restore itself as his hangover subsided as he rationalized that the whole event had been just alcohol-induced drunken insanity. However, like a person who tries crack for the first time, saying it was "just a one time experiment", Jason subconsciously knew that he could not wait to do it again.

As they prepared to depart home nothing was said, and outwardly it was like had never happened. When they returned to campus, Jason and Emo Boy retained their friendship but were never intimate again, and never talked about what they had done. True-to-form, Emo Boy ended up hot and heavy in love with a sexy French exchange student, who he was living with by the end of the semester.

Jason struggled mightily with anxiety about what he had done...more importantly, how much he had liked it. What would his parents and friends say if they knew? He tried to purge these thoughts from his mind. It was hard to purge these thoughts from his mind as he would drive up and down the streets containing Berkeley's gay bars, too afraid to stop and go in, but unable to stop checking them out.

On one hand, he did find beautiful girls attractive and he had certainly performed in bed with more than a few. But he did not enjoy their often ditzy companionship, and had recently gone completely cold on sexual attraction to girls he met. From a pure companionship and conversation perspective, Jason preferred the company of other guys. Jason usually had no sexual attraction to most guys, and particularly not macho types. But his insides would burn with curiosity when a "flaming" gay boy walked by, confident in their flamboyant appearance and their non-conformity. Jason stayed busy with academic work, so it was easier to put this inner conflict on the back-burner. He looked forward to moving to New York where in addition to starting a career, he could have a fresh start, free to explore all of his thoughts and feelings.

Even though he was going to have to complete his senior project, he was glad when spring break arrived. His parents had invited to join them on a trip to Mexico, but instead he opted to stay by himself at his house in San Francisco to work on the project. Upon arriving home mid-Friday afternoon, Jason realized that he had forgotten to pack a few items that he would need for his project. So he walked several blocks to an art supply store he knew of to restock.

As he walked to the store, Jason thought to himself,

"Yes, this is just what I need; a peaceful, uneventful spring break to clear my mind..."