NOTE:
The original artwork for this story has been removed to facilitate easier publication on this site. If you would like to see the illustrations, please contact me. Enjoy!
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The anticipation and worry was killing him. It had been two days -- TWO DAYS -- since Jonathan sent Lilly those photos. Had she seen them? Did she hate them? Would she never talk to him again? This was silly of course. She had to love them, right? Heck, she'd practically begged him to send them to her. She was probably just busy. It was finals week, after all.
Jonathan sat there in his dorm room desk chair, staring at his laptop. Now a sophomore in college, part of him lamented that this was how he chose to spend his free time. Why was he fixated on an imaginary lover on the other side of the continent when plenty of beautiful, smart, and single girls passed through his building every day?
Shy and awkward as a kid growing up in an industrial Oregon town, he had trouble forming relationships with others his own age. For the most part, his friends were video games, cartoons, and books. While not necessarily shy, he tended only to be outgoing with adults. He was his parent's pride and joy though. A straight-A student and a national merit scholar, they often made it a point to show him off to other adults, which was fine by him. He could engage adults on a variety of topics and speak with an intellectual maturity well beyond his young age. They always seemed to appreciate how smart he was and treated him more like a peer than he ever felt kids his own age could.
However now that he was becoming an adult himself, his preference for social interactions with people older than his peers was becoming more problematic. If he wanted to be successful on his own, make friends, and fall in love then he needed to overcome his own long suppressed social anxieties. The kids he eschewed in favor of adults were becoming his mature peers and he didn't know how to relate to them.
His body had come around though. No longer long, scrawny, and crater-faced; Jonathan was starting to fill in. His skin had cleared up, and he had gained weight. Instead of toothpicks for arms and legs, he now had some muscle tone on his 6'1" frame. He'd traded in his sulky emo-do in favor of a clean, natural brown medium crew cut. Now that he didn't have to stare at moonscape of blemishes every time he looked in the mirror, Jonathan was slowly coming to see himself for the good looking young man he'd become. He'd even caught himself admiring his reflection when walking out of the men's showers. His pecs were defined, and he could make out the shape of his sinewy biceps without the need to flex. His abs weren't quite six-pack, but the wispy line of hair trailing from his belly hinted at the nicely matured manhood that lurked beneath his towel.
The girls on campus had started noticing him as well. There was one in class he'd caught staring at him. Several others had smiled invitingly at him as they passed him walking through campus.
Jonathan wasn't dumb. As inexperienced as he was, he could tell when a girl fancied him. It was just that his confidence failed him. Inside he was still the awkward social outcast who had learned to avoid bullying by eschewing all forms of social interaction. He knew he needed to be brave and put himself out there, but the depths of his own insecurities were overpowering. Instead of engaging, he just lowered his head and started walking faster in full retreat of the inviting feminine smiles targeting him.
This couldn't go on forever. He needed to learn how to talk to a woman and, more importantly, gain confidence and trust in his own prowess as an attractive man. The hardest part was introducing himself and starting a conversation. Being the geek that he was, Jonathan decided to let the internet do the introductions for him.
He wasn't looking for a relationship. He was looking for practice to build his confidence in order to pursue someone in the real world. So instead of setting up a profile on a dating site, he started hanging around in romantic chat rooms. That's where he met LillyPad4_69.
It was another lonely night alone in his dorm room watching the romance chat scroll by. By then Jonathan had figured out a majority of the other "people" on there were either spambots or trolls looking to rile everyone else up. He monitored the feed, but rarely posted anything. Instead he would look at other people's profiles and if he thought a cute profile might actually link to a real person, he would summon up the courage and IM them a "hello."
Lilly had one photo on her profile. It was a cropped picture of a beautiful voluptuous young woman smiling and holding up a peace sign with her fingers. All he could see of her face was her lips and chin. He gathered she had short red hair based on her pale freckled complexion and the fact that there were no long tresses in view. She wore a tight green top, tattered blue jeans and had a small purse draped over her shoulder, the thin strap running snugly down between what appeared to be two fantastic, large, and pert breasts. Her tummy had just the slightest pouch where he could make out the outline of her belly button under her shirt. Her hips flared nicely suggesting an excellent curvy tush was hiding just out of sight.
When he first saw Lilly's solitary profile photo, Jonathan almost dismissed her as another bot. However, there was an authentic gleam in her eye that suggested at least the photo was a candid of a real person. If she was a real person, what were the chances she'd respond to a guy like him. He wasn't sure, but he hazarded a try anyway. Much to his surprise, LillyPad4_69 replied immediately and they soon found themselves regularly chatting and often into the early morning hours. Lilly was smart, enthusiastic, and quite witty. She got most of his obscure pop culture references and even laughed at his geeky jokes, occasionally chiming in with one of her own. Jonathan really dug her personality, but was unable to learn very much about who she was outside of chat.
Beyond her profile photo and personality, there were very few specific details to be gleaned about Lilly. She lived on the east coast, far away from his Oregon dormitory and went to a local community college where she lived. She worked part time for a legal firm and she was still living with her parents while she worked on her degree in communications.
No last name. No phone number. No other pictures. When he asked, she politely changed the subject. Despite her fantastic and sexy personality, Lilly was an enigma. What was she hiding? Was she not at all the person she claimed to be? Jonathan worried about this more than he probably should have. After all, she was exactly what he was looking for: a young beautiful woman to coax him out of his shell, converse with, and build his self-confidence. Couldn't he afford her some anonymity? He had turned to the internet for her help and she was providing that in spades. Lilly loved his profile and cooed over the vacation pictures he sent her from last summer. She told him he was sexy, smart, and any woman would be lucky to have him.
Lilly's effervescent and creative personality soon pushed their conversations towards sex. At first it was all innuendo, with each taking advantage of any opportunity to make a sexual pun or crack a, "That's what she said." Unabashed, Lilly would flirt and escalate from there. Soon they were sharing fantasies and then assuming their respective roles in them. One night, Lilly was the dominatrix issuing commands to her pet. The next night, she was a much younger submissive bending to the whims of her 'daddy'. They explored everything from mundane dormroom sex to the kinkier aspects of Jonathan's favorite japanese animes.
It became an alluring routine that their chats would end with Jonathan slowly stroking himself off, delaying release while she described what she was doing to her pussy as she thought about his 'hard cock' ramming in and out of it. It was strictly text-only, but Lilly's enthusiasm and creative dirty talk always coaxed Jonathan to climax every time. She still teases him about the time he got too into the moment and carelessly came all over his keyboard. "Sticky keys" was a running joke now.
In the afterglow, before they wished each other goodnight and sexy dreams, Jonathan always politely pushed the envelope on getting Lilly to open up to him more about who she was, particularly about sending him some photos, any photos of her.
One night, she finally relented. She admitted that she absolutely loved the time they spent together and "Jonny" had more than earned his reward. She greatly appreciated his patience with her and said she would send him the sexiest pictures of her he could possibly imagine, on one condition... He had to send her sexy pics of him first. Not just any pictures at that. She wanted to see a striptease that slowly built from getting undressed, to masturbation, to a glorious cumshot.
Naturally, Jonathan offered immediately to turn on the webcam and give her a show right then, but she declined. No, she wanted a keepsake to remember him by. Something he put thought and effort into creating just for her. Jonathan knew he would do just about anything for Lilly, so he didn't put up much of a fight agreeing to her request. Lilly told him she was going into finals this upcoming week and really needed to focus on studying. She might not be online as much, but rest assured she was thinking of him and not-so-subtly hinted that this time would be good for him to do his "homework" for her. Then Lilly said she couldn't wait to see what he "came" up with and blew him emoticon kisses before signing off.
That last chat had been four agonizing days ago. The night of the request, he was already a mess from masturbating so he decided to wait until the next day to do his "homework." He'd never groomed himself down there before but he instinctively knew that "wild bushman" would not rise to the level of effort she was requesting. Besides, his penis would certainly look larger on camera if the hair around it was properly manscaped.
Although embarrassing, Jonathan spent the next afternoon locked in his dorm room with a razor, shaving cream, a bucket of water, a trash can, a towel, and an electric trimmer. When he was done, he had successfully trimmed and shaved all of the hair from his balls and between his legs, leaving a short, neatly-trimmed patch of pubis just above the base of his member.
Even he had to admit, seeing his freshly shorn cock was a bit of a turn on. Just wiping away the remaining shaving cream with a towel, thinking about what he was about to do, was more than enough to bring his staff to full attention, a bead of pre-cum glistening at the tip. He was so turned on, the urge to masturbate right then was quite strong, but he admonished himself and set about picking out his attire.
He figured a poor college girl wouldn't likely expect too much in the fashion department from her equally poor college lover, so he settled on a simple t-shirt, a tight pair of jeans, and a snug new pair of white Calvin boxer briefs.
