Story By: B.C. Kingston
Artwork by: B.C. Kingston
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.
Grabbing a digital camera his parents bought for him before college, Jonathan laid back on his bed and set about complying with Lillie’s lurid “homework”. He decided to leave the lights on and the camera flash off to avoid dark images or washout. Sitting on his bed in the daytime with the fluorescent lights on, camera in hand was certainly a strange feeling. Embarrassed, he considered putting it off or maybe even giving up altogether. But then he thought of what Lillie’s reaction would be when she saw his pictures. He thought of her taking her giant boobies out of their holsters, rubbing her nipples, and snaking a hand down into her panties as she looked a sexy pictures of his, Jonathan’s cock.
That was enough. Already rock hard, he could feel his tight jeans straining against the bulge. He laid back, aimed his camera, and took a picture. Getting more into it, he undid his jean button and partially unzipped his fly. He took another picture. Next, he peeled his fly all the way back, revealing the mound of his white boxers straining up into the open air. He took another picture. The wet tip of his cock was already leaking through the tight fabric. He took his hand and dolloped a bit of precum from it, stretching the sex sinew up into the air. He took another picture. Next he peeled back the waistband, revealing just the tip of his purple, bulbous head. The digital camera clicked again. Then he reached his hand all the way into his underwear, gripping his shaft. Lifting it up slightly, he took another picture as he slowly stroked himself under his underwear, the exposed tip of his penis now drooling a thin line of dew down onto the fuzzy happy trail of his stomach.
Jonathan set the camera down for a moment and took his jeans the rest of the way off. Laying back down, he pulled his waistband the rest of the way down, nestling it snugly under his balls. He snapped another picture of himself free of the Calvins, his member rigid and veiny, sitting up at a 35 degree angle in the cool dorm room air. Jonathan had never thought of his penis as very large. He’d measured it before of course - a respectable six and a half inches, a bit larger than the average (so he’d heard). But now it looked monstrous. He’d never been so hard before in his life, and the recent manscaping certainly helped to reveal the full splendor of it. It was veiny. Brownish at the base, red in the upper half, and a shiny purple at the tip. His balls were all the way sucked in, hard as walnuts and goose pimpled in the open air.
Jonathan pulled his underwear all the way off and spread his legs a bit as he lay back again. Turning the camera on it’s side, he tried to get a picture with his cock taking up the full diagonal width of the frame. He snapped it and looked at the preview image. Satisfied, he knew Lilly would love it. He could imagine her getting to this picture in the series and rubbing herself furiously as she thought about how badly she wanted to take his glistening head into her mouth. It looked positively gigantic, a beast of rigorous pleasure.
Excited, he once again wrapped his hand around the base of his cock, snuggling his balls as close as he could so as much tip as he could managed was surging triumphantly from the top of his fist. He took another picture. Then he began slowly moving his hand up and down, enjoying how close to the edge of cuming he was already. He knew it wouldn’t make sense to take pictures of the actual deed because they would come out all blurry. Instead, he set the camera down and imagined Lilly, naked before him straddling his legs. Her magnificent tits at full attention bobbing up and down as she reached down and stroked his cock.
“Oh my god, I want you so bad. Your cock is magnificent!” he imagined her saying.
There is no time to spare. She urgently needs him. Laying his cock down on his belly, she slides forward, her moist sex leaving a wet trail from ball to tip. With a little jiggle of her hips, she slips him inside and immediately begins riding him.
“Oh Jonny. I’ve wanted you inside me for so long… I can’t believe how good this feels.”
Her expertise is readily apparent. Rocking back and forth with just her hips, she slides her love hole out to the tip and then thrusts it back down again. Her hands are wrapped around her breasts, her right hand pinching a nipple, her left hand feeding the other nipple to her mouth, tongue darting about salivating all over her areola.
Jonathan could stand it no longer. While furiously pounding away, his balls tensed as he held off the impending explosion just a bit longer… Then the pressure broke free, washing over him in waves of pleasure as his tip fired rivulets of cum across his belly, some spattering against his chin. After the first couple of high pressure bursts, the rest of his orgasm dripped slowly out of his cock, leaking down his tightly clenched fist, his rod pulsing angrily in time to the strong beat of his heart.
After a moment of exhausted bliss, Jonathan remembered his mission and reached over to pick up the camera. His fist still wrapped around his meat, he snapped a picture of the cum slowly drooling down it. Next he held the camera above his chest and snapped several pictures hoping to get a good one depicting how much of a mess he made thinking of Lilly. Taking his hand away, he snaps a couple more of his wet member, now laying against his belly slowly relaxing to it’s normal state.
Once again, the embarrassment returned. Laying there covered in his own cum, Jonathan pondered what he just did, realizing he now had purposefully collected digital evidence of his own debauchery. As electric as the moment was, he felt some trepidation about having to actually look at those photos, compile them, and then send them across the internet to someone who was still pretty much a stranger to him. But then he thought about how much Lilly would love these photos and eagerness to please her quickly overcame any lingering shyness about sharing his first digital cumshot collection.
After cleaning himself up, Jonathan spent the evening compiling his pictures. He put the best ones in sequence in a Word document, adding a narrative to each picture:
“I’m so excited to see you, my cock is already hard in my pants.”
“I wish it was you unzipping my fly. Wouldn’t you like to see what’s inside?”
“I’m already wet for you. Just look at the precum dripping from my tip.”
“I can’t help but touch myself when I think of you. Do you like having this power over me?”
“I’m imagining you straddling my hips, your wet pussy leaking onto my balls as you stroke my shaft.”
“Oh god I want to be inside you so badly. How much do you want my cock in your pussy? Can you imagine how good it would feel?”
“Mmmm… I’m cuming again for you Lillypad. Look at the mess I made dreaming of your sexy body!”
“I hope you loved these pictures. I definitely enjoyed making them for you. I can’t wait for you to show me how they made you feel…”
Satisfied, he posted the whole thing into an email and signed it, “Forever your e-lover, Jonathan” and then hovered over the send key. This was the point of no return. Had he misjudged her? Would his pictures end up all over the internet? Would she like them? Would she reply? Was he still sure he wanted to do this?
It was done. No take-backs now. He checked chat to see if she was online. She wasn’t. No instant gratification. He checked repeatedly, throughout the night. There was no sign of her. He knew she might not be online tonight. She had told him as much, but still the worry of waiting these short few hours was weighing on him.
Then the morning came and still no word from her. He got up and went to class and tried to focus on his studies. It was a futile effort. All he wanted was to be safely locked away in his dorm room at the computer with sexy Lilly happily at the other end. The night came and went without any word, then another quiet morning. He was so worthless in class that day, he didn’t even realize when a professor called on him to answer a question, eliciting giggles out of the other girls in class. He rushed back to his room after class and spent another lonely evening staring at his laptop, with LillyPad4_69 grayed out in the chat window.
The creeping doubt was becoming overwhelming. An endless screed of negative questions swirled around in his brain. Had he been duped? Did she hate them? Was she showing all her friends and laughing at him? Was she going to email them to the Dean or, “Oh God,” to his parents? It was all silly of course. He knew her better than that, didn’t he? Just be patient. Just be patient…