Learning to Draw

Edited by: Pope1944. Thanks!

Note: there will be anal sex in this story so if you don't like that, please read some of my other stories.

*****

Never in her young life could Jessica have imagined being so at ease wearing nothing but lingerie in her brother's room while he was staring at her. More than just staring, he was actually studying her body in order to draw it better. In fact, she knew that he was even going to transform her image slightly: her twin brother David was in fact going to draw a nude image of her. Not that it would require of him a lot of imagination: the lingerie she had chosen today was very flimsy and mostly transparent. Yet, she felt really at ease. It had only taken three such sessions to get her to fully relax.

The first one had been horribly stressful, though. Looking at David now, she could see that he was still flushed. She guessed that her brother was fully aware of how remarkable this situation was despite the look of concentration on his face. Jessica smiled, relaxed on his bed as he stared at her exposed body. Yet when they both heard their mother coming home unexpectedly and shouting "David! What's the meaning of this?" everything changed very quickly.

But before we get to that, let's roll back to five days ago when all this started. When Jessica came home very late, somewhat later than her usual curfew, she planned to come in by the backdoor without making a sound. But as she rounded the corner of her house she jumped and almost cried in fright when she saw someone on the porch, a few feet away from her. She realized that it was her brother and that despite her jump, he wasn't about to laugh at her. Instead, he was crying. Jessica understood what must have happened. "Didn't win?" she asked softly, sitting next to him.

"Nope. Not even close..." was his teary reply.

"Really? Damn!"

"Yeah, damn. Fuck drawing. I'm done."

Jessica was surprised: drawing was David's passion. It even threatened his grades in school. He had managed to graduate anyway, but he was placing all his eggs into this drawing basket. At least until now. "What do you mean done? Done with this contest?"

"No, done with drawing. I'm good enough, but not as good as I need to be to make a living out of it."

"Bullshit! You're more than good enough!" Jessica replied, and she meant it as well. "What was this year's subject?"

David didn't reply. After a while, he said "A game of volleyball."

"Oh. Shit."

"Yeah, shit indeed..."

David truly was a great artist despite his young age. He could draw anything from scratch with no model or photograph and it would turn out great. Anything but the human body. His males were decent, but his females were... well, let's just say that he grew up reading manga and for the last couples of years, with many of those manga being hentai. A while ago, Jessica had found a stash of his secret drawings, drawings of miraculously endowed females in various poses. Many of them included other females or miraculously endowed males in various positions. Sexual positions.

They were stunning (even though looking at them behind his back made Jessica feel strange). The fact that they were stunning was not the problem. Well, problems, to be precise. The first problem was David's. He had done so many of them that drawing a real woman with real proportions was a challenge for him. A profound challenge. His realistic men were not so bad, but women... Ouch. And he knew it. And it frustrated him to no end. Now the contest had forced him to confront this limitation.

The second problem was Jessica's. Despite her feelings about violating his trust by looking at his hidden drawings, she nevertheless went to his stash regularly. At first she had been drawn in, so to speak, by their beauty and quality. What she hadn't expected was that at one point she became convinced that some of the females on his pages were, in fact, her.

Of course, she didn't have a distorted body, nor were her breasts so monstrously big. Yet her face, eye color and her hair were spot on. In some of those drawings there was a male with her in various sexual poses, but his face was always left either blank or not fully drawn. Was he drawing himself with her?

The first time she recognized herself, Jessica's first reflex had been to leave his room. But then again, she was really taken in by the magic of his talent. Gradually, she had accepted this as a strange form of compliment. From then on, she had started to see her brother differently. Despite the urban legend, they didn't share a special twin bond. They were fond of each other like some brothers and sisters were, but nothing more. After having found those drawings though, the way she had seen their relationship changed.

They were both virgins and she knew that it was normal for boys to have feelings for just about everything they saw. And since he had never said or done something about these feelings for her in real life, she didn't feel threatened. So as the months went by, she had sometimes imagined him drawing her, his hard cock in his free hand. Once, while deep in the throes of a long masturbation session, Jessica had thought about accidentally appearing nude in front of him. More precisely: arranging to have such an accident. She had climaxed soon after, but when her head had cleared, she had laughed and realized that it wasn't a good idea.

Still she kept going to his drawings to this day. More and more often, she found herself using his drawings as the basis for her masturbation fantasies. She would often use her dildos in place of that headless man, her brother, and she would assume the position he had drawn.

She was fascinated by the ones depicting anal sex. Anal sex had been a part of her fantasies for a long time now, and the few times she had explored it with her dildo had left her trembling. Learning that her brother was fantasizing about the same thing, and with her... After seeing those drawings for the first time, she had pushed her dildo in her ass and the ensuing climax had left her trembling for long minutes in her bed.

But one of her absolute favorites was one where she was sucking a man's cock. And by sucking she meant deepthroating. Jessica had always been fascinated by deepthroating, and the few good videos of that strange act that she had found on the net always led to thundering orgasms. It seemed like her brother was into deepthroating as well: on one page, there were four drawings of the same girl, hentai-Jessica, taking a huge cock progressively in her mouth. The first drawing showed a cock that was at least ten inches long and by the last drawing the hentai version of her had her nose pressed against the headless man's pubes. She had often masturbated thinking about that drawing.

Now, two days after that fateful nighttime meeting on the back porch, Jessica had an idea. It certainly was a crazy idea, but she didn't think it was too crazy. That same night, given that both their parents were gone, she knocked on her brother's bedroom door. She was extremely nervous. When David opened his door, he was frowning in puzzlement: she rarely came to his room. "What do you want?" he asked, still looking like crap from the contest.

"I have an idea that might help you." she said.

"With drawing?"

"Yes."

"I told you I'm done sis. Over, finished, finito..." he replied, closing the door.

But she held it open. "Just hear me out." David groaned, but let her in. He sat at his desk, and her on his bed. "Listen, I know you tried everything to draw normal humans. We talked about it with mom and dad last night. But there's one thing you haven't done."

"What?" he was absentmindedly browsing the net, half listening to her.

"Real models."

"Well I know that. But there are no art lessons in town and the big city is too far. Besides, these sessions usually involve nude models, and I don't see mom letting me stare at a nude woman all evening long."

"What if you could get a model right here?" Jessica asked, biting her lips. She suddenly realized that she was extremely nervous. She didn't even know what scared her the most: the he would accept, or that he would refuse her.

"What do you mean? We don't have models here... And which girl would want to pose for me for hours in a bikini? All your friends hate me." he said, clearly in a self-pitying mood.

"That's not true! Mandy doesn't hate you!" Jessica replied.

He looked at her with a small smile. "Well, no, she doesn't." Mandy was madly in love with her brother, but he didn't feel anything for her. Mandy knew it, and even had had other boyfriends, but she always made sure to let him know that she was interested. It was actually quite funny. And sweet. "But I wouldn't want to ask that of her knowing how she feels..."

"What about me?" she asked suddenly. There it was, she had said it!

"Ugh? You want to ask her to do it?"

Jessica sighed, shaking her head slightly. "No, I mean what if I were to model for you?"

David frowned and immediately looked angry. "Please Jess... These past two days were terrible, and I'm really not in the mood for games."

"No games. Look David, I know you have enough talent to go very far. Looking at you moping around for the past two days, I tried to figure out what I could do to help. And when you talked about real models last night, it clicked."

David was staring at her, still trying to determine if she was sincere or not. "You mean... You mean that you would really, I mean that, er..."

"Yes David. I'd be willing to pose for you in my underwear." Fuck, why had she said underwear?

"Really? You actually mean that?" David was brightening, and also blushing.

"Why is it so hard to believe that I might want to help you out?" she asked, slightly irritated by his reaction.

"No, it's not that sis... Oh I'm sorry. I thought about this possibility, but I never even considered actually asking it of you... This is... this is great."

"You already thought about it?" Jessica asked, although she had already known. She had seen one drawing of her on his bed while he was drawing her.

"Well, yes... But why would you do that?" David asked, still puzzled by her offer.

"Think of me as an altruistic sister!" she replied, a winning smile on her face. "So if you thought about asking me, it must mean that you think I'm pretty?" Jessica asked in her highest, most girlish voice.

And David laughed, exactly what she had wanted. "But of course! Jess! You're really pretty, and it would be an honor to have you as my model!"

Jessica was suddenly taken aback by the compliment. "Why thank—"

But he interrupted her. He got up and pulled her up into a hug. "You have no idea how happy I am about this!"

"Well, glad to hear it." she said. "I'm flattered that you think it's an honor, but it also has to be a secret."

"Of course!" he smiled, still holding her shoulders and staring at her.

"And no hentai stuff!" she added, laughing.

"What? I don't do that!" he replied nervously.

"Bullshit! I'm sure you have a stash of that somewhere..."

David paused, his expression more serious. "Ok, deal. No hentai stuff when you're posing for me. When do you want to start?"

"How about now? We have the house to ourselves."

Jessica laughed at his reaction. David had barely begun to process that he was going to be able to stare at her in lingerie, one of his favorite fantasies, but when he leaned that it would happen right now, he froze. His mouth fell open and his eyes darted down to her cleavage very briefly. Jessica would have given a lot to be able to know what he had felt during those few seconds of silence. He then mumbled something about having to get ready, and he asked her to come back in fifteen minutes.

Fifteen minutes later, even though she had felt relaxed at the end of their conversation, Jessica was tremendously nervous again. She knocked on his door again. The David who answered her now was so different than the one half an hour ago that she startled. He looked better, had cleaned himself and the room up, he was standing straighter, the room was well lit, and it even smelled better! "OK, where do you want me?" Jessica asked, realizing the innuendo too late.

David startled at her question, his eyes opening wider for a moment. He then smiled and pointed to a chair he had brought from the kitchen. "Right here. You may not know this, but modelling is hard work."

"What? Standing around doing nothing?" she asked, dubious.

"Yes, doing nothing in the same position for a couple of hours. Much harder than you think. That's why I brought the chair. I think you'd be better on the chair, at least for this first session."

As Jessica sat down, still wearing her bathrobe, he looked at her and said "I'm sorry if I was sceptical earlier. I was just fucked up inside and confused about this miraculous offer. Thank you sis. You really are the best."

"Well I'm happy to do it." She took a deep breath. "You want me to take my robe off?" David looked at her, opened his mouth yet nothing came out for a few seconds. "Are you nervous David?"

"Er, yep... I'm sorry."

"Don't be. I'm nervous as hell too!" they both laughed.

"Ok, thanks for that. Shit I'm nervous!" he said, laughing still. "Yes, you can take it off."

When Jessica untied and removed her robe, standing in front of the chair, David tried not to look at her. Sitting on the comfortable chair, Jessica said "David, look at me. If you don't then we're wasting our time here!"

He smiled, then looked up. Into her eyes. "I'm sorry again... This is so utterly strange. You doing this, looking so beautiful. So sexy..." he then froze, realizing what he had said. "Oh shit I'm sorry sis... I must sound like a pervert!"

"Just relax brother... Just as I know you don't have much experience with half-dressed girls, you must know that I don't have much experience with guys telling me that I'm sexy..."

"Oh but you are... Well. Ok. Let's get to work." Jessica saw him walking around his desk and seating himself down. Looking up, he said "This is still really strange Jess. You know I'll have to look at your body..."

"Oh for the love of gods David, just stare at my tits for a while if that's what it takes to get you started!" Jessica said, laughing, while at the same time realizing how, once again, her words could have another interpretation.

But this time it worked, and David went to work. He asked her to assume a few positions before finding one he really liked. It wasn't suggestive or sexual at all, and Jessica was glad. Despite her bold words, she was still pretty nervous and still felt strange as she saw his eyes roaming all over her body. Gradually she relaxed. To her surprise she even felt, a few times, tingling sensations in her pussy as she looked at her brother staring at her.

Some of his hidden artwork of the hentai-Jessica came back to her. She hoped that she wasn't flushing! David was red faced through most of the time he was working, and eventually Jessica realized that it wasn't because he was shy. Instead, David looked positively aroused. "Well, of course..." she thought. "What shy, virgin guy wouldn't be aroused while staring at a barely dressed good looking girl?" She refrained from smiling as to not ruin the pose.

After an hour and a half of work, David looked up and said that they should probably stop there. When Jessica stood up and walked towards his desk to look, he was suddenly very nervous. As if he hadn't even considered that she would want to look. She was fascinated by the result. Of course it wasn't a finished work, but it was nevertheless remarkable. Grinning, she saw that her drawn breasts were significantly bigger than her real ones, but she didn't say anything.

Her face was amazingly well drawn though. It was as if... "David, why did you spend so much time on my face?"

"Because it's a really important aspect of drawing people." he answered meekly.

"I know that, dummy!" she replied, smiling at him. She suddenly realized that she was standing very close to him wearing only fine lingerie. "Look. I'm here to help you with the human body... You can draw my face as often as you want—"
"Oh, I know! It's just so weird to stare at your body like this... Even now, this close to you... Shit!" David suddenly stood up and moved away.

"What's wrong?" she asked, slightly annoyed.

"Nothing!" he replied, keeping his back to her.

"Oh what the fuck David! It's not easy for me to stay there in my lingerie, but I want to help you." she walked around the desk and grabbed his shoulder to turn him around. "If you don't want to do it, or if you think my body is not beautiful enough—"

Jessica stopped talking after forcing him to turn around. Even though she was looking into his eyes, she couldn't miss the obvious erection in his pants. "Oh..." she whispered.

"Jess, it's not because I don't find you pretty enough... Quite the contrary. Oh shit, I'm sorry. This is so inappropriate! This wasn't a good idea." he finished, his head lowered.

"Stop it David!" she said. "This doesn't change anything. In a couple of days we're going to do this again and I want you to finish this drawing even if it means that you're going to stare at my breasts, my stomach, my thighs or my panties all night long. Alright?"

David was clearly stunned, his eyes opened wide. "Ok."

"It's settled then. Treat me like you would treat a model you don't know."

Just before going out of his room, she added "And please don't work on it without me!" she smiled. "You already made my breasts big enough as it is!"

"What? No I didn't! I was actually extremely careful about them!" he pleaded.

"Oh come on... My breasts are not that big, not that amazing!" Jessica grabbed the drawing and went to the bathroom. After looking at herself sideways and at the drawing, she saw that he was right. "Well I'll be..."

"I know! You have amazing breasts!" David piped in from behind her.

Grinning and blushing, Jessica apologized. "It's my turn to be sorry. Guess I don't look at myself in the mirror often enough."

They both went back to their respective rooms and tried to go to sleep. Without either one knowing, they both spent more than a sleepless hour, thinking about what had just happened. The only thing that Jessica could easily guess was that he would masturbate himself to sleep. She was right, of course. He, on the other hand, would never have guessed that his sister would do the exact same thing.

She hadn't been kidding when she said that she wasn't used to guys telling her that she was sexy. Sure a few guys at school had been interested in her, had wanted a date. But the feeling hadn't been mutual, and nothing happened. She was secretly jealous of two of her friends that were getting a lot of attention from the guys. So in a very strange way this unexpected erection and his obvious desire were very flattering.

Jessica didn't quite think of her brother as she masturbated with her dildo, but she did picture that headless man in the drawings, a man that seemed to elicit very powerful emotions in the cartoon version of herself. Once again she pushed the dildo deep inside her mouth, feeling it touching the back of her mouth and pushed in a bit further, imagining that amazingly deep deepthroat drawing. As she climaxed, she kept the dildo in her mouth, deep enough to prevent her from breathing for a few seconds. She was dizzy with pleasure for a while until she fell asleep.

Three days later, they had another night alone at home, and this time it was David who asked her. She grinned and accepted, and while she took her shower, the butterflies in her stomach returned. "Oh shut up, damn you!" she thought. "I wanna enjoy this, even though it's no more than practice for when other guys will actually be interested." She grinned in the shower, realizing that they would both use this as practice. While choosing another pair of lingerie, a bit sexier this time, Jessica decided that she would try to add a bit more sexiness in her movements. Nothing overtly sexual, just a bit more... intensity.