Free-Hand Drawing

She unzipped her fly and pulled her jeans down past her broad hips. She had to sit down briefly to wrestle out her legs. She had a deep navel and a bit of a paunch with soft rolls of pudgy flesh in her lower abdomen. Like her bra, her underwear was meant to be practical and did nothing to attract the eye. She bent over at the waist and pulled them to her ankles. Straightening out, she kicked them off into the corner. Her ass was broad, plump, and fleshy but protruded mostly backward rather than sagging downward. Her thighs were thick and somewhat jiggly on the inner surfaces. She had stubbly crotch hair. No doubt she had thought of me when she had shaved a few days earlier. I wished, however, that her grooming had been more recent. Meaty pussy lips protruded downward beyond the contours of her undersurface. They looked loose enough to comfortably accommodate a cock as thick as mine.

Cas's body was much softer and heavier than most of the women whom I find attractive. I once kicked out of bed a girl whose ass was considerably smaller and more toned, but the way Cas was built, and the way she walked and carried her shoulders flooded my mind with the images to classic baroque and renaissance nudes painted from the hands of the old masters. Much like these works of art, Cas was become more valuable with age.

She sat down on the couch, her ass flattening out slightly. She turned her trunk somewhat, placing her left arm on the sofa's arm rest and her right on top of the cushions at the back. She placed both legs on the couch, but let her left ankle hang off the front.

"You may begin," she said.

I studied her for a few minutes and asked, "can you put your hair up?"

She thought this over, "Very well, I keep my barrettes on top of the dresser in my bedroom. Why don't you go pick one out?"

The dresser was an antique, of course, and an expensive one at that. The top surface was surprisingly disorganized, the coils of necklaces carelessly intermingling with bracelets and earrings. I found a tarnished but elaborately crafted silver barrette. The pattern suggested something form the Victorian era. Staring at the dresser, I knew I shouldn't dawdle, but I just couldn't help myself. I slid open the top drawer. Cas had made no effort to hide her sex toys underneath her clothing. The contents of the drawer were as cluttered and disorganized as the items on the top surface. She had fishnet stockings, thongs of various colors, crotchless panties, vibrators and batteries, dildos big and small, butt plugs, gag balls, a riding crop, various leather straps used for bondage, dozens of condoms ranging in size from extra-large to slimmer fit, a half empty bottle of clear liquid labeled "anal lube," and an odd looking shiny black tool that looked kind of like an old dueling pistol or a hockey stick. This last item I found perplexing and didn't fully understand. However, the contents of the drawer painted a portrait of a woman who had done it all: oral, anal, BDSM, three ways with men, three ways with women, double penetration, maybe even ass to mouth. I knew I was in for a treat later.

"What's taking you so long?" Casdoe asked.

I quickly shut the drawer, grabbed the barrette, and took my place in front of the easel. Cas put her hair up. There wasn't a single gray strand, and in all my previous dealings with her I had never seen lighter colored roots. Some people just age well. I was certain I would.

I could tell Cas had done plenty of modeling before. She had no problem sitting still, although occasionally she would break position briefly to drink a sip of wine. She had no problem, however, returning to the exact former stance. Her face was expressionless, challenging me to draw one in.

I wanted the piece to appear timeless. I wanted to emphasize beauty more so than sexuality. To meet my goals, I knew I wouldn't have to make too many changes to what I saw before me. I toned her ass up slightly. I flattened out the mole on her left cheek so it would seem more of a beauty mark. I made the wine in the glass translucent, suggesting it was white and not red. Keeping the liquid dark would detract from the softer shading behind, making the glass and not the woman stand out as the main subject. I changed the bottle, reproducing from memory an expensive French label. I omitted Casdoe's meaty pussy lips. I drew in a subtle slit but mostly obscured it in longer pubic hair. In the end, Cas's pussy stubble helped me out as it demarked where the hairy bush should begin and where it should end. On her face, I drew a sly smirk that seemed to say, "I'm fifty. I'm sophisticated. I'm a bit saggy in places, but you want to fuck me anyway." I was really impressed with the finished product.

"I'm finished." I said.

Cas got up and stood behind me. She studied the drawing closely and at length, periodically muttering throaty mmm's and uh-huh's. At times I could feel her breath on the back of my neck and feel her swinging tits collide softly with my back.

"Well, what do you think?" I asked.

"It's not bad," she said dismissively.

"Not bad!" I said indignantly. "What are you talking about, 'not bad.' I made you beautiful."

"From what I hear, I already was quite beautiful."

"Yes, but I made you even more beautiful."

Casdoe merely shrugged and said, "it's okay I guess."

"Just okay?"

"Look, I've been trying to be polite, but since you keep pressing me, I must admit that I need to take back what I said the other day. You do need to improve your technique and practice the fundamentals a little more."

There was no way I needed to practice the fundamentals! Cas was just jealous of my talent and felt the need to bust my balls. "Okay, then, what did I do wrong?" I said, challenging her to express a more specific complaint. I doubted she could articulate a single one.

"Well for starters, your shading is uneven. The shadow of my foot is much darker than the shadow under my arm." I thought my shading was flawless.

"Also, you made my reflection in the window way too concrete. It should be much softer and subtler. Remember, I'm sitting by a window and not a mirror." I felt the reflection in the drawing could not be improved upon.

"You need to work a bit on preserving symmetry in the context of perspective. See what you did here: if the woman in this drawing were to bring her right foot forward next to her left it would be much too big. Likewise, if she sat square her left breast would be much smaller than the right."

"Maybe I did that on purpose." I said defiantly.

"No heterosexual male would ever willingly alter the natural symmetry of my tits. The inconsistency in your scale shows you need a lot more practice."

"Uh uh! I don't accept that." I protested. I was the best person on the planet at drawing tits.

"Changing the wine from red to white was a good move, but I deliberately chose the bottle because I knew the abstract shapes on the label would be difficult to translate from a round three-dimensional contour onto a flat surface. Changing the label was just a cop out." My heart sank. Perhaps she had a point.

"What's with the hairy bush? This isn't exactly the seventies. On the bright side, I like how you did my hair and face. That's a pretty cute expression, and I really hate my mole as it appears in the mirror. I guess you don't like it either."

"No, I like your mole."

"Then why did you change it?"

"You're just nitpicking." I accused. None of these errors were of consequence. It was still a very beautiful drawing.

"Perhaps, but attention to minutiae is what distinguishes the true professional artist from the enthusiastic hobbyist."

Enthusiastic hobbyist! I couldn't believe what I was hearing. "You think you can do a better job?"

"You're damn right I could to a better job."

"Do it then."

"Okay then. You model. I'll draw."

As Cas set my drawing aside, placed fresh paper on the easel, and sharpened her pencils, I just stood there bewildered, not fully comprehending the events that just transpired.

"Hurry up and strip!" She ordered. "It's getting late. Unless of course there is something you don't want me to see."

"Oh, I have nothing to hide." I said assertively.

"Then strip!"

As I undressed, Cas remained more focused on her preparations, which was too bad because watching me strip would have been a real treat for her. When she finally looked up, I flexed a bit and moved my hips slightly so my big limp dick would swing.

She rolled her eyes. "Yes, very impressive. I can tell you work out, but perhaps you need to spend less time at the gym and more in the studio."

"Huh?" I said involuntarily. How could she not be aroused by my toned nakedness?

"Just sit on the sofa already!"

"Okay."

"You're too stiff. You look like you're being interrogated."

I relaxed a bit and quit flexing some of my muscles. "Is this better?" I asked.

"No, that's actually much worse."

Cas barked orders about how I should hold my body, but I didn't fully understand her commands. Many of the words she used were technical in nature, and, having never modeled before, I had never learned them. As it turns out, "flexing your shoulders" means moving your arms up and not pumping up your deltoids. "Abduction" means moving your arm out to the side. "Externally rotating your hip" means pointing your knee outwards to the side. In the end she had to get up out of her seat and physically move my arms and legs in place. I was too bewildered to enjoy the brief moment when her saggy tits dangled in my face.

Sitting completely still was surprisingly challenging. My neck and back really started to ache. I also felt completely exposed. The way Cas looked at me put me ill at ease. Her expression wasn't that of admiration or lust, but rather judgement. The entire experience started to seem a little humiliating.

She marked and shaded quickly and furiously upon the paper in front of her, her face screwed up in concentration. Cas was an hour into her drawing before I realized she never bothered to redress. Her right breast would jiggle and sway as she moved her hand and elbow to draw. At times she would get irritated and bark, "sit still!" Which was a bit demoralizing because I thought I had been concentrating rather diligently on not moving at all. Perhaps I had not been giving the models at the guild their due credit.

As the sunlight faded, the tight knots between my shoulders began to relax a bit, and I started to feel a little less uncomfortable. My mind more at ease, I realized Cas was simply playing a game. There wasn't anything wrong with my drawing. She just needed an excuse to get me naked. Because I had called out her bluff, she had to work hard to produce something beyond a crude doodle to avoid being humiliated. If she truly wanted anything other than sex, she would have put her clothes back on. It was a little cold in the room after all. My dick even shriveled a bit, but it still seemed pretty massive.

"Try not to look so cocky." Cas said. Perhaps she was reading my mind, but, more likely, my expression had betrayed my thoughts. A minute or so later she announced, "Okay, there we are. I'm all done. Come take a look."

Cas stood up so I wouldn't have to look over her shoulder. She stretched her arms and neck, her big tits swaying. I studied the picture at length, but I couldn't quite comprehend what was in front of me. It was technically quite good. The proportions were preserved. The shading was consistent throughout the drawing. My reflection in the window was exactly as Casdoe previously described it should be, which must have been very hard to pull off considering the light changed dramatically as the daylight grew into evening. The drawing had captured all of my facial features without error, but the face just wasn't mine. The eyes were sad and the mouth looked worried. This wasn't the face of a man that could fuck practically any woman willing to give him the time of day! My pecs were gone, replaced with doughy man boobs. My stomach sagged. I seemed to be straining to keep my shoulders back. My arms and legs were thin, hairy, and unexercised. Worst of all, my cock was tiny. I could barely make out the end pushing its way through a tangle of course pubic hair.

"You like it?" Cas said. "I think I truly captured you, as a person, onto paper. As you can see, I changed my mind a bit. I decided your seventies theme had some merit and gave you a big bush too."

"That's not me!" I said angrily.

"It's exactly who you are." She said sternly.

"I don't look like it at all."

Cas was silent for a while. "What you don't seem to understand—why I brought you here today—was to try to teach you a lesson. When drawing the human figure, the artist shouldn't just reproduce, with a few modifications, what the eye can see. The artist should be able to capture upon the paper who the subject really is. This is who you really are."

"I am not that guy at all! That's the worst drawing ever!"

"On the contrary, I think it's one of my best. I think I'm going to frame it and hang it front and center. When someone walks into the guild, it will be the first thing that they see."

It took a while for Casdoe's proclamation to sink in. Alas, my jaw dropped, my eyes popped open wide, and I said, quite involuntarily, "no!"

"Oh yes, this is good art."

"No, that's not fair!"

"Why? You don't want people to know you have a tiny dick?"

"But I have a big dick."

"Oh, I know that, and you know that, but not everyone else knows that."

"That's just cold!"

"How big is it? Eight and a quarter inches long, five and half around. Yes, most impressive! But one would never know it by looking at my drawing, now would they?"

Casdoe's intimate knowledge of my dimensions was disturbing. "How did you know?"

"Your measurements? Heather told me."

"Heather told you?"

"Oh yes. I make it my business to know what's going on with all my artists and models, especially when one suddenly stops showing up at the guild. I called Heather. She was most upset. She wouldn't give me any details at first. But I put her at ease and eventually I was able to pry out some details. Let me see if I can remember what she told me. You two went out on a date. You took her back to your place. You started kissing. You both got naked. She was really impressed with your cock. You let her measure it, right? She told you it was the biggest one she had ever seen. And then what happened?"

"We fucked. She went home." I said. "People my age do that sort of thing all the time."

"Oh there's more to it than that." Cas sat down on the sofa, "When she was giving you oral, you kept grabbing the back of her head and pulling her forward, trying to cram your cock down her throat."

"Okay, maybe I was a little rough."

"Oh, you were more than a little rough. You had absolutely no regard for her pleasure, comfort, or feelings. You remember how you fucked her?"

"Not really. That was weeks ago, and I've been with a lot of women since."

"Okay, let me tell you how it went down. You refused to go down on her, right? Said you 'didn't do that sort of thing.' You made no effort to get her ready at all for that matter. You just spread her legs wide, jammed in your giant cock, and started plugging away. Then you pulled out and splattered her pretty face and perky little tits with your cum. You didn't give her any warning, did you? Your cum got in her eyes, and she said it burnt terribly. When you were done panting, you asked her if she had a good time. She told you the experience was a little painful. You refused to accept that, so you got mad and kicked her out. You didn't even give her a chance to get dressed. You pushed her out naked into the hallway for the neighbors to see and tossed her clothes out after her. You know, a cock as big as yours can be great, but it's very much a weapon if you don't use it properly. Not only did you cause Heather pain, you humiliated her after the fact."

"What can I say? Some people just can't handle a big cock."

"I've had a lot of cocks in my day. Some small. Some large. Most somewhere in between, and even a few that were down right tiny. On at least two or three occasions, I've had cocks even bigger than yours."

"No way!"

Cas shook her head. "Believe it or not, yours isn't the biggest, but it is, no doubt, very, very big indeed. I admit that I am no spring chicken and that I have been around the block many, many times. I can tell you this: It takes two to handle a big cock: the person receiving the big cock, and also the person wielding it. I know I can handle a big cock. I've done so plenty of times before, but how about you? Can you handle a big cock?"

"I know I can."

"But are you willing to put your money where your mouth is?"

"You know I am."

She looked over at her drawing on the easel. "Tell you what," she said, "I will give you a chance to show me you know how to handle a big cock. If you fulfill the deed to my satisfaction, I will let you take that drawing home to keep. Otherwise, it goes up in the guild. Do you think you are up for that?"

Oh, the games women will play to fuck me! Although I didn't appreciate the scolding, I didn't object one bit to where the evening was headed. "I'm up for it." I said confidently.

"Good," Cas said. "You can start with what you refused to do with Heather. She spread her legs wide and rubbed her fingers along her stubbly mons and meaty pussy lips. "I want you to get on your hands and knees and eat my pussy."

Giving oral wasn't exactly my favorite sex act, but I found Casdoe's assertiveness a major turn on. I quite willingly got on my hands and knees and started lapping away.

"It's a good thing your art isn't on par with your oral skills," Casdoe said, "otherwise you would starve to death, or, worse yet, have to find a job in real estate."

"You're just saying that to be mean." I protested.

"No, you're acting like a kitten lapping milk up from a saucer. You need to apply deeper and more steady pressure with your tongue."

The odor wasn't what I expected. As a matter of fact, it wasn't bad at all. I kind of liked it. I plunged my tongue as deep as it would go into her loose pussy.

"You shouldn't do that yet. You need to pleasure the clit first!"

I pressed her clit firmly with the tip of my tongue.

"That's not my clit. You're way too low!" I deflected my tongue upward. "No the clit wouldn't have any stubbly hair at the end now would it? It's not that hard to find. It's where my two big pussy lips meet at the top. It has a little knob at the end. Mine is fucking huge. You shouldn't have any problems finding it."

Down and to the right, I found what I was looking for.

"No that's where I pee. Man, you are pathetic. Just stop!" she said pushing my head away. She stood up and pointed to the sofa. "Here, lie down on your back."

I complied with her demands. Facing my feet, she straddled my neck and shoulders and shoved her ass and pussy into my face. Looking at my limp dick, she remarked, "You don't seem to be enjoying this, but that's okay. It's not always just about you."

Eager to get her on her back with her legs spread, I resumed my search for her clit. But in the shadow of her big ass, I couldn't see very well. "Here let me help you," she said, sitting backward and grinding her ass and pussy rather indelicately into my face. Under the weight of her generous ass cheeks, my nose bent painfully out to the side. Her pussy stubble caught and dragged against the soft skin of my cheeks. It felt course like sandpaper. Alas, I must have finally found her clit because she stopped gyrating and abrading my face with her barbed pussy. "Oh yeah, right there." She said, "I like that."

Casdoe's description of the clitoris had been wholly inaccurate. It didn't have a knob at the end. Rather it seemed a very tight hole with bumpy little skin folds radiating outward like the spokes of a bicycle wheel.