Free-Hand Drawing

"Mmmm, I love getting a good rim job. Perhaps you're not completely useless in bed after all."

The news was a bit of a shock. I admit I was pretty grossed out, but a part of me needed this woman to want me. I continued to probe her tight little anus vigorously with my tongue.

"You like the ass don't you? Mmm, me too." She said enthusiastically. "Do you want to ass fuck?"

It was hard to articulate coherent speech with my face full of fleshy ass, but Casdoe was able to correctly interpret my muffled "Blmmph" as an affirmative response. She picked her soft juicy backside off my face and stood up. "I'm going to need a few minutes to myself to make preparations," she said. She swaggered into her bedroom, her ass shaking and jiggling. She shut the door behind her. I couldn't see what she was up to, but I could hear the unmistakable rumble of a drawer being pulled outward. No doubt she had gained access to her arsenal of sex toys. For a cock my size, she would need a very large bottle of anal lube.

My monster cock was still a little on the limp side. I roused the serpent from his sleep with a vigorous shaking. I was eager, ready, and agitated when she finally returned from her room holding a bundle of objects in her arms. Looking at my thick, long, rock hard erection, she said "mmm, mmm, mmm, that is most impressive." She placed the bundle on the coffee table and started sorting through it.

She had her bottle of anal lube, of course, but also the long shiny thing that sort of looked like a hockey stick. There were also several leather straps, what appeared to be a large washer made from the same material as the hockey stick, a few non-descript objects made from silicone rubber, and a battery—not your typical double or triple A's, but an unusual size, the kind you find in really expensive electronics. I admit I felt a little perplexed by the rather unusual collection in front of me. Following my gaze Cas said, "lucky I remembered to charge my battery pack last night in preparation for your visit. When you reach my age, you tend to forget things." Her eyes darted back and forth, searching for something on the coffee table.

I picked up one of the strange objects made from silicone rubber. It seemed like a goblet, only with irregular surfaces and also with a long cylindrical hole running down the center.

"Oh there it," she said, nodding toward the object I held. "Do me a favor and lube it up for me." She handed me the bottle.

"What is this?" I asked.

"That," she said, "is a perfect three-dimensional negative image of my vulva. Do you know how hard it is to keep your pussy still when somebody else is making a mold?"

"I would have no idea."

"Oh it's hard. Much harder than modeling. You put an object in your pussy, your pussy just wants to clamp down on it. It took the guy like a dozen attempts before we finally got an acceptable result. The whole ordeal took hours and cost me a fortune."

"What do you do with it?" I asked, studying it. Its contours looked so foreign, like the landscape of an alien planet.

She sat back and spread her legs. "I want you to put it in my pussy. Slowly now. It needs to line up just right." I did as she said. "You've folded in one of my pussy lips, take it out please." When I was finished, her meaty lips were splayed out to the sides. It appeared she was pushing out a baby with a soft rubber head. "Okay now, the part that protrudes a bit, it has a groove behind it. Tuck my clitty into it. It's most important."

Following her meaty pussy lips upward to their origin, I finally found Casdoe's clit. "Hey, it kind of looks like a little cock." I said insightfully.

"Good for you. You finally found it." Cas's clit was about as long as the last two knuckles of my index finger, and just as wide. "Careful," she said, "it's very sensitive."

With the pussy mold in place, Cas gave me new orders. "Okay now, take the dildo and unscrew the cap at the end."

"You mean the thing that looks like a hockey stick?"

"Yeah, I suppose it does look kind of like a hockey stick. The cap is at the shorter end." I located the cap without too much difficulty and unscrewed it. "Okay, hold the shorter end downward and give the dildo a gentle shake." A small round cartridge fell out of the dildo and rolled across the surface of the coffee table. Casdoe instructed how to fill the cartridge up with lube. Next she had me insert the battery, screw in the cap, and turn the dildo on. It didn't vibrate or anything. I wasn't sure when "on" meant exactly.

The other piece of silicone looked kind of like a condom, only it had a hole at the end instead of a reservoir tip and fenestrations running down the sides. The sheath fit over the long end of the dildo and the fenestrations lined up with small slots I hadn't noticed earlier. "Hand it to me now," she asked.

Cas placed the short end of the dildo into the cylindrical hole that ran through the silicon mold in her pussy. "See how this works? The dildo is made of a space age composite."

"You mean like carbon fiber?"

"No, carbon fiber tends to dampen vibrations. For this application you want the opposite effect, vibration amplification. Also, carbon fiber is very stiff. This material has a bit of a give to it." She demonstrated, using both hands to bow the long end of the black dildo from side to side.

"Here, grab the end," she said. I wrapped my hand around the silicon condom. "Now rock it side to side a bit." I complied. Her stretched out pussy lips followed the dildo's movements. "The mechanical energy of every movement you make at the end gets transferred down the shaft into my pussy and onto my clit. It's as close to having a real penis as a woman can get. It's an object of my own design. I call it the 'robocock.'"

"It does look pretty space age," I agreed. I had seen nothing like it at my local smut shop.

"I had to consult with material scientists, electrical engineers, fabrication specialists. Oh, there's over $10,000 of parts and labor in me right now. Lucky most of the consultants were eager to waive their fee in exchange for a pussy ride or a blow job. Except the sculptor who made the mold, he was gay. Said my pussy was disgusting, and I think he even charged me extra." She sighed. "Can't win 'em all I suppose."

She rubbed her hand up and down the dildo the same way I stroke my own cock. "Sometimes at night I masturbate this way, but not often. It's such a pain in the ass to put together, disassemble, and clean. Mostly, I just take it out for special occasions." I liked hearing that my presence that evening constituted a special occasion.

"We're almost done." She said. The part that looked like a washer fit onto fine threads just beyond the pussy mold. The long shaft tapered, getting wider near the base, so the hole in the washer cleared the girth of the condom. Straps fit through slots in the washer and wrapped around her legs and ass.

She stood up and turned around. "Tighten the straps down." She ordered. "No, they need to be super tight. Make those straps bite into my fat ass." The straps disappeared leaving behind only long linear indentations, completely swallowed into the fleshiness of her generous backside. I gave her a playful slap on the bottom. Her ass jiggled. Sticking her finger in my face she snapped, "don't you fucking dare!"

"Sorry," I said, "sorry." I never felt this intimidated by a woman before. I didn't like it.

Casdoe regained her composure and smiled. "My cock is just over seven inches long and nearly five around. Not as big as your cock, but a good sized cock none the less." She stroked the shiny black shaft. "Oh, I forgot to show you the most important feature." She grabbed the silicon condom thing at the end and pulled it off slightly. Clear liquid oozed out the hole at the end and through the fenestrations at the sides. "It looks like I'm cumming, doesn't it? But I'm not. You see, if the silicon sheath gets displaced along the shaft, the robocock knows there's too much friction and adds a little lube. That way it'll glide smoother in your ass."

"My ass?"

"Don't look so surprised. Why else would I wear a strap on? You said you wanted to ass fuck."

Honestly, I had been so perplexed by the individual components of the device as we put them together, I hadn't realized we were assembling a strap on. "I thought I was going to fuck you up the ass." I whined. "Not the other way around."

"Mm, perhaps our contract was a bit ambiguous," Casdoe conceded, "however, the deal was that unless you handle a big cock to my satisfaction, my drawing goes up in the guild. You said you wanted to ass fuck, and right now I have a pretty big cock for you to handle, so let's have at it. Bend over!"

"I'm not up for this." I protested.

"Oh, I never said you couldn't back out, but if that's the case, the drawing goes on the wall. Why don't you think about it for a while?" she said, stroking her shiny black cock.

I could have easily seized the drawing and ran away with it, but the thought was too depressing. Artists steal ideas from each other all the time, but I had never before heard of an artist stealing another's work. I could rip up the drawing, but that would be the ultimate show of disrespect. Casdoe would be well within her right to kick me out of the guild for that offense. Casdoe's cock looked sinister, like part of an aerial drone that kills people overseas, but the drawing was much worse. I just couldn't stand the idea of people looking at it and thinking I was sad, flabby, and had a tiny cock. "Okay," I said sheepishly. "Let's get this over with."

Casdoe picked up the drawing and placed it behind the sofa, propping it up against the window. "I want you to look at this when I'm fucking you." She said, "there's still more lesson to be learned." She reversed the dimmer on the wall, bringing forth harsh overhead lighting. Through the window, the evening's gloaming vanished, replaced by the reflection of the room around us. Looking at her image Cas said, "I'm going to enjoy watching the both of us." I admit I felt very afraid.

"Get in position," she ordered. "Place your knees on the sofa and your hands on the windowsill." I had no choice but to comply. "Okay now move the drawing over a bit so I can see our reflections better."

I felt Cas's icy cold hands on my toned buttocks. She used her two thumbs to part my ass cheeks. "You have a nice ass," she said, "and a tight hole too. I'm going to enjoy popping your cherry."

I felt the hard end of the dildo press against my asshole. The silicon sheath provided almost no padding. "Normally I would loosen you up first with my fingers or a butt plug," Cas said, "but you didn't exactly prepare Jenna for anal did you? So why should I extend you any courtesy."

"You know about that too?" I said, tears welling up in my eyes.

"Like I said earlier, I always make it my business to know what goes on in the guild. When my best model suddenly quits, I want to know why. You know how many poser men would pay $80 to scribble her tattoos, tight ass, and tiny tits? Well, suffice to say that source of revenue is gone for now."

Casdoe pressed the end of her cock harder against my asshole. Unyielding, it kept her out for now, but the pressure hurt. I cried out.

"Jenna's husband only has a four-inch cock, and thin too. I had to squeeze my thighs together just to feel it. Your monster cock crammed into her tight ass and pussy must have been torture."

"You fucked her husband?"

"Oh, yes. She never knew about it, of course. I very much disliked the guy, but he was one of our main benefactors. Now, I'm sorry to say, that well has gone dry, and our funding is in peril. It's going to be hard to restore a steady flow of revenue to keep the guild going."

"I'm sorry!" I pleaded. Fear, more so than pain, caused the tears to run down my face. Casdoe's anger was palpable.

"Oh yes, you're pretty sorry alright." She grabbed my hips and thrust forward. My ass gave way, and her cock pierced me. I felt as if I were being stabbed with a knife. I screamed.

"Try to relax." Cas said. "You might even like it after a while."

My ass went into spasm around Casdoe's big cock. She took only short strokes but every movement was an agony.

"Do you want to know why I drew you with a tiny cock?" Casdoe said menacingly.

"No!" I pleaded.

"Because, in reality, you can't give a woman pleasure. You might as well have a tiny cock. Your big one is of no use to anybody."

Casdoe increased the tempo of her shallow thrusts. Over my sobs I heard the faint whirr of an electric motor. I felt a splash of cold liquid inside me. The robocock had begun to lubricate my tight rectum. I could no longer feel the hardness of its cold surface. Casdoe thrust deeper and harder. In her reflection off the window, she sneered.

"Take it," she barked, "take my big cock!"

Deeper and faster, her face relaxed a bit, lips loosening, eye's widening. "I love this tight ass," she said. She began to moan. "Oh, I'm cumming," she said, "I'm cumming." She stopped thrusting, and shut her eyes. The whole act had taken less than a minute, but it had been punishing none the less. My torment over, I pulled myself forward.

"Where are you going?" Cas said mockingly. "I didn't say you could leave. I'm not done with you yet."

Casdoe tightened her grip at the front of my hips, and began thrusting again. I didn't realize women could still function after orgasm. I figured that they were like men, and just wanted to roll over and go to sleep. I understood, then, that there were a lot of things I didn't know about women, that I was hopelessly ignorant about how to please them both in and out of bed.

Casdoe announced each of her orgasms. They seemed to get louder and longer as the night grew darker. I found if I didn't think about what was happening to me, I didn't hurt as much. I studied Cas's drawing. I could no longer argue that the face wasn't mine. Every fine mark was well thought out and deliberate, the freckles of my irises extremely detailed. Up close, the shading was an elaborate lattice of thin crosshatched lines, not the lazy marks I made with the side edge of my pencil. I could tell that, with the decades to come, my chest, arms, and legs would come to resemble those in the drawing. She had captured my body's image in the years ahead. The art was, without a doubt, a masterpiece.

I went numb after a while and didn't seem to feel Casdoe's thrusts anymore. I began to intuit things that didn't make sense. I could see Casdoe from behind, the tight knots of muscle in her shoulders tensing as she held my hips steady. I could see her ass jiggle and shake as she collided into me. I could see myself from the side, my head resting on my hands. I was having a bizarre out of body experience, a dissociative event.

Casdoe's voice brought me back to reality. "How do you like it?" she asked.

"This is awful," I said, "I'm so sorry."

Cas seized me by the hair. Grasping tightly, she pulled my head back. Her lips even with mine, she barked, "Liar! Tell the truth!"

"I love it," I said, "please don't stop.

Indeed, I did. My cock was rock hard and my breathing heavy and labored. Casdoe started to grunt, making loud, guttural animal noises. With both hands, she grabbed the corners of my mouth and yanked, pulling my head even with hers. She thrust in as deep as she could go. I could feel her pussy stubble biting into the skin around my violated asshole. "Oh my God! That feels so good! I'm cumming!" she shouting loud enough for the neighbors to hear. It was as if she had taken possession of my own cock. With her orgasm came mine. My nuts retracted into my body. Long sticky jets of cum shot out of my long, thick, throbbing cock. My jizm splattering Casdoe's drawing, getting all over my face and into those sad, sad eyes. Casdoe pulled out. The robocock made a sickening slurping noise as it broke the tight vacuum of my sore, red asshole. I collapsed onto the sofa and hugged my knees to my chest in the fetal position.

Casdoe seemed dazed. She staggered about the room. "I think I need another glass of wine," she said groggily, and wandered off into the kitchen. She returned a few moments later sure of foot and wine glass in hand. "Your debt is paid in full," she said. "The drawing is yours." She tossed me a soiled dish rag and said, "you're leaking all over my sofa. Clean yourself up." She returned to her bed room and shut the door. I used the dish rag to clean the jizm off the drawing, taking pains not to smudge any of Casdoe's meticulously drawn lines.

***

I asked Olivia, rather politely, if she could scoot her chair back for a moment so that I could sweep under her work station. She had that quizzical look you see on an artist's face when she is dissatisfied with her work but is unsure why. She had attempted a still life, a single lily in a vase, but it hadn't come out right. The oddly dysmorphic pedals very much reminded me of Casdoe's meaty pussy lips. Overcome by feelings of both longing and trepidation, I quickly excused myself to leave.

"Wait, come back," Olivia pleaded. "It isn't that bad is it?"

"No, it's good." I lied.

"No it isn't." She protested, "come on, tell me what I'm doing wrong here. I've seen your work. You're a good artist. Maybe you can help me out. Be brutal if you have to."

I had no desire to be brutal. "The vase, stem, and leaves look pretty good." I said. "But you are having trouble understanding how the flower is put together. You are focused too much on reproducing what you think are the outer contours of the pedals, which is a mistake because they fold back both downward and outward, producing a pretty complicated three-dimensional shape that is difficult to capture onto a flat page. Rather than drawing from the outside in, study how the flower is put together. Start from the inside out."

"What exactly do you mean by that?"

"Start over. This time draw the flower from the bottom to the top as if the flower was brand new from the florist and hadn't even opened up yet. Sketch very lightly. Obviously you don't see everything you need in front of you, but you can easily extrapolate upward where the closed pedals would come to a point. Draw in the margins of each pedal. Next, draw a rough circle that connects the points of each pedal as you see the flower now. Mark on the circle the point of each pedal. Finally, using the guidelines of your sketch, draw in the open parts of the pedal at the top of the flower. Start with the margins of each closed pedal, and peel each pedal back to the correct point in the circle. Make your marks darker as the flower finally takes shape."

Olivia thanked me, and I resumed my janitorial duties. Twenty minutes later a beaming Olivia found me in the next room and asked me to look at her drawing. It was much improved.

"Why didn't I see you at the last nude?" Olivia asked.

"I needed a break. I'm having issues." I said vaguely. "Who was the model?" I asked.

"I was." Olivia explained.

"How did you like modeling?"

"I liked it. Sitting still for an hour wasn't as hard as I thought it would be, but I felt pretty well prepared because I do yoga."

"I hear that helps."

"The hardest part was looking at all the drawings afterwards. You know, seeing how other people see me."

"The drawings weren't any good?"

"I wouldn't say that. Sarah's was good, but she broke my form down into abstract shapes. You couldn't really tell it was me."

"Yeah, she does that."

"Carl's was downright pornographic. It was pretty creepy."

"I'm not surprised. Carl is a pretty creepy guy," I concurred in a hushed tone.

"Most of the other's just made me look like a blob."

"You definitely don't look like a blob." I said empathetically. "That's totally unfair."

"Oh I don't think they did it on purpose, they were just­­—you know—untalented. I was hoping you would be there because you draw such good nudes."