Free-Hand Drawing

I didn't exactly know what to say, so a long awkward silence followed. I liked talking to Olivia, and I hoped she would change the subject. However, she decided to press the issue further. "So you don't draw nudes anymore?"

"Well," I said, "perhaps I did draw one recently. Would you like to see it?"

"Yes, of course." She said, enthusiastically. I retrieved my portfolio and showed her my drawing from the night before. "Oh, you have such a cute little pussy." Olivia said kindly, "but that's not a nude, he's wearing a fur coat."

"Technically it's a nude. That's how he came into the world. He didn't exactly put the coat on."

"What's your cat's name?"

"Gomez," I said. "He used to be a stray, but I adopted him."

"Oh, he's so cute. I want to go see him!"

"I don't know, it's a bit of a hike."

"Liar. Just the other day you told me you live right around the corner."

Gomez was sleeping in his spot in the sun on my chair in the studio. I let Olivia make a fuss over him, which he enjoyed tremendously.

"Hey is that Jenna?" Olivia said, noticing the unclaimed picture stashed in the corner. She picked it up and studied it. "When did you draw this?"

"About a month ago."

"Wow, that's really something. From this drawing you think she's seven feet tall, but she's so tiny, in reality."

"I thought that was what she wanted."

"Man, I wish I had tits like that." Olivia said. From where I was standing, Olivia's tits seemed much superior, but I did not vocalize an opinion. I thought I heard Olivia mutter something like a "tsk" under her breath.

"What?" I said.

"You made Jenna look really beautiful. I'll give you that, but looking at this drawing you'd never know she graduated magna cum laude from Yale."

"Like I said, I'm having issues with how I see people, especially women. It's why I'm not drawing nudes anymore."

"What about this one?" Olivia said, picking up Casdoe's picture. I made no effort to stop her. Her eye's darted back and forth, taking in every detail. Her gaze lingered only briefly on my tiny little cock. "This is like the best drawing I've ever seen. It's so beautiful, but your eyes! They're so sad. Is this a self-portrait? Is this how you really see yourself?"

"No, Casdoe drew it."

"Really? That's like every male artist's wet dream. What was it like, being completely naked in front of her?"

"It was interesting." I said. "It hurt a lot at first."

"Yeah, my neck and back get sore when I model despite all my yoga training."

I dismissed myself to feed Gomez. When I came back Olivia had her shirt and bra off. She had large shapely breasts but was firm and well-toned elsewhere. Her waist was tiny. I was impressed with her beauty, but, oddly, did not feel the need to possess her.

"What are you doing?" I asked calmly.

"I was going to model for you. I thought I could give you some practice—you know—help you work through your issues."

I smiled. "How about I buy you dinner instead?"

Olivia found my proposition acceptable. At dinner she talked about how she had an engineering degree from M.I.T. but that her first job in the real world was a disaster. She was the only woman engineer at the firm. All her male coworkers ever wanted to do was fuck her. Nobody ever took her seriously even though she had made the top grade at a far superior school. She had no real plans to become a serious artist. She admitted that her presence at the guild was just a distraction while she took some time off. She was starting a masters of engineering program the coming fall. I walked her home, and she gave me a peck on the cheek. "You're cute," she said, "just like your cat."

When I got home, there was a message on my machine from Casdoe.

***

I was punctual, five minutes early even. Casdoe opened the door to let me in. She wore an emerald dress and fine silver jewelry. Her hair was up and she whore bright red lipstick.

She looked me over. "I appreciate the effort, but that's not quite what I meant by business casual." She discretely herded me past a late middle aged man in an expensively tailored suit, someone of consequence, or at least someone of vast wealth. He held a glass of red wine and was studying the nude I had drawn the month previously. Cas had framed it and hung it high in her dining room.

"Hey that's my drawing!" I said.

"Shh," she said. Confident she had rushed me passed the man unseen, she stuck her head back around the corner and said, "we're just going to get set up really quick. Feel free to help yourself to more wine if you want. There's a bottle of white in the fridge."

She pushed me into her bedroom and quietly closed the door. Rummaging through her closet she took out a pair of dark slacks, a thin tie, and a button down shirt. "Quick, put these on," she ordered.

"Whose clothes are these?" I asked.

"My ex-husband. He is thinner than you, but they will have to do."

I changed in front of Casdoe. She seemed very nervous. The shirt was tight in the neck, and I had never tied a tie before. Casdoe tied it for me. The pants were even tighter than the shirt.

"Oh that won't do," Cas said, looking at my bulge. "Tuck your giant cock back between your legs."

I arrived at the easel feeling quite uncomfortable. Casdoe left briefly and returned with the model. She was tall and had a snooty look on her face. No doubt she was married to the man in the dining room. Casdoe helped her out the bathrobe and explained how she should lie down on the sofa. Taking her place behind me she whispered, "just do what you did with me when you were last here."

The model was late middle aged, but she had taken great pains to look much younger. Her hair had been dyed, and her tits were obviously fake. There were scars aplenty from plastic surgery, most quite faint or otherwise subtle. She was thin but muscular. Skin hung loosely in places. She wore a tight black choker necklace. My mind was immediately flooded with the image of her husband grabbing onto it for leverage as he fucked her hard from behind.

"The necklace won't do." I whispered to Cas. "It's too overtly sexual. Can you get her a hat, a big one?"

Casdoe mulled this over a bit. Eventually she left and returned with a broad brimmed sun hat bedecked with pink fake flowers, a prop no doubt. Cas wasn't the type to wear hats. She whispered apologies to the model and helped her out the necklace. Looking at the hat, the model wrinkled her nose, but Cas eventually persuaded her to put it on.

Casdoe took her place behind me. The sound of biting nails was a bit unnerving. I softened all of the woman's hard contours, hiding her six pack and wandering sartorius in a fictional layer of fat she very much needed in real life. I made her tits look real. I kept her nipples flat, even though they were long and agitated. The woman looked so snooty and entitled. I asked Cas to reposition the hat so that only her nose, mouth, and chin were visible from the front. In her reflection off the window I softened her expression, making her seem mildly amused as if somebody had just made a bad pun.

When I was finished, Cas herded me out of the room into the study. She came back with a cheap beer, said, "drink this," and left. I must have stayed there all by myself for at least a half hour. I drank the cheap beer. I could hear the soft murmur of conversation and occasionally Casdoe's nervous laugh. I heard footsteps getting louder. "They want to see you, briefly, before they leave." Cas said, looking much more relaxed.

The man in the tailored suit said, "this is excellent work! Thank you. You are very talented." His wife, now in a very expensive dress, was smiling.

"I will have the drawing framed and delivered to you early next week." Cas said. The man wrote her a check, and Cas saw them out the door.

"I need a drink," she said, "you want anything?"

I asked for another cheap beer. I followed her into the kitchen. She put the check on the table. From afar I could see many, many zeros. Cas told me to go sit on the sofa. The smell of expensive perfume lingered slightly. She returned with my beer and a large goblet of wine.

"I don't know what you saw back there, but let's just say the bill collectors are going to be very pleased with the guild. You did very good work. Were you nervous?"

"A little. I never feel comfortable around rich people."

"Well get used to it, because they are going to show the drawing to all of their rich friends, and all of their rich friends are going to want one too."

I loosened my tie and undid the top button of my collar.

"Oh you must have been so tense," she said, "I know I was. Let me loosen you up a bit. Here sit."

I sat on the floor in front of the sofa. Casdoe scrunched up her dress and straddle me from behind. She kneaded my upper back and shoulders with her strong hands and worked out some of the knots in my neck. I felt thoroughly relaxed, and after a while, Casdoe's ex-husband's pants felt very tight indeed.

"Now you do me," she said. We swapped places.

The fabric of Cas's dress felt uncomfortably coarse on my fingertips, so I undid the zipper down to the small of her back. She didn't seem to mind. I started with a light touch, gradually applying deeper pressure to the tight spots between her shoulder blades. Her back and shoulders were surprisingly well muscled. I kept catching my hand on her bra strap. In one quick movement, I undid the clasp. Through her dress, I saw her large sloppy tits spill downward. Cas turned around, but not quickly.

"Bras are so uncomfortable," she said, "I've been meaning to take it off, anyway. You look pretty uncomfortable yourself." she said, looking at the tight bulge in my pants. "Here, let me help you with that."

Casdoe unzipped my fly and took my cock out. It seemed even bigger than usual. Her grip could barely close around my massive girth. "That looks delicious," she said. She licked the underside playfully and then took me all the way down her throat. I could feel the tip of her tongue lick the front of my sack. I couldn't believe it. No woman had ever tried to deep throat me before. My cock was just too big. Cas pulled her head back. My cock was slick with slobber. The veins were engorged. I was rock hard. My shaft was streaked with Cas's bright red lipstick.

"Nobody can handle a big cock as well as I can," Casdoe boasted. "Nobody. Not even the sweet young things you like to gawk at back at the guild." She stood up. "Help me out of my dress," she ordered. I wasn't surprised to find out she wasn't wearing any underwear. Her bush was soft, cropped short, and well-manicured. She pushed me so that I fell back into the sofa.

She stroked her clit and meaty pussy lips with two fingers. "I am so wet." She said. Her pussy glistened in the lamp light. She straddled me, easing herself onto my big cock. Her big pussy had no trouble taking my shaft all the way in. I felt her soft meaty pussy lips stretch out and envelop the base of my cock. She rocked back and forth, grinding her big clit against the hard bone at the origin of my angry thick erection. Her breathing grew heavier, deeper, and more labored. I cupped both of her tits, one in each hand, and pinched a hard nipple between each thumb and forefinger. I could feel the wetness leak out of her and dribble down my nut sack.

"Oh that's so good." She said, "I'm cumming! I'm cumming!"

Casdoe quickly recovered from her orgasm. She crawled onto her knees and clutched the far arm rest with both hands.

"Stick that big cock back in." She ordered.

My thick cock spread her meaty pussy lips far apart as I thrusted vigorously back and forth. Each time my pelvis collided into her, a soft wave of flesh undulated up her cushiony round ass into the small of her back. Her pink asshole puckered. It seemed to wink at me, as if inviting exploration.

"Stick your finger up my ass." She said.

Her pink puckering asshole clamped down around my finger. Cas moaned, and the tension slackened.

"Now, stick your thumb up my ass."

I made small circular motions, gently stretching out her spicy anus.

"Stick your big, thick cock up my ass."

Casdoe's tight pink asshole gripped my cock firmly. Clutching the flesh at the front of her hips with my hands for leverage, I took short shallow strokes.

"Take me deep," she said. "Fuck my ass, hard!" Cas fingered her giant clit as I thrusted faster and deeper. Occasionally I could feel a sharp finger nail scrape against the bottom of my shaft. The slight pain was exhilarating.

"Oh, I love a fat cock up my fat ass," she shouted. Straightening out her elbows she pushed herself upward so her head was even with mine. I gripped her neck tightly with my hands and shoved my tongue into her mouth.

She pulled away, and shouted, "I'm cumming, again. I'm cumming!"

I made no effort to contain myself. Moaning loudly sticky bursts of cum exploded inside her. I could feel my hot goo welling up just beyond the tip of my cock. When I slid my soft cock out, a huge cum load poured out of her puckering asshole and stained the antique sofa. She didn't seem to mind.

Cas lay down on her back. Her ass and pussy gaped open. She sighed and closed her eyes. Her breathing became slow and shallow, and, for a while, I thought she had drifted off to sleep. "I just love big cocks," she muttered lazily.

***

I didn't sleep well. Although my second encounter with Casdoe was as gratifying as the first was punishing, something didn't seem right. At first light I put on my clothes and tried to sneak out. I was nearly out the front door when I heard her call after me. "I have never had a man walk out on me before. Never!" Cas seemed more concerned than angry. "Why don't you at least stay for breakfast."

Cas brewed a pot of coffee. She made me toast and cooked me an omelet. We talked about art and the guild. Eventually she asked me why I was in such a hurry to leave. "Didn't you have a good time last night? Don't you find me desirable?"

"I did, and I do." I said.

"Then what is it? My age?" Age was certainly a factor, but I told her otherwise.

"I saw you leave with Olivia the other day. She's the one you want, isn't it?" she accused, "you want to fuck her, don't you?" Casdoe looked genuinely hurt.

I thought this over. "Well, I don't not want to fuck her." I said. "I haven't really thought about her in that way, or at least not recently."

"Well what is it that you want?" Cas asked.

"I want to take her to the park and play Frisbee, and maybe afterword we could see a movie, one of those popular ones with lots of explosions, the type of movie I pretend to hate."

"You want a girlfriend, is that it?"

"Yes," I said, "I suppose I do."

"You've never really had a girlfriend before, have you?"

"No." I said, feeling ashamed. "Just one night stands."

"The more you care about someone, the more they can hurt you." Cas said. "I know from experience. My marriage ended very badly."

"I'm sorry to hear that," I said, "but I guess I'm willing to take that risk."

Cas smiled. "You've changed a lot in the last month." She said, "you're much more caring, less self-centered." She looked up at her nude self in my drawing. "It hasn't affected your art though. You're still the best I've got. We very much need you at the guild."

"I'm not going anywhere," I said and then asked, "so you like it then, the drawing?"

"Oh yes, it's excellent. I only told you otherwise because I felt I needed to cut your ego down a notch or two. I think I'm going to move your drawing to the guild and hang it front and center. It'll be good for business."

"That's good to hear." I said.

"What about the drawing I made of you? Did you tear it up?"

"No, I still have it. I think you should hang it up at the guild too."

"But people will think you have a tiny cock!"

"They will," I conceded, "but most can see well beyond it and come to understand the person in the drawing. For those that can't, I don't care. That drawing is very important to me."

"Why?"

"Because you made me beautiful."