I have been an artist all my life. As a child, the act of drawing, of creating pictures, became my creative outlet. Sometimes I drew scenes that I could see or remember; other times I drew scenes that I imagined. By high school, I was pretty good at drawing, earning high marks in art classes and winning some competitions.

The one thing that seemed to elude me was people. My landscapes and still lifes were consistently well-done, but my humans ended up looking a bit like cartoons. Then came Annette and Judy.

In the summer of 1990, I turned eighteen. Already registered in a visual arts program at the local university for that Fall, I made a resolution to finally master the human form. I searched through catalogues, magazines, and books searching for suitable models. For hours at a stretch, I would work away at an image.

Perhaps not surprisingly for a teenage boy, many of those models were attractive women, usually wearing skimpy swimwear or lingerie. I argued that this showed their body better and drawing bodies was the skill I was trying to improve. However, it also meant that drawing time often left me quite aroused. If I had the privacy to do so, I would pull my cock out and jerk off to a fantasy about the woman I was drawing. Otherwise, I held the image in my head until I could release in bed or the shower.

One afternoon that summer, I was hanging out with my pal Terry at his place. We went swimming in his pool, then lay in the grass to dry in the sun. We talked about our school crushes and speculated which of the girls we knew would look best in a swimsuit or less. I was a bit horny, and I guess he was, too.

Terry sat up and suggested, “Hey, no one else is home, Ben. Let’s hit Dad’s private cupboard.”

I grinned as I sat up. My friend’s father had a collection of men’s magazines tucked away in a cupboard in his workshop. Terry and I periodically raided that cupboard for stroke fodder. I was pretty sure that Terry’s dad knew based on some sly remarks he had made. Probably he just thought that teenage boys seeing naked women that way was part of growing up.

Inside, we each grabbed a few magazines. Then we settled on the floor in Terry’s rec room with the curtains drawn. For a while we browsed, occasionally showing each other a choice find.

Terry found a favourite model that he had jerked off to before. He slid his trunks down and began fondling his cock. I was still browsing, though my cock was getting stiff. Finally, a girl of the month model named Annette got my interest. She was a bit curvier than some, with heavy, prominent tits. A thick, dark patch of pubic hair covered her mound. Oddly, my first thoughts were about how to draw Annette.

Soon, though, I slid my swim shorts down to massage my cock as I looked over her photos. Terry had his hand wrapped around his cock, jerking it with some vigour. We often turned masturbation into a bit of a race to see who blew first.

I shifted a little as my orgasm rose, trying to make sure I kept my seed off of his family’s carpet. Terry and I were pretty good at cleanup but still tried to avoid it.

“Oh God,” Terry groaned beside me.

I glanced at him, seeing cum shoot up onto his belly and chest. Somehow, that set me off. I closed my eyes and let go, enjoying the warm feel of cum spattering on my skin.

With my sexual need appeased for a bit, I began looking at one of Annette’s photos with my artist’s eye. I had never tried drawing a full-frontal nude before. That would provide a good way to improve my skills with human bodies, I decided.

“Can I borrow this one?” I asked.

“Really like her, eh? She is a hottie,” Terry responded.

“I’m actually going to use her as a model,” I told him, “I am practising drawing human bodies this summer.”

Terry nodded and responded, “She looks like a pretty good choice for that, alright. Yeah, go ahead. Dad barely ever goes in there except to grab a mag or stash new stuff. It’s not like he keeps an inventory of it or anything.”

“Thanks, man. Let’s get cleaned up and then we can play games for a while.”

Annette lingered in my head well after that. Her spread was shot by a large swimming pool and in the neighbouring garden. In some photos, Annette sported a fringed white bikini; in others she was topless or nude.

Two photos drew my eye in particular. In one, she was nude under a large tree in the garden. She had slight tan lines on the bottom, a detail I could play with. In the other, she stood at the top of the pool ladder having just come out wearing only the bottom of the bikini. Her skin glistened from the water running down it, and her long, dark blonde hair was matted around her head and shoulders.

I decided the nude shot in the garden would be my starting point. The pool shot could be for later. Capturing the wetness of her skin and hair in that one would be an additional challenge, and I figured I should first get her body right.

On most weekdays that summer, I had the house to myself. Mom and Dad both worked full-time jobs. My older siblings had jobs and relationships in the cities where they went to university. They only visited occasionally on weekends. I did have part-time jobs doing casual labour, mostly lawn and garden work, for our church and for a couple neighbours. Those took maybe two or three mornings a week. Otherwise, I was free and on my own.

Once Mom and Dad were off to work on the Monday morning after I found Annette, I set about drawing her. I used Dad’s desk in the basement as a workspace when he was not around. It had two sections at right angles to each other, so I put the magazine open to Annette on one. My sketch pad and pencils were on the other.

As I worked at trying to capture the image, I focused on getting things right. I tweaked bits, tried things, experimented with techniques, and so on. A couple times I threw out my work and started over. Slowly, Annette took shape on my page.

At first, I felt no real desire or arousal even as I sketched her heavy breasts and muscular thighs. My gaze was constantly on either the photo or my rendering of it, but it just didn’t awaken anything. I was so focused on getting things right that the sexy aspect of the scene did not register.

Eventually I had to deal with the space between Annette’s thighs. Annette’s pussy wasn’t really visible, as was the case in softcore images of that era. I still had to fill in her pubic hair, though. Maybe for my next project, I could find a more hardcore image to try drawing actual female genitals. For the first time that morning, I found myself getting a little aroused. Something about focusing on that part of her body, I guess.

Lunchtime came around, and I decided a break was in order. After a sandwich and an apple, I changed into a swimsuit and took my sketchpad outside. Mom’s rose bushes were blooming, and I figured they would make a good still life. Maybe I could even use them in my drawing of Annette.

“Hey, Ben! How is my favourite artist?” called out a familiar female voice.

I glanced over at the yard to the west of ours. My neighbour, and my sister’s high school best friend, Judy, stood at the fence in a string bikini. The skimpy swimsuit covered barely enough to avoid indecent exposure.

My eyes drank in that sight. I had a crush on my sister’s friend on and off for a couple of years and missed her when she moved out for university. Seeing her again in sexy attire brought those feelings back with a vengeance.

“Hi, Judy. I’m good. I didn’t know you were home,” I responded with a smile.

Judy sighed and looked a bit sad.

“I had a rough year away at university,” she explained, “I was really homesick and... yeah, things weren’t going well. I took a leave from my program and came home. Got my old job at the mall back. Maybe I’ll transfer to Eversham College and stay home for university after this. Or take a year off, even.”

“Sorry to hear,” I said, “Coming home sounds like a good way to deal with it, I guess. Sandi isn’t home this summer, eh. She’s got some kind of internship thing going on in Toronto.”

“I heard. We keep in touch, and she knows what happened. I am actually kind of alone save for the girls at work. Claire and Rennie aren’t back either.”

“I am around,” I pointed out, “But I am not sure if I’m the company you want.”

Judy smiled. For the first time, I realized she was eyeing me almost the way I was eyeing her.

“Actually, you’d be great company, Ben,” she told me, “Maybe we can do some things together. Play games or hang out and watch movies or ball games.”

“Yeah, that would be fun,” I agreed, pleased by this turn of events.

“So you’re still drawing?”

“Yep. Going to study visual arts in university. Right now, I’m just sketching Mom’s roses. I might use them as a still life or in a bigger picture of some kind.”

“Cool. Can I see some of your recent work? You’re such a good artist. I have tried drawing but could never be as good as you.”

“Come on over,” I said, “I’ll give you a tour of my current drawing pad.”

As I waited for Judy to come around to our yard, I felt excited. The idea of spending time with my sister’s friend was a dream come true.

“Don’t get ahead of yourself,” I mentally chided, “She’s probably just looking for a friend, not a horny boy trying to get into her pants.”

Still, the prospect of time with my former crush seemed to create an opportunity I had not expected.

Judy arrived and stood by my chair. I flipped through my drawings, showing her some of my work from the past few weeks. For a few, I gave her some background. After eight or so fairly innocuous sketches, I flipped the page and was confronted by Annette.

“Oh shit,” I thought, glancing to see how Judy reacted. I had forgotten that my attempt at drawing a nude woman was there.

That’s when I realized that the way Judy was bending next to me put her tits almost at eye level. They were small and firm, nothing like the big boobs on Annette. I swallowed hard. Judy giggled.

“So you’re starting to do nudes now?” she asked, voice cheery.

“Yeah. I have been struggling with human bodies and faces,” I told her. “I borrowed a men’s magazine from a friend to try drawing some of the models.”

“That’s actually kind of a cool idea,” Judy said, eyes on the picture, “I like the look. You drew her pretty well.”

This positive reaction surprised and delighted me. It was encouraging. I had expected a frown or freak out.

“Thank you. I am thinking of doing some more.”

“You should get a live model,” Judy suggested, “I bet you could do even better with a real person.”

“You volunteering?” I quipped before thinking about the wisdom of doing so.

Judy looked at me, wide-eyed and smiling.

“Um, yeah, sure,” she stammered, “I’ve never modelled, even for photos, but I can try. Are you sure?”

Now I was a bit tongue-tied. Having the neighbour I had grown up around and crushed on as my model was an unexpected twist. Quickly, I pulled myself together.

“I would love it, Judy. Would you be okay posing in that swimsuit? I really want to focus on learning how to draw bodies, not just clothing. That swimsuit doesn’t cover much.”

Judy surprised me again when she responded, “I could even ditch the swimsuit if you like. I think I can handle being nude for art’s sake. Especially when I like the artist.”

I tried not to bug my eyes or drool. This was far more than I anticipated.

“So you’re really okay with posing nude?” I asked, a bit incredulous.

Her expression darkened, and I wondered if Judy was having second thoughts.

“Sure. I have been naked in front of people before, just never an artist,” she finally answered.

“Okay. So you’ll be my first live model. When? We probably need at least a full day. Then we will have time to try a couple poses.”

“Tomorrow?”

“I am working for Mrs. Cotter around the corner in the morning. Wednesday?”

“That works. My job is shift work, and I’m not on again until Friday. That gives us Wednesday and Thursday.”

“Deal. I’ll call you Wednesday morning.”

Wednesday was a grey, rainy mess of a morning. I had thought we might do the modelling session outdoors but not with this weather. Judy would probably not be comfortable posing nude out of doors anyhow. Too much risk of being seen by neighbours.

I called around nine, trying not to be too early or eager. Judy was ready, and her parents had gone to work. I headed straight over, taking advantage of a lull in the rain. Judy met me at the door in a bathrobe. The top was kind of loose, giving me a good view of her breasts.

“I am nervous but really excited,” Judy told me as we went down the hall. “I hope you like the setup. I used the guest room. It has a queen bed I can lie on for posing, and it’s nicely decorated.”

“That’s probably perfect, then,” I said. “I am nervous, too. I have known you for so long that the idea of drawing you naked feels a bit weird. Exciting, but a bit weird.”

“Have you ever seen a girl naked before?” Judy asked, “I mean for real, not photos.”

“No, I haven’t. I am, um, rather inexperienced that way.”

Judy gave me a friendly, but also kind of flirty, smile as we entered the guest room.

She had put a nice spread over the bed with an assortment of pillows. The curtains were open, letting natural light in. I assumed that Judy had already checked to ensure no one would be able to see in through that window. A chair and table were set up with a good angle on the bed. I guessed that was for me, so I put my sketchbook and box of art pencils on it.

“This works,” I said, “You did a good job. You could probably even do a photo shoot on this.”

“I like the idea of being sketched better. There’s something kind of romantic about posing for an artist,” she responded.

“There is something romantic about drawing a person from life, too. Ready?”

“Ready,” Judy said.

She untied the robe and let it fall to the floor. I swallowed hard and tried to stay focused on planning how we would pose this. It was not easy. My neighbour was fairly tall for a girl and slim. Her breasts were small and firm with a slight conical shape to them. Coarse, dark fur covered her mound, and I could just make out the lips of her pussy.

“Like what you see?” Judy asked, sounding more nervous than before.

“I do. You are, um, wow. Let’s get to it.”

I thought, but did not add, “Before I pop a boner and cream my shorts right here.”

“Okay.”

Judy climbed on the bed. We talked for a bit to work out a pose and get us both comfortable. Then Judy lay on her right side, head resting on a couple pillows. After a couple tries, we found an arrangement for her arms and legs that we both liked.

I sat down and flipped my drawing pad to a clean page. Carefully, I studied the shape of Judy’s body, then began to sketch the outline to start. I focused on things like the general shape of the head and limbs at first, avoiding the more erotic parts. Then I zeroed in on Judy’s face, working to get the eyes, nose, and mouth right. I drew in her full, red lips, wishing I was doing this in colour.

“They look so kissable,” I thought, even though I had never kissed a girl’s lips.

“Break?” I asked after I was mostly happy with what I had done so far. “I need to stand up and stretch. We can get you back in position using what I have sketched so far.”

“Sure,” Judy said as she shifted to a sitting position.

Her legs parted in a way that gave me my first good view of her pussy. The lips were pink and, it seemed to me, a bit moist. My cock stirred at that image. For once, I did not pull away from the sight. Instead, I studied her vulva and its surroundings with a view to how I might draw them. Perhaps for a second pose if we got there.

Judy did some stretches and other movements while I wandered around the room. Then we resumed our positions, and I went back to work. I finished my model’s face, then worked on detailing her hair. I was kind of glad Judy wore it short, though Annette’s long hair had been fun to draw. Then I filled out and detailed her limbs. Which then brought me to her breasts.

I was already in love with the shape of Judy’s breasts and her large dark nipples. For a minute or two, I fixed my gaze on them. The idea of touching them ran through my head. That stirred my cock to life in my shorts. I tried to ignore that feeling, wanting to focus on the art. Slowly, carefully, I added them to the drawing, working at getting the shading and shape correct.

“Break?” Judy asked, “I think my arm is going to sleep.”

“Sure, I could probably use a stretch myself.”

I stood and stretched, then flexed my fingers. They tended to tense up and even cramp when I worked for too long. Judy slipped off the bed and raised her hands over her head to stretch. That thrust those wonderful tits toward me. I gazed at them, noticing that her nipples were erect. Was this arousal or cold?

Then I noticed that my model was looking at me, gazing downward. I glanced down and saw the bulge in my shorts. Drawing my neighbour nude was clearly having an effect on me.

“You know, you could undress a bit yourself if it would be more comfortable,” Judy suggested. Her tongue slid along her lower lip, and she wiggled her eyebrows in a suggestive manner.

I stripped off my t-shirt. After a bit of hesitation, I dropped my shorts, too. That left me in tight white briefs. The bulge in those briefs was now quite clear. I returned to my chair; Judy got into position on the bed.

My gaze fell almost immediately on the space between her thighs. I sketched in her pubic hair, regretting that I did not have her position her legs to give me a view of what lay below.

“Are you as horny as I am?” Judy asked in a soft voice.

“Very,” I responded.

“Maybe we can take another break. A longer one,” she suggested.

Judy sat up and moved to the edge of the bed, legs draped over the side.

“That could be a good idea,” I agreed, stammering as I realized what my model was proposing.

I walked over to the bed and stood over my model. Judy stroked my face with her fingers. Then she caressed the bulge in my briefs.

“Do you want me, Ben?” she asked in a sultry whisper, “Because I want you real bad right now.”

I swallowed hard, nervous but also quite aroused.

“Yes, I want you. I, um, have for a long time, actually,” I told her, voice quivering.

“Then you shall have me,” she cooed as she pulled down my underwear to release my cock.

Judy pressed her lips to mine as she caressed my erection with her fingers. My quivering quickly went from nervous excitement to arousal as her tongue slid in to meet mine. I sensed that I would probably not last long but hoped she would understand.

“Get up here on the bed with me,” she said after a long kiss, “I know you’re probably in need of release. Let me get you off, and then we can take it more slowly from there.”

I lay down, and Judy got between my legs. She licked my stiff prick all over and kissed the head. Then she put her lips around my shaft and quickly took me all the way in. It was pretty clear that my neighbour had experience doing this.

With gentle suction and wet caresses from her tongue, Judy edged me higher and higher. Finally, I blew hard. My body shook and rocked with an intense wave of pleasure. Judy kept sucking, happily swallowing everything I gave her.

As my orgasm subsided, I went limp on the bed. My lover licked my cock clean, then crawled up alongside me. We kissed, and I tasted my seed on her lips and tongue.

“How’s that, my lovely artist?” she asked, her hand caressing my chest.

“Wonderful. That’s the most intense cum I have ever had.”

“Good. I wanted you to feel that way.”

Her hand strayed down and massaged my softening cock.

“My last guy used to recover pretty quickly. How about you?”

“I guess I do. I’ve jerked off two or three times in a morning if I am really horny.”

“And are you really horny?” Judy purred.

“I am naked with my dream girl. What do you think?”

Judy got on top of me, body pressed to mine, and we began making out. I ran my hands up and down her back, enjoying the warmth and smoothness of her skin. Then Judy shifted up, bringing her tits to my face.

“Lick them,” she urged, “Suck my nips.”

I did as asked, immediately enjoying the taste of her slightly sweaty flesh. I circled each nipple with my tongue, then pressed my lips around the left one and sucked. Judy shifted her body a little to straddle my thigh and rubbed against me. Her pussy left a moist trail along my thigh.

“Want a taste of me?” she asked.

“Yeah, sure. I really have no experience with this, though.”

“I’ll help, don’t worry.”

Judy moved up and straddled my face. Now I got a close-up look at her pussy. After a moment, I lifted my head to lick her. My first taste of pussy thrilled me. I kissed her down there, then probed her with my tongue. As I lapped at her genitals, I used my hands to caress and explore her toned ass and lean thighs. Judy gave encouragement and guided me to her clitoris.

“Feel that little bud,” she whispered, “Suck it, baby.”

I did as she asked. At the same time, I tried sliding a finger inside. She was warm and wet. I wondered how it would feel when I got my cock in. Judy seemed to like that, so I fingered her as I sucked her engorged clit.

Finally, my model let out a soft cry. Her body quivered, and her juices gushed out over my hand. I had made a girl climax for the first time. My cock was awakening again, aroused by my enjoyment of Judy’s pussy.

Judy dismounted and looked down at my cock. Smiling, she rested her head on my lower belly and licked the head. Then she took it between her lips and sucked. In no time, she had me rock hard and oozing precum.

“Ready?” she asked, “I want you to cum inside me this time.”

“Oh hell yes,” I responded.

Judy rolled onto her back and spread her legs. I mounted her and Judy guided my cock into position.

“Take me,” she whispered.

I slid my cock in. The feeling of her tight, wet vagina wrapped around my stiff cock was amazing. Slowly, I slid my cock back and forth, enjoying the sensation.

“Yes,” Judy hissed, “like that. Fuck me, Ben.”

My gaze locked with hers. Judy smiled up at me and ran her hands over my body. We paused, and I lay down atop her to kiss for a while, cock still buried inside. Then I lifted myself on my arms and began sliding my cock in and out again.

“Faster, harder,” she gasped.

Judy gripped my ass, pulling me in. To my surprise and delight, she whimpered, and I felt a gentle fluttering around my cock. Was she cumming again?

Finally, an orgasm gripped my body, blasting my seed into Judy. I shook and groaned as I kept hammering her until it passed. I collapsed on top of my model and tried to collect myself.

“How’s that?” Judy asked when I rolled off and lay still beside her.

“Wow,” I answered, a bit stunned. I had never expected to lose my virginity that day.

My model giggled and kissed me.

“It was ‘wow’ for me, too. Not bad for a first timer,” she said, snuggling against my body.

“You were a good teacher,” I pointed out. “Thank you.”

We cuddled for a while, then Judy asked, “Hey, can I see the picture?”

“Yeah, of course. Wait here,” I replied.

I hopped out of bed, grabbed the sketchbook, and returned.

“Here you go,” I said, passing the drawing to Judy.

She stared at it, looking almost shocked.

“That can’t be me, can it?” she said, voice sounding almost alarmed. “Am I really this beautiful, Ben?”

Surprised by this, I assured her, “You are, Judy. I just sketched you as I saw you on the bed. I mean, maybe my feelings coloured things a bit, but it’s definitely you. You really are beautiful.”

Judy sobbed and wiped away a tear.

“What’s wrong, Judy?” I asked, getting worried. “This has been wonderful. I didn’t expect this to become my first time, but I loved every minute of it, right from when I started drawing you. Please don’t be sad. You’ve given me so much.”

“Ben, I wish it was my first time, too,” she said, voice soft and sad, “In a way, it was. It was the first time I’ve really enjoyed sex.”

“Seriously? You seem pretty experienced.”

Judy took a couple deep breaths.

“I am quite experienced after the past year, but how I got there is not a happy story,” she said, voice quiet. “I’m sorry, Ben. I’m kind of used goods. I didn’t come home just because of homesickness. I got into a bad relationship. He preyed on my insecurities, manipulating me and making me distrust and hate myself. I crashed hard when I realized how badly fucked up I had become. My grades tanked. I spent whole weekends in bed moping and crying. Finally, I broke down on a phone call with Mom, and she encouraged me to get out of there. I didn’t even finish my term. Just left town and accepted DNFs in all my courses.”

“Jesus Christ, that’s awful,” I said, grabbing Judy’s hand. “Judy, don’t accept that guy’s opinion of you. He was an asshole, thinking only of himself and trying to control you. You are incredibly beautiful and have been so wonderful to me. I couldn’t have asked for a better first girlfriend.”

Judy smiled and squeezed my hand back.

“Oh God, thank you,” she said, sobbing a little, “Being with you has been a real boost for me. But I think I am done for today. My feelings are a mess. Can we do something else together and regroup tomorrow?”

“Sure. What do you want to do?” I asked her.

We were still holding hands and had moved closer together on the bed.

“Maybe we can play cards downstairs in the rec room? And talk more?”

“Okay, let’s do that. I’m game.”

“I’ll get us some lunch, and then we’ll just enjoy a game of something. I do want to model for you again, Ben. And, um, yeah. That, too. I hope I’ll be ready tomorrow.”

I squeezed Judy’s hand and kissed her lightly on the lips.

“That’s great,” I answered, “Whatever makes you feel better, okay?”

Judy kissed me back.

“Let’s go, Ben,” she said in a quiet voice, “I’m feeling better already.”

That night, I studied my sketch of Judy as I lay in bed. Her emotional breakdown surprised me. It never occurred to me that my art could show someone so beautiful, how beautiful they really were. For a while, I contemplated ideas for poses to try when we got together again, assuming she felt ready. Then I put the sketchbook aside and turned off the light.