Group Sex The Tales of Andrea & Dean

The Portrait

The show had ended.

After pulling the drapes closed on her floor-to-ceiling bedroom windows, Andrea walked shakily back to her desk, her legs still feeling wobbly after her explosive orgasm. She stood looking down at the screen of her laptop, her chat window open, her eyes glued to the bottom of their naughty text. She was waiting for Dean's response after she had revealed to him that she knew it was him, and not just some random stranger from the adult fiction website she was a member of. The cursor blinked, but no text appeared. After a few moments, Dean's avatar indicated that he had logged off.

Andrea touched her lips and smiled. She guessed that she had given him quite a shock--not just with her saucy strip tease and masturbation in her window in full view of the row of houses behind hers--but calling Dean out at the end of it. Her face flushed as she recalled her shameless display. How many people were watching me? she wondered. She stroked her chest and tummy, feeling her sweat cooling on her naked body. She shivered as she imagined her horny neighbours watching her stroke her vibrator into her pussy. She thought of Dean jerking his magnificent cock as he chatted with her and watched her from his balcony. She had not been able to actually see him, but she knew he was there.

Turning her bedroom light off, Andrea lay on her bed and stretched, her arms extending above her head before moving down her body, her fingertips brushing her labia, still wet with her orgasmic juices. She marveled at what a naughty minx she was becoming, and how horny and excited she had been exposing her soft, slim, sexy body to anyone who cared to watch. She shivered involuntarily and sighed, twisting her body in her sheets. It was not long before she was asleep, her dirty dreams a mystery to all but her.

It was a surprise and a disappointment to Andrea that Dean had made himself scarce over the following few days. She logged onto her chat account frequently, hoping to find him, or at least a message from him, acknowledging what had happened. She peered out her windows to his house, but only caught the odd glimpse as he moved from room to room. She hadn't even seen him jogging in the area, as he was usually keen to do. Did I embarrass him? she wondered. She could simply not understand why he had no interest in following up after she had exposed herself to him fully. She tried not to let it bother her, but in truth it did. She was a fit, attractive, desirable woman. Why was he avoiding her?

Despite this, she often found herself getting ready for bed in front of her bedroom window, the curtains pulled back, her light on. She routinely disrobed there, bending over excessively to remove her panties, pulling her top over her head painfully slowly to expose her b-cup breasts and rock hard nipples. Applying moisturiser to her skin. She even masturbated again, though more discreetly whilst lying on her bed. Often, she would notice Dean's bedroom light go out when she entered her room, and she was positive that he was watching her. Still, she had no contact from him.

To distract herself, Andrea took to doing what she loved: art. She spent hours in her small home studio painting, listening to music, and absorbing herself in her work. She was in the middle of touching up a painting when her concentration was broken by a knocking sound. She lifted her head and froze, listening. Yes, there it was again. A knock. She put her brush down and padded out of her studio listening for the next knock. Strangely, it did not seem to be coming from the front door.

She wiped her fingers on the tails of the man's striped business shirt she was wearing. She enjoyed painting wearing only a business shirt and panties as it made her feel more free and unencumbered. Today she had even forgone the panties, since her shirt hung low, just covering her bottom.

Another knock. It was coming from the back of the house. Andrea's heart skipped a beat. She quickened her pace and called out, "Coming!"

Rounding the corner, she smiled to herself as she saw Dean, his face up against the glass of her patio door, his hand shielding the glare from the window, peering in. When she came into his view, he started and jerked back, then smiled sheepishly and waved. She waved back, then opened the door for him.

"Well hello there stranger," she said, surprising herself with how cold her voice sounded. She realised then how much his absence had actually bothered her.

"Hi Andrea. Um, I brought you these. Cut them from my front garden," he said, handing her a small bunch of flowers.

Her heart melted at the gesture, and she couldn't help but smile as she took them. Still, she was not going to forget about why she was annoyed.

"Thank you. They're lovely," she said, taking the flowers and turning away from him.

She found a vase and filled it with water, placing the flowers inside and carrying them to the dining room table, where she set them down. She turned around and saw Dean staring obviously at her ass. She had forgotten how little clothing she had on. Her nipples instantly hardened under her shirt. She faced him again and crossed her arms.

"Um... how have you been?" he asked.

"Fine. Keeping busy. You?"

"Yeah, same. Working a lot."

An awkward silence. Andrea drummed her fingers on her arm. Dean was wearing a snug t-shirt with shorts and flip flops. She felt her excitement rise as she scanned his body. She couldn't deny her attraction to him. Still, she waited for him to speak. Then, she got an idea.

"Look--" he began.

'--I was just in the middle of something, Dean, but I'd be happy for you to come in and keep me company."

He beamed.

"Yeah.. yeah sure!"

He stepped inside and slid the door shut.

"Follow me," Andrea said, walking toward her studio, swaying her ass as sexily as she could.

She could feel the draft of air at her bottom, and on her pussy lips. She could already feel herself getting moist. She knew that Dean would have a fabulous view of the bottoms of her perfect ass cheeks, and her long, lean legs. Let him get worked up a little too, she thought.

They walked into Andrea's studio and she turned to him.

"Oh wow! You're an artist!" Dean said, sounding impressed.

His eyes scanned the room, picking over her paintings before coming back to ogle her body.

"You're very talented, Andrea. Seriously, I'm not just saying that. These are excellent," he said sincerely.

"Thank you. I do this work part-time. It's my passion. I'm mostly commissioned to do murals and portraits, but I do a lot of my own work when I can find the time."

"I'm impressed," he said, nodding and scanning the room again.

"Perhaps you could help me. I'd love to practice my sketching," Andrea said, moving her painting from the easel and replacing it with a large sketching pad.

"Um, ok. I'm not sure how much help I'd be..."

"You'll be my model, of course," she replied, grinning widely.

Dean laughed. "Oh, I don't know. I'm not much to look at..." he said modestly.

"Don't be silly. Come on, just sit there," she said, pointing to a nearby chair.

Dean shrugged and sat, leaning his arm on the back of the chair. Andrea chose a pencil and sat oh a high stool, crossing her legs. From this angle, Dean would have a clear view of her legs. She saw his eyes widen as her shirt slipped up to show off her smooth skin.

"Ready?" she asked.

"Sure. Go for it."

She began sketching him, observing the lines of his jaw, the roundness of his shoulders, the tapering of his waist. He sat patiently, and they made small talk for a short time. Andrea noticed Dean's eyes frequently glancing down at her legs and the side of her ass. he probably couldn't tell that she wasn't wearing panties from that angle, but he was still clearly excited by how much leg she was showing. Dean squirmed a little in his chair and looked at her.

"Look, Andrea, the real reason I came over today was to apologise for how I've been avoiding you. I mean, let's get this out in the open, shall we? I've felt so uncomfortable and awkward about this whole situation for days."

"What situation?" she asked, feigning innocence.

"Come on, Andrea. I watched you put on that show in your window that night, and I've watched you every night since. And you know I've been watching. You know that was my username on that site... I guess you saw that checked your browsing history and that you were a member too."

Dean chuckled and shook his head.

"I was so shocked when you revealed that you knew it was me. I thought you might be mad that I invaded your privacy or something. I just didn't know how to react. That's why I was avoiding you."

Andrea paused, observing him. Finally, she smiled.

"That's ok, Dean. I always knew you were watching, but I was annoyed that you didn't talk to me about it or anything. I mean, if we're clearing the air, let's get it all out: I watched you in my shower that first day we met. I saw you jerk off into my panties when I showered. I saw you take my bikini off and take pictures of me when I was sunbathing. I saw you stroke your cock over me while I lay there in my back yard."

"Wow... heh... ok, I guess that really does get things out in the open," chuckled Dean, rubbing the back of his neck with his hand.

"I wouldn't have shown off for you if I didn't want you to watch me. It's such a turn-on knowing you're stroking your cock while I strip down in my window at night."

"I have enjoyed every show you've put on, Andrea. To be honest, it's driving me crazy! You're all I can think about. I've been jerking off to those pictures I took of you in your back yard, fantasising about being with you," Dean said, squirming again in his chair.

Andrea looked down at his lap and saw the long bulge of his cock as it gradually hardened while they spoke.

"And I've been dreaming of you and that big cock of yours. I can see you're getting excited," she said, biting the end of her pencil. "You know, I think I'd prefer a nude model for this sketch. Do you think you can accommodate me?" she asked saucily.

"Anything for your art," Dean said, smiling as he stood up.

He pulled his t-shirt over his head, revealing his toned torso and strong arms and shoulders. His cock pushed against his loose shorts.

"Your pants too, honey," added Andrea, pointing with the end of her pencil.

He unfastened his belt and slowly pulled his shorts down, letting them fall to the floor and stepping out of them. His massive cock was clearly outlined in his boxer briefs, the head nearly poking out the bottom of the leg. Andrea's eyes roamed over his washboard abs, his lean thighs. She hummed her approval and squirmed on her stool. Her pussy tingled as she squeezed her legs together.

"How's that?" Dean asked, looking at her as she ogled him openly.

"That's wonderful, hun. But I've been showing you a lot more than that lately. It's only fair you do me the same courtesy."

"Fair's fair," Dean laughed, as he hooked his thumbs into his boxers.

He inched them down his hips slowly. Andrea was barely aware that she had leaned forward over her legs, eager to get a closer view. The room began to feel hot, and her cheeks burned. She twirled her pencil around a lock of her blonde hair as the thick base of Dean's manhood appeared below his neatly trimmed pubic hair.

"Mmmmm that's it, baby. Keep going," she said approvingly in a soft voice.

She inhaled deeply as inch after inch of his semi-engorged shaft was revealed to her, in awe and amazement at its length and girth. It was beautifully veined, and Andrea thought of how soft it would be to kiss, as she unconsciously licked her lips. Finally, his head popped free of the elastic of his boxers, bobbing heavily in front of her. She even gasped a little.

"Oh my god..." she whispered.

Dean let his boxers fall and stood with his hands on his hips, proudly displaying his enormous cock. After a few moments, he chuckled, his stomach muscles flexing.

"Aren't you supposed to be sketching me?" he said.

Andrea realised she was leaning so far forward she was nearly falling off her stool. She straightened up quickly and giggled.

"Yes, yes, of course. How unprofessional of me."

She began furiously sketching, her fingers deft and nimble, the scratching of the pencil on the paper the only sound in the room as her eyes flicked back and forth. She tried to concentrate, but the insistent itch between her legs grew. Her pencil flew across the paper--she was skilled, and captured Dean's form, his angles, shadows, and shapes, perfectly. She vacillated between her focus on her art, and her sexual desire. After keeping her attention on the page for a moment, she looked back at Dean to see that he was touching his cock; cradling its length in his palm.

"I hope it's ok if I move a bit. You look so beautiful when you're working. Your eyes are so alive, and your mouth... your lips move in such a sexy way. Not to mention how hot you look wearing that shirt."

"No, that's perfectly fine. Please, continue," she urged, blushing.

Andrea noticed her free hand fingering the buttons on her shirt. She began to unfasten them--a couple from the top and a couple from the bottom. Only two she left fastened, just below her breasts. She had uncrossed her legs, but the shirt tails still covered her bare pussy. She could feel her pussy lips slipping slightly on the leather stool. She was soaked.

Dean caressed his shaft and stroked it--long, slow strokes--invigourating it. Andrea watched it grow in his hand. Her pencil scratched the paper. Her chest rose and fell as she breathed more heavily. Her pussy burned.

"Do you like this, Andrea? Do you like sketching me while I stroke my cock for you?" Dean asked.

He appeared to be enjoying himself, and was becoming more comfortable, spreading his stance slightly and putting one hand on his hip as he masturbated.

"Oh yes, honey. God you look so hot. I've sketched nudes before, but not like this. Mmmm, don't stop, baby. Yes, that's so good. Point your cock up a little more, yes, like that. Ooohhh," she encouraged him.

Spurned on by Andrea's instructions, Dean gripped his cock more firmly and sped his pace. His hips began to move, subtly thrusting. He moaned as he watched Andrea work. The tension between them was palpable, electric.

"Yes Dean, stroke it for me. I've been dying to watch you do this. Jerk your big cock for me, hun," Andrea's voice rose in pitch as she continued drawing.

Dean stopped for a moment, noticing a large bead of pre-cum on the tip of his cock. He used his fingertips to distribute it over his swollen dick head, making it shine in the natural sunlight coming through the large studio windows. Andrea's mouth watered as she imagined what his pre-cum might taste like. She spread her legs apart and her hand slid down her body. She jerked as she touched her sensitive, swollen pussy lips.

"Let me see you touch yourself, Andrea. Please show me your pussy," asked Dean, resuming his firm, even stroking.

"It's not like you haven't seen it before, Dean," she teased.

"Please, Andrea. You're making me so hot for you, and I can see you're turned on too. Please touch yourself for me," he pleaded.

She paused from her sketching and gave him a devilish smile. She adjusted her position on her stool, bringing her ass forward and tipping her hips back. She lifted her legs, keeping them together, as if she were resting her knees on an invisible wall between them. Ever so slowly she parted her legs. Dean watched as she opened herself to him, her firm, milky thighs leading up to her cute, bare, pink pussy lips.

Being in such good shape, and keeping active with jogging, swimming, and yoga, Andrea was able to balance herself easily on the stool while she exposed her privates to her friendly neighbour. Her labia parted as her legs drew further apart, and Dean saw her wetness glistening on her beautiful vagina.

Dean visibly shivered as he beheld Andrea's womanhood, his hips thrusting more obviously, as if he was trying to resist the magnetic pull of his penis to her exposed cunt.

"Ooooh god, baby... you are so hot," he moaned.

She loved the power she had over him, and it excited her tremendously to have him look at her this way, her legs spread wide open for him, her pussy shining with her wet desire. Her fingers inched over her abdomen and down to her labia, her index and middle fingers parting in an upside-down 'V' above her slit. She pushed on her pussy lips, pressing them between her fingers and sandwiching her clit in between.

"Aaaaaaahhhhhhhh.... " she moaned, sighing deeply, her eyes half closed.

She felt a tremendous wave of pleasure course through her body and thought for a moment than she might cum right then. Her shirt was open up her tummy, exposing her belly button, and above, exposing her chest, but her breasts remained hidden. Her nipples poked obviously through the material.

"Take your shirt of, baby," said Dean.

"Ah-ah, not this time, hun. It's my turn to watch you," she replied, shaking her head and grinning. "Just keep jerking that beautiful cock for me."

"Oh god, Andrea, you are such a tease! Mmmm, I like it though. Ok then, baby, just watch me. Enjoy the show," he replied.

Using both hands, Dean now took control of his tool, pumping it and twisting his hands around his thick shaft, the head bulging out from his fist. He moaned loudly as he looked Andrea in the eyes, his gaze burning with lust. Andrea felt another wave of pleasure as she watched him, and began stroking her middle finger along her slit, teasing her clit and sliding on her abundant juices.

She had set her pencil down, and was gripping the back edge of the stool with her other hand. She looked down between her legs at her fingers--almost as if they did not belong to her-- as they teased her pussy lips. She sucked her tummy in and her body twitched as she brushed her sensitive clit.

"You look so wet," Dean said, watching her trail her fingertips along her slit.

"I am, baby. Watching you masturbate for me is making me so horny," she said in a husky voice. "Do you want to see me put my fingers inside?"

"Yes Andrea, please finger yourself."

Reaching up to her mouth, Andrea put her middle finger between her lips and sucked it briefly, before trailing it down her body. Her saliva left a small trail over her bare abdomen down to her slit, where she paused to rub her clit in small, tight, circles. Her legs twitched and she moaned. Her finger descended, slipping between her smooth labia. She looked into Dean's hazel eyes as she eased her finger between her hot, slippery folds, sliding it into her love hole and sighing.

"Aaaaaahhhhhh.... oooooouuu..." she moaned as she pushed her middle finger deep inside, pressing her palm on her mound.

She felt his gaze crawling over her body like a searing beam. Her head rolled on her shoulders as she moaned again, thrilled with the excitement of being watched so intimately, and enjoying the obvious pleasure Dean was getting from her shameless display. His eyes grew as she inserted her ring finger into her pussy next to her middle finger, dipping them into her soaked mound as if into a jar of honey. She loved the movement of his hips, the increased pace of his stroking hand, the tenseness of his muscles, the rising and falling of his chest, the wanton lust in his eyes.

"Oh my god, Andrea... I want you so badly..." he murmured, cupping his balls with his other hand as her jerked himself.

"I bet you wish your cock could switch places with my fingers, hmmm? Feel how tight, and wet, and ready I am?" she teased, pushing her fingers against the bottom of her hole, gently stretching herself, imagining his cock actually was entering her.

She shuddered at the thought, and heard herself cry out.

"I think you're wishing that too, sweetheart. Fuck, you look so hot. I can see your nipples poking through your shirt," he said, smiling.

Andrea looked down at herself, and sure enough, she noticed the nubs poking obviously against the cotton of her shirt. She arched her back and felt her tits press against the fabric, sending sparks over her chest, and spreading up and down her body. She heard Dean groan his approval.

"This is much better than spying on me in secret, isn't it Dean?"

"Absolutely... though you're still driving me crazy."

"Mmmm good. I want you to cum for me. I want to see that big load spurt out of your cock. Don't think I didn't notice how much you soaked my panties when you jacked off into them."

"Fuck, Andrea, I still can't believe I did that. But it was so hot... masturbating and watching you in the shower."

Dean's stroking was faster now, more urgent. Andrea could see the tension in his face, the tautness of his body. There was a table behind her, and she leaned back so she could put her hand on it for support, tipping her hips up further to give him a better view of her womanhood. She spread her legs further and began stroking her fingers in and out of her pussy quickly. Her skin broke out in goosebumps as she saw more pre-cum leak from Dean's cock head, dripping down into his fingers.

"Oh baby, you're leaking pre-cum for me. I can see how badly you want me, how your cock throbs to be inside me. Fuck, it's so big, Dean. I've never had a cock like yours. You would love how my tight pussy feels around it," Andrea said, growing in desire and enthusiasm.

She became aware that she was now just teasing herself. She DID want his cock inside her. She wanted him to fuck her deep with his big dick. She wanted to feel his hands grip her ankles as his thighs slapped against her ass.

"Yes baby, I want to fuck you, I want to feel the heat of your pussy against my dick head as I push inside you. Aaaaagh..." he grunted and moaned, his hand pumping fast along his thick shaft, his jaw clenching.

"Oh yes... oh fuck yes..."

Andrea's moans were high and loud. Her palm slapped against her wet labia as she furiously fingered herself, her legs shaking, her juices dripping down onto her asshole. She was moments away from pulling Dean to her and guiding his cock into her. She was going to beg him to fuck her. She needed that cock. Needed it now.

"Oh fuck, baby, I'm so close..." moaned Dean.

Andrea regained control of herself, realising how close she was to giving herself to him. Now she just wanted to see him cum.

"Yes Dean, cum for me. I want your cum," she begged, desperate to see him erupt.

"Yes baby.... yeah.... oh Andrea... I'm going to give you my cum... I'm going to cum for you, baby... oh god, I'm cumming!" Dean cried.

"Yes Dean... cum!" she echoed, her eyes wide, her fingers fucking her pussy in a blur of motion.

His whole body tensed and his hips thrust forward as he pulled back on his cock. A long, thick rope of pearly cum spurt from his dick head in a beautiful arc. It had power and distance, and splashed down along Andrea's outstretched leg and the top of her foot.

"Oh!" she cried, feeling the hot liquid touch her skin.

Her body jerked and what felt like a bolt of electricity raced through her. Her pussy clenched and her mouth opened.

"Oh Dean... I'm cumming too!" she screamed, driving her fingers deep into her pussy and curling them, pressing her palm on her clit.

She watched a second and third spurt shoot from Dean's cock, seeming to hang in the air before gravity took its course and brought them splashing to the floor. Her hips bucked as she watched him ejaculate, her orgasm wracking her body, her toes curling, a long, sustained cry of pleasure escaping her lips.

Dean grunted again, giving his erupting cock a firm stroke as he coaxed more spurts of his hot load out of it. Andrea was amazed at the velocity, the volume of his cum. Dean, for his part, was more concerned with watching Andrea have her own orgasm, her body twisting and writhing in pleasure. In the excitement, her shirt had shifted to expose her left breast, her hard, pink nipple pointing up at the ceiling as if celebrating its freedom.

A few more ejaculations spit from Dean's cock as he squeezed it and pumped it, the cum now leaking over his fingers and down to his balls. He was gradually regaining his composure as his orgasm subsided. Andrea trembled as she watched his breathing slow. She withdrew her fingers from her sopping hole and sucked them without thinking, still admiring Dean's body, his skin now with a slight sheen of perspiration.

She looked down at the floor and sighed at the white, gooey mess in amazement.

"My god, honey... that is a LOT of cum," she mused.

"That's how excited you got me, Andrea. Wow... that was... incredible," he replied, releasing his member to let in bob in front of him, dripping the remainder of his semen onto the floor between his feet.

"Seems you had some fun too," he added, grinning happily at her.

Andrea blushed, if it was possible for her to blush with already such a red face. She touched her sensitive pussy and jumped.

"Oh! Mmmm yes I certainly did."

Sitting up slowly onto the stool, Andrea closed her legs and put her hands on her knees, tipping her head down and letting her hair fall around her. She sighed, her head still swimming from her orgasm. She looked up, smiling groggily at Dean, who didn't seem to know what to do next.

"Whew! Oh, sorry hun, here," she said, retrieving a box of tissues from the table and handing them to him. Dean took several, and wiped his hands and cock.

"Sorry for the mess," he said, looking at the floor, and at her leg.

She looked down, having forgotten about his first shot that had splashed against her leg. She extended it outward, admiring the thick goo dripping down her shin and onto her toes.

"That's ok, darling. I didn't expect you to spurt so far, but it felt good... your hot load splashing onto my skin. It tipped me over the edge," she admitted.

She slid her fingers down her thigh and over her knee, trailing it through the cum. Gathering a bit, she raised her hand to her mouth and, eyeing Dean intimately, sucked his cum from her fingertip.

"Mmmmmmm," she hummed. "That's good."

"Wow Andrea... you are a saucy girl," chuckled Dean, his hands on his hips and a pleased expression on his face.

"You don't know the half of it," responded Andrea, pinching her nipple and giggling, before pulling her shirt closed to cover herself.

"I think I'll have a little nap now, hun. Thank you for stopping by, and for the flowers, and," she said, looking his body up and down, and then to the pools of cum on the floor, "for being my model."

Dean bent and picked up his clothes and approached Andrea.

"The pleasure was all mine. Well, almost all mine," he laughed.

Dean looking into her eyes affectionately, then turned his head to examine her sketch.

"Wow. That's really good! I'm impressed you could create such a good portrait in such a short time... under the circumstances."

Andrea looked at her work. He was right: it was good. Probably among the best quick sketches she'd ever done.

"I'll keep this for my private collection," she said, running her hand through her hair and winking at him.

"Well, I'll see myself out. But I hope to see you again soon, Andrea."

"Oh don't worry, Dean, you will. As long as you don't go into hiding again," Andrea replied.

She kissed her fingers, and lightly touched Dean's warm, soft lips.

"Until next time," she said, and watched him nearly trip as he left her studio, looking back at her longingly.​