Jessica’s Problem
By Jude

He often watched Jessica from his study window. She frequently worked in her garden on summer afternoons while he sat and typed away at his keyboard, stopping to look over and watch her. He knew she couldn’t see him behind his blinds and enjoyed the sight of her beautiful and peaceful form in the garden behind his house.

Today was the first day this year Mike had seen her, the long Midwest winter was over now and she was wandering around her garden again, picking at some leaves on her bushes and shrubs, apparently assessing her workload for spring. Jessica was a lovely creature who carried herself in a noble manner, upright and proud as she walked; her shoulder-length brown hair bouncing around in the breeze as she enjoyed the sunshine.

They had been neighbors for years. Jessica used to spend hours talking to Mike’s ex across the fence. Somehow the friendship between the two households never quite developed into a “come over and grill” one, something Mike was grateful for as Jessica’s husband wasn’t the friendliest of people. Although he’d watched her plenty, he hadn’t even talked to Jessica in over two years now. He hated yard work and since his wife had left him he had a service come around and take care of his most hated chore.

As he watched her solitary figure move gracefully around her garden, he vaguely recalled another neighbor telling him that Jessica now lived alone also. Her ogre of a husband had apparently up and left her late the previous fall. Like most neighborhood gossip, Mike had dismissed the information as irrelevant to him at the time, but as Jessica started to cut some small branches off a bush Mike found himself looking at her in a new light.

Now completely distracted from his work, Mike continued to watch her. She wore a sweat top, blue jeans, and was constantly brushing her hair away from her face with one or other gloved hand. Occasionally she would bend over, facing away from him. There was no way she could ever know what a delight it was for him, or that he was feeling a definite stir between his legs.

Mike smiled but dismissed his pleasurable thoughts of Jessica and returned to his computer screen. He was only partially successful though, and found himself unconsciously peeking out at her every now and again. After a couple of hours of glancing to see how Jessica was getting on Mike noticed that she had moved on to some heavier yard work and was attempting to lever a large rock with a shovel. He sighed as he watched her fruitless efforts for several minutes, wrestling with his conscience and his hatred of yard work. In the end his decision was made for him as Jessica’s hands slipped from the handle of the shovel, and she fell backwards onto the soft lawn.

Sighing as he retrieved his old work gloves from the garage, Mike stepped out into the warming spring air and started to walk in Jessica’s direction. “Stop.” He called jovially. “Stop, before you hurt yourself.”

“Hi Mike. Haven’t seen you in ages.” Jessica looked up and smiled, wiping some sweat from her brow with the back of her glove. “I was just trying to move this a few feet.”

“Well, maybe if I help you it’ll keep your health insurance down a little.” He quipped as he came through the gate and arrived at her side. “I’m surprised you haven’t broken anything already. Especially the handle of that shovel. Where do you want it?” He indicated the rock.

For the next half-hour Mike heaved at the recalcitrant boulder, laughed along with Jessica at their efforts and finally succeeded in moving the thing to its new site. Once the job was complete Mike sat on the boulder, still breathing heavily from his exertions and looked up at Jessica. “I hate yard work.” He laughed.

“Come on.” Jessica stood and started to walk back to her kitchen. “Least I can do is give you a drink for your hard work.”

As Mike sat at her casual dining table, watching her ferry lemonade and glasses from various points around the kitchen, he noticed again how attractive she was. Her silky hair hung nicely around her shoulders framing her subtle features and pale skin. When she smiled her face came alive though, her vibrant eyes shining and her lips parting easily and allowing her teeth to brighten the overall effect. He found himself thinking about wrapping his arms around her, something he had not done with a woman in far too long.

“First time I’ve actually missed the stupid oaf.” Jessica flashed one of her memorable smiles as she sat next to Mike with the tray she had made up.

“Ah, yes.” Mike recalled. “I heard that he’d left you. I’m sorry.”

“No need for sympathy. I’m happy to be rid of him.” She laughed a very genuine laugh.


Later that afternoon Jessica was preparing vegetables and looking out at her newly positioned rock, when she thought how nice it had been of Mike to help her and how good it felt to have someone in her house again. She’d enjoyed talking to him, something she’d missed with a man for the longest time.

Mike had never struck her as being overly attractive or even very social, but her opinion of him had subtly changed while he’d been helping her. He was taller than her, had less hair than her ex but today he struck her as being more athletic than she had noticed before. He didn’t seem to smile much, but his eyes were alive when they looked at her. His eyes gave him away more than anyone she had ever met.

Maybe it was fate, but more likely just plain habit, but when she looked at the amount of food she had prepared, it was far too much for her alone. The notion to invite Mike was the first thought that came to her, but she weighed it up for several moments before drying her hands and reaching for the telephone.


Mike wasn’t sure what to think of the invitation, but he sure wasn’t treating the dinner as a “date”. Jessica had insisted that he join her as payment for his hard work. His initial inclination was to decline as he had work to finish, but as he thought back to how much he had enjoyed her company that afternoon, he accepted.

As he showered before heading across the gardens to join her, Mike found himself fantasizing about what might happen if it actually was a date they had together. He thought about how it would be to hold a woman again, to kiss her and lie naked with Jessica while they made unhurried love all night. Looking down at himself as he rinsed, he found that he was amazingly aroused at the visions.

After he pulled on a slightly smarter pair of jeans and a linen shirt, he grabbed a bottle of wine from the refrigerator and set off to Jessica’s house.


“Come in, come in.” She greeted him happily, now dressed in a pink cotton shirt and a long, flowing, black skirt. “Dinner’s nearly ready. It’s been such fun cooking for someone again.”

Mike sat at the table she’d decorated with some small candles and watched as she effortlessly moved around the kitchen finishing their dinner. In the lounge she had some soft music playing and in the fireplace a fire was gently burning. For the first time, Mike started to see the evening as a potentially romantic one.

Over the meal he discovered two new things about Jessica; that she could cook, and that she was excellent company. It was her who steered their conversation though a wide range of topics, all of which she could talk intelligently on without ever seeming to either become bored or risk boring him. When their dessert dishes were empty it felt like the most natural thing in the world to take their wine glasses and retire to the lounge, add a couple of logs to the fire and settle down.

Mike chose a seat on the sofa close to the fire while Jessica chose to sit on a shaggy rug in front of him. “You don’t mind if I sit down here do you?” She giggled as she sipped at her wine.

“Not at all.” Mike sounded relaxed as he stretched his legs. “It’s a nice spot.” He caught her eyes as they sparkled with the flickering flames. She looked truly gorgeous in the dancing half-light.

They continued to talk easily, even when the subject turned to living alone after a partner had left. Jessica’s wounds were newer than Mike’s, but they found comfort in discussing past, present and future as equals. Mike found himself increasingly wanting to find comfort in other ways with her as she continually caught and held his eye as they talked. There was little doubt in his mind that she was feeling the same attraction, but something about their being neighbors and friends kept him just shy of taking it for granted. He decided it was time to find out though.

“I should really be going.” He emptied the last of his glass and looked down at her. “I don’t want to take up all of your Saturday evening. Dinner was so lovely. Thank you.”

Jessica hadn’t quite expected this and quickly reached out to symbolically touch his foot. “You don’t really want to go, do you?”

“Well,” Mike stood slowly, “no, but I don’t want to be in your way.”

“Tell me,” Jessica looked up at him, not moving from her sitting position, “what do you really want to do?”

He looked down for several seconds, weighing his words and feeling his pulse rise. “I’d like to come down there and sit with you a while.”

With a simple smile, Jessica’s arms opened and invited him to her floor.

Without breaking contact with Jessica’s intense eyes, Mike slipped down to sit on the floor. His hand came up easily to caress her cheek and feel the smooth skin that was flushed nicely by the fire and the wine. Mike leaned forward and brought their faces only inches apart. Jessica’s eyes softened as she closed the gap and pressed her lips to his.

At first their lips brushed and kissed with a sublime delicacy, but as soon as their mouths opened their tongues began to play like they were old friends. His hand retained its contact with her cheek while Jessica wrapped her arm around him and pulled them closer. He felt the gorgeous press of her chest on his as their kiss deepened and he brought his other hand to slide through the silken folds of her hair. Her hand around his back quickly found the edge of his shirt that had come out of his waistband and her fingers slipped underneath to touch his skin.

When she broke the kiss she continued to hold him close and look into his eyes. “I’m ready to try this with someone new, if you are.”

“I’m ready,” he watched as her eyes began to look a little watery, “but only if you’re that someone new.”

“I am.” She kissed him again, this time with an urgency and passion he was ready and eager to return.

When Jessica had pulled more of his shirt out from his jeans they started some synchronized unbuttoning; both slowly working down each other’s shirt. In the background someone was singing a soft version of Elton John’s classic “Don’t Let The Sun Go Down On Me” as Mike caught his first glimpse of Jessica’s pink satin bra. Without waiting to finish her remaining buttons, he slipped his hand inside her shirt and cupped her breast, feeling the weight soften into his hand as he lifted it through the sheer material.

She sighed and her hands paused as she felt him take hold of her. He had a wonderfully soft touch and it had been a long time since she’d been loved with such feeling. As soon as Mike resumed his job of taking off her shirt she tugged to pull his free and gently pushed it off his shoulders. She let her hands wander over his hairy chest, brushing over the nipples that immediately stiffened at her touch. As Mike pushed off her shirt off, she eased away from him and allowed him to pull it off her arms.

Mike returned his hands to cup both of her breasts this time, easing them up and gently squeezing with his whole hand. It was Jessica who reached behind, unclipped the bra and let the straps fall around his hands. This time when he withdrew his fingers the bra came with them, letting her breasts fall free to the air and his gaze. They were bigger than he’d imagined, with perfect nipples that looked almost purple in the fire’s light. As his hand took a gentle hold of one nipple and helped it to harden between his fingertips he looked up at Jessica’s face.

“You’re so beautiful Jessica.” He said quietly. “I want you so much.”

Jessica ran her hand up the inside of his thigh and came up against an unexpected bump at the top of his leg, feeling that he really did want her. “I want you too. Lie back. I want to take these off.” She tugged at his jeans.

Mike slid back on the rug while Jessica pulled at his belt. As he laid flat she shifted to her knees, undid his jeans’ button and pulled the zipper down. Mike gulped as he felt the zip release along the length of his erection and then eased his bottom off the floor so Jessica could start to pull his jeans over his hips. She watched his briefs appear, along with a sizable lump in them, as she pulled his jeans down his legs. Not for the first time that night she felt a distinct heat increase between her own legs.

As soon as his jeans were gone Jessica brought her focus back to his briefs, placing a hand firmly on the bulge and sliding the material downwards with a slow stroking motion. Mike watched her smile as the elastic waist of his briefs was pulled away and the tip of his cock appeared above it. With her hand now caressing the base of his erection and his balls, Jessica bent forward and placed a gentle wet kiss on the exposed tip. Lifting her head slowly away from his bursting cock, she pulled his underwear fully away from him, leaving his thick hard on horizontal with his body. She watched for a few seconds as he twitched a couple of times. It was a strong looking cock, long enough and definitely thick enough. It was very straight, the head was pointed and the rim was very well defined in this excited state. She imagined what it might feel like sliding inside her and felt herself squelch inside her panties.

“Now who’s the beautiful one?” She leaned forward to kiss him, running her hand along his length, before backing off to her own sitting position and beckoning him to come and undress her.

Mike kissed her first, his mouth urgently tasting her passion as he placed a hand around her back to support her as he eased her down onto the rug. While he paused to fondle her breasts again with his inquisitive fingers, Jessica reached out and took a light hold on his cock.

When he’d undone the zipper on her skirt, Jessica raised herself to aid his task and felt the material slide over her hips as Mike pulled it away to reveal a small pair of pink panties that matched her bra. As he brought a hand to ease between her legs Jessica opened them willingly and allowed him to finger the front of her panties lightly. He felt his own breath deepen when he touched the heat she was generating and the gentle contours of the pussy beneath the pink cloth. Looking up to her face he saw that her eyes were closed as she enjoyed his touch, her hand maintained contact with his cock though, stroking very gently, encouraging him.

Jessica’s legs continued to widen and her knees lift as Mike stroked the outside of her panties, now with an increasing pressure. Leaning forward, he kissed her deeply and moved his hand deftly to slip inside the panties. Jessica’s kiss paused for a few seconds as Mike’s fingers found her silky wet folds and allowed his fingers to slide along them, then her tongue urgently kissed him back and her hand squeezed him a little harder.

As she lay at his mercy, Mike pulled away her panties, leaving her naked and glorious in the soft firelight. Between her open thighs he saw she was shaven below a neatly trimmed triangle of dark pubic hair. While he returned his hand to her pussy and made slow and gentle strokes along its length Jessica raised herself to a sitting position that allowed her to kiss him and take hold of his throbbing cock again. Mike shifted to sit directly in front of her, their legs overlapping. Now they could kiss, he could continue massaging her pussy and now reach up to play with her nipples alternately. Jessica continued her slow affectionate stroking of him and could now ease a second hand down and let her fingers close around his balls.

As he continued to rub his fingers along her wet opening, Mike began to feel her clit swell as Jessica’s excitement built. Now as he stroked his fingers downwards he let his middle finger part her lips and slip inside her. She gasped and shivered with pleasure, her head moving forward to kiss his shoulder as her passion continued to rise.

“God that feels good.” She breathed into his ear.

Mike sighed deeply as he explored her velvety inside with his finger. Her small movements on his cock were having a serious effect on him now. “It all feels good.” He whispered back as her hand started to stroke the head of his cock with a swirling motion that sent shivers through him.

Knowing there was only so much of her expert manipulations he could take; Mike lifted one of her breasts upwards so he could dip his head and lick around her stiff nipple. His added attention to her again momentarily halted her movements as she caught her breath while another new pleasure wave washed over her. He continued to make his tongue swirl around her nipple and occasionally take it between his teeth and suck on her, enjoying the reaction he got as Jessica’s earthy breathing punctuated his movements. Finally withdrawing his finger from her, he immediately replaced it with two fingers and allowed his thumb to start some very gentle rubbing around her clit.

“Oh God.” She panted into his ear, letting go of his cock and grasping his shoulders. “It’s been years since anything felt this good.”

Mike continued his slow manipulation with his fingers, in and around her pussy, and his lapping at her nipple with his hungry tongue. He could feel her pelvis begin to grind into his hand as he played with her increasingly soaked sex. There was less warning than he expected when she came.

His fingers felt wonderful, gently pressuring her from the inside as his thumb teased her clit from the outside. Jessica had already involuntarily let go of his cock as she struggled to maintain control of her muscles, the pleasure folding over her like a huge warm blanket as Mike coaxed her nerves to an increasingly high precipice. Her rise to the point of no return had been so slowly delivered by his expert hands that the moment she tipped over almost took her by surprise. Her body was already tingling as her climax started, rushing through her like a runaway train and sparking her head with fireworks and spasms of pleasure. Her pussy suddenly felt molten as the fire and wetness fused into a boiling cauldron of ecstasy.

Mike felt her breathing suspend as her body froze in the first moments of her climax. Then, as she started to spasm, he wrapped an arm around her while he continued to slowly rub his thumb over her clit as her pussy contracted and clasped his fingers in a vise-like grip. As she collapsed into his arms he eased off his movements, pulled away his hand and wrapped his arms around her.

“Oh . . . wow.” Jessica giggled eventually, pulling her face back to look into his. “Where has THAT been all my life?”

Mike held onto her for the longest time, kissing her and letting her come down from the shattering high he felt from inside her. When she eased back from their sitting across from each other, Jessica was smiling and had her eyes locked onto his as she raised up onto her knees and inched herself over to where Mike’s cock was straining upwards between his kegs.

Holding onto his shoulders, Jessica positioned herself above him. Mike felt the slick heat of her excited lips brush over the head of his cock as she readied herself. Then, her eyes never leaving his, she slipped down to engulf him. The instant rush of his hardness penetrating her brought Jessica’s excitement level back into the red zone in a way she had never experienced before. Mike felt her softness close tightly around him and coat him in her hot juices. He could feel each pulse of his heartbeat as Jessica’s pussy walls echoed his throbbing cock’s every twitch.

From his sitting position Mike didn’t quite know how to move inside her. He was about to lie back when Jessica caught his neck with her hand and urged him, “It’s okay, stay there. I’ll do it.”

Kneeling, Jessica was able to rise and lower herself on him, very slowly at first as Mike pulled her close, kissing her and letting his hands feel the perfect skin of her back and sides. Every inch of him felt alive as all control of his pleasure was assumed by Jessica. He was breathing deeply before long; gazing into the face of his new lover and feeling a fresh intensity begin to build as his balls started to tingle.

He found a little room to spread his legs as her bottom continued to rise and fall on his thighs. Looking down between them, he watched the bounce of her breasts as she found the extra space he’d created and started to make her strokes a little longer. Down between their legs he saw a tantalizing glimpse of his own thick cock as it disappeared into Jessica’s spread pussy. When he looked up she was smiling at him, her hair tumbling over her shoulders and her hands reaching down to touch the lower part of his tummy. He gulped, knowing that he had no control over when he came, and let his hands clamp onto her bouncing cheeks as she steadily stroked him with her whole body.

Jessica could feel just from his skin that he was getting close. It surprised her just how close she’d become again so soon after her first climax and the thought of cumming with Mike inside her was suddenly very appealing. “Touch me Mike.” She whispered. “Take me with you.”

Reaching between them Mike found the engorged top of her pussy lips and the familiar bud of her clit; proud, slick and hot. He allowed his fingers to simply cover her first, his fingertips brushed by his own cock as she slid down him again, then he began some very small movements in time with the rhythm she was dictating.

The burn started almost as soon as he touched her; a long, slow fuse towards his climax that had a deep resonance to it that was beginning to shut down his self-control and relieve him of all feeling except the growing tingle. His balls felt like tiny pebbles pulled hard into the base of his cock as Jessica started to pant and whisper, “cum for me” over and over. It wasn’t like he had any choice.

As Jessica continued her steady pace on him Mike felt the familiar spread of warmth that he knew meant there was no turning back. He sped up his movements on her clit as his body tightened and the slow eruption of a massive climax began to radiate from his groin. He felt his body suspend in that state of bliss for the longest time he’d ever known, weightless and electrified as the orgasm ripped through him. He grunted loudly and felt his cock strain forever before the first massive spurt of cum gushed into Jessica.

A giddy smile was painted on her face as she felt Mike cum. Desperate to please him, her awareness of her own state was neglected momentarily, until she felt the spasms and gush of hot cum as he unloaded into her. The feeling of triumph was too much and Mike’s hand movements tipped her over the edge again, a second fiery orgasm dropping her jaw and closing her pussy around him tighter than ever.

Still sitting on him, her arms tightly wrapped around his back, Jessica listened to their breathing while the liquid ecstasy they had covered themselves in evaporated and left them sitting on a rug in front of the dancing fire.

When she eased off him and slumped to the floor Mike reached up to the sofa and pulled pillows down. He placed one under her head and laid the other next to it for himself. Their bodies glistened slightly in the warmth of the fire and the aftermath of the moment. He lay on his side and looked at her profile, listening as her breath slowly returned to normal.

“Hey,” Jessica giggled finally, “you think you’d like to come over for dinner again?”

Mike laughed, his mind catching up with all that had happened in the last hour. “Sure.” He sighed. “As long as I don’t have to do any more yard work to get an invite.”

“I wouldn’t worry about yard work anymore.” Jessica rolled over and looked into his face. “I’m sure I can find something else you can do for me . . . something you’re much better at.”

© Copyright 2005 Jude

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