Win/Win Situation

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Escaped prisoner has his way with her.
4.3k words

Part 1 of the 2 part series

Updated 10/19/2022
Created 03/17/2004
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Over two months had passed since Jake Barlow escaped from the prison in Tennessee. The first two or three weeks had been rough. First, on foot, he'd headed for Gainesville, Georgia, because that's where a buddy of his had been living the last he'd known. When he got there, however, he learned that his friend was long gone. The local news reports, because he'd spent some time in the area, made frequent references to his escape. And his old acquaintances couldn't show him the door fast enough. He was glad that none of them had turned him in.

The whole thing pissed him off. Sure he was guilty. He wasn't the kind of guy to whine about how innocent he was. But it was only a couple of minor burglaries. The judge, a doddering old motherfucker, got a hair up his butt and sentenced him to ten years without the possibility of parole. His lawyer, a young kid from the Public Defender's office, said it wasn't even legal. And then didn't lift a finger to make an appeal. Jake was sure that it was his Indian blood, his being one quarter Cherokee, that got the old judge all stirred up and made the punk kid apathetic. Shit. Double shit, fuck, damn.

Prison had been hell. He loved his freedom. And he didn't tend to like other men. A few buddies, and that was it. But God did he love women and there weren't any at the prison he'd been in. No inmates. Not even female guards. He'd been able to exchange photos of naked women with a couple of guys on the outside but, in a way, it made things worse. He'd look at the photos and it would almost make him want to explode. Imagining their warm soft bodies against his made him want to yell at the top of his lungs and go climbing up the bars of his cell.

He'd made it through four and a half years before he decided he had to get out. It took another eight months before he could work out a plan and make it happen. And now he was out, had been for nine weeks.

For awhile, in the early spring, after hitting the dead ends in Gainesville, he'd hung out around the lakes. Shit, he was a burglar by trade, it wasn't that hard to get his hands on what he needed. Clothes, food, a tent, and an occasional bottle of booze. The one thing he hadn't been able to find was a woman. And he was a passionate man. He loved to fuck. He was used to fucking a lot before going to prison. All that desire had backed up in his system. His balls were so full they ached and felt as heavy as lead weights. He had an almost constant hard on. While in prison he'd thought about finding a pretty boy and fucking some of that desire out but it wasn't the same. He couldn't do it. And no one sure as hell messed with him. He wasn't, by nature, a violent man but he was big and strong. A couple of short encounters with the meanest of the mean alerted everyone in the prison that he could take care of himself.

While living near the lakes, setting his tent up in remote areas, he'd begun using a pair of stolen binoculars to scan the waters for female forms. Often enough, usually on weekends, he'd see a few. He felt as if he was trying to drink them in through the eye pieces of his binoculars. One time he got lucky. He still found it hard to believe.

A man and a woman had dropped anchor in a secluded cove across the lake, about quarter of a mile away. The woman, much to Jake's amazement, had almost immediately taken off her clothes. Every fucking stitch. The guy had done the same but with less enthusiasm. And Jake didn't give a shit about the guy anyway. Oh Jesus, she was cute. Big bobbling boobs and a nice round ass. Delicious jiggles all the way around. He'd thought very seriously of swimming across and laying it to her. But decided against jeopardizing his sanctuary. As it was he memorized every detail of her body.

The couple swam to shore at one point and disappeared into the woods. Jake knew damn well what was going on. That sweet cunt was getting fucked. She had her legs spread open and a cock inside her. Jake hated to jerk off. It seemed like a waste. If he wasn't shooting his seed into or onto a woman's body it was a total loss, as far as he was concerned. But he had to jerk off now. He was taking her from behind, rutting like a dog, watching her big young ass quiver as he pounded into her. He could hear her moaning. She was saying, "Fuck me, God yes, fuck me." He could almost feel it. Almost see it. Almost hear. When he came it was like a freak of nature. Shooting sprays of pearly cum he tossed his head back and screamed like a panther. A male panther calling to his mate. But it left him feeling so empty afterwards. God have mercy, he needed a woman. A real woman. One as hungry to fuck as he was.

That was six weeks ago now and the memory of that cutie's naked body was still enough to almost drive him insane. His balls had that deep heavy ache again. And he couldn't remember losing his erection even once in all that time.

They'd almost caught him down at the lakes. A couple of boaters saw him and his instincts told him to get out. He was already on the move when the chopper started making passes over the place where he'd been. That night he'd stolen an outboard, pushed to the northern edge of the lakes, and then continued north on foot after sinking the boat. In a shed outside a summer cabin he'd found a dirt bike which made traveling a lot easier as long as he was careful not to draw attention to himself.

Now he was holed up not far from Dahlonega, Georgia. It was small enough for the cops to be laid back but big enough to supply the things he needed. And because of the tourist traffic and the University he didn't stand out like a dog at a cat party as he would have in most other small southern towns. Over the weeks he'd been here he'd begun to cautiously explore the area.

DARLENE JEFFERSON HAD THE day off. And she was feeling lazy. There was nothing she had to do so she'd taken her time getting out of bed, showering, and fixing breakfast. Now she was sitting at the table finishing her last cup of coffee and trying to decide what to do with the rest of the day. She had the TV turned on with the sound down low. The flickering images gave a kind of companionship. The news was on, she noticed idly. The photo of a man's face flashed on the screen. Oh yeah, Darlene thought, That Jake Barlow guy.

A couple of her friends had told her they were concerned about her living alone, as isolated as she was. The way the woods came right up to her backyard would make it easy for a man like Jake Barlow to sneak onto the property and do whatever he wanted with her. Yeah, right, she thought. I wish he would. I could use a man. But the last I heard he was down south.

The thought made her squirm a little in her chair. Even that quick passing idea had made her pussy respond. She could feel the familiar ache, the tightening of her clit. Her nipples hurt. This was the longest dry spell in her life and it was making her a little nuts. Sure she had her toys and she made herself cum on a regular basis but it was a poor substitute for having a man hold you in his arms and do what a man does. Especially a man who enjoys a hot woman.

And she was hot. Oh Lord was she. To feel the weight of a man against her skin. His hard cock plunging deep into her pussy. Or, even better, into the depths of her ass. Thinking about it was making her ache painfully. Time to think about something else.

But remembering what her friends had said about her backyard had given her an idea. It was about time she started working on getting some sun. With that in mind she put her breakfast dishes in the dishwasher and went to change into her two piece bathing suit. Within a short time she was lying on her stomach, after applying suntan oil, feeling the hot sun soaking into her skin. She'd unhooked the top of her bathing suit and was lying with her breasts in the cups. After about twenty minutes she decided to turn over. Usually she kept her top on but this morning, for some reason, she decided to leave it off. She rolled over onto her back and then sat up. She spread oil over her body, paying special attention to her breasts. It felt good to massage them. Her nipples hardened. She settled back and considered masturbating. But the sun made her drowsy. She fell asleep.

IT TOOK JAKE BARLOW a second to realize what he was looking at. He'd been reconnoitering the woods since early in the morning. He'd seen the roof of a house from some distance away but had wanted to make sure that there weren't any people around who might catch him by surprise. But, as far as he could tell, he was alone. He'd then begun to approach the house. Because he was thinking like a hunter, watching for movement and listening for tell tale sounds, the figure lying on some kind of mat in the open space between the woods and the house didn't quite register.

And then it slammed into his brain. Pushing the breath from his lungs. He stood there panting like an exhausted cougar. A woman. A half naked woman. He could see the brown circles on her tits even at this distance. His hard on got harder, if that was possible, and started to ache painfully. His balls seemed to swell. He felt his legs shaking. His body made the decision for him. He wasn't even aware of having had a conscious thought. He was moving towards her pulling off his clothes as he went. The thought crossed his mind that there might be a man in the house who'd come running out with a 357 magnum in his hand to blow this crazy half naked man away. But Jake didn't care at this point. At least he'd die happy. The last few yards he was naked. His cock jutted out from his body and was so hard it barely bobbed as he strode closer. And then he was standing, looking down at her.

And Jesus God in Heaven he liked what he saw. This was a real woman's body, full and soft. Large cushiony tits with brown nipples like big sweet berries. Round ass that could take a pounding. But the part he was most hungry to see was hidden by a piece of cloth. Well, not for long, he thought. He reached down, grasped both sides of the bathing suit bottom, and jerked it down the length of the woman's legs.

DARLENE HAD NO EXPLANATION for what she felt happening. Struggling up into consciousness her first thought was that a huge wind, maybe a tornado, had struck and pulled off her swim suit. It took her a moment to open her eyes. And when she did the reality seemed even stranger. There was a tall muscular naked man standing at her feet with her bathing suit bottoms swinging in his hand. With an impressive hard cock. She glanced at his face and the knowledge of who she was looking at made her gasp.

"Open your legs," he said.

She was numb. She couldn't think. She'd heard what he said and had gotten the gist of what he wanted but her body didn't want to function. What her friends had feared was happening.

"Open your goddamned legs," he said again.

This time the clear anger in his voice cut through her torpor. She hesitantly began to comply.

"Wider. Wide open. I want to see it all."

He scared the hell out of her. Her legs went as wide as they would go. He was looking at her with the intensity of a cutting torch. The same fierce heat. Against her will her body began to respond with a similar hotness.

"Oh God have mercy. Oh sweet Jesus," he said, as he looked at her gaping clean shaven pussy. It was as if he'd seen a man rise from the dead.

There was a powerful note of awe in his voice that made the heat rush through her. No other man had ever looked at her with the same feverous desire she could read in his eyes. She felt a trickle of her juice slide down between the cheeks of her ass. This was something she'd never experienced before. She'd never gotten so turned on so quick.

Without warning he dropped to his knees beside her and thrust two fingers into her cunt hole. It made her groan with pleasure. Her hips bucked up to take his fingers deeper inside.

He looked at her in astonishment. Meeting her eyes. Almost seeing her as a person. "Goddamn, woman, you are so wet. Oh shit I've missed this. Feeling my fingers in a hot woman's cunt. Oh Jesus Lord." He stirred his fingers around inside her. It embarrassed her to hear the wet squishy sounds she made. It was impossible to hide her arousal. And it felt so good. Which made her wetter.

As he finger fucked her with one hand he began running his other hand over her body. He couldn't seem to get enough of the feel of her skin under his fingers. He stroked her belly and sighed. And groaned as he caught the lolling weight of her breasts, plucking and playing with her nipples. With a moan he pressed his chest against her soft stomach and rubbed against her as his long hair fell over her right breast and shoulder. And then he was sucking her left nipple into his mouth.

JAKE FELT INTOXICATED by this woman's full body. By the sweet softness of her skin and the woman scent. And it was clear that she was responding to him. He could sense that she was still frightened but her cunt was crying for his cock.

"Do you want me to fuck you?" Jake asked, lifting his head and looking into her face. "Do you want to feel my hard cock inside you?"

Her nod was almost imperceptible.

"You're going to have to do better than that," he said. "Your cunt is drooling for it." He pulled his fingers out and straddled her torso. Grasping her breasts he pushed their pillowy softness around his big balls and the length of his cock. He grinned to see her eyes fix on the large purple head. "You want to feel that up your cunt? Fucking you? Talk to me."

Her eyes closed. "Yes," she said quietly.

"Louder. I can't hear you."

"Yes," she said.

"Yes, what?"

"Yes, I want you to fuck me."

That was all he needed. Seconds later he was kneeling between her wide open legs. He touched the head of his cock to the mouth of her cunt. "Oh sweet Jesus," he said. He felt the wet warmth close around the first inch. "Oh shit goddamn. God how I've missed this." He was trying to savor every sensation. But the need was too great. He couldn't help it. He had to be as far inside her as he could go. A moment later he was. He gave a deep groaning howl as he felt the warm grip of connection that only being inside a woman could create. "Oh yes. Oh God, yes," he sighed. And then he began fucking her.

DARLENE'S FIRST THOUGHT as Jake began fucking her was, Oh my lord, this man can move. He surged into her with the muscular grace of a large cat. His movements were fluid and powerful and she could feel him touching places inside her that she couldn't remember any other man hitting in quite the same way. She couldn't help but lift herself to meet him as she reached up and stroked his chest and thick arms with her hands. All her fear of him was gone. And as he felt her join him his movements became even more precise and thrilling although she couldn't imagine how that was even possible.

"Oh. Oh," she moaned. "I don't believe this."

Their eyes met and in that instant they were bound together in a tight ring of pleasure.

"You like to fuck, don't you Baby," he said, thrusting into her with long strokes.

"Oh God yes," she moaned, "when it's like this."

He pushed deep inside and began grinding his lower belly against her, engaging her clit. His eyes seemed to glaze over. Then he closed them. Throwing his head back, his face twisted, he grabbed her hips and pounded into her rough and hard. All delicacy forgotten. A second later he made one last hard thrust, went stiff as steel, and screamed like a wild animal. In her depths it felt as if someone had turned on a hose. And then she was coming too.

She assumed that like every other man she'd been with he'd have to stop and recuperate. Or maybe he'd simply stop. It startled her when, after a short pause during which he remained buried inside her, he began fucking her again. The only difference was a slight softness. And after a couple of minutes he was as hard as ever. God the man could fuck. It seemed that cumming had been a way to settle in; now he was getting down to business.

His hands and mouth were all over her. He teased and touched and licked and nibbled. He kissed her passionately, sucking her tongue into his mouth, thrusting his into hers. He nuzzled her ears, nipping the lobes. He kissed her neck. And sucked her nipples, licking her breasts. He was like a starving man who'd stumbled across a free buffet. He wasn't about to leave any part untasted.

And his hands. Caressing and clenching, running over every inch of exposed skin. Clutching her shoulders as he tried to thrust deeper and deeper. Cupping and squeezing her large pliant breasts. Plucking the nipples. Grasping the cheeks of her ass. It made her feel wanted in a way she'd never known before. It was obvious he couldn't get enough of her body.

And through all the kissing and licking and touching he was fucking. Trying different angles and new motions. Fast and hard one minute and then the next he was moving soft and slow. And he kept going. Like that battery bunny on speed. She wasn't sure how much more she could stand.

JAKE DIDN'T HEAR HER at first. He was too caught up in reveling in the sensations he'd been missing for so long. He loved everything about her body. She was so soft, and warm, and wet, and welcoming. She'd hooked her heels behind his knees. And when she was close to cumming she'd grab his butt and pull him into her. Moaning. Wailing with a lust drenched voice. He'd lost track of how many times she'd cum.

"You're starting to hurt me," she said, apparently not for the first time. "Hey. It hurts."

This time she got through. He stopped and looked down at her face.

"You're rubbing my pussy raw," she said. "It hurts."

Jake felt torn. He didn't want to stop; this was feeling too good. He was ready to fuck until the last ding dong of doom clanged and faded. But he didn't want to hurt her either. He was starting to like her a lot. Up to this point, once she'd gotten past her first fears, she'd been with him all the way.

"I love the way you're fucking me," she said. "I wish I could keep going but it hurts too much. I haven't been with anyone for awhile so I'm tender."

He looked at her, feeling a little angry. He was almost ready to start again even if it made her scream with pain. Then he had an idea.

"Turn over," he said as he abruptly pulled out and sat back on his heels.

"What?" She said.

"Turn over, goddamnit." With a look of confusion she rolled over onto her belly. "Now lift up your ass. Yeah, that's it. A little higher."

DARLENE REALIZED WHAT he was planning to do the moment he pushed into her cunt and filled his fingers with the slickness of his semen and her own lubrication and began spreading it over her rectum. Pressing two fingers in.

"Oh yeah, I love to be fucked in the ass," she sighed, feeling the familiar pain that she knew would soon turn to pleasure.

"That's good because that's what you're going to get whether you like it or not," he said.

He sounded mean but his fingers made sure she was ready for his cock. And then she felt the head of it sliding in. It felt so big. He pushed in further and her asshole began making its adjustment, she gritted her teeth at the discomfort. Then he was fucking her. Sliding slowly back and forth.

"Shit yeah," he grunted. "I should have thought of this earlier. Your tight little asshole is going to make me cum again. My balls have needed to be emptied like this for a long long time."

"Oh. Oh. Oh," she was moaning with every inward thrust. The hurting was gone now. She was feeling the kindling heat that would in time become the volcanic core of orgasm.

They continued for some time. Making little grunts and moans of pleasure. He began thrusting harder and faster."Oh yeah," he said. "I can feel it coming. I'm going to dump my cum deep inside your fucking ass."

The heat was building inside her. He'd been rubbing his hands over her back and ass, grabbing handfuls of her cheeks. Now he was leaning down and cupping her swinging breasts, catching her nipples in his fingers and pulling them.