Fortune Favours the Bold

Disclaimer: All characters in this fictional story are 18 years old or older.

Fortune Favours The Bold

Dillan couldn't help himself. They were right in front of him, slowly rising and falling with the steady breath of his mother. He had tried not to stare at them when his mother had entered the living room after her shower, only wearing her body clinging, blue silk robe. When she had sat next to him on the couch to watch the movie he had put on, he had resolved to just glue his eyes to the screen. As the flic had progressed though, he had discovered it to be harder and harder to hold to his resolution. Especially when his mother had lent against him for comfort, only for her eyes to gently flutter after a while, then slowly close.

Now, he couldn't stop staring at them. His mothers head rested on his shoulder, her legs laid on the sofa, as she continued to steadily breathe, giving him the vantage of his lifetime. Her breasts were large, but natural, and were only just covered by the blue silk garb. She wasn't wearing a bra, Dillan could tell, the outline of her nipples was slightly visible through her robe. After what felt like an hour, he couldn't hold back any longer and finally made his move, the movie all but forgotten.

Slowly, as to not wake her, he raised his arm, which he had draped around her before to hold her, and gently tugged on the silk band that kept his mother's robe tied together. He held his breath as it came lose and slowly released the knot at her waist. With a final slight tug, he managed to loosen it completely, making one half of her robe slide to the couch, revealing one perfectly rounded breast. He held his breath, marvelling at it for a moment, waiting for a sign that he had woken his mom. But no, she was still sound asleep.

Slowly he exhaled. Then, with steady fingers, he carefully pulled away the rest of her robe, exposing her other perfect breast as well. He suddenly felt light headed as he stared at his mom's boobs. Conflicting thoughts were running through his head. He knew he was not supposed to do this. And if he got caught.... He shook his head and tried not to imagine the consequences. All the while a voice deep inside his head whispered to him to touch them, squeeze them, bury his face in their perfection. His dick began to rise at the thought and without realizing he began to gently caress himself over his underwear.

As the voice slowly gained the upper hand, he began to reach out, almost trancelike, and gently cupped one of his mom's tits, as he continued to caress his cock. The boob was soft and round, everything he had imagined it to be. For a moment he just sat there, breathing shallow breaths, and held her in his hand. Then, the voice finally took full command and he whipped out his cock properly, beginning to stroke it while simultaneously massaging his mom's breast. It felt surreal but amazing. The possibility getting caught at any moment only spurred him on even more and he began to steadily pump his shaft.

After a few minutes of jacking off, he was almost ready to blow his load. His movement became jerkier. As he came closer and closer to climax his body twitched with excitement, accidentally nudging her. He froze, petrified, as his mom suddenly slumped forwards, her head slowly sliding down his chest and stomach. Panicked and unable to stop her momentum Dillan let go of his cock and her boob, raising both hands above his head like in surrender. His heart pumped heavily as her head came to rest right in his crotch, her lips gently grazing his shaft. He could feel her warm breath on his member.

For a moment he was unable to move. His dick pulsed, releasing a dollop of precum. His eyes were transfixed on it as it leaked from the tip of his cock and began sliding down its side. He couldn't blink as it slowly made its way down his member, leaving a glistening trail. It felt like time had slowed. Then, in slow motion, it reached the point of contact, where his mom's lips were touching his cock. He watched, unbelieving, as it touched her upper lip, then moved across it and finally vanished in her mouth.

He didn't move a muscle. Then, his mom moaned something unintelligible in her sleep. She licked her lips unconsciously, accidentally grazing the base of his shaft with her warm, moist tongue, and smiled faintly. There was no way of holding back Dillan then, as the voice in his head screamed for satisfaction. Before he could consider his next move, he was carefully pushing his hips forward, while gently lifting her head to rest it higher on his stomach. Then, he positioned his cock right in front of her slightly opened mouth and gently pushed it against her warm lips.

It felt amazing, the warmth of her breath right on his head, and her moist lips gently sliding over it. Finally, with the help of one hand, he managed to gently part them and smoothly slid his dick into his mother's mouth. The feeling was incredible and he revelled in the forbidden act as he began to slowly push his cock in and out of her. It wasn't a blowjob per se. He was just sliding his cock into a warm and moist cave. But the thought of fucking his mother's face did the trick anyways.

He moaned as he felt his mom's tongue graze his cock and he began to shove his cock into her mouth faster and deeper. With one hand he held her head steady, while simultaneously playing with her exposed nipples with the other. As he was getting closer, he felt his mom's body stiffen and shift under his grasp and he stopped in his movements, his heart beating in his throat. Had he overdone it? But no, it was just her adjusting her arm unconsciously, resting it on her stomach.

Dillan sighed and, more carefully than before, resumed thrusting his dick rhythmically into her. As soon as he had begun again, he felt his mother responding to the object in her mouth. She sealed her lips around him, almost reflexively beginning to suckle on his cock. Dillan tried to supress a moan as he felt the suction, his mom's tongue pressing against his cock. Carefully making sure her eyes were still shut, he resumed thrusting into her face, now with the added pleasure of her unconscious participation.

After a few minutes he was close again and began to ready himself to blow his load down his mother's throat. Gradually though, he began to notice a strange noise. It had been there for some time in the background, like a squelching. At first, he had thought it was just a result of his mom's lips, not quite sealing around his shaft. He slowly stopped his thrusting to isolate and locate the source of the noise, but it did not cease. His eyes fell on his mom's hand resting on her stomach. Or rather, it did not rest on her stomach, as it was tucked in between her legs, furiously fingering her unshaved pussy, producing the wet squelching noises.

Dillan froze in place as he stared unbelievingly at his mother's hand. Then, to his total shock, his mother slightly lifted her head from his stomach and began to bob it up and down on his cock by herself, resuming the suction, though now that all pretence was gone, actively caressing his cock with her tongue. Dillan was terrified, his mom was awake! But the voice in his head took control again. Clearly, she was into it.

"Fuck, mom," he moaned and let his head fall back on the couch.

His mom gave a suffocated giggle and continued to fellate him expertly. After a moment of pure bliss, just enjoying his mom's head game, Dillan reached behind her back with one hand and felt for her pussy, from behind. When he found her wetness, he plunged two fingers into her, while stimulating her clit with a third. She responded with a joyous squeal and wrapped her hand around the base of his shaft for a steadier grip, leaving her private parts all for him to explore with his fingers. His other hand he nestled in her hair, slightly guiding her pace.

Thus intwined, they went at it for the next several minutes, all the while moaning in pleasure and caressing each other with a free hand. Dillan was close again; he could feel it.

"Jesus, you are good at this. You like sucking your own son's cock, don't you," he asked.

In response, his mom released his cock into her hand, continuing to stroke it, and answered, "You're one to talk, you shoved your dick, in my mouth in the first place!"

Dillan just pushed her down on his cock again, there was no resistance. Then, he thrusted again, deeply. His mom did not resist this either, taking the length of his cock down her throat. It was an incredible feeling, the tightness, the moistness, the warmth. And best of all, the knowledge, it was his mom's willing throat. Continuing to fingerbang her as well, he could feel her body suddenly tensing. She was about to come, he realized. That send him over the edge.

"Fuck, mom. I'm about to...," was all he could manage, before she plunged him fully into her throat, her nose to his balls.

At the same time, he could feel her body go into ecstatic spasm, and he increased the intensity fingering her pussy, his hand almost cramping at the effort. Then he exploded. With a groan he shot load after load of hot cum right down her throat. He couldn't control himself, pressing his mom's head into his crotch, holding her. Then his mind went blank in extasy, he could not see anything, like staring into a lamp for too long.

When his mind returned to him, he was still holding his mom's head down. He gently removed the pressure and slowly his mom raised her mouth from his cock, letting it slip onto his stomach. They were both panting. She sat up next to him, and for a moment they just stared at the tv, not saying anything. Then his mom wiped a little bit of his cum from her lips and sucked it from her finger.

"Fuck," she panted, "that was hot!" Dillan didn't know how to respond, so he just turned and looked at her. She was smiling at him, a gleam in her eye. Leaning in, she gave him a peck on his cheek. Then she got up. "Guess I gotta go shower again. I'm dripping with sweat." Without closing her robe, and with swaying hips, she made her way to the hall way. In the door frame she halted and looked over her shoulder. "Wanna join me," she asked seductively. Dillan almost fell as he scrambled to climb over the couch.