Timing had never been Jake’s strongest asset. And when it came to his sex life, there wasn’t a time when his race to the finish line hadn’t caused a woman frustration. He was as useful as a sprinter running a marathon. The first few minutes were astounding; but all too quickly, it was over leaving his partner unfulfilled and entirely unsatisfied. Jake was as quick as they came, and it only took a few thrusts to bring the sexual encounter to a close.
“I can’t do this anymore,” Vanessa had told him while pulling up her jeans and tossing a shirt over her head. “I couldn’t be happier with your looks and charm, but the sex is a real problem. I don’t care if you have to see a therapist or buy a bag of toys and practice for months. Figure out how to fuck me without popping, and then we’ll talk.”
That had been three days ago, and he hadn’t spoken to her since. Vanessa had been right – he did have a problem. Fifteen second wonders were expected of high school virgins. But when a twenty-five-year old does it, it’s nowhere near as cute. His girlfriend was gone because of it, and Jake had no one to blame but himself.
Sitting on the bed in his college dorm room, Jake looked around the familiar surroundings with agitation. Every good memory it held was now tarnished by his own inadequacy and failure. He couldn’t stay there another second with thoughts of his ex swirling around inside his head; but most of all, he didn’t want to be alone. Jake quickly threw together a weekend bag, hopped in his car, and made the two-hour long drive home.
The entire drive was an exercise in self-condemnation. Though he hated running away, it was even more frustrating that his problem hung overhead like a dark cloud. No matter where he went, it would still be with him. He wanted to shout and punch the steering wheel. On the verge of swearing at every driver who was going too slow or too fast for his liking, Jake clenched his jaw and managed to refrain from causing an accident.
Jake hadn’t slept well ever since he and Vanessa went their separate ways. With a mind full of unpleasant thoughts, he stayed awake most nights tossing and turning. One decent night of rest was exactly what he needed to put his head back on straight. Hopefully being so far away from campus would provide that. He would take Vanessa’s advice and make an appointment with a sex therapist in the morning; but for now, he needed to stop thinking and remember how to relax.
His car pulled into the garage, and Jake looked around curiously. His stepmother’s car was in its usual place, but his father’s parking place was vacant. At six in the afternoon, it was likely Peter was still at the office. That worked out better anyway. Jake wasn’t quite ready to see his father and have a manly discussion about the reason for his sudden visit. An extra hour or two would help him think of something.
Delaying an embarrassing conversation with his father should’ve helped Jake feel more at ease, but it had the opposite effect. Being alone with his stepmother always made him feel slightly uncomfortable. Though she was friendly enough and they got on incredibly well for an eleven-year age difference, Jake always had the tendency of staring a little longer than he knew he should. Chelsea was gorgeous after all which didn’t help the matter. He would’ve been happy calling her by name just like his father, but referring to her only as ‘mom’ made it easier for him to remember that the thirty-six year old was already taken.
When Jake walked into the living room, he stopped in his tracks at the sight of Chelsea in the center of the room on her yoga mat. Maybe it was just the outfit, but she looked even more incredible than the last time he’d seen her. The tight, black yoga pants showed every curve of her toned legs, and the sports bra fit her medium sized breasts to perfection. Her exposed stomach glistened with drops of sweat in the sunlight pouring in from the window, and her long, blonde ponytail draped lazily down her back as if completing some majestic yoga pose.
From downward dog, Chelsea gave a start when she saw that someone else was in the house, but her alarm turned into a smile when she recognized the stranger to be her son.
“Jake,” she said happily. “I wasn’t expecting you. Are you just dropping by or can you stay a while?”
“I came for the weekend,” he said realizing it would’ve been polite to at least give her a call while still on the road. “I know I should’ve called, but it was a spur of the moment thing. I hope that’s alright.”
Chelsea got up and crossed the room wrapping her son in her arms and pulling him close. “You’re always welcome anytime,” she told him. “And besides, there’s nothing planned for this weekend which makes you being here even better.”
Jake could feel her warm sweat moistening the front of his shirt. It made him want their hug to last longer, but instead he broke it off early. There was a familiar stirring in the front of his pants, and he thought it best to get some distance before Chelsea felt it too.
“Is my dad still at work?” He asked.
Chelsea shook her head with an instant cold shoulder. “He’s away on a business trip for the month. At least that’s what he told me.”
Trouble in paradise? Jake wondered. She looked uneasy about it. If problems really were on the horizon, he didn’t want to pry. After all, Jake’s own relationship drama made him very aware of how important it was keeping some things to himself. “Then it’s just you and me?”
“Just you and me,” she confirmed instantly letting the cold shoulder melt away. “I’m kind of gross from earlier. I’ll grab a quick shower and be right back. Are you alright taking care of dinner?”
Jake looked at her incredulously. “You actually trust me to cook.”
“Not a chance. The takeout menus are next to the fridge. Just pick something that goes with wine. I want a drink.”
Jake watched as his mother climbed the stairs to her bedroom. Each step accentuated the shape of her body, and Jake tried not to notice only to find himself staring. Letting his eyes follow her figure until it disappeared out of sight, he shook himself out of the moment. Yoga pants or not, it was still his mother. That was reason enough to not stare in the future. Jake went into the kitchen to distract himself.
Chelsea loved her wines. She had a small wine rack that was always fully stocked. Just like her sister who preferred rich flavors over sweetness, she drank mostly reds and could rarely stomach a white. Chardonnays and Rieslings made Chelsea feel like she was drinking pure sugar water. That’s why they and ones like it had no place in her home. Knowing all the bottles would be delicious, Jake scanned the labels before choosing one at random. Any red would pair well with Italian, and he found a takeout menu to match. The food was delivered and dished onto plates by the time Chelsea came back downstairs.
The sight of her left Jake making a swift adjustment to his pants from behind the kitchen counter. She was wearing a black, silk robe that barely reached past her ass and a small pair of shorts and bra underneath. His mother had always made it a point to be comfortable in her own home, and entertaining family was never a reason to break with tradition.
“Your wine,” Jake said as he held out the glass.
Chelsea grabbed it eagerly and took a sip. She closed her eyes as the flavors coated her tongue. Turning her attention back to Jake, she grinned and gave a nod of approval.
Dinner with Chelsea was exactly what Jake needed. He found himself laughing and drinking to his heart’s content with an old friend rather than a parental figure. They made quite the pair which had always been an unusual but delightful case.
When they took their wine glasses to the couch and Jake finally heard his mother ask the reason behind his unexpected but very enjoyable visit, he was already past the point of being comfortably tipsy to give her an honest answer. She listened intently and did her best to keep their glasses full. By the time Jake told her about his plan to search for a sex therapist in the morning, she was deep in thought.
“Are you alright?” He asked. “I’m the one having the crises, but you look like you’re right in the middle of one of your own.”
“It’s just a dilemma,” she responded after a moment. The woman took a breath as if committing to her resolve before continuing. “I wasn’t planning on saying anything, but I feel like I should be honest with you too. Your father’s getaway is more than just a business trip. He’s been having an affair for a few months now. He accidentally butt dialed me while his secretary was giving him a blow job. How cliché is that!”
The mood was quickly turning sober. Sensing this, Chelsea put the smile back on her face to show that everything was alright. “Our marriage has been over for some time, and I want you to know that because of what I’m about to suggest. There’s no need to see a therapist when there’s a much better solution. All you need is practice and to work with someone patient. We can get you past this hurdle together.”
Jake didn’t know what to say. He was attracted to Chelsea more than he cared to admit, but the idea of actually fucking her was something that was never even considered. There was an invisible line. He could look but never touch. Even now, his eyes devoured every inch of her with each sweeping glance, but could those feeling be acted on?
“I’m kind of drunk,” he admitted. “But it sounded like you offered to help me last longer.”
“I did,” she told him. “There’s no need to shell out huge amounts on sex toys when the real thing will work far better. Jake, I love you like you’re my own flesh and blood, and I know this is something we can fix together. What do you say? Can we give this a chance?”
There was determination in her eyes, and Jake knew his mother well enough to recognize when her mind was fixed on an idea. What she was offering made sense. Instead of countless trial and errors mixed with talking to a shrink for who knows how long, he could actively work to correct the problem himself. He gave her a nod and witnessed a spark enter her eyes.
“What exactly do I have to do?”
“Nothing at first,” she told him. “But this won’t be a quick fix, so you’ll need to spend your weekends here for the rest of the month if you can manage it.”
Jake thought for a moment and took a sip of wine. Vanessa was the primary reason he stayed on campus most of the time. Now that she was out of the picture, it would be easier having more time away.
“I’ll be here,” he promised.
“Then let’s get started,” she said taking the wine glass out of his hand and setting it aside. “I’m going to do what I can to make you cum. Between what you feel and hear, I imagine you won’t last long. That’s completely expected, so don’t get discouraged. This is just day one.” He gave her a nod and felt his cock jump to attention as Chelsea straddled his lap and gave him a long, passionate kiss. “And I want you to call me mommy,” she whispered in his ear.
“Mommy?” He asked taken a little by surprise.
“That’s the one condition. Agreed?”
He nodded amusedly. His cock jerked under her weight, and Chelsea grinned as she felt it. She rubbed her shorts against the bulge grinding back and forth in a slow rhythm of her own making.
“Close your eyes,” she told him and watched her son do as instructed.
She rocked back and forth a couple more times before sliding onto her knees in front of him on the carpet. Unbuttoning his jeans in one motion, Chelsea pulled down his boxers until his full arousal stood erect in front of her.
“Do you want mommy to make you feel good?” She breathed so that Jake could feel the warmth of her breath on his shaft.
“Yes,” he groaned.
“Then tell me,” she commented while blowing more air on him.
“I want you to make me feel good, mommy.”
This was all the encouragement Chelsea needed “Tell mommy what’s your favorite part of her,” she said sending a fresh wave of heat to his cock and letting her hands explore their way up his thighs. “Do you like mommy’s breasts, or is her ass your favorite?”
“I love your ass,” he confessed.
Her nails went under Jake’s shirt and gently scratched their way down his chest. “Would you like to put your big cock inside of mommy’s ass?” If I let you, you’ll have to fuck it good enough to make me cum. Can you do that for mommy?”
“I’ll do my best to make you cum.”
“Mmmm, that’s what I wanted to hear.” She reached out a hand and gently wrapped it around Jake’s pulsing member. It was hard and thick. Chelsea knew he didn’t have long. “My boy is so big,” she said giving it a slight squeeze. “Just look what mommy’s hand does to you. I bet you can imagine how good it will be feeling this inside of me.”
Without waiting for a response, she dipped her other hand between her legs and instructed Jake to open his mouth. Her fingers went past his lips, and Jake recognized the taste instantly. It was more than he could take. With her juices in his mouth and Chelsea’s hand on his cock, Jake sucked on the fingers and groaned as he reached climax.
“That’s my boy,” she praised him. “Cum for me, baby. Don’t stop until you’ve given me everything you’ve got.” His cum flew through the air landing on himself, the couch, and her hand. “Next time you’ll have to cum in mommy’s pussy and fill her all up. And if you’re lucky, I’ll let you cum in my ass too.”
Completely drained, Jake laid there feeling Chelsea’s hand softly moving up and down on his spent member. He opened his eyes to see her smiling. A stream of cum had found its way onto her black robe, and she wore it proudly appreciating its affect.
“That was good for the first time, she encouraged him while taking a napkin and cleaning up. We’ll keep working at it until this is all part of your everyday routine.” She glanced at the clock and let out a yaw. “Time for bed, I think.”
She reached out her hand waiting for Jake to take it.
“What are you doing?” He asked. “Is there more tonight?”
“Just because you’ve already come doesn’t mean there isn’t work to be done. It’s pretty clear being close to a woman is still a struggle for you. That’s one of the things we need to fix.”
Jake took her hand and was escorted upstairs to the master bedroom. He watched as she untied the robe before tossing it aside along with her shorts and bra. Standing confident in her nakedness, she climbed into bed.
“I’m not spending the entire night rubbing up against a pair of jeans,” she commented. “Take them off.”
Jake did as instructed and followed suit with his boxers and shirt. Standing naked before her, he watched as she smiled with admiration before beckoning him over.
“I know you want to feel my pussy,” she said. “But right now, you’re going to taste it. Use your mouth and show your mother how good you can make her feel.”
Jake did as he was told and buried his face in the shaved wonder. It was sweeter than any he had tried before. If Chelsea had been on a diet of pineapple, rose water, and honey, she would’ve tasted just as divine.
“Oh yes, baby. Lick my pussy all over.”
Her hips moved around thrusting her pelvis against his mouth. His tongue was forced to reach deeper, and Jake loved it. He sucked and licked letting his hands explore her soft skin and squeeze her thighs. Slowly but surely her breathing began to shallow. Chelsea’s pussy moved twice as fast rubbing against her son’s lips as it went. The moment was coming. Digging her heels into his back and holding his head in her hands, she held her breath and let the orgasm take her.
“You’re making mommy come,” she shouted while trembling. Jake’s eyes flew wide open as a current of liquid entered his mouth. “Swallow, baby. Don’t stop. Just swallow my present for you.”
With his head held tight, Jake had no other choice. It poured into his mouth, and he swallowed as quickly as he could. The taste was intoxicating. He was still lapping for more when her body had finished. Fully erect and needing to feel her with newfound urgency, he dipped his fingers inside of her spent pussy and coated the wetness up and down his cock.
“No hands, baby,” she said taking a moment to steady herself. “Save using your hand for when you’re alone. We’re here to get you used to a real person.” Turning her back to him, she laid on her side and guided his cock between her thighs.
“Let’s see how long you can last on the outside.”
“I can feel you, Chelsea,” he said moving gently against her moist surface.
“Mommy,” she corrected with an insistence that Jake knew not to question.
“I can feel your pussy dripping onto me. It’s incredible.”
“It’s all for you,” she told him. “I want my baby to know what he does to me.” She felt him picking up the pace as his hands held her waist. “Yes, baby,” she urged. “Grind against mommy until you can’t take it anymore.”
“I’m going to cum,” he muttered.
“Cum for mommy. Cum all over my pussy and make it even wetter.”
He held tight and thrust forward shooting screams of cum onto Chelsea’s thighs. As the second orgasm that night took him, Jake locked his mouth onto his mother’s shoulder and tasted the salty sweat from her body. Finally spent, he laid back on the pillow.
“Time to sleep,” she said turning off the light. Chelsea gave her son a kiss on the cheek and nestled on his bare chest. With fresh cum running down the side of her pussy, she smiled contented and closed her eyes to rest.
In the middle of the night, Jake awoke to the feel of Chelsea’s gentle rocking. With his cock back between her thighs, she moved back and forth slowly and controlled. The tip of her fingers pressed his shaft gently against her bare pussy rubbing the head along her clit. She didn’t say a word and kept at a steady pace.
“That feels so good,” Jake said watching his mother’s back arch with each motion.
“I know, baby,” she whispered. “It feels good for me too.”
She reached her free hand around and placed it on the back of his neck. Savoring the moment, their bodies moved in silence while the only sound in the room was the slick wetness of Chelsea’s pussy sliding against her son’s cock.
“I’m going to cum,” he announced as the pressure inside was about to peak.
‘That’s it,” Chelsea said using her fingers to stimulate his throbbing member and forcing it harder on her clit. “I’m so glad I can make my baby feel so good.”
With a loud moan, Jake felt the hot liquid shoot out across Chelsea’s thighs. Her finger redirected the head and sent a second stream directly onto her moist pussy. The third and fourth shots found their target, and she bit her bottom lip and arched her back enjoying the warmth. Limp and trickling out the last remnants, Jake was used up and slid loose at last.
“You did good, baby,” she said before cleaning a cum-soaked finger with her mouth. “And you taste good too.”
Added: Frivolitus
