Janet felt her stepson's thick cock snuggling against her backside as she awoke in the middle of the night. As is sometimes the case, she fought to get back to sleep, unsuccessfully. Her brain was flooded with thoughts as she tried to dismiss the guilt that seemed to be creeping under the covers. Since arriving at this pristine, tropical location, much had transpired. What started as innocent flirting progressed to fondling, groping, oral sex, copulation, and finally–anal sex.

"How did things ever get to this point? My god, I couldn't have dreamed this scenario a month ago, and now I'm lying in bed with my stepson's semi-rigid cock pressed against my ass. I was a normal housewife, a member of a book club, and a volunteer at the soup kitchen. Now, I'm a slut who can't wait for my son to put his penis inside me."

Thomas groaned and shifted so that his cock was now begging permission to slip back inside her moist channel. In a reversal of sorts, her asshole was now a bit tender but her pussy seemed fine. Almost out of habit, she reached behind her and opened her legs enough so she could guide the plum-sized head into her cunt. The response was immediate. Suddenly, Thomas's thick member was sliding back and forth and she felt his hands reach around and squeeze her huge breasts.

"Jesus, is he even awake? I think he's fucking me in his sleep. Sleep-fucking. There's a new term for Dr. Phil."

But Thomas wasn't asleep. He had been awake for some time and when he felt his stepmother's fingers around his shaft, he took full advantage of it. Once his cockhead had parted her moist labia, he wasted no time burying himself deeply in that fleshy pleasure palace. He was addicted to the feeling of his thick cock encased in her welcoming pussy.

Janet didn't mind. In fact, she loved it as long as he didn't get too rambunctious. Sleeping with a nineteen-year-old sex machine had its perks. She only needed a break once in a while to avoid being crippled.

After a lengthy period of slow fucking, he slipped out and tried to reinsert himself into her recently explored ass, but she blocked him and put him back in her pussy.

"That portal is closed for the time being, Honey. Do you want to cum in my mouth instead?" She knew he loved to watch her suck him with her full lips. It helped that she loved the taste and the feeling of sperm filling her mouth.

However, it was already too late. Thomas's balls needed to empty themselves, and there was no holding that tide. As his cock head reached the deepest recesses of her pussy, he let loose. It was like the pressure being released from a kinked hose. He grunted and pressed his hips into his mother while his penis throbbed and shot a thick stream of ejaculation into the deep recesses of her cunt. Several large spurts followed as Thomas closed his eyes and moaned with relief.

Janet smiled to herself.

ˆMy god, that boy can cum. His balls must be working overtime to keep up."

In seconds, he was snoring with his cock still inside his stepmother and his hands on her breasts.

"So much for whispering sweet nothings in my ear," Janet thought. "I hope I can get back to sleep that easily."

She adjusted her hips and felt his softened cock slowly slide out of her. In a few minutes, she was sound asleep as cum began to seep out of her.

The next day they busily prepared for their dinner guests. Food preparation was one thing, but they tried to eliminate any telltale clues of their true relationship. Thomas hadn't slept in his bed for a week or so and had moved his belongings into his mother's bedroom. He somewhat guiltily examined the chair and the couch for obvious cum stains. Their furniture had often been used as a bed.

Just before sunset, they saw the couple coming down the beach dressed in tropical garb. Arthur was wearing shorts and a Hawaiian shirt. Kate had a bikini top but her lower half was covered in a floral wrap. Her breasts were nowhere near as large as Janet's, but they jiggled nicely as they walked up to the bungalow. Both were barefoot. They each carried a bottle of wine.

After the welcomes, drinks were served, starting with a Mai Tai and accompanying hors d' oeuvres. They chatted and filled in each other with details about their lives when not on vacation. Thomas seemed interested in the tech industry and Arthur had lots of advice. Janet and Kate got along and found they had many common interests. Janet also could see that Kate couldn't take her eyes off Thomas as he listened to her husband.

Thomas was wearing shorts and a shirt, like Arthur. But his shirt was unbuttoned and his tanned chest and abs looked like a weightlifter's as he lounged in his wicker chair.

Dinner included more drinks and by the time they were done, both bottles of wine were gone. Kate had her share and got a little tipsy, but her husband refilled his glass repeatedly, and by the time they were ready to leave, he was slurring his words and drunk.

After profuse thanks for the evening, the couples hugged goodbyes. Arthur hung onto Janet for an uncomfortable length of time and actually tried to kiss her. She turned her head so that his lips landed on her cheek instead of her lips. Kate looked pissed, and Thomas thought she pressed herself into him a little too obviously in response. Then she followed with a quick kiss to Thomas and Janet on their lips.

As Kate and Arthur headed out the door into the darkness of the night, Arthur stumbled and fell flat on his face. Fortunately, he fell in the soft sand. Janet immediately went to his aid and asked if he was okay. Arthur slowly rose with her help and dusted himself off, but Janet was concerned.

"Thomas, you should walk Janet and Arthur back down the beach. Grab a flashlight so they can see."

Despite their protests, the couple finally agreed, and, flashlight in hand, the three of them headed off. Soon Kate grabbed Thomases proffered arm as Arthur stumbled behind them. Thomas felt her tight grip press his muscular bicep into her breast and naughty thoughts entered his nineteen-year-old brain. As they continued on the half-mile or so walk, Kate confided that Arthur was an alcoholic and that this was not unusual for him.

"He can be such an asshole when he's drunk. He can get mean, too." She spoke normally as if she could care less if he overheard her, but Arthur was too drunk to understand what she was saying. He tried to stay on his feet and keep up as he stumbled behind them.

When they finally reached their cottage, Kate directed her husband to the bedroom with Thomas's help. Arthur fell onto the bed and in seconds was out. Thomas and Kate removed his shoes and Kate asked Thomas to help her remove his shorts. After a struggle, they had him in bed in his skivvies but still wearing his shirt.

"I can't thank you enough. I'm not sure where I'll sleep tonight, he's a thrasher. I can't thank you enough. I wish I knew how to repay you."  

"No worries, Kate. I'm happy to help."

As they stood in the living room, Kate wrapped her arms around Thomas in a hug, and he awkwardly set down the flashlight to reciprocate. She stood on her tiptoes and kissed him. But this was no peck. Her mouth opened and her tongue found his. At the same time, tears began flowing from her eyes.

"Are you okay, Kate? What's wrong?"

"I'm sorry. You don't need to hear my problems. You need to get back to your stepmom."

"No, I'm fine. How can I help? Here, sit down. I insist."

Thomas genuinely wanted to help if possible, but he was also excited by the kiss he had just received. Strange lips were always a turn-on, and Kate was an attractive scantily-dressed forty-something woman in his arms.

As she tearfully related the emotional abuse she typically endured after nights like this, her story tugged at Thomas's heartstrings. He held her in his arms and caressed her, brushing her hair away from her face. Suddenly, their lips were together and they were kissing passionately.

Thomas automatically moved his hand to her breasts and then slid his fingers under her top to find a swollen nipple. He was so used to wasting no time in foreplay with his mother that he gave no thought to a slow seduction. And Kate was offering no resistance.

"Go ahead and untie my top. I need this so badly," she breathed into his ear.  

With her free hand, she loosened the knot on the wrap covering her lower torso and as Thomas's hand drifted to her exposed thighs, he realized that she was not wearing any panties. His hand found a trimmed covering of soft hair, and as he touched her there, she opened her legs. He felt her breath quicken and her hand went to his lap.

The same fingers that had untied her wrap now found the button holding his shorts. She deftly unfastened it and opened the zipper. Her hand reached inside and she gasped.

"Oh, my lord! What is this?"

She stopped kissing and stared at her hand as it struggled to release the hidden appendage in her grip. Thomas lifted his hips and quickly slid off his shorts. As usual, he was wearing no underwear, and just like that, Kate realized she was holding the largest cock she had ever laid eyes on.

"My god. You are so thick. I thought you would be large but 'careful what you wish for,' I'm unsure what to do with this."

She slowly stroked him, her fingers unable to touch her thumb. She leaned closer, examining him like a rare museum piece.

"Your cock is beautiful. Arthur's is so much smaller. But he just screws me and pleases himself. Oh, Honey. This is amazing, but it's also a bit scary."

She bent further and now her nose was almost touching the crown. Thomas's tanned thighs contrasted with the ivory shaft in her hand, and after first kissing the tip, she opened her mouth and stretched her lips over the head. As much as she tried, she could get little more than the crown inside her mouth, but even so, her tongue and lips sent ecstatic waves of pleasure into Thomas's cortex.

Here was a beautiful woman he barely knew naked and sucking on his cock. He watched in fascination and studied the scene. Kate was not only attractive with her flaming red hair and green eyes, but her pale skin was a study in contrast to his dark tan. Her breasts bounced on his thighs with her efforts, and he reached down and squeezed them. They were more than a handful, but half the size of his mother's. Still, they had a nice shape and retained a perkiness that most women only wished they had.

After several minutes, she removed her mouth and inhaled a large breath. She leaned back on the couch and looked at Thomas with pleading eyes.

"Be gentle, but I need you to fuck me with this monster. I haven't been properly fucked in ages. Will you do that for me?"

Thomas only nodded. He positioned himself between her legs and first kissed her lips and then briefly kissed and licked her pussy. When he was convinced she was wet enough, he grabbed his cock in one hand and aimed the fat head at her tiny portal. It beckoned him: slightly open in a patch of downy red hair. He rubbed the glans up and down her slit while Kate craned her neck to watch. At first, the discrepancy between the size of his purple cock head and her tiny, pink sweet spot seemed like an impossible match. But gradually with some extra saliva and Kate using her hands to spread her wrinkled labia, Thomas achieved a partial entrance. Kate had a look of panic on her face but encouraged him to continue.

Thomas slowly pushed and gained an inch or so, and then he stopped and looked at the redhead as if to ask if she wanted more. Kate only nodded affirmation and reached down to stroke the still-visible portion of his shaft and help insert it into her cunt. Gradually after a couple of half strokes, Thomas was completely in.

Kate's eyes fluttered and rolled upward until the pupils had practically disappeared into her head.

"Oh. My. God. Gently, please. Let me catch my breath, Thomas."

She looked down and couldn't believe the entire log was buried in her. A mixture of pain and pleasure coursed through her. She gently pushed on Thomas's rock-hard stomach, and in response, he slowly pulled nearly out. He then began slow, steady strokes in and out. Kate's inner labia clung to his shaft like a surgeon's glove. As he fucked her she made little whimpering sounds but reassured him with a nod of her head that she was fine.

Thomas considered what might happen if Arthur woke up and stumbled upon them this way, but his worries were nowhere near enough to make him stop. Kate's perky breasts jiggled with his hip movements and he reached up and played with her large nipples.

Gradually and together, they increased the tempo as Kate began meeting him thrust for thrust. Thomas bent down to kiss her breasts and she wrapped her arms around his neck in the process.

"Don't pull out, but spin around so you are sitting with me on your lap. Yes, like that. Let me feel you this way. Go ahead and suck on my boobs if you want. Mmmm. This feels wonderful now that I'm finally used to your size. God, you have the biggest cock I've ever seen. I can't believe it fits in me. If you have to cum, go ahead. I can't get pregnant. Mmmm. Oh, yeah. I'm close, Thomas. Keep fucking me just like that."

Kate was bouncing up and down, slamming her ass onto Thomas's lap and he knew he was about to blow. He reached around and rubbed some of their combined juices onto his index finger and then rubbed it on her anus. She gasped, quickened her pace briefly, and then suddenly stopped and squeezed Thomas with all her strength. As her pussy muscles began a series of contractions, he inserted his finger into her anus and worked it in and out. He could feel his finger on his cock from the other side of her perineum, and that was it. Sperm shot out of his cock into her moist cunt.

Kate pressed her lips to his and let out a guttural moan as her climax erased all thoughts from her brain. She ground her hips back and forth, keeping Thomas firmly seated inside her. When her ass finally stopped twerking, he waited for a couple of minutes and then slowly lifted her enough so that his cock could slip out. Once freed from her cunt, it plopped down heavily between his meaty thighs .

"I've never been fucked like that in my entire life. That was incredible. I'm sorry we're leaving soon but you've given me something to remember. I hope I'm able to walk tomorrow, but if not, I earned that lounger. Thank you, Thomas."

"That was wonderful for me, too, Kate. I'm sorry about Arthur. Are you going to be okay?"

"I'll be fine. He'll wake up with a royal hangover and won't remember most of the night. But I'll remember it. I know you have to go. Your stepmother is probably worried about you. But if you ever come to Silicon Valley, I can show you a good time."

She kissed him after they both dressed. Thomas grabbed his flashlight, waved goodbye, and returned to his bungalow. Janet had cleaned the kitchen and gave him a knowing smile when he walked in.

"That took a while. Everything okay?"

"Yeah. Arthur had some issues so I helped out, and then we talked for a while. Kate is not in a happy marriage. She's very sweet."  

Thomas didn't lie to Janet, but he didn't have to volunteer the whole story.

"I bet she is. I'm going to bed. You coming?"

Thomas wanted to say, "No. I just came." But instead, he said he would follow her soon. He kissed her goodnight and climbed into bed once he heard her softly snoring. He could still smell Kate and see her on his lap, her beautiful red hair bouncing along with her breasts.

"I wonder if Janet knows? Probably not." He soon fell asleep, smiling.