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.