Chapter 18

Things for Tommy and his girls progressed – the three girls kept Tommy busy, to be sure, but at least he didn’t have to sneak around anymore. And he treated each of them like they were his only girl so no one had any complaints.

Carol had found a real man who could keep her totally satisfied, one she could always count on to be there and who wouldn’t run off after the first skirt that came along. His two sisters got plenty of loving from their older brother as well – Diane had found a man she could trust and really open up to, becoming the slut she’d always wanted to be. And Jenny’s lifelong crush on her brother was finally realized and appreciated.

Tommy, in return, got unlimited access to three hot, sexy, women who would do anything he asked of them. His mother had the experience to know how to please him in every way, Diane was close to his own age so he could relate to her easily as well as being fairly new and inexperienced so she could be molded.

Jenny was a complete virgin when he first took her so she was still very tight and very new to this – she too could be easily molded to be just what he wanted in her. In addition, Jenny had a terrible crush on her brother so she was his to command.

Yes, Tommy had the perfect “harem” and what’s more, he didn’t have to worry about them leaving him – they were family and so they would always be there when he wanted to use them.

Sometimes Tommy would use them one-on-one, choosing his girl for the night and devoting himself entirely to her. Sometimes he would double up and use two of them to satisfy his needs. And sometimes he would gather all three together for some group fun.

At first, Tommy was satisfied with getting blowjobs and straight sex – after all two of his girls knew next to nothing about sex and his mother had gone without for so long. Plus he wasn’t sure what she knew anyway.

They all said they would do whatever he wanted but he didn’t know how much of that was just talk and how much they meant! So he took it slow with them at first. But one day that all changed – at least for two of them!

It was Carol’s night with Tommy that night and after he had given her his usual pound-her-till-she-can’t-breathe fucking, she was laying on the bed on her side with Tommy behind her spooning with her as she recovered.

While Carol had cum twice, once from his oral skills and once from fucking her, he had yet to get his release. Now with his aching cock nestled up against her backside, he was gently pushing it up against her asscrack, enjoying the feeling of dry fucking her between her legs.

Her thighs were soaked from her juices, and it felt good to rub his hard cock between her legs. Every so often his small thrusts would result in him slipping just a bit into her wet, inviting pussy, eliciting a soft moan from her.

Her moans encouraged him and he reached around her hip to begin rubbing her saturated pussy – not entering her, she might still be too sensitive, but rubbing her pussy lips and toying with her clit. His aim was to keep her sexually aroused and steaming while she came back so he wouldn’t have to rewarm her to finish what he needed.

But Carol was about to throw a twist in his plans.

“Mmmm, baby your cock feels soo nice back there. And your playing with my pussy is getting me horny all over again!” she said.

He leaned forward to kiss her neck “That’s the idea, beauty ... I want you to always want me!”

Carol sighed. “Tommy honey can I ask something?” she said.

“What is it? What do you want beauty?”

“Would you ... um ... fuck me ... back there?” she said hesitantly.

“What?” he said not sure he heard her right.

Carol turned over to face him. “I want you to fuck me ... in my ass. You’ve taken my pussy many times and I’ve given you several blow jobs. But you still have one hole you haven’t claimed. I want to give you all of me, Tommy. I want to belong to you completely,” she explained.

“So you want me to take your ass too – you want to be my three-hole slut, is that what you are saying?” he asked.

“Yes, Tommy ... more than anything. I need this sweetheart – if you don’t take all of me, I will always feel that maybe you might find someone else who will. I want to be everything you want and everything you need,” she said, looking him straight in the eyes.

Tommy could see she was serious. This was important to her and so it was important to him as well.

Tommy got up on his knees on the bed. “Get on your hands and knees,” he said. Carol looked at him with a smile and instantly moved into position. Tommy pushed her chest and head down on the bed and she grabbed the pillow to hold on to.

“Now remember, I am bigger than most guys you’ve had including him – are you sure about this?” he asked.

“Yes, Tommy ... I’ve never been more sure of anything in my life. I want to be everything and anything to you. Please,” she said.

This wasn’t a mother talking to her son. Carol’s words and the emotions behind them spoke of a woman wanting to please her man, her lover, no matter what he may ask of her. She was devoted to him totally – far more than just a mother-son relationship.

Carol was falling in love with her son. She may have given birth to Tommy all those years ago, but now he was returning the favor and giving birth to her ... by turning her from just a common housewife and mother to the woman she’d always wanted to be. Loved. Appreciated. Desired.

“Okay, now I know it’s been a long time since anyone has done this to you so we will start off slowly. I am going to use my fingers to get you used to having something in your ass before we move up to my cock,” he said.

“Thank you, Sir, for taking it slowly with me. You are right, it has been a very long time,” she said.

Tommy opened the nightstand drawer next to her bed and got out the tube of lube she kept there for those times when she used her vibrator – or rather when she used to use it. Since Tommy began regularly fucking her, that old vibe had taken a back seat and now it was only taken out when he wanted her to use it on herself for a masturbatory show or to tease and torment her with the device.

“All right slut spread those cheeks for me and let’s get you all greased up!” he said.

She looked back at him, biting her lip in eager, yet nervous excitement. She obeyed him, however, trusting that he knew what he was doing. She spread her ass cheeks wide and held them there giving her son a lewd view of her most private areas. Before now she would never have dreamed of putting herself on display like this to any man, much less her own son. Tommy smiled arrogantly, knowing she was his to command.

Carol was kneeling in such a way, with her ass high in the air and her legs spread wide holding her asscheeks apart, that Tommy knew she must feel very exposed and even vulnerable like this. He leaned forward a bit and gave his mother’s asshole a long slow lick, making sure to get her as wet as he could. then he blew softly on the wet spot making her gasp in surprise, then moan in utter ecstasy.

He moved a bit closer to her upturned ass and began by softly stroking her asscheeks using just his fingertips, lightly, almost imperceptibly, as he tickled her ass. Slowly, Tommy let his fingers move over her, exploring every little inch of her bare ass. His slow, sweeping motions gradually got tighter and more focused as he neared her anus.

Little by little, he allowed his fingers to move further in, getting closer and closer to her spread crack. He ran his fingers up and down the crack smiling as she mewled her pleasure and pushed back at him. Yes, she wanted this. She wanted to be penetrated.

As Tommy explored this never before seen part of his mother, his cock hardened. Tommy wanted this just as much as she did. He wanted to penetrate her just as much as she wanted him to.

Tommy continued to move his fingers up and down between her cheeks, teasing her, enjoying the softness of her skin and the shivers his touch gave her. Occasionally she whimpered softly when his fingers lightly grazed her tight hole. He played with her, toying and teasing her ass, lightly tickling her anus.

He didn’t apply any pressure at first, he just wanted her to ache for him ... he wanted her to reach the point her need for this would make her rosebud open for him. He tickled and teased her, delighting in every soft moan, every tiny, jerking little thrust of her ass.

She pushed back against the tormenting hand, trying to get him inside her. She lifted her ass higher hoping that would encourage him to enter her. She moaned and whimpered and cried for him. Anything ... she just needed him inside her.

It was time to move to the next step. “Okay, slut, this might be a little cold at first, but it will warm up quickly,” he said, taking the bottle of lube in hand. He squirted a large glob of the jelled substance on her anus and Carol reacted.

“Oh! That’s cold!” she cried. But as Tommy promised, once he started working it around, it warmed to her skin and she relaxed again.

Tommy rubbed some of the lube on his index finger before he began rubbing it across her anus, massaging the tight little hole and getting it to relax to his touch. It wasn’t polite to just walk into someone’s house. So he was knocking on her door, hoping to be invited inside.

She came to the door all right ... he could feel her sphincter relax a bit and he heard her softly moaning as he played with her sensitive asshole. But when he tried to gently push into the hole just a bit, he felt her clench up tight. He felt her resistance.

She wasn’t ready quite yet. Even though both of them wanted this to happen, they would have to work at it together. She would have to trust him, to relax, and open up to him. He would have to convince her to do that.

Tommy backed off a bit and instead of trying to push into her, changed tactics and started rubbing her anus. He rubbed it gently but firmly – he wanted her to know he was back there and that he wanted in, but he would wait for her.

He massaged her anus for a couple of minutes as she slowly relaxed and calmed herself. At last, he felt her becoming more pliant, more accepting and he pushed his fingertip against her lubed star and felt her tightness yield a bit.

Carol moaned softly as her ass opened to swallow his finger. Tommy’s fingertip disappeared inside his mother’s ass and he felt it slip past her sphincter – he was in! Now past the ring of muscle that had proved such a barrier, his finger slid easily and in a single slow stroke, he sunk into her, as deep as he could go.

“Ohhh God, Tommy!” she gasped, clutching her pillow tightly. He pushed into her until he could go no deeper and then stopped, letting her rest and get used to having something in her ass again.

Once he felt her asshole loosen its grip a little, he started to pull back out again slowly. But he didn’t pull completely out – he stopped when he got to the last knuckle, then he pushed back in.

He repeated this slow in and out routine over and over, each time moving a little faster until finally, he set up a steady, gentle rhythm, finger fucking her ass while she moaned and humped back at his finger with each forward thrust.

“Oh God, Tommy ... Oh, yes ... Ohhh...” Carol moaned as he fingered his mother’s ass. Waves of delicious, decadent pleasure washed over her again and again and Carol pushed back with each one, letting him know she was completely enraptured with this shameful, depraved act.