6 Times a Day

Alan was totally mentally and physically wiped out, but the night didn’t end for him when he went upstairs. He lay down in his bed naked, prepared to fall asleep, but he’d forgotten about his mother’s favorite new nightly ‘kiss and tuck-in’ tradition.

So a few minutes later, Susan came in to give him a goodnight kiss. She’d put on yet another new semi-transparent nightgown just to stimulate him.

Despite his exhaustion, he couldn’t help but love that sight. “Hey, Mom. What’s up? You look great!”

“Thank you.” She smiled nervously. Then she slowly pulled her nightie down until her chest was completely bared. That, plus the fact she was wearing high heels, showed she meant business. .𝙘𝙤𝙢

In addition to wanting to have a little fun, she needed reassurance that Alan didn’t like Brenda in any way more than her. She was mostly worried about her “merely” G-size boobs.

“I’ll bet you really like Brenda’s super large hooters,” she said in a melancholy tone. “But how do they compare with Mommy’s?” She tried gamely to arch her back, thrusting her big, bare tits forward and up alluringly.

Alan was dead tired and not really in a mood to play around, even though his dick was stirring a little. He felt like he’d had more fun in the last hour or two than in his entire three middle-school years, and he was exhausted. But he understood Susan’s need for reassurance, so he tried his best. “Mom, your boobs are great. They’re my favorites.”

She smiled in shy delight and pulled back his covers. Then, without asking, she started stroking his penis, even though it wasn’t even half-hard. “Awww. You’re just saying that to be nice.”

“No, really Mom. Your tits are so fine; they’re ten different kinds of fine. Your whole body is fantastic.”

She cupped her hefty globes from below and lightly traced around her nipples. “Are you sure? I want you to be sure. It means a lot to me if you think I’m worthy of being one of your personal cocksuckers.”

“Mom, I don’t even know where to complain about that comment. First off, it’s wrong for me to even have something called a ‘personal cocksucker,’ but if I did, who could top you?”

She smiled. “Thanks. Still, Mommy will let you play with her titties just a little bit to help you make sure.”

So he groped a tit with one hand, after she bent right over him to make things easier for him. Unusually, he chose to put his other hand on her face, so in this case he fed two fingers into her mouth.

She eagerly sucked on them, treating them as a proxy penis. She wanted to reassure him that she would gladly suck him off if he wanted. She’d still been standing, and her nightie was miraculously clinging to her hips. But she sat on the edge of his bed so she’d have access to his cock and he’d have better access to her tits.

She continued to stroke his penis, which didn’t stay flaccid for long. Lingering memories of his measuring Brenda’s bare chest certainly helped him rebound quickly. She said in a tempting, teasing voice, “Uh-oh! You’ve got your busty mommy half naked and in your bed. You’re not going to touch her in that one forbidden, naughty, naughty spot, are you?” She looked knowingly at her crotch.

He gulped as he stared at her bush, and in particular at her labia, easily visible through her semi-transparent nightie. He loved how her nether lips appeared red and swollen, as if ready to be fucked.

“Good.” She sighed happily as she felt his dick fully stiffen in her hands. “Tiger-”

Seeing that she was still a bit down, he added, “Mom, I’m guessing that you’re worried about Brenda’s boobs and how big they are.”

“No, I-”

“Shush,” he said very gently. He brought his other hand down so that both hands could fondle her tits. “I understand. She’s VERY stacked, and very beautiful. But you know what? There’s such a thing as having boobs that are TOO big. I mean, what if her boobs were double their current size? Everyone would agree that would be bad. She’d barely be able to get out of bed, I imagine. As far as I’m concerned, there’s a perfect tit size, and it’s right here in my hands.”

That was kind of a lie, but kind of not. He was lying when he said he thought Brenda’s tits were too big. It was close, but especially because they were so round and high, he found them very alluring indeed. But he was telling the truth that he thought Susan’s boobs were the ideal size (and Suzanne’s, since those were just as large). He’d grown up seeing Susan and Suzanne as his ideals of female beauty, so if he thought of “perfect boobs” in his mind, he thought of theirs first.

He gave her dangling globes some loving squeezes, deeply sinking his fingers into her tit-flesh.

“Oh, Tiger! You have no idea how happy it makes me to hear you say that!” She growled huskily, “There IS a perfect size, and it’s right here in MY hands!” She moaned orgasmically as she looked down at his cock and her fingers as they slid all over it.

But then she asked shyly, “Do you really mean it?”

“Of course! Plus, they belong to you, and that’s the most important thing.”

She forgot about stroking his cock for a while as she pulled his face into her cleavage. “Son! Oh, Son! That makes me so happy! I’ll admit I got a little bit jealous. That’s petty of me, I know. Envy is a cardinal sin, after all.”

“That’s okay, Mom.” He spoke into the deep chasm between her soft yet firm melons. “I guess it’s looking like Brenda’s starting to seriously lust after me, and I lust after her too. But she’s only gonna be here once a week, for a few hours, and I’m around you pretty much 24/7, minus school on weekdays. So you have nothing to worry about with her. I barely know her, and I LOVE you and always have. She’ll never be able to compete with our love for each other.”

She considered that, then resolved to not let Brenda ever visit except for their weekly card game. Having decided that, she felt a weight lift from her shoulders. She’d been gently rubbing his cheeks with her tit-pillows, but she let go and resumed jacking him off. “You have no idea how relieved I am to hear that. I take my role as one of your personal cocksuckers very seriously. Obviously you already have others, and I know you’ll have more, and that’s your right. But I just don’t want any of them to be BETTER than me! Well, except for Suzanne, of course. I know she’s better, but that’s okay because she’s my best friend in the whole world. Besides, she’s teaching me how to catch up.”

He didn’t reply, because it seemed like the crisis had been averted. Meanwhile, he continued licking and kissing the inner slopes of her heavenly globes while she pumped and stroked, and pumped and stroked some more. He inhaled deeply. He could smell the fresh, lightly perfumed skin that she was literally pressing against his nose, and he could also smell her aroused pussy.

She asked in a very motherly tone, “So how was your day, Tiger? How did your classes go?”

He tried his best to answer, but between her jacking him off and letting him play with her tits, she was making it extremely difficult for him to concentrate. “Um, good.”

She continued to ask him the same mundane questions she’d typically asked him for years, even as she rubbed his sweet spot with two fingers while playing with his balls. “So did you do all your homework?”

“No. To be honest, I didn’t,” he somehow managed to answer despite all the distracting stimulation.

“Oh, no. Tiger’s been a bad, bad boy. He needs to be punished. No more handjob for you! Instead, Mommy’s going to have to drain your balls of all your cum so you can study better for school.”