6 Times a Day

'Someone' Special [ 3 / 20 ] 4K words

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After all the moving about, Alan's burning erection was pressing up against one of her ass cheeks. He was so aroused that he needed an even more profound and intense sexual satisfaction. He didn't think at all but just acted. With his hands still mauling her enormous boobs, he pulled his lower body away and then swung it back in, hoping to hit a hole.

His erection landed directly on her anus, and that suddenly made everything clear to him. YES! I'm going to fuck her ass! Right now! Fuck, yeah!

The urge to simply plunge in was nearly overwhelming. However, Suzanne had been trying to educate him about anal sex, and he knew that he could seriously damage his mother if he wasn't careful, especially since his cock was lacking lubrication. So he shouted, "Quick! Where's a condom?! A condom?!"

Misunderstanding, she wailed unhappily, "Oh, Son! We can't! We can't!"

"No, I don't mean that. I'm going to fuck you now, but in your ass! We need a condom for that too!"

Her heart skipped a beat. Suddenly she went from a near shout to an awed whisper. "My... my... ass?!"

It occurred to him that Suzanne had insisted that he keep condoms on him at all times, and he'd been trying his best to be prepared. That meant that he should have a condom in the pocket of his shorts. He looked around frantically for his shorts, only to feel rather silly when he realized they were still around his ankles.

He bent over, fumbled around in a pocket, and found the condom. While he was down there, he stepped out of his shorts to give his legs more freedom to maneuver.

As he frantically tore open the condom, he watched his mother's ass humping back towards him. She was so horny that she could hardly breathe, so she gasped heavily as she said, "Son, I don't know! The ass? That seems so... well, naughty!" But it was clear from the way that her ass was wildly humping the air that she was possibly even more eager than he was.

He breathed a sigh of relief when he slipped the condom on. But then it occurred to him that he still needed adequate lubrication. Shit, shit, shit! Anal sex is such a hassle. Where the hell am I... Oh, wait! I know: the olive oil! Remembering that Susan kept a bottle of olive oil near the stove at all times, he quickly found it and poured it all over his shaft.

All the while, Susan's ass was wiggling with need while her erotic "mmmm" moans grew louder and louder. She couldn't see what he was doing, and she thought he was teasing her as a show of willpower. (Needless to say, this only aroused her even more.)

Finally, he thrust his hips forward. His cockhead again prodded directly into her anus, with most of it going inside before he even realized what was happening.

The rush he felt from penetrating his mother's asshole was tremendous. He yelled, "Take this, whore mother!" and pressed deeper.

"Oh my GOD! Tiger, not the ASS! It hurts!" she screamed. Then she began wailing incoherently. Her anus had never been penetrated by anything so large. The olive oil helped, but he needed to go slower, because her anus and rectum had never been stretched that wide before and there was no natural lubrication there.

He was hit with another surge of pleasure as he realized, I'm finally fucking Mom! I am! Oh God! Oh God! Unfortunately it's her ass, not her cunt, but this is fucking!

That was so startling to him that his legs nearly gave way. It seemed like he could feel every single nerve in his body tingling at once.

His cockhead pushed all the way in, and then it kept on going. And going. And going. His cock went in a good six inches before it finally stopped.

Neither Alan nor Susan could believe that he'd gone that far that fast, not to mention that he was in her ass in the first place. He grunted as loud as he could manage, while she was screaming loud enough to alert the entire neighborhood.

Tears came to her eyes. The anal sex was so painful that she didn't know if she could take it. But she gritted her teeth and forced herself to endure. UGH! GOD! UH! Dear Lord, please! Please! Have mercy! UGH! Please Lord, I don't know if you approve of this, but... HNNNG! It just... Oh! Phew! It... it means so much to me!

Help me! Lord, help me! Help me be a good fuck for my son! I don't ask for much, but help him fuck my ass!

Slowly but surely, he pushed in deeper.

She screamed loudly and incoherently with a mixture of both pleasure and pain.

She hoped against hope that it would get better, because it was so much more painful than she'd anticipated. Without realizing it, she continued to scream loudly.

He stopped pushing deeper in response. But he was afraid to pull out, because he worried that might only hurt her more. Thus he had to maintain his position, with his erection lodged most of the way in her ass.

Slowly but surely, her screaming died away as the pain lessened. However, she continued huffing and puffing, desperately gasping for air.

In her thoughts, she turned strangely aggressive. Lord, cut me some slack here, please! You're not exactly helping. I suppose You don't approve of a son fucking his mother's ass, but what do You expect? You made us this way! You've given me a body that's built to please and serve my son. And you've given him a powerful and needy cock that demands satisfaction. Would you rather he fuck my... unmentionable?

She suddenly decided on a different approach. The Lord helps those who help themselves. I need to relax! I'm going to stop worrying about the pain. I'm going to give myself fully to being a vessel for my son's sexual pleasure. If it doesn't feel good for me, at least I'll get some pleasure knowing he's getting his pleasure. I need to focus on that great big cock of his, pumping in and out, squirting cum all over my face and tits.

Aaaah... I feel better already. Yes... Relax... Just take it easy...

He noticed that she'd rapidly gone from screaming to contented purring. So he asked, "Mom, are you okay?"

"I'm better than okay. I'm ready! Fuck me good!"

"Are you sure? I was about to pull out all the way."

"DON'T YOU DARE!" She briefly tensed up as she said that, but then forced herself to relax again. She could feel the difference in her ass as she alternated squeezing tightly and then relaxing around his shaft.

After a few more heavy breaths, she said, "Seriously, do it! Don't wait. DO IT!"

Her voice was so insistent that he resumed moving his hips. Since his boner was already embedded almost entirely within her, he pulled back out almost all the way, until he was in danger of popping completely free. Then, slowly and carefully, he pushed all the way back in. In fact, thanks to his mother's newly relaxed condition, he wound up pushing in even deeper than before.

She felt shivers run through her body as his cockhead pushed into virgin territory. It felt incredibly strange, but she couldn't deny that by this point she was feeling more pleasure than pain. That was an unexpected bonus, since she'd been willing to go through with it no matter what.

Slowly and carefully, he pulled almost all the way back out, then again pushed all the way in. His physical pleasure was immense, and the knowledge that he was fucking his mother (at least in one way) increased that even more. However, his joy was tempered by the worry that she might be suffering.

Thus he breathed a sigh of relief when he heard her familiar sexy moan. "Mmmm... Like that, Son! Mmmm... So good!"

He was slowly pulling out when he asked, "You like it?"

"I love it! I'll admit... it hurt at first, but now... MMMM! YES! Grab my tits! I'm not made of glass. Fuck me harder!"

"Really?" He started speeding up a bit as he pushed back in.

"UGH! AAAAH! DO IT!" It was clear from her voice that she was in ecstasy. Then he reached around and grabbed one of her big tits, causing her to cry out loudly again, but this time with pure joy.

In fact she was still feeling some pain, but it was swamped by so much pleasure that she didn't care. It occurred to her that the pain was somehow actually heightening the pleasure, perhaps by providing such a stark contrast.

Katherine was in her room making herself sexy for Alan when she heard the screaming. It had taken her a minute or two to get semi-presentable, but she finally ran to the kitchen to see what all the fuss was about.

She was staggered by the sight that greeted her there. Alan had one hand on his mother's boobs, four fingers of the other hand up her pussy, and his erection was pistoning in and out of his mother's asshole with very long and deep strokes.

She didn't recognize her mother at first, because of the maid's uniform and all the long hair that had fallen down over her mother's face. Her first impression was that her brother was fucking some new, and obviously extremely voluptuous, hired help.

But Susan's huge, swaying jugs quickly gave her away. Katherine knew of only four women with tits that big, and their different hair styles removed Suzanne, Xania, and Brenda from contention.

"Mom! Are you okay?" Katherine yelled over all the loud panting and moaning.

"Woooo-hoooo! Yeeeeesssss!" Susan screamed. "I'm very okay!" That certainly was true. Alan was now pumping in and out of her butt with a regular and profoundly penetrating pounding, and although there was some lingering pain, she hardly thought about it anymore.

Already forgetting her embarrassment over being discovered like this, she screamed, "I'm FANTASTIC! Tiger! You're an ANIMAL!"

Katherine just stood and stared, unblinking, at the sexy scene in front of her. Her heart pounded and her nether lips grew wet.

"Ah-Ah-Alan... Yes! YES! Alan surprised me, is all!" Susan screamed, barely able to put a short sentence together. "YEEEESSS! Fuck me, fuck me, fuck me! Yes! Tiger is fucking meeeeeeeeee!"

He continued to pound into her mercilessly. She'd only been clutching onto the edge of the counter with her hands, but his body slowly drove her forward along the counter until the front of her thighs rammed against its side. His driving erection forced her hard into it. He slammed her over and over again.

They both continued to yell and scream, although neither said very much. Alan did speak from time to time, but about all he said were things like, "I'm fucking you, Mom! Fuck you! Fuck you up the ass!"

Variations of that drove her to further screams and further heights of ecstasy. Susan tended to just say, "He's fucking me! Fucking me! Fuck me! Fuck me!" and the like, over and over.

That sounded to Alan like he was fucking her pussy, and that was the ultimate taboo and tempting sex act for him. The fact that he was really fucking her ass was great, but thinking it was her other hole drove his arousal completely off the charts.

Katherine's alarm rapidly turned to arousal. Suddenly, she had a great urge for Alan to fuck her ass, so she could be as ecstatic as Susan obviously was. I can't believe it! I'm actually watching Brother fucking Mom! True, it's the wrong hole, but it looks almost the same as doggy style. He's slamming into her, over and over and over! Oh CHRIST, that's hot! That's a sight I'm gonna see a lot from now on, I'm sure!

As she played with her pussy lips, she asked Susan, "Is it really that good, Mom?"

Susan turned her head towards her daughter and her eyes bugged out as she tried to express the strength of her emotions. "So good! So GOOD! At first I thought not, but then... OOOH! MMMM! Oh God! Mmmm, YES! Like that, Son!"

Katherine stopped asking questions, realizing she wasn't going to get coherent answers at this point.

Alan kept on steadily fucking Susan for a few more minutes. Then he began pumping his semen into her ass without warning. He let out a banshee scream as his cock began to shoot. It seemed that time slowed to a crawl and he shot rope after rope, forever.

But time was going too fast for Susan. "Wait! Wait! No!" She yelled, suddenly fighting to get her ass free from being further impaled by his stiffness. "Your precious sperm! Don't waste it into a damn condom! In my mouth! Mouth is better!"

But there was no way for her to get off from being speared by his big pole, then instantly turn around, remove the condom, and suck him off before he started cumming, especially since his dick seemed permanently lodged up her tight rear hole.

He continued to pound his seed into her ass, filling the condom. "Sorry, Mom, too late! Maybe next time!"

The two continued for many long, mutually satisfying moments until he was all spent, literally and figuratively. She flopped her chest down onto the counter, where he continued to cup and fondle her tits with both hands until his dick shriveled up and eventually popped out of her rear hole.

"What a way to say good morning! Phew!" Susan groaned, pure lust dripping from her voice.

Alan's hands had finally stopped groping her, but she grabbed them and encouraged them to keep going, even though the two of them were momentarily exhausted. She just didn't want the fun to end.

Katherine stood by, still just watching and touching herself. She was fascinated and extremely turned on, but also fuming with jealousy. Not for the first time, she was annoyed at how curvy Susan was in all the right places. I've been getting myself all pretty for Brother, and he hasn't even looked at me yet! How the hell can I compete with not only that body, but that outfit? Where they hell did she find that obscene maid outfit, anyways? The set of a porno movie? Grrr!

Alan finally looked at his sister and smiled. He tore himself away from his sex bomb mother and staggered to the refrigerator, propping himself up by leaning against it. "Man, that was good," he mumbled, lost for words. He mostly stared off into space with a shit-eating grin.

"Sorry Angel," Susan said to Katherine, as she slumped down onto the kitchen floor in total exhaustion. "I didn't mean to surprise you like that, but Tiger surprised me. Hooo boy! Did he ever! I had no idea he was going to do that. I mean, one minute he was just running his hands all over my exposed butt cheeks, taking full control of his big-titted sex toy mommy like he always does, and then... BAM!"

She clapped her hands together for emphasis. "His huge cock was deep in my ass!"

She began to put her maid suit back into some semblance of order, and even put on an extra optional piece that covered the shoulders. She could tell Katherine was feeling neglected, and she wanted him to devote more of his attention on her. That was as covered up as she could get, but it wasn't very much. Her nipples looked liable to pop back out of her top at any moment.

"I had no idea I was going to do that either!" Alan exclaimed, still exhausted. "But Mom, when I saw you in that maid outfit, I lost all control. And then the dry humping and everything. Geez! It was almost total luck that I fucked you in the ass and not in the cunt. Maybe I had your ass on my mind at the time because you said your tits and cunt had taken control and I was wondering if your ass had a say in things too. Funny thought, that."

He remembered that he still had the condom on. He removed it, half inverting it in the process to trap any transferred anal material inside, then tossed it into a nearby trash can. The condom reminded him of how aggressive and spontaneous he'd been. "I'm really sorry. I shouldn't have done that without even asking. I kind of lost my mind."

Susan smiled. She didn't mind how he'd fucked her ass so unexpectedly, since it worked out in the end. It had been one of the greatest times of her life, without a doubt. She also was unperturbed her son had almost fucked her other hole. In fact, in some ways she was disappointed that he hadn't.

She said, "Oh, don't be. All those hormones surging through you shows you're such a big, healthy boy. You may have crossed a boundary or two there, but I'll let it slide this time, so to speak."

That was a joke (and a play on words) because it was clear that all boundaries were pretty much gone now.

Alan smiled, "Yeah. A lot of sliding. We definitely need it to slide quite a lot."

She grinned and commented, "I actually got that one."

She went on, "Tiger, it seems we're going to fuck soon. And by 'fuck,' I mean you pounding your big fat cock into my tight little pussy. You know it and I know it. Angel, me, all your women - we have to have all of our holes ready to be impaled by your raging fuck rod at any moment. That's just a fact. I'm glad it didn't happen now though, because my cunt is SOOOO SORE from yesterday. I wouldn't have properly enjoyed it."

He smiled from ear to ear, happy to hear her confirm that. The way she kept waffling on the issue, he needed a lot of reassurance to know that she was fully behind the idea. But he just said, "I know! Last night was so intense. And then so was this morning. I can't handle this much intensity. My meter for intense sexual experiences is on overload. I have no idea how I'll be able to go to school after that."

Susan asked, "Who says you have to go to school? My cunt is in bad shape and you just destroyed my ass too. Oh God, my son-fucked, sperm-filled ass! I think I need to stay in bed all day and recover."

She looked at him with puppy dog eyes. "Stay at home and play with me? Please? You could be my 'nurse' and take care of me. And by the way, even though my pussy is wrecked, my mouth and my cleavage still work just fine."

She licked her lips ostentatiously, then pushed her tits together, creating an extra deep line of cleavage. Clearly, she was pointing out that even though her cunt and ass were off limits at the moment, she could still keep him buzzing all day with plenty of blowjobs and titfucks.

"Mom, I'd love to, but you know I can't. School. Tests." He hated saying that, but felt that he had to. He also didn't want to piss off Katherine, who was looking increasingly annoyed.

Susan seemed not to hear him. She closed her eyes and shivered suggestively as her fingertips delicately stroked between her thighs. Then her hands ran up her stomach to her chest and she pushed her boobs together again. She licked her lips with a hunger. "But what about my mouth and tits? Are you going to go to school leaving them all unfucked? They'll feel so left out. My tits are sad and neglected. They could use some fat and thick company."

She winked seductively at him and wiggled her shoulders ever so slightly. That set her heavy breasts gently swaying. Running with that idea, she bent forward and jiggled her huge melons even more.

Alan felt an urge well up inside of him to plow some more of her holes, especially since her slowly rocking nipples continued to poke in and out of her uniform, even as she tried to hold herself back some to mollify Katherine. The cut of the dress was such that her nipples couldn't remain covered for long unless she stayed as still as a statue and refrained from breathing. Not only was she not doing that, she deliberately let her fat tits spill completely out of her top again.

Susan's attempt to hold back so as to not steal all the attention from Katherine was only partially successful, at best. She was wired with energy after the great ass fucking.

Alan staggered over to a stool and sat near Katherine. He felt totally blown away in some unexplainable way, much more than just his "typical" sexually intense experience. He felt like he'd just machine gunned down a crowd of people or woke up from a thousand years of sleep.

But he slowly came back from some weird place to the here and now of the kitchen. Eventually, he reached out and poured himself a glass of pineapple juice, then downed it.

He knew Katherine was there, but he still hadn't fully digested her presence. Now he sat down on a stool next to her then turned and truly looked at her for the first time that morning.