6 Times a Day

Drunk Dargon Special 🐉 [ 19 / 20 ] 5K words

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Back in Alan's room, Suzanne thought about the situation. Okay, so we can't fuck. However, what if he fucks me up the ass? If I can get him into it, that'll be another thing to give me an edge over everyone else, because of my superior experience and natural skill. I can out-fuck anyone, in any position. And with Susan listening, it'll help drive her further down the slippery slope and start her thinking about the possibilities of anal delights. I like it!

As she renewed the conversation, there was a twinkle in her eye. "Listen, Sweetie, we can still respect your mother's boundaries AND fuck. We can just use my other hole."

Alan looked at her dumbly. "A blowjob? An aggressive mouth fuck?"

"No, silly. Not that hole. Has anyone taught you about anal sex yet?"

He grimaced. "Anal sex? No, that's one thing I don't want to learn. That's so gross and soooo gay. It's just for gay guys."

Suzanne gave him a withering look. "No it's not. Straight couples do it all the time. Hell, even my husband fucked me in the ass on occasion, back when we were actually in love and had sex from time to time. Just think of it as another sexy hole for your cock to go into. It's just like a pussy, but even better in a way because it's tighter."

He still frowned dubiously. "I don't know. It's too weird. The idea grosses me out."

She sighed. "Alan, I'm disappointed in you. I expect you to be more open about people with other sexual orientations. Okay, look. It's one thing to not want to BE fucked in the ass yourself. That's okay. I wouldn't ask you or want you to do that. But fucking a woman in the ass is totally different. A WOMAN, remember. Not to mention, you've had your finger up women's asses often enough lately to know how it can excite us. And we've even fingered your ass some too."

"Yeah, but that's different," he mumbled petulantly.

She planted her hands on her hips and challenged him, "How? Just close your eyes and imagine you're fucking my cunt, doggy style. The holes are practically right next to each other anyway. It's almost the same. And it feels great! Both for me and for you. Not all women like it, but I do."

He still complained, "Why can't I just fuck your pussy then? That would feel even better. I think about fucking you all the time."

Suzanne leaned into his ear and whispered, "Let's not talk about that. Remember? Your mother was frightened off temporarily, but she's probably back with her ear to your door by now."

Then she said, much louder, assuming Susan could hear, "You're such a kidder. Of course we can't do that. You'll just have to content yourself with fucking my ass. Besides, I want to be your first assfuck."

Her voice dropped again. "Angel was your first fuck and first kiss, Akami was your first titfuck, and Glory was your first carpet munching." Speaking in a loud voice again, she continued, "I want to be your first something, so can't it be this? Please?"

In fact, she'd been the one to give him his first blowjob, but she hoped he didn't recall that at the moment.

When he didn't reply right away, she added, "You may find you like it even more than fucking a pussy. Some guys do."

He griped, "Yeah, those are fuckin' gay guys." He truly had a strong aversion to the idea of anal sex.

"Alan! Stop being so homophobic. Normally you're so mature for your age, but your attitude here really pisses me off. Haven't you noticed I'm a woman, and I'm asking you to fuck me up the ass? Should I go ask one of your friends, like Sean, if you're not willing? I'm sure he'd be more than happy to help me out."

He knew that was an empty threat, but it still drove his competitive instinct. It made him remember how lucky he was to be in the same room as a naked, horny bombshell like Suzanne. Dang! What am I thinking? This is Aunt Suzy we're talking about here. She's the embodiment of pure sex. If she thinks it's great, it must be. Hell, any of my friends would give their right testicle to be in my place, and yet I'm telling her "thanks, but no thanks?" I must be out of my mind. Besides, I've read plenty of erotic stories which have anal sex between a man and a woman in them, and I got off on that. It doesn't have to be a gay thing, right, if it's with a woman?

Suzanne got on all fours on his bed, thrusting her ass up high to tempt him. She wiggled it seductively while saying, "Come and get it."

Alan loved the sight. But he was more interested in her drooling, gaping pussy than what seemed to be the impossibly small, puckered hole just above it.

However, he said, "Okay, okay, I'll give it a try. But seriously... Sean? Yeah, right. Talk about an empty threat. And I'm sorry about the comments, but remember I'm still a teen. A couple of years ago I said 'that's so gay' or 'that's so lame' about every third sentence. I may be being treated like an adult at home, but my voice still cracks sometimes. This is all strange and new for me, you know?"

"Your voice hasn't cracked in weeks, Sweetie. All this sexual activity seems to have worked on your hormones, turning you more into a real, adult man every day. Your voice is actually noticeably deeper than it was last month, and I'm not just saying that. You're a real man now, and real men like you aren't afraid of anal sex with willing, sexy women." By cleverly implying that he wasn't really a man unless he did this, she knew she'd get him - she'd found the technique succeeded with almost all males.

He paused and thought some more. "Okay, I'll try it out... But if I don't like it, then that's it, okay?"

"Sure," she said, wagging her ass seductively in his direction. "But I guarantee you'll like it."

He was still reluctant, so he delayed by toying with her lovely body. He especially enjoyed fondling her ass and running his fingers through the wetness of her inner thighs.

Eventually, a frustrating thought occurred to her: Lube! We need lube! Shoot. I have some K-Y Jelly in my drawer in the underwear cabinet, but that's all the way downstairs.

Suzanne explained the lube problem to Alan. He suggested Vaseline, since he had some of that in his room, but she told him that wasn't appropriate for anal sex. She reluctantly concluded, "I guess I have no choice but to sneak downstairs in my birthday suit. I'll only be gone a minute. Don't give up on me and sneak off with your cocksucky mommy while I'm gone, okay?"

He chuckled. "Don't worry."

When Suzanne opened the door, she was pleased to not find Susan listening. But, knowing Susan's great cock lust, she didn't want to waste any time. She jogged downstairs to the underwear cabinet and back, holding her big boobs all the way so they wouldn't bounce around too much, since Alan wasn't there to appreciate the sight.

Once safely back in his room, she continued right where they'd left off, presenting the tube of K-Y Jelly that she'd retrieved.

Alan said, "Oh! Mom gave me a tube of that; it's around here somewhere. Isn't that stuff like Vaseline?"

She wanted to dispel that notion firmly. "NO! This is water-soluble. It's a lot easier to clean up than Vaseline, and much safer for delicate tissues like the rectum. It's much better for anal sex, believe me!"

Feeling a little embarrassed, he apologized. "I'm sorry. I guess I had you run downstairs for nothing. I think that tube's around here somewhere." He started to glance around the room.

She said "Find it later, for next time." She applied copious amounts of K-Y Jelly to his stiff dick and put more inside her hole, then got back on all fours on his bed, positioning herself to receive him.

He knelt behind her and drew his erection in between her legs.

He still felt very uneasy about the prospect of actually engaging in anal sex, so he was looking for some way out. He joked, "These two holes look so similar. I can't tell which is which. Maybe I'll just stick this thing here in this hole." He began to gently poke his erection around the entrance to her pussy.

"Don't you dare!" Suzanne cried out in alarm, pulling her hips away from him. She desperately wanted to thrust her hips in the opposite direction and impale herself on his shaft, but she couldn't forget the ever-present danger of Susan listening in on the other side of the door. Having Susan hear them fuck, and then break in, could ruin months of planning. "Come on! Don't betray my trust or I'm gonna tell on you," she teased him back. "I'm gonna say that you've been a very, very bad boy. A good fucker, but a bad boy."

Dutifully chastened, he positioned his boner at her other hole. "Okay, here goes..."

He tried to slowly put the head in, but it just wouldn't fit. He was honestly afraid of hurting her. "It's not working," he finally said.

"Just be more forceful," she told him confidently. "Stick the head in with all your might and don't worry about how I feel. Just do it!"

So he did. It took what felt like an incredibly long time to him, yet slowly but surely he managed to slide it in. It felt like his cock was being squeezed in a vise, and he wasn't sure what to think about it.

But really it was only the bulbous head of his cock that went in. That had been a big ordeal, and he didn't see the point of continuing, since he was still repulsed by the idea of anal sex. He was afraid that he'd hurt her if he went any further, because the resistance was so great. He sighed. "Sorry. That's all I can do. That hole is just too small."

Suzanne's breathing was labored as she panted for air. "Let me be the judge of that. I've never had any cocks in me back there larger than your long fat one, but I've had dildos go in there bigger than you. Just take your time and don't rush..."

He did some logical deduction. She's said she's had anal sex with her husband, but never had a dick in her ass larger than mine. So my dick must be bigger than Eric's. Heh! That's pretty cool. (Actually, she was exaggerating a bit to encourage him. His was by far the fattest that she'd ever attempted.)

He returned his attention back to the task at hand. "But I just can't do it anymore. I don't want to hurt you."

She thought to herself, That's just like Sweetie. He's too gentle sometimes. He needs to put aside his "Mr. Nice Guy" personality when he's in the bedroom. "Okay, fine. Let me take over. Lie on your back." She rolled on top of him as she talked. "You spread my ass cheeks apart and I'll guide you in."

He did as he was told and let her take control.

As she wriggled her hips while lying on top of him, she used her sphincter muscles to draw his erection in ever so slowly, relaxing and clenching.

It was still a long and difficult struggle. The entire thing seemed unnatural to him. He complained, "Why are we doing this? I don't want to even think about what else you do with that hole."

"Hey, you've been putting your finger in it enough lately. In fact, your index finger has had an up-close tour of all the best female assholes in town. Like this is soooo different. Just be patient. I know it's difficult, but it's worth it, trust me. You're getting there... slowly but surely."

His cockhead was well inside her ass now, then several more inches slid in until his hard-on thickened slightly towards the base. He grunted loudly and repeatedly as he pushed in deeper.

She grabbed her butt cheeks and spread them even wider. She urged him on in her scratchy voice, "Come on! We're almost there! Sweetie, keep it coming!"

He was finally starting to feel good as his thick pole went in all the way. He yelled as he bottomed out, "UUUUGGGHRAAARGH!"

He couldn't believe how tightly the walls of her interior flesh gripped him, nor how strange it felt to be so deep into this private, forbidden hole. The heat he felt envelop his engorged cock was hotter than any hand, mouth, or pussy he'd yet known, and the squeeze around the base of his erection was so tight that he could still barely comprehend how such a big object could worm its way into such a tiny hole.

Suzanne let out a big sigh and shiver of satisfaction. She hadn't realized how nervous and tense she'd been, and that had been part of the problem. She'd been so looking forward to fucking Alan that it was almost physically painful to still be denied.

Everything that had happened at the poker party had only further whetted her lust. But now it was all okay. She thought, Yeeeeesssssss! Sweetie is IN ME! True, it's not quite as good as real fucking, but it's close! God DAMN! This is the start of such a beautiful future! I'm so happy that I'm gonna cry, but I don't care! And with all our grunting and moaning, Susan must be listening at the door for sure. But I don't care about that either! All that matters is that I'm getting FUCKED!

She cried out, "Uuuuhhh, Sweetie, don't stop! Don't STOP! Now, we come to the good part. Start THRUSTING!"

When Suzanne relaxed, it suddenly became easier for Alan to move his cock. He started to slide his erection in and out of her clenching anus. His groin slowly and repeatedly pushed up against her ass as he continued to thrust in and pull back.

As he began to set a steady pace, he too relaxed, and then everything became easier for both of them. It was such a dramatic difference that it practically seemed like a miracle. His excitement continued to rise as well, thanks to what he was feeling, not to mention the show Suzanne was putting on. Man! This is weird. I'm in Aunt Suzy's ass! Ass fucking! Actually, it's not so weird after all. It's like regular fucking, but a hell of a lot tighter! What's the problem? Dang, this feels GOOD! She's so right again. Why do I ever doubt her?

"Oh yeah, baby!" Suzanne cried as she shuddered under his slow, powerful thrusts. "Move it just like that, Sweetie, just like that!" She started to pant and her reddish brown curls flew about in time to the rocking of her head. Parts of her ivory neck, chest, and breasts grew flush.

"I can't believe I'm doing this after we could barely get it in!" he exclaimed. What he meant was he didn't understand how movement was even possible after it had been such a long battle just to get his dick in her ass in the first place.

His pleasurable feelings were already intense, but then she started to rock back and forth while clenching her own PC muscle, seemingly squeezing his erection tighter and driving him to further ecstasy.

He thought, Fuuuuck! We're really going at it now! Just look at the way her ass is wiggling back and forth, churning all around. Hell, I could cum just from looking at that, but it feels a million times better than it looks! And the fact that I'm FULLY IMPALED in my Auntie! Jeeeesus!

Suzanne was so turned on by the sensations he was giving her, not to mention the realization that Alan was finally fucking her, at least in some way, that her unfilled pussy throbbed and gushed as if it were the hole being pummeled. Her clit practically hummed with excitement.

She still couldn't get over the fact that he had started fucking her. Sweetie is finally doing it! This is a real fuck! In the ass, yes, but now I know how good he can truly be! It's everything I dreamed he could be for me. It's so much more than just being dicked in the ass by a big cock. We're joined! We're merging! We're going to be together forever now, united in body and soul! Take me to the stars, lover!

Her whole body trembled with an all-encompassing orgasm that surprised her with both its intensity and its unexpected arrival. She yelled, "Ahhh, we're doing it! We're finally... YES! Hit me with it, harder, deeper!"

He had just started panting, due to Suzanne's rhythmic squeezings on his stiffness, and increasing the tempo of his upward thrusts, when he finally realized the significance of Suzanne's nipples darkening with blood and heat. Oh yeah! I know what to do with those!

He reached forward, and then twisted and pulled.

"EEEEEEE!" Her pale face turned red as she screamed. She involuntarily squeezed his erection painfully tight. Red splotches danced briefly over her chest and breasts as she jerked and fell forward.

She was so exhausted that it seemed as if she had melted into the bed. His dick popped out when her anus finally unclenched.

Suzanne pressed against his chest, panting into his ear, twitching and moaning. She opened her eyes. "Uhhh, unhh, uhh, Sweetie, you - uhh - don't know what - unhh - you do to me."

Trying to control his breathing, as well as his surging lust, he murmured, "Does assfucking always do that?"

"Not - aah - before. Maybe it's - aah - you. Let's - unnh - find out when I - unnh - can breathe again."

"How about I hold you a bit?"

"Wonder - ah - ful!"

He stroked her back, rubbing her butt cheeks as her breathing gradually slowed.

Her mind raced. Where did that come from? Anal has always taken longer before! And I almost passed out! Was it me or him? Nah, he'd only just started, so it must have been me. What got into me? Besides him, I mean, hee-hee! I was so horny, and so disappointed when I caught Susan listening. The poker party was soooo much fun, and... Brenda? Hmmm. I wanted her too and... Yes, that's at least part of it - what he did to Brenda. The others were jealous, but not Sweetie and I, and, and...

He asked with concern, "Are you okay?"

"Getting better."

"It didn't hurt?"

"Oh, Sweetie, you can't hurt me, you couldn't hurt me. I loved it! I want to do it again!"

He saw tears running down her cheeks, so he gently wiped them away. "Aunt Suzy! Were you... crying?"

She was embarrassed to admit that she'd been crying tears of joy. So she sheepishly explained, "Sometimes anal sex can be so intense that the tears just come out. But don't worry, it's a good thing."

"Are you sure? I can't stand to see you sad."

She nodded. She loved how caring he was; it almost made her want to start crying again.

"What happened? I had only just started."

"Sweetie, I don't know for sure. Suddenly everything just rushed into me - that we were finally fucking - something I had wanted for so long... I just had to take a break. I'll be okay in a minute. Did you know, I'd fantasized about you for years?"

"About me? YOU?! Years? No way! You're, like, Jessica Rabbit perfection! Look at you! Look at this nude body!" He cupped one of her big melons, then traced his finger down to her clit. "That would be like, I dunno, some world-famous supermodel fantasizing about her paper boy." He squeezed her clit and fingered the outside of her wet pussy lips a bit since his hand was there.

Suzanne grinned at him; she loved his genuine modesty. "It started out as an idle fantasy... You were such a gallant boy, and my marriage, well, let's not go there. I often dreamed about the man you might become, and watched over the years as you slowly became that man. And then you started competing in tennis and getting in shape, and all of a sudden you weren't a boy anymore. That's when my fantasies about you stopped being idle ones. Maybe eighteen months ago when you started filling out, I started masturbating thinking about you. And then this happened."

He was floored. "Wow, you? Masturbating about me? If you only knew how many times I masturbated about you! And how many more times I wanted to and didn't 'cos I thought you were family."

She smile at that. "Thank goodness for your medical diagnosis and treatment, or we'd still have to use our own hands to cum. You became possible, and I saw a chance to make my dreams real." Her scratchy voice became husky as she visibly started to fight back the urge to tear up again.

His hug tightened as he whispered, "It's okay. It's okay. I'm touched."

She shook a bit, lifted her head, and pulled up to look down into his eyes. "But you're not a fantasy anymore; you're a real person. You're a man now and somehow, somehow, you have more love in you than I EVER dreamt of. And it's not just that! So much about you is something like magic. Just touching you, and being touched by you, makes me tingle. And it's not only me, because I've seen you have that effect on everyone! Brenda, that seven-zeros wet dream" - "Seven zeros" means a divorce settlement of more than ten million dollars - "lost it just from being in the same room with you!"

He had some trouble shifting gears. "I'm still trying to get over the fact that you masturbated about me."

She laughed. "So many times! If you only knew what a horny nympho I am. I masturbate about LOTS of people, even your mother!"

"Huh? Well, that's one thing we have in common," he joked.

She laughed.

The mention of Susan got them both to wondering whether she was still listening. They'd been so loud that it would have been very surprising if she were not. In fact, they were surprised that she hadn't knocked on the door already, or barged in, just to see exactly what was going on.

He asked, "So you really masturbate while thinking about women, huh?"

"Sure. But only the hot ones! Both you and your mom are hot, and I'm unabashedly bisexual. But you already knew that."

"Her, yes. Hell, I imagine the house flies and garden squirrels masturbate about her when they get a good look. But me? I still can't believe it. I'm just so ordinary."

"Sweetie, you can trust me on this, and it isn't just me. You're something special. Brenda has the hots for you like I couldn't believe! Isn't that proof? You've got it, and I'm horny! So it's about damn time you give me what I really need!"

She said in a much louder voice, "WANNA FUCK?" She hoped and assumed that Susan could hear that through the door.

He got the message, and spoke extra loudly too. "Hell, yes! Let's fuck! I'm gonna fuck you some more, Aunt Suzy!"

"Hallelujah! I want you to stick your big cock in me again!"

They both snickered quietly at their effort to yank Susan's chain. Again they were surprised that she didn't immediately start pounding on the door.

Then Suzanne asked him in a rather quiet voice, "Are you sold on anal sex yet? Do you think it's worth the effort?"

He thought about that seriously. "At first, I wasn't. It's so damn hard just getting in there! So friggin' TIGHT! Is just your ass like that?"

"No. There might be some loose asses out there, but there are also some that are even tighter. Since you've got a growing stable of women to please, here's some advice: assume every ass will be a tight fit. That's especially true given how extra thick your Johnson is."

"Dang!" He shook his head in disbelief, thinking about tighter asses. "But that's not how it is in porn stories. In most of them they just ram it in the ass, just like it's a pussy."

Suzanne shook her head in disagreement. "Then you're reading the wrong stories. Forget what you've read in porn stories; anal sex is serious business. That also means that when it's done RIGHT it can be a more intimate and powerful experience, because it requires cooperation in order to do it right. That's because the very tightness which makes entry difficult can also make the friction of fucking extra pleasurable for both the man AND the woman! But if you just try to 'ram it in,' that can really injure the woman, tearing her back there and maybe having her need to go to the emergency room. That's a seriously unsexy outcome. So there has to be trust between sex partners if you're going to do it right, or at all."

"Whoa! Now I'm getting all scared again."

Suzanne rolled her eyes. She sat up on her knees on the bed and said, "Before we go any further, I think you need to know a bit more about assfucking. Pay attention, because, like I said, this is serious business. I'm ready now, but when it comes to anal sex, never, ever assume that a woman is really ready for it just because you are. Not even for a second round like this. Always be slow about putting it in. You've got an extra big knob on your extra long, thick cock, so be extra careful and gentle, but firm, about getting it in. And make certain about the lube first. ALWAYS use some kind of lube, because unlike pussies, assholes can't self-lubricate. Then, once you have the head in, pause and let the woman get used to your size. You are NOT small!"

He paid close attention. It was all news to him, since he'd always skipped the anal sex scenes when reading erotic stories on the Internet. Only now was he starting to realize how good it might be, if done right.

However, he was also feeling downright disappointed that his mother hadn't tried to interrupt them. He wanted to get her involved somehow. An idea came to him, which he quickly whispered to Suzanne. Then he got up and quietly snuck over to the door.

He said, "Speaking of lube, let me go get some from the bathroom." At the same time he said that, he jerked open his bedroom door, but only partially.