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Billy sat at the kitchen table feeling depressed. Another night out with friends, another night of flirting with girls that led to blue-balls instead of getting laid or making any real connections. It had been so long. He was so lonely. On top of it all he was living at home with his mom.

She was definitely a “cool” mom. “She’s awesome.” he thought. They had a very open and honest relationship and she didn’t really place any stupid restrictions on him like some parents. “And she’s beautiful.” In her early fifties, she was still in shape and hot, as his friends often let him know, much to his annoyance.

Still, sometimes he thought if only he had his own place girls would think he was cooler and he’d have a place where he could take them and maybe even get a real girlfriend. But he knew given his recent luck, things didn’t even go far enough for that to be an issue. And that fact just depressed him even more.

As he was thinking about all this when she walked in – his mom that is. She was wearing a soft, light blue bathrobe. “And maybe nothing else” he thought, and then scolded himself for thinking about that.

Sophie still had that just out of bed look on her face. Her eyes barely opening up, she said, “Good morning sweetie. Did you have a nice time last night?” Her right hand lightly scratched her head, running her fingers through her hair. She had reddish brown; lovely wavy hair, not curly, just lots of waves going down to her shoulders.

He sort of grunted in response, shrugged, then said, “Yeah, it was alright.”

She stopped moving her hand through her hair and her head froze at an angle. “Oh? Not a very nice night?”

He kept his head down and didn’t say anything for a second. She pulled out the kitchen chair next to him and sat down facing him. He watched and felt a nice jump in his chest when she touched his bare knee and tried to look in his downturned eyes.

“What? What happened?” she asked.

“It was okay. Just… talked with some girls but it just didn’t lead to anything. Again. It’s just getting a little frustrating.”

“Oh, sweetie, I know. It’s been a long time since you had a girlfriend. You must be getting lonely?” she said, reaching over to give his hand a squeeze. Her hands were so warm and soft.

“Yeah, yeah… I guess that’s it.” he said tersely. He was surprised to find that her little hand squeeze had suddenly “woken him up down there”. He thought to himself, “Why the hell did I just get hard? Am I getting so desperate that my own mother holding my hand gets me hard?”

For some reason, thinking “my own mother” got his cock even harder.

Now he was starting to worry about whether or not she would notice it poking up from his flimsy boxer shorts. Luckily, sitting down like he was kept it pretty discreet.

“Oh honey, I know. I know.” she said with very sweet concern. Then she quickly stood up and said, “Do you want a hug, baby?”

The thought startled him so much, he nearly jumped, which was of course was what he thought he should avoid! But something deep in him felt a pull, and couldn’t say no to a request for such close contact with a beautiful woman who was nearly naked. That deep part of him didn’t care if it was his mother.

Actually, he was realizing, some part of him was more excited because it was his mother.

Meanwhile, she had her arms out wide open, while looking at him in such a caring and loving way.

Slowly, without really thinking, almost like in a dream, he stood up and went into her warm embrace. He felt the soft, plush bathrobe against his body. First his arms, then moving closer to his chest, he could feel it through his t-shirt.

Of course, then he could feel what was under that bathrobe. Her soft skin. Her wonderful chest; he could just barely feel her nipples against his body.

Even though he was taller, she put her arms over his shoulders and he put his hands on her waist. He always loved those soft hips. And in general that extra layer of softness that women have there.

And then, it happened. He moved his hands further around her waist, to just above his mother’s ass, and his hips and his rock hard cock came against her body. He sighed deeply. It felt so good. It felt like wonderful relief. For a second.

His mother did a quick intake of breath. And her formerly warm and welcoming embrace turned rigid and startled.

To which he responded by freezing and also becoming rigid all over his body. Only one part of him became, a tiny bit, less rigid, but still hard enough to feel against her frozen body.

She noticed his tension, immediately felt terrible and started babbling: “Sweetie, I’m sorry!… I was just surprised… I mean it’s totally natural and understandable! Not that I’m so sexy, I mean but…. You must really be feeling desperate, actually… Oh, I’m so sorry! I didn’t mean it like that baby!”

She had broken away from him while she ranted. But after that last thing she said, she looked at him, saw a mortified look on Billy’s face and brought him back into her arms.

“Oh honey, it’s okay! It really is. Don’t worry. I know you didn’t mean anything by it.” Now she could feel he was still hard against her body again. She decided to just keep holding him: prove to him it’s okay. She didn’t mind. She didn’t mind at all.

Actually, it felt wonderful but she hardly wanted to admit that to herself. It was just her natural desire to comfort and please her son, in whatever way he needed. Well, not EVERY way he needed… right? Then again why not? What? What is she thinking?

She decided to hold that thought. She broke her embrace, held his shoulders and looked him straight in the eyes and gave him a gentle, comforting smile. She leaned in to kiss his forehead.

It was a simple light kiss but he had never felt such electricity and heat from a kiss by his mom before. She let go of his shoulders and he walked away.

Sophie was left with her thoughts of right and wrong and her concern for her son, once again.

She had a strict Catholic upbringing and spent much of the rest of her life trying to unlearn what they had taught her. She called herself a “recovering Catholic.” She had questioned all the morals and every expectation they had imposed on her.

Except she had never seriously thought about this one. i****t was a universal taboo. It was just plain wrong according to so many traditions. Different cultures defined it in different ways and there had been a few exception throughout history. But it was clearly wrong.

Maybe it was according to those traditions but as she thought back on how it felt with her son in her arms, she FELT it was RIGHT. Deep inside her it felt good and she knew she wanted it. She wanted her son.

Then her old Catholic upbringing really kicked in: is there some way of getting around this rule? Is there some way she could comfort her lonely son, in a way that… didn’t really count as i****t?

Then in a flash she remembered how she and others had gotten around another big rule: no sex before marriage. Anal didn’t count. It was only really sex if he put it in your vagina.

That’s what they reasoned. So she and a few of her girlfriends had all had anal sex before they ever had vaginal intercourse. She liked it. She wasn’t so sure if all her friends liked it so much, but she did.

Even after she decided the whole thing was bullshit, all those rules and all that shame, and started having sex when she wanted, she still liked anal. It just seemed more naughty and intense for her.

But it didn’t really count.

So now that she found something that really is wrong all over the world, not just according to the Church, she could still use that loophole. She remembered how sad and dejected her son had looked. He really needed her.

Billy had gone for a walk to clear his head. When he came back on his way to his room he saw his mother sitting on the couch in the living room. She had a look in her eyes he didn’t know how to place. It made him stop in his tracks.

“Mom? What’s going on?”

“Sweetie, come here and sit next to me.” He moved over and sat on the couch leaving a foot or so between them. “Now, I’ve been thinking a lot about what happened this morning.”

Billy tensed up and seemed like he was ready to jump up and leave. “It’s okay. Really, I told you it’s okay. Don’t worry.” She said as she took his hands into hers again.

And again with her touch and all the tension in the air he was starting to get hard.

“No, I’ve been thinking about just how lonely you’ve been and what I can do to help. Clearly, you are at least somewhat involuntarily attracted to me as this morning showed.” She glanced over at him to gauge his reaction. He just seemed slightly frozen in anticipation for what she’d say next.

“Now i****t is just plain wrong. You know that. We both know that. But… and I have no idea what your reaction to this will be, but…” she snickered at the pun in spite of herself. “But, I was thinking of a way we could get around that.

“When I was a teenager growing up with all those strict Catholic families, we used to say, ‘Anal doesn’t count.’ We were desperate for exploring, and enjoying, sex. For the comfort and excitement of that intimacy. So we decided that was a way to do it guilt free.”

Sophie swallowed hard and said: “I decided I want to offer the same thing to you.”

Now she looked up at her son again and saw his jaw dropped, staring at her.

“You mean that….” he stuttered out.

“Yes, I’m offering for you to be with me as long as you only put it there.” She pointed back to her hips. “I’m offering you my ass.” She gave a small Mona Lisa smile while looking in his eyes.

“I know some people don’t like that. They think it’s gross. But if you want to, you can.” she said.

What Sophie didn’t know is her son had always fantasized about anal sex but had never tried it with a girl. “I… I like anal.”

“Well, okay! But I guess, I should check to make sure you’re telling the truth.” she said with another mischievous smile.

Billy watched as his mom reached over to his lap and rubbed the bulge poking up from his jeans. “Yes, it does look like you like the idea.” Then she brought her other hand over to reach together and unclasp his jeans. She slowly pulled his fly down, each row of teeth seeming to take forever to build up tension, then release and separate, build tension, release and separate, build tension, release and separate… until it was all the way down. And his cock was straining to burst out of his boxers.

His heart jumped as she reached into the hole in his underwear searching around for the treasure in there. She had it in her hand, wrapped around the whole thing. She pulled it out and stared at it.

“Oh baby, it’s beautiful. Any girl would be so lucky to have this….” She leaned her head down slowly but directly, while slightly opening her lips.

He was in heaven. Billy couldn’t believe his own mother had his cock in her warm, wet mouth.

Apparently, oral didn’t count either.

She took a few inches in. Then she took it out. Jacked it a little bit. Then licked the head and then down the shaft, before taking the whole thing in her mouth again. She looked up into her son’s eyes and managed to smile sweetly with her eyes while his cock rested in her mouth.

After awhile of this he was starting to get close to cumming. She noticed this, took her mouth off, and sat up.

“Okay, time to go upstairs.” She grabbed his hand and walked him to the stairway. She let go of his hand and walked ahead of him.

He followed after her and watched as, right in front of his face, the cheeks of her ass each went up and down under her robe, as she ascended the stairs, one step at a time. He wanted to just bury his face in those lovely cheeks.

He certainly hoped licking her ass didn’t count either…

Sophie could feel her son’s eyes on her ass as she ascended the staircase one step at a time. Meanwhile, she was thinking frantically.

Yes, she was thinking about the fact that she had just offered her lonely son her ass. As a horny, guilt-ridden Catholic teens, she and her friends had decided that it doesn’t count when it’s anal. She could comfort him that way without it really being i****t.

And yes, she was thinking about how she had just given her own son a blowjob. She hadn’t even really been thinking when she did it. She touched his hard cock (hard from the thought of fucking his own mother in the butt apparently) and then her hands just automatically opened his belt, unbuttoned his pants, and reached inside.

Then, again without thinking, she had bent her head down and put her boy’s rock hard, big beautiful dick in her mouth.

Actually, what was really on her mind as she slowly walked up those steps, was just how big that penis was. It’s wasn’t SO huge. It wasn’t the biggest she had ever seen. It wasn’t even the biggest she had ever fucked.

Her son’s penis was just bigger than any she had ever taken in her ass.

In fact, she had made a rule a long time ago that she would never a cock more than 7″ long in that particular hole. His dick was definitely bigger than 7 inches.

And yet, she had promised her son he could put it in her big round butt. She had promised herself he couldn’t put it in her pussy. That would clearly, completely, be i****t. It would be wrong.

So that’s what she was really thinking about by the time she reached her bedroom door and started to slowly turn her doorknob. Billy moved right up behind her. She could feel his cock very clearly against her bathrobe covered rear. He had stepped out of his jeans and left them down in the living room. He was only wearing a t-shirt and flimsy boxers now.

He moved one hand around her waist and pulled her closer to his body, harder against his cock. She felt his breath right against her neck and ear, which caused her to suddenly take in her own breath. She could feel him smile in reaction to this, as he nestled his face into her sensitive neck.

Sophie had always loved to be kissed there. Right where her shoulder meets her neck. It drove her crazy. She threw her head back and sighed in surrender.

She realized she had been holding tightly on to the doorknob, white knuckles showing. Now she pushed it forward. Billy pushed her forward, not with his arms but with his whole body. They moved as one hot mass of flesh toward her queen size bed. Right about now she felt like a queen, a queen who could have anything, anyone she wanted, even her own son.

“But only in the ass,” she reminded herself.

“I know Mom, only in your butt” he said in her ear, making Sophie realize she had actually said that out loud.

She also realized that they were now on her bed; she with her face down, he on top of her. Billy was running his hands along the outside of his mother’s thighs. Then he was fondling her hair, her ear, neck, chin. Then he had his fingers in her mouth and she was sucking on them.

“Just like he used to suck on my nipples,” she thought to herself. And the thought made her nipples harden even more.

“Just like I used to suck on your nipples, huh, Mom?” he whispered in her ear.. It sent a shiver down her spine to hear him echo her thoughts. She definitely hadn’t said it out loud this time because his fingers were in her mouth.

Maybe they were just on the same wavelength. Maybe she hadn’t actually said that last thing out loud either?

Now his hands had moved down to the hem of her robe. Now they moved up her legs. He ran his hands over her smooth ass. He moved them down her curves, between her cheeks. Her son’s finger’s grazed against her tight back entrance. Then her son was touching her pussy.

The feeling of his fingers in that forbidden place suddenly startled her to attention.

“No, Billy. No. You can’t touch me there. Only my ass. That’s the rule.” she said, surprising herself at how sober she suddenly sounded.

“But you touched my penis?” he said in a soft, half matter of fact, half pleading voice.

“That was different. You just can’t touch me there.” she said, matter-of-factly.

“Okay.” he said, trying not to sound too disappointed.

Then Billy remembered what he had been thinking about while his mother seemed to take an eternity to climb the stairs. He slithered his body down, across her back, until his face was directly in line with her soft, round cheeks. His eyes could just barely see under her robe from the angle her was looking and the way it had been ruffled around from all the movement.

Now he decidedly grabbed each side of the bottom of the bathrobe and FLIPPED it up.

There. There was a perfect view of his mom’s bare ass.

He buried his face in it.

“Oh, Billy…. oh, sweetie… ohhhhh….” Sophie sighed over and over. Billy’s nose was in the crack of her butt and his tongue… his tongue was licking her ass hole and she was loving it.

“I guess I got my answer: ass licking doesn’t count.” Billy thought to himself. “I also wonder if licking her pussy counts but given how she reacted to my fingers, I probably shouldn’t try.”

Instead, he moved his hands over her ass around to her hips. He grabbed them and pulled so that his face got buried even deeper into her smooth cheeks. His tongue probed deeper trying to go INTO her ass, not just along the tight folds of her sphincter.

“This feels so naughty… and wonderful,” Sophie thought to herself. “But it’s a good thing he’s doing that so her loosen me up as much as possible before he puts that monster in.”

As if on cue, Billy extracted his face from her ass and sat up. Then he moved along her body again and found her face. He slithered his mouth around to hers and shoved his tongue inside.

“He’s such a nasty boy!” she thought to herself as she wrestled her tongue with his and moaned without shame or restraint.

Now she could feel his hard cock against her ass again. Only this time he was naked, (“When had he taken those boxers off?”) and she could, for the first time, feel his bare rod against her bare backside.

“Here it comes,” she thought.

He took his cock in his hand and guided it against her nether hole. He pushed his purple head against the opening. It widened. Half of the head was inside his mother’s bum. There. His full cock head was inside her ass. And she was moaning. He pushed.

She moaned again but in a different way. It was a deeper moan. Billy couldn’t quite tell if it was a moan of pain or pleasure. If he only knew that Sophie couldn’t quite tell either.

He pushed a little further inside her. He grabbed her cheeks and spread them. There was his cock disappearing in between them. He really was in his mom’s ass.

He started to pull out. Then push in again. Then out. Then in just a little further this time. He was fucking his mom’s ass. Slowly.

Now he grabbed her hips and started pumping in and out, owning her ass. It was his ass to fuck. It was so tight around his cock. This sweet ass was his.

Then he heard his mom: “Billy! Please, stop! Slow down! I can’t take it like that!” She was looking back him, with an anguished look on her face, tears starting to swell in her eyes.

“Oh fuck,” he thought.

“Oh my God, Mom… I’m so sorry! I got carried away… and just lost myself. I lost you. I wasn’t thinking. I’m sorry!”

“Oh Billy, you didn’t lose me. It’s okay. I want you to lose yourself. I want you to feel good and even forget that it’s your mom that you’re having sex with… in her butt. I want you to imagine it’s some beautiful girl you’re with. Just… I’ve never had someone so big in… there.” Sophie moved her eyes in the direction of aching rear.

“Mom,” Billy said, “I don’t want to imagine you’re someone else. This is amazing being with you. You ARE a beautiful woman. I’m just so sorry I hurt you.” He leaned down and sweetly, gently kissed his mother on the cheek. She closed her eyes and sighed.

“As far as this.” he said while giving her a little nudge with his dick that had deflated and slipped from inside her. “As far as this. I didn’t know. I didn’t know it was so big.”

“Billy, are you serious? You really didn’t know you had a large penis?”

“Well, some girls had said some things. But my friends told me girls always say that. So I didn’t really take it seriously.” Billy said while looking down off into space.

“Honey, trust me, you have a big dick. And I’m not just saying that because I’m your mother.” Sophie said, smiling to herself. “But don’t worry it’s not TOO big or anything! Normally, at least…. Well, for having sex in a woman’s vagina… it’s perfect. Just for anal sex, it’s – challenging.”

“Does that mean we should do it here after all?” Billy started to nudge his rod into the open folds of his mother’s clam, just an inch or two from the anal opening he had just been inside of.

Sophie’s jaw dropped.. She gasped. Her pussy begged for the rest of that cock. It wanted it. Sophie could have sworn it started to clench around the head of his cock and pull it in.

Then a few thoughts came to her mind.

“Billy! No, stop that! Do you realize where that just was?” she exclaimed. “You could give me an infection!” He quickly pulled out. He had never really pushed it in anyway. He was ready for this scolding. Though he hadn’t thought about the sanitation issue.

“But that’s not even the main thing. I told you: that’s off limits. It’s just wrong.” she said. “But it’s okay. I can manage to take it in my bum. You just have to at least start slower and more gently.”

“Mom, I’m so sorry. I haven’t been thinking at all, definitely not thinking about you enough….” Billy said with his head down and his shoulders drooping.

“Honey, it’s okay. You just have to slow down and think about your partner more. Those are important things to learn anyway.” Sophie had turned around more to face her son. Her bare breasts were now completely in the open, in front of him. She noticed he noticed this. She also noticed that his deflated dick was now coming back to life.

“There we go, my big boy!” She said pointedly looking down at his dick. “You like Mama’s tits don’t you?” Sophie took her boobs and pushed them together right in front of her son’s face.

Now Billy dropped his jaw and raiseed his dick, back up completely now. The sight and sound of his mom’s dirty talk and slutty show got him back in the mood with confidence, instantly.

“That’s it, I know you’re ready to give to Mama again, aren’t you?” Sophie surprised herself with her wonton show, as she slid on to all four and stuck her ass right up at her son.

Billy placed his hands on each side of her hips and ran his cock up and down her ass crack, slowly.

“That’s it. Just do it slowly… and gently. And Mommy can handle it. Mommy wants it.” Sophie moaned as she started to feel his cock enter her tight, waiting back hole. “Oh, yes, baby… slowly, slowly work it inside me. Oh God….”

Billy watched his cock disappear into his mother’s rear one… inch… at… a time. It felt so satisfying. He wasn’t even tempted to start going at it hard and fast: he was enjoying every delicious moment.

The sound of this beautiful, sexy woman moaning and almost grunting below him was surprisingly sexy to him. With each slight advance inside of her she let out another growl. He was starting to be tempted to give it to her hard. And he was getting close to being all the way inside her.

It was then that he noticed she started to make a little different sounds: maybe more pain than pleasure.

“Mom, are you okay? Does this feel okay?” Billy said.

“It feels absolutely amazing, sweetie. Just amazing. But yes, it’s definitely starting to hurt. Just…” she gasped. “Just, stop there for a little while. Let me get used to it.”

Sophie panted as she grew accustomed to the feeling. She knew she could do it. She loved her son and could do this for him: give this – her ass – to him. She just needed some time.

After a little while, she turned her head around a bit and said, “Okay. Okay, you can go in a little deeper – very slowly.”

Billy so didn’t want to hurt her. He ever so delicately moved inside her more, just a tiny bit more.

“Ohhh! Stop, stop! I’m sorry, I just can’t take it any deeper!” she gasped, leaning forward pushing her face into the bed.

Billy started to pull his dick out of her. “No, it’s okay.” she said. He froze. “You can do it. Just not that deep. Can you control yourself from going too deep?” she asked. “Even when you really get excited?”

“Of course! Of course, Mom: however you want it. I can do it.”

Sophie smiled back her son and looking right into his eyes she said, “Okay; then get excited again! Give it to me!” She faced her head forward, and said again, “Give it to me!”

Billy didn’t need to hear it anymore times than that! He moved his cock into his mom’s beautiful round bum again. Before going too far, he pulled back out. Then in. Again, back out. Now he was clenching into her hips with both hands. Now he was really pumping in and out of her fucking perfect ass.

And she was loving it! Sophie couldn’t believe how exhilarating, naughty, dirty, and marvelous this felt: being fucked by her son in her ass. She wanted more! But he was careful not to go too deep and hurt her. It was perfect.

She knelt down and bit into the pillow like an a****l. Yes, there was still some pain. But it just added to the excitement.

Billy moved his hands from her hips to her breasts, massaging them as he continued pump in and out of her lovely round rump. He bit into her should just a little bit. Now he released her tits and reached to turn her cheek back toward him. Now they were kissing, wet tongues entwined while he kept going in and out of her backside.

They separated and Billy stopped for a moment just holding her. “I love you, Mom.”

“I love you too, baby.” she said with her whole heart, savoring the moment. Then: “Now, are you ready to cum, honey?” she asked.

“Really, can I? It’s okay, now?” he said.

“Yes, baby you can. I want you to cum. I want you to cum in Mommy’s ass.”

Hearing that nearly made him cum right there. But he didn’t.

He started pumping in and out again. Faster than before. Through clenched teeth he said: “Yes. Yes. It’s so good. You’re so fucking sexy, I can’t believe it.”

“Yes, baby. Give it to me. Cum for Mommy. Cum right in Mommy’s ass like a good boy.” she said.

“Yes, yes, I’m getting close Mom! Yes, so close!” he started pumping even harder. “So close! Yes, yes,” still careful not to push too far up, he froze halfway up her rear and dug his fingers savagely into her hips. “Yes, yes, I’m cumming… I’m cumming!”

He released inside of her gush, after gush of hot jizz he had built up for far too long. He panted as the orgasm washed over him. Then, he collapsed on the bed beside his mom.

“Oh honey, you look so happy!” Sophie exclaimed as she reached over to touch her son’s face.

He pulled her to him in a warm embrace.”Oh Mom, I am happy. Thank you so much. That was… amazing; perfect; exactly what I needed.” He stroked her long beautiful hair as he held her.

“But Mom, did you cum? I didn’t make you cum did I? I can’t believe it: that’s so rude!”

Sophie laughed slightly, “Thank you for thinking of me. But that’s okay sweetie. This was for you.”

“Well, can I make you cum at some point?” Billy asked.

Sophie smiled. “That’s very nice of you to ask. ‘I don’t know.’ is the answer.” She ran her hand up and down her son’s back and nestled her face into his shoulder, as she thought about it. She gave another Mona Lisa smile just to herself.

She pulled her head back, looked him, and said, “Only if we can figure out a way to do it that doesn’t count.”

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