TOO PRETTY FOR PRISON

 

TOO PRETTY FOR PRISON

My Mom was a maniac. Not like, a murder type maniac; but definitely still a maniac. For one, 

she was a kleptomaniac, who couldn’t stop stealing things for the thrill of it. She was also a 

nympho-maniac, who couldn’t stop fucking things for pretty much the same reason. So, as I’m 

sure you can imagine, she got into trouble a lot as a teenager, and that didn’t stop as she 

blossomed into adulthood, and ended up looking like an absolute babe. Fast forward a few 

years and a marriage, and she became a certified MILF. 

I know, it’s my Mom. But… if you’d seen her, you’d get it. My Mom has long, beautiful hair that 

hangs down almost as far as her absolutely amazing ass. She enjoys dressing very 

provocatively and that is easy for her to do, considering she has the biggest tits in the entire 

town. It was more than that though. It would be bad enough if she was just the hottest fucking 

woman in 3 counties, uncontested. But, on top of that, she was very, Very, VERY into sex. 

You’ve never met someone who WANTED to suck your cock as badly as my Mother, and it 

SHOWED! Everyone she looked at, man or woman, was instantly seduced by how much she 

clearly wanted them. There is something deeply seductive about being desired, and a glance 

into my Mom’s eyes told you without question that she thought you were the gorgeous one, and 

she was counting on willpower alone to keep herself from stripping you down and fucking you 

right then and there!

So, when I was about 17, Mom was caught stealing again, and she was brought before the top 

judge anyone would normally see. All the other judges were out of town on a big fishing trip they 

took once each year; so she was at our little area’s equivalent of the supreme court.

The judge was about to sentence my Mom to serve a couple of years hard time, and then I 

spoke up and asked the judge to consider that, based on my Mother’s killer looks, and “thrill 

seeking” attitude, that she would be way more trouble for the prison than they wanted. On top of 

that, it could arguably be cruel to put someone like her in a prison. 

Now, normally, that defense probably would have been laughed at. But we were kind of a small 

town, obviously, I mean, I was defending my Mom in court because I was, in the words of the 

judge, “a pretty smart kid, so that should be fine”, and no one blinked at that. No lawyer? No 

problem, your Son has good grades, we’ll just use him!

Anyway, the crazy thing was, it worked! The judge said I was probably right, and that the people 

over at the prison would kill him if he sent her their way, and so he appoints me as my Mom’s 

guardian, advises me to keep her out of trouble, and declares her to be “too pretty for prison.” 

Now, in Mom’s defense, the fact that she could not go to prison did not encourage her to get into 

any more trouble than usual… Unfortunately, no more trouble than usual was still trouble all the 

time. At first, the police liked the lack of paperwork. They would catch my Mom shoplifting, or 

breaking into a place, and they would chastise her, tell her she knew better, and drive her back 

to our house to “turn over to her guardian’s care”. Basically, every two weeks I got a knock on 

the door and there was my Mom, in between two cops, smiling apologetically as they told me 

what she did and that I needed to do better to keep her out of trouble. 

But, the convenience of not having to file paperwork on her wore out over time. It took awhile, 

but over the course of two years the goodwill definitely faded. Probably because she never let 

up. Mom had sold a book, and made some serious money off of it. So, now she didn’t have to 

work, and that left her with nothing but time on her hands. So, allow me to assure you, in no 

uncertain terms… that my Mom and boredom was a dangerous combination. 

It didn’t help that every time the cops tried to bring her in she spent the whole time trying to 

seduce them. She was an endless walking temptation, and she never ran out of lines about how 

she felt about their handcuffs or their uniforms. So she was basically torturing them for 2 straight 

years with promises of lust, tight pussy, and a very willing captive. 

Turns out, they had limits. One day they dropped my Mom off, and this time they gave more 

than just a warning about how I needed to “put a leash on her”. No, this time they dropped her 

off with a very real threat. If they caught her stealing again, they were no longer going to resist 

her offers, they would absolutely fuck her right then and there. 

The moment they said it my Mom licked her lips and her face lit up excitedly. I gave her a 

warning “Mom… No.” But I knew it would only push her closer to it. So instead I immediately 

chastised the cop, telling him that, obviously, that was not going to make her try to get into 

trouble LESS. But they were apparently just as angry at me as they were with her. I know this 

for a fact, because the lead cop handed me a piece of paper with a website on it, and the URL 

was literally gangbanging(my first name’s)mommy.com. 

I was so shocked I choked on my own spit. But they were severely lacking in sympathy. “The 

guys at the station all know about it. Our buddies know about it, and if we ever end up uploading 

pics and videos, you can bet every guy in three counties will know about it before long. We can’t 

convince her to stop being a klepto-slut. So this is the very last attempt to convince you to find a 

way to make her behave. We are done being teased and taunted by the hottest slut in 100 

miles, and smiling like idiots as she grabs at our dicks with handcuffs on and begs us to let her 

loose. No more! Your Mother puts us in that position again, and you can watch the 

consequences yourself, on THAT website”, he said, pointing again at the paper in my hand.

Mom thought it was great! Me, not so much, but anything I MIGHT have been able to do was 

completely undone by them saying it all in front of her. I missed work and classes to stay home 

with my Mom and keep her, basically, under house arrest for the next three days. But in 

between normal Mom stuff like making meals, doting on me, and being the absolute sweetheart 

that she always was when she wasn’t around other guys; she wouldn’t stop talking about the 

cops threat. “Do you think they would do it right where they caught me? What if it was in public? 

If they don’t, what would that even mean? Do you think they would rent a sleazy hotel room just 

to keep it from public view? Can you imagine?! Buying a hotel room JUST to fuck me!” 

She was… not as mortified as I was, to put it mildly.  If anything, she was somehow seeing it all 

as a compliment. And Dad? Dad knew who he was marrying, and was never any help when it 

came to reigning in any of her impulses. That was why no one ever made a move to make HIM 

her guardian. It literally never crossed anyone's mind that he would be more mature about it…

On the fourth day though, I HAD to get to work, and I HAD to catch up on school stuff or I was 

going to get booted out of college. That night, as I was studying, I got a text message from the 

local police. It was a link to the website they’d showed me, but now there were photos and 

videos uploaded to it…

My Mom tried to rob a bank! Mind you, it was our crappy little local bank, but still! 

The police didn’t mind though. In fact, they honored the judges wishes, and not only didn’t lock 

her up, they didn’t even file any paperwork saying she committed a crime. No. Instead, when 

they were bringing her to the cruiser to escort her back to our house, so they could turn her over 

to my custody, they filmed it. And when their prisoner suggested that there just had to be some 

way that she could make it up to them, they turned the camera on themselves, called me by 

name, and said, “We warned you kid. If you can’t rein in your Mom’s stealing habit, we aren’t 

going to rein in her ‘dick sucking’ habits.” Then they pointed the camera back at my Mom and 

told her to get on her knees. Which she did, giddily. The first cop, a large black man, took out his 

dick and wagged it in her face, asking her if she wanted to suck it for him, and in reply, Mom 

purred out the words, “Yes officer”, and licked her lips in anticipation. There was a moment of 

pause, and it seemed for a second like they weren’t going to go through it. The lead officer, the 

one with the camera, actually took a second, and with a mildly sympathetic tone, he told my 

Mom that they were filming this, and that they were going to put it up on a website where her 

Son could see it. 

But when he said it, Mom not only didn’t look chastised, or appalled; no, she full on shuddered 

with pleasure. Like just hearing about it gave her a little mini-orgasm. Then she looked from the 

dick, to the cop, to the camera, and, with her hands still in handcuffs, she motioned to fix her 

hair a bit as she asked; “Do you think he’d want to? Like… do you think he might actually watch 

it?” And… there was no mistaking her tone. She didn’t sound horrified, she sounded, if anything, 

hopeful. For some reason… She WANTED me to see it. 

The cop with his dick out waggled it in front of her again, and Mom looked from the camera back 

to his dick. Then, she reached up to the top of her outfit, grabbed a silver ring, and unzipped her 

top straight to her navel. Her massive tits pushed free from the outfit, and she gave me, the 

camera, a wink, before leaning forward and starting to lustily, and aggressively suck the cock 

that was in front of her. 

Mom was hyper-focused, lusty, and worked him over like a pro. The guy didn’t last 10 minutes, 

and I don’t mean she took him straight there either. She had him hard in seconds, and babbling 

like he was going to cum in less than a minute. But each time he started tensing up, and 

standing on his toes, and looking like he was about to cum, Mom would release him from her 

mouth and gently stroke him for a bit. She wound him all the way up, eased him off, then took 

him to the edge again at least 3 separate times. His breathing was starting to sound like he 

couldn’t stop hyperventilating and I heard at least 3 voices around him making basic “Holy Shit!” 

comments as they watched. When Mom’s willing victim said, “Jesus Christ! I think she’s gonna 

kill me.” 

Mom apparently took that as a sign that he was already at his limit, and decided to show mercy. 

“Ready to cum?” She asked in a voice that could have corrupted a priest. In reply, he just 

gripped his dick in his hand, clenched up again, and said “Fuck.”, but he wasn’t quite there. She 

had him on the edge again, but wasn’t moving to take him over it. Then she looked at the 

camera, mouthed “watch this”, and then she looked back to the officer standing over her, and 

told him. “Now remember officer, my SON is going to see this… so when you cum, PLEASE, do 

me a favor… and aim for my face.”

He gripped his cock tighter, and started mumbling curse words, seemingly trying, desperately, 

not to cum yet. Like, so much so that I really think he had some kind of bet going. But then Mom 

added, “And next time, based on what you’ve been trying so hard to not to look at this whole 

time, I think we should skip the blowjob, and you should slide that monster in here.” And as she 

said it, she took his hands, guided them to her tits, and used them to push her massive breasts 

up and together. 

And that was it. He grabbed my a fist full of my Mother’s hair, and started jerking his cock as fast 

and as hard as he could. He seemed like he was trying to degrade or insult her, and he was 

talking about how he was going to cover her whore face in his load, and how he hoped she was 

ready for everyone to see her after he’d nutted all over her. Lastly, as he actually began to 

shoot, he told her that her Son was to about to see just how much of a cum-slut his Mother 

really was. But it looked like it backfired, as Mom moaned with each splash of cum, and in 

response to his words, she reached up, grabbed his balls, and began playing with them and 

coaxing more cum out of them as she responded, “That is baby! Cum for Mommy!” And either 

her words, her actions, or both, seemed to make him cum even harder! He absolutely slathered 

her face in cum. It ran off of her and dripped onto her tits, where it piled up and gathered, and 

began to run down them too. In the end she looked like all 5 cops had cum on her instead of just 

the one. 

After that, I could hear them talking about how intense it had been, and how none of them had 

expected what they ended up seeing. They were cleaning up my Mom and ignoring her 

invitations for “more” when the video ended. 30 minutes later, there was a knock at my door, 

and, blushing, the cops dropped Mom off, back into my care. 

They didn’t say anything, but the next morning, Mom made me breakfast, and practically 

begged me to tell her if I’d seen the video. I had, and I’d gotten off to it pretty hard, but I REALLY 

didn’t want to tell her that, so I just refused to answer her. She asked again though, 2 weeks 

later, after she’d got caught again, and the cops had uploaded a video of four of them running a 

train on her as they fucked her right on top of the hood of their cruiser, one after another, after 

another, after another. 

That time... I admitted that I’d seen it. When I did, Mom begged and pleaded with me to tell her if

 I liked it or not, and after several minutes, I finally caved. I told her that’d I liked it WAY too

 much, considering it was a video of my Mother getting group-fucked. 

But when I confessed, Mom softened. She ran her hands through my hair, then circled around 

behind me and rubbed my shoulders, telling me that she was sorry that having her for a Mom 

was hard sometimes. “But…” she said, her tone changing suddenly. “If I’d thought, even for a 

moment, that my behavior could be hot for you, instead of just embarrassing? Well, these last 

few years would have gone differently.” When I asked her what she meant by that, she 

sauntered back around into my view, and grinned wickedly. “For starters,” she said. “I think 

a birthday blowjob might have been a nice treat for your 18th.” 

I almost choked on my drink as Mom casually dropped that bomb, slowly unpeeling a banana 

that she’d picked up off the breakfast table. “And, my god!” She added. “Don’t even get me 

started on game night! Are you kidding me? You and a half dozen teenagers, studying or 

playing games, under the same roof as your Mom! Are you kidding me!?” Then she leaned 

across the table so aggressively that her large tits knocked things over and her hands pushed 

items to the floor as she ran her cheek along mine and placed her lips at my ear. There, she 

whispered sweetly, “If you thought a couple cops taking turns in a video was hot, imagine 

watching 6 guys that you actually know, throwing that ‘taking turns’ garbage out the window and 

just straight, gangbanging your Mommy, right in front of you.” And just when I thought my dick 

couldn’t get any harder, or my face any redder, she slammed her hand down on the table and 

rattled the dishes and silverware in time with her moans as she added, “Right, (moan/slam)! 

Here, (moan/slam)! On this, (moan/slam)! Table, (moan/slam)!”

At that, Mom finally slid back into her seat. Grinning from ear to ear. “So what do you say 

kiddo?” She asked, in between licking and sucking at her banana. “Did you like the video, but 

want to keep that fact just between us? Or do you like the video so much, that you want to start 

following the example of the city’s finest, and make your Mom a whore at home too?” 

I was too hot, and too turned on. I couldn’t even speak. Mom was killing me with that banana, 

and her words were like the hottest thing I could have ever imagined hearing. So after several 

failed attempts to fire up my brain enough to actually speak, I just nodded yes for my reply. 

When I did, Mom smiled victoriously, said, “Good!”, and set her Banana aside. At first, I didn’t 

know what she was doing. But a moment later, she disappeared under the table, and I felt 

delicate fingertips undo the zipper on my pants before a cool hand slipped into them and came 

back out holding my cock. 

I didn’t see it, but I felt Mom tap the head of my cock against her cheek as her voice came out 

from the under the table. “Mommy’s still hungry sweetie. Would you be a dear and… feed this to 

me?” I sure as hell managed a “Yes!” then, but even after I’d said it, she didn’t move. For a 

second, I was confused again, until I heard her one more time as she added, “Well then. Reach 

down here, take your Mother’s beautiful face in your hands… and fucking FEED it to me!” 

My first blowjob from my Mom wasn’t loving and sweet like I’d imagined it would be, it was a 

rough facefuck where I pulled on her long beautiful hair, gathered it up in my fist, and held my 

cock down her throat when I finally started cumming. But, later blowjobs WERE sweet. 

My first time having sex with Mom wasn’t sweet either, as I’d imagined. It was a rough and nasty 

gangbang involving six friends who were way more aggressive with my Mother than anything I’d 

come close to expecting, once they were given the chance. 

They straight up trashed the dining room. Not directly, but just from bending her over things, and 

climbing up on stuff to fuck different parts of my Mother, at different angles. The food and drinks 

she’d made for us mostly ended up all over the floor as she gripped the dining room table and 

screamed around a mouth full of cock as the force of her getting fucked rocked the furniture and 

eventually broke some of it. Her make-up ran everywhere, and her lipstick was smeared up and 

down the shafts of a half-dozen different cocks. It was rougher, filthier, and more depraved than 

anything the adult cops ever pulled off,and it was only our first time. 

But Mom assured me that we’d done great, and she’d loved every second of it. And even if that 

was my first time with her, I had other, slower, sweeter moments as well. In fact, my only 

problem with the whole arrangement, with my new, insane, sex filled, incredible life; is that I 

never did manage to stop Mom from stealing stuff. The police love returning her to me now… 

last time they brought her home with cum still on her outfit. It was the 3rd time that week.