THE TENTACLE CONTRACT: Monster Mom (throwback)

THE TENTACLE CONTRACT: Monster Mom (throwback)

Just before “pool day”, mom told me the whole story.

It was the absolute strangest of strange arrangements. In their youth, my mom and most of her 

friends had all attended the same magic school. While there, they had come upon a strange 

kind of contract, and, after some thought, had all entered into it willingly.

The contract was a simple one. They would gain permanent servants in the form of tentacles. 

These tentacles could be summoned at will, and they would be fully compliant with their 

mistresses bidding. They could be slimy or smooth, wet or dry, wide or narrow, dexterous or 

brutish. Whatever the summoner needed, the tentacles would provide. They found keys, 

washed cars, made coffee, did chores, fetched things, and in return… Well, they wanted sexual 

acts. But even then, it wasn’t much of a price. See, the tentacles were creatures that fed off 

pleasure and depravity, so, while they did want blowjobs and titjobs, and other selfish things, 

they also wanted to make sure that their mistresses came hard, and repeatedly. So, it was not 

exactly a fate worse than death, to have a small army of pleasure givers obeying their every 

command, for life. At the time of the deal, the girls were young, smart, horny, and adventurous, 

so, fuck it, they went for it.

However, of course, time went by, the girls became women, and the women became Mothers, 

teachers, professionals, etc… Even in a world of magic, and teaching at a school of magic, the 

tentacle contract was unusual in the extreme. Of course, they’d had to disclose the details to 

their spouses. In fact, some of their spouses had even shared in the… unique pleasures that 

were available to them. But, they kids were approaching adulthood, and it was becoming ever 

more difficult to keep it from them.

You see, the contract had a subtle trick worked into the fine print. While it was true that the 

lovely mothers only had to be sexual with the tentacles once per month, it was also true that it 

was insanely pleasurable to do so, and, after all, they were the masters of these sexual 

creatures. So… It was very naturally addicting. During sexual acts the beasts absolutely 

coursed with pleasure. They could make a person cum just from giving the tentacles “a 

handjob”. When they actually got to the parts where they slid into you, expanded, and writhed… 

Orgasm just didn’t seem like a strong enough word.

The need to be with them once per month quickly became a desire to be with them once per 

month. And then once a week seemed like a good precaution. And then thoughts like, “maybe I 

could just give them a quick blowjob before work”, or, “I have an hour for lunch, if I pack extra 

clothes, I could sneak up to the roof and have them rip these clothes off me, and gangbang me 

for most of an hour”. But again, it wasn’t like it was a bad deal. Endlessly useful, all-purpose, 

immortal servants; and the trade-off was being addicted to all the incredible sexual pleasures 

they gave you.

Not a bad deal at all.

Of course, this all went a little wrong on pool day. The day when the mom’s agreed their adult kids 

were all old enough to learn the truth. They worked with the school to get the pool and 

some privacy one Sunday; and they threw a big party. They told the kids about… well, most of 

the contract. Explained how it made a lot of weird stuff over the years make sense, and just 

basically put it all out there so they wouldn’t have to hide anything in their own houses. The 

creatures served food and drinks, they dried people off. They slapped butts and played on the 

mothers’ behalf, when told to, and, generally speaking, the whole day was a huge success!

Until…

Okay, so, like I said. My Mom and her friends were just trying to show us the harmless/awesome 

aspects of all the cool servant-type things that they could do. However, they were also, at this 

point, basically addicts who were surrounded by their drug of choice.

So things were going great and everyone was joking, flirting with neighbors, and making friends. 

Then things went south, FAST. One minute we were all laughing, and talking, and enjoying 

some drinks, and my mom was in the pool, sitting astride a giant tentacle like it was the world’s 

most comfortable floaty. Then she laughed, that charming little laugh of hers, and almost fell off 

the side. So she gave it a pat and told it that she needed something to grab on to. A moment 

later a few dozen spray-can sized protrusions rose up out of the top, and my mom’s face twisted 

into a mask of pleasure as she moaned, and rose up a bit before settling back down. She 

looked at me, blushing a bit, and we shared a look while I realized that one of those things had 

slipped past her bathing suit and was now nestled up inside of her. “Sorry about that sweetie”, 

Mom said breathily. “Sometimes you have to be very specific with them”. Then she gave it a 

playful slap, and said, “I meant handles”. And a moment later, two handholds had grown up just 

behind her… even though the first “handholds” were all still there. That meant that one was still 

inside mom. Then, in order for mom to grab the new handholds, she had to reach back. The 

movement made her move just enough that she stirred whatever was inside of her and made 

herself moan again. And, between the movement, the reaching back, and the moaning; she 

inadvertently caused the straps of her bathing suit to fall off.

Her arms were spread wide enough that they caught the falling straps before she was fully 

exposed. But we again exchanged a knowing look, where it was acknowledged that my Mom 

couldn’t move her hands without dropping her top. She STILL had what amounted to a giant, 

magically pleasurable dick inside of her, and she was astride a writhing sex tentacle.

If I’d had a clearer head, I’d have noticed that similar situations were happening all over, but I 

was pretty laser fucking focused on my mom and her giant tits, as her bathing suit struggled to 

hang on to the tops of them. Mom laughed, but as she did, she had to close her eyes, since, the 

laughter too, was causing pleasure to ripple through her. Then she smiled at me, and said her 

lips were a little dry. Of course, she couldn’t move her arms, so she just told her servant to 

moisten her lips. And again, the order was just not specific enough, so it was naughty with its 

obedience. Mom threw her head back and moaned loudly as a fresh, naturally lubricated 

tentacle, came up out of the water, and slid into her bathing suit via the area where it met her 

uppermost thigh. It made its way into her suit, and it wriggled and squirmed and visibly slid 

around inside of the suit for a bit, making mom moan, and writhe, and call out; though she still 

held the handles. Finally, it worked its way up the front of her suit, and, sliding up between her 

rather large and impressive tits, the tentacle then pressed itself to her lips, drawing a fresh 

moan, as it applied its version of lip gloss.

True enough, mom’s lips looked moist again, and had fresh color to them. The magic served its 

purpose, but I don’t think anyone cared about magic lip gloss working really well right at that 

moment.

Random moans and sex noises were now coming from all over the party as the tentacles and 

their mistresses got out of hand, despite being in the presence of their own sons and daughters. 

Mom, for her part, was no longer able to fully hold back. She had begun to slowly roll her hips, 

in a very obvious, “slow-fuck” motion. The tentacle that had popped up between her tits was 

moving in a slow up and down motion, matching the rhythm of her hips perfectly, and, every 

time mom glanced at it, she would lick her lips. Her mouth was literally watering as it hung just 

inches from her lovely, full, and freshly shined red lips. 

Everything about her body language implied that she was right on that edge of losing it, of giving 

into insatiable cravings; whether her son was watching or not. We just sat there, listening as 

Mom whimpered with pleasure, and other people moaned; as we kept looking into each other’s 

eyes. Mom seemed like she was struggling to find some way back from all of this, while still not 

being able to stop her hips from continuing their relentlessly sensual rolling motions. Then, after 

what seemed like an eternity of incredible, sinful, wonderful voyeurism had passed, my Mom 

glanced down at my crotch, saw my hard-on, and smiled. 

Her whole face lit up with it, and she arched her back on the next roll of hips. Apparently she felt 

that my having an erection gave her some kind of permission or freedom that she’d been 

lacking. And so she smiled brightly, and looked over at me once more. But this time she said, 

“You seem to be enjoying the show slugger.”, and again, her reply to my blushing was a deeply 

pleased grin. “Mmmm…” she moaned. Then she added, “If you like this… I mean, this is nothing 

baby. So… what do you say?”

My whole body was flushed with heat. My gorgeous, busty, long legged, long haired, lusty, 

sorceress Mother... was slowly getting off, and right in front of me! Not only that, but it was with 

the promise of a vast array of depraved things sitting just out of reach, and I couldn’t think a 

thought to save my life. I managed to say “What?”. Which summed up my brain-state nicely. But 

Mom was no longer surprised or flustered like I was. So when I said “what”, she just calmly 

replied, “Would you like to take your cock out, and watch your Mommy get ‘properly’ violated?” 

And as she said the last word, she leaned forward ever so slightly, and extended her tongue, 

giving the dick-like appendage in front of her a little lick. 

I nodded.

When I nodded, and said yes, there was a visible showing of tremendous willpower and a 

struggle to hold back finally dropping. Tension and inner strength that I hadn’t seen at work 

suddenly fell away, and Mom moaned out “Oh thank god!” 

Then, before I could even get my cock out of my swim trunks, Mom was already giving orders to 

the waiting beasts. And so, just before her mouth was stuffed full, I heard my lovely Mother’s 

voice, the most familiar voice in the world to me, as it said; “Fucking violate me! I want you to 

move me to shore, put my body on display right in front of my son, and then I want you to fondle 

and fuck my tits. Then after I cum, I want you to simulate cumming all over my face and tits. 

Then rip my clothes off of me, bend me over, and fuck me right in front of him. Fuck my pussy, 

my ass, my mouth, everything. And only stop to cum on me more!” She was riding the thing 

inside of her hard now, as she panted and moaned and continued to give filthy order after filthy 

order. All around us gorgeous women were getting “group-fucked” by tentacles, but I couldn’t 

look away from my own lust-filled Mother for even a second. She was mesmerizing, and 

intensely sexual in a way I’d never even imagined.

And she wasn’t done yet. “and don’t stop”, she continued. “don’t you dare stop! Not until my son 

admits that he wants a blowjob from his mommy! And the moment he does, I want you to bring 

me to him, force my lips onto his cock, and make me face-fuck that hot young dick of his until 

he’s cumming down his own Mother’s throat!”.

And just like that, it seemed to sense that she was done. The tentacles caressed, slid, pinched, 

sucked, smacked, held down, and rubbed at every part of her. They forced their way deep 

inside of her, and made her scream in harshly powerful orgasms around a mouthful of their 

“cocks”. They plopped her down in front of me, tore open her top, and titfucked her while she 

moaned for more. They “came” on her, over and over again, as tentacles and hot white cum 

poured all over her, and into her as well.

As I watched, I came a half-dozen times, but never stopped getting hard again at the incredible 

sight of such a richly sexual woman engaging in the absolute height of depraved sexual acts. It 

was almost an hour before I remembered that, per mom’s orders, she literally couldn’t stop now. 

At least, not with her mouth too full to give new orders. Not until I “helped”.

So I did. I grabbed my own Mother’s face in my hands, looked into her eyes, glassed over with 

pleasure, and told her that I wanted to feel my cock in her throat. And the second I did, the haze 

in her eyes cleared for a moment, I could tell that she was cumming again..

As soon as the moment passed though, the tentacles placed her gently in front of me. They 

seemed to check to make sure that their mistress was okay, and when they were satisfied, they 

went right back to their acts of commanded depravity. A host of the monster arms seized her 

body, bound her up, and pushed her face down into my crotch until I watched my cock slip 

between my own Mother’s lips, and felt her warm throat swallow me up.

It was incredible, and she seemed to love being made, forcefully, to suck me off and deepthroat 

me without any control of her own. That said, I had already cum 6 or 7 times in the last hour or 

so, and I wasn’t even sure if I COULD cum again so soon. But no sooner did I have that 

thought, than the tentacles “blindfolded” me, and the pressure on my cock stopped for a 

moment. I was suspended in darkness, my hard wet dick bobbing in the air. Then I heard my 

Mother’s voice again, as she stood up, and whispered lustily in my ear, “whatever you do baby, 

try not to think about the fact that most of your friends are here today, watching this. And, 

definitely try not to think of the implications of what this means for our lives from now on, now 

that us Moms have embraced being such wanton sluts in front of you kids. Because, I’m pretty 

sure that after today, you’ll be seeing a lot more than just tentacles gangbanging your Mommy.”

After that, there was nothing at all for what seemed like a full minute. And then Mom started 

talking. Maybe it was to no one, maybe it was to the tentacles, or maybe it was to a large group 

of my friends. But at the very least, she was pretending it was the third one. She talked about 

them coming up to her with their cocks out, about how she was touching them, then stroking 

them, then licking them. Then I heard her mouth fill again. And finally, when I thought I might 

cum just from what she was making me picture, I heard her say, “Oh my, what a naughty idea. 

You really are such bad boys…” And a moment later, I felt her lips wrap around the head of my 

cock once more. But this time, after a pause, her body bucked, and lips were forced down 

several inches as she moaned.

When I came, I came screaming, and I came harder than I had any of the times before. I had no 

idea what was actually happening. But from what I was hearing and feeling… A rather large 

group of my friends was repeating what the tentacles had done before. I was blindfolded, with 

my Mother’s lips wrapped around my cock. And that was exactly how I was when I came… as 

they gangbanged my mommy.

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