HOW BADLY

 

HOW BADLY

At my new college, things had been going well. Too well! I know that sounds odd, but you have to 

understand that while my social life, finances, and grades were all skyrocketing; all three were 

doing so on this tenuous thread that could very easily snap at any moment, and basically ruin my 

life. It all started with me being the only kid from my highschool who ended up at this college, so, 

naturally, I was totally on my own. Every friend, reference, and social contact I’d ever had was 

suddenly gone from my life. No one even knew my name! 

So, I went to my Mom for advice. Now, there are a few things that are worth mentioning about my 

Mom. For one, she was a self-made business woman with social status, money, and joy that 

she’d made from nothing; almost entirely on her own. But she was so much more than that. She 

was smart, funny, and the most flirtatious person you’ve ever met in your life. She was the kind 

of person who was nice to everyone, and that made some wives and girlfriends absolutely 

insane, but, since my parents were in an open relationship, it was actually fewer people than you 

might think. The next thing you should know about her, was that she was hot. Like, she’s my 

Mom; but seriously. She was so, so, so… so so so so so HOT. She had massive breasts, an 

easy going smile, and her hair was both long and absolutely gorgeous! Add to that her legs, and 

then her ass, and, uh, yeah; puberty was a confusing time for me. 

But, all of this kind of came together because Mom’s business, the one that had made her tons 

of money and also made her happy, was, kind of a, well, a whore house.  I mean, she didn’t call 

it that. It was a “resort” that catered to all your needs. But her staff was wall to wall gorgeous 

women who were 100% just, extremely well trained call-girls. Oh, and of course, Mom did all the 

training herself… So, yeah, add that to my teenage confusion. 

But, Mom wasn’t just the undisputed Empress of Call-Girls and good times, she was, as I said, a 

savvy business woman. Her business was run on the up and up, with government approval at 

every level through a series of shrewd exceptions and legal loopholes. She kept all the right 

friends, gave lavish gifts to all the right people, and, somehow, through what had to have been a 

TON of hard work, she also managed to run a business that she loved. 

So, in a new place, no friends, no prospects, and desperate for advice? Who better to ask than 

Mom? 

After a long talk with her, I ended up doing research on fraternities, and I eventually found the one 

I was looking for. I did my research. I joined extracurricular groups, signed up for a sport I was 

good at, and borrowed some money from Mom to donate to the right charities. Only after that 

was done, did I apply to the Frat. Fast forward a year, and I was busting my butt on a daily basis. 

But it was all coming together. At only 19, my grades were doing great, I had a series of amazing 

tutors, and my frat brother’s had managed to not only be my real and valuable best friends in my 

new, adult life; but they were also my contacts and my “ins” at several businesses that equated 

to the jobs of my dreams. Plural! I had 3 potential jobs that I was trying to secure for after 

college, and instead of desperately hunting them, they were basically competing for me! 

But that was the thing. Pull on any one thread, and I get kicked out of my frat, lose the jobs, lose 

access to my friends, and it all falls apart. Which brings me to the most insane weekend of my 

life… 

See, on the day when I finally thought I’d earned a rest, I came home from my 10th major test in 

a two week period, and, for the first time in over a year… My calendar looked clear. I heaved a 

MASSIVE sigh of relief, and collapsed onto my bed, VICTORIOUS! 

For all of 6 seconds. 

Then my best buddy knocked on the door, and turned my chill into stress. Again, it was 

complicated. Like, it was stressful, but it was stressful because good things were on the line. 

See, this frat was full of rich kids whose parents were absolute captains of industry; 

ESPECIALLY in my chosen field. So, even though it was a coincidence (mostly, like, our 

interests aligned for obvious reasons, but I didn’t befriend them for sinister reasons or anything), 

my three best buddies all had parents at companies that I wanted to work for. So, my best friend 

tells me that his Dad just popped in for a surprise visit, and it turns out that he wasn’t the reason, 

I was! His Dad was looking at a pretty serious offer, and he had apparently decided that he 

wanted to drop in on me, and give me a kind of surprise test to see how I reacted under 

pressure. Which, would have been tough, except that, when he brought it up, he got a laugh out 

of doing so to his peers. His peers, who, although being his friends, were also technically rivals, 

in that they worked for the two other companies that were looking into hiring me. 

So, my one friend popping in to tell me that his Dad was there to spring a last second “test” on 

me, turned into THREE friends all telling me the same thing, and suddenly the test was a group 

affair. So, there I was, standing in the common room of our Frat House, with my three best 

buddies and their Dad’s, who also just so happened to be three of my ideal future employers! 

They told me what the “test” was going to be, and make no mistake, no matter how simple a test 

it was; my career was riding on it. Hell, depending on how bad I could potentially mess it up, 

potentially even my college life, and status with the fraternity, (their Dad’s weren’t just corporate 

big-wigs, they were also all alums, and big donors to the university) was depending on this one 

weekend!

The test was a simple one. They’d driven all this way, and now I was to entertain them. They 

figured that the need to take care of an important client could happen in any industry, so… here 

were three VIP’s and their Sons. I was to show them what I could do. 

The problem of course, was that I’d spend every waking hour of the last year developing 

friendships, making contacts, flirting with their companies, and busting my ass to keep my 

grades up! I didn’t even know where anything in the city was beyond a coffee shop or two! But 

wait, it gets worse! Because I now had to “entertain” 6 people, all of whom were used to having a 

bunch of money, and I had none. None! Every penny that I used for everything had been lent to 

me by Mom, and at each stage, she’d anticipated it with me, and walked me through what I’d 

need, and why, before giving me the money. But right at that moment, I had enough for breakfast 

the next day and that was it! 

I tried stalling for time by talking about how sudden it all was, but of course, they just retorted by 

mentioning that, “That’s kind of the point.” I was succeeding in buying time, but only seconds. If I 

pushed that game too far, they would consider me to have failed their little test before it even 

started, and that, I was 100% sure, was one of the worst ways that this thing could go! 

Then, as I was mentally scrambling through all the reasons I was screwed, it occurred to me that 

Mom could fix this easily, but I couldn’t exactly ask them to wait here while I went and consulted 

with my Mommy! But then… 

I kind of could.

It was a risk, but, I knew what dirty little perverts all my frat Brothers were, and, I’d been surprised 

to learn at college that “growing up” appeared to be an illusion for most people. Like, the more I 

worked with adults, the more convinced I became that every last one of them was not only just 

“pretending” to be an adult version of themselves, but they all thought that they were the only one 

doing it! So, if my buddies were just 3 horny guys kept in check by society's rules, then maybe 

their Dad’s weren’t so far from that as they liked to make people think. 

I started by grabbing them drinks. Per Mom’s suggestion I kept one very good bottle of alcohol 

hidden away. I mean, very good by adult standards. Like, my buddies would have judged it by the 

percentage of alcohol, but their Dad’s were more interested in how expensive it was. Then, after 

pouring them drinks, I tried to, ever so casually, mention that I’d heard that many vendors and 

VIP’s ended up in “fun focused” activities, such as high end strip clubs, major sporting events, 

and even engaging with prostitutes. Then I pointed out that there were no big sporting events 

happening that night, and I very casually asked them if I should treat them like “real” VIP’s, and 

consider “everything” on the table.

Now, I literally just listed hot naked women, twice, and sports; and then I’d said but we were all 

out of sports. So while I’d totally left it open for interpretation, only an idiot would miss what I was 

asking, and these guys, while they were a bunch of horny old Dad’s, were NOT idiots. There 

was this whole silent conversation that happened then. Honestly, it might have been fascinating 

under different circumstances. The men looked at one another and grinned. I could almost hear 

one of them thinking something old timey like, “I like the cut of this kids Gib”. Then they looked at 

their Sons, and their smiles faded, and two of them looked at the rings on their left hands. They 

all had rings, but only two of them looked, and I think it was more, “but what if my idiot kid blabs 

to my wife”, and less, “but I could never!”. Then, they looked at one another again, and there was 

this long pause. After a minute, one of them shrugged, they all laughed, raised their glasses, and 

told their Sons that they had great taste in friends!

Which was awesome! Because I not only had an idea, I had a seal of approval for that idea, from 

the very people I was trying to impress, before I even got started! It was a simple plan. I had no 

money, but I’d be hard pressed to have a conversation with my Mom about what to do with 

money, even if I did have it, while the “clients” waited. So… 

Mom ran what was considered by many to be the best “adult resort” (read whore house) in the 

whole country. I could drive them there, and Mom could get them all VIP treatment at one of best 

VIP places, fucking, ANYWHERE! It was perfect! Except of course, things going perfect was not 

how my day was going so far, and I was foolish to assume that it would suddenly start heading 

that direction now. 

So, yeah. We got there, and they thought the drive up into the mountains had been great. They 

were happy to catch up with their kids, while also taking a drive with their actual friends. It didn’t 

hurt that it was to a location they were honestly excited to go to. Easy win. Then we got there, 

and the resort itself was incredible. The themes changed from area to area, but they were all 

breathtaking. Beautiful medieval maidens, gorgeous Geisha in Kimonos, and at each stage, the 

resort's aesthetic matched the motif perfectly. The best woodwork, and highest quality… well, 

everything! 

But of course, there was something odd right off the bat. Normally, the parking is packed. To the 

extent that Mom actually has a little reserved spot that she keeps for Me or Dad. But that night, 

there was almost no one there.

When we walked in, I told the guys (all 6 of them), to have a seat or look around, and I would get 

everything all set up. Then I went to reception and, quietly, I asked to speak with my Mom. I knew 

she was working this weekend, because she’d told me I could drop off my laundry or pop in on 

her if I needed to. So where was everyone? The receptionist called for my Mom to come out and 

meet me, and per my request, she got my “VIP’s” some drinks, and began treating them like they 

were customer’s waiting to be seen. After a minute, Mom waved at me from a nearby door, and I 

slipped off to talk with her. 

We moved out to an area in the Japanese section. It was a luxurious hot bath (picture a hot tub 

the size of a small, square swimming pool), with massage tables, and beautiful rice paper doors 

with incredible artwork inked into them. Mom sat down at the edge of the faux hot-spring, poured 

herself a small glass of, what was no doubt very high quality Sake, and patted the spot beside 

her. But, as casual as she may have been feeling, I definitely wasn’t, and this was no laundry 

drop off. 

In a panicked, high speed, super manic tirade, I began blurting out all the reasons that I was 

there, everything that was on the line, and how freaked out I was that my plan, and my life, 

appeared to be falling apart in front of me. When I was done, Mom raised her eyebrows at 

everything I’d just dropped on her, and finished her drink in one swig. “Wow.” She said, and then 

after a moment, she looked back to the reception area, and repeated it once more. “... Wow.” 

Then, she steadied herself, took a breath, and, very calmly, explained that, technically, they were 

closed for the evening. 

There had been an outbreak of something in the nearby town where most of “her girls” lived, and, 

even though most of them were fine; she’d made it known that they were going to shut down for 

two weeks as a precaution, and she and a skeleton staff had been making personal apology 

calls all night. She’d been giving refunds and discounts to cover for the inconvenience, and was 

basically just going to be staying at the resort and relaxing for the weekend when I walked in… 

without my laundry. 

I felt like I’d been shot. I was doomed! Mom looked up at me, frowned, and gave me a 

sympathetic, “Oh. Sweetie.” But, I had no idea what I was going to say. Then, Mom smiled, 

poured herself another saucer of Sake, and said, “Of course, there is still 1 working girl here. 

But,” and she gave one of her delightful little laughs, “I suppose that depends on how badly you 

really want this, and exactly just how good a time you want to show them”. She was smiling like 

she’d just told a great joke, but I wasn’t getting it, and I was starting to feel just the tiniest glimmer 

of hope.  She saw my expression, and apparently read it like a book. Because she tilted her head 

at me and said, “sweetie” in a way that very clearly told me I was being naive. 

“Only one working girl here”, she repeated. When I didn’t catch on fast enough she grinned, and 

added, “And, uh, you’ve sucked on her tits before”. That… that one confused me even more. 

Because I’d never “taken advantage” of any of the services at the resort. I’d have been too 

scared to ask. But as I was trying to figure out what she was talking about, Mom cut straight to 

the end of it, as she lifted her drinking glass up to the edge of her Kimono (elegant robe) and 

pulled it loose enough that I was staring at one of the tits she’d been referencing. 

I KNOW I got hard! I also know that I blushed, got dizzy, felt a flush of heat go straight through 

my body and leave me burning at a much higher temperature than the water Mom had her feet 

in. But I couldn’t speak. I was looking at my Mom’s tits! I’d been fantasizing about her for what felt 

like my whole life, and now she’d just pulled out one of her tits and put it on display! In a way that 

she thought was funny! FUCK!

But as my head swam, Mom glanced down at my hard-on poking at my pants, and just, smiled a 

knowing smile. Her not being offended could have had me asking questions for hours. Her 

smiling while looking at the outline of my hard dick could have me masturbating for weeks. But I 

didn’t have time to process either, since, no sooner had it happened, than she, once again, was 

forced to repeat herself. 

“Like I said sweetie… I guess this all comes down to, how badly do you really want this, and just 

how good a time do you really want to show them?” 

Then it hit me. I mean, it, fucking, HIT me. Mom wasn’t saying no! She was saying that she was 

a “working girl” at her own business, and that, she was… offering. To “work”. 

I gulped so hard I was worried that they’d heard it out in the lobby. But Mom just smiled, and 

waited. After a few moments, she pointedly glanced at a nearby clock on the wall, and then back 

at the lobby. 

She was right. The clock was ticking. I swallowed down some more of my nerves, and managed 

to ask her, “Really?” It came out more hopeful than I’d wanted it to. But, I was running out of time, 

and I was starting to get a handle on the fact that I needed to get my shit together and start doing 

more than blushing, and ogling my Mom’s breasts. “Really.”, she repeated back with a smile. 

There was something a little wicked in her grin that made me even harder. Then she added, 

“Honestly sweetie, I’m surprised you even considered. No, not surprised… intrigued. I get the 

feeling that, for all our honesty with one another, we somehow missed a very important talk at 

some point. But, to answer your question, fully, and honestly… Yes. Really.”

Another few seconds passed where I tried very hard not to picture my Mother “working” at the 

resort all these years, and Dad visited her! What was that about? But, before I could get lost in 

my own speculation, Mom asked her question one last time; and I realized I was out of time. I 

either had to go out to the lobby and tell my three best friends and their Dad’s, that the place was 

closed and we’d just wasted a one hour drive, or…

Or I could introduce them to my Mother.

“How badly do you want this, and how good a time do you want to show them?” She’d repeated. 

But this time, there was no levity to it. She wasn’t joking. Her voice was sultry, sexual, and filled 

with wicked promise. 

Honestly, I was confused, and flustered, and turned on to the point that it should have been 

considered a mental disability; but I gathered all that up, and all the strange undefined stuff that 

went with it, but that I hadn’t worked through yet, and I swallowed it all down. Then I lifted my 

chin, looked Mom in the eye, and told her; “I want it badly enough to say yes.” 

When I said it, she grinned at me. She honestly looked pleased with my answer, and there was a 

hunger in her eyes that made it hard to breathe while looking into them. “And how good a time do 

you want me to show them?” She asked, already rising to her feet, but making no effort to close 

the top of her Kimono again. It ended up hanging loosely in front of her, no longer fully exposing 

either breast, but instead offering an incredibly generous view of a truly massive cleavage line. 

She’d said “me” this time. She was serious, and she was reminding me what I was really 

bargaining for. What I was really bargaining with… But if I was going to do this at all, then I knew 

what the answer had to be, so I told her. “The best time. The best time they can ask for. The time 

of their lives, if you can…”. At that, Mom tossed back her head and finished off her drink. Then, 

grinning from ear to ear, she promised me, “Oh I can sweetie. After all, Mommy IS a 

professional.” Then, as she led me back towards the lobby, she teased me a bit by asking, 

“Aren’t I?” And I knew from knowing her, that I had until we got to that door to answer her. So, I 

acted quickly, and I gave her the “Yes Mom” she’d been hunting after. As a result, I was blushing 

even harder when we walked back into the lobby, and Mom gestured towards her waiting guests. 

She called out, “This way gentlemen,” and waved them over, before turning and heading down 

the hall to a room she apparently thought would work well. 

I could tell from the appreciative looks, the elbows, and the quickly exchanged banter that 

everyone who’d seen her had been very happy with “the woman I picked out”. She led us all to a 

large room, with a single, massive bed in the center. There was other furniture too. Some of it 

was very American. A couch, a chair, a dining table. The room was more a suite than anything 

else, and it seemed to be balanced between two worlds. There were set-ups and furniture for 

maintaining a purely Japanese look, but there were also American counterparts for people who 

didn’t want to take the game far enough to eat at a traditional Japanese table with Japanese 

utensils and traditions. 

We all filed into the room, and when we did, Mom looked at me like I’d forgotten something. 

Then, after a moment, she calmly said, “Would you be a dear and get the door please?” 

Of course! There was no staff there that day, but we were trying to pretend otherwise. So, I 

would probably need to pick up the slack a bit before I left for the, uh, festivities, and whatnot. I 

managed not to slap myself in the forehead, as I said “Of course”, and went to get the door. But, I 

didn’t stop myself in time, and before I could prevent the reflex, I added, “Sorry Mom”. 

Then I froze. 

Everyone looked at me, then back at her. Then one of the businessmen said, “Mom?” In a way 

that was a cross between curious and teasing. Like, he wanted to know why I said it, but he was 

making fun of me in advance, no matter what that reason turned out to be. Which, if I’m being 

honest, I sort of expected from his type. But, before I could panic, hyperventilate, and, I assume, 

die from embarrassment, Mom quickly defused the whole thing with one of her charming laughs. 

The moment her voice filled the room, every set of eyes happily moved to her, anxious to please 

whoever had made that sound. But Mom grabbed a bottle of Sake, and quickly poured four 

servings, inviting the Dad’s to sit, and clearly excluding my buddies from the offering of alcohol. I 

think one of them was 21, but it was hardly something they cared about at that moment. 

“That was my fault”, Mom confessed charmingly. “I was walking your host though the various 

packages and options that were available here, and I may have spent a little too much time 

teasing him about the fact that I have a bit of a Mommy specialty here”. That seemed to satisfy 

them, but it also intrigued them, and one of the businessmen asked her to elaborate. Which, 

served to panic me more, because I was pretty sure Mom was bullshitting on the fly; but, her 

response was so seamless that maybe she wasn’t... Either way, she rolled with it like a pro. 

“Well,” she began, already pouring a refill for two of them. “We have a University not an hour 

from here, and I am more than a mere worker here. I am also the founder, and owner of this 

entire resort.” Then she winked at me, and raised her glass in my direction, adding, “I don’t come 

cheap.” That got a few other glasses and some approving glances in my direction. “But,” she 

added with a playful smile. “Because I’m the “Mom” for all my girls here, and because I have the 

MILF body to go with it,” she added. Stepping back, placing her hands on her hips, and 

showcasing the truth of her words to the gathered men. Who stared at her with open lust and 

obviously agreed with her. Then she gave a little laugh, and waved away their stares with a 

modest, “oh you”, that succeeded in charming every last one of them. “Anyway”, she finished. It 

is very common for me to get requests to role play as my customers' Mothers. Or the Mother of 

someone they know. And, as I was teasing our gracious host this evening, when it is a group of 

men like this, the most common request that I get, is to play the Mother of whomever is paying. 

One of my buddy’s paused a second, and then asked, “Why though?”; which got a disapproving 

look from his Dad. But he stood his ground, and Mom was sweet as could be in answering him. 

“Well kiddo, sex tends to be more fun when it is taboo. For example,” she said. Then she placed 

her hand into a pocket of her robe and when she pulled it out again, she was wearing her 

wedding band. “People tend to like it very much when I wear this,” and before he could ask why 

again, she continued. “... because then you aren’t just sleeping with a beautiful woman, you are 

also bedding another Man’s wife. And when that happens, it lets people have sex and be 

aggressive with, not just a person, but a symbol.” The Dad’s were all nodding sagely, but they 

were also having her refill their drinks again, and their eyes had stopped moving above her chest, 

even when she spoke. 

As for my friend, he still looked like he didn’t quite get it, and, as much as I wanted this topic to be 

left behind, even I was surprised at how he wasn’t catching on by that point. He’d seemed 

smarter before my Mother’s cleavage was in front of him.

So, Mom solved it for him. She sauntered over to him with a sway to her hips that I had never 

seen before, but would never forget, now that I had seen it. Then she gently placed one hand on 

his cheek, and told him to close his eyes. He did, then she said, “Now, imagine me hitting my 

knees, and giving you a blowjob right here and now.” Then after a beat, her smile grew, and she 

asked him, “Sound good?” He nodded a definite yes. Then she continued, “Now, imagine one of 

your buddies brought you here tonight, and introduced me as his Mother. THEN, you still got to 

have me. You got to put your buddy's lovely Mom on her knees, and listen to her slurp on your 

cock, and tell you how big you were… Now… How’s that sound?” 

His face had turned red… mine too, again. He was nodding, and he definitely got it now. 

Unfortunately, he wasn’t the only one. From behind him, his Dad said, “I know I think it sounds 

VERY good.” He was walking towards her, and as he did, he was unfastening his belt and his 

pants. The other Dad’s were following suit, and one of them said, “I completely agree. Any 

chance that the package we got is comparable price wise to that one?” He was looking between 

me and Mom when he asked. But Mom just smiled, and answered him without hesitation. “Oh 

gentlemen, you needn’t worry about that. When I told your host our pricing options, he beat them 

all out, and instructed me to simply, ‘show them the best time they can ask for’.” 

Then she turned to face the three undressing men, and as she did, she leaned to the side to look 

past them, and call out to my friends. “Don’t just stand over there all by yourselves boys,” she 

said welcomingly. Then she looked from me to them with a smile, and said, “It sounds like your 

Dad’s and your friend have finished hammering out all the details of our little encounter, and I am 

just, so happy to finally meet some of my Son’s new college friends.” As she said it, she shot a 

wink to the Dad’s in the group, and they all laughed, smiled, or nodded in approval as she 

“slipped into the role of pretending to be my Mom”. 

Then Mom took a step back, and untied the sash that held her Kimono together, letting the robe 

fall mostly open. Her large breasts were barely covered at all, and any touch or breeze was 

capable of exposing her completely. “Come on over here and introduce yourselves”, she purred; 

and even their Dad’s froze in the raw seduction of her tone. One of them paused, naked, but no 

longer moving towards her as he said, “I think I’d like to see that actually. Yeah. Go ahead and 

introduce yourself to your friend's Mother here junior.” Another of the Dad’s laughed and chipped 

in with, “Yeah, Son, I think you should give Mrs (my last name”) a friendly hug, and say hello!” 

That got a laugh and a clap on the back from the third Dad. 

At first, everyone seemed kind of unsure of what to do. One of them literally gave her a hug that 

lingered way too long because she was beautiful, big titted, and naked under her robe. Then 

Mom seemed to break the tension and remind everyone why they were there, when she said, 

“You kids really lucked out tonight huh? I mean, your friend here was only supposed to bring your 

Dad’s to meet me. But now, because of pure luck, all 6 of you not only get to meet (my first 

name)’s Mother… But you also get me for the whole night as you're bought and paid for whore. 

So…” she said, turning to face me, her Kimono falling to the floor in a pool of silk at her feet. “As I 

was explaining to you earlier… Son.” Then she turned and gave the guys another insider's wink. 

“This is usually the part where 6 guys, in 3, separate, Father/Son teams, gang up on me. Then, 

they spend the next few hours, competing to see who is better at showing you, as my Son, 

exactly what it means to lend your whore Mommy out to them for the evening.”

Then, for the first time in, maybe longer than I could remember, my Mom proved to be wrong 

when reading people. Maybe because we told them they had the whole night, or maybe because 

of their age, or some other factor, but they didn’t split into 3 groups of 2. Instead, the Dads all 

said that they really wanted to have some fun with “the fantasy that I’d set up”. So, they pulled up 

their chairs, poured themselves some drinks, and “pretended” that my job application consisted 

of me making my Mom into their personal plaything. So they threw back a few drinks, and 

informed me that they wanted to “see what my Mother was made of”, first. They had their kids, 

all three of them, go at my Mom for their entertainment. I sat with them as they watched, and 

relayed their “orders” through me. So, I’d be stuck watching my Mom get taken from behind by 

my best friend, and then one of the Dad’s would get my attention, and say “I want to see how she 

handles two at once. Tell your Mom to have my Son join in, so we can watch them double team 

her” Then, even though we could all hear each other, my part in the game was to swallow my 

pride, get my Mom’s attention, and tell her what my potential bosses wanted. At which point she 

would stop to listen, smile in response, and say something like, “Of course sweetie!” Then she’d 

pause and feign confusion for a second before saying, “You brought so many friends to meet me 

tonight honey. Which one was he again?” Then, once I’d pointed him out, she wink, say “Got it.”, 

before calling him over, referencing him back to me and informing him, “My Son over there says 

he wants YOUR cock”, and she’d point to it before adding, “... down MY throat.” Again, she’d 

indicate the target destination and, every so sweetly, she’d ask him if that was okay with him. 

That was how it went, for HOURS. They had my Mom on her knees giving handjobs and 

blowjobs to all three of my friends. They had her spit-roasted, then made air tight. They had her 

ride one of them facing us, and when that wasn’t dirty enough, they had her riding him reverse 

cow-girl, still facing us; so that she could spread her legs, reach down, and spread her pussy 

lips in plain sight of us. When me “ordering my Mom” to do that got a heated reaction from the 

Dads of the group, they pushed it a little further.  They asked me if I’d ever purchased my own 

Mother’s services before, and when I told them no, they acted like that was a shame, and 

insisted that I should know what I was paying for. 

At first I thought they were about to have me go over there and join in, but they had something 

else in mind. Instead they had me ask my friend how it felt. So, I got to hear my friend describe in 

lurid detail to me how hot and tight he thought my Mother’s pussy was. They liked that so much 

they had another one of my buddies stand up beside her she could turn to the side, and start 

sucking his cock, giving us a side profile view of her giving head, even as she continued to show 

us the cock that was thrusting up into her, and spreading her from the inside. Naturally… they did 

this so that I could ask my other friend how good he thought my Mom was at sucking cock. 

Once again, as soon as they found an idea that they liked, they ran with it. So the next hour 

because my buddies putting my Mom’s incredible body on display as they defiled it in more and 

more ways and tried to tell me over the sound of her moans how fucking amazing it all felt. 

After 3 solid hours, and all 3 of my friends cumming several times, it finally seemed like they’d 

had enough and couldn’t go on anymore. Then, for just a second, I really thought it was over… 

As if the three men who’d wanted all of this to begin with would be content to go home blue 

balled, having done nothing but watch. But, of course, that wasn’t what happened. When it came 

time for “their turn”, they actually asked my Mom if they could “consult” with her. Even Mom 

seemed surprised at that one, if only for a second. But apparently, they wanted to go out with a 

bang, and they’d been enjoying “the fantasy roleplay” of her being my Mother so much, they 

wanted to ask her for her advice on what the filthiest, dirtiest things they could do as their final 

act. 

Mom thought about it for a minute, and the four of them actually got together and talked, laughed, 

and exchanged ideas for a several minutes while my buddies all thanked for me letting them 

gang-fuck my Mother, before heading off to the showers. Now, in their defense, they thought they 

were kidding. If they only knew… 

I was so shocked, and so turned on, and so overwhelmed by everything, that I somehow hadn’t 

cum despite seeing 100 new fantasies come to life and get carried out right in front of me. More 

than that, I was getting a little numb to how crazy it all was. So, when they all came out of their 

perverted little huddle and walked over to tell me what they’d come up with, I was honestly more 

turned on thinking about the possibilities than I was worried about what sick thing they’d 

managed to come up with. 

Mom sauntered up me with a sway to her hips that was still mesmerizing and sexual, even after 

everything I’d witnessed, and she leaned over, placed on hand on my shoulder, and whispered 

into my ear. She told me that since they’d already shown me everything that they’d been able to 

think of involving three guys, that they’d decided their last request needed to be something 

different. So, they wanted to really play up the fact that she was my Mom, and that I was letting 

them fuck her so that I could get a job at their company. She told me that, in my responses I 

should be a little reluctant, but always follow through. 

I wanted to ask what that meant, but we really didn’t have time. The first guy was already walking 

up to us, and so, Mom whispered one last little sentiment into my ear before it all started. She 

simply said, “I’m honestly enjoying this quite a bit. We might need to do something like this again 

in the future.” Then she pulled back, flashed me a smile both sinful and sincere, and stayed 

standing directing in front of me as my prospective employers came over to us. 

I really thought that they were coming over to tell me more about whatever perverted plan they’d 

come up with, and then lead my Mom over to the bed, like their kids had before them. But that 

SO wasn’t what happened. Instead the first guy walked up behind my Mom, reached around her, 

and began to lift and play with her big tits, practically right in front of my face. He started talking 

about how he’d had applicants try to bribe him before. How he’d been offered money, tickets to 

sporting events, but how he’d never imagined someone offering him their beautiful Mom to bend 

over and fuck however he pleased. At that point, he literally bent her over; but she was so close 

to me that she had to angle her head up and either keep it up and facing forward, or rest it on my 

chest or stomach. 

When he opened her up, he told me all about it. When he really started to get going, thrusting 

himself inside of her as he very quickly built to orgasm, he tried to tell me more; but it was hard 

to hear him over the sound of my Mom’s moans. Mostly because  she was so close to me that I 

could feel her breath through the fabric of my t-shirt, but also because she was so lusty and 

sincere in her vocalizations. When she moaned, you believed her, and when she cried out, “Fuck 

me!”, she did it with such needy desperation that you’d happily wear yourself our trying to keep 

whatever pace would make her happiest.  In a matter of minutes he was already at his limit and 

screaming about how he was going to cum. He quickly pulled out and came on my Mom’s ass. 

But no sooner had she grabbed a cloth, wiped her off, and collapsed into a nearby chair, then the 

next guy stepped up and took his spot. 

In line with their desires, Mom looked up at me feigning surprise. “Another one?” she asked, 

sounding  shocked, and breathy. Then the guy behind her told me that he thought the job he was 

in charge of was a little nicer than the last guys. That got a laugh out of all three of the “Dads”, 

but he flowed right from saying that, to telling me that he wanted to know if I’d let him, and I’m 

quoting here, “break open my sweet little Mommy’s ass”. The question threw me off. Like, even 

despite all the circumstances and the madness of the night, people had still been, I don’t know… 

respectful, I guess. Like, they wanted to pretend they were fucking my Mom, but as a side effect, 

they’d been treating her like a Mom. Mostly politely… kinda. But this was very different. He was 

talking about “wanting to plow her in the stinker”, and just using a bunch of terms that were 

beyond vulgar. 

I was a bit taken aback to be honest. But Mom read my pause for what it was, and immediately 

took back control of the situation. From practically in my lap, she turned her head to look back at 

the man behind her and said, “I don’t know sweetie. Mommy’s never let anyone in there before.” 

She said, lying smoothly in front of a room full of people who’d literally seen that what she was 

saying wasn’t true. But true or not, it didn’t matter. The guy behind her actually moaned and 

grabbed himself when she said it, clearly turned on by her words. Then Mom continued, looking 

back to me, “He looks BIG too sweetheart. Much bigger than your Father… How badly do you 

want this job slugger? I mean, are you really going to tell that man that he can force that giant 

thing into your own Mother’s tight little VIRGIN asshole?” 

Fuck. She even had me squirming now. I’d have grabbed my own cock, but my Mother’s large, 

naked tits were in the way, and we were already WAY too close. 

We all knew what the answer was going to be. What it HAD to be. It wasn’t like after hours of 

having my Mom fuck and suck my three best friends and their Dad’s that I could suddenly turn it 

off and undo it. But after a few seconds, I looked down at my Mom’s face, and she’d dropped the 

innocence and concern from her face. She was looking back up at me with a wicked curve of 

her lips that, after making my heart hammer at twice its normal speed, also communicated to 

me that I was now expected to do exactly as she’d said. I was supposed to tell him that he could 

take my Mom’s anal virginity. 

Double Fuck. 

I managed to tell him, and I even did my best to phrase it in as dirty and depraved a way as I 

could manage, since that seemed to be what they were going for here. But even after talking 

about it, telling him to do it, and watching him lube up and push in, I somehow wasn’t ready for 

Mom gripping my thigh, biting down on part of my t-shirt, and crying out, “Oh God! I can feel your 

future boss baby! His GIANT fucking cock feels like it going to split your Mother in two!” 

Mercifully, it didn’t take very much of that to set him off. Mom kept talking about how he was 

splitting her open, and how big he was, and how it felt so big in her tiny little asshole. She told 

him every depraved thing he wanted to hear, and just when it seemed like she’d given him all of 

the dialogue and roleplay that he could ever want, and more, he threw in one last request. “I want 

to cum inside her ass”, he declared out of fucking nowhere.  

A LOT of cum had gone down my Mom’s throat that night, but that was the only kind of 

“cumming inside” that anyone had dared to mention. This was huge, right? I had no idea what to 

say. But as he was clearly struggling to hold back, and needed an answer FAST, all I could do 

was look to my Mom. For her part, she just kept moaning, and grabbing at me, the chair, and my 

clothes for support as she squirmed and writhed in pleasure. So, I figured this was all part of the 

plan, and fell under her previous instructions to “Be reluctant, but basically say yes to 

everything.” My confidence was shaken for a moment though, when I said yes, and Mom 

immediately popped her head up, and gave a shocked “What?!” He started fucking her harder, 

and it was blatantly already too late. But, she still took the time, in between moans, to cry out, 

“Did you just tell your future boss that he could blow his load inside of your Mom!?”  

Then he did exactly that, and if you could get a heart attack from being too overwhelmed with 

hornyness, I’d have fucking died when, as he thrust himself all the way inside of her, my Mom 

started giving me the play by play of how she could feel his hot cum splashing inside of her. She 

talked about his warmth filling her up. With a throaty moan, she told me that he was still going, 

and confided that he was emptying his balls directly into my “Mommy”. 

When he finally pulled out of her, you’ve never seen someone look so satisfied, happy, or spent. 

There was a brief moment where even the guy who hadn’t done anything yet needed to recover 

from how intense what he was watching had felt. Mom seized that Moment. She acted like she 

was propping herself up to rest on my shoulders, and catch her breath. But while she was there, 

ever so quietly, she whispered, “You're doing great sweetie. It’s all part of the plan. Remember, 

reluctant, but say yes… It’s okay.” 

Then, out loud, she gave a sigh, and still sounding out of breath, she commented loud enough 

for everyone to hear, “My goodness sweetie. I cannot BELIEVE how badly you wanted these 

jobs! I mean wow! You really put your Mother through the paces tonight!”. Then she gave a 

surprised little yelp as the third man arrived behind her, grabbed her hips, spread her legs with a 

push from one of his feet to hers, and pulled her ass up and back towards him. 

Mom’s squeak of surprise was followed by a wide-eyed glance over her shoulder at the man 

behind her, who was lining up his dick with the slit of her pussy. “Three!” she said, before looking 

back at me. “Three recruiters! How many jobs do you need-”, and then she began to say my first 

name, but she only got a half a syllable in before my name was twisted into a cry of pleasure. 

Then her face went from indignant shock to barely contained lust, as she confessed how 

pleasurable it all was to her, via the question, “... and why do they all have such nice dicks, that 

feel SO good inside me?” 

After a minute, my third prospective employer was balls deep in my Mom. At that point, wrapped 

an arm around her midsection, and guided her to her feet. It was an awkward stance, but with 

the way Mom’s feet were set apart, the result was that I was now, not only looking at her as he 

groped her massive tits in front of me; but also that I could see everything. Like, everything 

everything! I was watching this guy's dick as it spread my Mother’s pussy apart from just a few 

feet away, and I could see and hear as that dick slowly pushed in and out of my Mom. It was 

making small… “squishing” noises, as it also drew little whimpers and moans from her Other 

lips. 

I was so busy staring, and so lost in watching the “sex” part of them fucking, that I didn’t hear it 

the first time he addressed me directly. Then he laughed, and stopped groping my Mother’s tits 

long enough to snap his fingers in front of me (in between me and Mom really), to get my 

attention. When he was sure he had it again, he told me I needed to take my pants off or I was 

going to die; and that wouldn’t do since he was pretty sure I was going to get three really nice job 

offers as a result of the night's activities. At first I wanted to say no, but it only took a second of 

rapid, panicked thinking to realize that I couldn’t exactly say that I wanted to keep my pants on 

because that was my real Mother he was buried in!

With no excuse, and knowing that any delay would only raise suspicions or discomforts that I 

couldn’t afford, I ended up stripping from the waist down. Once I’d finished kicking my pants free 

from around my ankles, I had to admit that the answer to his next question, asking if that didn’t 

feel 100 times better, was definitely yes! I hadn’t wanted Mom to see it, but I’d been hard and 

leaking the entire time, and not being trapped in my clothes felt fucking amazing after all of that. 

I admitted as much, but before the relief could really set in, he switched me right back to anxiety 

when told me that now that I was out, I could see the real benefit of how big my Mother’s tits 

were. At first he actually said, “Our little whore’s tits”, but then he corrected himself, adding, “I 

mean your Mother’s tits.” 

I didn't even have time to question what that might mean, as, immediately after saying it, he 

pushed her back down with a little surprised yelp, and she once more fell into my lap. Except 

that, this time, her naked tits crushed into me skin to skin, and my hard cock quickly managed to 

find its way into her cleavage line. I clenched my teeth and hissed through them as I braced 

through almost overwhelming pleasure. Mom quickly propped herself back up on her elbows, 

and gave me a look that told me that not even she was not expecting that, and she tried to 

apologize with her eyes without “breaking character”. 

Then he pulled his hips back, and gave her a quick hard thrust that made that “CLAP” sound that 

good, rough sex always seems to have. When he did, her body was pushed more into me, and 

her breasts rocked forward with the motion, brushing against my thighs, and even briefly kissing 

against my shaft and balls. I moaned and squirmed, a second after my Mother did. Then he did it 

again. Again, and again, and again. As he did, he locked down onto the Mom thing, and, out of 

fucking nowhere, he asked me if my Mother ever went to church. 

I… I had no idea what to say to that. Then he thrust into her again, and she let out a cry of 

pleasure that was echoed by me a second after as her massive breasts continued to brush 

against me, skin to skin. He did that one more time before asking again, and I was once more 

reminded that there was no reason that I could refuse, or even hesitate, that I could actually 

share with the people who were there. So, I did the only thing I could, and played along with it. I 

told him yes, and a second later, when he asked me what the sexiest thing my Mom ever wore to 

church was, Mom’s eyes shot up to mine. At first I thought it might be because something was 

wrong, or she didn’t want me to say. But as she licked her full red lips (she’d reapplied her 

lipstick earlier), and gave another whimper of pleasure, I realized that she actually wanted to hear 

my answer! 

I told him about a low dipping dress she’d worn on more than one occasion, and I described it to 

him like I never would have to her. I gave him the honest description of a dress that showed off 

my Mom’s big tits and perfect ass, and left me needing to masturbate after church… 

For some reason, that did it for him, and he gave a teeth gritted “fuck yeah!” before asking if she 

was in the PTA or involved in my school life at all. Again, with Mom moaning and rocking in my 

lap, I admitted that yeah, she’d been great about that kind of thing, and I struggled a bit more with 

the question of what was the sexiest thing she’d ever worn to my school. It wasn’t because I 

didn’t know the answer, I straight up fucking did! But having no good excuse to stall, I then told 

him about the jean shorts and tied top she’d worn once to one of my sporting events, and how all 

of my friends, the whole team, and even several of my enemies had later told me had made 

them hard. Not just that day, but in the many times after when they’d thought about her wearing 

it. 

He started to ask another question, this one about her reading me bed time stories or something. 

But, he was interrupted by Mom’s moans, and a sudden urgency from her that had her pushing 

back against his thrusts, and almost taking total control of the sex in the process. As she did, 

she cursed, and looked away, and seemed like she was going to cum any second. Then she 

confessed that she never knew my friends from highschool, or my teammates (or the opposing 

team for that matter), had all been secretly lusting after her! She was gritting her teeth and 

looking almost like she was trying not to cum. When I admitted that pretty much every friend I 

had, had jerked off while thinking about her on a regular basis, she went from trying not to cum to 

having a loud and violent orgasm. 

Her hips were pounding back into the guy behind her, and her breasts were all over me as she 

pressed into me and screamed and moaned out her pleasure! When she was done, and slowed 

to a stop, finally… The guy behind her and I were both breathing hard, and gripping our hands like 

we were going to fall off a cliff as we struggled not to cum. He didn’t want it to end too quickly, 

and I was trying not to cum on my own Mother!

Mom seemed to blush, and though she didn’t apologize, I got the sense that what I had just 

witnessed was an incredibly real moment from her, and that she’d lost control of herself in a very 

uncharacteristic way. Of course, with no knowledge that we really even knew one another, let 

alone that she was one of my parents; the guy behind her just thought it was all part of the show, 

and he was loving it!

When he finally got a hold of himself, we both ended up sharing “holy shit that was intense” looks 

for a solid minute as we silently agreed to take a minute to calm down. For her part, Mom didn’t 

say anything, she just gave us our time. It uninterrupted except for the occasional tiny moan, 

whimper or adjustment that resulted from her both LOVING sex, and still having a hard dick 

inside of her. 

When the minute was up, the silence was broken by him saying (though in my head he blurted it 

out like a crazy person!), “I want to cum in her pussy”. And with that, my brain gave up. It just, it 

couldn’t. I felt my ability to think crash like an engine with a wrench thrown into it. I must have 

looked it to, because he stopped waiting for a reply, and just continued talking after a minute. He 

named one of the other guys, and pointed out that he’d gotten to cum in her ass. Then, as if he 

wasn’t proposing cumming inside my Mother’s womb, he just ever so casually pointed out that if 

he got to cum inside her pussy, then he and his buddies would have cum inside all of her holes. 

At that, Mom, in a way that REALLY didn’t seem very helpful, said, “Well… that’s not exactly true. 

I mean… That first man came on my skin, so it’s not like any of you have cum in my mouth…” 

When she did, he actually looked up at me, and, making eye contact with me directly, the guy 

behind my Mom said, “I think we can fix that too. Can’t we?”, and then he winked at me! 

FUCKING WHAT!!!???!!!

I looked down at my Mom, trying to look cool and collected on the outside, while also thinking that 

she is about to freak out, throw us all out, and rightfully destroy everything. But she just smiled at 

me, her full lips still painted red. Then she licked them, slowly, and seductively. When I didn’t 

come down from my panic, she smiled. Then she winked at me too. And when I still didn’t do 

anything, she gently took one of my hands into hers, and placed it on the back of her head; just in 

case I’d missed her meaning!

Then Mom went all innocent voiced again, and asked what I was planning on doing. If I really 

want these jobs so badly that I’m going PARTICIPATE in Spit-Roasting my Mommy and filling her 

with cum from both ends.

But even though part of me was still freaking out, if I was being honest, I could have admitted that 

everyone knew it was part of the show by then. And they LOVED the show! 

Still, even after everything, I wasn’t sure if I could do it. If I could go all the way with my own Mom 

just for some job! But in her head, I’d made my decision hours ago when I answered her 

question of, “How badly” I wanted this. So, Mom arched her back, and as she lowered her ass, 

and rolled her body back into position with deeply sexual grace, she once again forced my Cock 

into her cleavage line and had me bucking up into her on instinct. Fucking my Mother’s tits 

without trying to. Then, the moment I had enough bodily control to open my eyes again, Mom 

wasted no time. She reached in between her tits, wrapped my dick in her delicate grip, and 

aimed the tip of it at her face. Then she said, “Well sweetie… I guess since we’ve come this far, 

we should follow through, huh? I mean, you already decided that you were going to use your own 

Mother as a whore to help you secure these jobs. So I guess now it’s just a matter of following 

through. Pushing your own cock into your Mother’s waiting mouth, and proving to everyone here 

just how dedicated you and your Whore Mommy really are.” 

Then she wrapped her lips around the head of my cock, slid them down to the root, with a long 

throaty moan, and began to give me the greatest blowjob of my life! As she did, I cried out 

something along the lines of, “Oh fuck Mom!”, and the guy behind her absolutely lost it! He went 

from dead still, and seeming to have all the control, to grabbing onto her hips and slamming my 

Mother’s cunt like an absolute wild man. 

I don’t know how I didn’t pop instantly, but instead I felt this massive orgasmic preasure building 

up in me, and getting bigger and bigger as I felt it all building towards the surface. I didn’t make it 

past the guy behind her screaming that he was filling up my Mother’s tight little cunt with his cum 

though. So in no time at all, we were all screaming and moaning and orgasming as Mom came 

all over the guy behind her as he was cumming her pussy and I was shooting what felt like 50 

gallons of cum down her throat!

I felt myself blasting load after load down deep inside of her, and I imagined something similar 

was happening on the other end, but as long as my orgasm lasted, Mom’s was longer. She 

seemed endlessly needy and greedy as she just kept rolling her hips back and plunging her lips 

down long after she finished jerking everything I had to give down into the inside of her. Finally the 

guy behind her pulled away and fell to the floor muting “Holy fuck!”, and scrambling back away 

from her like she was going to run him down and fuck him to death if he didn’t crawl away fast 

enough. 

Then he laughed, and his buddies joined him. All amazed and blown away by “the show” that 

Mom had put on for everyone. She started to calm down then, and though she looked up at me 

with a lust so intense I thought I might cum a second time from just that glance… She eventually 

regained total control, and stood up. She put her Kimono back on, gave everyone smiles, winks, 

and compliments; and with an exaggerated tone, she confessed that she didn’t know about 

everyone else, but she needed a drink! 

That got another laugh, and Mom hit an intercom sending a message for my buddies to come 

back. Apparently their Dad’s had wanted them in the waiting room for their portion, and I just 

hadn’t noticed the exchange. Mom had some food, snacks, and drinks brought in for us, and she 

spent another 45 minutes playing hostess, serving food, and never dropping the “act” that she 

was my Mother. 

In the end, we all left with full bellies, empty balls, and the closest thing to total satisfaction that I 

think maybe any group of people had ever experienced in their lives! The whole ride back was 

everyone raving about how they’d just had what was probably the best night of their lives, and 

when we got back to the dorm, everyone was commenting on what a “great sport” I’d been with 

their roleplay choice. My buddies talked about going back, but their Dad’s quickly pointed out that 

none of them could afford to visit my Mom’s place of business, and they were not about to front 

them that money. 

A year later, when I first truly qualified, all three of them made incredible job offers. I took the one 

that paid the most, and I honestly really thrived. The “Dad” who’d brought me in doubled down on 

his bet and tied himself to my career. He vouched for me in everything, and it paid off. I did great, 

and we both got promoted together. Eventually another company bought it, but it was owned by 

the second of the three men and, you guessed it, within three years all three rival companies had 

merged, giving them no competition in the region. 

We threw a party, and it was then that as soon as their Son’s had gotten jobs at their respective 

companies, they’d admitted to going back to my Mother’s business as often as they could, 

though they were happy to explore all the possibilities. In other words, they didn’t focus on my 

Mom, just on the incredible services that her business offered. 

Which was both disturbing and a relief in the space of a few sentences. Later on, they also 

admitted to me that they went back as well, but they’d also asked after “the same woman” and 

“the same roleplay”; confessing that they’d found the whole thing to be hotter than they’d ever 

expected. After a few minutes had passed, I asked why, after two years, they were suddenly so 

big on sharing information about that night and what had happened since, and they all shared a 

grin, then they took me to a side office. They told me that I’d been doing great, and that I was 

actually about to be promoted to the same level as them based on all my hard work and results. 

Which sounded amazing, but I hear the “but” coming from a mile away. “But…” they continued. 

They’d told their boss, my new boss, about how I’d impressed them on that first night. Like, 

exactly how I’d done it. So, when he heard… it made him want to do it too. 

Oh god. 

So yeah. Next week, there is going to be a little office party on the top floor in order to celebrate 

my promotion. Then, during the party, which would include the original “3 dads'', my new boss, 

and about 6 of my new underlings; my new boss was going to say something like, how he found 

about my Mom had been working as a high end whore just a few hours from the office, and when 

he confronted me about it, I’d said that I’d not only known about it, but was cool with it. Then, 

having laid that groundwork, he was going to say that, once he knew I was okay with it, he 

decided to hire her for the office, in order to celebrate my promotion…

At which point they would bring in my Mother. My real Mother, though they still thought it was all 

pretend. Then they were going to put her center stage, have her strip while she apologized to me 

for any awkwardness her profession was causing me in that moment, all the while, she'd be playing 

up the Mom/Son angle. Then, they would have 6 underlings, 3 peers, and my boss, all gangbang her 

in front of me. Knowing full well that, while they did, she would be moaning about how much she loved 

that I’d turned my Mother into a whore for my whole office.

So I guess what I’m saying is, my life is perfect now. And my Mom? Well, I made a case for 

using some of our budget for keeping her on retainer, full time. 

So now… Well now, my Mommy really is the office whore. 

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